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<span>Biosynthesis</span> </div> </a> <button aria-controls="toc-Biosynthesis-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Biosynthesis subsection</span> </button> <ul id="toc-Biosynthesis-sublist" class="vector-toc-list"> <li id="toc-Extramitochondrial" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Extramitochondrial"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>Extramitochondrial</span> </div> </a> <ul id="toc-Extramitochondrial-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Intramitochondrial" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Intramitochondrial"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.2</span> <span>Intramitochondrial</span> </div> </a> <ul id="toc-Intramitochondrial-sublist" class="vector-toc-list"> </ul> 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id="toc-Interactive_pathway_map" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Interactive_pathway_map"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Interactive pathway map</span> </div> </a> <ul id="toc-Interactive_pathway_map-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Acetyl-CoA</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 37 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-37" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">37 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%A3%D8%B3%D9%8A%D8%AA%D9%8A%D9%84_%D9%83%D9%88-%D8%A3" title="أسيتيل كو-أ – Arabic" lang="ar" hreflang="ar" data-title="أسيتيل كو-أ" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%A7%D8%B3%D8%AA%DB%8C%D9%84-%DA%A9%D9%88%D8%A2" title="استیل-کوآ – South Azerbaijani" lang="azb" hreflang="azb" data-title="استیل-کوآ" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bo mw-list-item"><a href="https://bo.wikipedia.org/wiki/%E0%BD%A8%E0%BD%BA%E0%BC%8B%E0%BD%A6%E0%BD%B2%E0%BC%8B%E0%BD%8A%E0%BD%B2%E0%BD%A3%E0%BC%8B%E0%BD%A6%E0%BE%A8%E0%BD%B2%E0%BD%93%E0%BC%8B%E0%BD%82%E0%BE%B2%E0%BD%BC%E0%BD%82%E0%BD%A6%E0%BC%8B%E0%BD%A8%E0%BD%BA%E0%BC%8D" title="ཨེ་སི་ཊིལ་སྨིན་གྲོགས་ཨེ། – Tibetan" lang="bo" hreflang="bo" data-title="ཨེ་སི་ཊིལ་སྨིན་གྲོགས་ཨེ།" data-language-autonym="བོད་ཡིག" data-language-local-name="Tibetan" class="interlanguage-link-target"><span>བོད་ཡིག</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Acetil_koenzim_A" title="Acetil koenzim A – Bosnian" lang="bs" hreflang="bs" data-title="Acetil koenzim A" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Acetil-CoA" title="Acetil-CoA – Catalan" lang="ca" hreflang="ca" data-title="Acetil-CoA" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Acetylkoenzym_A" title="Acetylkoenzym A – Czech" lang="cs" hreflang="cs" data-title="Acetylkoenzym A" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Acetyl-Coenzym_A" title="Acetyl-Coenzym A – German" lang="de" hreflang="de" data-title="Acetyl-Coenzym A" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Atset%C3%BC%C3%BClkoens%C3%BC%C3%BCm_A" title="Atsetüülkoensüüm A – Estonian" lang="et" hreflang="et" data-title="Atsetüülkoensüüm A" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Acetil-CoA" title="Acetil-CoA – Spanish" lang="es" hreflang="es" data-title="Acetil-CoA" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Acetila_koenzimo_A" title="Acetila koenzimo A – Esperanto" lang="eo" hreflang="eo" data-title="Acetila koenzimo A" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Azetil-CoA" title="Azetil-CoA – Basque" lang="eu" hreflang="eu" data-title="Azetil-CoA" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A7%D8%B3%D8%AA%DB%8C%D9%84-%DA%A9%D9%88%D8%A2" title="استیل-کوآ – Persian" lang="fa" hreflang="fa" data-title="استیل-کوآ" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Ac%C3%A9tyl-coenzyme_A" title="Acétyl-coenzyme A – French" lang="fr" hreflang="fr" data-title="Acétyl-coenzyme A" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Acetil_coencima_A" title="Acetil coencima A – Galician" lang="gl" hreflang="gl" data-title="Acetil coencima A" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%95%84%EC%84%B8%ED%8B%B8-CoA" title="아세틸-CoA – Korean" lang="ko" hreflang="ko" data-title="아세틸-CoA" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Acetil_koenzim_A" title="Acetil koenzim A – Croatian" lang="hr" hreflang="hr" data-title="Acetil koenzim A" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Asetil-KoA" title="Asetil-KoA – Indonesian" lang="id" hreflang="id" data-title="Asetil-KoA" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Acetil-coenzima_A" title="Acetil-coenzima A – Italian" lang="it" hreflang="it" data-title="Acetil-coenzima A" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%90%D7%A6%D7%98%D7%99%D7%9C_%D7%A7%D7%95%D7%90%D7%A0%D7%96%D7%99%D7%9D_A" title="אצטיל קואנזים A – Hebrew" lang="he" hreflang="he" data-title="אצטיל קואנזים A" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-lb mw-list-item"><a href="https://lb.wikipedia.org/wiki/HSCoA" title="HSCoA – Luxembourgish" lang="lb" hreflang="lb" data-title="HSCoA" data-language-autonym="Lëtzebuergesch" data-language-local-name="Luxembourgish" class="interlanguage-link-target"><span>Lëtzebuergesch</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Acetil-koenzim-A" title="Acetil-koenzim-A – Hungarian" lang="hu" hreflang="hu" data-title="Acetil-koenzim-A" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Asetil-KoA" title="Asetil-KoA – Malay" lang="ms" hreflang="ms" data-title="Asetil-KoA" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Acetyl-CoA" title="Acetyl-CoA – Dutch" lang="nl" hreflang="nl" data-title="Acetyl-CoA" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%A2%E3%82%BB%E3%83%81%E3%83%ABCoA" title="アセチルCoA – Japanese" lang="ja" hreflang="ja" data-title="アセチルCoA" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Acetyl-CoA" title="Acetyl-CoA – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Acetyl-CoA" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Acetilcoenzima_A" title="Acetilcoenzima A – Portuguese" lang="pt" hreflang="pt" data-title="Acetilcoenzima A" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Acetil-CoA" title="Acetil-CoA – Romanian" lang="ro" hreflang="ro" data-title="Acetil-CoA" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%90%D1%86%D0%B5%D1%82%D0%B8%D0%BB-%D0%9A%D0%BE%D0%90" title="Ацетил-КоА – Russian" lang="ru" hreflang="ru" data-title="Ацетил-КоА" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Acetylkoenz%C3%BDm_A" title="Acetylkoenzým A – Slovak" lang="sk" hreflang="sk" data-title="Acetylkoenzým A" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Acetil_koenzim_A" title="Acetil koenzim A – Serbian" lang="sr" hreflang="sr" data-title="Acetil koenzim A" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Acetil_koenzim_A" title="Acetil koenzim A – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Acetil koenzim A" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Asetyylikoentsyymi-A" title="Asetyylikoentsyymi-A – Finnish" lang="fi" hreflang="fi" data-title="Asetyylikoentsyymi-A" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Acetyl-CoA" title="Acetyl-CoA – Swedish" lang="sv" hreflang="sv" data-title="Acetyl-CoA" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B8%AD%E0%B8%B0%E0%B8%8B%E0%B8%B4%E0%B8%95%E0%B8%B4%E0%B8%A5%E0%B9%82%E0%B8%84%E0%B9%80%E0%B8%AD%E0%B8%99%E0%B9%84%E0%B8%8B%E0%B8%A1%E0%B9%8C_%E0%B9%80%E0%B8%AD" title="อะซิติลโคเอนไซม์ เอ – Thai" lang="th" hreflang="th" data-title="อะซิติลโคเอนไซม์ เอ" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Asetil_koenzim_A" title="Asetil koenzim A – Turkish" lang="tr" hreflang="tr" data-title="Asetil koenzim A" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%90%D1%86%D0%B5%D1%82%D0%B8%D0%BB-%D0%9A%D0%BE%D0%90" title="Ацетил-КоА – Ukrainian" lang="uk" hreflang="uk" data-title="Ацетил-КоА" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E4%B9%99%E9%85%B0%E8%BE%85%E9%85%B6A" title="乙酰辅酶A – Chinese" lang="zh" hreflang="zh" data-title="乙酰辅酶A" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q715317#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div 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ambox-citation_style" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/f/f2/Edit-clear.svg/40px-Edit-clear.svg.png" decoding="async" width="40" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/f2/Edit-clear.svg/60px-Edit-clear.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/f2/Edit-clear.svg/80px-Edit-clear.svg.png 2x" data-file-width="48" data-file-height="48" /></span></span></div></td><td class="mbox-text"><div class="mbox-text-span">This article <b>has an unclear <a href="/wiki/Wikipedia:Citing_sources#Citation_style" title="Wikipedia:Citing sources">citation style</a></b>. The reason given is: <b>Multiple page-numbers in a single ref that is used multiple times: unclear which supports which. Some ISBN might be for wrong edition of the book. Need page-numbers for refs to whole broad-coverage textbooks.</b><span class="hide-when-compact"> The references used may be made clearer with a different or consistent style of <a href="/wiki/Wikipedia:Citing_sources" title="Wikipedia:Citing sources">citation</a> and <a href="/wiki/Help:Footnotes" title="Help:Footnotes">footnoting</a>.</span> <span class="date-container"><i>(<span class="date">August 2017</span>)</i></span><span class="hide-when-compact"><i> (<small><a href="/wiki/Help:Maintenance_template_removal" title="Help:Maintenance template removal">Learn how and when to remove this message</a></small>)</i></span></div></td></tr></tbody></table> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1251242444"><table class="box-Expert_needed plainlinks metadata ambox ambox-content" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/b/b4/Ambox_important.svg/40px-Ambox_important.svg.png" decoding="async" width="40" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/b/b4/Ambox_important.svg/60px-Ambox_important.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/b/b4/Ambox_important.svg/80px-Ambox_important.svg.png 2x" data-file-width="40" data-file-height="40" /></span></span></div></td><td class="mbox-text"><div class="mbox-text-span">This article <b>needs attention from an expert in Biochemistry</b>. The specific problem is: <b>Per <a href="/wiki/Talk:Fatty_acyl-CoA_esters#c-Teaktl17-20240804223600-DeemDeem52-20240529152800" title="Talk:Fatty acyl-CoA esters">this talk page</a>: Needs more context about benzoyl-CoA and lactoyl-CoA. Some content needs to be moved to acyl-CoA article to fatty acyl-CoA..</b><span class="hide-when-compact"> <a href="/wiki/Wikipedia:WikiProject_Biochemistry" class="mw-redirect" title="Wikipedia:WikiProject Biochemistry">WikiProject Biochemistry</a> may be able to help recruit an expert.</span> <span class="date-container"><i>(<span class="date">August 2024</span>)</i></span></div></td></tr></tbody></table> </div> </div><span class="hide-when-compact"><i> (<small><a href="/wiki/Help:Maintenance_template_removal" title="Help:Maintenance template removal">Learn how and when to remove this message</a></small>)</i></span></div></td></tr></tbody></table><style data-mw-deduplicate="TemplateStyles:r1084375498">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> <table class="infobox ib-chembox"> <caption>Acetyl-CoA </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Acetyl-CoA-2D_colored.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/14/Acetyl-CoA-2D_colored.svg/320px-Acetyl-CoA-2D_colored.svg.png" decoding="async" width="320" height="117" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/14/Acetyl-CoA-2D_colored.svg/480px-Acetyl-CoA-2D_colored.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/14/Acetyl-CoA-2D_colored.svg/640px-Acetyl-CoA-2D_colored.svg.png 2x" data-file-width="512" data-file-height="187" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Acetyl-CoA-3D-balls.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e1/Acetyl-CoA-3D-balls.png/320px-Acetyl-CoA-3D-balls.png" decoding="async" width="320" height="109" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e1/Acetyl-CoA-3D-balls.png/480px-Acetyl-CoA-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e1/Acetyl-CoA-3D-balls.png/640px-Acetyl-CoA-3D-balls.png 2x" data-file-width="1100" data-file-height="373" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Acetyl-CoA-3D-vdW.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/da/Acetyl-CoA-3D-vdW.png/320px-Acetyl-CoA-3D-vdW.png" decoding="async" width="320" height="127" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/da/Acetyl-CoA-3D-vdW.png/480px-Acetyl-CoA-3D-vdW.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/da/Acetyl-CoA-3D-vdW.png/640px-Acetyl-CoA-3D-vdW.png 2x" data-file-width="1100" data-file-height="435" /></a></span> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;"><i>O</i><sup>1</sup>-{(3<i>R</i>)-4-[(3-{[2-(Acetylsulfanyl)ethyl]amino}-3-oxopropyl)amino]-3-hydroxy-2,2-dimethyl-4-oxobutyl} <i>O</i><sup>3</sup>-{[(2<i>R</i>,3<i>S</i>,4<i>R</i>,5<i>R</i>)-5-(6-amino-9<i>H</i>-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methyl} dihydrogen diphosphate</div></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=72-89-9">72-89-9</a></span> (free acid)<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=O%3DC%28SCCNC%28%3DO%29CCNC%28%3DO%29%5BC%40H%5D%28O%29C%28C%29%28C%29COP%28%3DO%29%28O%29OP%28%3DO%29%28O%29OC%5BC%40H%5D3O%5BC%40%40H%5D%28n2cnc1c%28ncnc12%29N%29%5BC%40H%5D%28O%29%5BC%40%40H%5D3OP%28%3DO%29%28O%29O%29C">Interactive image</a></span></li><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=CC%28%3DO%29SCCNC%28%3DO%29CCNC%28%3DO%29%5BC%40%40H%5D%28C%28C%29%28C%29COP%28%3DO%29%28O%29OP%28%3DO%29%28O%29OC%5BC%40%40H%5D1%5BC%40H%5D%28%5BC%40H%5D%28%5BC%40%40H%5D%28O1%29n2cnc3c2ncnc3N%29O%29OP%28%3DO%29%28O%29O%29O">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=15351">CHEBI:15351</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.392413.html">392413</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.000.719">100.000.719</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q715317#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/IUPHAR/BPS" class="mw-redirect" title="IUPHAR/BPS">IUPHAR/BPS</a></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.guidetopharmacology.org"><a rel="nofollow" class="external text" href="http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?tab=summary&ligandId=3038">3038</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C00024">C00024</a></span><sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Medical_Subject_Headings" title="Medical Subject Headings">MeSH</a> </td> <td><span title="www.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://www.nlm.nih.gov/cgi/mesh/2014/MB_cgi?mode=&term=Acetyl+Coenzyme+A">Acetyl+Coenzyme+A</a></span> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/444493">444493</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/76Q83YLO3O">76Q83YLO3O</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID30992686">DTXSID30992686</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q715317#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C23H38N7O17P3S/c1-12(31)51-7-6-25-14(32)4-5-26-21(35)18(34)23(2,3)9-44-50(41,42)47-49(39,40)43-8-13-17(46-48(36,37)38)16(33)22(45-13)30-11-29-15-19(24)27-10-28-20(15)30/h10-11,13,16-18,22,33-34H,4-9H2,1-3H3,(H,25,32)(H,26,35)(H,39,40)(H,41,42)(H2,24,27,28)(H2,36,37,38)/t13-,16-,17-,18+,22-/m1/s1<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: ZSLZBFCDCINBPY-ZSJPKINUSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/C23H38N7O17P3S/c1-12(31)51-7-6-25-14(32)4-5-26-21(35)18(34)23(2,3)9-44-50(41,42)47-49(39,40)43-8-13-17(46-48(36,37)38)16(33)22(45-13)30-11-29-15-19(24)27-10-28-20(15)30/h10-11,13,16-18,22,33-34H,4-9H2,1-3H3,(H,25,32)(H,26,35)(H,39,40)(H,41,42)(H2,24,27,28)(H2,36,37,38)/t13-,16-,17-,18+,22-/m1/s1</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: ZSLZBFCDCINBPY-ZSJPKINUBJ</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">O=C(SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@H]3O[C@@H](n2cnc1c(ncnc12)N)[C@H](O)[C@@H]3OP(=O)(O)O)C</div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">CC(=O)SCCNC(=O)CCNC(=O)[C@@H](C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)n2cnc3c2ncnc3N)O)OP(=O)(O)O)O</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>23</sub><span title="Hydrogen">H</span><sub>38</sub><span title="Nitrogen">N</span><sub>7</sub><span title="Oxygen">O</span><sub>17</sub><span title="Phosphorus">P</span><sub>3</sub><span title="Sulfur">S</span> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002809570000000000♠"></span>809.57</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td><a href="/wiki/Ultraviolet%E2%80%93visible_spectroscopy" title="Ultraviolet–visible spectroscopy">UV-vis</a> (λ<sub>max</sub>) </td> <td>260 nm; 232 nm<sup id="cite_ref-lamda_source_1_1-0" class="reference"><a href="#cite_note-lamda_source_1-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Absorbance" title="Absorbance">Absorbance</a> </td> <td><a href="/wiki/Molar_attenuation_coefficient" class="mw-redirect" title="Molar attenuation coefficient">ε<sub>260</sub></a> = 16.4 mM<sup>−1</sup> cm<sup>−1</sup> (adenosine)<sup id="cite_ref-lamda_source_1_1-1" class="reference"><a href="#cite_note-lamda_source_1-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><br /> <a href="/wiki/Molar_attenuation_coefficient" class="mw-redirect" title="Molar attenuation coefficient">ε<sub>232</sub></a> = 8.7 mM<sup>−1</sup> cm<sup>−1</sup> (thioester)<sup id="cite_ref-lamda_source_1_1-2" class="reference"><a href="#cite_note-lamda_source_1-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><br /> Δ<a href="/wiki/Molar_attenuation_coefficient" class="mw-redirect" title="Molar attenuation coefficient">ε<sub>232</sub></a> on thioester hydrolysis = −4.5 mM<sup>−1</sup> cm<sup>−1</sup><sup id="cite_ref-lamda_source_1_1-3" class="reference"><a href="#cite_note-lamda_source_1-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/12px-X_mark.svg.png" decoding="async" width="12" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/18px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/24px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=477240040&page2=Acetyl-CoA">verify</a></span> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <sup><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup> ?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>Acetyl-CoA</b> (<b>acetyl coenzyme A</b>) is a molecule that participates in many <a href="/wiki/Biochemical_reaction" class="mw-redirect" title="Biochemical reaction">biochemical reactions</a> in protein, carbohydrate and lipid <a href="/wiki/Metabolism" title="Metabolism">metabolism</a>.<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Its main function is to deliver the <a href="/wiki/Acetyl" class="mw-redirect" title="Acetyl">acetyl</a> group to the <a href="/wiki/Citric_acid_cycle" title="Citric acid cycle">citric acid cycle</a> (Krebs cycle) to be <a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">oxidized</a> for energy production. </p><p><a href="/wiki/Coenzyme_A" title="Coenzyme A">Coenzyme A</a> (CoASH or CoA) consists of a <a href="/wiki/Cysteamine" title="Cysteamine">β-mercaptoethylamine group</a> linked to <a href="/wiki/Pantothenic_acid" title="Pantothenic acid">pantothenic acid</a> (vitamin B5) through an <a href="/wiki/Amide_linkage" class="mw-redirect" title="Amide linkage">amide linkage</a><sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> and 3'-phosphorylated ADP. The acetyl group (indicated in blue in the structural diagram on the right) of acetyl-CoA is linked to the <a href="/wiki/Sulfhydryl" class="mw-redirect" title="Sulfhydryl">sulfhydryl</a> substituent of the β-mercaptoethylamine group. This <a href="/wiki/Thioester" title="Thioester">thioester</a> linkage is a "high energy" bond, which is particularly reactive. <a href="/wiki/Hydrolysis" title="Hydrolysis">Hydrolysis</a> of the thioester bond is <a href="/wiki/Exergonic" class="mw-redirect" title="Exergonic">exergonic</a> (−31.5 kJ/mol). </p><p>CoA is acetylated to acetyl-CoA by the breakdown of <a href="/wiki/Carbohydrates" class="mw-redirect" title="Carbohydrates">carbohydrates</a> through <a href="/wiki/Glycolysis" title="Glycolysis">glycolysis</a> and by the breakdown of <a href="/wiki/Fatty_acids" class="mw-redirect" title="Fatty acids">fatty acids</a> through <a href="/wiki/Beta_oxidation" title="Beta oxidation">β-oxidation</a>. Acetyl-CoA then enters the citric acid cycle, where the acetyl group is oxidized to carbon dioxide and water, and the energy released is captured in the form of 11 <a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a> and one <a href="/wiki/Guanosine_triphosphate" title="Guanosine triphosphate">GTP</a> per acetyl group. </p><p><a href="/wiki/Konrad_Bloch" class="mw-redirect" title="Konrad Bloch">Konrad Bloch</a> and <a href="/wiki/Feodor_Lynen" title="Feodor Lynen">Feodor Lynen</a> were awarded the 1964 <a href="/wiki/Nobel_Prize_in_Physiology_or_Medicine" title="Nobel Prize in Physiology or Medicine">Nobel Prize in Physiology or Medicine</a> for their discoveries linking acetyl-CoA and fatty acid metabolism. <a href="/wiki/Fritz_Lipmann" class="mw-redirect" title="Fritz Lipmann">Fritz Lipmann</a> won the Nobel Prize in 1953 for his discovery of the cofactor <a href="/wiki/Coenzyme_A" title="Coenzyme A">coenzyme A</a>.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Role">Role</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetyl-CoA&action=edit&section=1" title="Edit section: Role"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Acetyl-CoA is a <a href="/wiki/Metabolic_intermediate" title="Metabolic intermediate">metabolic intermediate</a> that is involved in many metabolic pathways in an organism. It is produced during the breakdown of <a href="/wiki/Glucose" title="Glucose">glucose</a>, <a href="/wiki/Fatty_acids" class="mw-redirect" title="Fatty acids">fatty acids</a>, and <a href="/wiki/Amino_acid" title="Amino acid">amino acids</a>, and is used in the synthesis of many other <a href="/wiki/Biomolecules" class="mw-redirect" title="Biomolecules">biomolecules</a>, including <a href="/wiki/Cholesterol" title="Cholesterol">cholesterol</a>, <a href="/wiki/Fatty_acid" title="Fatty acid">fatty acids</a>, and <a href="/wiki/Ketone_bodies" title="Ketone bodies">ketone bodies</a>. Acetyl-CoA is also a key molecule in the <a href="/wiki/Citric_acid_cycle" title="Citric acid cycle">citric acid cycle</a>, which is a series of chemical reactions that occur in the <a href="/wiki/Mitochondrion" title="Mitochondrion">mitochondria</a> of cells and is responsible for generating energy in the form of <a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a>.<sup id="cite_ref-pmid31387584_5-0" class="reference"><a href="#cite_note-pmid31387584-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>In addition, acetyl-CoA is a precursor for the biosynthesis of various acetyl-chemicals, acting as an intermediate to transfer an acetyl group during the biosynthesis of those acetyl-chemicals. Acetyl-CoA is also involved in the regulation of various cellular mechanisms by providing acetyl groups to target amino acid residues for post-translational <a href="/wiki/Acetylation" title="Acetylation">acetylation</a> reactions of proteins. </p> <div class="mw-heading mw-heading2"><h2 id="Biosynthesis">Biosynthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetyl-CoA&action=edit&section=2" title="Edit section: Biosynthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The acetylation of CoA is determined by the carbon sources.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Extramitochondrial">Extramitochondrial</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetyl-CoA&action=edit&section=3" title="Edit section: Extramitochondrial"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>At high <a href="/wiki/Glucose" title="Glucose">glucose</a> levels, <a href="/wiki/Glycolysis" title="Glycolysis">glycolysis</a> takes place rapidly, thus increasing the amount of <a href="/wiki/Citrate" class="mw-redirect" title="Citrate">citrate</a> produced from the <a href="/wiki/Citric_acid_cycle" title="Citric acid cycle">citric acid cycle</a>. This citrate is then exported to other <a href="/wiki/Organelle" title="Organelle">organelles</a> outside the mitochondria to be broken into acetyl-CoA and <a href="/wiki/Oxaloacetate" class="mw-redirect" title="Oxaloacetate">oxaloacetate</a> by the <a href="/wiki/Enzyme" title="Enzyme">enzyme</a> <a href="/wiki/ATP_citrate_lyase" class="mw-redirect" title="ATP citrate lyase">ATP citrate lyase</a> (ACL). This principal reaction is coupled with the <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolysis</a> of ATP.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup></li> <li>At low glucose levels: <ul><li>CoA is acetylated using <a href="/wiki/Acetate" title="Acetate">acetate</a> by <a href="/wiki/Acetyl-CoA_synthetase" title="Acetyl-CoA synthetase">acetyl-CoA synthetase</a> (ACS), also coupled with <a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a> hydrolysis.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Ethanol" title="Ethanol">Ethanol</a> also serves as a carbon source for acetylation of CoA utilizing the enzyme <a href="/wiki/Alcohol_dehydrogenase" title="Alcohol dehydrogenase">alcohol dehydrogenase</a>.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup></li> <li>Degradation of branched-chain <a href="/wiki/Ketogenic" class="mw-redirect" title="Ketogenic">ketogenic</a> <a href="/wiki/Amino_acid" title="Amino acid">amino acids</a> such as <a href="/wiki/Valine" title="Valine">valine</a>, <a href="/wiki/Leucine" title="Leucine">leucine</a>, and <a href="/wiki/Isoleucine" title="Isoleucine">isoleucine</a> occurs. These amino acids are converted to α-ketoacids by <a href="/wiki/Transamination" title="Transamination">transamination</a> and eventually to <a href="/wiki/Isovaleryl-CoA" title="Isovaleryl-CoA">isovaleryl-CoA</a> through oxidative decarboxylation by an α-ketoacid dehydrogenase complex. Isovaleryl-CoA undergoes <a href="/wiki/Dehydrogenation" title="Dehydrogenation">dehydrogenation</a>, <a href="/wiki/Carboxylation" title="Carboxylation">carboxylation</a> and hydration to form another CoA-derivative intermediate before it is cleaved into acetyl-CoA and <a href="/wiki/Acetoacetate" class="mw-redirect" title="Acetoacetate">acetoacetate</a>.<sup id="cite_ref-:0_13-0" class="reference"><a href="#cite_note-:0-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citing_sources" title="Wikipedia:Citing sources"><span title="This citation requires a reference to the specific page or range of pages in which the material appears. (August 2017)">page needed</span></a></i>]</sup></li></ul></li></ul> <div class="mw-heading mw-heading3"><h3 id="Intramitochondrial">Intramitochondrial</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetyl-CoA&action=edit&section=4" title="Edit section: Intramitochondrial"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Pyruvate_dehydrogenase_complex_reaction.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/47/Pyruvate_dehydrogenase_complex_reaction.svg/220px-Pyruvate_dehydrogenase_complex_reaction.svg.png" decoding="async" width="220" height="101" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/47/Pyruvate_dehydrogenase_complex_reaction.svg/330px-Pyruvate_dehydrogenase_complex_reaction.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/47/Pyruvate_dehydrogenase_complex_reaction.svg/440px-Pyruvate_dehydrogenase_complex_reaction.svg.png 2x" data-file-width="813" data-file-height="374" /></a><figcaption><a href="/wiki/Pyruvate_dehydrogenase" title="Pyruvate dehydrogenase">Pyruvate dehydrogenase</a> complex reaction</figcaption></figure> <ul><li>At high glucose levels, acetyl-CoA is produced through <a href="/wiki/Glycolysis" title="Glycolysis">glycolysis</a>.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Pyruvate" class="mw-redirect" title="Pyruvate">Pyruvate</a> undergoes oxidative decarboxylation in which it loses its <a href="/wiki/Carboxyl" class="mw-redirect" title="Carboxyl">carboxyl</a> group (as <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a>) to form acetyl-CoA, giving off 33.5 kJ/mol of energy. The oxidative conversion of pyruvate into acetyl-CoA is referred to as the <b>pyruvate dehydrogenase reaction</b>. It is catalyzed by the <a href="/wiki/Pyruvate_dehydrogenase_complex" title="Pyruvate dehydrogenase complex">pyruvate dehydrogenase complex</a>. Other conversions between pyruvate and acetyl-CoA are possible. For example, <a href="/wiki/Pyruvate_formate_lyase" class="mw-redirect" title="Pyruvate formate lyase">pyruvate formate lyase</a> <a href="/wiki/Disproportionates" class="mw-redirect" title="Disproportionates">disproportionates</a> pyruvate into acetyl-CoA and <a href="/wiki/Formic_acid" title="Formic acid">formic acid</a>.</li></ul> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Metabolism4.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/77/Metabolism4.jpg/282px-Metabolism4.jpg" decoding="async" width="282" height="199" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/77/Metabolism4.jpg/423px-Metabolism4.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/77/Metabolism4.jpg/564px-Metabolism4.jpg 2x" data-file-width="2000" data-file-height="1412" /></a><figcaption><a href="/wiki/Beta-oxidation" class="mw-redirect" title="Beta-oxidation">β-Oxidation</a> of <a href="/wiki/Fatty_acid" title="Fatty acid">fatty acids</a></figcaption></figure> <ul><li>At low glucose levels, the production of acetyl-CoA is linked to <a href="/wiki/Beta_oxidation" title="Beta oxidation">β-oxidation</a> of <a href="/wiki/Fatty_acid" title="Fatty acid">fatty acids</a>. Fatty acids are first converted to acyl-CoA. Acyl-CoA is then degraded in a four-step cycle of <a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">oxidation</a>, <a href="/wiki/Hydration_reaction" title="Hydration reaction">hydration</a>, <a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">oxidation</a> and <a href="/wiki/Thiolysis" title="Thiolysis">thiolysis</a> catalyzed by four respective enzymes, namely <a href="/wiki/Acyl-CoA_dehydrogenase" title="Acyl-CoA dehydrogenase">acyl-CoA dehydrogenase</a>, <a href="/wiki/Enoyl-CoA_hydratase" title="Enoyl-CoA hydratase">enoyl-CoA hydratase</a>, <a href="/wiki/3-hydroxyacyl-CoA_dehydrogenase" title="3-hydroxyacyl-CoA dehydrogenase">3-hydroxyacyl-CoA dehydrogenase</a>, and <a href="/wiki/Thiolase" title="Thiolase">thiolase</a>. The cycle produces a new fatty acid chain with two fewer carbons and acetyl-CoA as a byproduct.<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup></li></ul> <div class="mw-heading mw-heading2"><h2 id="Functions">Functions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetyl-CoA&action=edit&section=5" title="Edit section: Functions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Intermediates_in_various_pathways">Intermediates in various pathways</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetyl-CoA&action=edit&section=6" title="Edit section: Intermediates in various pathways"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>In <a href="/wiki/Cellular_respiration" title="Cellular respiration">cellular respiration</a></li> <li><a href="/wiki/Citric_acid_cycle" title="Citric acid cycle">Citric acid cycle</a>: <ul><li>Through a series of chemical reactions, stored energy is released through the oxidation of acetyl-CoA derived from carbohydrates, fats, and proteins into <a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">adenosine triphosphate</a> (ATP) and <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a>.</li></ul></li> <li><a href="/wiki/Fatty_acid_metabolism" title="Fatty acid metabolism">Fatty acid metabolism</a> <ul><li>Acetyl-CoA is produced by the breakdown of both <a href="/wiki/Carbohydrate" title="Carbohydrate">carbohydrates</a> (by <a href="/wiki/Glycolysis" title="Glycolysis">glycolysis</a>) and <a href="/wiki/Lipids" class="mw-redirect" title="Lipids">lipids</a> (by <a href="/wiki/Beta_oxidation" title="Beta oxidation">β-oxidation</a>). It then enters the citric acid cycle in the mitochondrion by combining with <a href="/wiki/Oxaloacetic_acid" title="Oxaloacetic acid">oxaloacetate</a> to form <a href="/wiki/Citric_acid" title="Citric acid">citrate</a>.<sup id="cite_ref-stryer2_16-0" class="reference"><a href="#cite_note-stryer2-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-oxidation_of_fats_17-0" class="reference"><a href="#cite_note-oxidation_of_fats-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup></li> <li>Two acetyl-CoA molecules condense to form <a href="/wiki/Acetoacetyl-CoA" title="Acetoacetyl-CoA">acetoacetyl-CoA</a>, which gives rise to the formation of <a href="/wiki/Acetoacetic_acid" title="Acetoacetic acid">acetoacetate</a> and <a href="/wiki/Beta-Hydroxybutyric_acid" class="mw-redirect" title="Beta-Hydroxybutyric acid">β-hydroxybutyrate</a>.<sup id="cite_ref-stryer2_16-1" class="reference"><a href="#cite_note-stryer2-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> Acetoacetate, β-hydroxybutyrate, and their spontaneous breakdown product <a href="/wiki/Acetone" title="Acetone">acetone</a><sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> are frequently, but confusingly, known as <a href="/wiki/Ketone_bodies" title="Ketone bodies">ketone bodies</a> (as they are not "bodies" at all, but water-soluble chemical substances). The ketone bodies are released by the <a href="/wiki/Liver" title="Liver">liver</a> into the blood. All cells with mitochondria can take ketone bodies up from the blood and reconvert them into acetyl-CoA, which can then be used as fuel in their citric acid cycles, as no other tissue can divert its oxaloacetate into the <a href="/wiki/Gluconeogenesis" title="Gluconeogenesis">gluconeogenic pathway</a> in the way that the liver does. Unlike free fatty acids, ketone bodies can cross the <a href="/wiki/Blood%E2%80%93brain_barrier" title="Blood–brain barrier">blood–brain barrier</a> and are therefore available as fuel for the cells of the <a href="/wiki/Central_nervous_system" title="Central nervous system">central nervous system</a>, acting as a substitute for glucose, on which these cells normally survive.<sup id="cite_ref-stryer2_16-2" class="reference"><a href="#cite_note-stryer2-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> The occurrence of high levels of ketone bodies in the blood during <a href="/wiki/Starvation" title="Starvation">starvation</a>, a <a href="/wiki/Low-carbohydrate_diet" title="Low-carbohydrate diet">low-carbohydrate diet</a>, prolonged heavy exercise, and uncontrolled <a href="/wiki/Type_1_diabetes" title="Type 1 diabetes">type-1 diabetes mellitus</a> is known as <a href="/wiki/Ketosis" title="Ketosis">ketosis</a>, and in its extreme form in out-of-control type-1 diabetes mellitus, as <a href="/wiki/Ketoacidosis" title="Ketoacidosis">ketoacidosis</a>.</li> <li>On the other hand, when the <a href="/wiki/Insulin" title="Insulin">insulin</a> concentration in the blood is high, and that of <a href="/wiki/Glucagon" title="Glucagon">glucagon</a> is low (i.e. after meals), the acetyl-CoA produced by glycolysis condenses as normal with oxaloacetate to form citrate in the mitochondrion. However, instead of continuing through the citric acid cycle to be converted to carbon dioxide and water, the citrate is removed from the mitochondrion into the <a href="/wiki/Cytoplasm" title="Cytoplasm">cytoplasm</a>.<sup id="cite_ref-stryer2_16-3" class="reference"><a href="#cite_note-stryer2-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> There it is cleaved by <a href="/wiki/ATP_citrate_lyase" class="mw-redirect" title="ATP citrate lyase">ATP citrate lyase</a> into acetyl-CoA and oxaloacetate. The oxaloacetate is returned to the mitochondrion as malate (and then converted back into oxaloacetate to transfer more acetyl-CoA out of the mitochondrion).<sup id="cite_ref-ferre_19-0" class="reference"><a href="#cite_note-ferre-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> This cytosolic acetyl-CoA can then be used to synthesize fatty acids through carboxylation by <a href="/wiki/Acetyl-CoA_carboxylase" title="Acetyl-CoA carboxylase">acetyl-CoA carboxylase</a> into <a href="/wiki/Malonyl-CoA" title="Malonyl-CoA">malonyl CoA</a>, the first committed step in the synthesis of fatty acids.<sup id="cite_ref-ferre_19-1" class="reference"><a href="#cite_note-ferre-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Voet_20-0" class="reference"><a href="#cite_note-Voet-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> This conversion occurs primarily in the liver, <a href="/wiki/Adipose_tissue" title="Adipose tissue">adipose tissue</a> and lactating <a href="/wiki/Mammary_gland" title="Mammary gland">mammary glands</a>, where the fatty acids are combined with <a href="/wiki/Glycerol" title="Glycerol">glycerol</a> to form <a href="/wiki/Triglyceride" title="Triglyceride">triglycerides</a>, the major fuel reservoir of most animals. Fatty acids are also components of the <a href="/wiki/Phospholipid" title="Phospholipid">phospholipids</a> that make up the bulk of the <a href="/wiki/Lipid_bilayer" title="Lipid bilayer">lipid bilayers</a> of all <a href="/wiki/Cellular_membrane" class="mw-redirect" title="Cellular membrane">cellular membranes</a>.<sup id="cite_ref-stryer2_16-4" class="reference"><a href="#cite_note-stryer2-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup></li> <li>In plants, <i>de novo</i> fatty acid synthesis occurs in the <a href="/wiki/Plastid" title="Plastid">plastids</a>. Many <a href="/wiki/Seed" title="Seed">seeds</a> accumulate large reservoirs of seed oils to support <a href="/wiki/Germination" title="Germination">germination</a> and early growth of the seedling before it is a net <a href="/wiki/Photosynthesis" title="Photosynthesis">photosynthetic</a> organism.</li> <li>The <a href="/wiki/Cytosol" title="Cytosol">cytosolic</a> acetyl-CoA can also condense with <a href="/wiki/Acetoacetyl-CoA" title="Acetoacetyl-CoA">acetoacetyl-CoA</a> to form 3-hydroxy-3-methylglutaryl-CoA (<a href="/wiki/HMG-CoA" title="HMG-CoA">HMG-CoA</a>) which is the rate-limiting step controlling the <a href="/wiki/Mevalonate_pathway" title="Mevalonate pathway">synthesis of cholesterol</a>.<sup id="cite_ref-stryer2_16-5" class="reference"><a href="#cite_note-stryer2-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a> can be used as is, as a structural component of cellular membranes, or it can be used to synthesize <a href="/wiki/Steroid#Steroidogenesis" title="Steroid">steroid hormones</a>, <a href="/wiki/Bile_acids" class="mw-redirect" title="Bile acids">bile salts</a>, and <a href="/wiki/Vitamin_D" title="Vitamin D">vitamin D</a>.<sup id="cite_ref-stryer2_16-6" class="reference"><a href="#cite_note-stryer2-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Voet_20-1" class="reference"><a href="#cite_note-Voet-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup></li> <li>Acetyl-CoA can be <a href="/wiki/Carboxylated" class="mw-redirect" title="Carboxylated">carboxylated</a> in the cytosol by <a href="/wiki/Acetyl-CoA_carboxylase" title="Acetyl-CoA carboxylase">acetyl-CoA carboxylase</a>, giving rise to <a href="/wiki/Malonyl-CoA" title="Malonyl-CoA">malonyl-CoA</a>, a substrate required for synthesis of <a href="/wiki/Flavonoid" title="Flavonoid">flavonoids</a> and related <a href="/wiki/Polyketide" title="Polyketide">polyketides</a>, for elongation of fatty acids to produce <a href="/wiki/Wax" title="Wax">waxes</a>, <a href="/wiki/Cuticle" title="Cuticle">cuticle</a>, and seed oils in members of the <a href="/wiki/Brassica" title="Brassica">Brassica</a> family, and for <a href="/wiki/Malonate" class="mw-redirect" title="Malonate">malonation</a> of proteins and other phytochemicals.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> In plants, these include <a href="/wiki/Sesquiterpene" title="Sesquiterpene">sesquiterpenes</a>, <a href="/wiki/Brassinosteroid" title="Brassinosteroid">brassinosteroids</a> (hormones), and membrane <a href="/wiki/Sterol" title="Sterol">sterols</a>.</li></ul></li> <li><a href="/wiki/Steroid_synthesis" class="mw-redirect" title="Steroid synthesis">Steroid synthesis</a>: <ul><li>Acetyl-CoA participates in the <a href="/wiki/Mevalonate_pathway" title="Mevalonate pathway">mevalonate pathway</a> by partaking in the synthesis of hydroxymethyl glutaryl-CoA.</li></ul></li> <li><a href="/wiki/Acetylcholine" title="Acetylcholine">Acetylcholine</a> synthesis: <ul><li>Acetyl-CoA is also an important component in the biogenic synthesis of the <a href="/wiki/Neurotransmitter" title="Neurotransmitter">neurotransmitter</a> <a href="/wiki/Acetylcholine" title="Acetylcholine">acetylcholine</a>. <a href="/wiki/Choline" title="Choline">Choline</a>, in combination with acetyl-CoA, is catalyzed by the enzyme <a href="/wiki/Choline_acetyltransferase" title="Choline acetyltransferase">choline acetyltransferase</a> to produce acetylcholine and <a href="/wiki/Coenzyme_A" title="Coenzyme A">coenzyme A</a> as a byproduct.</li></ul></li> <li><a href="/wiki/Melatonin" title="Melatonin">Melatonin</a> synthesis</li> <li>Acetylation <ul><li>Acetyl-CoA is also the source of the acetyl group incorporated onto certain <a href="/wiki/Lysine" title="Lysine">lysine</a> residues of <a href="/wiki/Histone" title="Histone">histone</a> and nonhistone proteins in the <a href="/wiki/Posttranslational_modification" class="mw-redirect" title="Posttranslational modification">posttranslational modification</a> <a href="/wiki/Acetylation" title="Acetylation">acetylation</a>. This acetylation is catalyzed by <a href="/wiki/Acetyltransferases" class="mw-redirect" title="Acetyltransferases">acetyltransferases</a>. This acetylation affects <a href="/wiki/Cell_growth" title="Cell growth">cell growth</a>, <a href="/wiki/Mitosis" title="Mitosis">mitosis</a>, and <a href="/wiki/Apoptosis" title="Apoptosis">apoptosis</a>.<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup></li></ul></li> <li>Allosteric regulator <ul><li>Acetyl-CoA serves as an <a href="/wiki/Allosteric_regulation" title="Allosteric regulation">allosteric regulator</a> of <a href="/wiki/Pyruvate_dehydrogenase_kinase" title="Pyruvate dehydrogenase kinase">pyruvate dehydrogenase kinase</a> (PDK). It regulates through the ratio of acetyl-CoA versus CoA. Increased concentration of acetyl-CoA activates PDK.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup></li> <li>Acetyl-CoA is also an allosteric activator of <a href="/wiki/Pyruvate_carboxylase" title="Pyruvate carboxylase">pyruvate carboxylase</a>.<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup></li></ul></li></ul> <div class="mw-heading mw-heading2"><h2 id="Interactive_pathway_map">Interactive pathway map</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetyl-CoA&action=edit&section=7" title="Edit section: Interactive pathway map"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><i>Click on genes, proteins and metabolites below to visit <a href="/wiki/Portal:Gene_Wiki" class="mw-redirect" title="Portal:Gene Wiki">Gene Wiki</a> pages and related Wikipedia articles. The pathway can be downloaded and edited at <a rel="nofollow" class="external text" href="http://www.wikipathways.org">WikiPathways</a>.</i> </p> <table style="margin-left: auto; margin-right: auto; border: none;"> <tbody><tr> <td width="390px"> <div style="overflow:auto;"> <div class="thumb tleft"> <div class="thumbinner" style="width: 377px;"> <div class="thumbimage" style="width: 375px; height: 350px; overflow: hidden;"> <div style="position: relative; top: -62.5px; left: -117.157414151063px; width: {{{bSize}}}px"><div class="noresize">[[File:<div class="noresize thumb tnone" style=";"> <div class="thumbinner" style="overflow:hidden;width:977px;"> <div class="thumbimage" style="overflow:hidden; position:relative; background-color:white;"> <div style=";left:0px; top:0px; width:975px; position:absolute;"> <figure class="mw-default-size mw-halign-right noresize" typeof="mw:File"><a href="#Interactive_pathway_map" title="Go to pathway article"><img alt="TCACycle_WP78" 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style="position:absolute; left:0px; top:0px; line-height:110%;"><span style="background-color:transparent; color:inherit;">[[<div style="display:block; width:80px; height:0px; overflow:hidden; position:relative; left:348.2px; top:670.8px; background:transparent; border-top:3px blue solid"></div>]]</span></div> <div id="annotation_0x0" style="position:absolute; left:0px; top:0px; line-height:110%;"><span style="background-color:transparent; color:inherit;">[[<div style="display:block; width:80px; height:0px; overflow:hidden; position:relative; left:348.2px; top:690.8px; background:transparent; border-top:3px blue solid"></div>]]</span></div> <div id="annotation_0x0" style="position:absolute; left:0px; top:0px; line-height:110%;"><span style="background-color:transparent; color:inherit;">[[<div style="display:block; width:58px; height:12px; overflow:hidden; position:relative; left:50.3px; top:59px; background:transparent; border:4px black solid"></div>]] </span></div> </div> <div style="visibility:hidden"><figure class="mw-default-size mw-halign-right noresize" typeof="mw:File"><a href="/wiki/Statin#Other_effects" title="Go to pathway article"><img alt="Statin_Pathway_WP430" src="//upload.wikimedia.org/wikipedia/commons/f/f6/StatinPathway_WP430.png" decoding="async" width="828" height="743" class="mw-file-element" data-file-width="828" data-file-height="743" usemap="#ImageMap_fd82d813802fabd6" /></a><map name="ImageMap_fd82d813802fabd6"><area href="/wiki/HMGCR" shape="rect" coords="129,126,189,146" alt="go to article" title="go to article" /><area href="/wiki/CYP7A1" shape="rect" coords="348,151,399,171" alt="go to article" title="go to article" /><area href="/wiki/SOAT1" shape="rect" coords="396,185,456,205" alt="go to article" title="go to article" /><area href="/wiki/Dgat1" shape="rect" coords="664,142,724,162" alt="go to article" title="go to article" /><area href="/wiki/LDL_receptor" shape="rect" coords="159,315,219,335" alt="go to article" title="go to article" /><area href="/wiki/SCARB1" shape="rect" coords="446,318,506,338" alt="go to article" title="go to article" /><area href="/wiki/LRP1" shape="rect" coords="288,315,348,335" alt="go to article" title="go to article" /><area href="/wiki/Lipoprotein_lipase" shape="rect" coords="359,344,419,364" alt="go to article" title="go to article" /><area href="/wiki/Hepatic_lipase" shape="rect" coords="207,398,267,418" alt="go to article" title="go to article" /><area href="/wiki/Cholesterylester_transfer_protein" shape="rect" coords="281,436,341,456" alt="go to article" title="go to article" /><area href="/wiki/Lecithin-cholesterol_acyltransferase" shape="rect" coords="303,494,363,514" alt="go to article" title="go to article" /><area href="/wiki/ABCA1" shape="rect" coords="304,606,364,626" alt="go to article" title="go to article" /><area href="/wiki/Apolipoprotein_A1" shape="rect" coords="522,451,582,471" alt="go to article" title="go to article" /><area href="/wiki/APOA4" shape="rect" coords="468,536,528,556" alt="go to article" title="go to article" /><area href="/wiki/APOC1" shape="rect" coords="609,420,669,440" alt="go to article" title="go to article" /><area href="/wiki/Apolipoprotein_E" shape="rect" coords="609,400,669,420" alt="go to article" title="go to article" /><area href="/wiki/APOC2" shape="rect" coords="669,400,729,420" alt="go to article" title="go to article" /><area href="/wiki/Apolipoprotein_C3" shape="rect" coords="669,420,729,440" alt="go to article" title="go to article" /><area href="/wiki/PLTP" shape="rect" coords="522,431,582,451" alt="go to article" title="go to article" /><area href="/wiki/Cholesterol" shape="rect" coords="268,219,362,238" alt="go to article" title="go to article" /><area href="/wiki/Cholic_acid" shape="rect" coords="281,104,350,123" alt="go to article" title="go to article" /><area href="/wiki/Cholesterol" shape="rect" coords="194,620,263,639" alt="go to article" title="go to article" /><area href="/wiki/Acetyl-coa" shape="rect" coords="50,71,115,91" alt="go to article" title="go to article" /><area href="/wiki/Cholesteryl_ester" shape="rect" coords="470,218,555,238" alt="go to article" title="go to article" /><area href="/wiki/Fatty_acid" shape="rect" coords="411,114,466,134" alt="go to article" title="go to article" /><area href="/wiki/Phospholipid" shape="rect" coords="559,194,634,214" alt="go to article" title="go to article" /><area href="/wiki/Triglyceride" shape="rect" coords="655,230,735,250" alt="go to article" title="go to article" /><area href="/wiki/LDL" shape="rect" coords="135,362,167,382" alt="go to article" title="go to article" /><area href="/wiki/Intermediate_density_lipoprotein" shape="rect" coords="299,362,331,382" alt="go to article" title="go to article" /><area href="/wiki/VLDL" shape="rect" coords="415,383,447,403" alt="go to article" title="go to article" /><area href="/wiki/High-density_lipoprotein" shape="rect" coords="386,447,418,467" alt="go to article" title="go to article" /><area href="/wiki/ABCG5" shape="rect" coords="125,555,185,575" alt="go to article" title="go to article" /><area href="/wiki/ABCG8" shape="rect" coords="125,575,185,595" alt="go to article" title="go to article" /><area href="/wiki/ABCA1" shape="rect" coords="413,605,473,625" alt="go to article" title="go to article" /><area href="/wiki/Cholesterol" shape="rect" coords="509,622,577,641" alt="go to article" title="go to article" /><area href="/wiki/Apolipoprotein_B" shape="rect" coords="609,440,669,460" alt="go to article" title="go to article" /><area href="/wiki/APOA5" shape="rect" coords="669,440,729,460" alt="go to article" title="go to article" /><area href="/wiki/Microsomal_triglyceride_transfer_protein" shape="rect" coords="572,314,621,334" alt="go to article" title="go to article" /><area href="/wiki/Diglyceride" shape="rect" coords="583,96,629,116" alt="go to article" title="go to article" /><area href="/wiki/Squalene" shape="rect" coords="127,218,194,238" alt="go to article" title="go to article" /><area href="/wiki/Farnesyl-diphosphate_farnesyltransferase" shape="rect" coords="40,245,91,265" alt="go to article" title="go to article" /><area href="/wiki/Squalene_monooxygenase" shape="rect" coords="202,181,245,201" alt="go to article" title="go to article" /><area href="/wiki/Acyl-CoA" shape="rect" coords="498,114,552,134" alt="go to article" title="go to article" /><area href="/wiki/Acyl-CoA_synthetase" shape="rect" coords="431,76,533,96" alt="go to article" title="go to article" /><area href="/wiki/Protein_disulfide-isomerase" shape="rect" coords="572,294,621,314" alt="go to article" title="go to article" /><area href="/wiki/Cholesterol" shape="rect" coords="359,541,428,560" alt="go to article" title="go to article" /><area href="/wiki/APOA2" shape="rect" coords="522,471,582,491" alt="go to article" title="go to article" /><area href="/wiki/MiR-33" shape="rect" coords="348,666,428,686" alt="go to article" title="go to article" /><area href="/wiki/MiR-33" shape="rect" coords="348,686,428,706" alt="go to article" title="go to article" /></map><figcaption></figcaption></figure></div> </div> <div class="thumbcaption"></div> </div></div>|alt=Statin pathway <a rel="nofollow" class="external text" href="http://www.wikipathways.org/index.php/Pathway:WP430">edit</a>]]</div></div> </div> <div class="thumbcaption"> <div class="magnify"><a href="/wiki/File:StatinPathway_WP430.png" title="File:StatinPathway WP430.png"> </a></div>Statin pathway <a rel="nofollow" class="external text" href="http://www.wikipathways.org/index.php/Pathway:WP430">edit</a> </div> </div> </div> <div style="clear:both;" class=""></div><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239543626"><div class="reflist"> </div> </div> </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetyl-CoA&action=edit&section=8" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Malonyl-CoA_decarboxylase" title="Malonyl-CoA decarboxylase">Malonyl-CoA decarboxylase</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetyl-CoA&action=edit&section=9" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239543626"><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-lamda_source_1-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-lamda_source_1_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-lamda_source_1_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-lamda_source_1_1-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-lamda_source_1_1-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFDawsonElliottElliottJones2002" class="citation book cs1">Dawson RM, Elliott DC, Elliott WH, Jones KM (2002). <i>Data for Biochemical Research</i> (3rd ed.). Clarendon Press. p. 117. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-19-855299-4" title="Special:BookSources/978-0-19-855299-4"><bdi>978-0-19-855299-4</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Data+for+Biochemical+Research&rft.pages=117&rft.edition=3rd&rft.pub=Clarendon+Press&rft.date=2002&rft.isbn=978-0-19-855299-4&rft.aulast=Dawson&rft.aufirst=Rex+M.+C.&rft.au=Elliott%2C+Daphne+C.&rft.au=Elliott%2C+William+H.&rft.au=Jones%2C+Kenneth+M.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetyl-CoA" class="Z3988"></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20161115202146/http://chemistry.elmhurst.edu/vchembook/623acetylCoAfate.html">"Acetyl CoA Crossroads"</a>. <i>chemistry.elmhurst.edu</i>. 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Butterworth-Heinemann. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9781483183671" title="Special:BookSources/9781483183671"><bdi>9781483183671</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Guide+to+Biochemistry&rft.pub=Butterworth-Heinemann&rft.date=2014-06-28&rft.isbn=9781483183671&rft.aulast=Blackstock&rft.aufirst=James+C.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dy8JQAwAAQBAJ%26q%3Dacetyl%2BcoA%2Bpathway%26pg%3DPA149&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetyl-CoA" class="Z3988"></span></span> </li> <li id="cite_note-15"><span class="mw-cite-backlink"><b><a href="#cite_ref-15">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHoutenWanders2010" class="citation journal cs1">Houten SM, Wanders RJ (2010-03-02). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2950079">"A general introduction to the biochemistry of mitochondrial fatty acid β-oxidation"</a>. <i>Journal of Inherited Metabolic Disease</i>. <b>33</b> (5): 469–477. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2Fs10545-010-9061-2">10.1007/s10545-010-9061-2</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0141-8955">0141-8955</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2950079">2950079</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/20195903">20195903</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Inherited+Metabolic+Disease&rft.atitle=A+general+introduction+to+the+biochemistry+of+mitochondrial+fatty+acid+%CE%B2-oxidation&rft.volume=33&rft.issue=5&rft.pages=469-477&rft.date=2010-03-02&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2950079%23id-name%3DPMC&rft.issn=0141-8955&rft_id=info%3Apmid%2F20195903&rft_id=info%3Adoi%2F10.1007%2Fs10545-010-9061-2&rft.aulast=Houten&rft.aufirst=Sander+Michel&rft.au=Wanders%2C+Ronald+J.+A.&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2950079&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetyl-CoA" class="Z3988"></span></span> </li> <li id="cite_note-stryer2-16"><span class="mw-cite-backlink">^ <a href="#cite_ref-stryer2_16-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-stryer2_16-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-stryer2_16-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-stryer2_16-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-stryer2_16-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-stryer2_16-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-stryer2_16-6"><sup><i><b>g</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFStryer1995" class="citation book cs1">Stryer L (1995). <i>Biochemistry</i> (Fourth ed.). 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University of Waterloo.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Ketone+body+metabolism&rft.pub=University+of+Waterloo&rft_id=http%3A%2F%2Fwatcut.uwaterloo.ca%2Fwebnotes%2FMetabolism%2FfatKetoneBodyMetabolism.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetyl-CoA" class="Z3988"></span></span> </li> <li id="cite_note-ferre-19"><span class="mw-cite-backlink">^ <a href="#cite_ref-ferre_19-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-ferre_19-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFerreF._Foufelle2007" class="citation journal cs1">Ferre P, F. Foufelle (2007). "SREBP-1c Transcription Factor and Lipid Homeostasis: Clinical Perspective". <i>Hormone Research</i>. <b>68</b> (2): 72–82. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1159%2F000100426">10.1159/000100426</a></span> (inactive 1 November 2024). <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/17344645">17344645</a>. <q>this process is outlined graphically in page 73</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Hormone+Research&rft.atitle=SREBP-1c+Transcription+Factor+and+Lipid+Homeostasis%3A+Clinical+Perspective&rft.volume=68&rft.issue=2&rft.pages=72-82&rft.date=2007&rft_id=info%3Adoi%2F10.1159%2F000100426&rft_id=info%3Apmid%2F17344645&rft.aulast=Ferre&rft.aufirst=P.&rft.au=F.+Foufelle&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetyl-CoA" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: DOI inactive as of November 2024 (<a href="/wiki/Category:CS1_maint:_DOI_inactive_as_of_November_2024" title="Category:CS1 maint: DOI inactive as of November 2024">link</a>)</span></span> </li> <li id="cite_note-Voet-20"><span class="mw-cite-backlink">^ <a href="#cite_ref-Voet_20-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Voet_20-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFVoetJudith_G._VoetCharlotte_W._Pratt2006" class="citation book cs1">Voet D, Judith G. 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title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Biochemical+and+Biophysical+Research+Communications&rft.atitle=Regulation+of+pyruvate+dehydrogenase+kinase+and+phosphatase+by+acetyl-CoA%2FCoA+and+NADH%2FNAD+ratios&rft.volume=65&rft.issue=2&rft.pages=575-582&rft.date=1975-07-22&rft_id=info%3Adoi%2F10.1016%2FS0006-291X%2875%2980185-9&rft_id=info%3Apmid%2F167775&rft.aulast=Pettit&rft.aufirst=Flora+H.&rft.au=Pelley%2C+John+W.&rft.au=Reed%2C+Lester+J.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetyl-CoA" class="Z3988"></span></span> </li> <li id="cite_note-24"><span class="mw-cite-backlink"><b><a href="#cite_ref-24">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJitrapakdeeMauriceRaymentCleland2008" class="citation journal cs1">Jitrapakdee S, Maurice MS, <a href="/wiki/Ivan_Rayment" title="Ivan Rayment">Rayment I</a>, Cleland WW, Wallace 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rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/18613815">18613815</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Biochemical+Journal&rft.atitle=Structure%2C+Mechanism+and+Regulation+of+Pyruvate+Carboxylase&rft.volume=413&rft.issue=3&rft.pages=369-387&rft.date=2008-08-01&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2859305%23id-name%3DPMC&rft.issn=0264-6021&rft_id=info%3Apmid%2F18613815&rft_id=info%3Adoi%2F10.1042%2FBJ20080709&rft.aulast=Jitrapakdee&rft.aufirst=Sarawut&rft.au=Maurice%2C+Martin+St.&rft.au=Rayment%2C+Ivan&rft.au=Cleland%2C+W.+Wallace&rft.au=Wallace%2C+John+C.&rft.au=Attwood%2C+Paul+V.&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2859305&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetyl-CoA" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetyl-CoA&action=edit&section=10" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" href="https://meshb.nlm.nih.gov/record/ui?name=Acetyl+Coenzyme+A">Acetyl+Coenzyme+A</a> at the U.S. National Library of Medicine <a href="/wiki/Medical_Subject_Headings" title="Medical Subject Headings">Medical Subject Headings</a> (MeSH)</li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist 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</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Degradation</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acyl-CoA" title="Acyl-CoA">Acyl-CoA</a></li> <li><a class="mw-selflink selflink">Acetyl-CoA</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Peroxisome" title="Peroxisome">Peroxisomal</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phytol" title="Phytol">Phytol</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Phytanic_acid" title="Phytanic acid">Phytanic acid</a></li> <li><a href="/wiki/Phytanoyl-CoA" title="Phytanoyl-CoA">Phytanoyl-CoA</a></li> <li><a href="/wiki/Pristanic_acid" title="Pristanic acid">Pristanic acid</a></li> <li><a href="/wiki/Propionyl-CoA" title="Propionyl-CoA">Propionyl-CoA</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Mevalonic_acid" title="Mevalonic acid">Mevalonic acid</a></li> <li><a href="/wiki/Very_long_chain_fatty_acid" title="Very long chain fatty acid">Very long chain fatty acid</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Cholesterol_and_steroid_metabolic_intermediates" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Cholesterol_and_steroid_intermediates" title="Template:Cholesterol and steroid intermediates"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Cholesterol_and_steroid_intermediates" title="Template talk:Cholesterol and steroid intermediates"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Cholesterol_and_steroid_intermediates" title="Special:EditPage/Template:Cholesterol and steroid intermediates"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Cholesterol_and_steroid_metabolic_intermediates" style="font-size:114%;margin:0 4em"><a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a> and <a href="/wiki/Steroid" title="Steroid">steroid</a> <a href="/wiki/Metabolic_intermediate" title="Metabolic intermediate">metabolic intermediates</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Mevalonate_pathway" title="Mevalonate pathway">Mevalonate pathway</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">to <a href="/wiki/HMG-CoA" title="HMG-CoA">HMG-CoA</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a class="mw-selflink selflink">Acetyl-CoA</a></li> <li><a href="/wiki/Acetoacetyl-CoA" title="Acetoacetyl-CoA">Acetoacetyl-CoA</a></li> <li><a href="/wiki/Beta-Hydroxy_beta-methylbutyric_acid" class="mw-redirect" title="Beta-Hydroxy beta-methylbutyric acid">HMB</a></li> <li><a href="/wiki/Beta-Hydroxy_beta-methylbutyryl-CoA" class="mw-redirect" title="Beta-Hydroxy beta-methylbutyryl-CoA">HMB-CoA</a></li> <li><a href="/wiki/HMG-CoA" title="HMG-CoA">HMG-CoA</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Ketone_bodies" title="Ketone bodies">Ketone bodies</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetone" title="Acetone">Acetone</a></li> <li><a href="/wiki/Acetoacetic_acid" title="Acetoacetic acid">Acetoacetic acid</a></li> <li><a href="/wiki/Beta-Hydroxybutyric_acid" class="mw-redirect" title="Beta-Hydroxybutyric acid">β-Hydroxybutyric acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">to <a href="/wiki/Dimethylallyl_pyrophosphate" title="Dimethylallyl pyrophosphate">DMAPP</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Mevalonic_acid" title="Mevalonic acid">Mevalonic acid</a></li> <li><a href="/wiki/Phosphomevalonic_acid" title="Phosphomevalonic acid">Phosphomevalonic acid</a></li> <li><a href="/wiki/5-Diphosphomevalonic_acid" title="5-Diphosphomevalonic acid">5-Diphosphomevalonic acid</a></li> <li><a href="/wiki/Isopentenyl_pyrophosphate" title="Isopentenyl pyrophosphate">Isopentenyl pyrophosphate</a></li> <li><a href="/wiki/Dimethylallyl_pyrophosphate" title="Dimethylallyl pyrophosphate">Dimethylallyl pyrophosphate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Geranyl-</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Geranyl_pyrophosphate" title="Geranyl pyrophosphate">Geranyl pyrophosphate</a></li> <li><a href="/wiki/Geranylgeranyl_pyrophosphate" title="Geranylgeranyl pyrophosphate">Geranylgeranyl pyrophosphate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carotenoid" title="Carotenoid">Carotenoid</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Prephytoene_diphosphate" title="Prephytoene diphosphate">Prephytoene diphosphate</a></li> <li><a href="/wiki/Phytoene" title="Phytoene">Phytoene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Non-mevalonate_pathway" title="Non-mevalonate pathway">Non-mevalonate pathway</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1-Deoxy-D-xylulose_5-phosphate" title="1-Deoxy-D-xylulose 5-phosphate">DOXP</a></li> <li><a href="/wiki/2-C-methylerythritol_4-phosphate" class="mw-redirect" title="2-C-methylerythritol 4-phosphate">MEP</a></li> <li><a href="/wiki/4-diphosphocytidyl-2-C-methylerythritol" class="mw-redirect" title="4-diphosphocytidyl-2-C-methylerythritol">CDP-ME</a></li> <li><a href="/wiki/4-diphosphocytidyl-2-C-methyl-D-erythritol_2-phosphate" class="mw-redirect" title="4-diphosphocytidyl-2-C-methyl-D-erythritol 2-phosphate">CDP-MEP</a></li> <li><a href="/wiki/2-C-methyl-D-erythritol_2,4-cyclopyrophosphate" class="mw-redirect" title="2-C-methyl-D-erythritol 2,4-cyclopyrophosphate">MEcPP</a></li> <li><a href="/wiki/(E)-4-Hydroxy-3-methyl-but-2-enyl_pyrophosphate" title="(E)-4-Hydroxy-3-methyl-but-2-enyl pyrophosphate">HMB-PP</a></li> <li><a href="/wiki/Isopentenyl_pyrophosphate" title="Isopentenyl pyrophosphate">IPP</a></li> <li><a href="/wiki/Dimethylallyl_pyrophosphate" title="Dimethylallyl pyrophosphate">DMAPP</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">To <a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Farnesyl_pyrophosphate" title="Farnesyl pyrophosphate">Farnesyl pyrophosphate</a></li> <li><a href="/wiki/Squalene" title="Squalene">Squalene</a></li> <li><a href="/wiki/2,3-Oxidosqualene" title="2,3-Oxidosqualene">2,3-Oxidosqualene</a></li> <li><a href="/wiki/Lanosterol" title="Lanosterol">Lanosterol</a></li></ul> <ul><li><a href="/wiki/Lanosterol" title="Lanosterol">Lanosterol</a></li> <li><a href="/w/index.php?title=14-demethyllanosterol&action=edit&redlink=1" class="new" title="14-demethyllanosterol (page does not exist)">14-demethyllanosterol</a></li> <li><a href="/w/index.php?title=4alpha-Methylzymosterol&action=edit&redlink=1" class="new" title="4alpha-Methylzymosterol (page does not exist)">4alpha-Methylzymosterol</a></li> <li><a href="/w/index.php?title=Zymosterone&action=edit&redlink=1" class="new" title="Zymosterone (page does not exist)">Zymosterone</a></li> <li><a href="/wiki/Zymosterol" title="Zymosterol">Zymosterol</a></li></ul> <ul><li><a href="/wiki/Zymosterol" title="Zymosterol">Zymosterol</a></li> <li><a href="/w/index.php?title=Zymostenol&action=edit&redlink=1" class="new" title="Zymostenol (page does not exist)">Zymostenol</a></li> <li><a href="/wiki/Lathosterol" title="Lathosterol">Lathosterol</a></li> <li><a href="/wiki/7-Dehydrocholesterol" title="7-Dehydrocholesterol">7-Dehydrocholesterol</a></li> <li><a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a></li></ul> <ul><li><a href="/wiki/Zymosterol" title="Zymosterol">Zymosterol</a></li> <li><a href="/w/index.php?title=Cholesta-7,24-dien-3-ol&action=edit&redlink=1" class="new" title="Cholesta-7,24-dien-3-ol (page does not exist)">Cholesta-7,24-dien-3-ol</a></li> <li><a href="/wiki/7-Dehydrodesmosterol" title="7-Dehydrodesmosterol">7-Dehydrodesmosterol</a></li> <li><a href="/wiki/Desmosterol" title="Desmosterol">Desmosterol</a></li> <li><a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">From <a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a> <br />to <a href="/wiki/Steroid" title="Steroid">Steroid hormones</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/22R-Hydroxycholesterol" title="22R-Hydroxycholesterol">22<i>R</i>-Hydroxycholesterol</a></li> <li><a href="/wiki/20%CE%B1,22R-Dihydroxycholesterol" title="20α,22R-Dihydroxycholesterol">20α,22<i>R</i>-Dihydroxycholesterol</a></li> <li>See <a href="/wiki/Template:Steroid_hormones" title="Template:Steroid hormones">here</a> instead.</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Nonhuman</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">To <a href="/wiki/Sitosterol" class="mw-redirect" title="Sitosterol">Sitosterol</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cycloartenol" title="Cycloartenol">Cycloartenol</a></li> <li><a href="/w/index.php?title=Cycloeucalenol&action=edit&redlink=1" class="new" title="Cycloeucalenol (page does not exist)">Cycloeucalenol</a></li> <li><a href="/wiki/Obtusifoliol" title="Obtusifoliol">Obtusifoliol</a></li> <li><a href="/wiki/4%CE%B1-methylfecosterol" class="mw-redirect" title="4α-methylfecosterol">4α-methylfecosterol</a></li> <li><a href="/wiki/Isofucosterol" title="Isofucosterol">Isofucosterol</a></li> <li><a href="/wiki/24-Methylenelophenol" title="24-Methylenelophenol">24-Methylenelophenol</a></li> <li><a href="/wiki/Sitosterol" class="mw-redirect" title="Sitosterol">Sitosterol</a></li> <li>More <a href="/wiki/Phytosterol" title="Phytosterol">Phytosterols</a> see <a href="/wiki/Template:Steroid_hormones" title="Template:Steroid hormones">here</a> instead.</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">To <a href="/wiki/Ergocalciferol" title="Ergocalciferol">Ergocalciferol</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Fecosterol" title="Fecosterol">Fecosterol</a></li> <li><a href="/wiki/Episterol" title="Episterol">Episterol</a></li> <li><a href="/wiki/Ergostatrienol" class="mw-redirect" title="Ergostatrienol">Ergostatrienol</a></li> <li><a href="/w/index.php?title=Ergostatetraenol&action=edit&redlink=1" class="new" title="Ergostatetraenol (page does not exist)">Ergostatetraenol</a></li> <li><a href="/wiki/Ergosterol" title="Ergosterol">Ergosterol</a></li> <li><a href="/wiki/Ergocalciferol" title="Ergocalciferol">Ergocalciferol</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Glycolysis_metabolic_pathway" style="display:table;;padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Glycolysis" title="Template:Glycolysis"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Glycolysis" title="Template talk:Glycolysis"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Glycolysis" title="Special:EditPage/Template:Glycolysis"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Glycolysis_metabolic_pathway" style="font-size:114%;margin:0 4em"><a href="/wiki/Glycolysis" title="Glycolysis">Glycolysis</a> <a href="/wiki/Metabolic_pathway" title="Metabolic pathway">metabolic pathway</a></div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;border-width:0;"><div style="padding:0"><div style="background: transparent; padding: 2px 0 0 0; display: flex; flex-flow: row wrap;"> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:lightgreen;"> <p style="margin: 0.1em 0.5em;"><a href="/wiki/Glucose" title="Glucose">Glucose</a></p> </div><div style="margin: auto 0"><span typeof="mw:File"><a href="/wiki/File:D-glucose_wpmp.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3e/D-glucose_wpmp.svg/70px-D-glucose_wpmp.svg.png" decoding="async" width="70" height="70" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3e/D-glucose_wpmp.svg/105px-D-glucose_wpmp.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3e/D-glucose_wpmp.svg/140px-D-glucose_wpmp.svg.png 2x" data-file-width="128" data-file-height="128" /></a></span></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:#ffcccc;"> <p style="margin: 0.1em 0.5em;"><a href="/wiki/Hexokinase" title="Hexokinase">Hexokinase</a></p> </div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; align-items: flex-end;"><div style="width: 45%; float:left">ATP</div> <div style="width: 45%; float:right">ADP</div> </div><div style="width: 100%; clear:both; overflow: hidden; height: 27px;"><div style=""><span typeof="mw:File"><a href="/wiki/File:Biochem_reaction_arrow_forward_YYNN_horiz_med.svg" class="mw-file-description" title="Rightward reaction arrow with minor substrate(s) from top left and minor product(s) to top right"><img alt="Rightward reaction arrow with minor substrate(s) from top left and minor product(s) to top right" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/85/Biochem_reaction_arrow_forward_YYNN_horiz_med.svg/45px-Biochem_reaction_arrow_forward_YYNN_horiz_med.svg.png" decoding="async" width="45" height="45" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/85/Biochem_reaction_arrow_forward_YYNN_horiz_med.svg/68px-Biochem_reaction_arrow_forward_YYNN_horiz_med.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/85/Biochem_reaction_arrow_forward_YYNN_horiz_med.svg/90px-Biochem_reaction_arrow_forward_YYNN_horiz_med.svg.png 2x" data-file-width="75" data-file-height="75" /></a></span></div></div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; min-height: 22.5px;"></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:lightgreen;"> <p style="margin: 0.1em 0.5em;"><a href="/wiki/Glucose_6-phosphate" title="Glucose 6-phosphate">Glucose 6-phosphate</a></p> </div><div style="margin: auto 0"><span typeof="mw:File"><a href="/wiki/File:Alpha-D-glucose-6-phosphate_wpmp.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/80/Alpha-D-glucose-6-phosphate_wpmp.svg/70px-Alpha-D-glucose-6-phosphate_wpmp.svg.png" decoding="async" width="70" height="109" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/80/Alpha-D-glucose-6-phosphate_wpmp.svg/105px-Alpha-D-glucose-6-phosphate_wpmp.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/80/Alpha-D-glucose-6-phosphate_wpmp.svg/140px-Alpha-D-glucose-6-phosphate_wpmp.svg.png 2x" data-file-width="119" data-file-height="186" /></a></span></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:#ffcccc;"> <p style="margin: 0.1em 0.5em;"><a href="/wiki/Glucose-6-phosphate_isomerase" title="Glucose-6-phosphate isomerase">Glucose-6-phosphate<br />isomerase</a></p> </div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; align-items: flex-end; min-height: 22.5px;"> </div><div style="width: 100%; clear:both; overflow: hidden; height: 9px;"><div style="position: relative; bottom: 18px;"><span typeof="mw:File"><a href="/wiki/File:Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg" class="mw-file-description" title="Reversible left-right reaction arrow"><img alt="Reversible left-right reaction arrow" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/70/Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg/45px-Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg.png" decoding="async" width="45" height="45" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/70/Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg/68px-Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/70/Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg/90px-Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg.png 2x" data-file-width="75" data-file-height="75" /></a></span></div></div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; min-height: 22.5px;"></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:lightgreen;"> <p style="margin: 0.1em 0.5em;"><a href="/wiki/Fructose_6-phosphate" title="Fructose 6-phosphate">Fructose 6-phosphate</a></p> </div><div style="margin: auto 0"><span typeof="mw:File"><a href="/wiki/File:Beta-D-Fructose-6-phosphat2.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a0/Beta-D-Fructose-6-phosphat2.svg/100px-Beta-D-Fructose-6-phosphat2.svg.png" decoding="async" width="100" height="109" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a0/Beta-D-Fructose-6-phosphat2.svg/150px-Beta-D-Fructose-6-phosphat2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a0/Beta-D-Fructose-6-phosphat2.svg/200px-Beta-D-Fructose-6-phosphat2.svg.png 2x" data-file-width="180" data-file-height="197" /></a></span></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:#ffcccc;"> <p style="margin: 0.1em 0.5em;"><a href="/wiki/Phosphofructokinase-1" class="mw-redirect" title="Phosphofructokinase-1">Phosphofructokinase-1</a></p> </div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; align-items: flex-end;"><div style="width: 45%; float:left">ATP</div> <div style="width: 45%; float:right">ADP</div> </div><div style="width: 100%; clear:both; overflow: hidden; height: 27px;"><div style=""><span typeof="mw:File"><a href="/wiki/File:Biochem_reaction_arrow_forward_YYNN_horiz_med.svg" class="mw-file-description" title="Rightward reaction arrow with minor substrate(s) from top left and minor product(s) to top right"><img alt="Rightward reaction arrow with minor substrate(s) from top left and minor product(s) to top right" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/85/Biochem_reaction_arrow_forward_YYNN_horiz_med.svg/45px-Biochem_reaction_arrow_forward_YYNN_horiz_med.svg.png" decoding="async" width="45" height="45" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/85/Biochem_reaction_arrow_forward_YYNN_horiz_med.svg/68px-Biochem_reaction_arrow_forward_YYNN_horiz_med.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/85/Biochem_reaction_arrow_forward_YYNN_horiz_med.svg/90px-Biochem_reaction_arrow_forward_YYNN_horiz_med.svg.png 2x" data-file-width="75" data-file-height="75" /></a></span></div></div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; min-height: 22.5px;"></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:lightgreen;"> <p style="margin: 0.1em 0.5em;"><a href="/wiki/Fructose_1,6-bisphosphate" title="Fructose 1,6-bisphosphate">Fructose 1,6-bisphosphate</a></p> </div><div style="margin: auto 0"><span typeof="mw:File"><a href="/wiki/File:Beta-D-Fructose-1,6-bisphosphat2.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5e/Beta-D-Fructose-1%2C6-bisphosphat2.svg/100px-Beta-D-Fructose-1%2C6-bisphosphat2.svg.png" decoding="async" width="100" height="109" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5e/Beta-D-Fructose-1%2C6-bisphosphat2.svg/150px-Beta-D-Fructose-1%2C6-bisphosphat2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5e/Beta-D-Fructose-1%2C6-bisphosphat2.svg/200px-Beta-D-Fructose-1%2C6-bisphosphat2.svg.png 2x" data-file-width="180" data-file-height="197" /></a></span></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:#ffcccc;"> <p style="margin: 0.1em 0.5em;"><a href="/wiki/Fructose-bisphosphate_aldolase" title="Fructose-bisphosphate aldolase">Fructose-bisphosphate<br />aldolase</a></p> </div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; align-items: flex-end; min-height: 22.5px;"> </div><div style="width: 100%; clear:both; overflow: hidden; height: 9px;"><div style="position: relative; bottom: 18px;"><span typeof="mw:File"><a href="/wiki/File:Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg" class="mw-file-description" title="Reversible left-right reaction arrow"><img alt="Reversible left-right reaction arrow" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/70/Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg/45px-Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg.png" decoding="async" width="45" height="45" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/70/Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg/68px-Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/70/Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg/90px-Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg.png 2x" data-file-width="75" data-file-height="75" /></a></span></div></div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; min-height: 22.5px;"></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:lightgreen;"> <p style="margin: 0.1em 0.5em;"><a href="/wiki/Dihydroxyacetone_phosphate" title="Dihydroxyacetone phosphate">Dihydroxyacetone phosphate</a></p> </div><div style="margin: auto 0"><span typeof="mw:File"><a href="/wiki/File:Glycerone-phosphate_wpmp.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3f/Glycerone-phosphate_wpmp.svg/70px-Glycerone-phosphate_wpmp.svg.png" decoding="async" width="70" height="131" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3f/Glycerone-phosphate_wpmp.svg/105px-Glycerone-phosphate_wpmp.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3f/Glycerone-phosphate_wpmp.svg/140px-Glycerone-phosphate_wpmp.svg.png 2x" data-file-width="81" data-file-height="152" /></a></span></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block;"> <p style="margin: 0.1em 0.5em;">+</p> </div><div style="margin: auto 0">+</div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:lightgreen;"> <p style="margin: 0.1em 0.5em;"><a href="/wiki/Glyceraldehyde_3-phosphate" title="Glyceraldehyde 3-phosphate">Glyceraldehyde 3-phosphate</a></p> </div><div style="margin: auto 0"><span typeof="mw:File"><a href="/wiki/File:D-glyceraldehyde-3-phosphate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3a/D-glyceraldehyde-3-phosphate.svg/70px-D-glyceraldehyde-3-phosphate.svg.png" decoding="async" width="70" height="98" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3a/D-glyceraldehyde-3-phosphate.svg/105px-D-glyceraldehyde-3-phosphate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3a/D-glyceraldehyde-3-phosphate.svg/140px-D-glyceraldehyde-3-phosphate.svg.png 2x" data-file-width="512" data-file-height="718" /></a></span></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:#ffcccc;"> <p style="margin: 0.1em 0.5em;"><a href="/wiki/Triosephosphate_isomerase" title="Triosephosphate isomerase">Triosephosphate<br />isomerase</a></p> </div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; align-items: flex-end; min-height: 22.5px;"> </div><div style="width: 100%; clear:both; overflow: hidden; height: 9px;"><div style="position: relative; bottom: 18px;"><span typeof="mw:File"><a href="/wiki/File:Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg" class="mw-file-description" title="Reversible left-right reaction arrow"><img alt="Reversible left-right reaction arrow" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/70/Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg/45px-Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg.png" decoding="async" width="45" height="45" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/70/Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg/68px-Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/70/Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg/90px-Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg.png 2x" data-file-width="75" data-file-height="75" /></a></span></div></div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; min-height: 22.5px;"></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:lightgreen;"> <p style="margin: 0.1em 0.5em;"><strong>2 × </strong><a href="/wiki/Glyceraldehyde_3-phosphate" title="Glyceraldehyde 3-phosphate">Glyceraldehyde 3-phosphate</a></p> </div><div style="margin: auto 0"><strong>2 × </strong> <span typeof="mw:File"><a href="/wiki/File:D-glyceraldehyde-3-phosphate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3a/D-glyceraldehyde-3-phosphate.svg/70px-D-glyceraldehyde-3-phosphate.svg.png" decoding="async" width="70" height="98" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3a/D-glyceraldehyde-3-phosphate.svg/105px-D-glyceraldehyde-3-phosphate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3a/D-glyceraldehyde-3-phosphate.svg/140px-D-glyceraldehyde-3-phosphate.svg.png 2x" data-file-width="512" data-file-height="718" /></a></span></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:#ffcccc;"> <p style="margin: 0.1em 0.5em;"><a href="/wiki/Glyceraldehyde-3-phosphate_dehydrogenase" class="mw-redirect" title="Glyceraldehyde-3-phosphate dehydrogenase">Glyceraldehyde-3-phosphate<br />dehydrogenase</a></p> </div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; align-items: flex-end;"><div style="width: 45%; float:left">NAD<sup>+</sup>+ P<sub>i</sub></div> <div style="width: 45%; float:right">NADH + H<sup>+</sup></div> </div><div style="width: 100%; clear:both; overflow: hidden; height: 45px;"><div style=""><span typeof="mw:File"><a href="/wiki/File:Biochem_reaction_arrow_reversible_YYYY_horiz_med.svg" class="mw-file-description" title="Reversible left-right reaction arrow with minor forward substrate(s) from top left, minor forward product(s) to top right, minor reverse substrate(s) from bottom right and minor reverse product(s) to bottom left"><img alt="Reversible left-right reaction arrow with minor forward substrate(s) from top left, minor forward product(s) to top right, minor reverse substrate(s) from bottom right and minor reverse product(s) to bottom left" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/19/Biochem_reaction_arrow_reversible_YYYY_horiz_med.svg/45px-Biochem_reaction_arrow_reversible_YYYY_horiz_med.svg.png" decoding="async" width="45" height="45" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/19/Biochem_reaction_arrow_reversible_YYYY_horiz_med.svg/68px-Biochem_reaction_arrow_reversible_YYYY_horiz_med.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/19/Biochem_reaction_arrow_reversible_YYYY_horiz_med.svg/90px-Biochem_reaction_arrow_reversible_YYYY_horiz_med.svg.png 2x" data-file-width="75" data-file-height="75" /></a></span></div></div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around;"><div style="width: 45%; float:left">NAD<sup>+</sup>+ P<sub>i</sub></div> <div style="width: 45%; float:right">NADH + H<sup>+</sup></div><div style="clear:both;" class=""></div></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:lightgreen;"> <p style="margin: 0.1em 0.5em;"><strong>2 × </strong><a href="/wiki/1,3-Bisphosphoglycerate" class="mw-redirect" title="1,3-Bisphosphoglycerate">1,3-Bisphosphoglycerate</a></p> </div><div style="margin: auto 0"><strong>2 × </strong> <span typeof="mw:File"><a href="/wiki/File:1,3-bisphospho-D-glycerate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/75/1%2C3-bisphospho-D-glycerate.svg/70px-1%2C3-bisphospho-D-glycerate.svg.png" decoding="async" width="70" height="125" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/75/1%2C3-bisphospho-D-glycerate.svg/105px-1%2C3-bisphospho-D-glycerate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/75/1%2C3-bisphospho-D-glycerate.svg/140px-1%2C3-bisphospho-D-glycerate.svg.png 2x" data-file-width="222" data-file-height="396" /></a></span></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:#ffcccc;"> <p style="margin: 0.1em 0.5em;"><a href="/wiki/Phosphoglycerate_kinase" title="Phosphoglycerate kinase">Phosphoglycerate kinase</a></p> </div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; align-items: flex-end;"><div style="width: 45%; float:left">ADP</div> <div style="width: 45%; float:right">ATP</div> </div><div style="width: 100%; clear:both; overflow: hidden; height: 45px;"><div style=""><span typeof="mw:File"><a href="/wiki/File:Biochem_reaction_arrow_reversible_YYYY_horiz_med.svg" class="mw-file-description" title="Reversible left-right reaction arrow with minor forward substrate(s) from top left, minor forward product(s) to top right, minor reverse substrate(s) from bottom right and minor reverse product(s) to bottom left"><img alt="Reversible left-right reaction arrow with minor forward substrate(s) from top left, minor forward product(s) to top right, minor reverse substrate(s) from bottom right and minor reverse product(s) to bottom left" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/19/Biochem_reaction_arrow_reversible_YYYY_horiz_med.svg/45px-Biochem_reaction_arrow_reversible_YYYY_horiz_med.svg.png" decoding="async" width="45" height="45" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/19/Biochem_reaction_arrow_reversible_YYYY_horiz_med.svg/68px-Biochem_reaction_arrow_reversible_YYYY_horiz_med.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/19/Biochem_reaction_arrow_reversible_YYYY_horiz_med.svg/90px-Biochem_reaction_arrow_reversible_YYYY_horiz_med.svg.png 2x" data-file-width="75" data-file-height="75" /></a></span></div></div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around;"><div style="width: 45%; float:left">ADP</div> <div style="width: 45%; float:right">ATP</div><div style="clear:both;" class=""></div></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:lightgreen;"> <p style="margin: 0.1em 0.5em;"><strong>2 × </strong><a href="/wiki/3-Phosphoglyceric_acid" title="3-Phosphoglyceric acid">3-Phosphoglycerate</a></p> </div><div style="margin: auto 0"><strong>2 × </strong> <span typeof="mw:File"><a href="/wiki/File:3-phospho-D-glycerate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/99/3-phospho-D-glycerate.svg/70px-3-phospho-D-glycerate.svg.png" decoding="async" width="70" height="100" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/99/3-phospho-D-glycerate.svg/105px-3-phospho-D-glycerate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/99/3-phospho-D-glycerate.svg/140px-3-phospho-D-glycerate.svg.png 2x" data-file-width="193" data-file-height="277" /></a></span></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:#ffcccc;"> <p style="margin: 0.1em 0.5em;"><a href="/wiki/Phosphoglycerate_mutase" title="Phosphoglycerate mutase">Phosphoglycerate mutase</a></p> </div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; align-items: flex-end; min-height: 22.5px;"> </div><div style="width: 100%; clear:both; overflow: hidden; height: 9px;"><div style="position: relative; bottom: 18px;"><span typeof="mw:File"><a href="/wiki/File:Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg" class="mw-file-description" title="Reversible left-right reaction arrow"><img alt="Reversible left-right reaction arrow" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/70/Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg/45px-Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg.png" decoding="async" width="45" height="45" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/70/Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg/68px-Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/70/Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg/90px-Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg.png 2x" data-file-width="75" data-file-height="75" /></a></span></div></div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; min-height: 22.5px;"></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:lightgreen;"> <p style="margin: 0.1em 0.5em;"><strong>2 × </strong><a href="/wiki/2-Phosphoglyceric_acid" title="2-Phosphoglyceric acid">2-Phosphoglycerate</a></p> </div><div style="margin: auto 0"><strong>2 × </strong> <span typeof="mw:File"><a href="/wiki/File:2-phospho-D-glycerate_wpmp.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2a/2-phospho-D-glycerate_wpmp.svg/70px-2-phospho-D-glycerate_wpmp.svg.png" decoding="async" width="70" height="58" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2a/2-phospho-D-glycerate_wpmp.svg/105px-2-phospho-D-glycerate_wpmp.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2a/2-phospho-D-glycerate_wpmp.svg/140px-2-phospho-D-glycerate_wpmp.svg.png 2x" data-file-width="115" data-file-height="95" /></a></span></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:#ffcccc;"> <p style="margin: 0.1em 0.5em;"><a href="/wiki/Phosphopyruvate_hydratase" class="mw-redirect" title="Phosphopyruvate hydratase">Phosphopyruvate<br />hydratase</a> (<a href="/wiki/Enolase" title="Enolase">enolase</a>)</p> </div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; align-items: flex-end;"><div style="width: 45%; float:left"> </div> <div style="width: 45%; float:right">H<sub>2</sub>O</div> </div><div style="width: 100%; clear:both; overflow: hidden; height: 45px;"><div style=""><span typeof="mw:File"><a href="/wiki/File:Biochem_reaction_arrow_reversible_NYYN_horiz_med.svg" class="mw-file-description" title="Reversible left-right reaction arrow with minor forward product(s) to top right and minor reverse substrate(s) from bottom right"><img alt="Reversible left-right reaction arrow with minor forward product(s) to top right and minor reverse substrate(s) from bottom right" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/86/Biochem_reaction_arrow_reversible_NYYN_horiz_med.svg/45px-Biochem_reaction_arrow_reversible_NYYN_horiz_med.svg.png" decoding="async" width="45" height="45" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/86/Biochem_reaction_arrow_reversible_NYYN_horiz_med.svg/68px-Biochem_reaction_arrow_reversible_NYYN_horiz_med.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/86/Biochem_reaction_arrow_reversible_NYYN_horiz_med.svg/90px-Biochem_reaction_arrow_reversible_NYYN_horiz_med.svg.png 2x" data-file-width="75" data-file-height="75" /></a></span></div></div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around;"><div style="width: 45%; float:left"> </div> <div style="width: 45%; float:right">H<sub>2</sub>O</div><div style="clear:both;" class=""></div></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:lightgreen;"> <p style="margin: 0.1em 0.5em;"><strong>2 × </strong><a href="/wiki/Phosphoenolpyruvate" class="mw-redirect" title="Phosphoenolpyruvate">Phosphoenolpyruvate</a></p> </div><div style="margin: auto 0"><strong>2 × </strong> <span typeof="mw:File"><a href="/wiki/File:Phosphoenolpyruvate_wpmp.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bc/Phosphoenolpyruvate_wpmp.svg/70px-Phosphoenolpyruvate_wpmp.svg.png" decoding="async" width="70" height="99" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bc/Phosphoenolpyruvate_wpmp.svg/105px-Phosphoenolpyruvate_wpmp.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bc/Phosphoenolpyruvate_wpmp.svg/140px-Phosphoenolpyruvate_wpmp.svg.png 2x" data-file-width="77" data-file-height="109" /></a></span></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:#ffcccc;"> <p style="margin: 0.1em 0.5em;"><a href="/wiki/Pyruvate_kinase" title="Pyruvate kinase">Pyruvate kinase</a></p> </div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; align-items: flex-end;"><div style="width: 45%; float:left">ADP</div> <div style="width: 45%; float:right">ATP</div> </div><div style="width: 100%; clear:both; overflow: hidden; height: 27px;"><div style=""><span typeof="mw:File"><a href="/wiki/File:Biochem_reaction_arrow_forward_YYNN_horiz_med.svg" class="mw-file-description" title="Rightward reaction arrow with minor substrate(s) from top left and minor product(s) to top right"><img alt="Rightward reaction arrow with minor substrate(s) from top left and minor product(s) to top right" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/85/Biochem_reaction_arrow_forward_YYNN_horiz_med.svg/45px-Biochem_reaction_arrow_forward_YYNN_horiz_med.svg.png" decoding="async" width="45" height="45" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/85/Biochem_reaction_arrow_forward_YYNN_horiz_med.svg/68px-Biochem_reaction_arrow_forward_YYNN_horiz_med.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/85/Biochem_reaction_arrow_forward_YYNN_horiz_med.svg/90px-Biochem_reaction_arrow_forward_YYNN_horiz_med.svg.png 2x" data-file-width="75" data-file-height="75" /></a></span></div></div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; min-height: 22.5px;"></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:lightgreen;"> <p style="margin: 0.1em 0.5em;"><strong>2 × </strong><a href="/wiki/Pyruvic_acid" title="Pyruvic acid">Pyruvate</a></p> </div><div style="margin: auto 0"><strong>2 × </strong> <span typeof="mw:File"><a href="/wiki/File:Pyruvat.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/79/Pyruvat.svg/70px-Pyruvat.svg.png" decoding="async" width="70" height="37" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/79/Pyruvat.svg/105px-Pyruvat.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/79/Pyruvat.svg/140px-Pyruvat.svg.png 2x" data-file-width="154" data-file-height="82" /></a></span></div> </div> </div> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Citric_acid_cycle_metabolic_pathway" style="display:table;;padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Citric_acid_cycle" title="Template:Citric acid cycle"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Citric_acid_cycle" title="Template talk:Citric acid cycle"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Citric_acid_cycle" title="Special:EditPage/Template:Citric acid cycle"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Citric_acid_cycle_metabolic_pathway" style="font-size:114%;margin:0 4em"><a href="/wiki/Citric_acid_cycle" title="Citric acid cycle">Citric acid cycle</a> <a href="/wiki/Metabolic_pathway" title="Metabolic pathway">metabolic pathway</a></div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;border-width:0;"><div style="padding:0"> <table style="width:100%" class="wraplinks"> <tbody><tr> <td rowspan="2" style="vertical-align:bottom"><div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:lightgreen;"> <p style="margin: 0.1em 0.5em;"><a class="mw-selflink selflink">Acetyl-CoA</a></p> </div><div style="margin: auto 0"><span typeof="mw:File"><a href="/wiki/File:Acetyl_co-A_wpmp.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fe/Acetyl_co-A_wpmp.svg/45px-Acetyl_co-A_wpmp.svg.png" decoding="async" width="45" height="19" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fe/Acetyl_co-A_wpmp.svg/68px-Acetyl_co-A_wpmp.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fe/Acetyl_co-A_wpmp.svg/90px-Acetyl_co-A_wpmp.svg.png 2x" data-file-width="637" data-file-height="274" /></a></span></div> </div> + <style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>O</span> </td> <td colspan="2"> <div style="display:flex"> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:lightgreen;"> <p style="margin: 0.1em 0.5em;"><a href="/wiki/Oxaloacetate" class="mw-redirect" title="Oxaloacetate">Oxaloacetate</a></p> </div><div style="margin: auto 0"><span typeof="mw:File"><a href="/wiki/File:Oxaloacetate_wpmp.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c8/Oxaloacetate_wpmp.png/60px-Oxaloacetate_wpmp.png" decoding="async" width="60" height="99" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/c/c8/Oxaloacetate_wpmp.png 1.5x" data-file-width="72" data-file-height="119" /></a></span></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; align-items: flex-end; min-height: 22.5px;"> </div><div style="width: 100%; clear:both; overflow: hidden; height: 27px;"><div style="position: relative; bottom: 18px;"><span typeof="mw:File"><a href="/wiki/File:Biochem_reaction_arrow_reverse_NNYY_horiz_med.svg" class="mw-file-description" title="Leftward reaction arrow with minor product(s) to bottom left and minor substrate(s) from bottom right"><img alt="Leftward reaction arrow with minor product(s) to bottom left and minor substrate(s) from bottom right" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/de/Biochem_reaction_arrow_reverse_NNYY_horiz_med.svg/45px-Biochem_reaction_arrow_reverse_NNYY_horiz_med.svg.png" decoding="async" width="45" height="45" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/de/Biochem_reaction_arrow_reverse_NNYY_horiz_med.svg/68px-Biochem_reaction_arrow_reverse_NNYY_horiz_med.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/de/Biochem_reaction_arrow_reverse_NNYY_horiz_med.svg/90px-Biochem_reaction_arrow_reverse_NNYY_horiz_med.svg.png 2x" data-file-width="75" data-file-height="75" /></a></span></div></div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around;"><div style="width: 45%; float:left">NADH +H<sup>+</sup></div> <div style="width: 45%; float:right">NAD<sup>+</sup></div><div style="clear:both;" class=""></div></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:lightgreen;"> <p style="margin: 0.1em 0.5em;"><a href="/wiki/Malate" class="mw-redirect" title="Malate">Malate</a></p> </div><div style="margin: auto 0"><span typeof="mw:File"><a href="/wiki/File:S-malate_wpmp.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e3/S-malate_wpmp.png/72px-S-malate_wpmp.png" decoding="async" width="72" height="98" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e3/S-malate_wpmp.png/108px-S-malate_wpmp.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e3/S-malate_wpmp.png/144px-S-malate_wpmp.png 2x" data-file-width="551" data-file-height="752" /></a></span></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; align-items: flex-end; min-height: 22.5px;"> </div><div style="width: 100%; clear:both; overflow: hidden; height: 27px;"><div style="position: relative; bottom: 18px;"><span typeof="mw:File"><a href="/wiki/File:Biochem_reaction_arrow_reverse_NNYN_horiz_med.svg" class="mw-file-description" title="Leftward reaction arrow with minor substrate(s) from bottom right"><img alt="Leftward reaction arrow with minor substrate(s) from bottom right" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Biochem_reaction_arrow_reverse_NNYN_horiz_med.svg/45px-Biochem_reaction_arrow_reverse_NNYN_horiz_med.svg.png" decoding="async" width="45" height="45" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Biochem_reaction_arrow_reverse_NNYN_horiz_med.svg/68px-Biochem_reaction_arrow_reverse_NNYN_horiz_med.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Biochem_reaction_arrow_reverse_NNYN_horiz_med.svg/90px-Biochem_reaction_arrow_reverse_NNYN_horiz_med.svg.png 2x" data-file-width="75" data-file-height="75" /></a></span></div></div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around;"><div style="width: 45%; float:left"> </div> <div style="width: 45%; float:right">H<sub>2</sub>O</div><div style="clear:both;" class=""></div></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:lightgreen;"> <p style="margin: 0.1em 0.5em;"><a href="/wiki/Fumarate" class="mw-redirect" title="Fumarate">Fumarate</a></p> </div><div style="margin: auto 0"><span typeof="mw:File"><a href="/wiki/File:Fumaric_acid_wpmp.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/12/Fumaric_acid_wpmp.png/60px-Fumaric_acid_wpmp.png" decoding="async" width="60" height="99" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/1/12/Fumaric_acid_wpmp.png 1.5x" data-file-width="72" data-file-height="119" /></a></span></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; align-items: flex-end; min-height: 22.5px;"> </div><div style="width: 100%; clear:both; overflow: hidden; height: 27px;"><div style="position: relative; bottom: 18px;"><span typeof="mw:File"><a href="/wiki/File:Biochem_reaction_arrow_reverse_NNYY_horiz_med.svg" class="mw-file-description" title="Leftward reaction arrow with minor product(s) to bottom left and minor substrate(s) from bottom right"><img alt="Leftward reaction arrow with minor product(s) to bottom left and minor substrate(s) from bottom right" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/de/Biochem_reaction_arrow_reverse_NNYY_horiz_med.svg/45px-Biochem_reaction_arrow_reverse_NNYY_horiz_med.svg.png" decoding="async" width="45" height="45" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/de/Biochem_reaction_arrow_reverse_NNYY_horiz_med.svg/68px-Biochem_reaction_arrow_reverse_NNYY_horiz_med.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/de/Biochem_reaction_arrow_reverse_NNYY_horiz_med.svg/90px-Biochem_reaction_arrow_reverse_NNYY_horiz_med.svg.png 2x" data-file-width="75" data-file-height="75" /></a></span></div></div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around;"><div style="width: 45%; float:left">FADH<sub>2</sub></div> <div style="width: 45%; float:right">FAD</div><div style="clear:both;" class=""></div></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:lightgreen;"> <p style="margin: 0.1em 0.5em;"><a href="/wiki/Succinate" class="mw-redirect" title="Succinate">Succinate</a></p> </div><div style="margin: auto 0"><span typeof="mw:File"><a href="/wiki/File:Succinate_wpmp.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5a/Succinate_wpmp.png/60px-Succinate_wpmp.png" decoding="async" width="60" height="99" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/5/5a/Succinate_wpmp.png 1.5x" data-file-width="72" data-file-height="119" /></a></span></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; align-items: flex-end; min-height: 22.5px;"> </div><div style="width: 100%; clear:both; overflow: hidden; height: 27px;"><div style="position: relative; bottom: 18px;"><span typeof="mw:File"><a href="/wiki/File:Biochem_reaction_arrow_reverse_NNYY_horiz_med.svg" class="mw-file-description" title="Leftward reaction arrow with minor product(s) to bottom left and minor substrate(s) from bottom right"><img alt="Leftward reaction arrow with minor product(s) to bottom left and minor substrate(s) from bottom right" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/de/Biochem_reaction_arrow_reverse_NNYY_horiz_med.svg/45px-Biochem_reaction_arrow_reverse_NNYY_horiz_med.svg.png" decoding="async" width="45" height="45" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/de/Biochem_reaction_arrow_reverse_NNYY_horiz_med.svg/68px-Biochem_reaction_arrow_reverse_NNYY_horiz_med.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/de/Biochem_reaction_arrow_reverse_NNYY_horiz_med.svg/90px-Biochem_reaction_arrow_reverse_NNYY_horiz_med.svg.png 2x" data-file-width="75" data-file-height="75" /></a></span></div></div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around;"><div style="width: 45%; float:left">CoA + ATP (GTP)</div> <div style="width: 45%; float:right">P<sub>i</sub> + ADP (GDP)</div><div style="clear:both;" class=""></div></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:lightgreen;"> <p style="margin: 0.1em 0.5em;"><a href="/wiki/Succinyl-CoA" title="Succinyl-CoA">Succinyl-CoA</a></p> </div><div style="margin: auto 0"><span typeof="mw:File"><a href="/wiki/File:Succinyl-CoA_wpmp.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/db/Succinyl-CoA_wpmp.png/60px-Succinyl-CoA_wpmp.png" decoding="async" width="60" height="115" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/d/db/Succinyl-CoA_wpmp.png 1.5x" data-file-width="73" data-file-height="140" /></a></span></div> </div> </div> </td></tr> <tr style="line-height: 0.98;"> <td rowspan="2" style="text-align:left;padding-left:25px"><span typeof="mw:File"><a href="/wiki/File:Biochem_reaction_arrow_forward_YNNY_vert_med.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8f/Biochem_reaction_arrow_forward_YNNY_vert_med.svg/45px-Biochem_reaction_arrow_forward_YNNY_vert_med.svg.png" decoding="async" width="45" height="45" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8f/Biochem_reaction_arrow_forward_YNNY_vert_med.svg/68px-Biochem_reaction_arrow_forward_YNNY_vert_med.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8f/Biochem_reaction_arrow_forward_YNNY_vert_med.svg/90px-Biochem_reaction_arrow_forward_YNNY_vert_med.svg.png 2x" data-file-width="75" data-file-height="75" /></a></span> </td> <td rowspan="2" style="text-align:right;padding-right:25px"><span typeof="mw:File"><a href="/wiki/File:Biochem_reaction_arrow_reverse_NYYN_vert_med.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6e/Biochem_reaction_arrow_reverse_NYYN_vert_med.svg/45px-Biochem_reaction_arrow_reverse_NYYN_vert_med.svg.png" decoding="async" width="45" height="45" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6e/Biochem_reaction_arrow_reverse_NYYN_vert_med.svg/68px-Biochem_reaction_arrow_reverse_NYYN_vert_med.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6e/Biochem_reaction_arrow_reverse_NYYN_vert_med.svg/90px-Biochem_reaction_arrow_reverse_NYYN_vert_med.svg.png 2x" data-file-width="75" data-file-height="75" /></a></span> </td> <td>NADH + H<sup>+</sup> + CO<sub style="font-size: 80%;vertical-align: -0.35em">2</sub> </td></tr> <tr> <td><a href="/wiki/Coenzyme_A" title="Coenzyme A">CoA</a> </td> <td>NAD<sup>+</sup> </td></tr> <tr> <td> </td> <td colspan="2"> <div style="display:flex"> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="margin: auto 0"><span typeof="mw:File"><a href="/wiki/File:Citrate_wpmp.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/22/Citrate_wpmp.png/70px-Citrate_wpmp.png" decoding="async" width="70" height="107" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/2/22/Citrate_wpmp.png 1.5x" data-file-width="92" data-file-height="141" /></a></span></div> <div style="width: 100%; display: block; background-color:lightgreen;"> <p style="margin: 0.1em 0.5em;"><a href="/wiki/Citrate" class="mw-redirect" title="Citrate">Citrate</a></p> </div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; align-items: flex-end;"><div style="width: 45%; float:left"> </div> <div style="width: 45%; float:right"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>O</span></div> </div><div style="width: 100%; clear:both; overflow: hidden; height: 27px;"><div style=""><span typeof="mw:File"><a href="/wiki/File:Biochem_reaction_arrow_forward_NYNN_horiz_med.svg" class="mw-file-description" title="Rightward reaction arrow with minor product(s) to top right"><img alt="Rightward reaction arrow with minor product(s) to top right" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/09/Biochem_reaction_arrow_forward_NYNN_horiz_med.svg/45px-Biochem_reaction_arrow_forward_NYNN_horiz_med.svg.png" decoding="async" width="45" height="45" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/09/Biochem_reaction_arrow_forward_NYNN_horiz_med.svg/68px-Biochem_reaction_arrow_forward_NYNN_horiz_med.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/09/Biochem_reaction_arrow_forward_NYNN_horiz_med.svg/90px-Biochem_reaction_arrow_forward_NYNN_horiz_med.svg.png 2x" data-file-width="75" data-file-height="75" /></a></span></div></div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; min-height: 22.5px;"></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="margin: auto 0"><span typeof="mw:File"><a href="/wiki/File:Cis-Aconitate_wpmp.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/eb/Cis-Aconitate_wpmp.png/60px-Cis-Aconitate_wpmp.png" decoding="async" width="60" height="105" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/e/eb/Cis-Aconitate_wpmp.png 1.5x" data-file-width="80" data-file-height="140" /></a></span></div> <div style="width: 100%; display: block; background-color:lightgreen;"> <p style="margin: 0.1em 0.5em;">cis-<a href="/wiki/Aconitic_acid" title="Aconitic acid">Aconitate</a></p> </div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; align-items: flex-end;"><div style="width: 45%; float:left"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>O</span></div> <div style="width: 45%; float:right"> </div> </div><div style="width: 100%; clear:both; overflow: hidden; height: 27px;"><div style=""><span typeof="mw:File"><a href="/wiki/File:Biochem_reaction_arrow_forward_YNNN_horiz_med.svg" class="mw-file-description" title="Rightward reaction arrow with minor substrate(s) from top left"><img alt="Rightward reaction arrow with minor substrate(s) from top left" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/12/Biochem_reaction_arrow_forward_YNNN_horiz_med.svg/45px-Biochem_reaction_arrow_forward_YNNN_horiz_med.svg.png" decoding="async" width="45" height="45" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/12/Biochem_reaction_arrow_forward_YNNN_horiz_med.svg/68px-Biochem_reaction_arrow_forward_YNNN_horiz_med.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/12/Biochem_reaction_arrow_forward_YNNN_horiz_med.svg/90px-Biochem_reaction_arrow_forward_YNNN_horiz_med.svg.png 2x" data-file-width="75" data-file-height="75" /></a></span></div></div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; min-height: 22.5px;"></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="margin: auto 0"><span typeof="mw:File"><a href="/wiki/File:Isocitric_acid.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e5/Isocitric_acid.svg/70px-Isocitric_acid.svg.png" decoding="async" width="70" height="94" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e5/Isocitric_acid.svg/105px-Isocitric_acid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e5/Isocitric_acid.svg/140px-Isocitric_acid.svg.png 2x" data-file-width="315" data-file-height="425" /></a></span></div> <div style="width: 100%; display: block; background-color:lightgreen;"> <p style="margin: 0.1em 0.5em;"><a href="/wiki/Isocitrate" class="mw-redirect" title="Isocitrate">Isocitrate</a></p> </div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; align-items: flex-end;"><div style="width: 45%; float:left">NAD(P)<sup>+</sup></div> <div style="width: 45%; float:right">NAD(P)H + <span class="Unicode"> </span>H<sup>+</sup></div> </div><div style="width: 100%; clear:both; overflow: hidden; height: 27px;"><div style=""><span typeof="mw:File"><a href="/wiki/File:Biochem_reaction_arrow_forward_YYNN_horiz_med.svg" class="mw-file-description" title="Rightward reaction arrow with minor substrate(s) from top left and minor product(s) to top right"><img alt="Rightward reaction arrow with minor substrate(s) from top left and minor product(s) to top right" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/85/Biochem_reaction_arrow_forward_YYNN_horiz_med.svg/45px-Biochem_reaction_arrow_forward_YYNN_horiz_med.svg.png" decoding="async" width="45" height="45" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/85/Biochem_reaction_arrow_forward_YYNN_horiz_med.svg/68px-Biochem_reaction_arrow_forward_YYNN_horiz_med.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/85/Biochem_reaction_arrow_forward_YYNN_horiz_med.svg/90px-Biochem_reaction_arrow_forward_YYNN_horiz_med.svg.png 2x" data-file-width="75" data-file-height="75" /></a></span></div></div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; min-height: 22.5px;"></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="margin: auto 0"><span typeof="mw:File"><a href="/wiki/File:Oxalosuccinate_wpmp.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/19/Oxalosuccinate_wpmp.png/70px-Oxalosuccinate_wpmp.png" decoding="async" width="70" height="104" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/1/19/Oxalosuccinate_wpmp.png 1.5x" data-file-width="94" data-file-height="140" /></a></span></div> <div style="width: 100%; display: block; background-color:lightgreen;"> <p style="margin: 0.1em 0.5em;"><a href="/wiki/Oxalosuccinate" class="mw-redirect" title="Oxalosuccinate">Oxalosuccinate</a></p> </div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; align-items: flex-end;"><div style="width: 45%; float:left"> </div> <div style="width: 45%; float:right">CO<sub style="font-size: 80%;vertical-align: -0.35em">2</sub></div> </div><div style="width: 100%; clear:both; overflow: hidden; height: 27px;"><div style=""><span typeof="mw:File"><a href="/wiki/File:Biochem_reaction_arrow_forward_NYNN_horiz_med.svg" class="mw-file-description" title="Rightward reaction arrow with minor product(s) to top right"><img alt="Rightward reaction arrow with minor product(s) to top right" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/09/Biochem_reaction_arrow_forward_NYNN_horiz_med.svg/45px-Biochem_reaction_arrow_forward_NYNN_horiz_med.svg.png" decoding="async" width="45" height="45" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/09/Biochem_reaction_arrow_forward_NYNN_horiz_med.svg/68px-Biochem_reaction_arrow_forward_NYNN_horiz_med.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/09/Biochem_reaction_arrow_forward_NYNN_horiz_med.svg/90px-Biochem_reaction_arrow_forward_NYNN_horiz_med.svg.png 2x" data-file-width="75" data-file-height="75" /></a></span></div></div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; min-height: 22.5px;"></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="margin: auto 0"><span typeof="mw:File"><a href="/wiki/File:2-oxoglutarate_wpmp.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d9/2-oxoglutarate_wpmp.svg/70px-2-oxoglutarate_wpmp.svg.png" decoding="async" width="70" height="136" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d9/2-oxoglutarate_wpmp.svg/105px-2-oxoglutarate_wpmp.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d9/2-oxoglutarate_wpmp.svg/140px-2-oxoglutarate_wpmp.svg.png 2x" data-file-width="93" data-file-height="181" /></a></span></div> <div style="width: 100%; display: block; background-color:lightgreen;"> <p style="margin: 0.1em 0.5em;"><a href="/wiki/Alpha-Ketoglutaric_acid" class="mw-redirect" title="Alpha-Ketoglutaric acid">2-oxoglutarate</a></p> </div> </div> </div> </td></tr></tbody></table> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Amino_acid_metabolism_metabolic_intermediates" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Amino_acid_metabolism_intermediates" title="Template:Amino acid metabolism intermediates"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Amino_acid_metabolism_intermediates" title="Template talk:Amino acid metabolism intermediates"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Amino_acid_metabolism_intermediates" title="Special:EditPage/Template:Amino acid metabolism intermediates"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Amino_acid_metabolism_metabolic_intermediates" style="font-size:114%;margin:0 4em"><a href="/wiki/Amino_acid" title="Amino acid">Amino acid</a> <a href="/wiki/Amino_acid_synthesis" title="Amino acid synthesis">metabolism</a> <a href="/wiki/Metabolic_intermediate" title="Metabolic intermediate">metabolic intermediates</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Ketogenic_amino_acid" title="Ketogenic amino acid">K</a>→<a class="mw-selflink selflink">acetyl-CoA</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Lysine" title="Lysine">lysine</a>→</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Saccharopine" title="Saccharopine">Saccharopine</a></li> <li><a href="/wiki/Allysine" title="Allysine">Allysine</a></li> <li><a href="/wiki/Alpha-Aminoadipic_acid" class="mw-redirect" title="Alpha-Aminoadipic acid">α-Aminoadipic acid</a></li> <li><a href="/wiki/2-Oxoadipic_acid" title="2-Oxoadipic acid">2-Oxoadipic acid</a></li> <li><a href="/wiki/Glutaryl-CoA" title="Glutaryl-CoA">Glutaryl-CoA</a></li> <li><a href="/wiki/Glutaconyl-CoA" title="Glutaconyl-CoA">Glutaconyl-CoA</a></li> <li><a href="/wiki/Crotonyl-CoA" title="Crotonyl-CoA">Crotonyl-CoA</a></li> <li><a href="/wiki/Beta-Hydroxybutyryl-CoA" class="mw-redirect" title="Beta-Hydroxybutyryl-CoA">β-Hydroxybutyryl-CoA</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Leucine" title="Leucine">leucine</a>→</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Beta-Hydroxy_beta-methylbutyric_acid" class="mw-redirect" title="Beta-Hydroxy beta-methylbutyric acid">β-Hydroxy β-methylbutyric acid</a></li> <li><a href="/wiki/Beta-Hydroxy_beta-methylbutyryl-CoA" class="mw-redirect" title="Beta-Hydroxy beta-methylbutyryl-CoA">β-Hydroxy β-methylbutyryl-CoA</a></li> <li><a href="/wiki/Isovaleryl-CoA" title="Isovaleryl-CoA">Isovaleryl-CoA</a></li> <li><a href="/wiki/Alpha-Ketoisocaproic_acid" class="mw-redirect" title="Alpha-Ketoisocaproic acid">α-Ketoisocaproic acid</a></li> <li><a href="/wiki/Beta-Ketoisocaproic_acid" class="mw-redirect" title="Beta-Ketoisocaproic acid">β-Ketoisocaproic acid</a></li> <li><a href="/w/index.php?title=Beta-Ketoisocaproyl-CoA&action=edit&redlink=1" class="new" title="Beta-Ketoisocaproyl-CoA (page does not exist)">β-Ketoisocaproyl-CoA</a></li> <li><a href="/wiki/%CE%92-Leucine" title="Β-Leucine">β-Leucine</a></li> <li><a href="/wiki/Methylcrotonyl-CoA" title="Methylcrotonyl-CoA">β-Methylcrotonyl-CoA</a></li> <li><a href="/wiki/%CE%92-Methylglutaconyl-CoA" class="mw-redirect" title="Β-Methylglutaconyl-CoA">β-Methylglutaconyl-CoA</a></li> <li><a href="/wiki/HMG-CoA" title="HMG-CoA">β-Hydroxy β-methylglutaryl-CoA</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tryptophan" title="Tryptophan">tryptophan</a>→<a href="/wiki/Alanine" title="Alanine">alanine</a>→</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/N%27-Formylkynurenine" title="N'-Formylkynurenine"><i>N</i>′-Formylkynurenine</a></li> <li><a href="/wiki/Kynurenine" title="Kynurenine">Kynurenine</a></li> <li><a href="/wiki/Anthranilic_acid" title="Anthranilic acid">Anthranilic acid</a></li> <li><a href="/wiki/3-Hydroxykynurenine" title="3-Hydroxykynurenine">3-Hydroxykynurenine</a></li> <li><a href="/wiki/3-Hydroxyanthranilic_acid" title="3-Hydroxyanthranilic acid">3-Hydroxyanthranilic acid</a></li> <li><a href="/wiki/2-Amino-3-carboxymuconic_semialdehyde" title="2-Amino-3-carboxymuconic semialdehyde">2-Amino-3-carboxymuconic semialdehyde</a></li> <li><a href="/wiki/2-Aminomuconic_semialdehyde" title="2-Aminomuconic semialdehyde">2-Aminomuconic semialdehyde</a></li> <li><a href="/wiki/2-Aminomuconic_acid" title="2-Aminomuconic acid">2-Aminomuconic acid</a></li> <li><a href="/wiki/Glutaryl-CoA" title="Glutaryl-CoA">Glutaryl-CoA</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Glucogenic_amino_acid" title="Glucogenic amino acid">G</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">G→<a href="/wiki/Pyruvate" class="mw-redirect" title="Pyruvate">pyruvate</a>→ <br /><a href="/wiki/Citrate" class="mw-redirect" title="Citrate">citrate</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="glycine→serine→" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Glycine" title="Glycine">glycine</a>→<br /><a href="/wiki/Serine" title="Serine">serine</a>→</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/3-Phosphoglyceric_acid" title="3-Phosphoglyceric acid">3-Phosphoglyceric acid</a></li></ul> <ul><li><a href="/wiki/Glycine" title="Glycine">glycine</a>→<a href="/wiki/Creatine" title="Creatine">creatine</a>: <a href="/wiki/Glycocyamine" title="Glycocyamine">Glycocyamine</a></li> <li><a href="/wiki/Phosphocreatine" title="Phosphocreatine">Phosphocreatine</a></li> <li><a href="/wiki/Creatinine" title="Creatinine">Creatinine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">G→<a href="/wiki/Glutamate" class="mw-redirect" title="Glutamate">glutamate</a>→<br /><a href="/wiki/Alpha-Ketoglutaric_acid" class="mw-redirect" title="Alpha-Ketoglutaric acid">α-ketoglutarate</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Histidine" title="Histidine">histidine</a>→</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Urocanic_acid" title="Urocanic acid">Urocanic acid</a></li> <li><a href="/wiki/Imidazol-4-one-5-propionic_acid" title="Imidazol-4-one-5-propionic acid">Imidazol-4-one-5-propionic acid</a></li> <li><a href="/wiki/Formiminoglutamic_acid" title="Formiminoglutamic acid">Formiminoglutamic acid</a></li> <li><a href="/wiki/Glutamate-1-semialdehyde" title="Glutamate-1-semialdehyde">Glutamate-1-semialdehyde</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Proline" title="Proline">proline</a>→</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1-Pyrroline-5-carboxylic_acid" title="1-Pyrroline-5-carboxylic acid">1-Pyrroline-5-carboxylic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Arginine" title="Arginine">arginine</a>→</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Agmatine" title="Agmatine">Agmatine</a></li> <li><a href="/wiki/Ornithine" title="Ornithine">Ornithine</a></li> <li><a href="/wiki/Citrulline" title="Citrulline">Citrulline</a></li> <li><a href="/wiki/Cadaverine" title="Cadaverine">Cadaverine</a></li> <li><a href="/wiki/Putrescine" title="Putrescine">Putrescine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cysteine" title="Cysteine">cysteine</a>+<a href="/wiki/Glutamate" class="mw-redirect" title="Glutamate">glutamate</a>→<a href="/wiki/Glutathione" title="Glutathione">glutathione</a>: <a href="/wiki/Gamma-Glutamylcysteine" class="mw-redirect" title="Gamma-Glutamylcysteine">γ-Glutamylcysteine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">G→<a href="/wiki/Propionyl-CoA" title="Propionyl-CoA">propionyl-CoA</a>→<br /><a href="/wiki/Succinyl-CoA" title="Succinyl-CoA">succinyl-CoA</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Valine" title="Valine">valine</a>→</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alpha-Ketoisovaleric_acid" class="mw-redirect" title="Alpha-Ketoisovaleric acid">α-Ketoisovaleric acid</a></li> <li><a href="/wiki/Isobutyryl-CoA" title="Isobutyryl-CoA">Isobutyryl-CoA</a></li> <li><a href="/wiki/Methacrylyl-CoA" title="Methacrylyl-CoA">Methacrylyl-CoA</a></li> <li><a href="/wiki/3-Hydroxyisobutyryl-CoA" title="3-Hydroxyisobutyryl-CoA">3-Hydroxyisobutyryl-CoA</a></li> <li><a href="/wiki/3-Hydroxyisobutyric_acid" title="3-Hydroxyisobutyric acid">3-Hydroxyisobutyric acid</a></li> <li><a href="/wiki/2-Methyl-3-oxopropanoic_acid" class="mw-redirect" title="2-Methyl-3-oxopropanoic acid">2-Methyl-3-oxopropanoic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Isoleucine" title="Isoleucine">isoleucine</a>→</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2,3-Dihydroxy-3-methylpentanoic_acid" title="2,3-Dihydroxy-3-methylpentanoic acid">2,3-Dihydroxy-3-methylpentanoic acid</a></li> <li><a href="/wiki/2-Methylbutyryl-CoA" title="2-Methylbutyryl-CoA">2-Methylbutyryl-CoA</a></li> <li><a href="/wiki/Tiglyl-CoA" title="Tiglyl-CoA">Tiglyl-CoA</a></li> <li><a href="/wiki/2-Methylacetoacetyl-CoA" title="2-Methylacetoacetyl-CoA">2-Methylacetoacetyl-CoA</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Methionine" title="Methionine">methionine</a>→</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Methionine#Generation_of_homocysteine" title="Methionine">generation of homocysteine</a>:</i> <a href="/wiki/S-Adenosyl_methionine" title="S-Adenosyl methionine"><i>S</i>-Adenosyl methionine</a></li> <li><a href="/wiki/S-Adenosyl-L-homocysteine" title="S-Adenosyl-L-homocysteine"><i>S</i>-Adenosyl-<span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>-homocysteine</a></li> <li><a href="/wiki/Homocysteine" title="Homocysteine">Homocysteine</a></li></ul> <ul><li><i><a href="/wiki/Methionine#Conversion_to_cysteine" title="Methionine">conversion to cysteine</a>:</i> <a href="/wiki/Cystathionine" title="Cystathionine">Cystathionine</a></li> <li><a href="/wiki/Alpha-Ketobutyric_acid" class="mw-redirect" title="Alpha-Ketobutyric acid">α-Ketobutyric acid</a> + <a href="/wiki/Cysteine" title="Cysteine">Cysteine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Threonine" title="Threonine">threonine</a>→</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alpha-Ketobutyric_acid" class="mw-redirect" title="Alpha-Ketobutyric acid">α-Ketobutyric acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Propionyl-CoA" title="Propionyl-CoA">propionyl-CoA</a>→</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Methylmalonyl-CoA" title="Methylmalonyl-CoA">Methylmalonyl-CoA</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">G→<a href="/wiki/Fumarate" class="mw-redirect" title="Fumarate">fumarate</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phenylalanine" title="Phenylalanine">phenylalanine</a>→<a href="/wiki/Tyrosine" title="Tyrosine">tyrosine</a>→</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/4-Hydroxyphenylpyruvic_acid" title="4-Hydroxyphenylpyruvic acid">4-Hydroxyphenylpyruvic acid</a></li> <li><a href="/wiki/Homogentisic_acid" title="Homogentisic acid">Homogentisic acid</a></li> <li><a href="/wiki/4-Maleylacetoacetic_acid" title="4-Maleylacetoacetic acid">4-Maleylacetoacetic acid</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">G→<a href="/wiki/Oxaloacetate" class="mw-redirect" title="Oxaloacetate">oxaloacetate</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>see <a href="/wiki/Urea_cycle" title="Urea cycle">urea cycle</a></i></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cysteine_metabolism" title="Cysteine metabolism">Cysteine metabolism</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cysteine_sulfinic_acid" title="Cysteine sulfinic acid">Cysteine sulfinic acid</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Acetylcholine_receptor_modulators" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2" style="background:#e8e8ff;"><div id="Acetylcholine_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Acetylcholine_receptor" title="Acetylcholine receptor">Acetylcholine receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;font-size:114%"><div style="padding:0px"> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Muscarinic_acetylcholine_receptor_modulators" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Muscarinic_acetylcholine_receptor_modulators" title="Template:Muscarinic acetylcholine receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Muscarinic_acetylcholine_receptor_modulators" title="Template talk:Muscarinic acetylcholine receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Muscarinic_acetylcholine_receptor_modulators" title="Special:EditPage/Template:Muscarinic acetylcholine receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Muscarinic_acetylcholine_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Muscarinic_acetylcholine_receptor" title="Muscarinic acetylcholine receptor">Muscarinic acetylcholine receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Muscarinic_acetylcholine_receptors" class="mw-redirect" title="Muscarinic acetylcholine receptors"><abbr title="Muscarinic acetylcholine receptors">mAChRs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Muscarinic acetylcholine receptors</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Muscarinic_agonist" title="Muscarinic agonist">Agonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/77-LH-28-1" title="77-LH-28-1">77-LH-28-1</a></li> <li><a href="/wiki/AC-42" title="AC-42">AC-42</a></li> <li><a href="/w/index.php?title=AC-260,584&action=edit&redlink=1" class="new" title="AC-260,584 (page does not exist)">AC-260,584</a></li> <li><a href="/wiki/Aceclidine" title="Aceclidine">Aceclidine</a></li> <li><a href="/wiki/Acetylcholine" title="Acetylcholine">Acetylcholine</a></li> <li><a href="/w/index.php?title=AF30&action=edit&redlink=1" class="new" title="AF30 (page does not exist)">AF30</a></li> <li><a href="/w/index.php?title=AF150(S)&action=edit&redlink=1" class="new" title="AF150(S) (page does not exist)">AF150(S)</a></li> <li><a href="/w/index.php?title=AF267B&action=edit&redlink=1" class="new" title="AF267B (page does not exist)">AF267B</a></li> <li><a href="/wiki/Alvameline" title="Alvameline">Alvameline</a></li> <li><a href="/w/index.php?title=AQRA-741&action=edit&redlink=1" class="new" title="AQRA-741 (page does not exist)">AQRA-741</a></li> <li><a href="/wiki/Arecoline" title="Arecoline">Arecoline</a></li> <li><a href="/wiki/Bethanechol" title="Bethanechol">Bethanechol</a></li> <li><a href="/wiki/Butyrylcholine" title="Butyrylcholine">Butyrylcholine</a></li> <li><a href="/wiki/Carbachol" title="Carbachol">Carbachol</a></li> <li><a href="/w/index.php?title=CDD-0034&action=edit&redlink=1" class="new" title="CDD-0034 (page does not exist)">CDD-0034</a></li> <li><a href="/w/index.php?title=CDD-0078&action=edit&redlink=1" class="new" title="CDD-0078 (page does not exist)">CDD-0078</a></li> <li><a href="/w/index.php?title=CDD-0097&action=edit&redlink=1" class="new" title="CDD-0097 (page does not exist)">CDD-0097</a></li> <li><a href="/w/index.php?title=CDD-0098&action=edit&redlink=1" class="new" title="CDD-0098 (page does not exist)">CDD-0098</a></li> <li><a href="/w/index.php?title=CDD-0102&action=edit&redlink=1" class="new" title="CDD-0102 (page does not exist)">CDD-0102</a></li> <li><a href="/wiki/Cevimeline" title="Cevimeline">Cevimeline</a></li> <li><a href="/wiki/Choline" title="Choline">Choline</a></li> <li><a href="/wiki/Cis-Dioxolane" class="mw-redirect" title="Cis-Dioxolane">cis-Dioxolane</a></li> <li><a href="/wiki/Clozapine" title="Clozapine">Clozapine</a></li> <li><a href="/wiki/Desmethylclozapine" title="Desmethylclozapine">Desmethylclozapine (norclozapine)</a></li> <li><a href="/w/index.php?title=Ethoxysebacylcholine&action=edit&redlink=1" class="new" title="Ethoxysebacylcholine (page does not exist)">Ethoxysebacylcholine</a></li> <li><a href="/wiki/Itameline" title="Itameline">Itameline</a></li> <li><a href="/w/index.php?title=LY-593,039&action=edit&redlink=1" class="new" title="LY-593,039 (page does not exist)">LY-593,039</a></li> <li><a href="/w/index.php?title=L-689,660&action=edit&redlink=1" class="new" title="L-689,660 (page does not exist)">L-689,660</a></li> <li><a href="/w/index.php?title=LY-2,033,298&action=edit&redlink=1" class="new" title="LY-2,033,298 (page does not exist)">LY-2,033,298</a></li> <li><a href="/w/index.php?title=McNA343&action=edit&redlink=1" class="new" title="McNA343 (page does not exist)">McNA343</a></li> <li><a href="/wiki/Methacholine" title="Methacholine">Methacholine</a></li> <li><a href="/wiki/Milameline" title="Milameline">Milameline</a></li> <li><a href="/wiki/Muscarine" title="Muscarine">Muscarine</a></li> <li><a href="/w/index.php?title=NGX-267&action=edit&redlink=1" class="new" title="NGX-267 (page does not exist)">NGX-267</a></li> <li><a href="/w/index.php?title=Ocvimeline&action=edit&redlink=1" class="new" title="Ocvimeline (page does not exist)">Ocvimeline</a></li> <li><a href="/wiki/Oxotremorine" title="Oxotremorine">Oxotremorine</a></li> <li><a href="/w/index.php?title=PD-151,832&action=edit&redlink=1" class="new" title="PD-151,832 (page does not exist)">PD-151,832</a></li> <li><a href="/wiki/Pilocarpine" title="Pilocarpine">Pilocarpine</a></li> <li><a href="/w/index.php?title=RS86&action=edit&redlink=1" class="new" title="RS86 (page does not exist)">RS86</a></li> <li><a href="/wiki/Sabcomeline" title="Sabcomeline">Sabcomeline</a></li> <li><a href="/w/index.php?title=SDZ_210-086&action=edit&redlink=1" class="new" title="SDZ 210-086 (page does not exist)">SDZ 210-086</a></li> <li><a href="/w/index.php?title=Sebacylcholine&action=edit&redlink=1" class="new" title="Sebacylcholine (page does not exist)">Sebacylcholine</a></li> <li><a href="/w/index.php?title=Suberyldicholine&action=edit&redlink=1" class="new" title="Suberyldicholine (page does not exist)">Suberyldicholine</a></li> <li><a href="/wiki/Talsaclidine" title="Talsaclidine">Talsaclidine</a></li> <li><a href="/wiki/Tazomeline" title="Tazomeline">Tazomeline</a></li> <li><a href="/w/index.php?title=Thiopilocarpine&action=edit&redlink=1" class="new" title="Thiopilocarpine (page does not exist)">Thiopilocarpine</a></li> <li><a href="/wiki/Vedaclidine" title="Vedaclidine">Vedaclidine</a></li> <li><a href="/w/index.php?title=VU-0029767&action=edit&redlink=1" class="new" title="VU-0029767 (page does not exist)">VU-0029767</a></li> <li><a href="/w/index.php?title=VU-0090157&action=edit&redlink=1" class="new" title="VU-0090157 (page does not exist)">VU-0090157</a></li> <li><a href="/wiki/VU-0152099" title="VU-0152099">VU-0152099</a></li> <li><a href="/wiki/VU-0152100" title="VU-0152100">VU-0152100</a></li> <li><a href="/wiki/VU-0238429" title="VU-0238429">VU-0238429</a></li> <li><a href="/w/index.php?title=WAY-132,983&action=edit&redlink=1" class="new" title="WAY-132,983 (page does not exist)">WAY-132,983</a></li> <li><a href="/wiki/Xanomeline" title="Xanomeline">Xanomeline</a></li> <li><a href="/w/index.php?title=YM-796&action=edit&redlink=1" class="new" title="YM-796 (page does not exist)">YM-796</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Muscarinic_antagonist" title="Muscarinic antagonist">Antagonists</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/3-Quinuclidinyl_benzilate" title="3-Quinuclidinyl benzilate">3-Quinuclidinyl benzilate</a></li> <li><a href="/wiki/4-DAMP" title="4-DAMP">4-DAMP</a></li> <li><a href="/wiki/Aclidinium_bromide" title="Aclidinium bromide">Aclidinium bromide</a> (<a href="/wiki/Aclidinium_bromide/formoterol" title="Aclidinium bromide/formoterol">+formoterol</a>)</li> <li><a href="/wiki/Abediterol" title="Abediterol">Abediterol</a></li> <li><a href="/w/index.php?title=AF-DX_250&action=edit&redlink=1" class="new" title="AF-DX 250 (page does not exist)">AF-DX 250</a></li> <li><a href="/wiki/AFDX-384" title="AFDX-384">AF-DX 384</a></li> <li><a href="/wiki/Ambutonium_bromide" title="Ambutonium bromide">Ambutonium bromide</a></li> <li><a href="/wiki/Anisodamine" title="Anisodamine">Anisodamine</a></li> <li><a href="/wiki/Anisodine" title="Anisodine">Anisodine</a></li> <li><a href="/wiki/First-generation_antihistamine" class="mw-redirect" title="First-generation antihistamine">Antihistamines (first-generation)</a> (e.g., <a href="/wiki/Brompheniramine" title="Brompheniramine">brompheniramine</a>, <a href="/wiki/Buclizine" title="Buclizine">buclizine</a>, <a href="/wiki/Captodiame" title="Captodiame">captodiame</a>, <a href="/wiki/Chlorphenamine" title="Chlorphenamine">chlorphenamine (chlorpheniramine)</a>, <a href="/wiki/Cinnarizine" title="Cinnarizine">cinnarizine</a>, <a href="/wiki/Clemastine" title="Clemastine">clemastine</a>, <a href="/wiki/Cyproheptadine" title="Cyproheptadine">cyproheptadine</a>, <a href="/wiki/Dimenhydrinate" title="Dimenhydrinate">dimenhydrinate</a>, <a href="/wiki/Dimetindene" title="Dimetindene">dimetindene</a>, <a href="/wiki/Diphenhydramine" title="Diphenhydramine">diphenhydramine</a>, <a href="/wiki/Doxylamine" title="Doxylamine">doxylamine</a>, <a href="/wiki/Meclizine" title="Meclizine">meclizine</a>, <a href="/wiki/Mequitazine" title="Mequitazine">mequitazine</a>, <a href="/wiki/Perlapine" title="Perlapine">perlapine</a>, <a href="/wiki/Phenindamine" title="Phenindamine">phenindamine</a>, <a href="/wiki/Pheniramine" title="Pheniramine">pheniramine</a>, <a href="/wiki/Phenyltoloxamine" title="Phenyltoloxamine">phenyltoloxamine</a>, <a href="/wiki/Promethazine" title="Promethazine">promethazine</a>, <a href="/wiki/Propiomazine" title="Propiomazine">propiomazine</a>, <a href="/wiki/Triprolidine" title="Triprolidine">triprolidine</a>)</li> <li><a href="/w/index.php?title=AQ-RA_741&action=edit&redlink=1" class="new" title="AQ-RA 741 (page does not exist)">AQ-RA 741</a></li> <li><a href="/wiki/Atropine" title="Atropine">Atropine</a></li> <li><a href="/wiki/Atropine_methonitrate" class="mw-redirect" title="Atropine methonitrate">Atropine methonitrate</a></li> <li><a href="/wiki/Atypical_antipsychotic" title="Atypical antipsychotic">Atypical antipsychotics</a> (e.g., <a href="/wiki/Clozapine" title="Clozapine">clozapine</a>, <a href="/wiki/Fluperlapine" title="Fluperlapine">fluperlapine</a>, <a href="/wiki/Olanzapine" title="Olanzapine">olanzapine</a> (<a href="/wiki/Olanzapine/fluoxetine" title="Olanzapine/fluoxetine">+fluoxetine</a>), <a href="/w/index.php?title=Rilapine&action=edit&redlink=1" class="new" title="Rilapine (page does not exist)">rilapine</a>, <a href="/wiki/Quetiapine" title="Quetiapine">quetiapine</a>, <a href="/wiki/Tenilapine" title="Tenilapine">tenilapine</a>, <a href="/wiki/Zotepine" title="Zotepine">zotepine</a>)</li> <li><a href="/wiki/Benactyzine" title="Benactyzine">Benactyzine</a></li> <li><a href="/wiki/Benzatropine" title="Benzatropine">Benzatropine (benztropine)</a></li> <li><a href="/wiki/Benzilone" title="Benzilone">Benzilone</a></li> <li><a href="/wiki/Benzilylcholine_mustard" title="Benzilylcholine mustard">Benzilylcholine mustard</a></li> <li><a href="/wiki/Benzydamine" title="Benzydamine">Benzydamine</a></li> <li><a href="/wiki/Bevonium" title="Bevonium">Bevonium</a></li> <li><a href="/w/index.php?title=BIBN_99&action=edit&redlink=1" class="new" title="BIBN 99 (page does not exist)">BIBN 99</a></li> <li><a href="/wiki/Biperiden" title="Biperiden">Biperiden</a></li> <li><a href="/wiki/Bornaprine" title="Bornaprine">Bornaprine</a></li> <li><a href="/wiki/Camylofin" title="Camylofin">Camylofin</a></li> <li><a href="/wiki/CAR-226,086" title="CAR-226,086">CAR-226,086</a></li> <li><a href="/wiki/CAR-301,060" title="CAR-301,060">CAR-301,060</a></li> <li><a href="/wiki/CAR-302,196" title="CAR-302,196">CAR-302,196</a></li> <li><a href="/wiki/CAR-302,282" title="CAR-302,282">CAR-302,282</a></li> <li><a href="/w/index.php?title=CAR-302,368&action=edit&redlink=1" class="new" title="CAR-302,368 (page does not exist)">CAR-302,368</a></li> <li><a href="/w/index.php?title=CAR-302,537&action=edit&redlink=1" class="new" title="CAR-302,537 (page does not exist)">CAR-302,537</a></li> <li><a href="/wiki/CAR-302,668" title="CAR-302,668">CAR-302,668</a></li> <li><a href="/wiki/Caramiphen" title="Caramiphen">Caramiphen</a></li> <li><a href="/wiki/Cimetropium_bromide" title="Cimetropium bromide">Cimetropium bromide</a></li> <li><a href="/wiki/Clidinium_bromide" title="Clidinium bromide">Clidinium bromide</a></li> <li><a href="/wiki/Cloperastine" title="Cloperastine">Cloperastine</a></li> <li><a href="/wiki/CS-27349" title="CS-27349">CS-27349</a></li> <li><a href="/wiki/Cyclobenzaprine" title="Cyclobenzaprine">Cyclobenzaprine</a></li> <li><a href="/wiki/Cyclopentolate" title="Cyclopentolate">Cyclopentolate</a></li> <li><a href="/wiki/Darifenacin" title="Darifenacin">Darifenacin</a></li> <li><a href="/w/index.php?title=DAU-5884&action=edit&redlink=1" class="new" title="DAU-5884 (page does not exist)">DAU-5884</a></li> <li><a href="/wiki/Desfesoterodine" title="Desfesoterodine">Desfesoterodine</a></li> <li><a href="/wiki/Dexetimide" title="Dexetimide">Dexetimide</a></li> <li><a href="/w/index.php?title=DIBD&action=edit&redlink=1" class="new" title="DIBD (page does not exist)">DIBD</a></li> <li><a href="/wiki/Dicycloverine" title="Dicycloverine">Dicycloverine (dicyclomine)</a></li> <li><a href="/wiki/Dihexyverine" title="Dihexyverine">Dihexyverine</a></li> <li><a href="/wiki/Difemerine" title="Difemerine">Difemerine</a></li> <li><a href="/wiki/Diphemanil_metilsulfate" title="Diphemanil metilsulfate">Diphemanil metilsulfate</a></li> <li><a href="/wiki/Ditran" title="Ditran">Ditran</a></li> <li><a href="/wiki/Drofenine" title="Drofenine">Drofenine</a></li> <li><a href="/wiki/EA-3167" title="EA-3167">EA-3167</a></li> <li><a href="/wiki/EA-3443" title="EA-3443">EA-3443</a></li> <li><a href="/wiki/EA-3580" title="EA-3580">EA-3580</a></li> <li><a href="/wiki/EA-3834" title="EA-3834">EA-3834</a></li> <li><a href="/wiki/Emepronium_bromide" title="Emepronium bromide">Emepronium bromide</a></li> <li><a href="/wiki/Etanautine" title="Etanautine">Etanautine</a></li> <li><a href="/wiki/Etybenzatropine" title="Etybenzatropine">Etybenzatropine (ethybenztropine)</a></li> <li><a href="/wiki/Fenpiverinium" title="Fenpiverinium">Fenpiverinium</a></li> <li><a href="/wiki/Fentonium_bromide" title="Fentonium bromide">Fentonium bromide</a></li> <li><a href="/wiki/Fesoterodine" title="Fesoterodine">Fesoterodine</a></li> <li><a href="/wiki/Flavoxate" title="Flavoxate">Flavoxate</a></li> <li><a href="/wiki/Glycopyrronium_bromide" title="Glycopyrronium bromide">Glycopyrronium bromide</a> (<a href="/wiki/Beclometasone/formoterol/glycopyrronium_bromide" title="Beclometasone/formoterol/glycopyrronium bromide">+beclometasone/formoterol</a>, <a href="/wiki/Indacaterol/glycopyrronium_bromide" title="Indacaterol/glycopyrronium bromide">+indacaterol</a>, <a href="/wiki/Neostigmine/glycopyrronium_bromide" title="Neostigmine/glycopyrronium bromide">+neostigmine</a>)</li> <li><a href="/w/index.php?title=Hexahydrodifenidol&action=edit&redlink=1" class="new" title="Hexahydrodifenidol (page does not exist)">Hexahydrodifenidol</a></li> <li><a href="/w/index.php?title=Hexahydrosiladifenidol&action=edit&redlink=1" class="new" title="Hexahydrosiladifenidol (page does not exist)">Hexahydrosiladifenidol</a></li> <li><a href="/w/index.php?title=Hexbutinol&action=edit&redlink=1" class="new" title="Hexbutinol (page does not exist)">Hexbutinol</a></li> <li><a href="/wiki/Hexocyclium" title="Hexocyclium">Hexocyclium</a></li> <li><a href="/wiki/Himbacine" title="Himbacine">Himbacine</a></li> <li><a href="/w/index.php?title=HL-031,120&action=edit&redlink=1" class="new" title="HL-031,120 (page does not exist)">HL-031,120</a></li> <li><a href="/wiki/Homatropine" title="Homatropine">Homatropine</a></li> <li><a href="/wiki/Imidafenacin" title="Imidafenacin">Imidafenacin</a></li> <li><a href="/wiki/Ipratropium_bromide" title="Ipratropium bromide">Ipratropium bromide</a> (<a href="/wiki/Ipratropium_bromide/salbutamol" title="Ipratropium bromide/salbutamol">+salbutamol</a>)</li> <li><a href="/wiki/Isopropamide" title="Isopropamide">Isopropamide</a></li> <li><a href="/w/index.php?title=J-104,129&action=edit&redlink=1" class="new" title="J-104,129 (page does not exist)">J-104,129</a></li> <li><a href="/wiki/Hyoscyamine" title="Hyoscyamine">Hyoscyamine</a></li> <li><a href="/wiki/Mamba#Mamba_toxins" title="Mamba">Mamba toxin 3</a></li> <li><a href="/wiki/Mamba#Mamba_toxins" title="Mamba">Mamba toxin 7</a></li> <li><a href="/wiki/Mazaticol" title="Mazaticol">Mazaticol</a></li> <li><a href="/wiki/Mebeverine" title="Mebeverine">Mebeverine</a></li> <li><a href="/wiki/Meladrazine" title="Meladrazine">Meladrazine</a></li> <li><a href="/wiki/Mepenzolate" title="Mepenzolate">Mepenzolate</a></li> <li><a href="/wiki/Methantheline" title="Methantheline">Methantheline</a></li> <li><a href="/wiki/Methoctramine" title="Methoctramine">Methoctramine</a></li> <li><a href="/wiki/Methylatropine" title="Methylatropine">Methylatropine</a></li> <li><a href="/wiki/Methylhomatropine" class="mw-redirect" title="Methylhomatropine">Methylhomatropine</a></li> <li><a href="/wiki/Methylscopolamine_bromide" title="Methylscopolamine bromide">Methylscopolamine</a></li> <li><a href="/wiki/Metixene" title="Metixene">Metixene</a></li> <li><a href="/wiki/Muscarinic_toxin_7" title="Muscarinic toxin 7">Muscarinic toxin 7</a></li> <li><a href="/wiki/N-Ethyl-3-piperidyl_benzilate" title="N-Ethyl-3-piperidyl benzilate">N-Ethyl-3-piperidyl benzilate</a></li> <li><a href="/wiki/N-Methyl-3-piperidyl_benzilate" title="N-Methyl-3-piperidyl benzilate">N-Methyl-3-piperidyl benzilate</a></li> <li><a href="/wiki/Nefopam" title="Nefopam">Nefopam</a></li> <li><a href="/wiki/Octatropine_methylbromide" title="Octatropine methylbromide">Octatropine methylbromide (anisotropine methylbromide)</a></li> <li><a href="/wiki/Orphenadrine" title="Orphenadrine">Orphenadrine</a></li> <li><a href="/wiki/Otenzepad" title="Otenzepad">Otenzepad (AF-DX 116)</a></li> <li><a href="/wiki/Otilonium_bromide" title="Otilonium bromide">Otilonium bromide</a></li> <li><a href="/wiki/Oxapium_iodide" title="Oxapium iodide">Oxapium iodide</a></li> <li><a href="/wiki/Oxitropium_bromide" title="Oxitropium bromide">Oxitropium bromide</a></li> <li><a href="/wiki/Oxybutynin" title="Oxybutynin">Oxybutynin</a></li> <li><a href="/wiki/Oxyphencyclimine" title="Oxyphencyclimine">Oxyphencyclimine</a></li> <li><a href="/wiki/Oxyphenonium_bromide" title="Oxyphenonium bromide">Oxyphenonium bromide</a></li> <li><a href="/w/index.php?title=PBID&action=edit&redlink=1" class="new" title="PBID (page does not exist)">PBID</a></li> <li><a href="/wiki/PD-102,807" title="PD-102,807">PD-102,807</a></li> <li><a href="/wiki/PD-0298029" title="PD-0298029">PD-0298029</a></li> <li><a href="/wiki/Penthienate" title="Penthienate">Penthienate</a></li> <li><a href="/wiki/Pethidine" title="Pethidine">Pethidine</a></li> <li><a href="/w/index.php?title=PFHHSiD&action=edit&redlink=1" class="new" title="PFHHSiD (page does not exist)">pFHHSiD</a></li> <li><a href="/wiki/Phenglutarimide" title="Phenglutarimide">Phenglutarimide</a></li> <li><a href="/wiki/Phenyltoloxamine" title="Phenyltoloxamine">Phenyltoloxamine</a></li> <li><a href="/wiki/Pipenzolate_bromide" title="Pipenzolate bromide">Pipenzolate bromide</a></li> <li><a href="/wiki/Piperidolate" title="Piperidolate">Piperidolate</a></li> <li><a href="/wiki/Pirenzepine" title="Pirenzepine">Pirenzepine</a></li> <li><a href="/wiki/Piroheptine" title="Piroheptine">Piroheptine</a></li> <li><a href="/wiki/Pizotifen" title="Pizotifen">Pizotifen</a></li> <li><a href="/wiki/Poldine" title="Poldine">Poldine</a></li> <li><a href="/wiki/Pridinol" title="Pridinol">Pridinol</a></li> <li><a href="/wiki/Prifinium_bromide" title="Prifinium bromide">Prifinium bromide</a></li> <li><a href="/wiki/Procyclidine" title="Procyclidine">Procyclidine</a></li> <li><a href="/wiki/Profenamine" title="Profenamine">Profenamine (ethopropazine)</a></li> <li><a href="/wiki/Propantheline_bromide" title="Propantheline bromide">Propantheline bromide</a></li> <li><a href="/wiki/Propiverine" title="Propiverine">Propiverine</a></li> <li><a href="/wiki/Quinidine" title="Quinidine">Quinidine</a></li> <li><a href="/wiki/3-Quinuclidinyl_thiochromane-4-carboxylate" title="3-Quinuclidinyl thiochromane-4-carboxylate">3-Quinuclidinyl thiochromane-4-carboxylate</a></li> <li><a href="/wiki/Revefenacin" title="Revefenacin">Revefenacin</a></li> <li><a href="/wiki/Rociverine" title="Rociverine">Rociverine</a></li> <li><a href="/w/index.php?title=RU-47,213&action=edit&redlink=1" class="new" title="RU-47,213 (page does not exist)">RU-47,213</a></li> <li><a href="/w/index.php?title=SCH-57,790&action=edit&redlink=1" class="new" title="SCH-57,790 (page does not exist)">SCH-57,790</a></li> <li><a href="/w/index.php?title=SCH-72,788&action=edit&redlink=1" class="new" title="SCH-72,788 (page does not exist)">SCH-72,788</a></li> <li><a href="/w/index.php?title=SCH-217,443&action=edit&redlink=1" class="new" title="SCH-217,443 (page does not exist)">SCH-217,443</a></li> <li><a href="/wiki/Hyoscine" class="mw-redirect" title="Hyoscine">Scopolamine (hyoscine)</a></li> <li><a href="/wiki/Hyoscine_butylbromide" title="Hyoscine butylbromide">Scopolamine butylbromide (hyoscine butylbromide)</a></li> <li><a href="/w/index.php?title=Silahexacyclium&action=edit&redlink=1" class="new" title="Silahexacyclium (page does not exist)">Silahexacyclium</a></li> <li><a href="/wiki/Sofpironium_bromide" title="Sofpironium bromide">Sofpironium bromide</a></li> <li><a href="/wiki/Solifenacin" title="Solifenacin">Solifenacin</a></li> <li><a href="/wiki/Selective_serotonin_reuptake_inhibitors" class="mw-redirect" title="Selective serotonin reuptake inhibitors"><abbr title="Selective serotonin reuptake inhibitors">SSRIs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Selective serotonin reuptake inhibitors</span> (e.g., <a href="/wiki/Femoxetine" title="Femoxetine">femoxetine</a>, <a href="/wiki/Paroxetine" title="Paroxetine">paroxetine</a>)</li> <li><a href="/wiki/Telenzepine" title="Telenzepine">Telenzepine</a></li> <li><a href="/wiki/Terodiline" title="Terodiline">Terodiline</a></li> <li><a href="/wiki/Tetracyclic_antidepressant" title="Tetracyclic antidepressant">Tetracyclic antidepressants</a> (e.g., <a href="/wiki/Amoxapine" title="Amoxapine">amoxapine</a>, <a href="/wiki/Maprotiline" title="Maprotiline">maprotiline</a>, <a href="/wiki/Mianserin" title="Mianserin">mianserin</a>, <a href="/wiki/Mirtazapine" title="Mirtazapine">mirtazapine</a>)</li> <li><a href="/wiki/Tiemonium_iodide" title="Tiemonium iodide">Tiemonium iodide</a></li> <li><a href="/wiki/Timepidium_bromide" title="Timepidium bromide">Timepidium bromide</a></li> <li><a href="/wiki/Tiotropium_bromide" title="Tiotropium bromide">Tiotropium bromide</a></li> <li><a href="/w/index.php?title=Tiquizium_bromide&action=edit&redlink=1" class="new" title="Tiquizium bromide (page does not exist)">Tiquizium bromide</a></li> <li><a href="/wiki/Tofenacin" title="Tofenacin">Tofenacin</a></li> <li><a href="/wiki/Tolterodine" title="Tolterodine">Tolterodine</a></li> <li><a href="/wiki/Tricyclic_antidepressant" title="Tricyclic antidepressant">Tricyclic antidepressants</a> (e.g., <a href="/wiki/Amitriptyline" title="Amitriptyline">amitriptyline</a> (<a href="/wiki/Amitriptyline/perphenazine" title="Amitriptyline/perphenazine">+perphenazine</a>), <a href="/wiki/Amitriptylinoxide" title="Amitriptylinoxide">amitriptylinoxide</a>, <a href="/wiki/Butriptyline" title="Butriptyline">butriptyline</a>, <a href="/wiki/Cidoxepin" title="Cidoxepin">cidoxepin</a>, <a href="/wiki/Clomipramine" title="Clomipramine">clomipramine</a>, <a href="/wiki/Desipramine" title="Desipramine">desipramine</a>, <a href="/w/index.php?title=Desmethyldesipramine&action=edit&redlink=1" class="new" title="Desmethyldesipramine (page does not exist)">desmethyldesipramine</a>, <a href="/wiki/Dibenzepin" title="Dibenzepin">dibenzepin</a>, <a href="/wiki/Dosulepin" title="Dosulepin">dosulepin (dothiepin)</a>, <a href="/wiki/Doxepin" title="Doxepin">doxepin</a>, <a href="/wiki/Imipramine" title="Imipramine">imipramine</a>, <a href="/wiki/Lofepramine" title="Lofepramine">lofepramine</a>, <a href="/wiki/Nitroxazepine" title="Nitroxazepine">nitroxazepine</a>, <a href="/wiki/Northiaden" title="Northiaden">northiaden (desmethyldosulepin)</a>, <a href="/wiki/Nortriptyline" title="Nortriptyline">nortriptyline</a>, <a href="/wiki/Protriptyline" title="Protriptyline">protriptyline</a>, <a href="/wiki/Quinupramine" title="Quinupramine">quinupramine</a>, <a href="/wiki/Trimipramine" title="Trimipramine">trimipramine</a>)</li> <li><a href="/wiki/Tridihexethyl" title="Tridihexethyl">Tridihexethyl</a></li> <li><a href="/wiki/Trihexyphenidyl" title="Trihexyphenidyl">Trihexyphenidyl</a></li> <li><a href="/wiki/Trimebutine" title="Trimebutine">Trimebutine</a></li> <li><a href="/wiki/Tripitamine" class="mw-redirect" title="Tripitamine">Tripitamine (tripitramine)</a></li> <li><a href="/w/index.php?title=Tropacine&action=edit&redlink=1" class="new" title="Tropacine (page does not exist)">Tropacine</a></li> <li><a href="/wiki/Tropatepine" title="Tropatepine">Tropatepine</a></li> <li><a href="/wiki/Tropicamide" title="Tropicamide">Tropicamide</a></li> <li><a href="/wiki/Trospium_chloride" title="Trospium chloride">Trospium chloride</a></li> <li><a href="/wiki/Typical_antipsychotic" title="Typical antipsychotic">Typical antipsychotics</a> (e.g., <a href="/wiki/Chlorpromazine" title="Chlorpromazine">chlorpromazine</a>, <a href="/wiki/Chlorprothixene" title="Chlorprothixene">chlorprothixene</a>, <a href="/wiki/Cyamemazine" title="Cyamemazine">cyamemazine (cyamepromazine)</a>, <a href="/wiki/Loxapine" title="Loxapine">loxapine</a>, <a href="/wiki/Mesoridazine" title="Mesoridazine">mesoridazine</a>, <a href="/wiki/Thioridazine" title="Thioridazine">thioridazine</a>)</li> <li><a href="/wiki/Umeclidinium_bromide" title="Umeclidinium bromide">Umeclidinium bromide</a> (<a href="/wiki/Umeclidinium_bromide/vilanterol" title="Umeclidinium bromide/vilanterol">+vilanterol</a>)</li> <li><a href="/wiki/WIN-2299" title="WIN-2299">WIN-2299</a></li> <li><a href="/wiki/Xanomeline" title="Xanomeline">Xanomeline</a></li> <li><a href="/w/index.php?title=Zamifenacin&action=edit&redlink=1" class="new" title="Zamifenacin (page does not exist)">Zamifenacin</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Precursor_(chemistry)" title="Precursor (chemistry)">Precursors</a><br /><small>(and <a href="/wiki/Prodrug" title="Prodrug">prodrugs</a>)</small></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetyl-coA" class="mw-redirect" title="Acetyl-coA">Acetyl-coA</a></li> <li><a href="/wiki/Adafenoxate" title="Adafenoxate">Adafenoxate</a></li> <li><a href="/wiki/Choline" title="Choline">Choline</a> (<a href="/wiki/Lecithin" title="Lecithin">lecithin</a>)</li> <li><a href="/wiki/Citicoline" title="Citicoline">Citicoline</a></li> <li><a href="/wiki/Cyprodenate" title="Cyprodenate">Cyprodenate</a></li> <li><a href="/wiki/Dimethylethanolamine" title="Dimethylethanolamine">Dimethylethanolamine</a></li> <li><a href="/wiki/Glycerophosphocholine" class="mw-redirect" title="Glycerophosphocholine">Glycerophosphocholine</a></li> <li><a href="/wiki/Meclofenoxate" title="Meclofenoxate">Meclofenoxate (centrophenoxine)</a></li> <li><a href="/wiki/Phosphatidylcholine" title="Phosphatidylcholine">Phosphatidylcholine</a></li> <li><a href="/wiki/Phosphatidylethanolamine" title="Phosphatidylethanolamine">Phosphatidylethanolamine</a></li> <li><a href="/wiki/Phosphorylcholine" title="Phosphorylcholine">Phosphorylcholine</a></li> <li><a href="/wiki/Pirisudanol" title="Pirisudanol">Pirisudanol</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></dd> <dd><a href="/wiki/Template:Nicotinic_acetylcholine_receptor_modulators" title="Template:Nicotinic acetylcholine receptor modulators">Nicotinic acetylcholine receptor modulators</a></dd> <dd><a href="/wiki/Template:Acetylcholine_metabolism_and_transport_modulators" title="Template:Acetylcholine metabolism and transport modulators">Acetylcholine metabolism/transport modulators</a></dd></dl> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Nicotinic_acetylcholine_receptor_modulators" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Nicotinic_acetylcholine_receptor_modulators" title="Template:Nicotinic acetylcholine receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Nicotinic_acetylcholine_receptor_modulators" title="Template talk:Nicotinic acetylcholine receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Nicotinic_acetylcholine_receptor_modulators" title="Special:EditPage/Template:Nicotinic acetylcholine receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Nicotinic_acetylcholine_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Nicotinic_acetylcholine_receptor" title="Nicotinic acetylcholine receptor">Nicotinic acetylcholine receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Nicotinic_acetylcholine_receptors" class="mw-redirect" title="Nicotinic acetylcholine receptors"><abbr title="Nicotinic acetylcholine receptors">nAChRs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Nicotinic acetylcholine receptors</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Receptor_agonist" class="mw-redirect" title="Receptor agonist">Agonists</a><br />(and <a href="/wiki/Positive_allosteric_modulators" class="mw-redirect" title="Positive allosteric modulators"><abbr title="positive allosteric modulators">PAMs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip positive allosteric modulators</span>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/5-Hydroxyindoleacetic_acid" title="5-Hydroxyindoleacetic acid">5-HIAA</a></li> <li><a href="/wiki/6-Chloronicotine" title="6-Chloronicotine">6-Chloronicotine</a></li> <li><a href="/wiki/A-84,543" title="A-84,543">A-84,543</a></li> <li><a href="/wiki/A-366,833" title="A-366,833">A-366,833</a></li> <li><a href="/w/index.php?title=A-582,941&action=edit&redlink=1" class="new" title="A-582,941 (page does not exist)">A-582,941</a></li> <li><a href="/w/index.php?title=A-867,744&action=edit&redlink=1" class="new" title="A-867,744 (page does not exist)">A-867,744</a></li> <li><a href="/wiki/ABT-202" title="ABT-202">ABT-202</a></li> <li><a href="/wiki/ABT-418" title="ABT-418">ABT-418</a></li> <li><a href="/w/index.php?title=ABT-560&action=edit&redlink=1" class="new" title="ABT-560 (page does not exist)">ABT-560</a></li> <li><a href="/w/index.php?title=ABT-894&action=edit&redlink=1" class="new" title="ABT-894 (page does not exist)">ABT-894</a></li> <li><a href="/wiki/Acetylcholine" title="Acetylcholine">Acetylcholine</a></li> <li><a href="/wiki/Altinicline" title="Altinicline">Altinicline</a></li> <li><a href="/wiki/Anabasine" title="Anabasine">Anabasine</a></li> <li><a href="/wiki/Anatabine" title="Anatabine">Anatabine</a></li> <li><a href="/wiki/Anatoxin-a" title="Anatoxin-a">Anatoxin-a</a></li> <li><a href="/wiki/AR-R17779" title="AR-R17779">AR-R17779</a></li> <li><a href="/wiki/Bephenium_hydroxynaphthoate" title="Bephenium hydroxynaphthoate">Bephenium hydroxynaphthoate</a></li> <li><a href="/wiki/Butinoline" title="Butinoline">Butinoline</a></li> <li><a href="/wiki/Butyrylcholine" title="Butyrylcholine">Butyrylcholine</a></li> <li><a href="/wiki/Carbachol" title="Carbachol">Carbachol</a></li> <li><a href="/wiki/Choline" title="Choline">Choline</a></li> <li><a href="/wiki/Cotinine" title="Cotinine">Cotinine</a></li> <li><a href="/wiki/Cytisine" title="Cytisine">Cytisine</a></li> <li><a href="/wiki/Decamethonium" title="Decamethonium">Decamethonium</a></li> <li><a href="/wiki/Desformylflustrabromine" title="Desformylflustrabromine">Desformylflustrabromine</a></li> <li><a href="/wiki/Dianicline" title="Dianicline">Dianicline</a></li> <li><a href="/wiki/Dimethylphenylpiperazinium" title="Dimethylphenylpiperazinium">Dimethylphenylpiperazinium</a></li> <li><a href="/wiki/Epibatidine" title="Epibatidine">Epibatidine</a></li> <li><a href="/wiki/Epiboxidine" title="Epiboxidine">Epiboxidine</a></li> <li><a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">Ethanol (alcohol)</a></li> <li><a href="/w/index.php?title=Ethoxysebacylcholine&action=edit&redlink=1" class="new" title="Ethoxysebacylcholine (page does not exist)">Ethoxysebacylcholine</a></li> <li><a href="/w/index.php?title=EVP-4473&action=edit&redlink=1" class="new" title="EVP-4473 (page does not exist)">EVP-4473</a></li> <li><a href="/wiki/EVP-6124" class="mw-redirect" title="EVP-6124">EVP-6124</a></li> <li><a href="/wiki/Galantamine" title="Galantamine">Galantamine</a></li> <li><a href="/wiki/GTS-21" title="GTS-21">GTS-21</a></li> <li><a href="/wiki/Ispronicline" title="Ispronicline">Ispronicline</a></li> <li><a href="/wiki/Ivermectin" title="Ivermectin">Ivermectin</a></li> <li><a href="/wiki/JNJ-39393406" title="JNJ-39393406">JNJ-39393406</a></li> <li><a href="/wiki/Levamisole" title="Levamisole">Levamisole</a></li> <li><a href="/wiki/Lobeline" title="Lobeline">Lobeline</a></li> <li><a href="/w/index.php?title=MEM-63,908&action=edit&redlink=1" class="new" title="MEM-63,908 (page does not exist)">MEM-63,908 (RG-3487)</a></li> <li><a href="/wiki/Morantel" title="Morantel">Morantel</a></li> <li><a href="/wiki/Nicotine" title="Nicotine">Nicotine</a> (<a href="/wiki/Tobacco" title="Tobacco">tobacco</a>)</li> <li><a href="/w/index.php?title=NS-1738&action=edit&redlink=1" class="new" title="NS-1738 (page does not exist)">NS-1738</a></li> <li><a href="/wiki/PHA-543,613" title="PHA-543,613">PHA-543,613</a></li> <li><a href="/w/index.php?title=PHA-709,829&action=edit&redlink=1" class="new" title="PHA-709,829 (page does not exist)">PHA-709,829</a></li> <li><a href="/wiki/PNU-120,596" title="PNU-120,596">PNU-120,596</a></li> <li><a href="/wiki/PNU-282,987" title="PNU-282,987">PNU-282,987</a></li> <li><a href="/wiki/Pozanicline" title="Pozanicline">Pozanicline</a></li> <li><a href="/wiki/Pyrantel" title="Pyrantel">Pyrantel</a></li> <li><a href="/wiki/Rivanicline" title="Rivanicline">Rivanicline</a></li> <li><a href="/wiki/RJR-2429" title="RJR-2429">RJR-2429</a></li> <li><a href="/wiki/Sazetidine_A" title="Sazetidine A">Sazetidine A</a></li> <li><a href="/wiki/SB-206553" title="SB-206553">SB-206553</a></li> <li><a href="/w/index.php?title=Sebacylcholine&action=edit&redlink=1" class="new" title="Sebacylcholine (page does not exist)">Sebacylcholine</a></li> <li><a href="/wiki/SIB-1508Y" class="mw-redirect" title="SIB-1508Y">SIB-1508Y</a></li> <li><a href="/wiki/SIB-1553A" title="SIB-1553A">SIB-1553A</a></li> <li><a href="/wiki/SSR-180,711" title="SSR-180,711">SSR-180,711</a></li> <li><a href="/w/index.php?title=Suberyldicholine&action=edit&redlink=1" class="new" title="Suberyldicholine (page does not exist)">Suberyldicholine</a></li> <li><a href="/wiki/Suxamethonium" class="mw-redirect" title="Suxamethonium">Suxamethonium (succinylcholine)</a></li> <li><a href="/wiki/Suxethonium_chloride" title="Suxethonium chloride">Suxethonium (succinyldicholine)</a></li> <li><a href="/wiki/TC-1698" title="TC-1698">TC-1698</a></li> <li><a href="/w/index.php?title=TC-1734&action=edit&redlink=1" class="new" title="TC-1734 (page does not exist)">TC-1734</a></li> <li><a href="/wiki/TC-1827" title="TC-1827">TC-1827</a></li> <li><a href="/wiki/TC-2216" title="TC-2216">TC-2216</a></li> <li><a href="/wiki/TC-5214" class="mw-redirect" title="TC-5214">TC-5214</a></li> <li><a href="/wiki/TC-5619" class="mw-redirect" title="TC-5619">TC-5619</a></li> <li><a href="/w/index.php?title=TC-6683&action=edit&redlink=1" class="new" title="TC-6683 (page does not exist)">TC-6683</a></li> <li><a href="/wiki/Tebanicline" title="Tebanicline">Tebanicline</a></li> <li><a href="/wiki/Tribendimidine" title="Tribendimidine">Tribendimidine</a></li> <li><a href="/wiki/Tropisetron" title="Tropisetron">Tropisetron</a></li> <li><a href="/wiki/UB-165" title="UB-165">UB-165</a></li> <li><a href="/wiki/Varenicline" title="Varenicline">Varenicline</a></li> <li><a href="/wiki/WAY-317,538" class="mw-redirect" title="WAY-317,538">WAY-317,538</a></li> <li><a href="/w/index.php?title=XY-4083&action=edit&redlink=1" class="new" title="XY-4083 (page does not exist)">XY-4083</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Receptor_antagonist" title="Receptor antagonist">Antagonists</a><br />(and <a href="/wiki/Negative_allosteric_modulators" class="mw-redirect" title="Negative allosteric modulators"><abbr title="negative allosteric modulators">NAMs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip negative allosteric modulators</span>)</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/18-Methylaminocoronaridine" title="18-Methylaminocoronaridine">18-MAC</a></li> <li><a href="/wiki/18-Methoxycoronaridine" title="18-Methoxycoronaridine">18-MC</a></li> <li><a href="/wiki/%CE%91-Neurotoxin" title="Α-Neurotoxin">α-Neurotoxins</a> (e.g., <a href="/wiki/%CE%91-bungarotoxin" class="mw-redirect" title="Α-bungarotoxin">α-bungarotoxin</a>, <a href="/wiki/%CE%91-cobratoxin" class="mw-redirect" title="Α-cobratoxin">α-cobratoxin</a>, <a href="/wiki/%CE%91-conotoxin" class="mw-redirect" title="Α-conotoxin">α-conotoxin</a>, many others)</li> <li><a href="/w/index.php?title=ABT-126&action=edit&redlink=1" class="new" title="ABT-126 (page does not exist)">ABT-126</a></li> <li><a href="/wiki/Alcuronium" class="mw-redirect" title="Alcuronium">Alcuronium</a></li> <li><a href="/wiki/Allopregnanolone" title="Allopregnanolone">Allopregnanolone</a></li> <li><a href="/wiki/Amantadine" title="Amantadine">Amantadine</a></li> <li><a href="/w/index.php?title=Anatruxonium&action=edit&redlink=1" class="new" title="Anatruxonium (page does not exist)">Anatruxonium</a></li> <li><a href="/w/index.php?title=AQW051&action=edit&redlink=1" class="new" title="AQW051 (page does not exist)">AQW051</a></li> <li><a href="/wiki/Atracurium" class="mw-redirect" title="Atracurium">Atracurium</a></li> <li><a href="/wiki/Barbiturates" class="mw-redirect" title="Barbiturates">Barbiturates</a> (e.g., <a href="/wiki/Pentobarbital" title="Pentobarbital">pentobarbital</a>, <a href="/wiki/Sodium_thiopental" title="Sodium thiopental">sodium thiopental</a>)</li> <li><a href="/wiki/BNC-210" title="BNC-210">BNC-210</a></li> <li><a href="/wiki/Bungarotoxin" title="Bungarotoxin">Bungarotoxins</a> (e.g., <a href="/wiki/%CE%91-bungarotoxin" class="mw-redirect" title="Α-bungarotoxin">α-bungarotoxin</a>, <a href="/wiki/%CE%9A-bungarotoxin" class="mw-redirect" title="Κ-bungarotoxin">κ-bungarotoxin</a>)</li> <li><a href="/wiki/Bupropion" title="Bupropion">Bupropion</a></li> <li><a href="/wiki/BW284C51" title="BW284C51">BW284C51</a></li> <li><a href="/wiki/BW-A444" title="BW-A444">BW-A444</a></li> <li><a href="/wiki/Candocuronium_iodide" title="Candocuronium iodide">Candocuronium iodide (chandonium iodide)</a></li> <li><a href="/wiki/Chlorisondamine" title="Chlorisondamine">Chlorisondamine</a></li> <li><a href="/wiki/Cisatracurium" class="mw-redirect" title="Cisatracurium">Cisatracurium</a></li> <li><a href="/wiki/Coclaurine" title="Coclaurine">Coclaurine</a></li> <li><a href="/wiki/Coronaridine" title="Coronaridine">Coronaridine</a></li> <li><a href="/wiki/Curare" title="Curare">Curare</a></li> <li><a href="/wiki/Cyclopropane" title="Cyclopropane">Cyclopropane</a></li> <li><a href="/wiki/Dacuronium_bromide" title="Dacuronium bromide">Dacuronium bromide</a></li> <li><a href="/wiki/Decamethonium" title="Decamethonium">Decamethonium</a></li> <li><a href="/wiki/Dehydronorketamine" title="Dehydronorketamine">Dehydronorketamine</a></li> <li><a href="/wiki/Desflurane" title="Desflurane">Desflurane</a></li> <li><a href="/wiki/Dextromethorphan" title="Dextromethorphan">Dextromethorphan</a></li> <li><a href="/wiki/Dextropropoxyphene" title="Dextropropoxyphene">Dextropropoxyphene</a></li> <li><a href="/wiki/Dextrorphan" title="Dextrorphan">Dextrorphan</a></li> <li><a href="/w/index.php?title=Diadonium&action=edit&redlink=1" class="new" title="Diadonium (page does not exist)">Diadonium</a></li> <li><a href="/w/index.php?title=Dihydro-beta-erythroidine&action=edit&redlink=1" class="new" title="Dihydro-beta-erythroidine (page does not exist)">DHβE</a></li> <li><a href="/wiki/Dihydrochandonium" title="Dihydrochandonium">Dihydrochandonium</a></li> <li><a href="/wiki/Dimethyltubocurarine" class="mw-redirect" title="Dimethyltubocurarine">Dimethyltubocurarine (metocurine)</a></li> <li><a href="/wiki/Dioscorine" title="Dioscorine">Dioscorine</a></li> <li><a href="/wiki/Dipyrandium" title="Dipyrandium">Dipyrandium</a></li> <li><a href="/wiki/Dizocilpine" title="Dizocilpine">Dizocilpine (MK-801)</a></li> <li><a href="/wiki/Doxacurium" class="mw-redirect" title="Doxacurium">Doxacurium</a></li> <li><a href="/wiki/Encenicline" title="Encenicline">Encenicline</a></li> <li><a href="/wiki/Enflurane" title="Enflurane">Enflurane</a></li> <li><a href="/wiki/Erythravine" title="Erythravine">Erythravine</a></li> <li><a href="/wiki/Esketamine" title="Esketamine">Esketamine</a></li> <li><a href="/wiki/Fazadinium" class="mw-redirect" title="Fazadinium">Fazadinium</a></li> <li><a href="/wiki/Gallamine" class="mw-redirect" title="Gallamine">Gallamine</a></li> <li><a href="/wiki/Gantacurium_chloride" title="Gantacurium chloride">Gantacurium chloride</a></li> <li><a href="/wiki/Halothane" title="Halothane">Halothane</a></li> <li><a href="/wiki/Hexafluronium" class="mw-redirect" title="Hexafluronium">Hexafluronium</a></li> <li><a href="/wiki/Hexamethonium" title="Hexamethonium">Hexamethonium (benzohexonium)</a></li> <li><a href="/wiki/Hydroxybupropion" title="Hydroxybupropion">Hydroxybupropion</a></li> <li><a href="/wiki/Hydroxynorketamine" title="Hydroxynorketamine">Hydroxynorketamine</a></li> <li><a href="/wiki/Ibogaine" title="Ibogaine">Ibogaine</a></li> <li><a href="/wiki/Isoflurane" title="Isoflurane">Isoflurane</a></li> <li><a href="/wiki/Ketamine" title="Ketamine">Ketamine</a></li> <li><a href="/wiki/Kynurenic_acid" title="Kynurenic acid">Kynurenic acid</a></li> <li><a href="/wiki/Laudanosine" title="Laudanosine">Laudanosine</a></li> <li><a href="/wiki/Laudexium" class="mw-redirect" title="Laudexium">Laudexium (laudolissin)</a></li> <li><a href="/wiki/Levacetylmethadol" title="Levacetylmethadol">Levacetylmethadol</a></li> <li><a href="/wiki/Levomethadone" title="Levomethadone">Levomethadone</a></li> <li><a href="/wiki/Malouetine" title="Malouetine">Malouetine</a></li> <li><a href="/wiki/2-Methoxyethyl-18-methoxycoronaridinate" title="2-Methoxyethyl-18-methoxycoronaridinate">ME-18-MC</a></li> <li><a href="/wiki/Mecamylamine" title="Mecamylamine">Mecamylamine</a></li> <li><a href="/wiki/Memantine" title="Memantine">Memantine</a></li> <li><a href="/wiki/Methadone" title="Methadone">Methadone</a></li> <li><a href="/wiki/Methorphan" title="Methorphan">Methorphan (racemethorphan)</a></li> <li><a href="/wiki/Methyllycaconitine" title="Methyllycaconitine">Methyllycaconitine</a></li> <li><a href="/wiki/Metocurine" title="Metocurine">Metocurine</a></li> <li><a href="/wiki/Mivacurium" class="mw-redirect" title="Mivacurium">Mivacurium</a></li> <li><a href="/wiki/Morphanol" class="mw-redirect" title="Morphanol">Morphanol (racemorphan)</a></li> <li><a href="/wiki/Neramexane" title="Neramexane">Neramexane</a></li> <li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide</a></li> <li><a href="/wiki/Norketamine" title="Norketamine">Norketamine</a></li> <li><a href="/wiki/Pancuronium_bromide" title="Pancuronium bromide">Pancuronium bromide</a></li> <li><a href="/wiki/Pempidine" title="Pempidine">Pempidine</a></li> <li><a href="/wiki/Pentamine" title="Pentamine">Pentamine</a></li> <li><a href="/wiki/Pentolinium" title="Pentolinium">Pentolinium</a></li> <li><a href="/wiki/Phencyclidine" title="Phencyclidine">Phencyclidine</a></li> <li><a href="/wiki/Pipecuronium_bromide" title="Pipecuronium bromide">Pipecuronium bromide</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li> <li><a href="/wiki/Promegestone" title="Promegestone">Promegestone</a></li> <li><a href="/wiki/Radafaxine" title="Radafaxine">Radafaxine</a></li> <li><a href="/wiki/Rapacuronium_bromide" title="Rapacuronium bromide">Rapacuronium bromide</a></li> <li><a href="/wiki/Reboxetine" title="Reboxetine">Reboxetine</a></li> <li><a href="/wiki/Rocuronium_bromide" title="Rocuronium bromide">Rocuronium bromide</a></li> <li><a href="/wiki/Sevoflurane" title="Sevoflurane">Sevoflurane</a></li> <li><a href="/wiki/Stercuronium_iodide" title="Stercuronium iodide">Stercuronium iodide</a></li> <li><a href="/wiki/Surugatoxin" title="Surugatoxin">Surugatoxin</a></li> <li><a href="/wiki/Thiocolchicoside" title="Thiocolchicoside">Thiocolchicoside</a></li> <li><a href="/wiki/Threohydrobupropion" title="Threohydrobupropion">Threohydrobupropion</a></li> <li><a href="/wiki/Toxiferine" title="Toxiferine">Toxiferine</a></li> <li><a href="/wiki/Tramadol" title="Tramadol">Tramadol</a></li> <li><a href="/wiki/Trimetaphan_camsilate" title="Trimetaphan camsilate">Trimetaphan camsilate (trimethaphan camsylate)</a></li> <li><a href="/w/index.php?title=Tropeinium&action=edit&redlink=1" class="new" title="Tropeinium (page does not exist)">Tropeinium</a></li> <li><a href="/wiki/Tubocurarine" class="mw-redirect" title="Tubocurarine">Tubocurarine</a></li> <li><a href="/wiki/Vanoxerine" title="Vanoxerine">Vanoxerine</a></li> <li><a href="/wiki/Vecuronium_bromide" title="Vecuronium bromide">Vecuronium bromide</a></li> <li><a href="/wiki/Xenon" title="Xenon">Xenon</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Precursor_(chemistry)" title="Precursor (chemistry)">Precursors</a><br /><small>(and <a href="/wiki/Prodrug" title="Prodrug">prodrugs</a>)</small></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetyl-coA" class="mw-redirect" title="Acetyl-coA">Acetyl-coA</a></li> <li><a href="/wiki/Adafenoxate" title="Adafenoxate">Adafenoxate</a></li> <li><a href="/wiki/Choline" title="Choline">Choline</a> (<a href="/wiki/Lecithin" title="Lecithin">lecithin</a>)</li> <li><a href="/wiki/Citicoline" title="Citicoline">Citicoline</a></li> <li><a href="/wiki/Cyprodenate" title="Cyprodenate">Cyprodenate</a></li> <li><a href="/wiki/Dimethylethanolamine" title="Dimethylethanolamine">Dimethylethanolamine</a></li> <li><a href="/wiki/Glycerophosphocholine" class="mw-redirect" title="Glycerophosphocholine">Glycerophosphocholine</a></li> <li><a href="/wiki/Meclofenoxate" title="Meclofenoxate">Meclofenoxate (centrophenoxine)</a></li> <li><a href="/wiki/Phosphatidylcholine" title="Phosphatidylcholine">Phosphatidylcholine</a></li> <li><a href="/wiki/Phosphatidylethanolamine" title="Phosphatidylethanolamine">Phosphatidylethanolamine</a></li> <li><a href="/wiki/Phosphorylcholine" title="Phosphorylcholine">Phosphorylcholine</a></li> <li><a href="/wiki/Pirisudanol" title="Pirisudanol">Pirisudanol</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></dd> <dd><a href="/wiki/Template:Muscarinic_acetylcholine_receptor_modulators" title="Template:Muscarinic acetylcholine receptor modulators">Muscarinic acetylcholine receptor modulators</a></dd> <dd><a href="/wiki/Template:Acetylcholine_metabolism_and_transport_modulators" title="Template:Acetylcholine metabolism and transport modulators">Acetylcholine metabolism/transport modulators</a></dd></dl> </div></td></tr></tbody></table></div> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox authority-control" aria-label="Navbox" style="padding:3px"><table class="nowraplinks hlist navbox-inner" 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