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vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Stability"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Stability</span> </div> </a> <ul id="toc-Stability-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Enzymes_that_use_NADP(H)_as_a_coenzyme" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Enzymes_that_use_NADP(H)_as_a_coenzyme"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Enzymes that use NADP(H) as a coenzyme</span> </div> </a> <ul id="toc-Enzymes_that_use_NADP(H)_as_a_coenzyme-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Enzymes_that_use_NADP(H)_as_a_substrate" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Enzymes_that_use_NADP(H)_as_a_substrate"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Enzymes that use NADP(H) as a substrate</span> </div> </a> <ul id="toc-Enzymes_that_use_NADP(H)_as_a_substrate-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> </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">Nicotinamide adenine dinucleotide phosphate: Difference between revisions</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 41 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-41" 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">41 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Nikotienamied-adenien-dinukleotiedfosfaat" title="Nikotienamied-adenien-dinukleotiedfosfaat – Afrikaans" lang="af" hreflang="af" data-title="Nikotienamied-adenien-dinukleotiedfosfaat" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target"><span>Afrikaans</span></a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%81%D9%88%D8%B3%D9%81%D8%A7%D8%AA_%D8%AB%D9%86%D8%A7%D8%A6%D9%8A_%D9%86%D9%8A%D9%88%D9%83%D9%84%D9%8A%D9%88%D8%AA%D9%8A%D8%AF_%D8%A7%D9%84%D8%A3%D8%AF%D9%8A%D9%86%D9%8A%D9%86_%D9%88%D8%A3%D9%85%D9%8A%D8%AF_%D8%A7%D9%84%D9%86%D9%8A%D9%83%D9%88%D8%AA%D9%8A%D9%86" title="فوسفات ثنائي نيوكليوتيد الأدينين وأميد النيكوتين – Arabic" lang="ar" hreflang="ar" data-title="فوسفات ثنائي نيوكليوتيد الأدينين وأميد النيكوتين" 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/%D9%86%DB%8C%DA%A9%D9%88%D8%AA%DB%8C%D9%86%E2%80%8C%D8%A2%D9%85%DB%8C%D8%AF_%D8%A2%D8%AF%D9%86%DB%8C%D9%86_%D8%AF%DB%8C%E2%80%8C%D9%86%D9%88%DA%A9%D9%84%D8%A6%D9%88%D8%AA%DB%8C%D8%AF_%D9%81%D9%88%D8%B3%D9%81%D8%A7%D8%AA" title="نیکوتین‌آمید آدنین دی‌نوکلئوتید فوسفات – South Azerbaijani" lang="azb" hreflang="azb" data-title="نیکوتین‌آمید آدنین دی‌نوکلئوتید فوسفات" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%A8%E0%A6%BF%E0%A6%95%E0%A7%8B%E0%A6%9F%E0%A6%BF%E0%A6%A8%E0%A6%BE%E0%A6%AE%E0%A6%BE%E0%A6%87%E0%A6%A1_%E0%A6%85%E0%A7%8D%E0%A6%AF%E0%A6%BE%E0%A6%A1%E0%A7%87%E0%A6%A8%E0%A6%BF%E0%A6%A8_%E0%A6%A1%E0%A6%BE%E0%A6%87%E0%A6%A8%E0%A6%BF%E0%A6%89%E0%A6%95%E0%A7%8D%E0%A6%B2%E0%A6%BF%E0%A6%AF%E0%A6%BC%E0%A6%9F%E0%A6%BE%E0%A6%87%E0%A6%A1_%E0%A6%AB%E0%A6%B8%E0%A6%AB%E0%A7%87%E0%A6%9F" title="নিকোটিনামাইড অ্যাডেনিন ডাইনিউক্লিয়টাইড ফসফেট – Bangla" lang="bn" hreflang="bn" data-title="নিকোটিনামাইড অ্যাডেনিন ডাইনিউক্লিয়টাইড ফসফেট" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%9D%D0%90%D0%94%D0%A4" title="НАДФ – Bulgarian" lang="bg" hreflang="bg" data-title="НАДФ" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Nikotinamid_adenin_dinukleotid-fosfat" title="Nikotinamid adenin dinukleotid-fosfat – Bosnian" lang="bs" hreflang="bs" data-title="Nikotinamid adenin dinukleotid-fosfat" 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/Fosfat_de_dinucle%C3%B2tid_de_nicotinamida_i_adenina" title="Fosfat de dinucleòtid de nicotinamida i adenina – Catalan" lang="ca" hreflang="ca" data-title="Fosfat de dinucleòtid de nicotinamida i adenina" 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/Nikotinamidadenindinukleotidfosf%C3%A1t" title="Nikotinamidadenindinukleotidfosfát – Czech" lang="cs" hreflang="cs" data-title="Nikotinamidadenindinukleotidfosfát" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Nikotinamid-adenin-dinukleotidfosfat" title="Nikotinamid-adenin-dinukleotidfosfat – Danish" lang="da" hreflang="da" data-title="Nikotinamid-adenin-dinukleotidfosfat" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Nicotinamidadenindinukleotidphosphat" title="Nicotinamidadenindinukleotidphosphat – German" lang="de" hreflang="de" data-title="Nicotinamidadenindinukleotidphosphat" 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/NADP" title="NADP – Estonian" lang="et" hreflang="et" data-title="NADP" 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/Nicotinamida_adenina_dinucle%C3%B3tido_fosfato" title="Nicotinamida adenina dinucleótido fosfato – Spanish" lang="es" hreflang="es" data-title="Nicotinamida adenina dinucleótido fosfato" 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/NADPH" title="NADPH – Esperanto" lang="eo" hreflang="eo" data-title="NADPH" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%86%DB%8C%DA%A9%D9%88%D8%AA%DB%8C%D9%86%E2%80%8C%D8%A2%D9%85%DB%8C%D8%AF_%D8%A2%D8%AF%D9%86%DB%8C%D9%86_%D8%AF%DB%8C%E2%80%8C%D9%86%D9%88%DA%A9%D9%84%D8%A6%D9%88%D8%AA%DB%8C%D8%AF_%D9%81%D8%B3%D9%81%D8%A7%D8%AA" title="نیکوتین‌آمید آدنین دی‌نوکلئوتید فسفات – Persian" lang="fa" hreflang="fa" data-title="نیکوتین‌آمید آدنین دی‌نوکلئوتید فسفات" 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/Nicotinamide_ad%C3%A9nine_dinucl%C3%A9otide_phosphate" title="Nicotinamide adénine dinucléotide phosphate – French" lang="fr" hreflang="fr" data-title="Nicotinamide adénine dinucléotide phosphate" 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/Fosfato_do_dinucle%C3%B3tido_de_nicotinamida_e_adenina" title="Fosfato do dinucleótido de nicotinamida e adenina – Galician" lang="gl" hreflang="gl" data-title="Fosfato do dinucleótido de nicotinamida e adenina" 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/%EB%8B%88%EC%BD%94%ED%8B%B4%EC%95%84%EB%A7%88%EC%9D%B4%EB%93%9C_%EC%95%84%EB%8D%B0%EB%8B%8C_%EB%8B%A4%EC%9D%B4%EB%89%B4%ED%81%B4%EB%A0%88%EC%98%A4%ED%83%80%EC%9D%B4%EB%93%9C_%EC%9D%B8%EC%82%B0" title="니코틴아마이드 아데닌 다이뉴클레오타이드 인산 – Korean" lang="ko" hreflang="ko" data-title="니코틴아마이드 아데닌 다이뉴클레오타이드 인산" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/NADH" title="NADH – Indonesian" lang="id" hreflang="id" data-title="NADH" 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/Nicotinammide_adenina_dinucleotide_fosfato" title="Nicotinammide adenina dinucleotide fosfato – Italian" lang="it" hreflang="it" data-title="Nicotinammide adenina dinucleotide fosfato" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/NADP" title="NADP – Lithuanian" lang="lt" hreflang="lt" data-title="NADP" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Nikotinamida_adenina_dinukleotida_fosfat" title="Nikotinamida adenina dinukleotida fosfat – Malay" lang="ms" hreflang="ms" data-title="Nikotinamida adenina dinukleotida fosfat" 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/Nicotinamide-adenine-dinucleotidefosfaat" title="Nicotinamide-adenine-dinucleotidefosfaat – Dutch" lang="nl" hreflang="nl" data-title="Nicotinamide-adenine-dinucleotidefosfaat" 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%83%8B%E3%82%B3%E3%83%81%E3%83%B3%E3%82%A2%E3%83%9F%E3%83%89%E3%82%A2%E3%83%87%E3%83%8B%E3%83%B3%E3%82%B8%E3%83%8C%E3%82%AF%E3%83%AC%E3%82%AA%E3%83%81%E3%83%89%E3%83%AA%E3%83%B3%E9%85%B8" title="ニコチンアミドアデニンジヌクレオチドリン酸 – Japanese" lang="ja" hreflang="ja" data-title="ニコチンアミドアデニンジヌクレオチドリン酸" 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-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Nicotinamida_adenina_dinucleotid_fosfat" title="Nicotinamida adenina dinucleotid fosfat – Occitan" lang="oc" hreflang="oc" data-title="Nicotinamida adenina dinucleotid fosfat" data-language-autonym="Occitan" data-language-local-name="Occitan" class="interlanguage-link-target"><span>Occitan</span></a></li><li class="interlanguage-link interwiki-pa mw-list-item"><a href="https://pa.wikipedia.org/wiki/%E0%A8%A8%E0%A8%BF%E0%A8%95%E0%A9%8B%E0%A8%9F%E0%A8%BF%E0%A8%A8%E0%A8%BE%E0%A8%AE%E0%A8%BE%E0%A8%88%E0%A8%A1_%E0%A8%90%E0%A8%A1%E0%A9%80%E0%A8%A8%E0%A8%BE%E0%A8%88%E0%A8%A8_%E0%A8%A1%E0%A8%BE%E0%A8%88%E0%A8%A8%E0%A9%82%E0%A8%95%E0%A8%B2%E0%A9%80%E0%A8%93%E0%A8%9F%E0%A8%BE%E0%A8%88%E0%A8%A1_%E0%A8%AB%E0%A8%BE%E0%A8%B8%E0%A8%AB%E0%A9%87%E0%A8%9F" title="ਨਿਕੋਟਿਨਾਮਾਈਡ ਐਡੀਨਾਈਨ ਡਾਈਨੂਕਲੀਓਟਾਈਡ ਫਾਸਫੇਟ – Punjabi" lang="pa" hreflang="pa" data-title="ਨਿਕੋਟਿਨਾਮਾਈਡ ਐਡੀਨਾਈਨ ਡਾਈਨੂਕਲੀਓਟਾਈਡ ਫਾਸਫੇਟ" data-language-autonym="ਪੰਜਾਬੀ" data-language-local-name="Punjabi" class="interlanguage-link-target"><span>ਪੰਜਾਬੀ</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Fosfato_de_dinucle%C3%B3tido_de_nicotinamida_e_adenina" title="Fosfato de dinucleótido de nicotinamida e adenina – Portuguese" lang="pt" hreflang="pt" data-title="Fosfato de dinucleótido de nicotinamida e adenina" 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/Nicotinamid_adenin_dinucleotid_fosfat" title="Nicotinamid adenin dinucleotid fosfat – Romanian" lang="ro" hreflang="ro" data-title="Nicotinamid adenin dinucleotid fosfat" 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%9D%D0%B8%D0%BA%D0%BE%D1%82%D0%B8%D0%BD%D0%B0%D0%BC%D0%B8%D0%B4%D0%B0%D0%B4%D0%B5%D0%BD%D0%B8%D0%BD%D0%B4%D0%B8%D0%BD%D1%83%D0%BA%D0%BB%D0%B5%D0%BE%D1%82%D0%B8%D0%B4%D1%84%D0%BE%D1%81%D1%84%D0%B0%D1%82" title="Никотинамидадениндинуклеотидфосфат – Russian" lang="ru" hreflang="ru" data-title="Никотинамидадениндинуклеотидфосфат" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Nicotinamide_adenine_dinucleotide_phosphate" title="Nicotinamide adenine dinucleotide phosphate – Simple English" lang="en-simple" hreflang="en-simple" data-title="Nicotinamide adenine dinucleotide phosphate" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link 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title="Nicotinamide adenine dinucleotide phosphate">Revision as of 18:49, 2 October 2024</a> <span class="mw-diff-edit"><a href="/w/index.php?title=Nicotinamide_adenine_dinucleotide_phosphate&action=edit&oldid=1249017234" title="Nicotinamide adenine dinucleotide phosphate">edit</a></span><span class="mw-diff-timestamp" data-timestamp="2024-10-02T18:49:18Z"></span></strong></div><div id="mw-diff-otitle2"><a href="/wiki/Special:Contributions/12.232.142.116" class="mw-userlink mw-anonuserlink" title="Special:Contributions/12.232.142.116" data-mw-revid="1249017234"><bdi>12.232.142.116</bdi></a> <span class="mw-usertoollinks">(<a href="/wiki/User_talk:12.232.142.116" class="mw-usertoollinks-talk" title="User talk:12.232.142.116">talk</a>)</span><div class="mw-diff-usermetadata"></div></div><div id="mw-diff-otitle3"> <span class="comment comment--without-parentheses">I changed one sentence that was incorrect</span></div><div id="mw-diff-otitle5"><span class="mw-tag-markers"><a href="/wiki/Special:Tags" title="Special:Tags">Tag</a>: <span class="mw-tag-marker mw-tag-marker-visualeditor"><a href="/wiki/Wikipedia:VisualEditor" title="Wikipedia:VisualEditor">Visual edit</a></span></span></div><div id="mw-diff-otitle4"><a href="/w/index.php?title=Nicotinamide_adenine_dinucleotide_phosphate&diff=prev&oldid=1249017234" title="Nicotinamide adenine dinucleotide phosphate" id="differences-prevlink">← Previous edit</a></div></td> <td colspan="2" class="diff-ntitle diff-side-added"><div id="mw-diff-ntitle1"><strong><a href="/w/index.php?title=Nicotinamide_adenine_dinucleotide_phosphate&oldid=1258185070" title="Nicotinamide adenine dinucleotide phosphate">Latest revision as of 16:11, 18 November 2024</a> <span class="mw-diff-edit"><a href="/w/index.php?title=Nicotinamide_adenine_dinucleotide_phosphate&action=edit" title="Nicotinamide adenine dinucleotide phosphate">edit</a></span><span class="mw-diff-timestamp" data-timestamp="2024-11-18T16:11:27Z"></span> <span class="mw-diff-undo"><a href="/w/index.php?title=Nicotinamide_adenine_dinucleotide_phosphate&action=edit&undoafter=1249017234&undo=1258185070" title=""Undo" reverts this edit and opens the edit form in preview mode. It allows adding a reason in the summary.">undo</a></span></strong></div><div id="mw-diff-ntitle2"><a href="/wiki/Special:Contributions/185.3.146.16" class="mw-userlink mw-anonuserlink" title="Special:Contributions/185.3.146.16" data-mw-revid="1258185070"><bdi>185.3.146.16</bdi></a> <span class="mw-usertoollinks">(<a href="/w/index.php?title=User_talk:185.3.146.16&action=edit&redlink=1" class="new mw-usertoollinks-talk" title="User talk:185.3.146.16 (page does not exist)">talk</a>)</span><div class="mw-diff-usermetadata"></div></div><div id="mw-diff-ntitle3"> <span class="comment comment--without-parentheses"><span class="autocomment"><a href="#Enzymes_that_use_NADP(H)_as_a_coenzyme">→<bdi dir="ltr">Enzymes that use NADP(H) as a coenzyme</bdi></a>: </span> Added Rossmann fold and a reference</span></div><div id="mw-diff-ntitle5"></div><div id="mw-diff-ntitle4"> </div></td> </tr><tr> <td colspan="2" class="diff-lineno">Line 75:</td> <td colspan="2" class="diff-lineno">Line 75:</td> </tr> <tr> <td class="diff-marker"></td> <td class="diff-context diff-side-deleted"><br /></td> <td class="diff-marker"></td> <td class="diff-context diff-side-added"><br /></td> </tr> <tr> <td class="diff-marker"></td> <td class="diff-context diff-side-deleted"><div>== Enzymes that use NADP(H) as a coenzyme ==</div></td> <td class="diff-marker"></td> <td class="diff-context diff-side-added"><div>== Enzymes that use NADP(H) as a coenzyme ==</div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>Many enzymes that bind NADP share a common super-secondary structure named named the "Rossmann fold". The initial beta-alpha-beta (βαβ) fold is the most conserved segment of the Rossmann folds. This segment is in contact with the ADP portion of NADP. Therefore, it is also called an "ADP-binding βαβ fold".<ref name="2015-Hanukoglu">{{cite journal |vauthors=Hanukoglu I |title=Proteopedia: Rossmann fold: A beta-alpha-beta fold at dinucleotide binding sites |journal=Biochem Mol Biol Educ |volume=43 |issue=3 |pages=206–9 |date=2015 |pmid=25704928 |doi=10.1002/bmb.20849 |url=}}</ref></div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><br /></td> </tr> <tr> <td class="diff-marker"></td> <td class="diff-context diff-side-deleted"><div>* [[Adrenodoxin reductase]]: This enzyme is present ubiquitously in most organisms.<ref name="2017-Hanukoglu-JME">{{cite journal | vauthors = Hanukoglu I | title = Conservation of the Enzyme-Coenzyme Interfaces in FAD and NADP Binding Adrenodoxin Reductase-A Ubiquitous Enzyme | journal = Journal of Molecular Evolution | volume = 85 | issue = 5–6 | pages = 205–218 | date = December 2017 | pmid = 29177972 | doi = 10.1007/s00239-017-9821-9 | s2cid = 7120148 | bibcode = 2017JMolE..85..205H }}</ref> It transfers two electrons from NADPH to FAD. In vertebrates, it serves as the first enzyme in the chain of mitochondrial P450 systems that synthesize steroid hormones.<ref name="1992-Hanukoglu">{{cite journal | vauthors = Hanukoglu I | title = Steroidogenic enzymes: structure, function, and role in regulation of steroid hormone biosynthesis | journal = The Journal of Steroid Biochemistry and Molecular Biology | volume = 43 | issue = 8 | pages = 779–804 | date = December 1992 | pmid = 22217824 | doi = 10.1016/0960-0760(92)90307-5 | s2cid = 112729 }}</ref></div></td> <td class="diff-marker"></td> <td class="diff-context diff-side-added"><div>* [[Adrenodoxin reductase]]: This enzyme is present ubiquitously in most organisms.<ref name="2017-Hanukoglu-JME">{{cite journal | vauthors = Hanukoglu I | title = Conservation of the Enzyme-Coenzyme Interfaces in FAD and NADP Binding Adrenodoxin Reductase-A Ubiquitous Enzyme | journal = Journal of Molecular Evolution | volume = 85 | issue = 5–6 | pages = 205–218 | date = December 2017 | pmid = 29177972 | doi = 10.1007/s00239-017-9821-9 | s2cid = 7120148 | bibcode = 2017JMolE..85..205H }}</ref> It transfers two electrons from NADPH to FAD. In vertebrates, it serves as the first enzyme in the chain of mitochondrial P450 systems that synthesize steroid hormones.<ref name="1992-Hanukoglu">{{cite journal | vauthors = Hanukoglu I | title = Steroidogenic enzymes: structure, function, and role in regulation of steroid hormone biosynthesis | journal = The Journal of Steroid Biochemistry and Molecular Biology | volume = 43 | issue = 8 | pages = 779–804 | date = December 1992 | pmid = 22217824 | doi = 10.1016/0960-0760(92)90307-5 | s2cid = 112729 }}</ref></div></td> </tr> <tr> <td class="diff-marker"></td> <td class="diff-context diff-side-deleted"><br /></td> <td class="diff-marker"></td> <td class="diff-context diff-side-added"><br /></td> </tr> </table><hr class='diff-hr' id='mw-oldid' /> <h2 class='diff-currentversion-title'>Latest revision as of 16:11, 18 November 2024</h2> <div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/Nicotinamide_adenine_dinucleotide" title="Nicotinamide adenine dinucleotide">Nicotinamide adenine dinucleotide</a> (NAD<sup>+</sup>/NADH).</div> <p> <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> </p> <table class="infobox ib-chembox"> <caption>Nicotinamide adenine dinucleotide phosphate </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:NADP%2B_phys.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/65/NADP%2B_phys.svg/220px-NADP%2B_phys.svg.png" decoding="async" width="220" height="368" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/65/NADP%2B_phys.svg/330px-NADP%2B_phys.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/65/NADP%2B_phys.svg/440px-NADP%2B_phys.svg.png 2x" data-file-width="363" data-file-height="608" /></a></span> </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=53-59-8">53-59-8</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;">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%28N%29c1ccc%5Bn%2B%5D%28c1%29%5BC%40H%5D2%5BC%40H%5D%28O%29%5BC%40H%5D%28O%29%5BC%40H%5D%28O2%29COP%28%5BO-%5D%29%28%3DO%29OP%28%3DO%29%28O%29OC%5BC%40H%5D3O%5BC%40%40H%5D%28n4cnc5c4ncnc5N%29%5BC%40%40H%5D%28%5BC%40%40H%5D3O%29OP%28%3DO%29%28O%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=44409">CHEBI:44409</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/ChEMBL" title="ChEMBL">ChEMBL</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/chembl/explore/compound/ChEMBL2364573">ChEMBL2364573</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/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.5674.html">5674</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/100.000.163">100.000.163</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q28747#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><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=NADP">NADP</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/5885">5885</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/BY8P107XEP">BY8P107XEP</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 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/C21H28N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1-4,7-8,10-11,13-16,20-21,29-31H,5-6H2,(H7-,22,23,24,25,32,33,34,35,36,37,38,39)/t10-,11-,13-,14-,15-,16-,20-,21-/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: XJLXINKUBYWONI-NNYOXOHSSA-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/C21H28N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1-4,7-8,10-11,13-16,20-21,29-31H,5-6H2,(H7-,22,23,24,25,32,33,34,35,36,37,38,39)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: XJLXINKUBYWONI-NNYOXOHSBN</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(N)c1ccc[n+](c1)[C@H]2[C@H](O)[C@H](O)[C@H](O2)COP([O-])(=O)OP(=O)(O)OC[C@H]3O[C@@H](n4cnc5c4ncnc5N)[C@@H]([C@@H]3O)OP(=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>21</sub><span title="Hydrogen">H</span><sub>29</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> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002744416000000000♠"></span>744.416</span> g·mol<sup>−1</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=456480844&page2=Nicotinamide+adenine+dinucleotide+phosphate">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>Nicotinamide adenine dinucleotide phosphate</b>, abbreviated <b>NADP</b><sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><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> or, in older notation, <b>TPN</b> (triphosphopyridine nucleotide), is a <a href="/wiki/Cofactor_(biochemistry)" title="Cofactor (biochemistry)">cofactor</a> used in <a href="/wiki/Anabolic_reaction" class="mw-redirect" title="Anabolic reaction">anabolic reactions</a>, such as the <a href="/wiki/Calvin_cycle" title="Calvin cycle">Calvin cycle</a> and <a href="/wiki/Lipid" title="Lipid">lipid</a> and <a href="/wiki/Nucleic_acid" title="Nucleic acid">nucleic acid</a> syntheses, which require <b>NADPH</b> as a <a href="/wiki/Reducing_agent" title="Reducing agent">reducing agent</a> ('hydrogen source'). NADPH is the <a href="/wiki/Redox" title="Redox">reduced</a> form, whereas NADP<sup>+</sup> is the <a href="/wiki/Redox" title="Redox">oxidized</a> form. NADP<sup>+</sup> is used by all forms of cellular life. NADP<sup>+</sup> is essential for life because it is needed for cellular respiration.<sup id="cite_ref-pmid26284036_3-0" class="reference"><a href="#cite_note-pmid26284036-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>NADP<sup>+</sup> differs from <a href="/wiki/NAD%2B" class="mw-redirect" title="NAD+">NAD<sup>+</sup></a> by the presence of an additional <a href="/wiki/Phosphate_group" class="mw-redirect" title="Phosphate group">phosphate group</a> on the 2' position of the <a href="/wiki/Ribose" title="Ribose">ribose</a> ring that carries the <a href="/wiki/Adenine" title="Adenine">adenine</a> <a href="/wiki/Moiety_(chemistry)" title="Moiety (chemistry)">moiety</a>. This extra phosphate is added by <a href="/wiki/NAD%2B_kinase" title="NAD+ kinase">NAD<sup>+</sup> kinase</a> and removed by NADP<sup>+</sup> phosphatase.<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="Biosynthesis">Biosynthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Nicotinamide_adenine_dinucleotide_phosphate&action=edit&section=1" title="Edit section: Biosynthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="NADP+"><span id="NADP.2B"></span>NADP<sup>+</sup></h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Nicotinamide_adenine_dinucleotide_phosphate&action=edit&section=2" title="Edit section: NADP+"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In general, NADP<sup>+</sup> is synthesized before NADPH is. Such a reaction usually starts with <a href="/wiki/NAD%2B" class="mw-redirect" title="NAD+">NAD<sup>+</sup></a> from either the de-novo or the salvage pathway, with <a href="/wiki/NAD%2B_kinase" title="NAD+ kinase">NAD<sup>+</sup> kinase</a> adding the extra phosphate group. <a href="/wiki/ADP-ribosyl_cyclase" title="ADP-ribosyl cyclase">ADP-ribosyl cyclase</a> allows for synthesis from <a href="/wiki/Nicotinamide" title="Nicotinamide">nicotinamide</a> in the salvage pathway, and NADP<sup>+</sup> phosphatase can convert NADPH back to NADH to maintain a balance.<sup id="cite_ref-pmid26284036_3-1" class="reference"><a href="#cite_note-pmid26284036-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Some forms of the NAD<sup>+</sup> kinase, notably the one in mitochondria, can also accept NADH to turn it directly into NADPH.<sup id="cite_ref-5" class="reference"><a href="#cite_note-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> The prokaryotic pathway is less well understood, but with all the similar proteins the process should work in a similar way.<sup id="cite_ref-pmid26284036_3-2" class="reference"><a href="#cite_note-pmid26284036-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="NADPH">NADPH</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Nicotinamide_adenine_dinucleotide_phosphate&action=edit&section=3" title="Edit section: NADPH"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>NADPH is produced from NADP<sup>+</sup>. The major source of NADPH in animals and other non-photosynthetic organisms is the <a href="/wiki/Pentose_phosphate_pathway" title="Pentose phosphate pathway">pentose phosphate pathway</a>, by <a href="/wiki/Glucose-6-phosphate_dehydrogenase" title="Glucose-6-phosphate dehydrogenase">glucose-6-phosphate dehydrogenase</a> (G6PDH) in the first step. The pentose phosphate pathway also produces pentose, another important part of NAD(P)H, from glucose. Some bacteria also use G6PDH for the <a href="/wiki/Entner%E2%80%93Doudoroff_pathway" title="Entner–Doudoroff pathway">Entner–Doudoroff pathway</a>, but NADPH production remains the same.<sup id="cite_ref-pmid26284036_3-3" class="reference"><a href="#cite_note-pmid26284036-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Ferredoxin%E2%80%94NADP(%2B)_reductase" title="Ferredoxin—NADP(+) reductase">Ferredoxin–NADP<sup>+</sup> reductase</a>, present in all domains of life, is a major source of NADPH in photosynthetic organisms including plants and cyanobacteria. It appears in the last step of the electron chain of the <a href="/wiki/Light-dependent_reactions" title="Light-dependent reactions">light reactions</a> of <a href="/wiki/Photosynthesis" title="Photosynthesis">photosynthesis</a>. It is used as reducing power for the biosynthetic reactions in the <a href="/wiki/Calvin_cycle" title="Calvin cycle">Calvin cycle</a> to assimilate carbon dioxide and help turn the carbon dioxide into glucose. It has functions in accepting electrons in other non-photosynthetic pathways as well: it is needed in the reduction of nitrate into ammonia for plant assimilation in <a href="/wiki/Nitrogen_cycle" title="Nitrogen cycle">nitrogen cycle</a> and in the production of oils.<sup id="cite_ref-pmid26284036_3-4" class="reference"><a href="#cite_note-pmid26284036-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>There are several other lesser-known mechanisms of generating NADPH, all of which depend on the presence of <a href="/wiki/Mitochondria" class="mw-redirect" title="Mitochondria">mitochondria</a> in eukaryotes. The key enzymes in these carbon-metabolism-related processes are NADP-linked isoforms of <a href="/wiki/Malic_enzyme" title="Malic enzyme">malic enzyme</a>, <a href="/wiki/Isocitrate_dehydrogenase" title="Isocitrate dehydrogenase">isocitrate dehydrogenase</a> (IDH), and <a href="/wiki/Glutamate_dehydrogenase" title="Glutamate dehydrogenase">glutamate dehydrogenase</a>. In these reactions, NADP<sup>+</sup> acts like NAD<sup>+</sup> in other enzymes as an oxidizing agent.<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> The isocitrate dehydrogenase mechanism appears to be the major source of NADPH in fat and possibly also liver cells.<sup id="cite_ref-Palmer_8-0" class="reference"><a href="#cite_note-Palmer-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> These processes are also found in bacteria. Bacteria can also use a NADP-dependent <a href="/wiki/Glyceraldehyde_3-phosphate_dehydrogenase" title="Glyceraldehyde 3-phosphate dehydrogenase">glyceraldehyde 3-phosphate dehydrogenase</a> for the same purpose. Like the pentose phosphate pathway, these pathways are related to parts of <a href="/wiki/Glycolysis" title="Glycolysis">glycolysis</a>.<sup id="cite_ref-pmid26284036_3-5" class="reference"><a href="#cite_note-pmid26284036-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Another carbon metabolism-related pathway involved in the generation of NADPH is the mitochondrial folate cycle, which uses principally serine as a source of one-carbon units to sustain nucleotide synthesis and redox homeostasis in mitochondria. Mitochondrial folate cycle has been recently suggested as the principal contributor to NADPH generation in mitochondria of cancer cells.<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> </p><p>NADPH can also be generated through pathways unrelated to carbon metabolism. The ferredoxin reductase is such an example. <a href="/wiki/Nicotinamide_nucleotide_transhydrogenase" title="Nicotinamide nucleotide transhydrogenase">Nicotinamide nucleotide transhydrogenase</a> transfers the hydrogen between NAD(P)H and NAD(P)<sup>+</sup>, and is found in eukaryotic mitochondria and many bacteria. There are versions that depend on a <a href="/wiki/Proton_gradient" class="mw-redirect" title="Proton gradient">proton gradient</a> to work and ones that do not. Some anaerobic organisms use <a href="/wiki/Hydrogen_dehydrogenase_(NADP%2B)" title="Hydrogen dehydrogenase (NADP+)">NADP<sup>+</sup>-linked hydrogenase</a>, ripping a hydride from hydrogen gas to produce a proton and NADPH.<sup id="cite_ref-pmid26284036_3-6" class="reference"><a href="#cite_note-pmid26284036-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>Like <a href="/wiki/NADH" class="mw-redirect" title="NADH">NADH</a>, NADPH is <a href="/wiki/Fluorescent" class="mw-redirect" title="Fluorescent">fluorescent</a>. NADPH in aqueous solution excited at the nicotinamide absorbance of ~335 nm (near UV) has a fluorescence emission which peaks at 445-460 nm (violet to blue). NADP<sup>+</sup> has no appreciable fluorescence.<sup id="cite_ref-Blacker_Mann_Gale_Ziegler_p._10-0" class="reference"><a href="#cite_note-Blacker_Mann_Gale_Ziegler_p.-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Function">Function</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Nicotinamide_adenine_dinucleotide_phosphate&action=edit&section=4" title="Edit section: Function"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>NADPH provides the reducing agents, usually hydrogen atoms, for biosynthetic reactions and the <a href="/wiki/Oxidation-reduction" class="mw-redirect" title="Oxidation-reduction">oxidation-reduction</a> involved in protecting against the toxicity of <a href="/wiki/Reactive_oxygen_species" title="Reactive oxygen species">reactive oxygen species</a> (ROS), allowing the regeneration of <a href="/wiki/Glutathione" title="Glutathione">glutathione</a> (GSH).<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> NADPH is also used for <a href="/wiki/Anabolic" class="mw-redirect" title="Anabolic">anabolic</a> pathways, such as <a href="/wiki/Cholesterol_synthesis" class="mw-redirect" title="Cholesterol synthesis">cholesterol synthesis</a>, steroid synthesis,<sup id="cite_ref-:0_12-0" class="reference"><a href="#cite_note-:0-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> ascorbic acid synthesis,<sup id="cite_ref-:0_12-1" class="reference"><a href="#cite_note-:0-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> xylitol synthesis,<sup id="cite_ref-:0_12-2" class="reference"><a href="#cite_note-:0-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> cytosolic fatty acid synthesis<sup id="cite_ref-:0_12-3" class="reference"><a href="#cite_note-:0-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> and microsomal <a href="/wiki/Fatty_acid_synthesis" title="Fatty acid synthesis">fatty acid chain elongation</a>. </p><p>The NADPH system is also responsible for generating free radicals in immune cells by <a href="/wiki/NADPH_oxidase" title="NADPH oxidase">NADPH oxidase</a>. These radicals are used to destroy pathogens in a process termed the <a href="/wiki/Respiratory_burst" title="Respiratory burst">respiratory burst</a>.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> It is the source of reducing equivalents for <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450</a> <a href="/wiki/Hydroxylation" title="Hydroxylation">hydroxylation</a> of <a href="/wiki/Aromatic_compounds" class="mw-redirect" title="Aromatic compounds">aromatic compounds</a>, <a href="/wiki/Steroid" title="Steroid">steroids</a>, <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohols</a>, and <a href="/wiki/Drug" title="Drug">drugs</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Stability">Stability</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Nicotinamide_adenine_dinucleotide_phosphate&action=edit&section=5" title="Edit section: Stability"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>NADH and NADPH are very stable in basic solutions, but NAD<sup>+</sup> and NADP<sup>+</sup> are degraded in basic solutions into a fluorescent product that can be used conveniently for quantitation. Conversely, NADPH and NADH are degraded by acidic solutions while NAD<sup>+</sup>/NADP<sup>+</sup> are fairly stable to acid.<sup id="cite_ref-Passonneau1993_14-0" class="reference"><a href="#cite_note-Passonneau1993-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><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> </p> <div class="mw-heading mw-heading2"><h2 id="Enzymes_that_use_NADP(H)_as_a_coenzyme"><span id="Enzymes_that_use_NADP.28H.29_as_a_coenzyme"></span>Enzymes that use NADP(H) as a coenzyme</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Nicotinamide_adenine_dinucleotide_phosphate&action=edit&section=6" title="Edit section: Enzymes that use NADP(H) as a coenzyme"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Many enzymes that bind NADP share a common super-secondary structure named named the "Rossmann fold". The initial beta-alpha-beta (βαβ) fold is the most conserved segment of the Rossmann folds. This segment is in contact with the ADP portion of NADP. Therefore, it is also called an "ADP-binding βαβ fold".<sup id="cite_ref-2015-Hanukoglu_16-0" class="reference"><a href="#cite_note-2015-Hanukoglu-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <ul><li><a href="/wiki/Adrenodoxin_reductase" title="Adrenodoxin reductase">Adrenodoxin reductase</a>: This enzyme is present ubiquitously in most organisms.<sup id="cite_ref-2017-Hanukoglu-JME_17-0" class="reference"><a href="#cite_note-2017-Hanukoglu-JME-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> It transfers two electrons from NADPH to FAD. In vertebrates, it serves as the first enzyme in the chain of mitochondrial P450 systems that synthesize steroid hormones.<sup id="cite_ref-1992-Hanukoglu_18-0" class="reference"><a href="#cite_note-1992-Hanukoglu-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup></li></ul> <div class="mw-heading mw-heading2"><h2 id="Enzymes_that_use_NADP(H)_as_a_substrate"><span id="Enzymes_that_use_NADP.28H.29_as_a_substrate"></span>Enzymes that use NADP(H) as a substrate</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Nicotinamide_adenine_dinucleotide_phosphate&action=edit&section=7" title="Edit section: Enzymes that use NADP(H) as a substrate"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In 2018 and 2019, the first two reports of enzymes that catalyze the removal of the 2' phosphate of NADP(H) in eukaryotes emerged. First the <a href="/wiki/Cytoplasm" title="Cytoplasm">cytoplasmic</a> protein MESH1 (<span class="plainlinks"><a rel="nofollow" class="external text" href="https://www.uniprot.org/uniprot/Q8N4P3">Q8N4P3</a></span>),<sup id="cite_ref-Ding_2018_19-0" class="reference"><a href="#cite_note-Ding_2018-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> then the <a href="/wiki/Mitochondrial" class="mw-redirect" title="Mitochondrial">mitochondrial</a> protein <a href="/wiki/Nocturnin" title="Nocturnin">nocturnin</a><sup id="cite_ref-Estrella_2019_20-0" class="reference"><a href="#cite_note-Estrella_2019-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> were reported. Of note, the structures and NADPH binding of MESH1 (<a rel="nofollow" class="external text" href="https://www.rcsb.org/structure/5vxA">5VXA</a>) and nocturnin (<a rel="nofollow" class="external text" href="https://www.rcsb.org/structure/6nf0">6NF0</a>) are not related. </p> <style data-mw-deduplicate="TemplateStyles:r1248256098">@media all and (max-width:720px){.mw-parser-output .mod-gallery{width:100%!important}}.mw-parser-output .mod-gallery{display:table}.mw-parser-output .mod-gallery-default{background:transparent;margin-top:4px}.mw-parser-output .mod-gallery-center{margin-left:auto;margin-right:auto}.mw-parser-output .mod-gallery-left{float:left}.mw-parser-output .mod-gallery-right{float:right}.mw-parser-output .mod-gallery-none{float:none}.mw-parser-output .mod-gallery-collapsible{width:100%}.mw-parser-output .mod-gallery .title,.mw-parser-output .mod-gallery .main,.mw-parser-output .mod-gallery .footer{display:table-row}.mw-parser-output .mod-gallery .title>div{display:table-cell;padding:0 4px 4px;text-align:center;font-weight:bold}.mw-parser-output .mod-gallery .main>div{display:table-cell}.mw-parser-output .mod-gallery .gallery{line-height:1.35em}.mw-parser-output .mod-gallery .footer>div{display:table-cell;padding:4px;text-align:right;font-size:85%;line-height:1em}.mw-parser-output .mod-gallery .title>div *,.mw-parser-output .mod-gallery .footer>div *{overflow:visible}.mw-parser-output .mod-gallery .gallerybox img{background:none!important}.mw-parser-output .mod-gallery .bordered-images .thumb img{border:solid var(--background-color-neutral,#eaecf0)1px}.mw-parser-output .mod-gallery .whitebg .thumb{background:var(--background-color-base,#fff)!important}</style><div class="mod-gallery mod-gallery-default mod-gallery-center"><div class="title"><div><a href="/wiki/Ball-and-stick_model" title="Ball-and-stick model">Ball-and-stick models</a> of NADP+ and NADPH</div></div><div class="main"><div><ul class="gallery mw-gallery-traditional nochecker bordered-images whitebg"> <li class="gallerybox" style="width: 285px"> <div class="thumb" style="width: 280px; height: 280px;"><span typeof="mw:File"><a href="/wiki/File:NADP-3D-balls.png" class="mw-file-description" title="NADP+"><img alt="NADP+" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/36/NADP-3D-balls.png/230px-NADP-3D-balls.png" decoding="async" width="230" height="250" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/36/NADP-3D-balls.png/345px-NADP-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/36/NADP-3D-balls.png/460px-NADP-3D-balls.png 2x" data-file-width="1013" data-file-height="1100" /></a></span></div> <div class="gallerytext">NADP+</div> </li> <li class="gallerybox" style="width: 285px"> <div class="thumb" style="width: 280px; height: 280px;"><span typeof="mw:File"><a href="/wiki/File:NADPH-3D-balls.png" class="mw-file-description" title="NADPH"><img alt="NADPH" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1d/NADPH-3D-balls.png/189px-NADPH-3D-balls.png" decoding="async" width="189" height="250" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1d/NADPH-3D-balls.png/283px-NADPH-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1d/NADPH-3D-balls.png/378px-NADPH-3D-balls.png 2x" data-file-width="831" data-file-height="1100" /></a></span></div> <div class="gallerytext">NADPH</div> </li> </ul></div></div></div> <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=Nicotinamide_adenine_dinucleotide_phosphate&action=edit&section=8" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></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 class="citation web cs1"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/NADP-nicotinamide-adenine-dinucleotide-phosphate">"NADP nicotinamide-adenine-dinucleotide phosphate"</a>. <i>PubChem</i>. 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Retrieved <span class="nowrap">2024-08-22</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=PubChem&rft.atitle=NADP+nicotinamide-adenine-dinucleotide+phosphate&rft_id=https%3A%2F%2Fpubchem.ncbi.nlm.nih.gov%2Fcompound%2FNADP-nicotinamide-adenine-dinucleotide-phosphate&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANicotinamide+adenine+dinucleotide+phosphate" 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 id="CITEREFKarlson2014" class="citation book cs1">Karlson P (2014-05-12). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=lGyeBQAAQBAJ&dq=Nicotinamide+adenine+dinucleotide+phosphate+abbreviated+NADP&pg=PA95"><i>Introduction to Modern Biochemistry</i></a>. 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abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Enzyme_cofactors" title="Template:Enzyme cofactors"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Enzyme_cofactors" title="Template talk:Enzyme cofactors"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Enzyme_cofactors" title="Special:EditPage/Template:Enzyme cofactors"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Enzyme_cofactors" style="font-size:114%;margin:0 4em"><a href="/wiki/Enzyme" title="Enzyme">Enzyme</a> <a href="/wiki/Cofactor_(biochemistry)" title="Cofactor (biochemistry)">cofactors</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Active forms</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/Vitamin" title="Vitamin">vitamins</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/Thiamine_pyrophosphate" title="Thiamine pyrophosphate">TPP / ThDP</a> (B<sub>1</sub>)</li> <li><a href="/wiki/Flavin_mononucleotide" title="Flavin mononucleotide">FMN</a>, <a href="/wiki/Flavin_adenine_dinucleotide" title="Flavin adenine dinucleotide">FAD</a> (B<sub>2</sub>)</li> <li><a href="/wiki/Nicotinamide_adenine_dinucleotide" title="Nicotinamide adenine dinucleotide">NAD<sup>+</sup></a>, <a href="/wiki/Nicotinamide_adenine_dinucleotide" title="Nicotinamide adenine dinucleotide">NADH</a>, <a class="mw-selflink selflink">NADP<sup>+</sup></a>, <a class="mw-selflink selflink">NADPH</a> (B<sub>3</sub>)</li> <li><a href="/wiki/Coenzyme_A" title="Coenzyme A">Coenzyme A</a> (B<sub>5</sub>)</li> <li><a href="/wiki/Pyridoxal_phosphate" title="Pyridoxal phosphate">PLP / P5P</a> (B<sub>6</sub>)</li> <li><a href="/wiki/Biotin" title="Biotin">Biotin</a> (B<sub>7</sub>)</li> <li><a href="/wiki/Tetrahydrofolic_acid" title="Tetrahydrofolic acid">THFA / H<sub>4</sub>FA</a>, <a href="/wiki/Dihydrofolic_acid" title="Dihydrofolic acid">DHFA / H<sub>2</sub>FA</a>, <a href="/wiki/5,10-Methylenetetrahydrofolate" title="5,10-Methylenetetrahydrofolate">MTHF</a> (B<sub>9</sub>)</li> <li><a href="/wiki/Adenosylcobalamin" title="Adenosylcobalamin">AdoCbl</a>, <a href="/wiki/Methylcobalamin" title="Methylcobalamin">MeCbl</a> (B<sub>12</sub>)</li> <li><a href="/wiki/Vitamin_C" title="Vitamin C">Ascorbic acid</a> (C)</li> <li><a href="/wiki/Phytomenadione" title="Phytomenadione">Phylloquinone</a> (K<sub>1</sub>), <a href="/wiki/Vitamin_K" title="Vitamin K">Menaquinone</a> (K<sub>2</sub>)</li> <li><a href="/wiki/Coenzyme_F420" title="Coenzyme F420">Coenzyme F420</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cofactor_(biochemistry)#Non-vitamins" title="Cofactor (biochemistry)">non-vitamins</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/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a></li> <li><a href="/wiki/Cytidine_triphosphate" title="Cytidine triphosphate">CTP</a></li> <li><a href="/wiki/S-Adenosyl_methionine" title="S-Adenosyl methionine">SAMe</a></li> <li><a href="/wiki/3%27-Phosphoadenosine-5%27-phosphosulfate" title="3'-Phosphoadenosine-5'-phosphosulfate">PAPS</a></li> <li><a href="/wiki/Glutathione" title="Glutathione">GSH</a></li> <li><a href="/wiki/Coenzyme_B" title="Coenzyme B">Coenzyme B</a></li> <li><a href="/wiki/Cofactor_F430" title="Cofactor F430">Cofactor F430</a></li> <li><a href="/wiki/Coenzyme_M" title="Coenzyme M">Coenzyme M</a></li> <li><a href="/wiki/Coenzyme_Q10" title="Coenzyme Q10">Coenzyme Q</a></li> <li><a href="/wiki/Heme" title="Heme">Heme / Haem</a> (<a href="/wiki/Heme_A" title="Heme A">A</a>, <a href="/wiki/Heme_B" title="Heme B">B</a>, <a href="/wiki/Heme_C" title="Heme C">C</a>, <a href="/wiki/Heme_O" title="Heme O">O</a>)</li> <li><a href="/wiki/Lipoic_acid" title="Lipoic acid">Lipoic Acid</a></li> <li><a href="/wiki/Methanofuran" title="Methanofuran">Methanofuran</a></li> <li><a href="/wiki/Molybdopterin" title="Molybdopterin">Molybdopterin</a></li> <li><a href="/wiki/Mycofactocin" title="Mycofactocin">Mycofactocin</a></li> <li><a href="/wiki/Pyrroloquinoline_quinone" title="Pyrroloquinoline quinone">PQQ</a></li> <li><a href="/wiki/Tetrahydrobiopterin" title="Tetrahydrobiopterin">THB / BH<sub>4</sub></a></li> <li><a href="/wiki/Tetrahydromethanopterin" title="Tetrahydromethanopterin">THMPT / H<sub>4</sub>MPT</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Mineral_(nutrient)" title="Mineral (nutrient)">metal ions</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/Calcium" title="Calcium">Ca<sup>2+</sup></a></li> <li><a href="/wiki/Copper" title="Copper">Cu<sup>2+</sup></a></li> <li><a href="/wiki/Iron" title="Iron">Fe<sup>2+</sup>, Fe<sup>3+</sup></a></li> <li><a href="/wiki/Magnesium" title="Magnesium">Mg<sup>2+</sup></a></li> <li><a href="/wiki/Manganese" title="Manganese">Mn<sup>2+</sup></a></li> <li><a href="/wiki/Molybdenum" title="Molybdenum">Mo</a></li> <li><a href="/wiki/Nickel" title="Nickel">Ni<sup>2+</sup></a></li> <li><a href="/wiki/Zinc" title="Zinc">Zn<sup>2+</sup></a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Base forms</th><td 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