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<span>Biochemistry</span> </div> </a> <button aria-controls="toc-Biochemistry-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 Biochemistry subsection</span> </button> <ul id="toc-Biochemistry-sublist" class="vector-toc-list"> <li id="toc-Pyruvic_acid_production_by_glycolysis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pyruvic_acid_production_by_glycolysis"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>Pyruvic acid production by glycolysis</span> </div> </a> <ul id="toc-Pyruvic_acid_production_by_glycolysis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Decarboxylation_to_acetyl_CoA" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Decarboxylation_to_acetyl_CoA"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.2</span> <span>Decarboxylation to acetyl CoA</span> </div> </a> <ul id="toc-Decarboxylation_to_acetyl_CoA-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Carboxylation_to_oxaloacetate" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Carboxylation_to_oxaloacetate"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3</span> <span>Carboxylation to oxaloacetate</span> </div> </a> <ul id="toc-Carboxylation_to_oxaloacetate-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Transamination_to_alanine" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Transamination_to_alanine"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.4</span> <span>Transamination to alanine</span> </div> </a> <ul id="toc-Transamination_to_alanine-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reduction_to_lactate" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Reduction_to_lactate"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.5</span> <span>Reduction to lactate</span> </div> </a> <ul id="toc-Reduction_to_lactate-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Environmental_chemistry" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Environmental_chemistry"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.6</span> <span>Environmental chemistry</span> </div> </a> <ul id="toc-Environmental_chemistry-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Uses" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Uses</span> </div> </a> <ul id="toc-Uses-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">4</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Notes" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Notes"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Notes</span> </div> </a> <ul id="toc-Notes-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" title="Table of Contents" > <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 " 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Available in 54 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-54" 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">54 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%AD%D9%85%D8%B6_%D8%A7%D9%84%D8%A8%D9%8A%D8%B1%D9%88%D9%81%D9%8A%D9%83" title="حمض البيروفيك – Arabic" lang="ar" hreflang="ar" data-title="حمض البيروفيك" 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%BE%DB%8C%D8%B1%D9%88%DB%8C%DA%A9_%D8%A7%D8%B3%DB%8C%D8%AF" title="پیرویک اسید – South Azerbaijani" lang="azb" hreflang="azb" data-title="پیرویک اسید" 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%AA%E0%A6%BE%E0%A6%87%E0%A6%B0%E0%A7%81%E0%A6%AD%E0%A6%BF%E0%A6%95_%E0%A6%85%E0%A7%8D%E0%A6%AF%E0%A6%BE%E0%A6%B8%E0%A6%BF%E0%A6%A1" title="পাইরুভিক অ্যাসিড – Bangla" lang="bn" hreflang="bn" data-title="পাইরুভিক অ্যাসিড" 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%9F%D0%B8%D1%80%D0%BE%D0%B3%D1%80%D0%BE%D0%B7%D0%B4%D0%B5%D0%BD%D0%B0_%D0%BA%D0%B8%D1%81%D0%B5%D0%BB%D0%B8%D0%BD%D0%B0" title="Пирогроздена киселина – Bulgarian" lang="bg" hreflang="bg" data-title="Пирогроздена киселина" 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/Pirogro%C5%BE%C4%91ana_kiselina" title="Pirogrožđana kiselina – Bosnian" lang="bs" hreflang="bs" data-title="Pirogrožđana kiselina" 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/%C3%80cid_pir%C3%BAvic" title="Àcid pirúvic – Catalan" lang="ca" hreflang="ca" data-title="Àcid pirúvic" 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/Kyselina_pyrohroznov%C3%A1" title="Kyselina pyrohroznová – Czech" lang="cs" hreflang="cs" data-title="Kyselina pyrohroznová" 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/Pyruvat" title="Pyruvat – Danish" lang="da" hreflang="da" data-title="Pyruvat" 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/Brenztraubens%C3%A4ure" title="Brenztraubensäure – German" lang="de" hreflang="de" data-title="Brenztraubensäure" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%A0%CF%85%CF%81%CE%BF%CF%83%CF%84%CE%B1%CF%86%CF%85%CE%BB%CE%B9%CE%BA%CF%8C_%CE%BF%CE%BE%CF%8D" title="Πυροσταφυλικό οξύ – Greek" lang="el" hreflang="el" data-title="Πυροσταφυλικό οξύ" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/%C3%81cido_pir%C3%BAvico" title="Ácido pirúvico – Spanish" lang="es" hreflang="es" data-title="Ácido pirúvico" 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/Piruvata_acido" title="Piruvata acido – Esperanto" lang="eo" hreflang="eo" data-title="Piruvata acido" 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/Azido_pirubiko" title="Azido pirubiko – Basque" lang="eu" hreflang="eu" data-title="Azido pirubiko" 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/%D9%BE%DB%8C%D8%B1%D9%88%D9%88%DB%8C%DA%A9_%D8%A7%D8%B3%DB%8C%D8%AF" title="پیروویک اسید – Persian" lang="fa" hreflang="fa" data-title="پیروویک اسید" 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/Acide_pyruvique" title="Acide pyruvique – French" lang="fr" hreflang="fr" data-title="Acide pyruvique" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Aig%C3%A9ad_pior%C3%BAvach" title="Aigéad piorúvach – Irish" lang="ga" hreflang="ga" data-title="Aigéad piorúvach" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/%C3%81cido_pir%C3%BAvico" title="Ácido pirúvico – Galician" lang="gl" hreflang="gl" data-title="Ácido pirúvico" 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/%ED%94%BC%EB%A3%A8%EB%B8%8C%EC%82%B0" title="피루브산 – Korean" lang="ko" hreflang="ko" data-title="피루브산" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D5%8A%D5%AB%D6%80%D5%B8%D5%AD%D5%A1%D5%B2%D5%B8%D5%B2%D5%A1%D5%A9%D5%A9%D5%B8%D6%82" title="Պիրոխաղողաթթու – Armenian" lang="hy" hreflang="hy" data-title="Պիրոխաղողաթթու" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%AA%E0%A4%BE%E0%A4%87%E0%A4%B0%E0%A5%81%E0%A4%B5%E0%A4%BF%E0%A4%95_%E0%A4%85%E0%A4%AE%E0%A5%8D%E0%A4%B2" title="पाइरुविक अम्ल – Hindi" lang="hi" hreflang="hi" data-title="पाइरुविक अम्ल" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Pirogro%C5%BE%C4%91ana_kiselina" title="Pirogrožđana kiselina – Croatian" lang="hr" hreflang="hr" data-title="Pirogrožđana kiselina" 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/Asam_piruvat" title="Asam piruvat – Indonesian" lang="id" hreflang="id" data-title="Asam piruvat" 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/Acido_piruvico" title="Acido piruvico – Italian" lang="it" hreflang="it" data-title="Acido piruvico" 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%A4%D7%99%D7%A8%D7%95%D7%91%D7%98" title="פירובט – Hebrew" lang="he" hreflang="he" data-title="פירובט" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%9E%E1%83%98%E1%83%A0%E1%83%9D%E1%83%A7%E1%83%A3%E1%83%A0%E1%83%AB%E1%83%9C%E1%83%98%E1%83%A1_%E1%83%9B%E1%83%9F%E1%83%90%E1%83%95%E1%83%90" title="პიროყურძნის მჟავა – Georgian" lang="ka" hreflang="ka" data-title="პიროყურძნის მჟავა" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Acidum_pyruvicum" title="Acidum pyruvicum – Latin" lang="la" hreflang="la" data-title="Acidum pyruvicum" data-language-autonym="Latina" data-language-local-name="Latin" class="interlanguage-link-target"><span>Latina</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Pirov%C4%ABnogsk%C4%81be" title="Pirovīnogskābe – Latvian" lang="lv" hreflang="lv" data-title="Pirovīnogskābe" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-lb mw-list-item"><a href="https://lb.wikipedia.org/wiki/Pyruvat" title="Pyruvat – Luxembourgish" lang="lb" hreflang="lb" data-title="Pyruvat" 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/Pirosz%C5%91l%C5%91sav" title="Piroszőlősav – Hungarian" lang="hu" hreflang="hu" data-title="Piroszőlősav" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%9F%D0%B8%D1%80%D0%BE%D0%B3%D1%80%D0%BE%D0%B7%D0%B4%D0%BE%D0%B2%D0%B0_%D0%BA%D0%B8%D1%81%D0%B5%D0%BB%D0%B8%D0%BD%D0%B0" title="Пирогроздова киселина – Macedonian" lang="mk" hreflang="mk" data-title="Пирогроздова киселина" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Asid_piruvik" title="Asid piruvik – Malay" lang="ms" hreflang="ms" data-title="Asid piruvik" 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/Pyrodruivenzuur" title="Pyrodruivenzuur – Dutch" lang="nl" hreflang="nl" data-title="Pyrodruivenzuur" 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%94%E3%83%AB%E3%83%93%E3%83%B3%E9%85%B8" title="ピルビン酸 – Japanese" lang="ja" hreflang="ja" data-title="ピルビン酸" 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-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Pyrodruesyre" title="Pyrodruesyre – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Pyrodruesyre" 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-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Pirouzum_kislota" title="Pirouzum kislota – Uzbek" lang="uz" hreflang="uz" data-title="Pirouzum kislota" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Kwas_pirogronowy" title="Kwas pirogronowy – Polish" lang="pl" hreflang="pl" data-title="Kwas pirogronowy" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/%C3%81cido_pir%C3%BAvico" title="Ácido pirúvico – Portuguese" lang="pt" hreflang="pt" data-title="Ácido pirúvico" 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/Acid_piruvic" title="Acid piruvic – Romanian" lang="ro" hreflang="ro" data-title="Acid piruvic" 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%9F%D0%B8%D1%80%D0%BE%D0%B2%D0%B8%D0%BD%D0%BE%D0%B3%D1%80%D0%B0%D0%B4%D0%BD%D0%B0%D1%8F_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0" title="Пировиноградная кислота – Russian" lang="ru" hreflang="ru" data-title="Пировиноградная кислота" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-scn mw-list-item"><a href="https://scn.wikipedia.org/wiki/%C3%80citu_pir%C3%B9vicu" title="Àcitu pirùvicu – Sicilian" lang="scn" hreflang="scn" data-title="Àcitu pirùvicu" data-language-autonym="Sicilianu" data-language-local-name="Sicilian" class="interlanguage-link-target"><span>Sicilianu</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Pyruvic_acid" title="Pyruvic acid – Simple English" lang="en-simple" hreflang="en-simple" data-title="Pyruvic acid" 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 interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Kyselina_pyrohroznov%C3%A1" title="Kyselina pyrohroznová – Slovak" lang="sk" hreflang="sk" data-title="Kyselina pyrohroznová" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Piruvi%C4%8Dna_kislina" title="Piruvična kislina – Slovenian" lang="sl" hreflang="sl" data-title="Piruvična kislina" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Piruvinska_kiselina" title="Piruvinska kiselina – Serbian" lang="sr" hreflang="sr" data-title="Piruvinska kiselina" 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/Pirogro%C5%BE%C4%91ana_kiselina" title="Pirogrožđana kiselina – Serbo-Croatian" lang="sh" hreflang="sh" 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data-event-name="pinnable-header.vector-appearance.unpin">hide</button> </div> </div> </div> </nav> </div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Simplest of the alpha-keto acids</div> <style data-mw-deduplicate="TemplateStyles:r1268415487">.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%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}</style> <table class="infobox ib-chembox"> <caption>Pyruvic acid </caption> <tbody><tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center skin-invert-image" typeof="mw:File"><a href="/wiki/File:Brenztraubens%C3%A4ure.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Brenztraubens%C3%A4ure.svg/110px-Brenztraubens%C3%A4ure.svg.png" decoding="async" width="110" height="79" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Brenztraubens%C3%A4ure.svg/165px-Brenztraubens%C3%A4ure.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Brenztraubens%C3%A4ure.svg/220px-Brenztraubens%C3%A4ure.svg.png 2x" data-file-width="163" data-file-height="117" /></a><figcaption></figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Pyruvic-acid-3D-balls.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/dc/Pyruvic-acid-3D-balls.png/110px-Pyruvic-acid-3D-balls.png" decoding="async" width="110" height="76" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/dc/Pyruvic-acid-3D-balls.png/165px-Pyruvic-acid-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/dc/Pyruvic-acid-3D-balls.png/220px-Pyruvic-acid-3D-balls.png 2x" data-file-width="1100" data-file-height="764" /></a><figcaption></figcaption></figure> </td></tr></tbody></table> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; 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;">2-Oxopropanoic acid<sup id="cite_ref-iupac2013_1-1" class="reference"><a href="#cite_note-iupac2013-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature#Systematic_name" title="Chemical nomenclature">Systematic 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;">2-Oxopropionic acid</div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">Pyruvic acid<sup id="cite_ref-iupac2013_1-0" class="reference"><a href="#cite_note-iupac2013-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><br />α-Ketopropionic acid<br />Acetylformic acid<br />Pyroracemic acid<br />Acetylcarboxylic acid</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; 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=127-17-3">127-17-3</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%28C%28%3DO%29O%29C">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td>Abbreviations </td> <td>Pyr </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=32816">CHEBI:32816</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/ChEMBL1162144">ChEMBL1162144</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.1031.html">1031</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/DrugBank" title="DrugBank">DrugBank</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB00119">DB00119</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/100.004.387">100.004.387</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q213580#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=4809">4809</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/C00022">C00022</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><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/1060">1060</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/8558G7RUTR">8558G7RUTR</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/DTXSID2021650">DTXSID2021650</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q213580#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;"><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/C3H4O3/c1-2(4)3(5)6/h1H3,(H,5,6)<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: LCTONWCANYUPML-UHFFFAOYSA-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></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;"><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(C(=O)O)C</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; 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>C<sub>3</sub>H<sub>4</sub>O<sub>3</sub>  </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td>88.06<span class="nowrap"> </span>g/mol    </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>1.250<span class="nowrap"> </span>g/cm<sup>3</sup> </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>11.8 °C (53.2 °F; 284.9 K) </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>165 °C (329 °F; 438 K) </td></tr> <tr> <td><a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">Acidity</a> (p<i>K</i><sub>a</sub>) </td> <td>2.50<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> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Related compounds </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Other <a href="/wiki/Ion" title="Ion">anions</a></div> </td> <td><a href="/wiki/Pyruvate" class="mw-redirect" title="Pyruvate">Pyruvate</a><br /> <span typeof="mw:File"><a href="/wiki/File:Pyruvate_skeletal.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/ba/Pyruvate_skeletal.svg/99px-Pyruvate_skeletal.svg.png" decoding="async" width="99" height="91" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/ba/Pyruvate_skeletal.svg/149px-Pyruvate_skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/ba/Pyruvate_skeletal.svg/198px-Pyruvate_skeletal.svg.png 2x" data-file-width="1100" data-file-height="1011" /></a></span><br /><span typeof="mw:File"><a href="/wiki/File:Pyruvate-3D-balls.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8f/Pyruvate-3D-balls.png/100px-Pyruvate-3D-balls.png" decoding="async" width="100" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8f/Pyruvate-3D-balls.png/150px-Pyruvate-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8f/Pyruvate-3D-balls.png/200px-Pyruvate-3D-balls.png 2x" data-file-width="1100" data-file-height="878" /></a></span> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related <a href="/wiki/Keto-acid" class="mw-redirect" title="Keto-acid">keto-acids</a>, <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acids</a></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a href="/wiki/Acetic_acid" title="Acetic acid">Acetic acid</a></li><li><a href="/wiki/Glyoxylic_acid" title="Glyoxylic acid">Glyoxylic acid</a></li><li><a href="/wiki/Oxalic_acid" title="Oxalic acid">Oxalic acid</a></li><li><a href="/wiki/Propionic_acid" title="Propionic acid">Propionic acid</a></li><li><a href="/wiki/Acetoacetic_acid" title="Acetoacetic acid">Acetoacetic acid</a></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related compounds</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a href="/wiki/Propionaldehyde" title="Propionaldehyde">Propionaldehyde</a></li><li><a href="/wiki/Glyceraldehyde" title="Glyceraldehyde">Glyceraldehyde</a></li><li><a href="/wiki/Methylglyoxal" title="Methylglyoxal">Methylglyoxal</a></li><li><a href="/wiki/Sodium_pyruvate" title="Sodium pyruvate">Sodium pyruvate</a></li></ul></div> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; color:inherit; 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=464364811&page2=Pyruvic+acid">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>Pyruvic acid</b> (CH<sub>3</sub>COCOOH) is the simplest of the <a href="/wiki/Keto_acids" class="mw-redirect" title="Keto acids">alpha-keto acids</a>, with a <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a> and a <a href="/wiki/Ketone" title="Ketone">ketone</a> functional group. <b>Pyruvate</b>, the <a href="/wiki/Conjugate_acid" class="mw-redirect" title="Conjugate acid">conjugate base</a>, CH<sub>3</sub>COCOO<sup>−</sup>, is an <a href="/wiki/Metabolic_intermediate" title="Metabolic intermediate">intermediate</a> in several <a href="/wiki/Metabolic_pathway" title="Metabolic pathway">metabolic pathways</a> throughout the cell. </p><p>Pyruvic acid can be made from <a href="/wiki/Glucose" title="Glucose">glucose</a> through <a href="/wiki/Glycolysis" title="Glycolysis">glycolysis</a>, converted back to <a href="/wiki/Carbohydrate" title="Carbohydrate">carbohydrates</a> (such as glucose) via <a href="/wiki/Gluconeogenesis" title="Gluconeogenesis">gluconeogenesis</a>, or converted to <a href="/wiki/Fatty_acid" title="Fatty acid">fatty acids</a> through a reaction with <a href="/wiki/Acetyl-CoA" title="Acetyl-CoA">acetyl-CoA</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> It can also be used to construct the amino acid <a href="/wiki/Alanine" title="Alanine">alanine</a> and can be converted into <a href="/wiki/Ethanol" title="Ethanol">ethanol</a> or <a href="/wiki/Lactic_acid" title="Lactic acid">lactic acid</a> via <a href="/wiki/Fermentation" title="Fermentation">fermentation</a>. </p><p>Pyruvic acid supplies energy to <a href="/wiki/Cell_(biology)" title="Cell (biology)">cells</a> through the <a href="/wiki/Citric_acid_cycle" title="Citric acid cycle">citric acid cycle</a> (also known as the Krebs cycle) when oxygen is present (<a href="/wiki/Aerobic_respiration" class="mw-redirect" title="Aerobic respiration">aerobic respiration</a>), and alternatively <a href="/wiki/Lactic_acid_fermentation" title="Lactic acid fermentation">ferments</a> to produce <a href="/wiki/Lactic_acid" title="Lactic acid">lactate</a> when oxygen is lacking.<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="Chemistry">Chemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pyruvic_acid&action=edit&section=1" title="Edit section: Chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In 1834, <a href="/wiki/Th%C3%A9ophile-Jules_Pelouze" title="Théophile-Jules Pelouze">Théophile-Jules Pelouze</a> distilled <a href="/wiki/Tartaric_acid" title="Tartaric acid">tartaric acid</a> and isolated <a href="/wiki/Glutaric_acid" title="Glutaric acid">glutaric acid</a> and another unknown organic acid. <a href="/wiki/J%C3%B6ns_Jacob_Berzelius" title="Jöns Jacob Berzelius">Jöns Jacob Berzelius</a> characterized this other acid the following year and named pyruvic acid because it was distilled using heat.<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 correct molecular structure was deduced by the 1870s.<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> </p><p>Pyruvic acid is a colorless liquid with a smell similar to that of <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a> and is <a href="/wiki/Miscible" class="mw-redirect" title="Miscible">miscible</a> with water.<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> In the laboratory, pyruvic acid may be prepared by heating a mixture of <a href="/wiki/Tartaric_acid" title="Tartaric acid">tartaric acid</a> and <a href="/wiki/Potassium_hydrogen_sulfate" class="mw-redirect" title="Potassium hydrogen sulfate">potassium hydrogen sulfate</a>,<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> by the <a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">oxidation</a> of <a href="/wiki/Propylene_glycol" title="Propylene glycol">propylene glycol</a> by a strong oxidizer (e.g., <a href="/wiki/Potassium_permanganate" title="Potassium permanganate">potassium permanganate</a> or <a href="/wiki/Bleach" title="Bleach">bleach</a>), or by the hydrolysis of <a href="/wiki/Acetyl_cyanide" title="Acetyl cyanide">acetyl cyanide</a>, formed by reaction of <a href="/wiki/Acetyl_chloride" title="Acetyl chloride">acetyl chloride</a> with <a href="/wiki/Potassium_cyanide" title="Potassium cyanide">potassium cyanide</a>:<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (December 2023)">citation needed</span></a></i>]</sup> </p> <dl><dd>CH<sub>3</sub>COCl + KCN → CH<sub>3</sub>COCN + KCl</dd> <dd>CH<sub>3</sub>COCN → CH<sub>3</sub>COCOOH</dd></dl> <div class="mw-heading mw-heading2"><h2 id="Biochemistry">Biochemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pyruvic_acid&action=edit&section=2" title="Edit section: Biochemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1251242444">.mw-parser-output .ambox{border:1px solid #a2a9b1;border-left:10px solid #36c;background-color:#fbfbfb;box-sizing:border-box}.mw-parser-output .ambox+link+.ambox,.mw-parser-output .ambox+link+style+.ambox,.mw-parser-output .ambox+link+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+style+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+link+.ambox{margin-top:-1px}html body.mediawiki .mw-parser-output .ambox.mbox-small-left{margin:4px 1em 4px 0;overflow:hidden;width:238px;border-collapse:collapse;font-size:88%;line-height:1.25em}.mw-parser-output .ambox-speedy{border-left:10px solid #b32424;background-color:#fee7e6}.mw-parser-output .ambox-delete{border-left:10px solid #b32424}.mw-parser-output .ambox-content{border-left:10px solid #f28500}.mw-parser-output .ambox-style{border-left:10px solid #fc3}.mw-parser-output .ambox-move{border-left:10px solid #9932cc}.mw-parser-output .ambox-protection{border-left:10px solid #a2a9b1}.mw-parser-output .ambox .mbox-text{border:none;padding:0.25em 0.5em;width:100%}.mw-parser-output .ambox .mbox-image{border:none;padding:2px 0 2px 0.5em;text-align:center}.mw-parser-output .ambox .mbox-imageright{border:none;padding:2px 0.5em 2px 0;text-align:center}.mw-parser-output .ambox .mbox-empty-cell{border:none;padding:0;width:1px}.mw-parser-output .ambox .mbox-image-div{width:52px}@media(min-width:720px){.mw-parser-output .ambox{margin:0 10%}}@media print{body.ns-0 .mw-parser-output .ambox{display:none!important}}</style><table class="box-More_citations_needed plainlinks metadata ambox ambox-content ambox-Refimprove" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><a href="/wiki/File:Question_book-new.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/50px-Question_book-new.svg.png" decoding="async" width="50" height="39" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/75px-Question_book-new.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/100px-Question_book-new.svg.png 2x" data-file-width="512" data-file-height="399" /></a></span></div></td><td class="mbox-text"><div class="mbox-text-span">This article <b>needs additional citations for <a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability">verification</a></b>.<span class="hide-when-compact"> Please help <a href="/wiki/Special:EditPage/Pyruvic_acid" title="Special:EditPage/Pyruvic acid">improve this article</a> by <a href="/wiki/Help:Referencing_for_beginners" title="Help:Referencing for beginners">adding citations to reliable sources</a>. Unsourced material may be challenged and removed.<br /><small><span class="plainlinks"><i>Find sources:</i> <a rel="nofollow" class="external text" href="https://www.google.com/search?as_eq=wikipedia&q=%22Pyruvic+acid%22">"Pyruvic acid"</a> – <a rel="nofollow" class="external text" href="https://www.google.com/search?tbm=nws&q=%22Pyruvic+acid%22+-wikipedia&tbs=ar:1">news</a> <b>·</b> <a rel="nofollow" class="external text" href="https://www.google.com/search?&q=%22Pyruvic+acid%22&tbs=bkt:s&tbm=bks">newspapers</a> <b>·</b> <a rel="nofollow" class="external text" href="https://www.google.com/search?tbs=bks:1&q=%22Pyruvic+acid%22+-wikipedia">books</a> <b>·</b> <a rel="nofollow" class="external text" href="https://scholar.google.com/scholar?q=%22Pyruvic+acid%22">scholar</a> <b>·</b> <a rel="nofollow" class="external text" href="https://www.jstor.org/action/doBasicSearch?Query=%22Pyruvic+acid%22&acc=on&wc=on">JSTOR</a></span></small></span> <span class="date-container"><i>(<span class="date">December 2023</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> <p>Pyruvate is an important <a href="/wiki/Chemical_compound" title="Chemical compound">chemical compound</a> in <a href="/wiki/Biochemistry" title="Biochemistry">biochemistry</a>. It is the output of the metabolism of <a href="/wiki/Glucose" title="Glucose">glucose</a> known as <a href="/wiki/Glycolysis" title="Glycolysis">glycolysis</a>.<sup id="cite_ref-lehninger528_10-0" class="reference"><a href="#cite_note-lehninger528-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> One molecule of <a href="/wiki/Glucose" title="Glucose">glucose</a> breaks down into two molecules of pyruvate,<sup id="cite_ref-lehninger528_10-1" class="reference"><a href="#cite_note-lehninger528-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> which are then used to provide further energy, in one of two ways. Pyruvate is converted into <a href="/wiki/Acetyl-CoA" title="Acetyl-CoA">acetyl-coenzyme A</a>, which is the main input for a series of reactions known as the <a href="/wiki/Citric_acid_cycle" title="Citric acid cycle">Krebs cycle</a> (also known as the citric acid cycle or tricarboxylic acid cycle). Pyruvate is also converted to <a href="/wiki/Oxaloacetate" class="mw-redirect" title="Oxaloacetate">oxaloacetate</a> by an <a href="/wiki/Anaplerotic_reactions" title="Anaplerotic reactions">anaplerotic reaction</a>, which replenishes Krebs cycle intermediates; also, the oxaloacetate is used for <a href="/wiki/Gluconeogenesis" title="Gluconeogenesis">gluconeogenesis</a>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (December 2023)">citation needed</span></a></i>]</sup> </p><p>These reactions are named after <a href="/wiki/Hans_Adolf_Krebs" class="mw-redirect" title="Hans Adolf Krebs">Hans Adolf Krebs</a>, the biochemist awarded the 1953 <a href="/wiki/Nobel_Prize" title="Nobel Prize">Nobel Prize</a> for physiology, jointly with <a href="/wiki/Fritz_Lipmann" class="mw-redirect" title="Fritz Lipmann">Fritz Lipmann</a>, for research into metabolic processes. The cycle is also known as the <a href="/wiki/Citric_acid_cycle" title="Citric acid cycle">citric acid cycle</a> or tricarboxylic acid cycle, because citric acid is one of the intermediate compounds formed during the reactions.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (December 2023)">citation needed</span></a></i>]</sup> </p><p>If insufficient oxygen is available, the acid is broken down <a href="/wiki/Anaerobe" class="mw-redirect" title="Anaerobe">anaerobically</a>, creating <a href="/wiki/Lactic_acid" title="Lactic acid">lactate</a> in animals and <a href="/wiki/Ethanol" title="Ethanol">ethanol</a> in plants and microorganisms (and in <a href="/wiki/Carp" title="Carp">carp</a><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>). Pyruvate from glycolysis is converted by <a href="/wiki/Fermentation_(biochemistry)" class="mw-redirect" title="Fermentation (biochemistry)">fermentation</a> to <a href="/wiki/Lactic_acid" title="Lactic acid">lactate</a> using the <a href="/wiki/Enzyme" title="Enzyme">enzyme</a> <a href="/wiki/Lactate_dehydrogenase" title="Lactate dehydrogenase">lactate dehydrogenase</a> and the <a href="/wiki/Coenzyme" class="mw-redirect" title="Coenzyme">coenzyme</a> <a href="/wiki/NADH" class="mw-redirect" title="NADH">NADH</a> in lactate <a href="/wiki/Fermentation_(biochemistry)" class="mw-redirect" title="Fermentation (biochemistry)">fermentation</a>, or to <a href="/wiki/Acetaldehyde" title="Acetaldehyde">acetaldehyde</a> (with the enzyme <a href="/wiki/Pyruvate_decarboxylase" title="Pyruvate decarboxylase">pyruvate decarboxylase</a>) and then to <a href="/wiki/Ethanol" title="Ethanol">ethanol</a> in <a href="/wiki/Ethanol_fermentation" title="Ethanol fermentation">alcoholic fermentation</a>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (December 2023)">citation needed</span></a></i>]</sup> </p><p>Pyruvate is a key intersection in the network of <a href="/wiki/Metabolic_pathway" title="Metabolic pathway">metabolic pathways</a>. Pyruvate can be converted into <a href="/wiki/Carbohydrate" title="Carbohydrate">carbohydrates</a> via <a href="/wiki/Gluconeogenesis" title="Gluconeogenesis">gluconeogenesis</a>, to <a href="/wiki/Fatty_acid" title="Fatty acid">fatty acids</a> or energy through <a href="/wiki/Acetyl-CoA" title="Acetyl-CoA">acetyl-CoA</a>, to the <a href="/wiki/Amino_acid" title="Amino acid">amino acid</a> <a href="/wiki/Alanine" title="Alanine">alanine</a>, and to <a href="/wiki/Ethanol" title="Ethanol">ethanol</a>. Therefore, it unites several key metabolic processes.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (December 2023)">citation needed</span></a></i>]</sup> </p> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Blood_values_sorted_by_mass_and_molar_concentration.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/cb/Blood_values_sorted_by_mass_and_molar_concentration.png/450px-Blood_values_sorted_by_mass_and_molar_concentration.png" decoding="async" width="450" height="65" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/cb/Blood_values_sorted_by_mass_and_molar_concentration.png/675px-Blood_values_sorted_by_mass_and_molar_concentration.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/cb/Blood_values_sorted_by_mass_and_molar_concentration.png/900px-Blood_values_sorted_by_mass_and_molar_concentration.png 2x" data-file-width="6798" data-file-height="977" /></a><figcaption><a href="/wiki/Reference_ranges_for_blood_tests" title="Reference ranges for blood tests">Reference ranges for blood tests</a>, comparing blood content of pyruvate (shown in violet near middle) with other constituents.</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Pyruvic_acid_production_by_glycolysis">Pyruvic acid production by glycolysis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pyruvic_acid&action=edit&section=3" title="Edit section: Pyruvic acid production by glycolysis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In the last step of <a href="/wiki/Glycolysis" title="Glycolysis">glycolysis</a>, <a href="/wiki/Phosphoenolpyruvic_acid" title="Phosphoenolpyruvic acid">phosphoenolpyruvate</a> (PEP) is converted to pyruvate by <a href="/wiki/Pyruvate_kinase" title="Pyruvate kinase">pyruvate kinase</a>. This reaction is strongly exergonic and irreversible; in <a href="/wiki/Gluconeogenesis" title="Gluconeogenesis">gluconeogenesis</a>, it takes two enzymes, <a href="/wiki/Pyruvate_carboxylase" title="Pyruvate carboxylase">pyruvate carboxylase</a> and <a href="/wiki/PEP_carboxykinase" class="mw-redirect" title="PEP carboxykinase">PEP carboxykinase</a>, to catalyze the reverse transformation of pyruvate to PEP.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (December 2023)">citation needed</span></a></i>]</sup> </p> <table style="background-color:var(--background-color-base);font-family:inherit;"> <tbody><tr> <td style="text-align:center;font-family:inherit;background-color:light-dark(lightgreen,darkgreen);color:var(--color-base);"><a href="/wiki/Phosphoenolpyruvate" class="mw-redirect" title="Phosphoenolpyruvate">phosphoenolpyruvate</a> </td> <td colspan="2" style="text-align:center;font-family:inherit;color:var(--color-base);background-color:light-dark(pink,#6a331d)" width="75px"><a href="/wiki/Pyruvate_kinase" title="Pyruvate kinase">pyruvate kinase</a> </td> <td style="text-align:center;font-family:inherit;color:var(--color-base);background-color:light-dark(lightgreen,darkgreen);">pyruvic acid </td></tr> <tr> <td rowspan="5" style="text-align:center;color:var(--color-base);"><span class="mw-default-size skin-invert-image" 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/77px-Phosphoenolpyruvate_wpmp.svg.png" decoding="async" width="77" height="109" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bc/Phosphoenolpyruvate_wpmp.svg/116px-Phosphoenolpyruvate_wpmp.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bc/Phosphoenolpyruvate_wpmp.svg/154px-Phosphoenolpyruvate_wpmp.svg.png 2x" data-file-width="77" data-file-height="109" /></a></span> </td> <td colspan="2" style="text-align:center;" width="75">  </td> <td rowspan="5" style="text-align:center;color:var(--color-base);"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Pyruvic-acid-2D-skeletal.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5d/Pyruvic-acid-2D-skeletal.svg/90px-Pyruvic-acid-2D-skeletal.svg.png" decoding="async" width="90" height="83" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5d/Pyruvic-acid-2D-skeletal.svg/135px-Pyruvic-acid-2D-skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5d/Pyruvic-acid-2D-skeletal.svg/180px-Pyruvic-acid-2D-skeletal.svg.png 2x" data-file-width="1100" data-file-height="1011" /></a></span> </td></tr> <tr> <td style="text-align:center;color:var(--color-base);" width="38px"><a href="/wiki/Adenosine_diphosphate" title="Adenosine diphosphate">ADP</a> </td> <td style="text-align:center;color:var(--color-base);" width="38px"><a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a> </td></tr> <tr> <td colspan="2" width="75px" style="text-align:center;color:var(--color-base);"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Biochem_reaction_arrow_reversible_YYYY_horiz_med.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/19/Biochem_reaction_arrow_reversible_YYYY_horiz_med.svg/75px-Biochem_reaction_arrow_reversible_YYYY_horiz_med.svg.png" decoding="async" width="75" height="75" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/19/Biochem_reaction_arrow_reversible_YYYY_horiz_med.svg/113px-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/150px-Biochem_reaction_arrow_reversible_YYYY_horiz_med.svg.png 2x" data-file-width="75" data-file-height="75" /></a></span> </td></tr> <tr> <td style="text-align:center;color:var(--color-base);" width="38px"><a href="/wiki/Adenosine_diphosphate" title="Adenosine diphosphate">ADP</a> </td> <td style="text-align:center;color:var(--color-base);" width="38px"><a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a> </td></tr> <tr> <td colspan="2" style="text-align:center;" width="75">  </td></tr> <tr> <td>  </td> <td colspan="2" style="text-align:center;font-family:inherit;color:var(--color-base);background-color:light-dark(pink,#6a331d)" width="75"><a href="/wiki/Pyruvate_carboxylase" title="Pyruvate carboxylase">pyruvate carboxylase</a> and <a href="/wiki/PEP_carboxykinase" class="mw-redirect" title="PEP carboxykinase">PEP carboxykinase</a> </td> <td style="text-align:right;"> </td></tr></tbody></table> <p><span style="font-size: x-small;">Compound <a rel="nofollow" class="external text" href="http://www.genome.jp/dbget-bin/www_bget?compound+C00074">C00074</a> at <a href="/wiki/KEGG" title="KEGG">KEGG</a> Pathway Database.</span> <span style="font-size: x-small;">Enzyme <a rel="nofollow" class="external text" href="http://www.genome.jp/dbget-bin/www_bget?enzyme+2.7.1.40">2.7.1.40</a> at <a href="/wiki/KEGG" title="KEGG">KEGG</a> Pathway Database.</span> <span style="font-size: x-small;">Compound <a rel="nofollow" class="external text" href="http://www.genome.jp/dbget-bin/www_bget?compound+C00022">C00022</a> at <a href="/wiki/KEGG" title="KEGG">KEGG</a> Pathway Database.</span> </p><p><i>Click on genes, proteins and metabolites below to link to respective articles.</i><sup id="cite_ref-WikiPathways_12-0" class="reference"><a href="#cite_note-WikiPathways-12"><span class="cite-bracket">[</span>§ 1<span class="cite-bracket">]</span></a></sup> </p> <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: -888.666666666667px; left: -95px; width: {{{bSize}}}px"><div class="noresize">[[File:<div class="noresize thumb tnone" style=";"> <div class="thumbinner" style="overflow:hidden;width:1017px;"> <div class="thumbimage" style="overflow:hidden; position:relative; background-color:white;"> <div style=";left:0px; top:0px; width:1015px; position:absolute;"> <figure class="mw-default-size mw-halign-right noresize" typeof="mw:File"><a href="/wiki/Glycolysis#Interactive_pathway_map" title="Go to pathway article"><img alt="GlycolysisGluconeogenesis_WP534" src="//upload.wikimedia.org/wikipedia/commons/a/aa/WP534.png" decoding="async" width="1015" height="1341" class="mw-file-element" data-file-width="1015" data-file-height="1341" usemap="#ImageMap_868cf5ca7e758742" /></a><map name="ImageMap_868cf5ca7e758742"><area href="/wiki/2-Phosphoglyceric_acid" shape="rect" coords="223,823,323,843" alt="go to article" title="go to article" /><area href="/wiki/Dihydrolipoyl_transacetylase" shape="rect" coords="696,1192,759,1212" alt="go to article" title="go to article" /><area href="/wiki/Malic_acid" shape="rect" coords="801,1025,901,1045" alt="go to article" title="go to article" /><area href="/wiki/Malate_dehydrogenase" shape="rect" coords="555,986,615,1006" alt="go to article" title="go to article" /><area 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article" title="go to article" /><area href="/wiki/Pentose_phosphate_pathway" shape="rect" coords="540,310,733,330" alt="go to article" title="go to article" /><area rel="nofollow" href="http://www.wikipathways.org/index.php/Pathway:WP500" class="plainlinks" shape="rect" coords="542,354,705,374" alt="go to WikiPathways" title="go to WikiPathways" /><area href="/wiki/Citric_acid_cycle" shape="rect" coords="870,1144,965,1164" alt="go to article" title="go to article" /><area rel="nofollow" href="https://www.ncbi.nlm.nih.gov/gene/51660" class="plainlinks" shape="rect" coords="593,1071,673,1091" alt="go to Entrez" title="go to Entrez" /><area href="/wiki/BRP44" shape="rect" coords="593,1091,673,1111" alt="go to article" title="go to article" /></map><figcaption></figcaption></figure></div> </div> <div class="thumbcaption"></div> </div></div>|alt=Glycolysis and Gluconeogenesis <a rel="nofollow" class="external text" href="http://www.wikipathways.org/index.php/Pathway:WP534">edit</a>]]</div></div> </div> <div class="thumbcaption"> <div class="magnify"><a href="/wiki/File:WP534.png" title="File:WP534.png"> </a></div>Glycolysis and Gluconeogenesis <a rel="nofollow" class="external text" href="http://www.wikipathways.org/index.php/Pathway:WP534">edit</a> </div> </div> </div> <div style="clear:both;" class=""></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"><ol class="references"> <li id="cite_note-WikiPathways-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-WikiPathways_12-0">^</a></b></span> <span class="reference-text">The interactive pathway map can be edited at WikiPathways: <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="http://www.wikipathways.org/index.php/Pathway:WP534">"GlycolysisGluconeogenesis_WP534"</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=GlycolysisGluconeogenesis_WP534&rft_id=http%3A%2F%2Fwww.wikipathways.org%2Findex.php%2FPathway%3AWP534&rfr_id=info%3Asid%2Fen.wikipedia.org%3APyruvic+acid" class="Z3988"></span></span> </li> </ol></div></div> </div> <div class="mw-heading mw-heading3"><h3 id="Decarboxylation_to_acetyl_CoA">Decarboxylation to acetyl CoA</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pyruvic_acid&action=edit&section=4" title="Edit section: Decarboxylation to acetyl CoA"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Pyruvate_decarboxylation" title="Pyruvate decarboxylation">Pyruvate decarboxylation</a> by the <a href="/wiki/Pyruvate_dehydrogenase_complex" title="Pyruvate dehydrogenase complex">pyruvate dehydrogenase complex</a> produces <a href="/wiki/Acetyl-CoA" title="Acetyl-CoA">acetyl-CoA</a>. </p> <table style="background-color:var(--background-color-base);font-family:inherit;"> <tbody><tr> <td style="text-align:center;font-family:inherit;background-color:light-dark(lightgreen,darkgreen);color:var(--color-base);">pyruvate </td> <td colspan="2" style="text-align:center;font-family:inherit;color:var(--color-base);background-color:light-dark(pink,#6a331d)" width="75px"><a href="/wiki/Pyruvate_dehydrogenase_complex" title="Pyruvate dehydrogenase complex">pyruvate dehydrogenase complex</a> </td> <td style="text-align:center;font-family:inherit;color:var(--color-base);background-color:light-dark(lightgreen,darkgreen);"><a href="/wiki/Acetyl-CoA" title="Acetyl-CoA">acetyl-CoA</a> </td></tr> <tr> <td rowspan="5" style="text-align:center;color:var(--color-base);"><span class="mw-default-size skin-invert-image" typeof="mw:File"><a href="/wiki/File:Pyruvate_wpmp.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/c/c7/Pyruvate_wpmp.png" decoding="async" width="63" height="62" class="mw-file-element" data-file-width="63" data-file-height="62" /></a></span> </td> <td colspan="2" style="text-align:center;" width="75">  </td> <td rowspan="5" style="text-align:center;color:var(--color-base);"><span class="mw-default-size skin-invert-image" typeof="mw:File"><a href="/wiki/File:Acetyl-CoA.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/89/Acetyl-CoA.svg/176px-Acetyl-CoA.svg.png" decoding="async" width="176" height="82" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/89/Acetyl-CoA.svg/264px-Acetyl-CoA.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/89/Acetyl-CoA.svg/352px-Acetyl-CoA.svg.png 2x" data-file-width="176" data-file-height="82" /></a></span> </td></tr> <tr> <td style="text-align:center;color:var(--color-base);" width="38px"><a href="/wiki/Coenzyme_A" title="Coenzyme A">CoA</a> <b>+</b> NAD<sup>+</sup> </td> <td style="text-align:center;color:var(--color-base);" width="38px">CO<sub>2</sub> <b>+</b> NADH <b>+</b> H<sup>+</sup> </td></tr> <tr> <td colspan="2" width="75px" style="text-align:center;color:var(--color-base);"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Biochem_reaction_arrow_forward_YYNN_horiz_med.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/85/Biochem_reaction_arrow_forward_YYNN_horiz_med.svg/75px-Biochem_reaction_arrow_forward_YYNN_horiz_med.svg.png" decoding="async" width="75" height="75" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/85/Biochem_reaction_arrow_forward_YYNN_horiz_med.svg/113px-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/150px-Biochem_reaction_arrow_forward_YYNN_horiz_med.svg.png 2x" data-file-width="75" data-file-height="75" /></a></span> </td></tr> <tr> <td style="text-align:center;color:var(--color-base);" width="38px"> </td> <td style="text-align:center;color:var(--color-base);" width="38px"> </td></tr></tbody></table> <p><br /> </p> <div class="mw-heading mw-heading3"><h3 id="Carboxylation_to_oxaloacetate">Carboxylation to oxaloacetate</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pyruvic_acid&action=edit&section=5" title="Edit section: Carboxylation to oxaloacetate"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Carboxylation by <a href="/wiki/Pyruvate_carboxylase" title="Pyruvate carboxylase">pyruvate carboxylase</a> produces <a href="/wiki/Oxaloacetic_acid" title="Oxaloacetic acid">oxaloacetate</a>. </p> <table style="background-color:var(--background-color-base);font-family:inherit;"> <tbody><tr> <td style="text-align:center;font-family:inherit;background-color:light-dark(lightgreen,darkgreen);color:var(--color-base);">pyruvate </td> <td colspan="2" style="text-align:center;font-family:inherit;color:var(--color-base);background-color:light-dark(pink,#6a331d)" width="75px"><a href="/wiki/Pyruvate_carboxylase" title="Pyruvate carboxylase">pyruvate carboxylase</a> </td> <td style="text-align:center;font-family:inherit;color:var(--color-base);background-color:light-dark(lightgreen,darkgreen);"><a href="/wiki/Oxaloacetate" class="mw-redirect" title="Oxaloacetate">oxaloacetate</a> </td></tr> <tr> <td rowspan="5" style="text-align:center;color:var(--color-base);"><span class="mw-default-size skin-invert-image" typeof="mw:File"><a href="/wiki/File:Pyruvate_wpmp.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/c/c7/Pyruvate_wpmp.png" decoding="async" width="63" height="62" class="mw-file-element" data-file-width="63" data-file-height="62" /></a></span> </td> <td colspan="2" style="text-align:center;" width="75">  </td> <td rowspan="5" style="text-align:center;color:var(--color-base);"><span class="mw-default-size skin-invert-image" typeof="mw:File"><a href="/wiki/File:Oxaloacetate_wpmp.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/c/c8/Oxaloacetate_wpmp.png" decoding="async" width="72" height="119" class="mw-file-element" data-file-width="72" data-file-height="119" /></a></span> </td></tr> <tr> <td style="text-align:center;color:var(--color-base);" width="38px">ATP <b>+</b> CO<sub>2</sub> </td> <td style="text-align:center;color:var(--color-base);" width="38px">ADP <b>+</b> P<sub>i</sub> </td></tr> <tr> <td colspan="2" width="75px" style="text-align:center;color:var(--color-base);"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Biochem_reaction_arrow_forward_YYNN_horiz_med.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/85/Biochem_reaction_arrow_forward_YYNN_horiz_med.svg/75px-Biochem_reaction_arrow_forward_YYNN_horiz_med.svg.png" decoding="async" width="75" height="75" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/85/Biochem_reaction_arrow_forward_YYNN_horiz_med.svg/113px-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/150px-Biochem_reaction_arrow_forward_YYNN_horiz_med.svg.png 2x" data-file-width="75" data-file-height="75" /></a></span> </td></tr> <tr> <td style="text-align:center;color:var(--color-base);" width="38px"> </td> <td style="text-align:center;color:var(--color-base);" width="38px"> </td></tr></tbody></table> <p><br /> </p> <div class="mw-heading mw-heading3"><h3 id="Transamination_to_alanine">Transamination to alanine</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pyruvic_acid&action=edit&section=6" title="Edit section: Transamination to alanine"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Transamination by <a href="/wiki/Alanine_transaminase" title="Alanine transaminase">alanine transaminase</a> produces <a href="/wiki/Alanine" title="Alanine">alanine</a>. </p> <table style="background-color:var(--background-color-base);font-family:inherit;"> <tbody><tr> <td style="text-align:center;font-family:inherit;background-color:light-dark(lightgreen,darkgreen);color:var(--color-base);">pyruvate </td> <td colspan="2" style="text-align:center;font-family:inherit;color:var(--color-base);background-color:light-dark(pink,#6a331d)" width="75px"><a href="/wiki/Alanine_transaminase" title="Alanine transaminase">alanine transaminase</a> </td> <td style="text-align:center;font-family:inherit;color:var(--color-base);background-color:light-dark(lightgreen,darkgreen);"><a href="/wiki/Alanine" title="Alanine">alanine</a> </td></tr> <tr> <td rowspan="5" style="text-align:center;color:var(--color-base);"><span class="mw-default-size skin-invert-image" typeof="mw:File"><a href="/wiki/File:Pyruvate_wpmp.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/c/c7/Pyruvate_wpmp.png" decoding="async" width="63" height="62" class="mw-file-element" data-file-width="63" data-file-height="62" /></a></span> </td> <td colspan="2" style="text-align:center;" width="75">  </td> <td rowspan="5" style="text-align:center;color:var(--color-base);"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:L-alanine-skeletal.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2a/L-alanine-skeletal.svg/100px-L-alanine-skeletal.svg.png" decoding="async" width="100" height="71" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2a/L-alanine-skeletal.svg/150px-L-alanine-skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2a/L-alanine-skeletal.svg/200px-L-alanine-skeletal.svg.png 2x" data-file-width="310" data-file-height="221" /></a></span> </td></tr> <tr> <td style="text-align:center;color:var(--color-base);" width="38px"><a href="/wiki/Glutamate" class="mw-redirect" title="Glutamate">glutamate</a> </td> <td style="text-align:center;color:var(--color-base);" width="38px"><a href="/wiki/%CE%91-ketoglutarate" class="mw-redirect" title="Α-ketoglutarate">α-ketoglutarate</a> </td></tr> <tr> <td colspan="2" width="75px" style="text-align:center;color:var(--color-base);"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Biochem_reaction_arrow_reversible_YYYY_horiz_med.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/19/Biochem_reaction_arrow_reversible_YYYY_horiz_med.svg/75px-Biochem_reaction_arrow_reversible_YYYY_horiz_med.svg.png" decoding="async" width="75" height="75" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/19/Biochem_reaction_arrow_reversible_YYYY_horiz_med.svg/113px-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/150px-Biochem_reaction_arrow_reversible_YYYY_horiz_med.svg.png 2x" data-file-width="75" data-file-height="75" /></a></span> </td></tr> <tr> <td style="text-align:center;color:var(--color-base);" width="38px"><a href="/wiki/Glutamate" class="mw-redirect" title="Glutamate">glutamate</a> </td> <td style="text-align:center;color:var(--color-base);" width="38px"><a href="/wiki/%CE%91-ketoglutarate" class="mw-redirect" title="Α-ketoglutarate">α-ketoglutarate</a> </td></tr></tbody></table> <p><br /> </p> <div class="mw-heading mw-heading3"><h3 id="Reduction_to_lactate">Reduction to lactate</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pyruvic_acid&action=edit&section=7" title="Edit section: Reduction to lactate"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Reduction by <a href="/wiki/Lactate_dehydrogenase" title="Lactate dehydrogenase">lactate dehydrogenase</a> produces <a href="/wiki/Lactic_acid" title="Lactic acid">lactate</a>. </p> <table style="background-color:var(--background-color-base);font-family:inherit;"> <tbody><tr> <td style="text-align:center;font-family:inherit;background-color:light-dark(lightgreen,darkgreen);color:var(--color-base);">pyruvate </td> <td colspan="2" style="text-align:center;font-family:inherit;color:var(--color-base);background-color:light-dark(pink,#6a331d)" width="75px"><a href="/wiki/Lactate_dehydrogenase" title="Lactate dehydrogenase">lactate dehydrogenase</a> </td> <td style="text-align:center;font-family:inherit;color:var(--color-base);background-color:light-dark(lightgreen,darkgreen);"><a href="/wiki/Lactic_acid" title="Lactic acid">lactate</a> </td></tr> <tr> <td rowspan="5" style="text-align:center;color:var(--color-base);"><span class="mw-default-size skin-invert-image" typeof="mw:File"><a href="/wiki/File:Pyruvate_wpmp.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/c/c7/Pyruvate_wpmp.png" decoding="async" width="63" height="62" class="mw-file-element" data-file-width="63" data-file-height="62" /></a></span> </td> <td colspan="2" style="text-align:center;" width="75">  </td> <td rowspan="5" style="text-align:center;color:var(--color-base);"><span class="mw-default-size skin-invert-image" typeof="mw:File"><a href="/wiki/File:Lactic-acid-skeletal.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d3/Lactic-acid-skeletal.svg/128px-Lactic-acid-skeletal.svg.png" decoding="async" width="128" height="117" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d3/Lactic-acid-skeletal.svg/192px-Lactic-acid-skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d3/Lactic-acid-skeletal.svg/256px-Lactic-acid-skeletal.svg.png 2x" data-file-width="128" data-file-height="117" /></a></span> </td></tr> <tr> <td style="text-align:center;color:var(--color-base);" width="38px">NADH </td> <td style="text-align:center;color:var(--color-base);" width="38px">NAD<sup>+</sup> </td></tr> <tr> <td colspan="2" width="75px" style="text-align:center;color:var(--color-base);"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Biochem_reaction_arrow_reversible_YYYY_horiz_med.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/19/Biochem_reaction_arrow_reversible_YYYY_horiz_med.svg/75px-Biochem_reaction_arrow_reversible_YYYY_horiz_med.svg.png" decoding="async" width="75" height="75" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/19/Biochem_reaction_arrow_reversible_YYYY_horiz_med.svg/113px-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/150px-Biochem_reaction_arrow_reversible_YYYY_horiz_med.svg.png 2x" data-file-width="75" data-file-height="75" /></a></span> </td></tr> <tr> <td style="text-align:center;color:var(--color-base);" width="38px">NADH </td> <td style="text-align:center;color:var(--color-base);" width="38px">NAD<sup>+</sup> </td></tr></tbody></table> <p><br /> </p> <div class="mw-heading mw-heading3"><h3 id="Environmental_chemistry">Environmental chemistry</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pyruvic_acid&action=edit&section=8" title="Edit section: Environmental chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Pyruvic acid is an abundant carboxylic acid in <a href="/wiki/Secondary_organic_aerosol" title="Secondary organic aerosol">secondary organic aerosols</a>.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Uses">Uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pyruvic_acid&action=edit&section=9" title="Edit section: Uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Pyruvate is sold as a <a href="/wiki/Anti-obesity_medication" title="Anti-obesity medication">weight-loss supplement</a>, though credible science has yet to back this claim. A <a href="/wiki/Clinical_research" title="Clinical research">systematic review</a> of six <a href="/wiki/Clinical_trial" title="Clinical trial">trials</a> found a statistically significant difference in body weight with pyruvate compared to <a href="/wiki/Placebo" title="Placebo">placebo</a>. However, all of the trials had methodological weaknesses and the magnitude of the effect was small. The review also identified <a href="/wiki/Adverse_effect" title="Adverse effect">adverse events</a> associated with pyruvate such as diarrhea, bloating, gas, and increase in <a href="/wiki/Low-density_lipoprotein" title="Low-density lipoprotein">low-density lipoprotein</a> (LDL) cholesterol. The authors concluded that there was insufficient evidence to support the use of pyruvate for weight loss.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p><p>There is also <i><a href="/wiki/In_vitro" title="In vitro">in vitro</a></i> as well as <i><a href="/wiki/In_vivo" title="In vivo">in vivo</a></i> evidence in hearts that pyruvate improves metabolism by <a href="/wiki/NADH" class="mw-redirect" title="NADH">NADH</a> production stimulation and increases cardiac function.<sup id="cite_ref-Functional_response_of_the_isolated,_perfused_normoxic_heart_to_pyruvate_dehydrogenase_activation_by_dichloroacetate_and_pyruvate._15-0" class="reference"><a href="#cite_note-Functional_response_of_the_isolated,_perfused_normoxic_heart_to_pyruvate_dehydrogenase_activation_by_dichloroacetate_and_pyruvate.-15"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p> <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=Pyruvic_acid&action=edit&section=10" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Pyruvate_scale" title="Pyruvate scale">Pyruvate scale</a></li> <li><a href="/wiki/Uvitonic_acid" title="Uvitonic acid">Uvitonic acid</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="Notes">Notes</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pyruvic_acid&action=edit&section=11" title="Edit section: Notes"><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-iupac2013-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-iupac2013_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-iupac2013_1-1"><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 class="citation book cs1"><i>Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book)</i>. 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D.; Boctor, N. Z.; Filley, T. R.; Hazen, R. M.; Scott, J. H.; Sharma, A.; Yoder, H. S. Jr (2000). "Primordial Carbonylated Iron-Sulfur Compounds and the Synthesis of Pyruvate". <i>Science</i>. <b>289</b> (5483): <span class="nowrap">1337–</span>1340. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2000Sci...289.1337C">2000Sci...289.1337C</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1126%2Fscience.289.5483.1337">10.1126/science.289.5483.1337</a>. <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/10958777">10958777</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:14911449">14911449</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Science&rft.atitle=Primordial+Carbonylated+Iron-Sulfur+Compounds+and+the+Synthesis+of+Pyruvate&rft.volume=289&rft.issue=5483&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1337-%3C%2Fspan%3E1340&rft.date=2000&rft_id=info%3Adoi%2F10.1126%2Fscience.289.5483.1337&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A14911449%23id-name%3DS2CID&rft_id=info%3Apmid%2F10958777&rft_id=info%3Abibcode%2F2000Sci...289.1337C&rft.aulast=Cody&rft.aufirst=G.+D.&rft.au=Boctor%2C+N.+Z.&rft.au=Filley%2C+T.+R.&rft.au=Hazen%2C+R.+M.&rft.au=Scott%2C+J.+H.&rft.au=Sharma%2C+A.&rft.au=Yoder%2C+H.+S.+Jr&rfr_id=info%3Asid%2Fen.wikipedia.org%3APyruvic+acid" class="Z3988"></span></li></ul> <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=Pyruvic_acid&action=edit&section=13" 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="http://gmd.mpimp-golm.mpg.de/Spectrums/24255dbc-f607-4bd7-aac1-fc17b3663b9e.aspx">Pyruvic acid mass spectrum</a></li></ul> <style data-mw-deduplicate="TemplateStyles:r1235681985">.mw-parser-output .side-box{margin:4px 0;box-sizing:border-box;border:1px solid #aaa;font-size:88%;line-height:1.25em;background-color:var(--background-color-interactive-subtle,#f8f9fa);display:flow-root}.mw-parser-output .side-box-abovebelow,.mw-parser-output .side-box-text{padding:0.25em 0.9em}.mw-parser-output .side-box-image{padding:2px 0 2px 0.9em;text-align:center}.mw-parser-output .side-box-imageright{padding:2px 0.9em 2px 0;text-align:center}@media(min-width:500px){.mw-parser-output .side-box-flex{display:flex;align-items:center}.mw-parser-output .side-box-text{flex:1;min-width:0}}@media(min-width:720px){.mw-parser-output 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flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:light-dark(lightgreen,darkgreen);"> <p style="margin: 0.1em 0.5em; color:var(--color-base)"><a href="/wiki/Glucose" title="Glucose">Glucose</a></p> </div><div style="margin: auto 0"><span class="skin-invert-image" 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:light-dark(#ffcccc,#6a331d);"> <p style="margin: 0.1em 0.5em; color:var(--color-base)"><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 class="skin-invert-image" 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:light-dark(lightgreen,darkgreen);"> <p style="margin: 0.1em 0.5em; color:var(--color-base)"><a href="/wiki/Glucose_6-phosphate" title="Glucose 6-phosphate">Glucose 6-phosphate</a></p> </div><div style="margin: auto 0"><span class="skin-invert-image" 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:light-dark(#ffcccc,#6a331d);"> <p style="margin: 0.1em 0.5em; color:var(--color-base)"><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 class="skin-invert-image" 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:light-dark(lightgreen,darkgreen);"> <p style="margin: 0.1em 0.5em; color:var(--color-base)"><a href="/wiki/Fructose_6-phosphate" title="Fructose 6-phosphate">Fructose 6-phosphate</a></p> </div><div style="margin: auto 0"><span class="skin-invert-image" 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:light-dark(#ffcccc,#6a331d);"> <p style="margin: 0.1em 0.5em; color:var(--color-base)"><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 class="skin-invert-image" 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:light-dark(lightgreen,darkgreen);"> <p style="margin: 0.1em 0.5em; color:var(--color-base)"><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 class="skin-invert-image" 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:light-dark(#ffcccc,#6a331d);"> <p style="margin: 0.1em 0.5em; color:var(--color-base)"><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 class="skin-invert-image" 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:light-dark(lightgreen,darkgreen);"> <p style="margin: 0.1em 0.5em; color:var(--color-base)"><a href="/wiki/Dihydroxyacetone_phosphate" title="Dihydroxyacetone phosphate">Dihydroxyacetone phosphate</a></p> </div><div style="margin: auto 0"><span class="skin-invert-image" 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; color:var(--color-base)">+</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:light-dark(lightgreen,darkgreen);"> <p style="margin: 0.1em 0.5em; color:var(--color-base)"><a href="/wiki/Glyceraldehyde_3-phosphate" title="Glyceraldehyde 3-phosphate">Glyceraldehyde 3-phosphate</a></p> </div><div style="margin: auto 0"><span class="skin-invert-image" 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:light-dark(#ffcccc,#6a331d);"> <p style="margin: 0.1em 0.5em; color:var(--color-base)"><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 class="skin-invert-image" 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:light-dark(lightgreen,darkgreen);"> <p style="margin: 0.1em 0.5em; color:var(--color-base)"><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 class="skin-invert-image" 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:light-dark(#ffcccc,#6a331d);"> <p style="margin: 0.1em 0.5em; color:var(--color-base)"><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 class="skin-invert-image" 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:light-dark(lightgreen,darkgreen);"> <p style="margin: 0.1em 0.5em; color:var(--color-base)"><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 class="skin-invert-image" 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:light-dark(#ffcccc,#6a331d);"> <p style="margin: 0.1em 0.5em; color:var(--color-base)"><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 class="skin-invert-image" 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:light-dark(lightgreen,darkgreen);"> <p style="margin: 0.1em 0.5em; color:var(--color-base)"><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 class="skin-invert-image" 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:light-dark(#ffcccc,#6a331d);"> <p style="margin: 0.1em 0.5em; color:var(--color-base)"><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 class="skin-invert-image" 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:light-dark(lightgreen,darkgreen);"> <p style="margin: 0.1em 0.5em; color:var(--color-base)"><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 class="skin-invert-image" 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:light-dark(#ffcccc,#6a331d);"> <p style="margin: 0.1em 0.5em; color:var(--color-base)"><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 class="skin-invert-image" 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:light-dark(lightgreen,darkgreen);"> <p style="margin: 0.1em 0.5em; color:var(--color-base)"><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 class="skin-invert-image" 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:light-dark(#ffcccc,#6a331d);"> <p style="margin: 0.1em 0.5em; color:var(--color-base)"><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 class="skin-invert-image" 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:light-dark(lightgreen,darkgreen);"> <p style="margin: 0.1em 0.5em; color:var(--color-base)"><strong>2 × </strong><a class="mw-selflink selflink">Pyruvate</a></p> </div><div style="margin: auto 0"><strong>2 × </strong> <span class="skin-invert-image" 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="Amino_acid_metabolism_metabolic_intermediates153" 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_intermediates153" 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 href="/wiki/Acetyl-CoA" title="Acetyl-CoA">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→31" 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:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><style data-mw-deduplicate="TemplateStyles:r1038841319">.mw-parser-output .tooltip-dotted{border-bottom:1px dotted;cursor:help}</style></div><div role="navigation" class="navbox authority-control" aria-label="Navbox864" style="padding:3px"><table class="nowraplinks hlist navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Help:Authority_control" title="Help:Authority control">Authority control databases</a>: National <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q213580#identifiers" title="Edit this at Wikidata"><img alt="Edit this at 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