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Available in 13 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-13" 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">13 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D9%87%DB%8C%D8%AF%D8%B1%D9%88%DA%A9%D8%B3%DB%8C_%D9%85%D8%AA%DB%8C%D9%84%D9%82%D9%84%D9%88%D8%AA%D8%A7%D8%B1%DB%8C%D9%84_%DA%A9%D9%88%D8%A2%D9%86%D8%B2%DB%8C%D9%88%D9%85_%D8%A2" title="هیدروکسی متیلقلوتاریل کوآنزیوم آ – South Azerbaijani" lang="azb" hreflang="azb" data-title="هیدروکسی متیلقلوتاریل کوآنزیوم آ" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/3-hidroxi-3-metilglutaril-coenzim_A" title="3-hidroxi-3-metilglutaril-coenzim A – Catalan" lang="ca" hreflang="ca" data-title="3-hidroxi-3-metilglutaril-coenzim A" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/HMG-CoA" title="HMG-CoA – Spanish" lang="es" hreflang="es" data-title="HMG-CoA" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%87%DB%8C%D8%AF%D8%B1%D9%88%DA%A9%D8%B3%DB%8C_%D9%85%D8%AA%DB%8C%D9%84%E2%80%8C%DA%AF%D9%84%D9%88%D8%AA%D8%A7%D8%B1%DB%8C%D9%84_%DA%A9%D9%88%D8%A2%D9%86%D8%B2%DB%8C%D9%85_%D8%A2" title="هیدروکسی متیل‌گلوتاریل کوآنزیم آ – Persian" lang="fa" hreflang="fa" data-title="هیدروکسی متیل‌گلوتاریل کوآنزیم آ" 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/3-Hydroxy-3-m%C3%A9thylglutaryl-coenzyme_A" title="3-Hydroxy-3-méthylglutaryl-coenzyme A – French" lang="fr" hreflang="fr" data-title="3-Hydroxy-3-méthylglutaryl-coenzyme A" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/3-hidroxi-3-metilglutaril-coencima_A" title="3-hidroxi-3-metilglutaril-coencima A – Galician" lang="gl" hreflang="gl" data-title="3-hidroxi-3-metilglutaril-coencima A" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EB%B2%A0%ED%83%80-%ED%95%98%EC%9D%B4%EB%93%9C%EB%A1%9D%EC%8B%9C_%EB%B2%A0%ED%83%80-%EB%A9%94%ED%8B%B8%EA%B8%80%EB%A3%A8%ED%83%80%EB%A6%B4-CoA" title="베타-하이드록시 베타-메틸글루타릴-CoA – Korean" lang="ko" hreflang="ko" data-title="베타-하이드록시 베타-메틸글루타릴-CoA" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/3-idrossi-3-metilglutaril-coenzima_A" title="3-idrossi-3-metilglutaril-coenzima A – Italian" lang="it" hreflang="it" data-title="3-idrossi-3-metilglutaril-coenzima A" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%92%E3%83%89%E3%83%AD%E3%82%AD%E3%82%B7%E3%83%A1%E3%83%81%E3%83%AB%E3%82%B0%E3%83%AB%E3%82%BF%E3%83%AA%E3%83%ABCoA" title="ヒドロキシメチルグルタリルCoA – Japanese" lang="ja" hreflang="ja" data-title="ヒドロキシメチルグルタリルCoA" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/3-Hydroksy-3-metyloglutarylokoenzym_A" title="3-Hydroksy-3-metyloglutarylokoenzym A – Polish" lang="pl" hreflang="pl" data-title="3-Hydroksy-3-metyloglutarylokoenzym A" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/HMG-KoA" title="HMG-KoA – Serbian" lang="sr" hreflang="sr" data-title="HMG-KoA" 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/HMG-KoA" title="HMG-KoA – Serbo-Croatian" lang="sh" hreflang="sh" data-title="HMG-KoA" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E7%BE%9F%E7%94%B2%E5%9F%BA%E6%88%8A%E4%BA%8C%E9%85%B8%E5%8D%95%E9%85%B0%E8%BE%85%E9%85%B6A" title="羟甲基戊二酸单酰辅酶A – Chinese" lang="zh" hreflang="zh" data-title="羟甲基戊二酸单酰辅酶A" data-language-autonym="中文" data-language-local-name="Chinese" 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</div> </div> </nav> </div> </div> </div> <div class="vector-column-end"> <div class="vector-sticky-pinned-container"> <nav class="vector-page-tools-landmark" aria-label="Page tools"> <div id="vector-page-tools-pinned-container" class="vector-pinned-container"> </div> </nav> <nav class="vector-appearance-landmark" aria-label="Appearance"> <div id="vector-appearance-pinned-container" class="vector-pinned-container"> <div id="vector-appearance" class="vector-appearance vector-pinnable-element"> <div class="vector-pinnable-header vector-appearance-pinnable-header vector-pinnable-header-pinned" data-feature-name="appearance-pinned" data-pinnable-element-id="vector-appearance" data-pinned-container-id="vector-appearance-pinned-container" data-unpinned-container-id="vector-appearance-unpinned-container" > <div class="vector-pinnable-header-label">Appearance</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" 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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>HMG-CoA </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center skin-invert" typeof="mw:File"><a href="/wiki/File:HMG_coenzyme_A.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bd/HMG_coenzyme_A.svg/330px-HMG_coenzyme_A.svg.png" decoding="async" width="300" height="107" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bd/HMG_coenzyme_A.svg/500px-HMG_coenzyme_A.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bd/HMG_coenzyme_A.svg/960px-HMG_coenzyme_A.svg.png 2x" data-file-width="985" data-file-height="350" /></a><figcaption></figcaption></figure> </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/Chemical_nomenclature" title="Chemical nomenclature">IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">(9R,21S)-1-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl]-3,5,9,21-tetrahydroxy-8,8,21-trimethyl-10,14,19-trioxo-2,4,6-trioxa-18-thia-11,15-diaza-3,5-diphosphatricosan-23-oic acid 3,5-dioxide</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;">3-hydroxy-3-methylglutaryl CoA; 3-hydroxy-3-methylglutaryl coenzyme A</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=1553-55-5">1553-55-5</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%28O%29C%5BC%40%40%5D%28O%29%28C%29CC%28%3DO%29SCCNC%28%3DO%29CCNC%28%3DO%29%5BC%40H%5D%28O%29C%28C%29%28C%29COP%28%3DO%29%28O%29OP%28%3DO%29%28O%29OC%5BC%40H%5D3O%5BC%40%40H%5D%28n2cnc1c%28ncnc12%29N%29%5BC%40H%5D%28O%29%5BC%40%40H%5D3OP%28%3DO%29%28O%29O">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=61659">CHEBI:61659</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.392859.html">392859</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/100.014.820">100.014.820</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q307532#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=3040">3040</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Medical_Subject_Headings" title="Medical Subject Headings">MeSH</a> </td> <td><span title="www.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://www.nlm.nih.gov/cgi/mesh/2014/MB_cgi?mode=&term=HMG-CoA">HMG-CoA</a></span> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/445127">445127</a></span></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/DTXSID00935181,">DTXSID40862689 DTXSID00935181, DTXSID40862689</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q307532#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/C27H44N7O20P3S/c1-26(2,21(40)24(41)30-5-4-15(35)29-6-7-58-17(38)9-27(3,42)8-16(36)37)11-51-57(48,49)54-56(46,47)50-10-14-20(53-55(43,44)45)19(39)25(52-14)34-13-33-18-22(28)31-12-32-23(18)34/h12-14,19-21,25,39-40,42H,4-11H2,1-3H3,(H,29,35)(H,30,41)(H,36,37)(H,46,47)(H,48,49)(H2,28,31,32)(H2,43,44,45)/t14-,19-,20-,21+,25-,27+/m1/s1<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: CABVTRNMFUVUDM-VRHQGPGLSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/C27H44N7O20P3S/c1-26(2,21(40)24(41)30-5-4-15(35)29-6-7-58-17(38)9-27(3,42)8-16(36)37)11-51-57(48,49)54-56(46,47)50-10-14-20(53-55(43,44)45)19(39)25(52-14)34-13-33-18-22(28)31-12-32-23(18)34/h12-14,19-21,25,39-40,42H,4-11H2,1-3H3,(H,29,35)(H,30,41)(H,36,37)(H,46,47)(H,48,49)(H2,28,31,32)(H2,43,44,45)/t14-,19-,20-,21+,25-,27+/m1/s1</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: CABVTRNMFUVUDM-VRHQGPGLBX</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(O)C[C@@](O)(C)CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@H]3O[C@@H](n2cnc1c(ncnc12)N)[C@H](O)[C@@H]3OP(=O)(O)O</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>27</sub>H<sub>44</sub>N<sub>7</sub>O<sub>20</sub>P<sub>3</sub>S  </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td>911.661 g/mol    </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="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/12px-Yes_check.svg.png" decoding="async" width="12" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/18px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/24px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=450656813&page2=HMG-CoA">verify</a></span> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <sup><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup> ?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>β-Hydroxy β-methylglutaryl-CoA</b> (<b>HMG-CoA</b>), also known as <b>3-hydroxy-3-methylglutaryl coenzyme A</b>, is an intermediate in the <a href="/wiki/Mevalonate_pathway" title="Mevalonate pathway">mevalonate</a> and <a href="/wiki/Ketogenesis" title="Ketogenesis">ketogenesis</a> pathways. It is formed from <a href="/wiki/Acetyl_CoA" class="mw-redirect" title="Acetyl CoA">acetyl CoA</a> and <a href="/wiki/Acetoacetyl_CoA" class="mw-redirect" title="Acetoacetyl CoA">acetoacetyl CoA</a> by <a href="/wiki/HMG-CoA_synthase" class="mw-redirect" title="HMG-CoA synthase">HMG-CoA synthase</a>. The research of <a href="/wiki/Minor_J._Coon" title="Minor J. Coon">Minor J. Coon</a> and <a href="/wiki/Bimal_Kumar_Bachhawat" title="Bimal Kumar Bachhawat">Bimal Kumar Bachhawat</a> in the 1950s at <a href="/wiki/University_of_Illinois" class="mw-redirect" title="University of Illinois">University of Illinois</a> led to its discovery.<sup id="cite_ref-Classics_in_Indian_Medicine_1-0" class="reference"><a href="#cite_note-Classics_in_Indian_Medicine-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-An_outstanding_scientist_and_a_splendid_human_being_2-0" class="reference"><a href="#cite_note-An_outstanding_scientist_and_a_splendid_human_being-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p>HMG-CoA is a <a href="/wiki/Metabolic_intermediate" title="Metabolic intermediate">metabolic intermediate</a> in the <a href="/wiki/Metabolism" title="Metabolism">metabolism</a> of the <a href="/wiki/Branched-chain_amino_acid" title="Branched-chain amino acid">branched-chain amino acids</a>, which include <a href="/wiki/Leucine" title="Leucine">leucine</a>, <a href="/wiki/Isoleucine" title="Isoleucine">isoleucine</a>, and <a href="/wiki/Valine" title="Valine">valine</a>.<sup id="cite_ref-HMG_biosynthesis_3-0" class="reference"><a href="#cite_note-HMG_biosynthesis-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Its immediate precursors are <a href="/wiki/%CE%92-methylglutaconyl-CoA" class="mw-redirect" title="Β-methylglutaconyl-CoA">β-methylglutaconyl-CoA</a> (MG-CoA) and <a href="/wiki/%CE%92-hydroxy_%CE%B2-methylbutyryl-CoA" class="mw-redirect" title="Β-hydroxy β-methylbutyryl-CoA">β-hydroxy β-methylbutyryl-CoA</a> (HMB-CoA).<sup id="cite_ref-ISSN_position_stand_2013_4-0" class="reference"><a href="#cite_note-ISSN_position_stand_2013-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-HMB_athletic_performance-related_effects_2011_review_5-0" class="reference"><a href="#cite_note-HMB_athletic_performance-related_effects_2011_review-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Leucine_metabolism_6-0" class="reference"><a href="#cite_note-Leucine_metabolism-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/HMG-CoA_reductase" title="HMG-CoA reductase">HMG-CoA reductase</a> catalyzes the conversion of HMG-CoA to <a href="/wiki/Mevalonic_acid" title="Mevalonic acid">mevalonic acid</a>, a necessary step in the biosynthesis of cholesterol. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Biosynthesis">Biosynthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=HMG-CoA&action=edit&section=1" title="Edit section: Biosynthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="skin-invert-image"> <table role="presentation" cellpadding="0" style="border-spacing:0; margin-left: auto; margin-right: auto; border: none;"> <tbody><tr> <td><div class="thumb center" style="margin: 1em auto;"> <div class="thumbinner" style="width:602px;"> <div style="clear: both; font-weight: bold; font-size: 106.4%; text-align: center; background-color: light-dark(#F0F8FF,var(--background-color-neutral)); color:var(--color-base,light-dark(#202122,#eaecf0)); margin-bottom:3px;"><a href="/wiki/Leucine#Metabolism_in_humans" title="Leucine">Leucine metabolism in humans</a></div> <div class="skin-invert-image" style="position:relative; width:600px; height:436px; overflow:hidden; border:solid #ccc 1px; background-color:light-dark(white,transparent);"> <div style="left:0px; top:0px; width:600px; position:absolute"> <span typeof="mw:File"><a href="https://commons.wikimedia.org/wiki/File:HMB_biosynthesis_and_metabolism_diagram_-_no_labels.svg" title="commons:File:HMB biosynthesis and metabolism diagram - no labels.svg"><img alt="Diagram of leucine, HMB, and isovaleryl-CoA metabolism in humans" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/03/HMB_biosynthesis_and_metabolism_diagram_-_no_labels.svg/600px-HMB_biosynthesis_and_metabolism_diagram_-_no_labels.svg.png" decoding="async" width="600" height="436" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/03/HMB_biosynthesis_and_metabolism_diagram_-_no_labels.svg/900px-HMB_biosynthesis_and_metabolism_diagram_-_no_labels.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/03/HMB_biosynthesis_and_metabolism_diagram_-_no_labels.svg/1200px-HMB_biosynthesis_and_metabolism_diagram_-_no_labels.svg.png 2x" data-file-width="2126" data-file-height="1545" /></a></span> </div> <div style="text-align:center; font-size:12px; line-height:110%"> <div style="background-color:transparent; color:var(--color-base,#202122)"><div id="annotation_180x2" style="position:absolute; left:180px; top:2px; font-size:18px; font-size:18; line-height:20px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Leucine" title="Leucine"><span class="nowrap"><span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>-Leucine</span></a></span></div> <div id="annotation_96x37" style="position:absolute; left:96px; top:37px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Branched-chain_amino_acid_aminotransferase" title="Branched-chain amino acid aminotransferase">Branched-chain amino<br />acid aminotransferase</a></span></div> <div id="annotation_240x30" style="position:absolute; left:240px; top:30px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/%CE%91-Ketoglutarate" class="mw-redirect" title="Α-Ketoglutarate">α-Ketoglutarate</a></span></div> <div id="annotation_243x61" style="position:absolute; left:243px; top:61px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Glutamate" class="mw-redirect" title="Glutamate">Glutamate</a></span></div> <div id="annotation_466x75" style="position:absolute; left:466px; top:75px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Glutamate" class="mw-redirect" title="Glutamate">Glutamate</a></span></div> <div id="annotation_383x30" style="position:absolute; left:383px; top:30px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Alanine" title="Alanine">Alanine</a></span></div> <div id="annotation_383x62" style="position:absolute; left:383px; top:62px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Pyruvate" class="mw-redirect" title="Pyruvate">Pyruvate</a></span></div> <div id="annotation_75x85" style="position:absolute; left:75px; top:85px; font-size:15px; font-size:15; line-height:17px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Skeletal_muscle" title="Skeletal muscle">Muscle</a>: <a href="/wiki/Alpha-Ketoisocaproic_acid" class="mw-redirect" title="Alpha-Ketoisocaproic acid">α-Ketoisocaproate</a> (α-KIC)</span></div> <div id="annotation_82x128" style="position:absolute; left:82px; top:128px; font-size:15px; font-size:15; line-height:17px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Liver" title="Liver">Liver</a>: <a href="/wiki/Alpha-Ketoisocaproic_acid" class="mw-redirect" title="Alpha-Ketoisocaproic acid">α-Ketoisocaproate</a> (α-KIC)</span></div> <div id="annotation_300x106" style="position:absolute; left:300px; top:106px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Branched-chain_%CE%B1-ketoacid_dehydrogenase" class="mw-redirect" title="Branched-chain α-ketoacid dehydrogenase">Branched-chain α-ketoacid<br />dehydrogenase</a> (<a href="/wiki/Mitochondria" class="mw-redirect" title="Mitochondria">mitochondria</a>)</span></div> <div id="annotation_93x156" style="position:absolute; left:93px; top:156px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/4-Hydroxyphenylpyruvate_dioxygenase" title="4-Hydroxyphenylpyruvate dioxygenase">KIC-dioxygenase</a><br />(<a href="/wiki/Cytosol" title="Cytosol">cytosol</a>)</span></div> <div id="annotation_465x126" style="position:absolute; left:465px; top:126px; font-size:15px; font-size:15; line-height:17px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Isovaleryl-CoA" title="Isovaleryl-CoA">Isovaleryl-CoA</a></span></div> <div id="annotation_85x198" style="position:absolute; left:85px; top:198px; font-size:15px; font-size:15; line-height:17px;"><span style="background-color:; color:inherit;"><a href="/wiki/%CE%92-Hydroxy_%CE%B2-methylbutyric_acid" title="Β-Hydroxy β-methylbutyric acid"><b>β-Hydroxy<br />β-methylbutyrate</b></a><br />(<b>HMB</b>)</span></div> <div id="annotation_2x205" style="position:absolute; left:2px; top:205px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Excretion" title="Excretion">Excreted</a><br />in urine<br />(10–40%)</span></div> <p><br /> </p> <div id="annotation_239x217" style="position:absolute; left:239px; top:217px; font-size:13px; font-size:13; line-height:15px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Beta-Hydroxy_beta-methylbutyryl-CoA" class="mw-redirect" title="Beta-Hydroxy beta-methylbutyryl-CoA">HMB-CoA</a></span></div> <div id="annotation_175x269" style="position:absolute; left:175px; top:269px; font-size:13px; font-size:13; line-height:15px;"><span style="background-color:transparent; color:inherit;">β-Hydroxy β-methylglutaryl-CoA<br />(<span style="color:black;background:yellow"><b>HMG-CoA</b></span>)</span></div> <div id="annotation_445x208" style="position:absolute; left:445px; top:208px; font-size:13px; font-size:13; line-height:15px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Methylcrotonyl-CoA" title="Methylcrotonyl-CoA">β-Methylcrotonyl-CoA</a><br />(MC-CoA)</span></div> <div id="annotation_442x269" style="position:absolute; left:442px; top:269px; font-size:13px; font-size:13; line-height:15px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/3-Methylglutaconyl-CoA" title="3-Methylglutaconyl-CoA">β-Methylglutaconyl-CoA</a><br />(MG-CoA)</span></div> <div id="annotation_395x148" style="position:absolute; left:395px; top:148px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Carbon_dioxide" title="Carbon dioxide">CO<sub>2</sub></a></span></div> <div id="annotation_221x246" style="position:absolute; left:221px; top:246px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Carbon_dioxide" title="Carbon dioxide">CO<sub>2</sub></a></span></div> <div id="annotation_214x163" style="position:absolute; left:214px; top:163px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Oxygen" title="Oxygen">O<sub>2</sub></a></span></div> <div id="annotation_211x186" style="position:absolute; left:211px; top:186px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Carbon_dioxide" title="Carbon dioxide">CO<sub>2</sub></a></span></div> <div id="annotation_426x239" style="position:absolute; left:426px; top:239px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Properties_of_water" title="Properties of water">H<sub>2</sub>O</a></span></div> <div id="annotation_458x246" style="position:absolute; left:458px; top:246px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Carbon_dioxide" title="Carbon dioxide">CO<sub>2</sub></a></span></div> <div id="annotation_422x297" style="position:absolute; left:422px; top:297px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Properties_of_water" title="Properties of water">H<sub>2</sub>O</a></span></div> <div id="annotation_242x316" style="position:absolute; left:242px; top:316px; line-height:110%;"><span style="background-color:transparent; color:inherit;">(<a href="/wiki/Liver" title="Liver">liver</a>)<br /><a href="/wiki/HMG-CoA_lyase" class="mw-redirect" title="HMG-CoA lyase">HMG-CoA<br />lyase</a></span></div> <div id="annotation_314x208" style="position:absolute; left:314px; top:208px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Enoyl-CoA_hydratase" title="Enoyl-CoA hydratase">Enoyl-CoA hydratase</a></span></div> <div id="annotation_511x163" style="position:absolute; left:511px; top:163px; font-size:12px; font-size:12; line-height:14px; text-align:left;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Isovaleryl-CoA_dehydrogenase" title="Isovaleryl-CoA dehydrogenase">Isovaleryl-CoA<br />dehydrogenase</a></span></div> <div id="annotation_511x238" style="position:absolute; left:511px; top:238px; font-size:12px; font-size:12; line-height:14px; text-align:left;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Methylcrotonyl-CoA_carboxylase" title="Methylcrotonyl-CoA carboxylase">MC-CoA<br />carboxylase</a></span></div> <div id="annotation_376x254" style="position:absolute; left:376px; top:254px; font-size:12px; font-size:12; line-height:14px; text-align:center;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Methylglutaconyl-CoA_hydratase" title="Methylglutaconyl-CoA hydratase">MG-CoA<br />hydratase</a></span></div> <div id="annotation_59x316" style="position:absolute; left:59px; top:316px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/HMG-CoA_reductase" title="HMG-CoA reductase">HMG-CoA<br />reductase</a></span></div> <div id="annotation_410x331" style="position:absolute; left:410px; top:331px; font-size:12px; font-size:12; line-height:14px; text-align:right;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/HMG-CoA_synthase" class="mw-redirect" title="HMG-CoA synthase">HMG-CoA <br />synthase</a></span></div> <div id="annotation_205x387" style="position:absolute; left:205px; top:387px; font-size:12px; font-size:12; line-height:14px; text-align:left;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/3-Hydroxybutyrate_dehydrogenase" title="3-Hydroxybutyrate dehydrogenase">β-Hydroxybutyrate<br />dehydrogenase</a></span></div> <div id="annotation_80x385" style="position:absolute; left:80px; top:385px; font-size:12px; font-size:12; line-height:14px; text-align:left;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/File:Mevalonate_pathway.svg" title="File:Mevalonate pathway.svg">Mevalonate<br />pathway</a></span></div> <div id="annotation_389x385" style="position:absolute; left:389px; top:385px; font-size:12px; font-size:12; line-height:14px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Thiolase" title="Thiolase">Thiolase</a></span></div> <div id="annotation_274x236" style="position:absolute; left:274px; top:236px; font-size:12px; font-size:12; line-height:14px; text-align:left;"><span style="background-color:transparent; color:inherit;">Unknown<br />enzyme</span></div> <div id="annotation_152x420" style="position:absolute; left:152px; top:420px; font-size:13px; font-size:13; line-height:15px;"><span style="background-color:; color:inherit;"><a href="/wiki/Beta-Hydroxybutyric_acid" class="mw-redirect" title="Beta-Hydroxybutyric acid">β-Hydroxybutyrate</a></span></div> <div id="annotation_432x395" style="position:absolute; left:432px; top:395px; font-size:13px; font-size:13; line-height:15px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Acetoacetyl-CoA" title="Acetoacetyl-CoA">Acetoacetyl-CoA</a></span></div> <div id="annotation_328x395" style="position:absolute; left:328px; top:395px; font-size:13px; font-size:13; line-height:15px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Acetyl-CoA" title="Acetyl-CoA">Acetyl-CoA</a></span></div> <div id="annotation_164x365" style="position:absolute; left:164px; top:365px; font-size:13px; font-size:13; line-height:15px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Acetoacetate" class="mw-redirect" title="Acetoacetate">Acetoacetate</a></span></div> <div id="annotation_44x365" style="position:absolute; left:44px; top:365px; font-size:13px; font-size:13; line-height:15px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Mevalonate" class="mw-redirect" title="Mevalonate">Mevalonate</a></span></div> <div id="annotation_43x420" style="position:absolute; left:43px; top:420px; font-size:13px; font-size:13; line-height:15px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a></span></div></div> </div> </div> <div class="thumbcaption" style="clear:left"><div style="float:left;margin-right:0.5em"><span typeof="mw:File"><span title="The image above contains clickable links"><img alt="The image above contains clickable links" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/20px-Interactive_icon.svg.png" decoding="async" width="18" height="27" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/40px-Interactive_icon.svg.png 1.5x" data-file-width="133" data-file-height="200" /></span></span></div>Human <a href="/wiki/Metabolic_pathway" title="Metabolic pathway">metabolic pathway</a> for <a href="/wiki/%CE%92-Hydroxy_%CE%B2-methylbutyric_acid" title="Β-Hydroxy β-methylbutyric acid">HMB</a> and <a href="/wiki/Isovaleryl-CoA" title="Isovaleryl-CoA">isovaleryl-CoA</a> relative to <a href="/wiki/Leucine" title="Leucine"><span class="nowrap"><span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>-leucine</span></a>.<sup id="cite_ref-ISSN_position_stand_2013_4-1" class="reference"><a href="#cite_note-ISSN_position_stand_2013-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-HMB_athletic_performance-related_effects_2011_reviewb_7-0" class="reference"><a href="#cite_note-HMB_athletic_performance-related_effects_2011_reviewb-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Leucine_metabolism_6-1" class="reference"><a href="#cite_note-Leucine_metabolism-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Of the two major pathways, <span class="nowrap"><span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>-leucine</span> is mostly metabolized into isovaleryl-CoA, while only about 5% is metabolized into HMB.<sup id="cite_ref-ISSN_position_stand_2013_4-2" class="reference"><a href="#cite_note-ISSN_position_stand_2013-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-HMB_athletic_performance-related_effects_2011_reviewb_7-1" class="reference"><a href="#cite_note-HMB_athletic_performance-related_effects_2011_reviewb-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Leucine_metabolism_6-2" class="reference"><a href="#cite_note-Leucine_metabolism-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup></div> </div> </div> </td></tr></tbody></table> </div> <p><br /> </p> <div class="mw-heading mw-heading2"><h2 id="Mevalonate_pathway">Mevalonate pathway</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=HMG-CoA&action=edit&section=2" title="Edit section: Mevalonate pathway"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Mevalonate_pathway" title="Mevalonate pathway">Mevalonate pathway</a></div> <p><a href="/wiki/Mevalonate" class="mw-redirect" title="Mevalonate">Mevalonate</a> synthesis begins with the <a href="/wiki/Beta-ketothiolase" class="mw-redirect" title="Beta-ketothiolase">beta-ketothiolase</a>-catalyzed <a href="/wiki/Claisen_condensation" title="Claisen condensation">Claisen condensation</a> of two molecules of <a href="/wiki/Acetyl-CoA" title="Acetyl-CoA">acetyl-CoA</a> to produce <a href="/wiki/Acetoacetyl-CoA" title="Acetoacetyl-CoA">acetoacetyl CoA</a>. The following reaction involves the joining of <a href="/wiki/Acetyl-CoA" title="Acetyl-CoA">acetyl-CoA</a> and <a href="/wiki/Acetoacetyl-CoA" title="Acetoacetyl-CoA">acetoacetyl-CoA</a> to form HMG-CoA, a process catalyzed by <a href="/wiki/HMG-CoA_synthase" class="mw-redirect" title="HMG-CoA synthase">HMG-CoA synthase</a>.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p><p>In the final step of <a href="/wiki/Mevalonate" class="mw-redirect" title="Mevalonate">mevalonate</a> biosynthesis, <a href="/wiki/HMG-CoA_reductase" title="HMG-CoA reductase">HMG-CoA reductase</a>, an <a href="/wiki/NADPH" class="mw-redirect" title="NADPH">NADPH</a>-dependent <a href="/wiki/Oxidoreductase" title="Oxidoreductase">oxidoreductase</a>, catalyzes the conversion of HMG-CoA into <a href="/wiki/Mevalonate" class="mw-redirect" title="Mevalonate">mevalonate</a>, which is the primary regulatory point in this pathway. <a href="/wiki/Mevalonate" class="mw-redirect" title="Mevalonate">Mevalonate</a> serves as the precursor to <a href="/wiki/Isoprenoid" class="mw-redirect" title="Isoprenoid">isoprenoid</a> groups that are incorporated into a wide variety of end-products, including <a href="/wiki/Cholesterol" title="Cholesterol">cholesterol</a> in humans.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-left skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Mevalonate_pathway.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b4/Mevalonate_pathway.svg/350px-Mevalonate_pathway.svg.png" decoding="async" width="350" height="495" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b4/Mevalonate_pathway.svg/525px-Mevalonate_pathway.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b4/Mevalonate_pathway.svg/700px-Mevalonate_pathway.svg.png 2x" data-file-width="744" data-file-height="1052" /></a><figcaption>Mevalonate pathway</figcaption></figure> <div style="clear:both;" class=""></div> <div class="mw-heading mw-heading2"><h2 id="Ketogenesis_pathway">Ketogenesis pathway</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=HMG-CoA&action=edit&section=3" title="Edit section: Ketogenesis pathway"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/HMG-CoA_lyase" class="mw-redirect" title="HMG-CoA lyase">HMG-CoA lyase</a> breaks it into <a href="/wiki/Acetyl_CoA" class="mw-redirect" title="Acetyl CoA">acetyl CoA</a> and <a href="/wiki/Acetoacetate" class="mw-redirect" title="Acetoacetate">acetoacetate</a>. </p> <figure class="mw-halign-left skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Ketogenesis.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Ketogenesis.svg/350px-Ketogenesis.svg.png" decoding="async" width="350" height="495" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Ketogenesis.svg/525px-Ketogenesis.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Ketogenesis.svg/700px-Ketogenesis.svg.png 2x" data-file-width="744" data-file-height="1052" /></a><figcaption><a href="/wiki/Ketogenesis" title="Ketogenesis">Ketogenesis</a></figcaption></figure> <div style="clear:both;" class=""></div> <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=HMG-CoA&action=edit&section=4" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Steroidogenic_enzyme" title="Steroidogenic enzyme">Steroidogenic enzyme</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=HMG-CoA&action=edit&section=5" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-Classics_in_Indian_Medicine-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-Classics_in_Indian_Medicine_1-0">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFSarkar2015" class="citation journal cs1">Sarkar DP (2015). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20160531082638/http://www.nmji.in/archives/Volume-28/Issue-3/Classics-in-Indian-Medicine.pdf">"Classics in Indian Medicine"</a> <span class="cs1-format">(PDF)</span>. <i>The National Medical Journal of India</i> (28): 3. Archived from <a rel="nofollow" class="external text" href="http://www.nmji.in/archives/Volume-28/Issue-3/Classics-in-Indian-Medicine.pdf">the original</a> <span class="cs1-format">(PDF)</span> on 2016-05-31.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+National+Medical+Journal+of+India&rft.atitle=Classics+in+Indian+Medicine&rft.issue=28&rft.pages=3&rft.date=2015&rft.aulast=Sarkar&rft.aufirst=Debi+P.&rft_id=http%3A%2F%2Fwww.nmji.in%2Farchives%2FVolume-28%2FIssue-3%2FClassics-in-Indian-Medicine.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHMG-CoA" class="Z3988"></span></span> </li> <li id="cite_note-An_outstanding_scientist_and_a_splendid_human_being-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-An_outstanding_scientist_and_a_splendid_human_being_2-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSurolia1997" class="citation journal cs1"><a href="/wiki/Avadhesha_Surolia" title="Avadhesha Surolia">Surolia A</a> (1997). <a rel="nofollow" class="external text" href="https://doi.org/10.1093%2Fglycob%2F7.4.453">"An outstanding scientist and a splendid human being"</a>. <i>Glycobiology</i>. <b>7</b> (4): <span class="nowrap">v–</span>ix. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1093%2Fglycob%2F7.4.453">10.1093/glycob/7.4.453</a></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Glycobiology&rft.atitle=An+outstanding+scientist+and+a+splendid+human+being&rft.volume=7&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3Ev-%3C%2Fspan%3Eix&rft.date=1997&rft_id=info%3Adoi%2F10.1093%2Fglycob%2F7.4.453&rft.aulast=Surolia&rft.aufirst=Avadhesha&rft_id=https%3A%2F%2Fdoi.org%2F10.1093%252Fglycob%252F7.4.453&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHMG-CoA" class="Z3988"></span></span> </li> <li id="cite_note-HMG_biosynthesis-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-HMG_biosynthesis_3-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.genome.jp/kegg-bin/show_pathway?map00280+C00356">"Valine, leucine and isoleucine degradation - Reference pathway"</a>. <i>Kyoto Encyclopedia of Genes and Genomes</i>. Kanehisa Laboratories. 27 January 2016<span class="reference-accessdate">. Retrieved <span class="nowrap">1 February</span> 2018</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Kyoto+Encyclopedia+of+Genes+and+Genomes&rft.atitle=Valine%2C+leucine+and+isoleucine+degradation+-+Reference+pathway&rft.date=2016-01-27&rft_id=http%3A%2F%2Fwww.genome.jp%2Fkegg-bin%2Fshow_pathway%3Fmap00280%2BC00356&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHMG-CoA" class="Z3988"></span></span> </li> <li id="cite_note-ISSN_position_stand_2013-4"><span class="mw-cite-backlink">^ <a href="#cite_ref-ISSN_position_stand_2013_4-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-ISSN_position_stand_2013_4-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-ISSN_position_stand_2013_4-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWilsonFitschenCampbellWilson2013" class="citation journal cs1">Wilson JM, Fitschen PJ, Campbell B, Wilson GJ, Zanchi N, Taylor L, Wilborn C, Kalman DS, Stout JR, Hoffman JR, Ziegenfuss TN, Lopez HL, Kreider RB, Smith-Ryan AE, Antonio J (February 2013). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3568064">"International Society of Sports Nutrition Position Stand: beta-hydroxy-beta-methylbutyrate (HMB)"</a>. <i>Journal of the International Society of Sports Nutrition</i>. <b>10</b> (1): 6. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1186%2F1550-2783-10-6">10.1186/1550-2783-10-6</a></span>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3568064">3568064</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/23374455">23374455</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+the+International+Society+of+Sports+Nutrition&rft.atitle=International+Society+of+Sports+Nutrition+Position+Stand%3A+beta-hydroxy-beta-methylbutyrate+%28HMB%29&rft.volume=10&rft.issue=1&rft.pages=6&rft.date=2013-02&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3568064%23id-name%3DPMC&rft_id=info%3Apmid%2F23374455&rft_id=info%3Adoi%2F10.1186%2F1550-2783-10-6&rft.aulast=Wilson&rft.aufirst=JM&rft.au=Fitschen%2C+PJ&rft.au=Campbell%2C+B&rft.au=Wilson%2C+GJ&rft.au=Zanchi%2C+N&rft.au=Taylor%2C+L&rft.au=Wilborn%2C+C&rft.au=Kalman%2C+DS&rft.au=Stout%2C+JR&rft.au=Hoffman%2C+JR&rft.au=Ziegenfuss%2C+TN&rft.au=Lopez%2C+HL&rft.au=Kreider%2C+RB&rft.au=Smith-Ryan%2C+AE&rft.au=Antonio%2C+J&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3568064&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHMG-CoA" class="Z3988"></span></span> </li> <li id="cite_note-HMB_athletic_performance-related_effects_2011_review-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-HMB_athletic_performance-related_effects_2011_review_5-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFZanchiGerlinger-RomeroGuimarães-Ferreirade_Siqueira_Filho2011" class="citation journal cs1">Zanchi NE, Gerlinger-Romero F, Guimarães-Ferreira L, de Siqueira Filho MA, Felitti V, Lira FS, Seelaender M, Lancha AH (April 2011). <a rel="nofollow" class="external text" href="https://repositorio.unal.edu.co/handle/unal/77957">"HMB supplementation: clinical and athletic performance-related effects and mechanisms of action"</a>. <i>Amino Acids</i>. <b>40</b> (4): <span class="nowrap">1015–</span>1025. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2Fs00726-010-0678-0">10.1007/s00726-010-0678-0</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/20607321">20607321</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:11120110">11120110</a>. <q>HMB is a metabolite of the amino acid leucine (Van Koverin and Nissen 1992), an essential amino acid. The first step in HMB metabolism is the reversible transamination of leucine to [α-KIC] that occurs mainly extrahepatically (Block and Buse 1990). Following this enzymatic reaction, [α-KIC] may follow one of two pathways. In the first, HMB is produced from [α-KIC] by the cytosolic enzyme KIC dioxygenase (Sabourin and Bieber 1983). The cytosolic dioxygenase has been characterized extensively and differs from the mitochondrial form in that the dioxygenase enzyme is a cytosolic enzyme, whereas the dehydrogenase enzyme is found exclusively in the mitochondrion (Sabourin and Bieber 1981, 1983). Importantly, this route of HMB formation is direct and completely dependent of liver KIC dioxygenase. Following this pathway, HMB in the cytosol is first converted to cytosolic β-hydroxy-β-methylglutaryl-CoA (HMG-CoA), which can then be directed for cholesterol synthesis (Rudney 1957) (Fig. 1). In fact, numerous biochemical studies have shown that HMB is a precursor of cholesterol (Zabin and Bloch 1951; Nissen et al. 2000).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Amino+Acids&rft.atitle=HMB+supplementation%3A+clinical+and+athletic+performance-related+effects+and+mechanisms+of+action&rft.volume=40&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1015-%3C%2Fspan%3E1025&rft.date=2011-04&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A11120110%23id-name%3DS2CID&rft_id=info%3Apmid%2F20607321&rft_id=info%3Adoi%2F10.1007%2Fs00726-010-0678-0&rft.aulast=Zanchi&rft.aufirst=NE&rft.au=Gerlinger-Romero%2C+F&rft.au=Guimar%C3%A3es-Ferreira%2C+L&rft.au=de+Siqueira+Filho%2C+MA&rft.au=Felitti%2C+V&rft.au=Lira%2C+FS&rft.au=Seelaender%2C+M&rft.au=Lancha%2C+AH&rft_id=https%3A%2F%2Frepositorio.unal.edu.co%2Fhandle%2Funal%2F77957&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHMG-CoA" class="Z3988"></span></span> </li> <li id="cite_note-Leucine_metabolism-6"><span class="mw-cite-backlink">^ <a href="#cite_ref-Leucine_metabolism_6-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Leucine_metabolism_6-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Leucine_metabolism_6-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKohlmeier2015" class="citation book cs1">Kohlmeier M (May 2015). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=aTQTAAAAQBAJ&q=beta-hydroxy%20beta-methylbutyrate%20HMB&pg=PA387">"Leucine"</a>. <a rel="nofollow" class="external text" href="https://books.google.com/books?id=aTQTAAAAQBAJ"><i>Nutrient Metabolism: Structures, Functions, and Genes</i></a> (2nd ed.). Academic Press. pp. <span class="nowrap">385–</span>388. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-12-387784-0" title="Special:BookSources/978-0-12-387784-0"><bdi>978-0-12-387784-0</bdi></a><span class="reference-accessdate">. Retrieved <span class="nowrap">6 June</span> 2016</span>. <q>Energy fuel: Eventually, most Leu is broken down, providing about 6.0kcal/g. About 60% of ingested Leu is oxidized within a few hours ... Ketogenesis: A significant proportion (40% of an ingested dose) is converted into acetyl-CoA and thereby contributes to the synthesis of ketones, steroids, fatty acids, and other compounds</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Leucine&rft.btitle=Nutrient+Metabolism%3A+Structures%2C+Functions%2C+and+Genes&rft.pages=%3Cspan+class%3D%22nowrap%22%3E385-%3C%2Fspan%3E388&rft.edition=2nd&rft.pub=Academic+Press&rft.date=2015-05&rft.isbn=978-0-12-387784-0&rft.aulast=Kohlmeier&rft.aufirst=M&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DaTQTAAAAQBAJ%26q%3Dbeta-hydroxy%2520beta-methylbutyrate%2520HMB%26pg%3DPA387&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHMG-CoA" class="Z3988"></span><br /><a rel="nofollow" class="external text" href="https://books.google.com/books?id=aTQTAAAAQBAJ&pg=PA386#v=onepage&q&f=false">Figure 8.57: Metabolism of <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>-leucine</a></span> </li> <li id="cite_note-HMB_athletic_performance-related_effects_2011_reviewb-7"><span class="mw-cite-backlink">^ <a href="#cite_ref-HMB_athletic_performance-related_effects_2011_reviewb_7-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-HMB_athletic_performance-related_effects_2011_reviewb_7-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFZanchiGerlinger-RomeroGuimarães-Ferreirade_Siqueira_Filho2011" class="citation journal cs1">Zanchi NE, Gerlinger-Romero F, Guimarães-Ferreira L, de Siqueira Filho MA, Felitti V, Lira FS, Seelaender M, Lancha AH (April 2011). <a rel="nofollow" class="external text" href="https://repositorio.unal.edu.co/handle/unal/77957">"HMB supplementation: clinical and athletic performance-related effects and mechanisms of action"</a>. <i>Amino Acids</i>. <b>40</b> (4): <span class="nowrap">1015–</span>1025. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2Fs00726-010-0678-0">10.1007/s00726-010-0678-0</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/20607321">20607321</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:11120110">11120110</a>. <q>HMB is a metabolite of the amino acid leucine (Van Koverin and Nissen 1992), an essential amino acid. The first step in HMB metabolism is the reversible transamination of leucine to [α-KIC] that occurs mainly extrahepatically (Block and Buse 1990). Following this enzymatic reaction, [α-KIC] may follow one of two pathways. In the first, HMB is produced from [α-KIC] by the cytosolic enzyme KIC dioxygenase (Sabourin and Bieber 1983). The cytosolic dioxygenase has been characterized extensively and differs from the mitochondrial form in that the dioxygenase enzyme is a cytosolic enzyme, whereas the dehydrogenase enzyme is found exclusively in the mitochondrion (Sabourin and Bieber 1981, 1983). Importantly, this route of HMB formation is direct and completely dependent of liver KIC dioxygenase. Following this pathway, HMB in the cytosol is first converted to cytosolic β-hydroxy-β-methylglutaryl-CoA (HMG-CoA), which can then be directed for cholesterol synthesis (Rudney 1957) (Fig. 1). In fact, numerous biochemical studies have shown that HMB is a precursor of cholesterol (Zabin and Bloch 1951; Nissen et al. 2000).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Amino+Acids&rft.atitle=HMB+supplementation%3A+clinical+and+athletic+performance-related+effects+and+mechanisms+of+action&rft.volume=40&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1015-%3C%2Fspan%3E1025&rft.date=2011-04&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A11120110%23id-name%3DS2CID&rft_id=info%3Apmid%2F20607321&rft_id=info%3Adoi%2F10.1007%2Fs00726-010-0678-0&rft.aulast=Zanchi&rft.aufirst=NE&rft.au=Gerlinger-Romero%2C+F&rft.au=Guimar%C3%A3es-Ferreira%2C+L&rft.au=de+Siqueira+Filho%2C+MA&rft.au=Felitti%2C+V&rft.au=Lira%2C+FS&rft.au=Seelaender%2C+M&rft.au=Lancha%2C+AH&rft_id=https%3A%2F%2Frepositorio.unal.edu.co%2Fhandle%2Funal%2F77957&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHMG-CoA" class="Z3988"></span></span> </li> <li id="cite_note-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-8">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFGarrett2013" class="citation book cs1">Garrett RH (2013). <i>Biochemistry</i>. Cengage Learning. p. 856. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-305-57720-6" title="Special:BookSources/978-1-305-57720-6"><bdi>978-1-305-57720-6</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Biochemistry&rft.pages=856&rft.pub=Cengage+Learning&rft.date=2013&rft.isbn=978-1-305-57720-6&rft.aulast=Garrett&rft.aufirst=Reginald+H.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHMG-CoA" class="Z3988"></span></span> </li> <li id="cite_note-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-9">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHainesSteussyStauffacherWiest2012" class="citation journal cs1">Haines BE, Steussy CN, Stauffacher CV, Wiest O (October 2012). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3522576">"Molecular modeling of the reaction pathway and hydride transfer reactions of HMG-CoA reductase"</a>. <i>Biochemistry</i>. <b>51</b> (40): <span class="nowrap">7983–</span>95. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fbi3008593">10.1021/bi3008593</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3522576">3522576</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/22971202">22971202</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Biochemistry&rft.atitle=Molecular+modeling+of+the+reaction+pathway+and+hydride+transfer+reactions+of+HMG-CoA+reductase&rft.volume=51&rft.issue=40&rft.pages=%3Cspan+class%3D%22nowrap%22%3E7983-%3C%2Fspan%3E95&rft.date=2012-10&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3522576%23id-name%3DPMC&rft_id=info%3Apmid%2F22971202&rft_id=info%3Adoi%2F10.1021%2Fbi3008593&rft.aulast=Haines&rft.aufirst=BE&rft.au=Steussy%2C+CN&rft.au=Stauffacher%2C+CV&rft.au=Wiest%2C+O&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3522576&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHMG-CoA" class="Z3988"></span></span> </li> </ol></div></div> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist 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navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Cholesterol_and_steroid_intermediates" title="Template:Cholesterol and steroid intermediates"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Cholesterol_and_steroid_intermediates" title="Template talk:Cholesterol and steroid intermediates"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Cholesterol_and_steroid_intermediates" title="Special:EditPage/Template:Cholesterol and steroid intermediates"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Cholesterol_and_steroid_metabolic_intermediates189" style="font-size:114%;margin:0 4em"><a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a> and <a href="/wiki/Steroid" title="Steroid">steroid</a> <a href="/wiki/Metabolic_intermediate" title="Metabolic intermediate">metabolic intermediates</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Mevalonate_pathway" title="Mevalonate pathway">Mevalonate pathway</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">to <a class="mw-selflink selflink">HMG-CoA</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetyl-CoA" title="Acetyl-CoA">Acetyl-CoA</a></li> <li><a href="/wiki/Acetoacetyl-CoA" title="Acetoacetyl-CoA">Acetoacetyl-CoA</a></li> <li><a href="/wiki/Beta-Hydroxy_beta-methylbutyric_acid" class="mw-redirect" title="Beta-Hydroxy beta-methylbutyric acid">HMB</a></li> <li><a href="/wiki/Beta-Hydroxy_beta-methylbutyryl-CoA" class="mw-redirect" title="Beta-Hydroxy beta-methylbutyryl-CoA">HMB-CoA</a></li> <li><a class="mw-selflink selflink">HMG-CoA</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Ketone_bodies" title="Ketone bodies">Ketone bodies</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetone" title="Acetone">Acetone</a></li> <li><a href="/wiki/Acetoacetic_acid" title="Acetoacetic acid">Acetoacetic acid</a></li> <li><a href="/wiki/Beta-Hydroxybutyric_acid" class="mw-redirect" title="Beta-Hydroxybutyric acid">β-Hydroxybutyric acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">to <a href="/wiki/Dimethylallyl_pyrophosphate" title="Dimethylallyl pyrophosphate">DMAPP</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Mevalonic_acid" title="Mevalonic acid">Mevalonic acid</a></li> <li><a href="/wiki/Phosphomevalonic_acid" title="Phosphomevalonic acid">Phosphomevalonic acid</a></li> <li><a href="/wiki/5-Diphosphomevalonic_acid" title="5-Diphosphomevalonic acid">5-Diphosphomevalonic acid</a></li> <li><a href="/wiki/Isopentenyl_pyrophosphate" title="Isopentenyl pyrophosphate">Isopentenyl pyrophosphate</a></li> <li><a href="/wiki/Dimethylallyl_pyrophosphate" title="Dimethylallyl pyrophosphate">Dimethylallyl pyrophosphate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Geranyl-</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Geranyl_pyrophosphate" title="Geranyl pyrophosphate">Geranyl pyrophosphate</a></li> <li><a href="/wiki/Geranylgeranyl_pyrophosphate" title="Geranylgeranyl pyrophosphate">Geranylgeranyl pyrophosphate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carotenoid" title="Carotenoid">Carotenoid</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Prephytoene_diphosphate" title="Prephytoene diphosphate">Prephytoene diphosphate</a></li> <li><a href="/wiki/Phytoene" title="Phytoene">Phytoene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Non-mevalonate_pathway" title="Non-mevalonate pathway">Non-mevalonate pathway</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1-Deoxy-D-xylulose_5-phosphate" title="1-Deoxy-D-xylulose 5-phosphate">DOXP</a></li> <li><a href="/wiki/2-C-methylerythritol_4-phosphate" class="mw-redirect" title="2-C-methylerythritol 4-phosphate">MEP</a></li> <li><a href="/wiki/4-diphosphocytidyl-2-C-methylerythritol" class="mw-redirect" title="4-diphosphocytidyl-2-C-methylerythritol">CDP-ME</a></li> <li><a href="/wiki/4-diphosphocytidyl-2-C-methyl-D-erythritol_2-phosphate" class="mw-redirect" title="4-diphosphocytidyl-2-C-methyl-D-erythritol 2-phosphate">CDP-MEP</a></li> <li><a href="/wiki/2-C-methyl-D-erythritol_2,4-cyclopyrophosphate" class="mw-redirect" title="2-C-methyl-D-erythritol 2,4-cyclopyrophosphate">MEcPP</a></li> <li><a href="/wiki/(E)-4-Hydroxy-3-methyl-but-2-enyl_pyrophosphate" title="(E)-4-Hydroxy-3-methyl-but-2-enyl pyrophosphate">HMB-PP</a></li> <li><a href="/wiki/Isopentenyl_pyrophosphate" title="Isopentenyl pyrophosphate">IPP</a></li> <li><a href="/wiki/Dimethylallyl_pyrophosphate" title="Dimethylallyl pyrophosphate">DMAPP</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">To <a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Farnesyl_pyrophosphate" title="Farnesyl pyrophosphate">Farnesyl pyrophosphate</a></li> <li><a href="/wiki/Squalene" title="Squalene">Squalene</a></li> <li><a href="/wiki/2,3-Oxidosqualene" title="2,3-Oxidosqualene">2,3-Oxidosqualene</a></li> <li><a href="/wiki/Lanosterol" title="Lanosterol">Lanosterol</a></li></ul> <ul><li><a href="/wiki/Lanosterol" title="Lanosterol">Lanosterol</a></li> <li><a href="/w/index.php?title=14-demethyllanosterol&action=edit&redlink=1" class="new" title="14-demethyllanosterol (page does not exist)">14-demethyllanosterol</a></li> <li><a href="/w/index.php?title=4alpha-Methylzymosterol&action=edit&redlink=1" class="new" title="4alpha-Methylzymosterol (page does not exist)">4alpha-Methylzymosterol</a></li> <li><a href="/w/index.php?title=Zymosterone&action=edit&redlink=1" class="new" title="Zymosterone (page does not exist)">Zymosterone</a></li> <li><a href="/wiki/Zymosterol" title="Zymosterol">Zymosterol</a></li></ul> <ul><li><a href="/wiki/Zymosterol" title="Zymosterol">Zymosterol</a></li> <li><a href="/w/index.php?title=Zymostenol&action=edit&redlink=1" class="new" title="Zymostenol (page does not exist)">Zymostenol</a></li> <li><a href="/wiki/Lathosterol" title="Lathosterol">Lathosterol</a></li> <li><a href="/wiki/7-Dehydrocholesterol" title="7-Dehydrocholesterol">7-Dehydrocholesterol</a></li> <li><a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a></li></ul> <ul><li><a href="/wiki/Zymosterol" title="Zymosterol">Zymosterol</a></li> <li><a href="/w/index.php?title=Cholesta-7,24-dien-3-ol&action=edit&redlink=1" class="new" title="Cholesta-7,24-dien-3-ol (page does not exist)">Cholesta-7,24-dien-3-ol</a></li> <li><a href="/wiki/7-Dehydrodesmosterol" title="7-Dehydrodesmosterol">7-Dehydrodesmosterol</a></li> <li><a href="/wiki/Desmosterol" title="Desmosterol">Desmosterol</a></li> <li><a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">From <a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a> <br />to <a href="/wiki/Steroid" title="Steroid">Steroid hormones</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/22R-Hydroxycholesterol" title="22R-Hydroxycholesterol">22<i>R</i>-Hydroxycholesterol</a></li> <li><a href="/wiki/20%CE%B1,22R-Dihydroxycholesterol" title="20α,22R-Dihydroxycholesterol">20α,22<i>R</i>-Dihydroxycholesterol</a></li> <li>See <a href="/wiki/Template:Steroid_hormones" title="Template:Steroid hormones">here</a> instead.</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Nonhuman</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">To <a href="/wiki/Sitosterol" class="mw-redirect" title="Sitosterol">Sitosterol</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cycloartenol" title="Cycloartenol">Cycloartenol</a></li> <li><a href="/w/index.php?title=Cycloeucalenol&action=edit&redlink=1" class="new" title="Cycloeucalenol (page does not exist)">Cycloeucalenol</a></li> <li><a href="/wiki/Obtusifoliol" title="Obtusifoliol">Obtusifoliol</a></li> <li><a href="/wiki/4%CE%B1-methylfecosterol" class="mw-redirect" title="4α-methylfecosterol">4α-methylfecosterol</a></li> <li><a href="/wiki/Isofucosterol" title="Isofucosterol">Isofucosterol</a></li> <li><a href="/wiki/24-Methylenelophenol" title="24-Methylenelophenol">24-Methylenelophenol</a></li> <li><a href="/wiki/Sitosterol" class="mw-redirect" title="Sitosterol">Sitosterol</a></li> <li>More <a href="/wiki/Phytosterol" title="Phytosterol">Phytosterols</a> see <a href="/wiki/Template:Steroid_hormones" title="Template:Steroid hormones">here</a> instead.</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">To <a href="/wiki/Ergocalciferol" title="Ergocalciferol">Ergocalciferol</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Fecosterol" title="Fecosterol">Fecosterol</a></li> <li><a href="/wiki/Episterol" title="Episterol">Episterol</a></li> <li><a href="/wiki/Ergostatrienol" class="mw-redirect" title="Ergostatrienol">Ergostatrienol</a></li> <li><a href="/w/index.php?title=Ergostatetraenol&action=edit&redlink=1" class="new" title="Ergostatetraenol (page does not exist)">Ergostatetraenol</a></li> <li><a href="/wiki/Ergosterol" title="Ergosterol">Ergosterol</a></li> <li><a href="/wiki/Ergocalciferol" title="Ergocalciferol">Ergocalciferol</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="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 class="mw-selflink selflink">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> <p><br /> </p> <style data-mw-deduplicate="TemplateStyles:r1271159938">.mw-parser-output .asbox{position:relative;overflow:hidden}.mw-parser-output .asbox table{background:transparent}.mw-parser-output .asbox p{margin:0}.mw-parser-output .asbox p+p{margin-top:0.25em}.mw-parser-output .asbox-body{font-style:italic}.mw-parser-output .asbox-note{font-size:smaller}.mw-parser-output .asbox .navbar{position:absolute;top:-0.75em;right:1em;display:none}.mw-parser-output :not(p):not(.asbox)+style+.asbox,.mw-parser-output :not(p):not(.asbox)+link+.asbox{margin-top:3em}</style><div role="note" class="metadata plainlinks asbox stub"><table role="presentation"><tbody><tr class="noresize"><td><span typeof="mw:File"><a href="/wiki/File:AlphaHelixSection_(yellow).svg" class="mw-file-description"><img alt="Stub icon" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/42/AlphaHelixSection_%28yellow%29.svg/40px-AlphaHelixSection_%28yellow%29.svg.png" decoding="async" width="40" height="12" class="mw-file-element" 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