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class="vector-toc-list"> </ul> </li> <li id="toc-Other_uses" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Other_uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Other uses</span> </div> </a> <ul id="toc-Other_uses-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Isomers" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Isomers"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Isomers</span> </div> </a> <ul id="toc-Isomers-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" 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Available in 27 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-27" 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">27 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%AD%D9%85%D8%B6_%D8%A7%D9%84%D9%83%D8%A7%D9%81%D8%A6%D9%8A%D9%83" title="حمض الكافئيك – Arabic" lang="ar" hreflang="ar" data-title="حمض الكافئيك" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%DA%A9%D8%A7%D9%81%D8%A6%DB%8C%DA%A9_%D8%A7%D8%B3%DB%8C%D8%AF" title="کافئیک اسید – South Azerbaijani" lang="azb" hreflang="azb" data-title="کافئیک اسید" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%9A%D0%B0%D1%84%D0%B5%D0%B5%D0%BD%D0%B0_%D0%BA%D0%B8%D1%81%D0%B5%D0%BB%D0%B8%D0%BD%D0%B0" title="Кафеена киселина – Bulgarian" lang="bg" hreflang="bg" data-title="Кафеена киселина" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Kofeinska_kiselina" title="Kofeinska kiselina – Bosnian" lang="bs" hreflang="bs" data-title="Kofeinska kiselina" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/%C3%80cid_cafeic" title="Àcid cafeic – Catalan" lang="ca" hreflang="ca" data-title="Àcid cafeic" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Kyselina_k%C3%A1vov%C3%A1" title="Kyselina kávová – Czech" lang="cs" hreflang="cs" data-title="Kyselina kávová" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Kaffees%C3%A4ure" title="Kaffeesäure – German" lang="de" hreflang="de" data-title="Kaffeesäure" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/%C3%81cido_cafeico" title="Ácido cafeico – Spanish" lang="es" hreflang="es" data-title="Ácido cafeico" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Kafeata_acido" title="Kafeata acido – Esperanto" lang="eo" hreflang="eo" data-title="Kafeata acido" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Azido_kafeiko" title="Azido kafeiko – Basque" lang="eu" hreflang="eu" data-title="Azido kafeiko" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%DA%A9%D8%A7%D9%81%D8%A6%DB%8C%DA%A9_%D8%A7%D8%B3%DB%8C%D8%AF" title="کافئیک اسید – Persian" lang="fa" hreflang="fa" data-title="کافئیک اسید" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Acide_caf%C3%A9ique" title="Acide caféique – French" lang="fr" hreflang="fr" data-title="Acide caféique" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%BB%A4%ED%94%BC%EC%82%B0" title="커피산 – Korean" lang="ko" hreflang="ko" data-title="커피산" 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/Acido_caffeico" title="Acido caffeico – Italian" lang="it" hreflang="it" data-title="Acido caffeico" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/K%C3%A1v%C3%A9sav" title="Kávésav – Hungarian" lang="hu" hreflang="hu" data-title="Kávésav" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Koffiezuur" title="Koffiezuur – Dutch" lang="nl" hreflang="nl" data-title="Koffiezuur" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%B3%E3%83%BC%E3%83%92%E3%83%BC%E9%85%B8" title="コーヒー酸 – Japanese" lang="ja" hreflang="ja" data-title="コーヒー酸" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Kwas_kawowy" title="Kwas kawowy – Polish" lang="pl" hreflang="pl" data-title="Kwas kawowy" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/%C3%81cido_cafeico" title="Ácido cafeico – Portuguese" lang="pt" hreflang="pt" data-title="Ácido cafeico" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Acid_cafeic" title="Acid cafeic – Romanian" lang="ro" hreflang="ro" data-title="Acid cafeic" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%9A%D0%BE%D1%84%D0%B5%D0%B9%D0%BD%D0%B0%D1%8F_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0" title="Кофейная кислота – Russian" lang="ru" hreflang="ru" data-title="Кофейная кислота" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Kyselina_k%C3%A1vov%C3%A1" title="Kyselina kávová – Slovak" lang="sk" hreflang="sk" data-title="Kyselina kávová" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Kofeinska_kiselina" title="Kofeinska kiselina – Serbian" lang="sr" hreflang="sr" data-title="Kofeinska kiselina" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Kofeinska_kiselina" title="Kofeinska kiselina – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Kofeinska kiselina" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Kahvihappo" title="Kahvihappo – Finnish" lang="fi" hreflang="fi" data-title="Kahvihappo" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%9A%D0%B0%D0%B2%D0%BE%D0%B2%D0%B0_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0" title="Кавова кислота – Ukrainian" lang="uk" hreflang="uk" data-title="Кавова кислота" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E5%92%96%E5%95%A1%E9%85%B8" title="咖啡酸 – Chinese" lang="zh" hreflang="zh" data-title="咖啡酸" data-language-autonym="中文" data-language-local-name="Chinese" 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id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><style data-mw-deduplicate="TemplateStyles:r1084375498">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> <table class="infobox ib-chembox"> <caption>Caffeic acid </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Kaffees%C3%A4ure.svg" class="mw-file-description" title="2D diagram of caffeic acid"><img alt="2D diagram of caffeic acid" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/Kaffees%C3%A4ure.svg/220px-Kaffees%C3%A4ure.svg.png" decoding="async" width="220" height="108" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/Kaffees%C3%A4ure.svg/330px-Kaffees%C3%A4ure.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c3/Kaffees%C3%A4ure.svg/440px-Kaffees%C3%A4ure.svg.png 2x" data-file-width="300" data-file-height="147" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Cafeic-acid-3D.png" class="mw-file-description" title="3D ball-and-stick model of caffeic acid"><img alt="3D ball-and-stick model of caffeic acid" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/29/Cafeic-acid-3D.png/220px-Cafeic-acid-3D.png" decoding="async" width="220" height="129" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/29/Cafeic-acid-3D.png/330px-Cafeic-acid-3D.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/29/Cafeic-acid-3D.png/440px-Cafeic-acid-3D.png 2x" data-file-width="1556" data-file-height="914" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:CaffeicAcid3d.png" class="mw-file-description" title="3D space filling model of caffeic acid"><img alt="3D space filling model of caffeic acid" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ef/CaffeicAcid3d.png/220px-CaffeicAcid3d.png" decoding="async" width="220" height="152" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ef/CaffeicAcid3d.png/330px-CaffeicAcid3d.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ef/CaffeicAcid3d.png/440px-CaffeicAcid3d.png 2x" data-file-width="736" data-file-height="510" /></a></span> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">IUPAC names</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">3-(3,4-Dihydroxyphenyl)-2-propenoic acid<br />3,4-Dihydroxycinnamic acid<br /><i>trans</i>-Caffeate<br />3,4-Dihydroxy-<i>trans</i>-cinnamate<br />(<i>E</i>)-3-(3,4-dihydroxyphenyl)-2-propenoic acid<br />3,4-Dihydroxybenzeneacrylicacid<br />3-(3,4-Dihydroxyphenyl)-2-propenoic acid</div> </td></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">(2<i>E</i>)-3-(3,4-Dihydroxyphenyl)prop-2-enoic acid</div></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=501-16-6">501-16-6</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><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=331-39-5">331-39-5</a></span> (non-specific)<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%29%5CC%3DC%5Cc1cc%28O%29c%28O%29cc1">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Beilstein_database" title="Beilstein database">Beilstein Reference</a></div> </td> <td>1954563 </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=16433">CHEBI:16433</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL145">ChEMBL145</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.600426.html">600426</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB01880">DB01880</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/100.005.784">100.005.784</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q414116#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><a href="/wiki/European_Community_number" title="European Community number"><span title="European Community number (chemical identifier)">EC Number</span></a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>206-361-2</li></ul></div> </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=5155">5155</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C01481">C01481</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/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/689043">689043</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/U2S3A33KVM">U2S3A33KVM</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID5020231,">DTXSID901316055 DTXSID5020231, DTXSID901316055</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q414116#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2+<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: QAIPRVGONGVQAS-DUXPYHPUSA-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/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2+</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: QAIPRVGONGVQAS-DUXPYHPUBE</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">O=C(O)\C=C\c1cc(O)c(O)cc1</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td>C<sub>9</sub>H<sub>8</sub>O<sub>4</sub>  </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td>180.16 g/mol    </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>1.478 g/cm<sup>3</sup> </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>223 to 225 °C (433 to 437 °F; 496 to 498 K) </td></tr> <tr> <td><a href="/wiki/Ultraviolet%E2%80%93visible_spectroscopy" title="Ultraviolet–visible spectroscopy">UV-vis</a> (λ<sub>max</sub>) </td> <td>327 nm and a shoulder at c. 295 nm in acidified methanol<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals" title="Globally Harmonized System of Classification and Labelling of Chemicals"><b>GHS</b> labelling</a>: </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_pictograms" title="GHS hazard pictograms">Pictograms</a></div> </td> <td><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-exclam.svg" class="mw-file-description" title="GHS07: Exclamation mark"><img alt="GHS07: Exclamation mark" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/50px-GHS-pictogram-exclam.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/75px-GHS-pictogram-exclam.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/100px-GHS-pictogram-exclam.svg.png 2x" data-file-width="512" data-file-height="512" /></a></span><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-silhouette.svg" class="mw-file-description" title="GHS08: Health hazard"><img alt="GHS08: Health hazard" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/50px-GHS-pictogram-silhouette.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/75px-GHS-pictogram-silhouette.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/100px-GHS-pictogram-silhouette.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals#Signal_word" title="Globally Harmonized System of Classification and Labelling of Chemicals">Signal word</a></div> </td> <td><b>Warning</b> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_statements" title="GHS hazard statements">Hazard statements</a></div> </td> <td><abbr class="abbr" title="H315: Causes skin irritation">H315</abbr>, <abbr class="abbr" title="H319: Causes serious eye irritation">H319</abbr>, <abbr class="abbr" title="H335: May cause respiratory irritation">H335</abbr>, <abbr class="abbr" title="H351: Suspected of causing cancer">H351</abbr>, <abbr class="abbr" title="H361: Suspected of damaging fertility or the unborn child">H361</abbr> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_precautionary_statements" title="GHS precautionary statements">Precautionary statements</a></div> </td> <td><abbr class="abbr" title="P201: Obtain special instructions before use.">P201</abbr>, <abbr class="abbr" title="P202: Do not handle until all safety precautions have been read and understood.">P202</abbr>, <abbr class="abbr" title="P261: Avoid breathing dust/fume/gas/mist/vapours/spray.">P261</abbr>, <abbr class="abbr" title="P264: Wash ... thoroughly after handling.">P264</abbr>, <abbr class="abbr" title="P271: Use only outdoors or in a well-ventilated area.">P271</abbr>, <abbr class="abbr" title="P280: Wear protective gloves/protective clothing/eye protection/face protection.">P280</abbr>, <abbr class="abbr" title="P281: Use personal protective equipment as required.">P281</abbr>, <abbr class="abbr" title="P302+P352: IF ON SKIN: Wash with soap and water.">P302+P352</abbr>, <abbr class="abbr" title="P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing.">P304+P340</abbr>, <abbr class="abbr" title="P305+P351+P338: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.">P305+P351+P338</abbr>, <abbr class="abbr" title="P308+P313: IF exposed or concerned: Get medical advice/attention.">P308+P313</abbr>, <abbr class="abbr" title="P312: Call a POISON CENTER or doctor/physician if you feel unwell.">P312</abbr>, <abbr class="abbr" title="P321: Specific treatment (see ... on this label).">P321</abbr>, <abbr class="abbr" title="P332+P313: If skin irritation occurs: Get medical advice/attention.">P332+P313</abbr>, <abbr class="abbr" title="P337+P313: If eye irritation persists: Get medical advice/attention.">P337+P313</abbr>, <abbr class="abbr" title="P362: Take off contaminated clothing.">P362</abbr>, <abbr class="abbr" title="P403+P233: Store in a well ventilated place. Keep container tightly closed.">P403+P233</abbr>, <abbr class="abbr" title="P405: Store locked up.">P405</abbr>, <abbr class="abbr" title="P501: Dispose of contents/container to ...">P501</abbr> </td></tr> <tr> <td><a href="/wiki/NFPA_704" title="NFPA 704"><b>NFPA 704</b></a> (fire diamond) </td> <td><style data-mw-deduplicate="TemplateStyles:r1170367383">.mw-parser-output .nfpa-704-diamond-ref{float:right;padding:1px;text-align:right}.mw-parser-output .nfpa-704-diamond-container{width:82px;font-family:sans-serif;margin:0 auto}.mw-parser-output .nfpa-704-diamond-container-ref{float:left;margin-left:1em}.mw-parser-output .nfpa-704-diamond-images{float:left;font-size:20px;text-align:center;position:relative;height:80px;width:80px;padding:1px}.mw-parser-output .nfpa-704-diamond-map{position:absolute;height:80px;width:80px}.mw-parser-output .nfpa-704-diamond .noresize{margin:0 auto}.mw-parser-output .nfpa-704-diamond-code{line-height:1em;text-align:center;position:absolute}.mw-parser-output .nfpa-704-diamond-code>a{color:black}.mw-parser-output .nfpa-704-diamond-blue{width:13px;top:31px;left:15px}.mw-parser-output .nfpa-704-diamond-red{width:12px;top:12px;left:35px}.mw-parser-output .nfpa-704-diamond-yellow{width:13px;top:31px;left:54px}.mw-parser-output .nfpa-704-diamond-white-image{position:relative;top:51px;left:0}.mw-parser-output .nfpa-704-diamond-white-text{vertical-align:middle;text-align:center;line-height:80%;position:absolute;top:52px}.mw-parser-output .nfpa-704-diamond-white-text a>span{position:absolute;color:black}.mw-parser-output .nfpa-704-diamond-white-wors{font-size:15px;width:23px;left:29px}.mw-parser-output .nfpa-704-diamond-white-wox{font-size:15px;font-stretch:condensed;width:21px;line-height:80%;top:-4px;left:29px}.mw-parser-output .nfpa-704-diamond-white-abcp{font-size:13.5px;font-stretch:condensed;width:28px;left:26px}.mw-parser-output .nfpa-704-diamond-white-ac{font-size:10px;width:30px;left:25px}.mw-parser-output .nfpa-704-diamond-white-strike{text-decoration:line-through}</style><div class="nfpa-704-diamond notheme"><div class="nfpa-704-diamond-container"><div class="nfpa-704-diamond-images nounderlines"> <div class="nfpa-704-diamond-map"><figure class="noresize" typeof="mw:File"><span><img alt="NFPA 704 four-colored diamond" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/80px-NFPA_704.svg.png" decoding="async" width="80" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/120px-NFPA_704.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/160px-NFPA_704.svg.png 2x" data-file-width="512" data-file-height="512" usemap="#ImageMap_811dcee2cbfc5fb2" /></span><map name="ImageMap_811dcee2cbfc5fb2"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine" title="Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine" /><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" title="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" /><area href="/wiki/NFPA_704#Yellow" shape="poly" coords="70,23,94,47,70,70,47,47" alt="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" /><area href="/wiki/NFPA_704#White" shape="poly" coords="47,47,70,70,47,94,23,70" alt="Special hazards (white): no code" title="Special hazards (white): no code" /></map><figcaption></figcaption></figure></div><div class="nfpa-704-diamond-code nfpa-704-diamond-blue"> <a href="/wiki/NFPA_704#Blue" title="NFPA 704"><span title="Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine" class="notheme mw-no-invert">1</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-red"> <a href="/wiki/NFPA_704#Red" title="NFPA 704"><span title="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" class="notheme mw-no-invert">1</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-yellow"> <a href="/wiki/NFPA_704#Yellow" title="NFPA 704"><span title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" class="notheme mw-no-invert">0</span></a></div></div></div></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Related compounds </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related compounds</div> </td> <td><a href="/wiki/Chlorogenic_acid" title="Chlorogenic acid">Chlorogenic acid</a><br /><a href="/wiki/Cichoric_acid" class="mw-redirect" title="Cichoric acid">Cichoric acid</a><br /><a href="/wiki/Coumaric_acid" title="Coumaric acid">Coumaric acid</a><br /><a href="/wiki/Quinic_acid" title="Quinic acid">Quinic acid</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="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=443671399&page2=Caffeic+acid">verify</a></span> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <sup><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup> ?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>Caffeic acid</b> is an <a href="/wiki/Organic_compound" title="Organic compound">organic compound</a> with the formula <style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">(HO)<sub class="template-chem2-sub">2</sub>C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">3</sub>CH=CHCO<sub class="template-chem2-sub">2</sub>H</span>. It is a polyphenol. It is a yellow solid. Structurally, it is classified as a <a href="/wiki/Hydroxycinnamic_acid" title="Hydroxycinnamic acid">hydroxycinnamic acid</a>. The molecule consists of both <a href="/wiki/Phenol" title="Phenol">phenolic</a> and <a href="/wiki/Acrylic_acid" title="Acrylic acid">acrylic</a> functional groups. It is found in all plants as an intermediate in the <a href="/wiki/Biosynthesis" title="Biosynthesis">biosynthesis</a> of <a href="/wiki/Lignin" title="Lignin">lignin</a>, one of the principal components of <a href="/wiki/Biomass" title="Biomass">biomass</a> and its residues.<sup id="cite_ref-Boerjan_2-0" class="reference"><a href="#cite_note-Boerjan-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> It is unrelated to <a href="/wiki/Caffeine" title="Caffeine">caffeine</a>. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Natural_occurrences">Natural occurrences</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Caffeic_acid&action=edit&section=1" title="Edit section: Natural occurrences"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Caffeic acid can be found in the bark of <i><a href="/wiki/Eucalyptus_globulus" title="Eucalyptus globulus">Eucalyptus globulus</a></i><sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> the <a href="/wiki/Barley" title="Barley">barley</a> grain <i>Hordeum vulgare</i> and the herb <i><a href="/wiki/Dipsacus" title="Dipsacus">Dipsacus</a> asperoides</i>.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> It can also be found in the freshwater fern <i><a href="/wiki/Salvinia_molesta" title="Salvinia molesta">Salvinia molesta</a></i><sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> and in the mushroom <i><a href="/wiki/Phellinus_linteus" class="mw-redirect" title="Phellinus linteus">Phellinus linteus</a></i>.<sup id="cite_ref-pmid18827365_6-0" class="reference"><a href="#cite_note-pmid18827365-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Occurrences_in_food">Occurrences in food</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Caffeic_acid&action=edit&section=2" title="Edit section: Occurrences in food"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Free caffeic acid can be found in a variety of beverages, including brewed <a href="/wiki/Coffee" title="Coffee">coffee</a> at 63.1-96.0 mg per 100 ml<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> and red wine at 2 mg per 100 ml.<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> It is found at relatively high levels in herbs of the mint family, especially <a href="/wiki/Thyme" title="Thyme">thyme</a>, <a href="/wiki/Salvia_officinalis" title="Salvia officinalis">sage</a> and <a href="/wiki/Spearmint" title="Spearmint">spearmint</a> (at about 20 mg per 100 g), and in spices, such as <a href="/wiki/Cinnamomum_verum" title="Cinnamomum verum">Ceylon cinnamon</a> and <a href="/wiki/Illicium_verum" title="Illicium verum">star anise</a> (at about 22 mg per 100 g). Caffeic acid occurs at moderate levels in <a href="/wiki/Sunflower_seed" title="Sunflower seed">sunflower seeds</a> (8 mg per 100 g), <a href="/wiki/Apple_sauce" title="Apple sauce">apple sauce</a>, <a href="/wiki/Apricot" title="Apricot">apricots</a> and <a href="/wiki/Prune" title="Prune">prunes</a> (at about 1 mg per 100 g).<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> It occurs at remarkably high levels in <a href="/wiki/Aronia_melanocarpa" title="Aronia melanocarpa">black chokeberry</a> (141 mg per 100 g).<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> It is also quite high in the South American herb <a href="/wiki/Yerba_mate" class="mw-redirect" title="Yerba mate">yerba mate</a> (150 mg per 100 g based on <a href="/wiki/Thin-layer_chromatography" title="Thin-layer chromatography">thin-layer chromatography</a> <a href="/wiki/Densitometry" title="Densitometry">densitometry</a><sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> and HPLC <sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup>). It is also found at lower levels in <a href="/wiki/Barley" title="Barley">barley</a> and <a href="/wiki/Rye" title="Rye">rye</a>.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Biosynthesis">Biosynthesis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Caffeic_acid&action=edit&section=3" title="Edit section: Biosynthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Caffeic acid is biosynthesized by <a href="/wiki/Hydroxylation" title="Hydroxylation">hydroxylation</a> of <a href="/wiki/Coumaric_acid" title="Coumaric acid">coumaroyl</a> ester of <a href="/wiki/Chlorogenic_acid" title="Chlorogenic acid">quinic acid</a> (esterified through a side chain alcohol). This hydroxylation produces the caffeic acid ester of <a href="/wiki/Shikimic_acid" title="Shikimic acid">shikimic acid</a>, which converts to <a href="/wiki/Chlorogenic_acid" title="Chlorogenic acid">chlorogenic acid</a>. It is the precursor to <a href="/wiki/Ferulic_acid" title="Ferulic acid">ferulic acid</a>, <a href="/wiki/Coniferyl_alcohol" title="Coniferyl alcohol">coniferyl alcohol</a>, and <a href="/wiki/Sinapyl_alcohol" title="Sinapyl alcohol">sinapyl alcohol</a>, all of which are significant building blocks in lignin.<sup id="cite_ref-Boerjan_2-1" class="reference"><a href="#cite_note-Boerjan-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> The transformation to ferulic acid is catalyzed by the <a href="/wiki/Enzyme" title="Enzyme">enzyme</a> <a href="/wiki/Caffeate_O-methyltransferase" title="Caffeate O-methyltransferase">caffeate <i>O</i>-methyltransferase</a>. </p><p>Caffeic acid and its derivative <a href="/wiki/Caffeic_acid_phenethyl_ester" title="Caffeic acid phenethyl ester">caffeic acid phenethyl ester</a> (CAPE) are produced in many kinds of plants.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-urlActivities_of_a_Specific_Chemical_Query_15-0" class="reference"><a href="#cite_note-urlActivities_of_a_Specific_Chemical_Query-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid11208940_16-0" class="reference"><a href="#cite_note-pmid11208940-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><figure class="mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:CaffeicAcIn.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/65/CaffeicAcIn.png/300px-CaffeicAcIn.png" decoding="async" width="300" height="140" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/65/CaffeicAcIn.png/450px-CaffeicAcIn.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/65/CaffeicAcIn.png/600px-CaffeicAcIn.png 2x" data-file-width="1464" data-file-height="681" /></a><figcaption>In plants, caffeic acid (middle) is formed from 4-hydroxycinnamic acid (left) and is transformed to <a href="/wiki/Ferulic_acid" title="Ferulic acid">ferulic acid</a>.</figcaption></figure></dd></dl> <div style="clear:left;" class=""></div> <p>Dihydroxyphenylalanine ammonia-lyase was presumed to use <a href="/wiki/L-DOPA" title="L-DOPA">3,4-dihydroxy-<small>L</small>-phenylalanine</a> (<small>L</small>-DOPA) to produce trans-caffeate and NH<sub>3</sub>. However, the EC number for this purported enzyme was deleted in 2007, as no evidence has emerged for its existence.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Biotransformation">Biotransformation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Caffeic_acid&action=edit&section=4" title="Edit section: Biotransformation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Caffeate_O-methyltransferase" title="Caffeate O-methyltransferase">Caffeate <i>O</i>-methyltransferase</a> is an enzyme responsible for the transformation of caffeic acid into <a href="/wiki/Ferulic_acid" title="Ferulic acid">ferulic acid</a>. </p><p>Caffeic acid and related <i>o</i>-diphenols are rapidly oxidized by <a href="/wiki/O-Diphenol_oxidase" class="mw-redirect" title="O-Diphenol oxidase"><i>o</i>-diphenol oxidases</a> in tissue extracts.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Biodegradation">Biodegradation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Caffeic_acid&action=edit&section=5" title="Edit section: Biodegradation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Caffeate_3,4-dioxygenase" title="Caffeate 3,4-dioxygenase">Caffeate 3,4-dioxygenase</a> is an enzyme that uses caffeic acid and oxygen to produce <a href="/w/index.php?title=3-(2-carboxyethenyl)-cis,cis-muconate&action=edit&redlink=1" class="new" title="3-(2-carboxyethenyl)-cis,cis-muconate (page does not exist)">3-(2-carboxyethenyl)-<i>cis</i>,<i>cis</i>-muconate</a>. </p><p>Caffeic acid is susceptible to <a href="/wiki/Autoxidation" title="Autoxidation">autoxidation</a>. <a href="/wiki/Glutathione" title="Glutathione">Glutathione</a> and <a href="/wiki/Thiol" title="Thiol">thiol</a> compounds (<a href="/wiki/Cysteine" title="Cysteine">cysteine</a>, <a href="/wiki/Thioglycolic_acid" title="Thioglycolic acid">thioglycolic acid</a> or <a href="/w/index.php?title=Thiocresol&action=edit&redlink=1" class="new" title="Thiocresol (page does not exist)">thiocresol</a>) or <a href="/wiki/Ascorbic" class="mw-redirect" title="Ascorbic">ascorbic</a> acid have a protective effect on browning and disappearance of caffeic acid.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> This browning is due to the conversion of <a href="/wiki/O-diphenol" class="mw-redirect" title="O-diphenol"><i>o</i>-diphenols</a> into reactive <a href="/wiki/O-quinone" class="mw-redirect" title="O-quinone"><i>o</i>-quinones</a>. Chemical oxidation of caffeic acid in acidic conditions using <a href="/wiki/Sodium_periodate" title="Sodium periodate">sodium periodate</a> leads to the formation of dimers with a furan structure (isomers of 2,5-(3′,4′-dihydroxyphenyl)tetrahydrofuran 3,4-dicarboxylic acid).<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> Caffeic acid can also be polymerized using the <a href="/wiki/Horseradish_peroxidase" title="Horseradish peroxidase">horseradish peroxidase</a>/<a href="/wiki/Hydrogen_peroxide" title="Hydrogen peroxide">H<sub>2</sub>O<sub>2</sub></a> oxidizing system.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Glycosides">Glycosides</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Caffeic_acid&action=edit&section=6" title="Edit section: Glycosides"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/3-O-caffeoylshikimic_acid" class="mw-redirect" title="3-O-caffeoylshikimic acid">3-<i>O</i>-caffeoylshikimic acid</a> (<a href="/wiki/Dactylifric_acid" title="Dactylifric acid">dactylifric acid</a>) and its isomers, are <a href="/wiki/Enzymic_browning" class="mw-redirect" title="Enzymic browning">enzymic browning</a> substrates found in dates (<i><a href="/wiki/Phoenix_dactylifera" class="mw-redirect" title="Phoenix dactylifera">Phoenix dactylifera</a></i> fruits).<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Pharmacology">Pharmacology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Caffeic_acid&action=edit&section=7" title="Edit section: Pharmacology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Caffeic acid has a variety of potential pharmacological effects in <i><a href="/wiki/In_vitro" title="In vitro">in vitro</a></i> studies and in animal models, and the inhibitory effect of caffeic acid on cancer cell proliferation by an oxidative mechanism in the human <a href="/wiki/HT1080" title="HT1080">HT-1080</a> <a href="/wiki/Fibrosarcoma" title="Fibrosarcoma">fibrosarcoma</a> cell line has recently been established.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p><p>Caffeic acid is an <a href="/wiki/Antioxidant" title="Antioxidant">antioxidant</a> <i>in vitro</i> and also <i><a href="/wiki/In_vivo" title="In vivo">in vivo</a></i>.<sup id="cite_ref-pmid11208940_16-1" class="reference"><a href="#cite_note-pmid11208940-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> Caffeic acid also shows immunomodulatory and <a href="/wiki/Anti-inflammatory" title="Anti-inflammatory">anti-inflammatory</a> activity. Caffeic acid outperformed the other antioxidants, reducing <a href="/wiki/Aflatoxin" title="Aflatoxin">aflatoxin</a> production by more than 95 percent. The studies are the first to show that oxidative stress that would otherwise trigger or enhance <i><a href="/wiki/Aspergillus_flavus" title="Aspergillus flavus">Aspergillus flavus</a></i> aflatoxin production can be stymied by caffeic acid. This opens the door to use as a natural <a href="/wiki/Fungicide" title="Fungicide">fungicide</a> by supplementing trees with antioxidants.<sup id="cite_ref-urlNuts’New_Aflatoxin_Fighter:_Caffeic_Acid?_24-0" class="reference"><a href="#cite_note-urlNuts’New_Aflatoxin_Fighter:_Caffeic_Acid?-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p><p>Studies of the <a href="/wiki/Carcinogenicity" class="mw-redirect" title="Carcinogenicity">carcinogenicity</a> of caffeic acid have mixed results. Some studies have shown that it inhibits <a href="/wiki/Carcinogenesis" title="Carcinogenesis">carcinogenesis</a>, and other experiments show carcinogenic effects.<sup id="cite_ref-Hirose_25-0" class="reference"><a href="#cite_note-Hirose-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> Oral administration of high doses of caffeic acid in rats has caused <a href="/wiki/Stomach" title="Stomach">stomach</a> <a href="/wiki/Papilloma" title="Papilloma">papillomas</a>.<sup id="cite_ref-Hirose_25-1" class="reference"><a href="#cite_note-Hirose-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> In the same study, high doses of combined antioxidants, including caffeic acid, showed a significant decrease in growth of <a href="/wiki/Colon_(anatomy)" class="mw-redirect" title="Colon (anatomy)">colon</a> <a href="/wiki/Tumor" class="mw-redirect" title="Tumor">tumors</a> in those same rats. No significant effect was noted otherwise. Caffeic acid is listed under some Hazard Data sheets as a potential carcinogen,<sup id="cite_ref-urlCaffeic_Acid_(IARC_Summary_&_Evaluation,_Volume_56,_1993)_26-0" class="reference"><a href="#cite_note-urlCaffeic_Acid_(IARC_Summary_&_Evaluation,_Volume_56,_1993)-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> as has been listed by the <a href="/wiki/International_Agency_for_Research_on_Cancer" title="International Agency for Research on Cancer">International Agency for Research on Cancer</a> as a <a href="/wiki/List_of_IARC_Group_2B_carcinogens" class="mw-redirect" title="List of IARC Group 2B carcinogens">Group 2B carcinogen</a> ("possibly carcinogenic to humans").<sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> More recent data show that <a href="/wiki/Bacteria" title="Bacteria">bacteria</a> in the rats' guts may alter the formation of <a href="/wiki/Metabolite" title="Metabolite">metabolites</a> of caffeic acid.<sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> Other than caffeic acid being a <a href="/wiki/Thiamine" title="Thiamine">thiamine</a> antagonist (antithiamine factor), there have been no known ill effects of caffeic acid in humans. Also, caffeic acid treatment attenuated lipopolysaccharide (LPS)-induced sickness behaviour in experimental animals by decreasing both peripheral and central <a href="/wiki/Cytokine" title="Cytokine">cytokine</a> levels along with oxidative stress inflicted by LPS.<sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Other_uses">Other uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Caffeic_acid&action=edit&section=8" title="Edit section: Other uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Caffeic acid may be the active ingredient in <a href="/wiki/Caffenol" title="Caffenol">caffenol</a>, a do-it-yourself black-and-white <a href="/wiki/Photographic_developer" title="Photographic developer">photographic developer</a> made from <a href="/wiki/Instant_coffee" title="Instant coffee">instant coffee</a>.<sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> The developing chemistry is similar to that of <a href="/wiki/Catechol" title="Catechol">catechol</a> or <a href="/wiki/Pyrogallol" title="Pyrogallol">pyrogallol</a>.<sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> </p><p>It is also used as a matrix in <a href="/wiki/Matrix-assisted_laser_desorption/ionization" title="Matrix-assisted laser desorption/ionization">MALDI</a> <a href="/wiki/Mass_spectrometry" title="Mass spectrometry">mass spectrometry</a> analyses.<sup id="cite_ref-pmid2520223_33-0" class="reference"><a href="#cite_note-pmid2520223-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Isomers">Isomers</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Caffeic_acid&action=edit&section=9" title="Edit section: Isomers"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Isomers with the same molecular formula and in the hydroxycinammic acids family are: </p> <ul><li><a href="/wiki/Umbellic_acid" title="Umbellic acid">Umbellic acid</a> (2,4-dihydroxycinnamic acid)</li> <li><a href="/wiki/2,3-Dihydroxycinnamic_acid" title="2,3-Dihydroxycinnamic acid">2,3-Dihydroxycinnamic acid</a></li> <li><a href="/wiki/2,5-Dihydroxycinnamic_acid" title="2,5-Dihydroxycinnamic acid">2,5-Dihydroxycinnamic acid</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=Caffeic_acid&action=edit&section=10" 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 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"Caffeic acid attenuates lipopolysaccharide-induced sickness behaviour and neuroinflammation in mice". <i>Neuroscience Letters</i>. <b>632</b>: 218–223. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.neulet.2016.08.044">10.1016/j.neulet.2016.08.044</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/27597761">27597761</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:5361129">5361129</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Neuroscience+Letters&rft.atitle=Caffeic+acid+attenuates+lipopolysaccharide-induced+sickness+behaviour+and+neuroinflammation+in+mice.&rft.volume=632&rft.pages=218-223&rft.date=2016-09-03&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A5361129%23id-name%3DS2CID&rft_id=info%3Apmid%2F27597761&rft_id=info%3Adoi%2F10.1016%2Fj.neulet.2016.08.044&rft.aulast=Basu&rft.aufirst=Mallik+S&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACaffeic+acid" class="Z3988"></span></span> </li> <li id="cite_note-31"><span class="mw-cite-backlink"><b><a href="#cite_ref-31">^</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://caffenol.blogspot.com/2010/03/caffenol-c-m-recipe.html">"Caffenol-C-M, recipe"</a>. <i>Caffenol blog</i>. 2 March 2010.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Caffenol+blog&rft.atitle=Caffenol-C-M%2C+recipe&rft.date=2010-03-02&rft_id=http%3A%2F%2Fcaffenol.blogspot.com%2F2010%2F03%2Fcaffenol-c-m-recipe.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACaffeic+acid" class="Z3988"></span></span> </li> <li id="cite_note-32"><span class="mw-cite-backlink"><b><a href="#cite_ref-32">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWilliams" class="citation web cs1">Williams, Scott. <a rel="nofollow" class="external text" href="http://people.rit.edu/andpph/text-coffee.html">"A Use for that Last Cup of Coffee: Film and Paper Development"</a>. <i>Technical Photographic Chemistry 1995 Class</i>. Imaging and Photographic Technology Department, School of Photographic Arts and Sciences, Rochester Institute of Technology.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Technical+Photographic+Chemistry+1995+Class&rft.atitle=A+Use+for+that+Last+Cup+of+Coffee%3A+Film+and+Paper+Development&rft.aulast=Williams&rft.aufirst=Scott&rft_id=http%3A%2F%2Fpeople.rit.edu%2Fandpph%2Ftext-coffee.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACaffeic+acid" class="Z3988"></span></span> </li> <li id="cite_note-pmid2520223-33"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid2520223_33-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBeavisChait1989" class="citation journal cs1">Beavis, R. C.; Chait, B. T. (Dec 1989). "Cinnamic acid derivatives as matrices for ultraviolet laser desorption mass spectrometry of proteins". <i>Rapid Commun. Mass Spectrom</i>. <b>3</b> (12): 432–435. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1989RCMS....3..432B">1989RCMS....3..432B</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Frcm.1290031207">10.1002/rcm.1290031207</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/2520223">2520223</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Rapid+Commun.+Mass+Spectrom.&rft.atitle=Cinnamic+acid+derivatives+as+matrices+for+ultraviolet+laser+desorption+mass+spectrometry+of+proteins&rft.volume=3&rft.issue=12&rft.pages=432-435&rft.date=1989-12&rft_id=info%3Apmid%2F2520223&rft_id=info%3Adoi%2F10.1002%2Frcm.1290031207&rft_id=info%3Abibcode%2F1989RCMS....3..432B&rft.aulast=Beavis&rft.aufirst=R.+C.&rft.au=Chait%2C+B.+T.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACaffeic+acid" class="Z3988"></span></span> </li> </ol></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Caffeic_acid&action=edit&section=11" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><link rel="mw-deduplicated-inline-style" 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coffee">History</a></li> <li><a href="/wiki/International_Coffee_Day" title="International Coffee Day">International Coffee Day</a></li> <li><a href="/wiki/Single-origin_coffee" title="Single-origin coffee">Single-origin coffee</a></li> <li><a href="/wiki/Third-wave_coffee" title="Third-wave coffee">Third-wave coffee</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Production</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/Coffee_production" title="Coffee production">Coffee production</a> <ul><li><a href="/wiki/Organic_coffee" title="Organic coffee">Organic coffee</a></li> <li><a href="/wiki/Shade-grown_coffee" title="Shade-grown coffee">Shade-grown coffee</a></li> <li><a href="/wiki/Sustainable_coffee" title="Sustainable coffee">Sustainable coffee</a></li></ul></li> <li><a href="/wiki/List_of_countries_by_coffee_production" title="List of countries by coffee production">List of countries by coffee production</a></li> <li><a href="/wiki/Coffee_roasting" title="Coffee roasting">Coffee roasting</a></li> <li><a href="/wiki/Coffee_wastewater" title="Coffee wastewater">Coffee wastewater</a></li> <li><a href="/wiki/Decaffeination" title="Decaffeination">Decaffeination</a></li> <li><a href="/wiki/Home_roasting_coffee" title="Home roasting coffee">Home roasting</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Coffea" title="Coffea">Species</a> and <br /><a href="/wiki/List_of_coffee_varieties" title="List of coffee varieties">varieties</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/Coffea_arabica" title="Coffea arabica">Arabica</a></i> <ul><li><a href="/wiki/Benguet_coffee" title="Benguet coffee">Benguet</a></li> <li><a href="/wiki/Jamaican_Blue_Mountain_Coffee" title="Jamaican Blue Mountain Coffee">Blue Mountain</a></li> <li><a href="/wiki/Guadeloupe_Bonifieur" title="Guadeloupe Bonifieur">Bonifieur</a></li> <li><a href="/wiki/Bourbon_coffee" title="Bourbon coffee">Bourbon</a></li> <li><a href="/wiki/Geisha_(coffee)" title="Geisha (coffee)">Geisha</a></li> <li><a href="/wiki/Kona_coffee" title="Kona coffee">Kona</a></li> <li><a href="/wiki/Maracaturra_coffee" title="Maracaturra coffee">Maracaturra</a></li> <li><a href="/wiki/Maragogipe_Coffee" title="Maragogipe Coffee">Maragogipe</a></li> <li><a href="/wiki/Molokai_coffee" title="Molokai coffee">Molokai</a></li> <li><a href="/wiki/S795_coffee" title="S795 coffee">S795</a></li> <li><a href="/wiki/Sagada_coffee" title="Sagada coffee">Sagada</a></li></ul></li> <li><i><a href="/wiki/Coffea_charrieriana" title="Coffea charrieriana">Charrieriana</a></i></li> <li><i><a href="/wiki/Coffea_liberica" title="Coffea liberica">Liberica</a></i> <ul><li><a href="/wiki/Kapeng_barako" title="Kapeng barako">Barako</a></li></ul></li> <li><i><a href="/wiki/Coffea_racemosa" title="Coffea racemosa">Racemosa</a></i></li> <li><i><a href="/wiki/Robusta_coffee" class="mw-redirect" title="Robusta coffee">Robusta</a></i> <ul><li><a href="/wiki/Kahawa_Sug" title="Kahawa Sug">Sulu</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Components</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/Cafestol" title="Cafestol">Cafestol</a></li> <li><a class="mw-selflink selflink">Caffeic acid</a></li> <li><a href="/wiki/Caffeine" title="Caffeine">Caffeine</a></li> <li><a href="/wiki/Coffee_bean" title="Coffee bean">Coffee bean</a></li> <li><a href="/wiki/Furan-2-ylmethanethiol" title="Furan-2-ylmethanethiol">Furan-2-ylmethanethiol</a></li> <li><a href="/wiki/Kahweol" title="Kahweol">Kahweol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Coffee_preparation" title="Coffee preparation">Preparation</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/AeroPress" title="AeroPress">AeroPress</a></li> <li><a href="/wiki/Arabic_coffee" title="Arabic coffee">Arabic coffee</a></li> <li><a href="/wiki/Jebena" title="Jebena">Jebena</a></li> <li><a href="/wiki/Brewed_coffee" class="mw-redirect" title="Brewed coffee">Brewed coffee</a></li> <li><a href="/wiki/Chemex_Coffeemaker" title="Chemex Coffeemaker">Chemex</a></li> <li><a href="/wiki/Cezve" title="Cezve">Cezve</a></li> <li><a href="/wiki/Chorreador" title="Chorreador">Chorreador</a></li> <li><a href="/wiki/Coffeemaker" title="Coffeemaker">Coffeemaker</a></li> <li><a href="/wiki/Cold_brew_coffee" title="Cold brew coffee">Cold brew</a> <ul><li><a href="/wiki/Nitro_cold_brew_coffee" class="mw-redirect" title="Nitro cold brew coffee">nitro</a></li></ul></li> <li><a href="/wiki/Drip_coffee" title="Drip coffee">Drip coffee</a></li> <li><a href="/wiki/Espresso" title="Espresso">Espresso</a> <ul><li><a href="/wiki/Doppio" title="Doppio">doppio</a></li> <li><a href="/wiki/Lungo" title="Lungo">lungo</a></li> <li><a href="/wiki/Ristretto" title="Ristretto">ristretto</a></li></ul></li> <li><a href="/wiki/Espresso_machine" title="Espresso machine">Espresso machine</a></li> <li><a href="/wiki/French_drip" class="mw-redirect" title="French drip">French drip</a> <ul><li><a href="/wiki/Karlsbad_coffee_maker" class="mw-redirect" title="Karlsbad coffee maker">Karlsbad coffee maker</a></li></ul></li> <li><a href="/wiki/French_press" title="French press">French press</a></li> <li><a href="/wiki/Instant_coffee" title="Instant coffee">Instant coffee</a> <ul><li><a href="/wiki/Coffee_syrup" class="mw-redirect" title="Coffee syrup">Coffee syrup</a></li></ul></li> <li><a href="/wiki/Knockbox" title="Knockbox">Knockbox</a></li> <li><a href="/wiki/Moka_pot" title="Moka pot">Moka pot</a></li> <li><a href="/wiki/Neapolitan_flip_coffee_pot" title="Neapolitan flip coffee pot">Neapolitan flip coffee pot</a></li> <li><a href="/wiki/Coffee_percolator" title="Coffee percolator">Percolator</a></li> <li><a href="/wiki/Turkish_coffee" title="Turkish coffee">Turkish coffee</a></li> <li><a href="/wiki/Vacuum_coffee_maker" title="Vacuum coffee maker">Vacuum maker</a></li> <li><a href="/wiki/Single-serve_coffee_container" title="Single-serve coffee container">Single-serve coffee container</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_coffee_drinks" title="List of coffee drinks">Coffee drinks</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/Affogato" title="Affogato">Affogato</a></li> <li><a href="/wiki/Caff%C3%A8_Americano" class="mw-redirect" title="Caffè Americano">Americano</a></li> <li><a href="/wiki/Beaten_coffee" title="Beaten coffee">Beaten coffee</a></li> <li><a href="/wiki/Bica_(coffee)" title="Bica (coffee)">Bica</a></li> <li><a href="/wiki/Bicerin" title="Bicerin">Bicerin</a></li> <li><a href="/wiki/Black_Russian" title="Black Russian">Black Russian</a></li> <li><a href="/wiki/Vietnamese_iced_coffee" title="Vietnamese iced coffee">Cà phê sữa đá</a></li> <li><a href="/wiki/Caf%C3%A9_au_lait" title="Café au lait">Café au lait</a></li> <li><a href="/wiki/Caf%C3%A9_com_cheirinho" title="Café com cheirinho">Café com cheirinho</a></li> <li><a href="/wiki/Caf%C3%A9_con_leche" title="Café con leche">Café con leche</a></li> <li><a href="/wiki/Caf%C3%A9_de_olla" title="Café de olla">Café de olla</a></li> <li><a href="/wiki/Caf%C3%A9_Touba" title="Café Touba">Café Touba</a></li> <li><a href="/wiki/Caff%C3%A8_corretto" title="Caffè corretto">Caffè corretto</a></li> <li><a href="/wiki/Caff%C3%A8_crema" title="Caffè crema">Caffè crema</a></li> <li><a href="/wiki/Caff%C3%A8_macchiato" title="Caffè macchiato">Caffè macchiato</a></li> <li><a href="/wiki/Caff%C3%A8_mocha" title="Caffè mocha">Caffè mocha</a></li> <li><a href="/wiki/Cappuccino" title="Cappuccino">Cappuccino</a></li> <li><a href="/wiki/Carajillo" title="Carajillo">Carajillo</a></li> <li><a href="/wiki/Coffee_cabinet" title="Coffee cabinet">Coffee cabinet</a></li> <li><a href="/wiki/Coffee_milk" title="Coffee milk">Coffee milk</a></li> <li><a href="/wiki/Cortado" title="Cortado">Cortado</a></li> <li><a href="/wiki/Cuban_espresso" title="Cuban espresso">Café Cubano</a></li> <li><a href="/wiki/Dalgona_coffee" title="Dalgona coffee">Dalgona coffee</a></li> <li><a href="/wiki/Egg_coffee" title="Egg coffee">Egg coffee</a></li> <li><a href="/wiki/Espresso" title="Espresso">Espresso</a></li> <li><a href="/wiki/Flat_white" title="Flat white">Flat white</a></li> <li><a href="/wiki/Frapp%C3%A9_coffee" title="Frappé coffee">Frappé coffee</a></li> <li><a href="/wiki/Frappuccino" title="Frappuccino">Frappuccino</a></li> <li><a href="/wiki/Gal%C3%A3o" title="Galão">Galão</a></li> <li><a href="/wiki/List_of_coffee_drinks#Garoto" title="List of coffee drinks">Garoto</a></li> <li><a href="/wiki/Gassosa_al_caff%C3%A8" title="Gassosa al caffè">Gassosa al caffè</a></li> <li><a href="/wiki/Iced_coffee" title="Iced coffee">Iced coffee</a></li> <li><a href="/wiki/Indian_filter_coffee" title="Indian filter coffee">Indian filter coffee</a></li> <li><a href="/wiki/Ipoh_white_coffee" title="Ipoh white coffee">Ipoh white coffee</a></li> <li><a href="/wiki/Irish_coffee" title="Irish coffee">Irish coffee</a></li> <li><a href="/wiki/Karsk" title="Karsk">Karsk</a></li> <li><a href="/wiki/Kopi_(drink)" title="Kopi (drink)">Kopi</a></li> <li><a href="/wiki/Kopi_luwak" title="Kopi luwak">Kopi luwak</a></li> <li><a href="/wiki/Kopi_tubruk" title="Kopi tubruk">Kopi tubruk</a></li> <li><a href="/wiki/Kurdish_coffee" title="Kurdish coffee">Kurdish coffee</a></li> <li><a href="/wiki/Latte_macchiato" title="Latte macchiato">Latte macchiato</a></li> <li><a href="/wiki/Latte" title="Latte">Latte</a></li> <li><a href="/wiki/Liqueur_coffee" title="Liqueur coffee">Liqueur coffee</a></li> <li><a href="/wiki/Long_black" title="Long black">Long black</a></li> <li><a href="/wiki/Lungo" title="Lungo">Lungo</a></li> <li><a href="/wiki/Marocchino" title="Marocchino">Marocchino</a></li> <li><a href="/wiki/Mazagran_(drink)" title="Mazagran (drink)">Mazagran</a></li> <li><a href="/wiki/Moretta_(coffee)" title="Moretta (coffee)">Moretta</a></li> <li><a href="/wiki/Oliang" title="Oliang">Oliang</a></li> <li><a href="/wiki/Raf_coffee" title="Raf coffee">Raf coffee</a></li> <li><a href="/wiki/List_of_coffee_drinks#Red_eye" title="List of coffee drinks">Red eye</a></li> <li><a href="/wiki/Ristretto" title="Ristretto">Ristretto</a></li> <li><a href="/wiki/R%C3%BCdesheimer_Kaffee" title="Rüdesheimer Kaffee">Rüdesheimer Kaffee</a></li> <li><a href="/wiki/Tenom_coffee" class="mw-redirect" title="Tenom coffee">Tenom coffee</a></li> <li><a href="/wiki/Turkish_coffee" title="Turkish coffee">Turkish coffee</a></li> <li><a href="/wiki/White_coffee" title="White coffee">White coffee</a></li> <li><a href="/wiki/White_Russian_(cocktail)" title="White Russian (cocktail)">White Russian</a></li> <li><a href="/wiki/Wiener_Melange" title="Wiener Melange">Wiener Melange</a></li> <li><a href="/wiki/Yuenyeung" title="Yuenyeung">Yuenyeung</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Organization lists</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/List_of_bakery_caf%C3%A9s" class="mw-redirect" title="List of bakery cafés">Bakery cafés</a></li> <li><a href="/wiki/List_of_coffee_companies" title="List of coffee companies">Coffee companies</a></li> <li><a href="/wiki/List_of_coffeehouse_chains" title="List of coffeehouse chains">Coffeehouses</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Lifestyle</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/Barista" title="Barista">Barista</a></li> <li><a href="/wiki/Bikini_barista" title="Bikini barista">Bikini barista</a></li> <li><a href="/wiki/Caff%C3%A8_sospeso" title="Caffè sospeso">Caffè sospeso</a></li> <li><a href="/wiki/Break_(work)#Coffee_break" title="Break (work)">Coffee break</a></li> <li><a href="/wiki/Coffee_ceremony_of_Ethiopia_and_Eritrea" title="Coffee ceremony of Ethiopia and Eritrea">Coffee ceremony of Ethiopia and Eritrea</a></li> <li><a href="/wiki/CoffeeCon" title="CoffeeCon">CoffeeCon</a></li> <li><a href="/wiki/Coffee_culture" title="Coffee culture">Coffee culture</a></li> <li><a href="/wiki/Coffee_cupping" title="Coffee cupping">Coffee cupping</a></li> <li><a href="/wiki/Coffee_palace" title="Coffee palace">Coffee palace</a></li> <li><a href="/wiki/Coffeehouse" title="Coffeehouse">Coffeehouse</a></li> <li><a href="/wiki/English_coffeehouses_in_the_17th_and_18th_centuries" title="English coffeehouses in the 17th and 18th centuries">Historical coffeehouses</a></li> <li><a href="/wiki/Kopi_tiam" title="Kopi tiam">Kopi tiam</a></li> <li><a href="/wiki/Latte_art" title="Latte art">Latte art</a></li> <li><a href="/wiki/Viennese_coffee_house" class="mw-redirect" title="Viennese coffee house">Viennese coffee house</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Coffee_substitute" title="Coffee substitute">Substitutes</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/Caff%C3%A8_d%27orzo" title="Caffè d'orzo">Barley coffee</a></li> <li><a href="/wiki/Barley_tea" title="Barley tea">Barley tea</a></li> <li><a href="/wiki/Barleycup" title="Barleycup">Barleycup</a></li> <li><a href="/wiki/Caro_(drink)" title="Caro (drink)">Caro</a></li> <li><a href="/wiki/Cereal_coffee" title="Cereal coffee">Cereal coffee</a></li> <li><a href="/wiki/Chicory" title="Chicory">Chicory</a></li> <li><a href="/wiki/Dandelion_coffee" title="Dandelion coffee">Dandelion coffee</a></li> <li><a href="/wiki/Inka_(drink)" title="Inka (drink)">Inka</a></li> <li><a href="/wiki/Brosimum_alicastrum" title="Brosimum alicastrum">Maya nut</a></li> <li><a href="/wiki/Postum" title="Postum">Postum</a></li> <li><a href="/wiki/Qishr" title="Qishr">Qishr</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Serving vessels</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/Coffee_cup" title="Coffee cup">Coffee cup</a> <ul><li><a href="/wiki/Coffee_cup_sleeve" title="Coffee cup sleeve">sleeve</a></li></ul></li> <li><a href="/wiki/Cezve" title="Cezve">Cezve</a></li> <li><a href="/wiki/Demitasse" title="Demitasse">Demitasse</a> <ul><li><a href="/wiki/Demitasse_spoon" title="Demitasse spoon">spoon</a></li></ul></li> <li><a href="/wiki/Tasse_%C3%A0_caf%C3%A9" title="Tasse à café">Tasse à café</a></li> <li><a href="/wiki/Zarf" title="Zarf">Zarf</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Competitions</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/United_States_Barista_Championship" title="United States Barista Championship">United States Barista Championship</a></li> <li><a href="/wiki/World_Barista_Championship" title="World Barista Championship">World Barista Championship</a></li> <li><a href="/wiki/World_Brewers_Cup" title="World Brewers Cup">World Brewers Cup</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Misc.</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/Coffee_and_doughnuts" title="Coffee and doughnuts">Coffee and doughnuts</a></li> <li><a href="/wiki/Coffee_bag" title="Coffee bag">Coffee bag</a></li> <li><a href="/wiki/Coffee_service" title="Coffee service">Coffee service</a></li> <li><a href="/wiki/Coffee_leaf_rust" class="mw-redirect" title="Coffee leaf rust">Coffee leaf rust</a></li> <li><a href="/wiki/Coffee_wars" title="Coffee wars">Coffee wars</a></li> <li><a href="/wiki/Gustav_III_of_Sweden%27s_coffee_experiment" title="Gustav III of Sweden's coffee experiment">Gustav III of Sweden's coffee experiment</a></li> <li><a href="/wiki/Canned_coffee" title="Canned coffee">Canned coffee</a></li> <li><a href="/wiki/Coffee_vending_machine" title="Coffee vending machine">Coffee vending machine</a></li> <li><a href="/wiki/Used_coffee_grounds" title="Used coffee grounds">Used coffee grounds</a></li> <li><a href="/wiki/Sustainable_coffee" title="Sustainable coffee">Sustainable coffee</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><span class="nowrap"><span class="noviewer" typeof="mw:File"><a href="/wiki/File:Emblem-relax.svg" class="mw-file-description"><img alt="icon" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/05/Emblem-relax.svg/16px-Emblem-relax.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/05/Emblem-relax.svg/24px-Emblem-relax.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/05/Emblem-relax.svg/32px-Emblem-relax.svg.png 2x" data-file-width="60" data-file-height="60" /></a></span> </span><a href="/wiki/Portal:Coffee" title="Portal:Coffee">Coffee portal</a></li> <li><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/23px-Symbol_category_class.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/31px-Symbol_category_class.svg.png 2x" data-file-width="180" data-file-height="185" /></span></span> <a href="/wiki/Category:Coffee" title="Category:Coffee">Category: Coffee</a></li></ul> </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="Types_of_hydroxycinnamic_acids" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Hydroxycinnamic_acid" title="Template:Hydroxycinnamic acid"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Hydroxycinnamic_acid" title="Template talk:Hydroxycinnamic acid"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Hydroxycinnamic_acid" title="Special:EditPage/Template:Hydroxycinnamic acid"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Types_of_hydroxycinnamic_acids" style="font-size:114%;margin:0 4em">Types of <a href="/wiki/Hydroxycinnamic_acid" title="Hydroxycinnamic acid">hydroxycinnamic acids</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Aglycones</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%">Precursor</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/Cinnamic_acid" title="Cinnamic acid">Cinnamic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Monohydroxycinnamic acids<br />(Coumaric acids)</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/P-Coumaric_acid" title="P-Coumaric acid"><i>p</i>-Coumaric acid</a></li> <li><a href="/wiki/O-Coumaric_acid" title="O-Coumaric acid"><i>o</i>-Coumaric acid</a></li> <li><a href="/wiki/M-Coumaric_acid" title="M-Coumaric acid"><i>m</i>-Coumaric acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Dihydroxycinnamic_acid" title="Dihydroxycinnamic acid">Dihydroxycinnamic acids</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a class="mw-selflink selflink">Caffeic acid</a> (3,4-dihydroxycinnamic acid)</li> <li><a href="/wiki/Umbellic_acid" title="Umbellic acid">Umbellic acid</a> (2,4-dihydroxycinnamic acid)</li> <li><a href="/wiki/2,3-Dihydroxycinnamic_acid" title="2,3-Dihydroxycinnamic acid">2,3-Dihydroxycinnamic acid</a></li> <li><a href="/wiki/2,5-Dihydroxycinnamic_acid" title="2,5-Dihydroxycinnamic acid">2,5-Dihydroxycinnamic acid</a></li> <li><a href="/wiki/3,5-Dihydroxycinnamic_acid" title="3,5-Dihydroxycinnamic acid">3,5-Dihydroxycinnamic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Trihydroxycinnamic acids</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/2,4,5-Trihydroxycinnamic_acid" title="2,4,5-Trihydroxycinnamic acid">2,4,5-Trihydroxycinnamic acid</a></li> <li><a href="/w/index.php?title=3,4,5-Trihydroxycinnamic_acid&action=edit&redlink=1" class="new" title="3,4,5-Trihydroxycinnamic acid (page does not exist)">3,4,5-Trihydroxycinnamic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i>O</i>-methylated forms</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/Ferulic_acid" title="Ferulic acid">Ferulic acid</a></li> <li><a href="/wiki/5-Hydroxyferulic_acid" title="5-Hydroxyferulic acid">5-Hydroxyferulic acid</a></li> <li><a href="/wiki/Isoferulic_acid" title="Isoferulic acid">Isoferulic acid</a></li> <li><a href="/wiki/Sinapinic_acid" title="Sinapinic acid">Sinapinic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">others</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/Plicatin_A" title="Plicatin A">Plicatin A</a></li> <li><a href="/wiki/Plicatin_B" title="Plicatin B">Plicatin B</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Esters</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%">glycoside-likes</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%">Esters of<br />caffeic acid<br />with cyclitols</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%">esters of<br /><a href="/wiki/Quinic_acid" title="Quinic acid">quinic acid</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/Chlorogenic_acid" title="Chlorogenic acid">Chlorogenic acid</a> (3-caffeoylquinic acid)</li> <li><a href="/w/index.php?title=Cryptochlorogenic_acid&action=edit&redlink=1" class="new" title="Cryptochlorogenic acid (page does not exist)">Cryptochlorogenic acid</a> (4-<i>O</i>-caffeoylquinic acid)</li> <li><a href="/wiki/Neochlorogenic_acid" title="Neochlorogenic acid">Neochlorogenic acid</a> (5-<i>O</i>-Caffeoylquinic acid)</li> <li><a href="/wiki/Cynarine" title="Cynarine">Cynarine</a> (1,5-dicaffeoylquinic acid)</li> <li><a href="/w/index.php?title=3,4-dicaffeoylquinic_acid&action=edit&redlink=1" class="new" title="3,4-dicaffeoylquinic acid (page does not exist)">3,4-dicaffeoylquinic acid</a></li> <li><a href="/w/index.php?title=3,5-dicaffeoylquinic_acid&action=edit&redlink=1" class="new" title="3,5-dicaffeoylquinic acid (page does not exist)">3,5-dicaffeoylquinic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">esters of<br /><a href="/wiki/Shikimic_acid" title="Shikimic acid">shikimic acid</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/Dactylifric_acid" title="Dactylifric acid">Dactylifric acid</a> (3-<i>O</i>-caffeoylshikimic acid)</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Glycosides</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="/w/index.php?title=Ferulic_acid_glucoside&action=edit&redlink=1" class="new" title="Ferulic acid glucoside (page does not exist)">Ferulic acid glucoside</a></li> <li><a href="/wiki/P-Coumaric_acid_glucoside" title="P-Coumaric acid glucoside"><i>p</i>-Coumaric acid glucoside</a></li> <li><a href="/w/index.php?title=1-Sinapoyl-D-glucose&action=edit&redlink=1" class="new" title="1-Sinapoyl-D-glucose (page does not exist)">1-Sinapoyl-<small>D</small>-glucose</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/Tartaric_acid" title="Tartaric acid">Tartaric acid</a> esters</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/Caftaric_acid" title="Caftaric acid">Caftaric acid</a></li> <li><a href="/wiki/Chicoric_acid" title="Chicoric acid">Chicoric acid</a> (dicaffeoyltartaric acid)</li> <li><a href="/wiki/Coutaric_acid" title="Coutaric acid">Coutaric acid</a></li> <li><a href="/wiki/Fertaric_acid" title="Fertaric acid">Fertaric acid</a></li> <li><a href="/wiki/Grape_reaction_product" title="Grape reaction product">Grape reaction product</a> (caftaric acid conjugated with glutathione)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other esters<br />with caffeic acid</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/Caffeoylmalic_acid" title="Caffeoylmalic acid">Caffeoylmalic acid</a></li> <li><a href="/wiki/Ethyl_caffeate" title="Ethyl caffeate">Ethyl caffeate</a></li> <li><a href="/wiki/Methyl_caffeate" title="Methyl caffeate">Methyl caffeate</a></li> <li><a href="/wiki/Caffeic_acid_phenethyl_ester" title="Caffeic acid phenethyl ester">Caffeic acid phenethyl ester</a> (CAPE)</li> <li><a href="/wiki/Rosmarinic_acid" title="Rosmarinic acid">Rosmarinic acid</a> (ester with 3,4-dihydroxyphenyllactic acid)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Caffeoyl phenylethanoid<br /> glycoside (CPG)</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/Echinacoside" title="Echinacoside">Echinacoside</a></li> <li><a href="/w/index.php?title=Calceolarioside_A&action=edit&redlink=1" class="new" title="Calceolarioside A (page does not exist)">Calceolarioside A</a>, <a href="/w/index.php?title=Calceolarioside_B&action=edit&redlink=1" class="new" title="Calceolarioside B (page does not exist)">B</a>, <a href="/w/index.php?title=Calceolarioside_C&action=edit&redlink=1" class="new" title="Calceolarioside C (page does not exist)">C</a>, <a href="/w/index.php?title=Calceolarioside_F&action=edit&redlink=1" class="new" title="Calceolarioside F (page does not exist)">F</a></li> <li><a href="/w/index.php?title=Chiritoside_A&action=edit&redlink=1" class="new" title="Chiritoside A (page does not exist)">Chiritoside A</a>, <a href="/w/index.php?title=Chiritoside_B&action=edit&redlink=1" class="new" title="Chiritoside B (page does not exist)">B</a>, <a href="/w/index.php?title=Chiritoside_C&action=edit&redlink=1" class="new" title="Chiritoside C (page does not exist)">C</a></li> <li><a href="/w/index.php?title=Cistanoside_A&action=edit&redlink=1" class="new" title="Cistanoside A (page does not exist)">Cistanoside A</a>, <a href="/w/index.php?title=Cistanoside_B&action=edit&redlink=1" class="new" title="Cistanoside B (page does not exist)">B</a>, <a href="/w/index.php?title=Cistanoside_C&action=edit&redlink=1" class="new" title="Cistanoside C (page does not exist)">C</a>, <a href="/w/index.php?title=Cistanoside_D&action=edit&redlink=1" class="new" title="Cistanoside D (page does not exist)">D</a>, <a href="/w/index.php?title=Cistanoside_E&action=edit&redlink=1" class="new" title="Cistanoside E (page does not exist)">E</a>, <a href="/w/index.php?title=Cistanoside_F&action=edit&redlink=1" class="new" title="Cistanoside F (page does not exist)">F</a>, <a href="/w/index.php?title=Cistanoside_G&action=edit&redlink=1" class="new" title="Cistanoside G (page does not exist)">G</a>, <a href="/w/index.php?title=Cistanoside_H&action=edit&redlink=1" class="new" title="Cistanoside H (page does not exist)">H</a></li> <li><a href="/w/index.php?title=Conandroside&action=edit&redlink=1" class="new" title="Conandroside (page does not exist)">Conandroside</a></li> <li><a href="/w/index.php?title=Myconoside&action=edit&redlink=1" class="new" title="Myconoside (page does not exist)">Myconoside</a></li> <li><a href="/w/index.php?title=Pauoifloside&action=edit&redlink=1" class="new" title="Pauoifloside (page does not exist)">Pauoifloside</a></li> <li><a href="/w/index.php?title=Plantainoside_A&action=edit&redlink=1" class="new" title="Plantainoside A (page does not exist)">Plantainoside A</a></li> <li><a href="/w/index.php?title=Plantamajoside&action=edit&redlink=1" class="new" title="Plantamajoside (page does not exist)">Plantamajoside</a></li> <li><a href="/w/index.php?title=Tubuloside_B&action=edit&redlink=1" class="new" title="Tubuloside B (page does not exist)">Tubuloside B</a></li> <li><a href="/wiki/Verbascoside" title="Verbascoside">Verbascoside</a> (<a href="/w/index.php?title=Isoverbascoside&action=edit&redlink=1" class="new" title="Isoverbascoside (page does not exist)">Isoverbascoside</a>, <a href="/w/index.php?title=2%27-Acetylverbascoside&action=edit&redlink=1" class="new" title="2'-Acetylverbascoside (page does not exist)">2′-Acetylverbascoside</a>)</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Oligomeric forms</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Dimers</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/Diferulic_acids" title="Diferulic acids">Diferulic acids</a> (DiFA) : <a href="/w/index.php?title=5,5%27-Diferulic_acid&action=edit&redlink=1" class="new" title="5,5'-Diferulic acid (page does not exist)">5,5′-Diferulic acid</a>, <a href="/w/index.php?title=8-O-4%27-Diferulic_acid&action=edit&redlink=1" class="new" title="8-O-4'-Diferulic acid (page does not exist)">8-<i>O</i>-4′-Diferulic acid</a>, <a href="/wiki/8,5%27-Diferulic_acid" title="8,5'-Diferulic acid">8,5′-Diferulic acid</a>, <a href="/wiki/8,5%27-DiFA_(DC)" class="mw-redirect" title="8,5'-DiFA (DC)">8,5′-DiFA (DC)</a>, <a href="/w/index.php?title=8,5%27-DiFA_(BF)&action=edit&redlink=1" class="new" title="8,5'-DiFA (BF) (page does not exist)">8,5′-DiFA (BF)</a>, <a href="/w/index.php?title=8,8%27-Diferulic_acid&action=edit&redlink=1" class="new" title="8,8'-Diferulic acid (page does not exist)">8,8′-Diferulic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Trimers</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/Triferulic_acid" title="Triferulic acid">Triferulic acids</a> : <a href="/w/index.php?title=5-5%27,8%27-O-4%22-Triferulic_acid&action=edit&redlink=1" class="new" title="5-5',8'-O-4"-Triferulic acid (page does not exist)">5-5′,8′-<i>O</i>-4″-Triferulic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Tetramers</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="/w/index.php?title=Tetraferulic_acid&action=edit&redlink=1" class="new" title="Tetraferulic acid (page does not exist)">Tetraferulic acids</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Conjugates with<br /><a href="/wiki/Coenzyme_A" title="Coenzyme A">coenzyme A</a> (CoA)</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="/w/index.php?title=Caffeoyl-CoA&action=edit&redlink=1" class="new" title="Caffeoyl-CoA (page does not exist)">Caffeoyl-CoA</a></li> <li><a href="/wiki/Cinnamoyl-CoA" title="Cinnamoyl-CoA">Cinnamoyl-CoA</a></li> <li><a href="/wiki/Coumaroyl-CoA" title="Coumaroyl-CoA">Coumaroyl-CoA</a></li></ul> </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="Leukotriene_signaling_modulators" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Leukotriene_signaling_modulators" title="Template:Leukotriene signaling modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Leukotriene_signaling_modulators" title="Template talk:Leukotriene signaling modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Leukotriene_signaling_modulators" title="Special:EditPage/Template:Leukotriene signaling modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Leukotriene_signaling_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Leukotriene" title="Leukotriene">Leukotriene</a> <a href="/wiki/Cell_signaling" title="Cell signaling">signaling</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Receptor_(biochemistry)" title="Receptor (biochemistry)">Receptor</a><br /><small>(<a href="/wiki/Ligand_(biochemistry)" title="Ligand (biochemistry)">ligands</a>)</small></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:4em;;text-align:center;"><a href="/wiki/Leukotriene_B4_receptor" title="Leukotriene B4 receptor"><abbr title="Leukotriene B4 receptor">BLT</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Leukotriene B4 receptor</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="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:4em;;text-align:center;"><a href="/wiki/Leukotriene_B4_receptor_1" title="Leukotriene B4 receptor 1"><abbr title="Leukotriene B4 receptor 1">BLT<sub>1</sub></abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Leukotriene B4 receptor 1</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/wiki/12-Hydroxyeicosatetraenoic_acid" title="12-Hydroxyeicosatetraenoic acid">12-HETE</a></li> <li><a href="/w/index.php?title=20-Hydroxy-LTB4&action=edit&redlink=1" class="new" title="20-Hydroxy-LTB4 (page does not exist)">20-Hydroxy-LTB<sub>4</sub></a></li> <li><a href="/wiki/Leukotriene_B4" title="Leukotriene B4">Leukotriene B<sub>4</sub></a></li> <li><a href="/w/index.php?title=LY-255283&action=edit&redlink=1" class="new" title="LY-255283 (page does not exist)">LY-255283</a></li></ul> <ul><li><b>Antagonists:</b> <a href="/w/index.php?title=20-Carboxy-LTB4&action=edit&redlink=1" class="new" title="20-Carboxy-LTB4 (page does not exist)">20-Carboxy-LTB<sub>4</sub></a></li> <li><a href="/w/index.php?title=Amelubant&action=edit&redlink=1" class="new" title="Amelubant (page does not exist)">Amelubant</a></li> <li><a href="/w/index.php?title=CGS-23131&action=edit&redlink=1" class="new" title="CGS-23131 (page does not exist)">CGS-23131 (LY-223982)</a></li> <li><a href="/w/index.php?title=CGS-25019C&action=edit&redlink=1" class="new" title="CGS-25019C (page does not exist)">CGS-25019C</a></li> <li><a href="/w/index.php?title=CP-105696&action=edit&redlink=1" class="new" title="CP-105696 (page does not exist)">CP-105696</a></li> <li><a href="/w/index.php?title=CP-195543&action=edit&redlink=1" class="new" title="CP-195543 (page does not exist)">CP-195543</a></li> <li><a href="/wiki/Etalocib" title="Etalocib">Etalocib</a></li> <li><a href="/w/index.php?title=LY-293111&action=edit&redlink=1" class="new" title="LY-293111 (page does not exist)">LY-293111</a></li> <li><a href="/w/index.php?title=Moxilubant&action=edit&redlink=1" class="new" title="Moxilubant (page does not exist)">Moxilubant</a></li> <li><a href="/w/index.php?title=ONO-4057&action=edit&redlink=1" class="new" title="ONO-4057 (page does not exist)">ONO-4057</a></li> <li><a href="/w/index.php?title=RG-14893&action=edit&redlink=1" class="new" title="RG-14893 (page does not exist)">RG-14893</a></li> <li><a href="/w/index.php?title=RP-69698&action=edit&redlink=1" class="new" title="RP-69698 (page does not exist)">RP-69698</a></li> <li><a href="/w/index.php?title=SB-209247&action=edit&redlink=1" class="new" title="SB-209247 (page does not exist)">SB-209247</a></li> <li><a href="/w/index.php?title=SC-53228&action=edit&redlink=1" class="new" title="SC-53228 (page does not exist)">SC-53228</a></li> <li><a href="/w/index.php?title=Ticolubant&action=edit&redlink=1" class="new" title="Ticolubant (page does not exist)">Ticolubant</a></li> <li><a href="/w/index.php?title=U-75302&action=edit&redlink=1" class="new" title="U-75302 (page does not exist)">U-75302</a></li> <li><a href="/w/index.php?title=ZK-158252&action=edit&redlink=1" class="new" title="ZK-158252 (page does not exist)">ZK-158252</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Leukotriene_B4_receptor_2" title="Leukotriene B4 receptor 2"><abbr title="Leukotriene B4 receptor 2">BLT<sub>2</sub></abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Leukotriene B4 receptor 2</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/wiki/12-Hydroxyeicosatetraenoic_acid" title="12-Hydroxyeicosatetraenoic acid">12-HETE</a></li> <li><a href="/wiki/12-Hydroxyheptadecatrienoic_acid" title="12-Hydroxyheptadecatrienoic acid">12-HHT</a></li> <li><a href="/w/index.php?title=12-Hydroperoxy-5Z,8Z,10E,14Z-eicosatetraenoic_acid&action=edit&redlink=1" class="new" title="12-Hydroperoxy-5Z,8Z,10E,14Z-eicosatetraenoic acid (page does not exist)">12-HpETE</a></li> <li><a href="/wiki/15-Hydroxyicosatetraenoic_acid" class="mw-redirect" title="15-Hydroxyicosatetraenoic acid">15-HETE</a></li> <li><a href="/w/index.php?title=15-Hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic_acid&action=edit&redlink=1" class="new" title="15-Hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic acid (page does not exist)">15-HpETE</a></li> <li><a href="/w/index.php?title=20-Hydroxy-LTB4&action=edit&redlink=1" class="new" title="20-Hydroxy-LTB4 (page does not exist)">20-Hydroxy-LTB<sub>4</sub></a></li> <li><a href="/wiki/Leukotriene_B4" title="Leukotriene B4">Leukotriene B<sub>4</sub></a></li></ul> <ul><li><b>Antagonists:</b> <a href="/w/index.php?title=CP-195543&action=edit&redlink=1" class="new" title="CP-195543 (page does not exist)">CP-195543</a></li> <li><a href="/w/index.php?title=LY-255283&action=edit&redlink=1" class="new" title="LY-255283 (page does not exist)">LY-255283</a></li> <li><a href="/w/index.php?title=ZK-158252&action=edit&redlink=1" class="new" title="ZK-158252 (page does not exist)">ZK-158252</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Cysteinyl_leukotriene_receptor" title="Cysteinyl leukotriene receptor"><abbr title="Cysteinyl leukotriene receptor">CysLT</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Cysteinyl leukotriene receptor</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="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:4em;;text-align:center;"><a href="/wiki/Cysteinyl_leukotriene_receptor_1" title="Cysteinyl leukotriene receptor 1"><abbr title="Cysteinyl leukotriene receptor 1">CysLT<sub>1</sub></abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Cysteinyl leukotriene receptor 1</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/wiki/Leukotriene_C4" title="Leukotriene C4">Leukotriene C<sub>4</sub></a></li> <li><a href="/wiki/Leukotriene_D4" title="Leukotriene D4">Leukotriene D<sub>4</sub></a></li> <li><a href="/wiki/Leukotriene_E4" title="Leukotriene E4">Leukotriene E<sub>4</sub></a></li></ul> <ul><li><b>Antagonists:</b> <a href="/wiki/Ablukast" title="Ablukast">Ablukast</a></li> <li><a href="/w/index.php?title=BAYu9773&action=edit&redlink=1" class="new" title="BAYu9773 (page does not exist)">BAYu9773</a></li> <li><a href="/w/index.php?title=BAYu9916&action=edit&redlink=1" class="new" title="BAYu9916 (page does not exist)">BAYu9916</a></li> <li><a href="/w/index.php?title=BAYx7195&action=edit&redlink=1" class="new" title="BAYx7195 (page does not exist)">BAYx7195</a></li> <li><a href="/w/index.php?title=Cinalukast&action=edit&redlink=1" class="new" title="Cinalukast (page does not exist)">Cinalukast</a></li> <li><a href="/w/index.php?title=FPL-55712&action=edit&redlink=1" class="new" title="FPL-55712 (page does not exist)">FPL-55712</a></li> <li><a href="/w/index.php?title=ICI-198615&action=edit&redlink=1" class="new" title="ICI-198615 (page does not exist)">ICI-198615</a></li> <li><a href="/w/index.php?title=Iralukast&action=edit&redlink=1" class="new" title="Iralukast (page does not exist)">Iralukast</a></li> <li><a href="/w/index.php?title=LY-170680&action=edit&redlink=1" class="new" title="LY-170680 (page does not exist)">LY-170680</a></li> <li><a href="/w/index.php?title=Masilukast&action=edit&redlink=1" class="new" title="Masilukast (page does not exist)">Masilukast</a></li> <li><a href="/w/index.php?title=MK-571&action=edit&redlink=1" class="new" title="MK-571 (page does not exist)">MK-571</a></li> <li><a href="/wiki/Montelukast" title="Montelukast">Montelukast</a></li> <li><a href="/w/index.php?title=ONO-1078&action=edit&redlink=1" class="new" title="ONO-1078 (page does not exist)">ONO-1078</a></li> <li><a href="/w/index.php?title=Pobilukast&action=edit&redlink=1" class="new" title="Pobilukast (page does not exist)">Pobilukast</a></li> <li><a href="/wiki/Pranlukast" title="Pranlukast">Pranlukast</a></li> <li><a href="/w/index.php?title=Ritolukast&action=edit&redlink=1" class="new" title="Ritolukast (page does not exist)">Ritolukast</a></li> <li><a href="/w/index.php?title=SKF-104353&action=edit&redlink=1" class="new" title="SKF-104353 (page does not exist)">SKF-104353</a></li> <li><a href="/w/index.php?title=SR-2640&action=edit&redlink=1" class="new" title="SR-2640 (page does not exist)">SR-2640</a></li> <li><a href="/w/index.php?title=Sulukast&action=edit&redlink=1" class="new" title="Sulukast (page does not exist)">Sulukast</a></li> <li><a href="/wiki/Tipelukast" title="Tipelukast">Tipelukast</a></li> <li><a href="/w/index.php?title=Tomelukast&action=edit&redlink=1" class="new" title="Tomelukast (page does not exist)">Tomelukast</a></li> <li><a href="/w/index.php?title=Verlukast&action=edit&redlink=1" class="new" title="Verlukast (page does not exist)">Verlukast</a></li> <li><a href="/wiki/Zafirlukast" title="Zafirlukast">Zafirlukast</a></li> <li><a href="/w/index.php?title=ZD-3523&action=edit&redlink=1" class="new" title="ZD-3523 (page does not exist)">ZD-3523</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Cysteinyl_leukotriene_receptor_2" title="Cysteinyl leukotriene receptor 2"><abbr title="Cysteinyl leukotriene receptor 2">CysLT<sub>2</sub></abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Cysteinyl leukotriene receptor 2</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/wiki/Leukotriene_C4" title="Leukotriene C4">Leukotriene C<sub>4</sub></a></li> <li><a href="/wiki/Leukotriene_D4" title="Leukotriene D4">Leukotriene D<sub>4</sub></a></li> <li><a href="/wiki/Leukotriene_E4" title="Leukotriene E4">Leukotriene E<sub>4</sub></a></li></ul> <ul><li><b>Antagonists:</b> <a href="/w/index.php?title=BAYu9773&action=edit&redlink=1" class="new" title="BAYu9773 (page does not exist)">BAYu9773</a></li> <li><a href="/w/index.php?title=BAYu9916&action=edit&redlink=1" class="new" title="BAYu9916 (page does not exist)">BAYu9916</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Cysteinyl_leukotriene_receptor_E" class="mw-redirect" title="Cysteinyl leukotriene receptor E"><abbr title="Cysteinyl leukotriene receptor E">CysLT<sub>E</sub></abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Cysteinyl leukotriene receptor E</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/wiki/Leukotriene_E4" title="Leukotriene E4">Leukotriene E<sub>4</sub></a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Enzyme" title="Enzyme">Enzyme</a><br /><small>(<a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">inhibitors</a>)</small></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:4em;;text-align:center;"><a href="/wiki/Arachidonate_5-lipoxygenase" title="Arachidonate 5-lipoxygenase"><abbr title="Arachidonate 5-lipoxygenase">5-LOX</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Arachidonate 5-lipoxygenase</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=2-TEDC&action=edit&redlink=1" class="new" title="2-TEDC (page does not exist)">2-TEDC</a></li> <li><a href="/wiki/Baicalein" title="Baicalein">Baicalein</a></li> <li><a href="/w/index.php?title=BW-A4C&action=edit&redlink=1" class="new" title="BW-A4C (page does not exist)">BW-A4C</a></li> <li><a href="/w/index.php?title=BW-B70C&action=edit&redlink=1" class="new" title="BW-B70C (page does not exist)">BW-B70C</a></li> <li><a class="mw-selflink selflink">Caffeic acid</a></li> <li><a href="/w/index.php?title=Cinnamyl-3,4-dihydroxy-%CE%B1-cyanocinnamate&action=edit&redlink=1" class="new" title="Cinnamyl-3,4-dihydroxy-α-cyanocinnamate (page does not exist)">CDC</a></li> <li><a href="/w/index.php?title=CJ-13610&action=edit&redlink=1" class="new" title="CJ-13610 (page does not exist)">CJ-13610</a></li> <li><a href="/wiki/Curcumin" title="Curcumin">Curcumin</a></li> <li><a href="/wiki/Fenleuton" title="Fenleuton">Fenleuton</a></li> <li><a href="/wiki/Hyperforin" title="Hyperforin">Hyperforin</a></li> <li><a href="/wiki/Hypericum_perforatum" title="Hypericum perforatum"><i>Hypericum perforatum</i> (St. John's Wort)</a></li> <li><a href="/wiki/Meclofenamic_acid" title="Meclofenamic acid">Meclofenamic acid (meclofenamate)</a></li> <li><a href="/wiki/Minocycline" title="Minocycline">Minocycline</a></li> <li><a href="/w/index.php?title=N-Stearoyldopamine&action=edit&redlink=1" class="new" title="N-Stearoyldopamine (page does not exist)">N-Stearoyldopamine</a></li> <li><a href="/w/index.php?title=Timegadine&action=edit&redlink=1" class="new" title="Timegadine (page does not exist)">Timegadine</a></li> <li><a href="/wiki/Zileuton" title="Zileuton">Zileuton</a></li></ul> <ul><li><b><a href="/wiki/Arachidonate_5-lipoxygenase-activating_protein" class="mw-redirect" title="Arachidonate 5-lipoxygenase-activating protein"><abbr title="Arachidonate 5-lipoxygenase-activating protein">FLAP</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Arachidonate 5-lipoxygenase-activating protein</span> inhibitors:</b> <a href="/w/index.php?title=AM-103_(drug)&action=edit&redlink=1" class="new" title="AM-103 (drug) (page does not exist)">AM-103</a></li> <li><a href="/wiki/AM-679_(FLAP_inhibitor)" title="AM-679 (FLAP inhibitor)">AM-679</a></li> <li><a href="/w/index.php?title=BAYx1005&action=edit&redlink=1" class="new" title="BAYx1005 (page does not exist)">BAYx1005</a></li> <li><a href="/w/index.php?title=MK-591&action=edit&redlink=1" class="new" title="MK-591 (page does not exist)">MK-591</a></li> <li><a href="/wiki/MK-886" title="MK-886">MK-886</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Arachidonate_12-lipoxygenase" class="mw-redirect" title="Arachidonate 12-lipoxygenase"><abbr title="Arachidonate 12-lipoxygenase">12-LOX</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Arachidonate 12-lipoxygenase</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=2-TEDC&action=edit&redlink=1" class="new" title="2-TEDC (page does not exist)">2-TEDC</a></li> <li><a href="/w/index.php?title=3-Methoxytropolone&action=edit&redlink=1" class="new" title="3-Methoxytropolone (page does not exist)">3-Methoxytropolone</a></li> <li><a href="/wiki/Baicalein" title="Baicalein">Baicalein</a></li> <li><a href="/w/index.php?title=Cinnamyl-3,4-dihydroxy-%CE%B1-cyanocinnamate&action=edit&redlink=1" class="new" title="Cinnamyl-3,4-dihydroxy-α-cyanocinnamate (page does not exist)">CDC</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Arachidonate_15-lipoxygenase" class="mw-redirect" title="Arachidonate 15-lipoxygenase"><abbr title="Arachidonate 15-lipoxygenase">15-LOX</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Arachidonate 15-lipoxygenase</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=2-TEDC&action=edit&redlink=1" class="new" title="2-TEDC (page does not exist)">2-TEDC</a></li> <li><a href="/w/index.php?title=Cinnamyl-3,4-dihydroxy-%CE%B1-cyanocinnamate&action=edit&redlink=1" class="new" title="Cinnamyl-3,4-dihydroxy-α-cyanocinnamate (page does not exist)">CDC</a></li> <li><a href="/wiki/Luteolin" title="Luteolin">Luteolin</a></li> <li><a href="/w/index.php?title=PD-146176&action=edit&redlink=1" class="new" title="PD-146176 (page does not exist)">PD-146176</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Leukotriene_A4_hydrolase" class="mw-redirect" title="Leukotriene A4 hydrolase"><abbr title="Leukotriene A4 hydrolase">LTA<sub>4</sub>H</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Leukotriene A4 hydrolase</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Acebilustat&action=edit&redlink=1" class="new" title="Acebilustat (page does not exist)">Acebilustat</a></li> <li><a href="/wiki/Captopril" title="Captopril">Captopril</a></li> <li><a href="/w/index.php?title=DG-051&action=edit&redlink=1" class="new" title="DG-051 (page does not exist)">DG-051</a></li> <li><a href="/wiki/Fosinoprilat" class="mw-redirect" title="Fosinoprilat">Fosinoprilat</a></li> <li><a href="/w/index.php?title=JNJ-26993135&action=edit&redlink=1" class="new" title="JNJ-26993135 (page does not exist)">JNJ-26993135</a></li> <li><a href="/w/index.php?title=SA-6541&action=edit&redlink=1" class="new" title="SA-6541 (page does not exist)">SA-6541</a></li> <li><a href="/w/index.php?title=SC-57461A&action=edit&redlink=1" class="new" title="SC-57461A (page does not exist)">SC-57461A</a></li> <li><a href="/wiki/Ubenimex" title="Ubenimex">Ubenimex (bestatin)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Leukotriene_B4_%CF%89-hydroxylase" class="mw-redirect" title="Leukotriene B4 ω-hydroxylase"><abbr title="Leukotriene B4 ω-hydroxylase">LTB<sub>4</sub>H</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Leukotriene B4 ω-hydroxylase</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=17-Octadecynoic_acid&action=edit&redlink=1" class="new" title="17-Octadecynoic acid (page does not exist)">17-Octadecynoic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Leukotriene_C4_synthase" title="Leukotriene C4 synthase"><abbr title="Leukotriene C4 synthase">LTC<sub>4</sub>S</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Leukotriene C4 synthase</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Azelastine" title="Azelastine">Azelastine</a></li> <li><a href="/wiki/MK-886" title="MK-886">MK-886</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Leukotriene_C4_hydrolase" title="Leukotriene C4 hydrolase"><abbr title="Leukotriene C4 hydrolase">LTC<sub>4</sub>H</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Leukotriene C4 hydrolase</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acivicin" title="Acivicin">Acivicin</a></li> <li><a href="/w/index.php?title=Serine-borate_complex&action=edit&redlink=1" class="new" title="Serine-borate complex (page does not exist)">Serine-borate complex</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Leukotriene_D4_hydrolase" class="mw-redirect" title="Leukotriene D4 hydrolase"><abbr title="Leukotriene D4 hydrolase">LTD<sub>4</sub></abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Leukotriene D4 hydrolase</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cilastatin" title="Cilastatin">Cilastatin</a></li> <li><a href="/wiki/Ubenimex" title="Ubenimex">Ubenimex (bestatin)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Others</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><b>Precursors:</b> <a href="/wiki/Linoleic_acid" title="Linoleic acid">Linoleic acid</a></li> <li><a href="/wiki/Gamma-Linolenic_acid" class="mw-redirect" title="Gamma-Linolenic acid">γ-Linolenic acid (gamolenic acid)</a></li> <li><a href="/wiki/Dihomo-%CE%B3-linolenic_acid" title="Dihomo-γ-linolenic acid">Dihomo-γ-linolenic acid</a></li> <li><a href="/wiki/Diglyceride" title="Diglyceride">Diacylglycerol</a></li> <li><a href="/wiki/Arachidonic_acid" title="Arachidonic acid">Arachidonic acid</a></li> <li><a href="/wiki/Arachidonic_acid_5-hydroperoxide" title="Arachidonic acid 5-hydroperoxide">5-HPETE (arachidonic acid 5-hydroperoxide)</a></li> <li><a href="/wiki/Leukotriene_A4" title="Leukotriene A4">Leukotriene A<sub>4</sub></a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><i><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></i></dd> <dd><i><a href="/wiki/Template:Prostanoid_signaling_modulators" title="Template:Prostanoid signaling modulators">Prostanoid signaling modulators</a></i></dd></dl> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Purine_receptor_modulators" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><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:Purine_receptor_modulators" title="Template:Purine receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Purine_receptor_modulators" title="Template talk:Purine receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Purine_receptor_modulators" title="Special:EditPage/Template:Purine receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Purine_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Purine_receptor" class="mw-redirect" title="Purine receptor">Purine receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Receptor_(biochemistry)" title="Receptor (biochemistry)">Receptor</a><br /><small>(<a href="/wiki/Ligand_(biochemistry)" title="Ligand (biochemistry)">ligands</a>)</small></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:6em;;text-align:center;"><a href="/wiki/P0_receptor" class="mw-redirect" title="P0 receptor">P0</a> (<a href="/wiki/Adenine" title="Adenine">adenine</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/w/index.php?title=8-Aminoadenine&action=edit&redlink=1" class="new" title="8-Aminoadenine (page does not exist)">8-Aminoadenine</a></li> <li><a href="/wiki/Adenine" title="Adenine">Adenine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;"><a href="/wiki/Adenosine_receptor" title="Adenosine receptor">P1</a><br />(<a href="/wiki/Adenosine" title="Adenosine">adenosine</a>)</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/w/index.php?title=2-(1-Hexynyl)-N-methyladenosine&action=edit&redlink=1" class="new" title="2-(1-Hexynyl)-N-methyladenosine (page does not exist)">2-(1-Hexynyl)-<i>N</i>-methyladenosine</a></li> <li><a href="/w/index.php?title=2-Cl-IB-MECA&action=edit&redlink=1" class="new" title="2-Cl-IB-MECA (page does not exist)">2-Cl-IB-MECA</a></li> <li><a href="/w/index.php?title=2-Chloroadenosine&action=edit&redlink=1" class="new" title="2-Chloroadenosine (page does not exist)">2-Chloroadenosine</a></li> <li><a href="/w/index.php?title=2%27-MeCCPA&action=edit&redlink=1" class="new" title="2'-MeCCPA (page does not exist)">2'-MeCCPA</a></li> <li><a href="/w/index.php?title=4%27-O-%CE%B2-D-Glucosyl-9-O-(6%27-deoxysaccharosyl)olivil&action=edit&redlink=1" class="new" title="4'-O-β-D-Glucosyl-9-O-(6'-deoxysaccharosyl)olivil (page does not exist)">4'-O-β-D-Glucosyl-9-O-(6''-deoxysaccharosyl)olivil</a></li> <li><a href="/w/index.php?title=5%27-N-ethylcarboxamidoadenosine&action=edit&redlink=1" class="new" title="5'-N-ethylcarboxamidoadenosine (page does not exist)">5'-<i>N</i>-ethylcarboxamidoadenosine</a></li> <li><a href="/wiki/Adenosine" title="Adenosine">Adenosine</a></li> <li><a href="/wiki/Adenosine_diphosphate" title="Adenosine diphosphate">ADP</a></li> <li><a href="/wiki/Adenosine_monophosphate" title="Adenosine monophosphate">AMP</a></li> <li><a href="/w/index.php?title=Apadenoson&action=edit&redlink=1" class="new" title="Apadenoson (page does not exist)">Apadenoson</a></li> <li><a href="/wiki/ATL-146e" class="mw-redirect" title="ATL-146e">ATL-146e</a></li> <li><a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a></li> <li><a href="/wiki/BAY_60%E2%80%936583" title="BAY 60–6583">BAY 60–6583</a></li> <li><a href="/w/index.php?title=Binodenoson&action=edit&redlink=1" class="new" title="Binodenoson (page does not exist)">Binodenoson</a></li> <li><a href="/w/index.php?title=Capadenoson&action=edit&redlink=1" class="new" title="Capadenoson (page does not exist)">Capadenoson</a></li> <li><a href="/wiki/CCPA_(biochemistry)" title="CCPA (biochemistry)">CCPA</a></li> <li><a href="/wiki/CGS-21680" title="CGS-21680">CGS-21680</a></li> <li><a href="/wiki/CP-532,903" title="CP-532,903">CP-532,903</a></li> <li><a href="/w/index.php?title=CV-1808&action=edit&redlink=1" class="new" title="CV-1808 (page does not exist)">CV-1808</a></li> <li><a href="/w/index.php?title=Evodenoson&action=edit&redlink=1" class="new" title="Evodenoson (page does not exist)">Evodenoson</a></li> <li><a href="/w/index.php?title=GR_79236&action=edit&redlink=1" class="new" title="GR 79236 (page does not exist)">GR 79236</a></li> <li><a href="/w/index.php?title=HENECA&action=edit&redlink=1" class="new" title="HENECA (page does not exist)">HENECA</a></li> <li><a href="/w/index.php?title=LUF-5835&action=edit&redlink=1" class="new" title="LUF-5835 (page does not exist)">LUF-5835</a></li> <li><a href="/w/index.php?title=LUF-5845&action=edit&redlink=1" class="new" title="LUF-5845 (page does not exist)">LUF-5845</a></li> <li><a href="/wiki/N6-Cyclopentyladenosine" title="N6-Cyclopentyladenosine"><i>N</i><sup>6</sup>-Cyclopentyladenosine</a></li> <li><a href="/wiki/Namodenoson" title="Namodenoson">Namodenoson</a></li> <li><a href="/w/index.php?title=NECA_(drug)&action=edit&redlink=1" class="new" title="NECA (drug) (page does not exist)">NECA</a></li> <li><a href="/w/index.php?title=Neladenoson_dalanate&action=edit&redlink=1" class="new" title="Neladenoson dalanate (page does not exist)">Neladenoson dalanate</a></li> <li><a href="/w/index.php?title=Piclidenoson&action=edit&redlink=1" class="new" title="Piclidenoson (page does not exist)">Piclidenoson</a></li> <li><a href="/wiki/Regadenoson" title="Regadenoson">Regadenoson</a></li> <li><a href="/w/index.php?title=SDZ_WAG_994&action=edit&redlink=1" class="new" title="SDZ WAG 994 (page does not exist)">SDZ WAG 994</a></li> <li><a href="/w/index.php?title=Selodenoson&action=edit&redlink=1" class="new" title="Selodenoson (page does not exist)">Selodenoson</a></li> <li><a href="/w/index.php?title=Sonedenoson&action=edit&redlink=1" class="new" title="Sonedenoson (page does not exist)">Sonedenoson</a></li> <li><a href="/w/index.php?title=Tecadenoson&action=edit&redlink=1" class="new" title="Tecadenoson (page does not exist)">Tecadenoson</a></li> <li><a href="/w/index.php?title=Trabodenoson&action=edit&redlink=1" class="new" title="Trabodenoson (page does not exist)">Trabodenoson</a></li> <li><a href="/wiki/UK-432,097" title="UK-432,097">UK-432,097</a></li></ul> <ul><li><b>Antagonists:</b> <a href="/wiki/3-Chlorostyrylcaffeine" title="3-Chlorostyrylcaffeine">3-Chlorostyrylcaffeine (CSC)</a></li> <li><a href="/wiki/7-Methylxanthine" title="7-Methylxanthine">7-Methylxanthine</a></li> <li><a href="/wiki/8-Chlorotheophylline" title="8-Chlorotheophylline">8-Chlorotheophylline</a></li> <li><a href="/w/index.php?title=8-Phenyl-1,3-dipropylxanthine&action=edit&redlink=1" class="new" title="8-Phenyl-1,3-dipropylxanthine (page does not exist)">8-Phenyl-1,3-dipropylxanthine</a></li> <li><a href="/wiki/8-Phenyltheophylline" title="8-Phenyltheophylline">8-Phenyltheophylline</a></li> <li><a href="/wiki/Acefylline" title="Acefylline">Acefylline</a></li> <li><a href="/wiki/Aminophylline" title="Aminophylline">Aminophylline</a></li> <li><a href="/wiki/ATL-444" title="ATL-444">ATL-444</a></li> <li><a href="/w/index.php?title=AZD-4635&action=edit&redlink=1" class="new" title="AZD-4635 (page does not exist)">AZD-4635</a></li> <li><a href="/wiki/Bamifylline" title="Bamifylline">Bamifylline</a></li> <li><a href="/wiki/Cafedrine" title="Cafedrine">Cafedrine</a></li> <li><a href="/wiki/Caffeine" title="Caffeine">Caffeine</a></li> <li><a href="/wiki/Caffeine_citrate" title="Caffeine citrate">Caffeine citrate</a></li> <li><a href="/wiki/Cartazolate" title="Cartazolate">Cartazolate</a></li> <li><a href="/w/index.php?title=CGH-2466&action=edit&redlink=1" class="new" title="CGH-2466 (page does not exist)">CGH-2466</a></li> <li><a href="/wiki/CGS-15943" title="CGS-15943">CGS-15943</a></li> <li><a href="/wiki/Choline_theophyllinate" title="Choline theophyllinate">Choline theophyllinate</a></li> <li><a href="/w/index.php?title=Ciforadenant&action=edit&redlink=1" class="new" title="Ciforadenant (page does not exist)">Ciforadenant</a></li> <li><a href="/wiki/8-Cyclopentyl-1,3-dimethylxanthine" title="8-Cyclopentyl-1,3-dimethylxanthine">CPX</a></li> <li><a href="/w/index.php?title=CVT-6883&action=edit&redlink=1" class="new" title="CVT-6883 (page does not exist)">CVT-6883</a></li> <li><a href="/wiki/Dimethazan" title="Dimethazan">Dimethazan</a></li> <li><a href="/wiki/DMPX" title="DMPX">DMPX</a></li> <li><a href="/wiki/8-Cyclopentyl-1,3-dipropylxanthine" class="mw-redirect" title="8-Cyclopentyl-1,3-dipropylxanthine">DPCPX</a></li> <li><a href="/wiki/Dyphylline" class="mw-redirect" title="Dyphylline">Dyphylline</a></li> <li><a href="/wiki/Enprofylline" title="Enprofylline">Enprofylline</a></li> <li><a href="/wiki/Etazolate" title="Etazolate">Etazolate</a></li> <li><a href="/w/index.php?title=Etrumadenant&action=edit&redlink=1" class="new" title="Etrumadenant (page does not exist)">Etrumadenant</a></li> <li><a href="/wiki/Fenethylline" title="Fenethylline">Fenethylline</a></li> <li><a href="/wiki/IBMX" title="IBMX">IBMX</a></li> <li><a href="/w/index.php?title=Imaradenant&action=edit&redlink=1" class="new" title="Imaradenant (page does not exist)">Imaradenant</a></li> <li><a href="/w/index.php?title=Inupadenant&action=edit&redlink=1" class="new" title="Inupadenant (page does not exist)">Inupadenant</a></li> <li><a href="/wiki/ISAM-140" title="ISAM-140">ISAM-140</a></li> <li><a href="/w/index.php?title=ISAM-R316&action=edit&redlink=1" class="new" title="ISAM-R316 (page does not exist)">ISAM-R316</a></li> <li><a href="/wiki/Isovaleric_acid" title="Isovaleric acid">Isovaleric acid</a></li> <li><a href="/wiki/Istradefylline" title="Istradefylline">Istradefylline</a></li> <li><a href="/wiki/KF-26777" title="KF-26777">KF-26777</a></li> <li><a href="/wiki/Lu_AA41063" title="Lu AA41063">Lu AA41063</a></li> <li><a href="/wiki/Lu_AA47070" title="Lu AA47070">Lu AA47070</a></li> <li><a href="/wiki/MRE3008F20" class="mw-redirect" title="MRE3008F20">MRE3008F20</a></li> <li><a href="/wiki/MRS-1191" class="mw-redirect" title="MRS-1191">MRS-1191</a></li> <li><a href="/w/index.php?title=MRS-1220&action=edit&redlink=1" class="new" title="MRS-1220 (page does not exist)">MRS-1220</a></li> <li><a href="/w/index.php?title=MRS-1334&action=edit&redlink=1" class="new" title="MRS-1334 (page does not exist)">MRS-1334</a></li> <li><a href="/wiki/MRS-1523" class="mw-redirect" title="MRS-1523">MRS-1523</a></li> <li><a href="/wiki/MRS-1706" title="MRS-1706">MRS-1706</a></li> <li><a href="/w/index.php?title=MRS-1754&action=edit&redlink=1" class="new" title="MRS-1754 (page does not exist)">MRS-1754</a></li> <li><a href="/w/index.php?title=MRS-3777&action=edit&redlink=1" class="new" title="MRS-3777 (page does not exist)">MRS-3777</a></li> <li><a href="/wiki/MSX-2" title="MSX-2">MSX-2</a></li> <li><a href="/wiki/MSX-3" title="MSX-3">MSX-3</a></li> <li><a href="/wiki/MSX-4" title="MSX-4">MSX-4</a></li> <li><a href="/w/index.php?title=Muvadenant&action=edit&redlink=1" class="new" title="Muvadenant (page does not exist)">Muvadenant</a></li> <li><a href="/wiki/Paraxanthine" title="Paraxanthine">Paraxanthine</a></li> <li><a href="/wiki/Pentoxifylline" title="Pentoxifylline">Pentoxifylline</a></li> <li><a href="/wiki/Preladenant" title="Preladenant">Preladenant</a></li> <li><a href="/wiki/Propentofylline" title="Propentofylline">Propentofylline</a></li> <li><a href="/wiki/Proxyphylline" title="Proxyphylline">Proxyphylline</a></li> <li><a href="/wiki/PSB-10" title="PSB-10">PSB-10</a></li> <li><a href="/w/index.php?title=PSB-11&action=edit&redlink=1" class="new" title="PSB-11 (page does not exist)">PSB-11</a></li> <li><a href="/w/index.php?title=PSB-36&action=edit&redlink=1" class="new" title="PSB-36 (page does not exist)">PSB-36</a></li> <li><a href="/w/index.php?title=PSB-603&action=edit&redlink=1" class="new" title="PSB-603 (page does not exist)">PSB-603</a></li> <li><a href="/w/index.php?title=PSB-788&action=edit&redlink=1" class="new" title="PSB-788 (page does not exist)">PSB-788</a></li> <li><a href="/w/index.php?title=PSB-1115&action=edit&redlink=1" class="new" title="PSB-1115 (page does not exist)">PSB-1115</a></li> <li><a href="/w/index.php?title=PSB-1901&action=edit&redlink=1" class="new" title="PSB-1901 (page does not exist)">PSB-1901</a></li> <li><a href="/wiki/Reversine" title="Reversine">Reversine</a></li> <li><a href="/wiki/Rolofylline" title="Rolofylline">Rolofylline</a></li> <li><a href="/wiki/SCH-442,416" title="SCH-442,416">SCH-442,416</a></li> <li><a href="/wiki/SCH-58261" title="SCH-58261">SCH-58261</a></li> <li><a href="/w/index.php?title=Sipagladenant&action=edit&redlink=1" class="new" title="Sipagladenant (page does not exist)">Sipagladenant</a></li> <li><a href="/w/index.php?title=Taminadenant&action=edit&redlink=1" class="new" title="Taminadenant (page does not exist)">Taminadenant</a></li> <li><a href="/wiki/Theacrine" title="Theacrine">Theacrine</a></li> <li><a href="/wiki/Theobromine" title="Theobromine">Theobromine</a></li> <li><a href="/wiki/Theodrenaline" title="Theodrenaline">Theodrenaline</a></li> <li><a href="/wiki/Theophylline" title="Theophylline">Theophylline</a></li> <li><a href="/w/index.php?title=Tozadenant&action=edit&redlink=1" class="new" title="Tozadenant (page does not exist)">Tozadenant</a></li> <li><a href="/wiki/Tracazolate" title="Tracazolate">Tracazolate</a></li> <li><a href="/w/index.php?title=Vipadenant&action=edit&redlink=1" class="new" title="Vipadenant (page does not exist)">Vipadenant</a></li> <li><a href="/w/index.php?title=VUF-5574&action=edit&redlink=1" class="new" title="VUF-5574 (page does not exist)">VUF-5574</a></li> <li><a href="/wiki/ZM-241,385" title="ZM-241,385">ZM-241,385</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;"><a href="/wiki/P2_receptor" title="P2 receptor">P2</a><br />(<a href="/wiki/Nucleotide" title="Nucleotide">nucleotide</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="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:3em;;text-align:center;"><a href="/wiki/P2X_purinoreceptor" title="P2X purinoreceptor">P2X</a><br />(<a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate"><abbr title="Adenosine triphosphate">ATP</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Adenosine triphosphate</span>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/w/index.php?title=2-Methylthio-ATP&action=edit&redlink=1" class="new" title="2-Methylthio-ATP (page does not exist)">2-Me-SATP</a></li> <li><a href="/w/index.php?title=%CE%91,%CE%B2-Methylene-ATP&action=edit&redlink=1" class="new" title="Α,β-Methylene-ATP (page does not exist)">α,β-Me-ATP</a></li> <li><a href="/wiki/Adenosine" title="Adenosine">Adenosine</a></li> <li><a href="/wiki/Adenosine_diphosphate" title="Adenosine diphosphate">ADP</a></li> <li><a href="/wiki/Adenosine_monophosphate" title="Adenosine monophosphate">AMP</a></li> <li><a href="/wiki/Diadenosine_tetraphosphate" class="mw-redirect" title="Diadenosine tetraphosphate">Ap4A</a></li> <li><a href="/w/index.php?title=Diadenosine_pentaphosphate&action=edit&redlink=1" class="new" title="Diadenosine pentaphosphate (page does not exist)">Ap5A</a></li> <li><a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a></li> <li><a href="/w/index.php?title=Adenosine-5%27-(%CE%B3-thio)-triphosphate&action=edit&redlink=1" class="new" title="Adenosine-5'-(γ-thio)-triphosphate (page does not exist)">ATPγS</a></li> <li><a href="/w/index.php?title=BzATP&action=edit&redlink=1" class="new" title="BzATP (page does not exist)">BzATP</a></li> <li><a href="/w/index.php?title=Cibacron_blue&action=edit&redlink=1" class="new" title="Cibacron blue (page does not exist)">Cibacron blue</a></li> <li><a href="/wiki/Cytidine_triphosphate" title="Cytidine triphosphate">CTP</a></li> <li><a href="/w/index.php?title=D-%CE%B2,%CE%B3-Me-ATP&action=edit&redlink=1" class="new" title="D-β,γ-Me-ATP (page does not exist)">D-β,γ-Me-ATP</a></li> <li><a href="/wiki/Guanosine_triphosphate" title="Guanosine triphosphate">GTP</a></li> <li><a href="/w/index.php?title=HT-AMP&action=edit&redlink=1" class="new" title="HT-AMP (page does not exist)">HT-AMP</a></li> <li><a href="/wiki/Ivermectin" title="Ivermectin">Ivermectin</a></li> <li><a href="/w/index.php?title=L-%CE%B2,%CE%B3-Me-ATP&action=edit&redlink=1" class="new" title="L-β,γ-Me-ATP (page does not exist)">L-β,γ-Me-ATP</a></li> <li><a href="/w/index.php?title=MRS-2219&action=edit&redlink=1" class="new" title="MRS-2219 (page does not exist)">MRS-2219</a></li> <li><a href="/w/index.php?title=PAPET-ATP&action=edit&redlink=1" class="new" title="PAPET-ATP (page does not exist)">PAPET-ATP</a></li> <li><a href="/wiki/Uridine_triphosphate" title="Uridine triphosphate">UTP</a></li> <li><a href="/wiki/Zinc" title="Zinc">Zinc</a></li></ul> <ul><li><b>Antagonists:</b> <a href="/w/index.php?title=5-BDBD&action=edit&redlink=1" class="new" title="5-BDBD (page does not exist)">5-BDBD</a></li> <li><a href="/w/index.php?title=A-317491&action=edit&redlink=1" class="new" title="A-317491 (page does not exist)">A-317491</a></li> <li><a href="/w/index.php?title=A-438079&action=edit&redlink=1" class="new" title="A-438079 (page does not exist)">A-438079</a></li> <li><a href="/w/index.php?title=A-740003&action=edit&redlink=1" class="new" title="A-740003 (page does not exist)">A-740003</a></li> <li><a href="/w/index.php?title=A-804598&action=edit&redlink=1" class="new" title="A-804598 (page does not exist)">A-804598</a></li> <li><a href="/w/index.php?title=A-839977&action=edit&redlink=1" class="new" title="A-839977 (page does not exist)">A-839977</a></li> <li><a href="/wiki/AF-353" title="AF-353">AF-353</a></li> <li><a href="/w/index.php?title=AZ-10606120&action=edit&redlink=1" class="new" title="AZ-10606120 (page does not exist)">AZ-10606120</a></li> <li><a href="/w/index.php?title=AZ-11645373&action=edit&redlink=1" class="new" title="AZ-11645373 (page does not exist)">AZ-11645373</a></li> <li><a href="/wiki/Brilliant_Blue_G" class="mw-redirect" title="Brilliant Blue G">BBG</a></li> <li><a href="/wiki/Calcium" title="Calcium">Calcium</a></li> <li><a href="/w/index.php?title=Calmidazolium&action=edit&redlink=1" class="new" title="Calmidazolium (page does not exist)">Calmidazolium</a></li> <li><a href="/wiki/Chelerythrine" title="Chelerythrine">Chelerythrine</a></li> <li><a href="/wiki/Copper" title="Copper">Copper</a></li> <li><a href="/wiki/Emodin" title="Emodin">Emodin</a> (<i><a href="/wiki/Rheum_officinale" title="Rheum officinale">Rheum officinale</a></i>)</li> <li><a href="/wiki/Evans_blue_(dye)" title="Evans blue (dye)">Evans blue</a></li> <li><a href="/wiki/Gefapixant" title="Gefapixant">Gefapixant</a></li> <li><a href="/w/index.php?title=GW-791343&action=edit&redlink=1" class="new" title="GW-791343 (page does not exist)">GW-791343</a></li> <li><a href="/w/index.php?title=5-(N,N-Hexamethylene)amiloride&action=edit&redlink=1" class="new" title="5-(N,N-Hexamethylene)amiloride (page does not exist)">HMA</a></li> <li><a href="/w/index.php?title=Diinosine_pentaphosphate&action=edit&redlink=1" class="new" title="Diinosine pentaphosphate (page does not exist)">Ip5I</a></li> <li><a href="/w/index.php?title=IsoPPADS&action=edit&redlink=1" class="new" title="IsoPPADS (page does not exist)">isoPPADS</a></li> <li><a href="/w/index.php?title=JNJ-47965567&action=edit&redlink=1" class="new" title="JNJ-47965567 (page does not exist)">JNJ-47965567</a></li> <li><a href="/w/index.php?title=KN-04&action=edit&redlink=1" class="new" title="KN-04 (page does not exist)">KN-04</a></li> <li><a href="/wiki/KN-62" title="KN-62">KN-62</a></li> <li><a href="/wiki/Magnesium" title="Magnesium">Magnesium</a></li> <li><a href="/w/index.php?title=MRS-2159&action=edit&redlink=1" class="new" title="MRS-2159 (page does not exist)">MRS-2159</a></li> <li><a href="/w/index.php?title=NF-023&action=edit&redlink=1" class="new" title="NF-023 (page does not exist)">NF-023</a></li> <li><a href="/w/index.php?title=NF-110&action=edit&redlink=1" class="new" title="NF-110 (page does not exist)">NF-110</a></li> <li><a href="/w/index.php?title=NF-157&action=edit&redlink=1" class="new" title="NF-157 (page does not exist)">NF-157</a></li> <li><a href="/w/index.php?title=NF-279&action=edit&redlink=1" class="new" title="NF-279 (page does not exist)">NF-279</a></li> <li><a href="/w/index.php?title=NF-449&action=edit&redlink=1" class="new" title="NF-449 (page does not exist)">NF-449</a></li> <li><a href="/wiki/Opiranserin" title="Opiranserin">Opiranserin (VVZ-149)</a></li> <li><a href="/w/index.php?title=Oxidized-ATP&action=edit&redlink=1" class="new" title="Oxidized-ATP (page does not exist)">Oxidized-ATP</a></li> <li><a href="/wiki/Phenol_Red" class="mw-redirect" title="Phenol Red">Phenol Red</a></li> <li><a href="/wiki/Phenolphthalein" title="Phenolphthalein">Phenolphthalein</a></li> <li><a href="/wiki/PPADS" title="PPADS">PPADS</a></li> <li><a href="/w/index.php?title=PPNDS&action=edit&redlink=1" class="new" title="PPNDS (page does not exist)">PPNDS</a></li> <li><a href="/w/index.php?title=PSB-12062&action=edit&redlink=1" class="new" title="PSB-12062 (page does not exist)">PSB-12062</a></li> <li><a href="/wiki/Puerarin" title="Puerarin">Puerarin</a> (<i><a href="/wiki/Radix_puerariae" class="mw-redirect" title="Radix puerariae">Radix puerariae</a></i>)</li> <li><a href="/w/index.php?title=Purotoxin_1&action=edit&redlink=1" class="new" title="Purotoxin 1 (page does not exist)">Purotoxin 1</a></li> <li><a href="/w/index.php?title=Reactive_Blue_2&action=edit&redlink=1" class="new" title="Reactive Blue 2 (page does not exist)">RB-2</a></li> <li><a href="/w/index.php?title=Ro_0437626&action=edit&redlink=1" class="new" title="Ro 0437626 (page does not exist)">Ro 0437626</a></li> <li><a href="/w/index.php?title=Ro_51&action=edit&redlink=1" class="new" title="Ro 51 (page does not exist)">Ro 51</a></li> <li><a href="/w/index.php?title=RO-3&action=edit&redlink=1" class="new" title="RO-3 (page does not exist)">RO-3</a></li> <li><a href="/wiki/Sodium_ferulate" title="Sodium ferulate">Sodium ferulate</a> (<i><a href="/wiki/Angelica_sinensis" title="Angelica sinensis">Angelica sinensis</a></i>, <i><a href="/wiki/Ligusticum_wallichii" class="mw-redirect" title="Ligusticum wallichii">Ligusticum wallichii</a></i>)</li> <li><a href="/wiki/Suramin" title="Suramin">Suramin</a></li> <li><a href="/w/index.php?title=TC-P_262&action=edit&redlink=1" class="new" title="TC-P 262 (page does not exist)">TC-P 262</a></li> <li><a href="/wiki/Tetramethylpyrazine" title="Tetramethylpyrazine">Tetramethylpyrazine (ligustrazine)</a> (<i><a href="/wiki/Ligusticum_wallichii" class="mw-redirect" title="Ligusticum wallichii">Ligusticum wallichii</a></i>)</li> <li><a href="/wiki/TNP-ATP" title="TNP-ATP">TNP-ATP</a></li> <li><a href="/wiki/Zinc" title="Zinc">Zinc</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:3em;;text-align:center;"><a href="/wiki/P2Y_receptor" title="P2Y receptor">P2Y</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/w/index.php?title=2-Methylthioladenosine_diphosphate&action=edit&redlink=1" class="new" title="2-Methylthioladenosine diphosphate (page does not exist)">2-Me-SADP</a></li> <li><a href="/w/index.php?title=2-Methylthioadenosine_triphosphate&action=edit&redlink=1" class="new" title="2-Methylthioadenosine triphosphate (page does not exist)">2-Me-SATP</a></li> <li><a href="/w/index.php?title=2-Thio-UTP&action=edit&redlink=1" class="new" title="2-Thio-UTP (page does not exist)">2-Thio-UTP</a></li> <li><a href="/w/index.php?title=5-Bromouridine_5%E2%80%B2-diphosphate&action=edit&redlink=1" class="new" title="5-Bromouridine 5′-diphosphate (page does not exist)">5-Br-UDP</a></li> <li><a href="/w/index.php?title=5-OMe-UDP&action=edit&redlink=1" class="new" title="5-OMe-UDP (page does not exist)">5-OMe-UDP</a></li> <li><a href="/w/index.php?title=%CE%91,%CE%B2-Methylene-ATP&action=edit&redlink=1" class="new" title="Α,β-Methylene-ATP (page does not exist)">α,β-Me-ATP</a></li> <li><a href="/wiki/Adenosine" title="Adenosine">Adenosine</a></li> <li><a href="/wiki/Adenosine_diphosphate" title="Adenosine diphosphate">ADP</a></li> <li><a href="/w/index.php?title=Adenosine-5%27-(%CE%B2-thio)-diphosphate&action=edit&redlink=1" class="new" title="Adenosine-5'-(β-thio)-diphosphate (page does not exist)">ADPβS</a></li> <li><a href="/w/index.php?title=Diadenosine_triphosphate&action=edit&redlink=1" class="new" title="Diadenosine triphosphate (page does not exist)">Ap3A</a></li> <li><a href="/w/index.php?title=AR-C_67085MX&action=edit&redlink=1" class="new" title="AR-C 67085MX (page does not exist)">AR-C 67085MX</a></li> <li><a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a></li> <li><a href="/w/index.php?title=Adenosine-5%27-(%CE%B3-thio)-triphosphate&action=edit&redlink=1" class="new" title="Adenosine-5'-(γ-thio)-triphosphate (page does not exist)">ATPγS</a></li> <li><a href="/wiki/Cytidine_triphosphate" title="Cytidine triphosphate">CTP</a></li> <li><a href="/wiki/Deoxyadenosine_triphosphate" title="Deoxyadenosine triphosphate">dATP</a></li> <li><a href="/wiki/Denufosol" title="Denufosol">Denufosol</a></li> <li><a href="/wiki/Diquafosol" title="Diquafosol">Diquafosol</a></li> <li><a href="/w/index.php?title=Inosine_diphosphate&action=edit&redlink=1" class="new" title="Inosine diphosphate (page does not exist)">IDP</a></li> <li><a href="/wiki/Inosine_triphosphate" title="Inosine triphosphate">ITP</a></li> <li><a href="/wiki/INS-365" class="mw-redirect" title="INS-365">INS-365</a></li> <li><a href="/w/index.php?title=INS-37217&action=edit&redlink=1" class="new" title="INS-37217 (page does not exist)">INS-37217</a></li> <li><a href="/w/index.php?title=MRS-2365&action=edit&redlink=1" class="new" title="MRS-2365 (page does not exist)">MRS-2365</a></li> <li><a href="/w/index.php?title=MRS-2690&action=edit&redlink=1" class="new" title="MRS-2690 (page does not exist)">MRS-2690</a></li> <li><a href="/w/index.php?title=MRS-2693&action=edit&redlink=1" class="new" title="MRS-2693 (page does not exist)">MRS-2693</a></li> <li><a href="/w/index.php?title=MRS-2768&action=edit&redlink=1" class="new" title="MRS-2768 (page does not exist)">MRS-2768</a></li> <li><a href="/w/index.php?title=MRS-2957&action=edit&redlink=1" class="new" title="MRS-2957 (page does not exist)">MRS-2957</a></li> <li><a href="/w/index.php?title=MRS-4062&action=edit&redlink=1" class="new" title="MRS-4062 (page does not exist)">MRS-4062</a></li> <li><a href="/w/index.php?title=NF-546&action=edit&redlink=1" class="new" title="NF-546 (page does not exist)">NF-546</a></li> <li><a href="/w/index.php?title=PAPET-ATP&action=edit&redlink=1" class="new" title="PAPET-ATP (page does not exist)">PAPET-ATP</a></li> <li><a href="/w/index.php?title=PSB-0474&action=edit&redlink=1" class="new" title="PSB-0474 (page does not exist)">PSB-0474</a></li> <li><a href="/w/index.php?title=PSB-1114&action=edit&redlink=1" class="new" title="PSB-1114 (page does not exist)">PSB-1114</a></li> <li><a href="/wiki/Uridine_diphosphate" title="Uridine diphosphate">UDP</a></li> <li><a href="/w/index.php?title=Uridine_5%C2%B4-(%CE%B2-thio)-diphosphate&action=edit&redlink=1" class="new" title="Uridine 5´-(β-thio)-diphosphate (page does not exist)">UDPβS</a></li> <li><a href="/wiki/Uridine_diphosphate_galactose" title="Uridine diphosphate galactose">UDP-galactose</a></li> <li><a href="/wiki/Uridine_diphosphate_glucose" title="Uridine diphosphate glucose">UDP-glucose</a></li> <li><a href="/wiki/Uridine_diphosphate_N-acetylglucosamine" title="Uridine diphosphate N-acetylglucosamine">UDP-N-acetylglucosamine</a></li> <li><a href="/w/index.php?title=Diuridine_triphosphate&action=edit&redlink=1" class="new" title="Diuridine triphosphate (page does not exist)">Up3U</a></li> <li><a href="/wiki/Uridine_triphosphate" title="Uridine triphosphate">UTP</a></li> <li><a href="/w/index.php?title=Uridine-5%27-(%CE%B3-thio)-triphosphate&action=edit&redlink=1" class="new" title="Uridine-5'-(γ-thio)-triphosphate (page does not exist)">UTPγS</a></li></ul> <ul><li><b>Antagonists:</b> <a href="/w/index.php?title=2-Methylthioladenosine_monophosphate&action=edit&redlink=1" class="new" title="2-Methylthioladenosine monophosphate (page does not exist)">2-Me-SAMP</a></li> <li><a href="/w/index.php?title=A3P5PS&action=edit&redlink=1" class="new" title="A3P5PS (page does not exist)">A3P5PS</a></li> <li><a href="/w/index.php?title=AMP%CE%B1S&action=edit&redlink=1" class="new" title="AMPαS (page does not exist)">AMPαS</a></li> <li><a href="/wiki/Diadenosine_tetraphosphate" class="mw-redirect" title="Diadenosine tetraphosphate">Ap4A</a></li> <li><a href="/w/index.php?title=AR-C_66096&action=edit&redlink=1" class="new" title="AR-C 66096 (page does not exist)">AR-C 66096</a></li> <li><a href="/w/index.php?title=AR-C_67085MX&action=edit&redlink=1" class="new" title="AR-C 67085MX (page does not exist)">AR-C 67085MX</a></li> <li><a href="/w/index.php?title=AR-C_69931MX&action=edit&redlink=1" class="new" title="AR-C 69931MX (page does not exist)">AR-C 69931MX</a></li> <li><a href="/w/index.php?title=AR-C_118925XX&action=edit&redlink=1" class="new" title="AR-C 118925XX (page does not exist)">AR-C 118925XX</a></li> <li><a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a></li> <li><a href="/w/index.php?title=BzATP&action=edit&redlink=1" class="new" title="BzATP (page does not exist)">BzATP</a></li> <li><a href="/w/index.php?title=C1330-7&action=edit&redlink=1" class="new" title="C1330-7 (page does not exist)">C1330-7</a></li> <li><a href="/wiki/Cangrelor" title="Cangrelor">Cangrelor</a></li> <li><a href="/wiki/Clopidogrel" title="Clopidogrel">Clopidogrel</a></li> <li><a href="/wiki/Elinogrel" title="Elinogrel">Elinogrel</a></li> <li><a href="/w/index.php?title=Diinosine_pentaphosphate&action=edit&redlink=1" class="new" title="Diinosine pentaphosphate (page does not exist)">Ip5I</a></li> <li><a href="/w/index.php?title=MRS-2179&action=edit&redlink=1" class="new" title="MRS-2179 (page does not exist)">MRS-2179</a></li> <li><a href="/w/index.php?title=MRS-2211&action=edit&redlink=1" class="new" title="MRS-2211 (page does not exist)">MRS-2211</a></li> <li><a href="/w/index.php?title=MRS-2279&action=edit&redlink=1" class="new" title="MRS-2279 (page does not exist)">MRS-2279</a></li> <li><a href="/w/index.php?title=MRS-2395&action=edit&redlink=1" class="new" title="MRS-2395 (page does not exist)">MRS-2395</a></li> <li><a href="/w/index.php?title=MRS-2500&action=edit&redlink=1" class="new" title="MRS-2500 (page does not exist)">MRS-2500</a></li> <li><a href="/w/index.php?title=MRS-2578&action=edit&redlink=1" class="new" title="MRS-2578 (page does not exist)">MRS-2578</a></li> <li><a href="/w/index.php?title=NF-157&action=edit&redlink=1" class="new" title="NF-157 (page does not exist)">NF-157</a></li> <li><a href="/w/index.php?title=NF-340&action=edit&redlink=1" class="new" title="NF-340 (page does not exist)">NF-340</a></li> <li><a href="/w/index.php?title=2,2%27-Pyridylisatogen_tosylate&action=edit&redlink=1" class="new" title="2,2'-Pyridylisatogen tosylate (page does not exist)">PIT</a></li> <li><a href="/wiki/PPADS" title="PPADS">PPADS</a></li> <li><a href="/wiki/Prasugrel" title="Prasugrel">Prasugrel</a></li> <li><a href="/w/index.php?title=PSB-0739&action=edit&redlink=1" class="new" title="PSB-0739 (page does not exist)">PSB-0739</a></li> <li><a href="/w/index.php?title=Reactive_Blue_2&action=edit&redlink=1" class="new" title="Reactive Blue 2 (page does not exist)">RB-2</a></li> <li><a href="/wiki/Regrelor" title="Regrelor">Regrelor</a></li> <li><a href="/wiki/Suramin" title="Suramin">Suramin</a></li> <li><a href="/wiki/Ticagrelor" title="Ticagrelor">Ticagrelor</a></li> <li><a href="/wiki/Ticlopidine" title="Ticlopidine">Ticlopidine</a></li> <li><a href="/wiki/Uridine_diphosphate" title="Uridine diphosphate">UDP</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Membrane_transport_protein" title="Membrane transport protein">Transporter</a><br /><small>(<a href="/wiki/Reuptake_inhibitor" title="Reuptake inhibitor">blockers</a>)</small></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:6em;;text-align:center;"><a href="/wiki/Concentrative_nucleoside_transporters" class="mw-redirect" title="Concentrative nucleoside transporters"><abbr title="Concentrative nucleoside transporters">CNTs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Concentrative nucleoside transporters</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=6-Hydroxy-7-methoxyflavone&action=edit&redlink=1" class="new" title="6-Hydroxy-7-methoxyflavone (page does not exist)">6-Hydroxy-7-methoxyflavone</a></li> <li><a href="/wiki/Adenosine" title="Adenosine">Adenosine</a></li> <li><a href="/w/index.php?title=DMeThPmR&action=edit&redlink=1" class="new" title="DMeThPmR (page does not exist)">dMeThPmR</a></li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a></li> <li><a href="/w/index.php?title=KGO-2142&action=edit&redlink=1" class="new" title="KGO-2142 (page does not exist)">KGO-2142</a></li> <li><a href="/w/index.php?title=KGO-2173&action=edit&redlink=1" class="new" title="KGO-2173 (page does not exist)">KGO-2173</a></li> <li><a href="/w/index.php?title=MeThPmR&action=edit&redlink=1" class="new" title="MeThPmR (page does not exist)">MeThPmR</a></li> <li><a href="/wiki/Phloridzin" class="mw-redirect" title="Phloridzin">Phloridzin</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;"><a href="/wiki/Equilibrative_nucleoside_transporters" class="mw-redirect" title="Equilibrative nucleoside transporters"><abbr title="Equilibrative nucleoside transporters">ENTs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Equilibrative nucleoside transporters</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Barbiturate" title="Barbiturate">Barbiturates</a></li> <li><a href="/wiki/Benzodiazepine" title="Benzodiazepine">Benzodiazepines</a></li> <li><a href="/wiki/Cilostazol" title="Cilostazol">Cilostazol</a></li> <li><a href="/wiki/Dilazep" title="Dilazep">Dilazep</a></li> <li><a href="/wiki/Dipyridamole" title="Dipyridamole">Dipyridamole</a></li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a></li> <li><a href="/wiki/Ethanol" title="Ethanol">Ethanol</a></li> <li><a href="/wiki/Hexobendine" title="Hexobendine">Hexobendine</a></li> <li><a href="/w/index.php?title=6-S-((4-Nitrophenyl)methyl)-6-thioinosine&action=edit&redlink=1" class="new" title="6-S-((4-Nitrophenyl)methyl)-6-thioinosine (page does not exist)">NBMPR</a></li> <li><a href="/wiki/Pentoxifylline" title="Pentoxifylline">Pentoxifylline</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li> <li><a href="/wiki/Propentofylline" title="Propentofylline">Propentofylline</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;"><a href="/wiki/Plasma_membrane_monoamine_transporter" title="Plasma membrane monoamine transporter"><abbr title="Plasma membrane monoamine transporter">PMAT</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Plasma membrane monoamine transporter</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Decynium-22" title="Decynium-22">Decynium-22</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Enzyme" title="Enzyme">Enzyme</a><br /><small>(<a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">inhibitors</a>)</small></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:6em;;text-align:center;"><a href="/wiki/Xanthine_oxidase" title="Xanthine oxidase"><abbr title="Xanthine oxidase">XO</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Xanthine oxidase</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Allopurinol" title="Allopurinol">Allopurinol</a></li> <li><a href="/wiki/Amflutizole" title="Amflutizole">Amflutizole</a></li> <li><a href="/wiki/Benzbromarone" title="Benzbromarone">Benzbromarone</a></li> <li><a class="mw-selflink selflink">Caffeic acid</a></li> <li><a href="/wiki/Cinnamaldehyde" title="Cinnamaldehyde">Cinnamaldehyde</a></li> <li><i><a href="/wiki/Cinnamomum_osmophloeum" title="Cinnamomum osmophloeum">Cinnamomum osmophloeum</a></i></li> <li><a href="/wiki/Febuxostat" title="Febuxostat">Febuxostat</a></li> <li><a href="/wiki/Myo-inositol" class="mw-redirect" title="Myo-inositol">Myo-inositol</a></li> <li><a href="/wiki/Kaempferol" title="Kaempferol">Kaempferol</a></li> <li><a href="/wiki/Myricetin" title="Myricetin">Myricetin</a></li> <li><a href="/w/index.php?title=Niraxostat&action=edit&redlink=1" class="new" title="Niraxostat (page does not exist)">Niraxostat</a></li> <li><a href="/wiki/Oxipurinol" title="Oxipurinol">Oxipurinol</a></li> <li><a href="/wiki/Phytic_acid" title="Phytic acid">Phytic acid</a></li> <li><i><a href="/wiki/Pistacia_integerrima" title="Pistacia integerrima">Pistacia integerrima</a></i></li> <li><a href="/wiki/Propolis" title="Propolis">Propolis</a></li> <li><a href="/wiki/Quercetin" title="Quercetin">Quercetin</a></li> <li><a href="/wiki/Tisopurine" title="Tisopurine">Tisopurine</a></li> <li><a href="/wiki/Topiroxostat" title="Topiroxostat">Topiroxostat</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;">Others</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aminopterin" title="Aminopterin">Aminopterin</a></li> <li><a href="/wiki/Azathioprine" title="Azathioprine">Azathioprine</a></li> <li><a href="/wiki/Methotrexate" title="Methotrexate">Methotrexate</a></li> <li><a href="/wiki/Mycophenolic_acid" title="Mycophenolic acid">Mycophenolic acid</a></li> <li><a href="/wiki/Pemetrexed" title="Pemetrexed">Pemetrexed</a></li> <li><a href="/wiki/Pralatrexate" title="Pralatrexate">Pralatrexate</a></li> <li><i>Many others</i></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Others</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><b>Precursors:</b> <a href="/wiki/Adenine" title="Adenine">Adenine</a></li> <li><a href="/wiki/Adenosine" title="Adenosine">Adenosine</a></li> <li><a href="/wiki/Adenosine_monophosphate" title="Adenosine monophosphate">AMP</a></li> <li><a href="/wiki/Adenosine_diphosphate" title="Adenosine diphosphate">ADP</a></li> <li><a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a></li> <li><a href="/wiki/Cytosine" title="Cytosine">Cytosine</a></li> <li><a href="/wiki/Cytidine" title="Cytidine">Cytidine</a></li> <li><a href="/wiki/Cytidine_monophosphate" title="Cytidine monophosphate">CMP</a></li> <li><a href="/wiki/Cytidine_diphosphate" title="Cytidine diphosphate">CDP</a></li> <li><a href="/wiki/Cytidine_triphosphate" title="Cytidine triphosphate">CTP</a></li> <li><a href="/wiki/Guanine" title="Guanine">Guanine</a></li> <li><a href="/wiki/Guanosine" title="Guanosine">Guanosine</a></li> <li><a href="/wiki/Guanosine_monophosphate" title="Guanosine monophosphate">GMP</a></li> <li><a href="/wiki/Guanosine_diphosphate" title="Guanosine diphosphate">GDP</a></li> <li><a href="/wiki/Guanosine_triphosphate" title="Guanosine triphosphate">GTP</a></li> <li><a href="/wiki/Hypoxanthine" title="Hypoxanthine">Hypoxanthine</a></li> <li><a href="/wiki/Inosine" title="Inosine">Inosine</a></li> <li><a href="/wiki/Inosine_monophosphate" class="mw-redirect" title="Inosine monophosphate">IMP</a></li> <li><a href="/w/index.php?title=Inosine_diphosphate&action=edit&redlink=1" class="new" title="Inosine diphosphate (page does not exist)">IDP</a></li> <li><a href="/wiki/Inosine_triphosphate" title="Inosine triphosphate">ITP</a></li> <li><a href="/wiki/Ribose" title="Ribose">Ribose</a></li> <li><a href="/wiki/Uracil" title="Uracil">Uracil</a></li> <li><a href="/wiki/Uridine" title="Uridine">Uridine</a></li> <li><a href="/wiki/Uridine_monophosphate" title="Uridine monophosphate">UMP</a></li> <li><a href="/wiki/Uridine_diphosphate" title="Uridine diphosphate">UDP</a></li> <li><a href="/wiki/Uridine_triphosphate" title="Uridine triphosphate">UTP</a></li></ul> <ul><li><b>Others:</b> <a href="/wiki/Chrysophanol" title="Chrysophanol">Chrysophanol</a> (<a href="/wiki/Rhubarb" title="Rhubarb">rhubarb</a>)</li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div><i><b>See also:</b> <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></i></div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" 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