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href="#Antithrombotic"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.5</span> <span>Antithrombotic</span> </div> </a> <ul id="toc-Antithrombotic-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Antidiabetic" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Antidiabetic"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.6</span> <span>Antidiabetic</span> </div> </a> <ul id="toc-Antidiabetic-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Antiatherosclerotic" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Antiatherosclerotic"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.7</span> <span>Antiatherosclerotic</span> </div> </a> <ul id="toc-Antiatherosclerotic-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Neuroprotectant" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Neuroprotectant"> <div 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class="vector-toc-link" href="#Immunomodulatory_activities"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.11</span> <span>Immunomodulatory activities</span> </div> </a> <ul id="toc-Immunomodulatory_activities-sublist" class="vector-toc-list"> </ul> </li> </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">4</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" title="Table of Contents" > <input type="checkbox" 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mw-list-item"><a href="https://de.wikipedia.org/wiki/Myricetin" title="Myricetin – German" lang="de" hreflang="de" data-title="Myricetin" 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/Miricetina" title="Miricetina – Spanish" lang="es" hreflang="es" data-title="Miricetina" 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/Miriketino" title="Miriketino – Esperanto" lang="eo" hreflang="eo" data-title="Miriketino" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%85%DB%8C%D8%B1%DB%8C%D8%B3%D8%AA%DB%8C%D9%86" title="میریستین – Persian" lang="fa" hreflang="fa" data-title="میریستین" 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/Myric%C3%A9tine" title="Myricétine – French" lang="fr" hreflang="fr" data-title="Myricétine" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%9F%E3%83%AA%E3%82%BB%E3%83%81%E3%83%B3" title="ミリセチン – Japanese" lang="ja" hreflang="ja" data-title="ミリセチン" 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/Mirycetyna" title="Mirycetyna – Polish" lang="pl" hreflang="pl" data-title="Mirycetyna" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Miricetin%C4%83" title="Miricetină – Romanian" lang="ro" hreflang="ro" data-title="Miricetină" 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%9C%D0%B8%D1%80%D0%B8%D1%86%D0%B5%D1%82%D0%B8%D0%BD" title="Мирицетин – Russian" lang="ru" hreflang="ru" data-title="Мирицетин" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Miricetin" title="Miricetin – Serbian" lang="sr" hreflang="sr" data-title="Miricetin" 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/Miricetin" title="Miricetin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Miricetin" 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-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Myricetin" title="Myricetin – Swedish" lang="sv" hreflang="sv" data-title="Myricetin" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E6%9D%A8%E6%A2%85%E9%BB%84%E9%85%AE" title="杨梅黄酮 – Chinese" lang="zh" hreflang="zh" data-title="杨梅黄酮" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q951449#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="Namespaces"> <div id="p-associated-pages" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-associated-pages" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-nstab-main" class="selected vector-tab-noicon mw-list-item"><a href="/wiki/Myricetin" 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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:r1268415487">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}</style> <table class="infobox ib-chembox"> <caption>Myricetin </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Myricetin.png" class="mw-file-description"><img alt="Skeletal formula of myricetin" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/eb/Myricetin.png/200px-Myricetin.png" decoding="async" width="200" height="131" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/eb/Myricetin.png/300px-Myricetin.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/eb/Myricetin.png/400px-Myricetin.png 2x" data-file-width="670" data-file-height="438" /></a><figcaption></figcaption></figure> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Myricetin-3D-balls.png" class="mw-file-description"><img alt="Ball-and-stick model of the myricetin molecule" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2d/Myricetin-3D-balls.png/220px-Myricetin-3D-balls.png" decoding="async" width="220" height="176" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2d/Myricetin-3D-balls.png/330px-Myricetin-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2d/Myricetin-3D-balls.png/440px-Myricetin-3D-balls.png 2x" data-file-width="2000" data-file-height="1600" /></a><figcaption></figcaption></figure> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">3,3′,4′,5,5′,7-Hexahydroxyflavone</div> </td></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature#Systematic_name" title="Chemical nomenclature">Systematic IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">3,5,7-Trihydroxy-2-(3,4,5-trihydroxyphenyl)-4<i>H</i>-1-benzopyran-4-one</div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">Cannabiscetin<br />Myricetol<br />Myricitin</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=529-44-2">529-44-2</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=Oc1cc%28O%29c2c%28%3DO%29c%28O%29c%28oc2c1%29c3cc%28O%29c%28O%29c%28O%29c3">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=18152">CHEBI:18152</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL164">ChEMBL164</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.4444991.html">4444991</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/DB02375">DB02375</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/100.007.695">100.007.695</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q951449#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>208-463-2</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/C10107">C10107</a></span></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/5281672">5281672</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/76XC01FTOJ">76XC01FTOJ</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/DTXSID8022400">DTXSID8022400</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q951449#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C15H10O8/c16-6-3-7(17)11-10(4-6)23-15(14(22)13(11)21)5-1-8(18)12(20)9(19)2-5/h1-4,16-20,22H<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: IKMDFBPHZNJCSN-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">Oc1cc(O)c2c(=O)c(O)c(oc2c1)c3cc(O)c(O)c(O)c3</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>15</sub><span title="Hydrogen">H</span><sub>10</sub><span title="Oxygen">O</span><sub>8</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002318237000000000♠"></span>318.237</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>1.912 g/mL </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><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> </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> </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="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="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="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 colspan="2" style="text-align:left; background:#f8eaba; color:inherit; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/12px-X_mark.svg.png" decoding="async" width="12" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/18px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/24px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=442913173&page2=Myricetin">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>Myricetin</b> is a member of the <a href="/wiki/Flavonoid" title="Flavonoid">flavonoid</a> class of polyphenolic compounds, with antioxidant properties.<sup id="cite_ref-Ong_1-0" class="reference"><a href="#cite_note-Ong-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Common dietary sources<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> include vegetables (including <a href="/wiki/Tomato" title="Tomato">tomatoes</a>), fruits (including <a href="/wiki/Orange_(fruit)" title="Orange (fruit)">oranges</a>), nuts, berries, tea,<sup id="cite_ref-Ross_3-0" class="reference"><a href="#cite_note-Ross-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> and red wine.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><p>Myricetin is structurally similar to <a href="/wiki/Fisetin" title="Fisetin">fisetin</a>, <a href="/wiki/Luteolin" title="Luteolin">luteolin</a>, and <a href="/wiki/Quercetin" title="Quercetin">quercetin</a> and is reported to have many of the same functions as these other members of the <a href="/wiki/Flavonol" class="mw-redirect" title="Flavonol">flavonol</a> class of flavonoids.<sup id="cite_ref-Ross_3-1" class="reference"><a href="#cite_note-Ross-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Reported average intake of myricetin per day varies depending on diet, but has been shown in the Netherlands to average 23 mg/day.<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> </p><p>Myricetin is produced from the parent compound <a href="/wiki/Taxifolin" title="Taxifolin">taxifolin</a> through the <a href="/wiki/Ampelopsin" title="Ampelopsin">(+)-dihydromyricetin</a> intermediate and can be further processed to form <a href="/wiki/Laricitrin" title="Laricitrin">laricitrin</a> and then <a href="/wiki/Syringetin" title="Syringetin">syringetin</a>, both members of the flavonol class of flavonoids.<sup id="cite_ref-Flamini_6-0" class="reference"><a href="#cite_note-Flamini-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Dihydromyricetin is frequently sold as a supplement and has controversial function as a partial <a href="/wiki/GABAA_receptor" title="GABAA receptor">GABA<sub>A</sub> receptor</a> potentiator and treatment in <a href="/wiki/Alcoholism" title="Alcoholism">Alcohol Use Disorder (AUD)</a>. Myricetin can alternatively be produced directly from <a href="/wiki/Kaempferol" title="Kaempferol">kaempferol</a>, which is another flavonol.<sup id="cite_ref-Flamini_6-1" class="reference"><a href="#cite_note-Flamini-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Sources">Sources</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Myricetin&action=edit&section=1" title="Edit section: Sources"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <table class="wikitable sortable"> <tbody><tr> <th>Foods </th> <th data-sort-type="number">Myricetin <p><small>(mg/100g)</small> </p> </th></tr> <tr> <td><a href="/wiki/Carob" title="Carob">carob</a> fiber </td> <td>48<sup id="cite_ref-usda_7-0" class="reference"><a href="#cite_note-usda-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Fennel" title="Fennel">fennel</a> leaves, raw </td> <td>20<sup id="cite_ref-usda_7-1" class="reference"><a href="#cite_note-usda-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Parsley" title="Parsley">parsley</a>, fresh </td> <td>15<sup id="cite_ref-usda_7-2" class="reference"><a href="#cite_note-usda-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Goji" title="Goji">goji berry</a>, dried </td> <td>11<sup id="cite_ref-usda_7-3" class="reference"><a href="#cite_note-usda-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Vaccinium_uliginosum" title="Vaccinium uliginosum">bog blueberry</a>, frozen </td> <td>7<sup id="cite_ref-usda_7-4" class="reference"><a href="#cite_note-usda-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Carob" title="Carob">carob</a> flour </td> <td>7<sup id="cite_ref-usda_7-5" class="reference"><a href="#cite_note-usda-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Cranberry" title="Cranberry">cranberry</a> </td> <td>7<sup id="cite_ref-usda_7-6" class="reference"><a href="#cite_note-usda-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Rumex" title="Rumex">dock</a>, raw </td> <td>6<sup id="cite_ref-usda_7-7" class="reference"><a href="#cite_note-usda-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Blackcurrant" title="Blackcurrant">European black currant</a>, raw </td> <td>6<sup id="cite_ref-usda_7-8" class="reference"><a href="#cite_note-usda-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Empetrum_nigrum" title="Empetrum nigrum">crowberry</a> </td> <td>5<sup id="cite_ref-usda_7-9" class="reference"><a href="#cite_note-usda-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Vaccinium_virgatum" title="Vaccinium virgatum">rabbit-eye blueberry</a>, raw </td> <td>5<sup id="cite_ref-usda_7-10" class="reference"><a href="#cite_note-usda-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Sweet_potato" title="Sweet potato">sweet potato</a> leaves, raw </td> <td>4<sup id="cite_ref-usda_7-11" class="reference"><a href="#cite_note-usda-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Oxidative_Properties">Oxidative Properties</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Myricetin&action=edit&section=2" title="Edit section: Oxidative Properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Antioxidant">Antioxidant</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Myricetin&action=edit&section=3" title="Edit section: Antioxidant"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Antioxidants" class="mw-redirect" title="Antioxidants">Antioxidants</a> are molecules present in fruits and vegetables that have been demonstrated to protect against some forms of cancer and cardiovascular disease. Biomolecules and cell structures can experience oxidative stress due to the presence and activity of <a href="/wiki/Reactive_oxygen_species" title="Reactive oxygen species">reactive oxygen species</a> (ROS). ROS like •OH, •O<sub>2</sub><sup>−</sup>, and H<sub>2</sub>O<sub>2</sub> are produced during cellular metabolism processes (<a href="/wiki/Aerobic_respiration" class="mw-redirect" title="Aerobic respiration">aerobic respiration</a>). ROS can damage lipids, DNA, and proteins. </p><p>Gradual but steady accretion of such damage can lead to the development of many diseases and conditions including thrombosis, diabetes, persistent inflammation, cancer, and atherosclerosis. Flavonoids including myricetin are able to scavenge for ROS and can <a href="/wiki/Chelating_agent" class="mw-redirect" title="Chelating agent">chelate</a> intracellular transition metal ions that ultimately produce ROS.<sup id="cite_ref-Ross_3-2" class="reference"><a href="#cite_note-Ross-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>Myricetin also enhances the effects of other antioxidants. Myricetin can induce the enzyme <a href="/wiki/Glutathione_S-transferase" title="Glutathione S-transferase">glutathione S-transferase</a> (GST). GST has been suggested to protect cells against oxidative stress by protecting cells against free-radicals. <i>In vitro</i> studies have shown that myricetin significantly increased GST activity.<sup id="cite_ref-Ross_3-3" class="reference"><a href="#cite_note-Ross-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Pro-oxidant">Pro-oxidant</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Myricetin&action=edit&section=4" title="Edit section: Pro-oxidant"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Multiple studies have demonstrated that myricetin also has the potential to act as a <a href="/wiki/Pro-oxidant" title="Pro-oxidant">pro-oxidant</a> due to its tendency to undergo <a href="/wiki/Autoxidation" title="Autoxidation">autoxidation</a> depending upon its environment <sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (November 2021)">citation needed</span></a></i>]</sup>. It has been seen that when in the presence of cyanide, autoxidation is favored, resulting in superoxide, a byproduct characteristic of causing cellular damage <sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (November 2021)">citation needed</span></a></i>]</sup>. However, sodium azide, <a href="/wiki/Superoxide_dismutase" title="Superoxide dismutase">superoxide dismutase</a>, and <a href="/wiki/Catalase" title="Catalase">catalase</a> have been seen to inhibit the autoxidation of myricetin.<sup id="cite_ref-Ong_1-1" class="reference"><a href="#cite_note-Ong-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p><p>Myricetin may also act as a pro-oxidant in its ability to increase the production of <a href="/wiki/Hydroxy_radical" class="mw-redirect" title="Hydroxy radical">hydroxy radicals</a> through reactions with Fe<sup>2+</sup> or Fe<sup>3+</sup>−<a href="/wiki/EDTA" class="mw-redirect" title="EDTA">EDTA</a> and <a href="/wiki/Hydrogen_peroxide" title="Hydrogen peroxide">hydrogen peroxide</a><sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (November 2021)">citation needed</span></a></i>]</sup>. The resulting hydroxy radicals are often linked to DNA degradation, however, there are doubts as to whether or not this damage would be significant when analyzed <i>in vivo</i> since <i>in vitro</i> studies with both <a href="/wiki/Bovine" class="mw-redirect" title="Bovine">bovine</a> and human <a href="/wiki/Serum_albumin" title="Serum albumin">serum albumin</a> exhibited extensive protection against it.<sup id="cite_ref-Ong_1-2" class="reference"><a href="#cite_note-Ong-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p><p>Myricetin's pro-oxidative capabilities can also be seen in its ability to act as an inhibitory agent against <a href="/wiki/Glutathione_reductase" title="Glutathione reductase">glutathione reductase</a>, which is responsible for regenerating <a href="/wiki/Glutathione" title="Glutathione">glutathione</a>, a scavenger of <a href="/wiki/Free_radicals" class="mw-redirect" title="Free radicals">free radicals</a> and peroxides.<sup id="cite_ref-Ong_1-3" class="reference"><a href="#cite_note-Ong-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Potential_health_effects">Potential health effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Myricetin&action=edit&section=5" title="Edit section: Potential health effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1251242444">.mw-parser-output .ambox{border:1px solid #a2a9b1;border-left:10px solid #36c;background-color:#fbfbfb;box-sizing:border-box}.mw-parser-output .ambox+link+.ambox,.mw-parser-output .ambox+link+style+.ambox,.mw-parser-output .ambox+link+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+style+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+link+.ambox{margin-top:-1px}html body.mediawiki .mw-parser-output .ambox.mbox-small-left{margin:4px 1em 4px 0;overflow:hidden;width:238px;border-collapse:collapse;font-size:88%;line-height:1.25em}.mw-parser-output .ambox-speedy{border-left:10px solid #b32424;background-color:#fee7e6}.mw-parser-output .ambox-delete{border-left:10px solid #b32424}.mw-parser-output .ambox-content{border-left:10px solid #f28500}.mw-parser-output .ambox-style{border-left:10px solid #fc3}.mw-parser-output .ambox-move{border-left:10px solid #9932cc}.mw-parser-output .ambox-protection{border-left:10px solid #a2a9b1}.mw-parser-output .ambox .mbox-text{border:none;padding:0.25em 0.5em;width:100%}.mw-parser-output .ambox .mbox-image{border:none;padding:2px 0 2px 0.5em;text-align:center}.mw-parser-output .ambox .mbox-imageright{border:none;padding:2px 0.5em 2px 0;text-align:center}.mw-parser-output .ambox .mbox-empty-cell{border:none;padding:0;width:1px}.mw-parser-output .ambox .mbox-image-div{width:52px}@media(min-width:720px){.mw-parser-output .ambox{margin:0 10%}}@media print{body.ns-0 .mw-parser-output .ambox{display:none!important}}</style><table class="box-Medical_citations_needed plainlinks metadata ambox ambox-content" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/b/b4/Ambox_important.svg/40px-Ambox_important.svg.png" decoding="async" width="40" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/b/b4/Ambox_important.svg/60px-Ambox_important.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/b/b4/Ambox_important.svg/80px-Ambox_important.svg.png 2x" data-file-width="40" data-file-height="40" /></span></span></div></td><td class="mbox-text"><div class="mbox-text-span">This section <b>needs more <a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)">reliable medical references</a> for <a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability">verification</a> or relies too heavily on <a href="/wiki/Wikipedia:Primary_sources" class="mw-redirect" title="Wikipedia:Primary sources">primary sources</a></b>.<span class="hide-when-compact"> Please review the contents of the section and <a class="external text" href="https://en.wikipedia.org/w/index.php?title=Myricetin&action=edit">add the appropriate references</a> if you can. Unsourced or poorly sourced material may be challenged and <a href="/wiki/Wikipedia:Verifiability#Burden_of_evidence" title="Wikipedia:Verifiability">removed</a>. <small><span class="plainlinks"><i>Find sources:</i> <a rel="nofollow" class="external text" href="https://www.google.com/search?as_eq=wikipedia&q=%22Myricetin%22">"Myricetin"</a> – <a rel="nofollow" class="external text" href="https://www.google.com/search?tbm=nws&q=%22Myricetin%22+-wikipedia&tbs=ar:1">news</a> <b>·</b> <a rel="nofollow" class="external text" href="https://www.google.com/search?&q=%22Myricetin%22&tbs=bkt:s&tbm=bks">newspapers</a> <b>·</b> <a rel="nofollow" class="external text" href="https://www.google.com/search?tbs=bks:1&q=%22Myricetin%22+-wikipedia">books</a> <b>·</b> <a rel="nofollow" class="external text" href="https://scholar.google.com/scholar?q=%22Myricetin%22">scholar</a> <b>·</b> <a rel="nofollow" class="external text" href="https://www.jstor.org/action/doBasicSearch?Query=%22Myricetin%22&acc=on&wc=on">JSTOR</a></span></small></span> <span class="date-container"><i>(<span class="date">May 2018</span>)</i></span></div></td><td class="mbox-imageright"><div class="mbox-image-div"><span typeof="mw:File"><span><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/ae/Star_of_life.svg/60px-Star_of_life.svg.png" decoding="async" width="52" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/ae/Star_of_life.svg/120px-Star_of_life.svg.png 1.5x" data-file-width="198" data-file-height="192" /></span></span></div></td></tr></tbody></table> <div class="mw-heading mw-heading3"><h3 id="Anticarcinogen">Anticarcinogen</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Myricetin&action=edit&section=6" title="Edit section: Anticarcinogen"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Myricetin is also effective in protecting cells from <a href="/wiki/Carcinogen" title="Carcinogen">carcinogenic</a> mutation. Myricetin reduces the risk of skin tumorigenicity that is caused by <a href="/wiki/Polycyclic_aromatic_hydrocarbons" class="mw-redirect" title="Polycyclic aromatic hydrocarbons">polycyclic aromatic hydrocarbons</a> like <a href="/wiki/Benzo(a)pyrene" title="Benzo(a)pyrene">benzo(a)pyrene</a>, a highly carcinogenic compound. Myricetin provided protection against the formation of skin tumors in mice models after tumor initiating and tumor promoter agents were applied to the skin. On a more biochemical level, it was shown that <a href="/wiki/Topical_medication" title="Topical medication">topical</a> application of myricetin to mice inhibited the binding of benzo(a)pyrenes to DNA and protein native to epidermal skin cells.<sup id="cite_ref-Ong_1-4" class="reference"><a href="#cite_note-Ong-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p><p>Myricetin also has been shown to inhibit the act of genetic mutation as exhibited by the <a href="/wiki/Ames_test" title="Ames test">Ames test</a>. This test showed that myricetin was more effective in preventing mutagenesis initiated by certain carcinogenic polycyclic aromatic hydrocarbons (benzo(a)pyrene, dibenzo(a,h)pyrene, and dibenzo(a,i)pyrene) as compared to others in which it was less effective in preventing against mutagenesis (benzo(a)pyrene 4, 5-oxide and the bay-region diol-epoxides of benzo(a)anthracene, chrysene, and benzo(c)phenathrene).<sup id="cite_ref-Ong_1-5" class="reference"><a href="#cite_note-Ong-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> This data shows that myricetin is not unilaterally able to reduce the carcinogenic activity of all polycyclic aromatic hydrocarbons or even the more specific subclass of benzo(a)pyrenes. Myricetin’s exact biochemical activity is still not fully understood. Clearly there is a multifaceted, complex system involved in the anticarcinogenic activity displayed by myricetin that does not apply equally to all carcinogens of the same subfamily. </p> <div class="mw-heading mw-heading3"><h3 id="Mutagen">Mutagen</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Myricetin&action=edit&section=7" title="Edit section: Mutagen"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>It has also been shown that myricetin can itself act as an agent of mutagenicity. Myricetin can produce <a href="/wiki/Frameshift_mutations" class="mw-redirect" title="Frameshift mutations">frameshift mutations</a> in the genomes of particular strains of <i>Salmonella typhimurium</i>.<sup id="cite_ref-Ong_1-6" class="reference"><a href="#cite_note-Ong-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> In general, biochemical structural studies have shown that flavonoid structures can <a href="/wiki/Tautomer" title="Tautomer">tautomerize</a> in biological systems to become active mutagens.<sup id="cite_ref-Ong_1-7" class="reference"><a href="#cite_note-Ong-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Interactions_with_DNA">Interactions with DNA</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Myricetin&action=edit&section=8" title="Edit section: Interactions with DNA"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Myricetin can act as a <a href="/wiki/Pro-oxidant" title="Pro-oxidant">pro-oxidant</a> compound when it interacts with DNA. Studies involving <i>in vitro</i> models have shown that myricetin causes the degradation of DNA. Additionally, myricetin, in the presence of Fe<sup>3+</sup> and Cu<sup>2+</sup>, intensified this DNA degradation. The antioxidants catalase, superoxide dismutase, mannitol, and sodium azide in combination with Cu<sup>2+</sup> increased the DNA degradation activity of myricetin. Myricetin was shown to create <a href="/wiki/Reactive_oxygen_species" title="Reactive oxygen species">reactive oxygen species</a> that caused the DNA damage.<sup id="cite_ref-Ong_1-8" class="reference"><a href="#cite_note-Ong-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p><p>It has been demonstrated that myricetin, depending on its concentration, displays different oxidizing effects on DNA. Polyphenols like myricetin are able to reduce (donate electrons to) Fe<sup>3+</sup>. Thus, this reaction yields a less oxidized (more reduced) form of the iron cation: Fe<sup>2+</sup> and a less reduced (more oxidized) form of myricetin.<sup id="cite_ref-Ong_1-9" class="reference"><a href="#cite_note-Ong-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> This allows myricetin to form a complex with oxygen and biochemically target the DNA molecule. At higher and higher concentrations of myricetin, the rate of DNA damage has been shown to decrease.<sup id="cite_ref-Ong_1-10" class="reference"><a href="#cite_note-Ong-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> A current hypothesis for why this occurs can be attributed to myricetin’s ability to <a href="/wiki/Chelating_agent" class="mw-redirect" title="Chelating agent">chelate</a> iron (Fe) (myricetin ligand forms two or more coordinate bonds to iron). These <i>in vitro</i> studies cannot be correlated directly to human models and should not be extrapolated. </p><p>Myricetin also impacts the biochemical efficacy and binding ability of large intracellular biomolecules. Myricetin has been shown to inhibit viral <a href="/wiki/Reverse_transcriptase" title="Reverse transcriptase">reverse transcriptase</a>, cellular <a href="/wiki/DNA_polymerase" title="DNA polymerase">DNA polymerase</a>, and cellular <a href="/wiki/RNA_polymerase" title="RNA polymerase">RNA polymerase</a>.<sup id="cite_ref-Ong_1-11" class="reference"><a href="#cite_note-Ong-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Inhibition of cellular DNA polymerases could have dangerous effects on the cell’s ability to replicate its genome and its progression through the <a href="/wiki/Cell_cycle" title="Cell cycle">cell cycle</a>. Inhibition of cellular RNA polymerase could have deleterious effects on the cell’s capacity to transcribe and translate DNA and RNA to produce vital proteins for the cell. Researchers have found that myricetin has the ability to interfere in the RNA polymerase pathway in two different ways. In <a href="/wiki/Escherichia_coli" title="Escherichia coli"><i>E. coli</i></a> myricetin competitively inhibited <a href="/wiki/Guanosine_triphosphate" title="Guanosine triphosphate">GTP</a> substrate binding to RNA polymerase. In T7 <a href="/wiki/Bacteriophages" class="mw-redirect" title="Bacteriophages">bacteriophages</a> myricetin competitively inhibited DNA template binding to RNA polymerase.<sup id="cite_ref-Ong_1-12" class="reference"><a href="#cite_note-Ong-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Antiviral">Antiviral</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Myricetin&action=edit&section=9" title="Edit section: Antiviral"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Myricetin has been seen to demonstrate antiviral activity against a number of viruses including <a href="/wiki/Murine_leukemia_virus" title="Murine leukemia virus">Moloney murine leukemia virus</a>, <a href="/wiki/Murine_leukemia_virus" title="Murine leukemia virus">Rauscher murine leukemia virus</a>, and the <a href="/wiki/Human_immunodeficiency_virus" class="mw-redirect" title="Human immunodeficiency virus">human immunodeficiency virus</a>. Its effects against the proliferation of viruses is thought to be a consequence of myricetin’s ability to inhibit the proper functioning of <a href="/wiki/Reverse_transcriptase" title="Reverse transcriptase">reverse transcriptase</a>. Myricetin was identified as a <a href="/wiki/Competitive_inhibition" title="Competitive inhibition">competitive inhibitor</a> of the reverse transcriptase of Rauscher murine leukemia virus and a partial competitor with respect to the human immunodeficiency virus.<sup id="cite_ref-Ong_1-13" class="reference"><a href="#cite_note-Ong-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Investigations into the activity of the <a href="/wiki/Subtypes_of_HIV" title="Subtypes of HIV">HIV-1 strain</a> when introduced to myricetin suggest the antiviral effects are derived from the inhibition of HIV-1 <a href="/wiki/Integrase" title="Integrase">integrase</a>, however, there are suspicions that the inhibition is non-specific.<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> Structural analysis of myricetin and other flavonoids with observed antiviral effects indicate that the 3,4’ free hydroxyl groups likely are responsible for inhibition.<sup id="cite_ref-Ong_1-14" class="reference"><a href="#cite_note-Ong-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Antithrombotic">Antithrombotic</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Myricetin&action=edit&section=10" title="Edit section: Antithrombotic"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Polyphenol" title="Polyphenol">Polyphenols</a> such as myricetin may prevent oxidative stress-induced <a href="/wiki/Platelet" title="Platelet">platelet</a> activation/aggregation. Thus, consumption of antioxidants may serve an anti-thrombotic function. In addition to offering protection by neutralizing peroxide radicals and effecting <a href="/wiki/Thrombaxane" class="mw-redirect" title="Thrombaxane">thromboxane</a> production via the <a href="/wiki/PTGS1" class="mw-redirect" title="PTGS1">PTGS1</a> pathway, polyphenols such as myricetin may target other platelet activation pathways, limiting fibrinogen’s ability to bind platelet surface receptors.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Antidiabetic">Antidiabetic</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Myricetin&action=edit&section=11" title="Edit section: Antidiabetic"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Several <i>in vitro</i> and animal studies have indicated the antidiabetic capabilities of myricetin; however, the evidence in clinical trials is less convincing. The flavonoid has been demonstrated to have a hypoglycemic effect by increasing the ability of adipocytes, as well as cells of the soleus muscle and liver of rats, to uptake glucose.<sup id="cite_ref-Ong_1-15" class="reference"><a href="#cite_note-Ong-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Minireview_10-0" class="reference"><a href="#cite_note-Minireview-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> This insulinomimetic effect is hypothesized to be a consequence of myricetin's either direct or indirect interaction with <a href="/wiki/GLUT4" title="GLUT4">GLUT4</a>, however, no analysis has produced concrete conclusions detailing exactly from where this effect is derived. In the hepatocytes of rats suffering from diabetes, myricetin has been observed to increase the activity of glycogen synthase 1. In trials done on <i><a href="/wiki/Xenopus_laevis" class="mw-redirect" title="Xenopus laevis">Xenopus laevis</a></i> oocytes, myricetin is thought to regulate the transport of glucose and fructose through the function of glucose transporter 2 (<a href="/wiki/GLUT2" title="GLUT2">GLUT2</a>) in sugar absorption. In addition, daily injections of myricetin into rats has been seen to be correlated with increased sensitivity to insulin, indicating the possibility of using a myricetin as treatment or protection against insulin resistance, a frequent cause of diabetes mellitus. In the mouse myoblast cell line known as <a href="/wiki/C2C12" title="C2C12">C2C12</a>, treatment with myricetin not only increased glucose uptake, but also enhanced <a href="/wiki/Lipogenesis" title="Lipogenesis">lipogenesis</a>, a result not seen from any of the other bioflavonoids tested.<sup id="cite_ref-Minireview_10-1" class="reference"><a href="#cite_note-Minireview-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p><p>Although myricetin has not been concluded to have more than a neutral effect on humans, it has been used as a form of traditional medicine for diabetes in Northern Brazil and is hypothesized by the Finnish Mobile Clinic Health Examination Survey to potentially be correlated to the lower risk of <a href="/wiki/Type_2_diabetes" title="Type 2 diabetes">Type 2 diabetes</a> in individuals whose diets included higher than average amounts of myricetin. However, since studies in the United States, such as the Women's Health Study, do not confirm these results, there is doubt of whether or not the difference is risk can actually be accredited to myricetin and is not the result of the inability to fully control other variables such as racial background or inconsistencies in diet between participants.<sup id="cite_ref-Minireview_10-2" class="reference"><a href="#cite_note-Minireview-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p><p>There is also evidence indicating that other characteristics of myricetin, such as its effect against <a href="/wiki/Inflammation" title="Inflammation">inflammation</a>, <a href="/wiki/Oxidative_stress" title="Oxidative stress">oxidative stress</a>, and <a href="/wiki/Hyperlipidemia" title="Hyperlipidemia">hyperlipidemia</a>, may be helpful to reduce or even prevent other clinical issues which arise from <a href="/wiki/Diabetes_mellitus" class="mw-redirect" title="Diabetes mellitus">diabetes mellitus</a>.<sup id="cite_ref-Minireview_10-3" class="reference"><a href="#cite_note-Minireview-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Antiatherosclerotic">Antiatherosclerotic</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Myricetin&action=edit&section=12" title="Edit section: Antiatherosclerotic"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Antioxidants, including flavonoids such as myricetin, are often touted to reduce the risk of <a href="/wiki/Atherosclerosis" title="Atherosclerosis">atherosclerosis</a>, the hardening of arteries associated with high cholesterol. However, <i>in vivo</i> studies are lacking and <i>in vitro</i> studies are contradictory and do not support this claim. This claim is based on myricetin's proposed ability to increase LDL uptake by macrophages, which in theory would protect against atherosclerosis. This theoretical action of myricetin is not supported by experimental data.<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> It is also proposed that myricetin may have the ability as a potent flavonoid antioxidant to prevent LDL oxidation, thus slowing the body's local inflammatory response and delaying the appearance of the first fatty streak and onset of atherosclerosis.<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> </p><p>Although mechanisms relating to myricetin specifically have not been proven, a diet that is rich in fruits and vegetables, and therefore rich in antioxidants, correlates with a decreased risk of cardiovascular disease, including atherosclerosis.<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><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> </p> <div class="mw-heading mw-heading3"><h3 id="Neuroprotectant">Neuroprotectant</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Myricetin&action=edit&section=13" title="Edit section: Neuroprotectant"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>It has also been shown that myricetin is effective in protecting neurons against oxidative stressors. Researchers have shown that <a href="/wiki/PC12_cells" class="mw-redirect" title="PC12 cells">PC12 cells</a> treated with hydrogen peroxide (H<sub>2</sub>O<sub>2</sub>) as an oxidative stressor experience cell death due to <a href="/wiki/Apoptosis" title="Apoptosis">apoptosis</a>. When treated with myricetin, these oxidatively stressed cells displayed statistically significant increased cell survival.<sup id="cite_ref-Dajas_15-0" class="reference"><a href="#cite_note-Dajas-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> It has been suggested that myricetin not only has oxygen radical scavenging abilities, but also inherent, specific cell-survival capacities. Other molecules known for oxygen radical scavenging (<a href="/wiki/Vitamin_E" title="Vitamin E">vitamin E</a> and <a href="/wiki/Boldine" title="Boldine">boldine</a>) did not successfully protect the cell models from oxidative stress and eventual cell death as effectively as myricetin and other biochemically related molecules.<sup id="cite_ref-Dajas_15-1" class="reference"><a href="#cite_note-Dajas-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Anti-inflammatory">Anti-inflammatory</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Myricetin&action=edit&section=14" title="Edit section: Anti-inflammatory"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Myricetin, along with other lipoxygenase- and cyclooxygenase-blocker flavonoids are seen to have significant anti-inflammatory characteristics, demonstrated by their ability to reduce <a href="/wiki/Edemas" class="mw-redirect" title="Edemas">edemas</a> caused by carrageenan and croton oil.<sup id="cite_ref-Ong_1-16" class="reference"><a href="#cite_note-Ong-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> The anti-inflammatory nature of myricetin lies in its ability to inhibit the amplified production of <a href="/wiki/Cytokines" class="mw-redirect" title="Cytokines">cytokines</a> that occurs during inflammation. Testing on various types of <a href="/wiki/Macrophage" title="Macrophage">macrophage</a> cells, including RAW264.7, as well as on human synovial <a href="/wiki/Sarcoma" title="Sarcoma">sarcoma</a> cells, demonstrated the inhibition of several kinds of cytokines, such as <a href="/wiki/Interleukin-12" class="mw-redirect" title="Interleukin-12">interleukin-12</a> and <a href="/wiki/IL1B" class="mw-redirect" title="IL1B">interleukin-1β</a>, through down-regulation of transcription factors and mediators involved in their production.<sup id="cite_ref-Minireview_10-4" class="reference"><a href="#cite_note-Minireview-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> Other studies suggest that myricetin's anti-inflammatory nature could also potentially be dependent upon interfering in inflammatory signal pathways by inhibiting various kinases and, consequently, the function of <a href="/wiki/Tumor_necrosis_factor_alpha" class="mw-redirect" title="Tumor necrosis factor alpha">tumor necrosis factor alpha</a>.<sup id="cite_ref-Minireview_10-5" class="reference"><a href="#cite_note-Minireview-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Anti-platelet_aggregation_activity">Anti-platelet aggregation activity</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Myricetin&action=edit&section=15" title="Edit section: Anti-platelet aggregation activity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Exposure to myricetin caused inhibition of rabbit <a href="/wiki/Platelet_aggregation" class="mw-redirect" title="Platelet aggregation">platelet aggregation</a>, induced by <a href="/wiki/Adenosine_diphosphate" title="Adenosine diphosphate">adenosine diphosphate</a>, <a href="/wiki/Arachidonic_acid" title="Arachidonic acid">arachidonic acid</a>, <a href="/wiki/Collagen" title="Collagen">collagen</a> and <a href="/wiki/Platelet_activating_factor" class="mw-redirect" title="Platelet activating factor">platelet activating factor</a> (PAF). It inhibited specific receptor binding of PAF in rabbit platelets. The compound was found to be active against <a href="/wiki/Thrombin" title="Thrombin">thrombin</a> and <a href="/wiki/Neutrophil_elastase" title="Neutrophil elastase">neutrophil elastase</a>. In addition, A prostacyclin-stimulated rise in the levels of platelet <a href="/wiki/Adenosine_3%27,5%27-cyclic_monophosphate" class="mw-redirect" title="Adenosine 3',5'-cyclic monophosphate">adenosine 3',5'-cyclic monophosphate</a> (cAMP) was stimulated by myricetin.<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="Immunomodulatory_activities">Immunomodulatory activities</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Myricetin&action=edit&section=16" title="Edit section: Immunomodulatory activities"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Myricetin's preclinical <a href="/wiki/Immunomodulatory" class="mw-redirect" title="Immunomodulatory">immunomodulatory</a> properties are now becoming increasingly widely known.<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> It was discovered that myricetin may prevent <a href="/wiki/T-lymphocyte" class="mw-redirect" title="T-lymphocyte">T-lymphocyte</a> stimulation in a mouse model by binding to anti-CD3 and anti-CD28 <a href="/wiki/Monoclonal_antibody" title="Monoclonal antibody">monoclonal antibodies</a> immobilised on beads. The inhibitory effect of myricetin on T cells, which was described in this study, was explained as being <a href="/wiki/Mediated" title="Mediated">mediated</a> via extracellular <style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>O<sub class="template-chem2-sub">2</sub></span> production. Through the inhibition of NF-B binding activity, these natural compounds were reported to significantly reduce the <a href="/wiki/Lipopolysaccharide" title="Lipopolysaccharide">lipopolysaccharide (LPS)-induced</a> interleukin (IL)-12 production in mouse main <a href="/wiki/Macrophage" title="Macrophage">macrophages</a> as well as the RAW264.7 monocytic cell-line.<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> Myricetin produced <a href="/wiki/Epithelial_layer" class="mw-redirect" title="Epithelial layer">epithelial layer</a> contractile reflexes in separate rat <a href="/wiki/Aortic_ring" class="mw-redirect" title="Aortic ring">aortic rings</a> at a concentration of 50 M.<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> This substance induces the synthesis of <a href="/wiki/Cytosolic_ciliogenesis" title="Cytosolic ciliogenesis">cytosolic</a> unbound calcium in cultured <a href="/wiki/Bovine_somatotropin" title="Bovine somatotropin">bovine</a> endothelial cells. Myricetin suppressed the release of IL-2 protein from mouse EL-4 T cells that had been stimulated with phorbol 12-myristate 13-acetate (PMA) and <a href="/wiki/Ionomycin" title="Ionomycin">ionomycin</a> in a daily dosage approach.<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="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Myricetin&action=edit&section=17" 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 reflist-columns references-column-width reflist-columns-2"> <ol class="references"> <li id="cite_note-Ong-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-Ong_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Ong_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Ong_1-2"><sup><i><b>c</b></i></sup></a> <a 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title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Archives+of+Pharmacal+Research&rft.atitle=Inhibition+of+Interleukin-2+Production+by+Myricetin+in+Mouse+EL-4+T+Cells&rft.volume=30&rft.issue=9&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1075-%3C%2Fspan%3E1079&rft.date=2007-09&rft.issn=0253-6269&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A40028977%23id-name%3DS2CID&rft_id=info%3Apmid%2F17958323&rft_id=info%3Adoi%2F10.1007%2Fbf02980240&rft.aulast=Cho&rft.aufirst=Young-Chang&rft.au=Yoon%2C+Goo&rft.au=Lee%2C+Kwang+Youl&rft.au=Choi%2C+Hyun+Jin&rft.au=Kang%2C+Bok+Yun&rft_id=http%3A%2F%2Fdx.doi.org%2F10.1007%2Fbf02980240&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMyricetin" class="Z3988"></span></span> </li> </ol></div> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist 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ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Flavonols" title="Template:Flavonols"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Flavonols" title="Template talk:Flavonols"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Flavonols" title="Special:EditPage/Template:Flavonols"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Flavonols_and_their_conjugates150" style="font-size:114%;margin:0 4em">Flavonols and their conjugates</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Backbone</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%">Aglycones</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/3-Hydroxyflavone" title="3-Hydroxyflavone">3-Hydroxyflavone</a> (synthetic) and derivatives</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Flavonols" title="Flavonols">Flavonols</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Aglycones</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/Fisetin" title="Fisetin">Fisetin</a></li> <li><a href="/wiki/Galangin" title="Galangin">Galangin</a></li> <li><a href="/wiki/Gossypetin" title="Gossypetin">Gossypetin</a></li> <li><a href="/wiki/Herbacetin" title="Herbacetin">Herbacetin</a></li> <li><a href="/wiki/Kaempferol" title="Kaempferol">Kaempferol</a></li> <li><a href="/wiki/Morin_(flavonol)" title="Morin (flavonol)">Morin</a></li> <li><a class="mw-selflink selflink">Myricetin</a></li> <li><a href="/wiki/Quercetagetin" title="Quercetagetin">Quercetagetin</a></li> <li><a href="/wiki/Quercetin" title="Quercetin">Quercetin</a></li> <li><a href="/wiki/Robinetin" title="Robinetin">Robinetin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Conjugates</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%">Glycosides of <a href="/wiki/Herbacetin" title="Herbacetin">herbacetin</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/Rhodionin" title="Rhodionin">Rhodionin</a></li> <li><a href="/w/index.php?title=Rhodiosin&action=edit&redlink=1" class="new" title="Rhodiosin (page does not exist)">Rhodiosin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Glycosides of <a href="/wiki/Kaempferol" title="Kaempferol">kaempferol</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/Afzelin" title="Afzelin">Afzelin</a> (Kaempferol 3-rhamnoside)</li> <li><a href="/wiki/Astragalin" title="Astragalin">Astragalin</a> (kaempferol 3-O-glucoside)</li> <li><a href="/wiki/Kaempferitrin" title="Kaempferitrin">Kaempferitrin</a> (kaempferol 3,7-dirhamnoside)</li> <li><a href="/wiki/Juglanin" title="Juglanin">Juglanin</a> (Kaempferol 3-O-arabinoside)</li> <li><a href="/w/index.php?title=Kaempferol_3-alpha-L-arabinopyranoside&action=edit&redlink=1" class="new" title="Kaempferol 3-alpha-L-arabinopyranoside (page does not exist)">Kaempferol 3-alpha-L-arabinopyranoside</a></li> <li><a href="/w/index.php?title=Kaempferol_3-alpha-D-arabinopyranoside&action=edit&redlink=1" class="new" title="Kaempferol 3-alpha-D-arabinopyranoside (page does not exist)">Kaempferol 3-alpha-D-arabinopyranoside</a></li> <li><a href="/w/index.php?title=Kaempferol_7-alpha-L-arabinoside&action=edit&redlink=1" class="new" title="Kaempferol 7-alpha-L-arabinoside (page does not exist)">Kaempferol 7-alpha-L-arabinoside</a></li> <li><a href="/wiki/Kaempferol_7-O-glucoside" title="Kaempferol 7-O-glucoside">Kaempferol 7-O-glucoside</a></li> <li><a href="/w/index.php?title=Kaempferol_3-lathyroside&action=edit&redlink=1" class="new" title="Kaempferol 3-lathyroside (page does not exist)">Kaempferol 3-lathyroside</a></li> <li><a href="/w/index.php?title=Kaempferol_4%27-rhamnoside&action=edit&redlink=1" class="new" title="Kaempferol 4'-rhamnoside (page does not exist)">Kaempferol 4'-rhamnoside</a></li> <li><a href="/w/index.php?title=Kaempferol_5-rhamnoside&action=edit&redlink=1" class="new" title="Kaempferol 5-rhamnoside (page does not exist)">Kaempferol 5-rhamnoside</a></li> <li><a href="/w/index.php?title=Kaempferol_7-rhamnoside&action=edit&redlink=1" class="new" title="Kaempferol 7-rhamnoside (page does not exist)">Kaempferol 7-rhamnoside</a></li> <li><a href="/w/index.php?title=Kaempferol_7-O-alpha-L-rhamnofuranoside&action=edit&redlink=1" class="new" title="Kaempferol 7-O-alpha-L-rhamnofuranoside (page does not exist)">Kaempferol 7-O-alpha-L-rhamnofuranoside</a></li> <li><a href="/w/index.php?title=Kaempferol_3-xyloside&action=edit&redlink=1" class="new" title="Kaempferol 3-xyloside (page does not exist)">Kaempferol 3-xyloside</a></li> <li><a href="/w/index.php?title=Kaempferol_7-xyloside&action=edit&redlink=1" class="new" title="Kaempferol 7-xyloside (page does not exist)">Kaempferol 7-xyloside</a></li> <li><a href="/wiki/Robinin" title="Robinin">Robinin</a> (kaempferol-3-O-robinoside-7-O-rhamnoside)</li> <li><a href="/wiki/Kaempferol_3-O-rutinoside" title="Kaempferol 3-O-rutinoside">Kaempferol 3-O-rutinoside</a></li> <li><a href="/w/index.php?title=Sophoraflavonoloside&action=edit&redlink=1" class="new" title="Sophoraflavonoloside (page does not exist)">Sophoraflavonoloside</a> (Kaempferol 3-O-sophoroside)</li> <li><a href="/wiki/Trifolin" title="Trifolin">Trifolin</a> (Kaempferol 3-O-beta-D-galactoside)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Glycosides of <a class="mw-selflink selflink">myricetin</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="/w/index.php?title=Betmidin&action=edit&redlink=1" class="new" title="Betmidin (page does not exist)">Betmidin</a> (<a href="/w/index.php?title=Myricetin_3-O-arabinoside&action=edit&redlink=1" class="new" title="Myricetin 3-O-arabinoside (page does not exist)">Myricetin 3-O-arabinoside</a>)</li> <li><a href="/wiki/Myricetin_3-O-rutinoside" title="Myricetin 3-O-rutinoside">Myricetin 3-O-rutinoside</a></li> <li><a href="/w/index.php?title=Myricetin-3-O-neohesperidoside&action=edit&redlink=1" class="new" title="Myricetin-3-O-neohesperidoside (page does not exist)">Myricetin-3-O-neohesperidoside</a></li> <li><a href="/wiki/Myricitrin" title="Myricitrin">Myricitrin</a> (Myricetin 3-O-rhamnoside)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Conjugates of <a href="/wiki/Quercetin" title="Quercetin">quercetin</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Sulfates</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/Quercetin_3-O-sulfate" title="Quercetin 3-O-sulfate">Quercetin 3-O-sulfate</a></li> <li><a href="/w/index.php?title=Quercetin_3,3%27-bissulfate&action=edit&redlink=1" class="new" title="Quercetin 3,3'-bissulfate (page does not exist)">Quercetin 3,3'-bissulfate</a></li> <li><a href="/w/index.php?title=Quercetin_3,4%27-bissulfate&action=edit&redlink=1" class="new" title="Quercetin 3,4'-bissulfate (page does not exist)">Quercetin 3,4'-bissulfate</a></li></ul> </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="/wiki/Avicularin" title="Avicularin">Avicularin</a> (quercetin-3-O-α-L-arabinofuranoside)</li> <li><a href="/wiki/CTN-986" title="CTN-986">CTN-986</a></li> <li><a href="/wiki/Guaijaverin" title="Guaijaverin">Guaijaverin</a> (quercetin 3-O-<a href="/wiki/Arabinoside" class="mw-redirect" title="Arabinoside">arabinoside</a>)</li> <li><a href="/w/index.php?title=Heliosin&action=edit&redlink=1" class="new" title="Heliosin (page does not exist)">Heliosin</a> (quercetin 3-di<a href="/wiki/Galactoside" title="Galactoside">galactoside</a>)</li> <li><a href="/wiki/Hyperoside" title="Hyperoside">Hyperoside</a> (quercetin 3-O-galactoside)</li> <li><a href="/wiki/Isoquercetin" title="Isoquercetin">Isoquercetin</a> (quercetin 3-O-glucoside)</li> <li><a href="/wiki/Miquelianin" title="Miquelianin">Miquelianin</a> (quercetin 3-O-glucuronide)</li> <li><a href="/wiki/Quercetin_3,4%27-diglucoside" title="Quercetin 3,4'-diglucoside">Quercetin 3,4'-diglucoside</a></li> <li><a href="/w/index.php?title=Quercetin-3-sophorodide&action=edit&redlink=1" class="new" title="Quercetin-3-sophorodide (page does not exist)">Quercetin-3-sophorodide</a></li> <li><a href="/wiki/Quercitrin" title="Quercitrin">Quercitrin</a> (quercetin 3-O-rhamnoside)</li> <li><a href="/wiki/Rutin" title="Rutin">Rutin</a> (quercetin rutinoside)</li> <li><a href="/w/index.php?title=Reinutrin&action=edit&redlink=1" class="new" title="Reinutrin (page does not exist)">Reinutrin</a> (quercetin-3-D-xyloside)</li> <li><a href="/wiki/Spiraeoside" title="Spiraeoside">Spiraeoside</a> (quercetin 4'-O-glucoside)</li> <li><a href="/wiki/Taxillusin" title="Taxillusin">Taxillusin</a> (galloylated 3-O-glucoside of quercetin°</li></ul> </div></td></tr></tbody></table><div></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%"><i>O</i>-Methylated flavonols</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%">Aglycones</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/5-O-Methylmyricetin" title="5-O-Methylmyricetin">5-O-methylmyricetin</a></li> <li><a href="/wiki/Annulatin" title="Annulatin">Annulatin</a></li> <li><a href="/wiki/Ayanin" title="Ayanin">Ayanin</a></li> <li><a href="/wiki/Axillarin" title="Axillarin">Axillarin</a></li> <li><a href="/wiki/Azaleatin" title="Azaleatin">Azaleatin</a></li> <li><a href="/wiki/Brickellin" title="Brickellin">Brickellin</a></li> <li><a href="/wiki/Centaureidin" title="Centaureidin">Centaureidin</a></li> <li><a href="/wiki/Chrysosplenetin" title="Chrysosplenetin">Chrysosplenetin</a></li> <li><a href="/wiki/Combretol" title="Combretol">Combretol</a></li> <li><a href="/wiki/Ermanin" title="Ermanin">Ermanin</a></li> <li><a href="/wiki/Eupatolitin" title="Eupatolitin">Eupatolitin</a></li> <li><a href="/wiki/Eupalitin" title="Eupalitin">Eupalitin</a></li> <li><a href="/wiki/Europetin" title="Europetin">Europetin</a></li> <li><a href="/wiki/Isorhamnetin" title="Isorhamnetin">Isorhamnetin</a></li> <li><a href="/wiki/Jaceidin" title="Jaceidin">Jaceidin</a></li> <li><a href="/wiki/Kaempferide" title="Kaempferide">Kaempferide</a></li> <li><a href="/wiki/Kumatakenin" title="Kumatakenin">Kumatakenin</a></li> <li><a href="/wiki/Laricitrin" title="Laricitrin">Laricitrin</a></li> <li><a href="/wiki/Natsudaidain" title="Natsudaidain">Natsudaidain</a></li> <li><a href="/wiki/Ombuin" title="Ombuin">Ombuin</a></li> <li><a href="/wiki/Pachypodol" title="Pachypodol">Pachypodol</a></li> <li><a href="/wiki/Patuletin" title="Patuletin">Patuletin</a></li> <li><a href="/wiki/Retusin_(flavonol)" title="Retusin (flavonol)">Retusin</a></li> <li><a href="/wiki/Mearnsetin" title="Mearnsetin">Mearnsetin</a></li> <li><a href="/wiki/Rhamnazin" title="Rhamnazin">Rhamnazin</a></li> <li><a href="/wiki/Rhamnetin" title="Rhamnetin">Rhamnetin</a></li> <li><a href="/wiki/Santin_(flavonol)" title="Santin (flavonol)">Santin</a></li> <li><a href="/wiki/Spinacetin" title="Spinacetin">Spinacetin</a></li> <li><a href="/wiki/Syringetin" title="Syringetin">Syringetin</a></li> <li><a href="/wiki/Isorhamnetin" title="Isorhamnetin">Tamarixetin</a></li></ul> </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"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">of isorhamnetin</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=Narcissin&action=edit&redlink=1" class="new" title="Narcissin (page does not exist)">Narcissin</a> (<a href="/w/index.php?title=Isorhamnetin_3-O-rutinoside&action=edit&redlink=1" class="new" title="Isorhamnetin 3-O-rutinoside (page does not exist)">Isorhamnetin 3-O-rutinoside</a>)</li> <li><a href="/w/index.php?title=Isorhamnetin_3-O-glucoside&action=edit&redlink=1" class="new" title="Isorhamnetin 3-O-glucoside (page does not exist)">Isorhamnetin 3-O-glucoside</a></li> <li><a href="/w/index.php?title=Tamarixetin_7-rutinoside&action=edit&redlink=1" class="new" title="Tamarixetin 7-rutinoside (page does not exist)">Tamarixetin 7-rutinoside</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Azalein" title="Azalein">Azalein</a> (Azaleatin 3-O-α-L-rhamnoside)</li> <li><a href="/w/index.php?title=Centaurein&action=edit&redlink=1" class="new" title="Centaurein (page does not exist)">Centaurein</a> (<a href="/w/index.php?title=Centaureidin_7-O-glucoside&action=edit&redlink=1" class="new" title="Centaureidin 7-O-glucoside (page does not exist)">Centaureidin 7-O-glucoside</a>)</li> <li><a href="/wiki/Eupalin" title="Eupalin">Eupalin</a> (Eupalitin 3-0-rhamnoside)</li> <li><a href="/wiki/Eupatolin" title="Eupatolin">Eupatolin</a> (Eupatolitin 3-O-rhamnoside)</li> <li><a href="/w/index.php?title=Jacein&action=edit&redlink=1" class="new" title="Jacein (page does not exist)">Jacein</a> (<a href="/w/index.php?title=Jaceidin_7-O-glucoside&action=edit&redlink=1" class="new" title="Jaceidin 7-O-glucoside (page does not exist)">Jaceidin 7-O-glucoside</a>)</li> <li><a href="/w/index.php?title=Patulitrin&action=edit&redlink=1" class="new" title="Patulitrin (page does not exist)">Patulitrin</a> (<a href="/w/index.php?title=Patuletin_7-O-glucoside&action=edit&redlink=1" class="new" title="Patuletin 7-O-glucoside (page does not exist)">Patuletin 7-O-glucoside</a></li> <li><a href="/wiki/Xanthorhamnin" title="Xanthorhamnin">Xanthorhamnin</a> (Rhamnetin glycoside)</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%">Derivative flavonols</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%">Aglycones</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=Noricaritin&action=edit&redlink=1" class="new" title="Noricaritin (page does not exist)">Noricaritin</a></li> <li><a href="/w/index.php?title=Dihydronoricaritin&action=edit&redlink=1" class="new" title="Dihydronoricaritin (page does not exist)">Dihydronoricaritin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Glycosides</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/Amurensin_(flavonol)" title="Amurensin (flavonol)">Amurensin</a></li> <li><a href="/wiki/Icariin" title="Icariin">Icariin</a></li> <li><a href="/w/index.php?title=Phelloside&action=edit&redlink=1" class="new" title="Phelloside (page does not exist)">Phelloside</a></li> <li><a href="/w/index.php?title=Dihydrophelloside&action=edit&redlink=1" class="new" title="Dihydrophelloside (page does not exist)">Dihydrophelloside</a></li> <li><a href="/w/index.php?title=Rutin_S&action=edit&redlink=1" class="new" title="Rutin S (page does not exist)">Rutin S</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Pyranoflavonols</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%">Aglycones</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/Karanjachromene" title="Karanjachromene">Karanjachromene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Furanoflavonols</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%">Aglycones</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/Karanjin" title="Karanjin">Karanjin</a></li></ul> </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=Pongamoside_A&action=edit&redlink=1" class="new" title="Pongamoside A (page does not exist)">Pongamoside A</a>, <a href="/w/index.php?title=Pongamoside_B&action=edit&redlink=1" class="new" title="Pongamoside B (page does not exist)">B</a> and <a href="/w/index.php?title=Pongamoside_C&action=edit&redlink=1" class="new" title="Pongamoside C (page does not exist)">C</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Semisynthetic</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%">Glycosides</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/Hydroxyethylrutoside" title="Hydroxyethylrutoside">Hydroxyethylrutosides</a> <ul><li><a href="/wiki/Monoxerutin" title="Monoxerutin">Monoxerutin</a></li> <li><a href="/wiki/Troxerutin" title="Troxerutin">Troxerutin</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Purine_receptor_modulators393" 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_modulators393" 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="/wiki/NECA_(drug)" class="mw-redirect" title="NECA (drug)">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="/wiki/Sipagladenant" title="Sipagladenant">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 href="/wiki/Caffeic_acid" title="Caffeic acid">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 class="mw-selflink selflink">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?useformat=desktop&type=1x1&usesul3=0" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Myricetin&oldid=1275158738">https://en.wikipedia.org/w/index.php?title=Myricetin&oldid=1275158738</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Aromatase_inhibitors" title="Category:Aromatase inhibitors">Aromatase inhibitors</a></li><li><a href="/wiki/Category:Flavonols" title="Category:Flavonols">Flavonols</a></li><li><a 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