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</div> </a> <button aria-controls="toc-Genetic_and_physiological_diversity-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Genetic and physiological diversity subsection</span> </button> <ul id="toc-Genetic_and_physiological_diversity-sublist" class="vector-toc-list"> <li id="toc-Primates" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Primates"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Primates</span> </div> </a> <ul id="toc-Primates-sublist" class="vector-toc-list"> <li id="toc-Humans" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Humans"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1.1</span> <span>Humans</span> </div> </a> <ul id="toc-Humans-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Dogs" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Dogs"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Dogs</span> </div> </a> <ul id="toc-Dogs-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Birds,_reptiles_and_desert-dwelling_mammals" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Birds,_reptiles_and_desert-dwelling_mammals"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span>Birds, reptiles and desert-dwelling mammals</span> </div> </a> <ul id="toc-Birds,_reptiles_and_desert-dwelling_mammals-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Invertebrates" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Invertebrates"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.4</span> <span>Invertebrates</span> </div> </a> <ul id="toc-Invertebrates-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Bacteria" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Bacteria"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.5</span> <span>Bacteria</span> </div> </a> <ul id="toc-Bacteria-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Genetics" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Genetics"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Genetics</span> </div> </a> <ul id="toc-Genetics-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Clinical_significance_and_research" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Clinical_significance_and_research"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Clinical significance and research</span> </div> </a> <button aria-controls="toc-Clinical_significance_and_research-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Clinical significance and research subsection</span> </button> <ul id="toc-Clinical_significance_and_research-sublist" class="vector-toc-list"> <li id="toc-High_uric_acid" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#High_uric_acid"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>High uric acid</span> </div> </a> <ul id="toc-High_uric_acid-sublist" class="vector-toc-list"> <li id="toc-Gout" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Gout"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1.1</span> <span>Gout</span> </div> </a> <ul id="toc-Gout-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Tumor_lysis_syndrome" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Tumor_lysis_syndrome"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1.2</span> <span>Tumor lysis syndrome</span> </div> </a> <ul id="toc-Tumor_lysis_syndrome-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Lesch–Nyhan_syndrome" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Lesch–Nyhan_syndrome"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1.3</span> <span>Lesch–Nyhan syndrome</span> </div> </a> <ul id="toc-Lesch–Nyhan_syndrome-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cardiovascular_disease" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Cardiovascular_disease"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1.4</span> <span>Cardiovascular disease</span> </div> </a> <ul id="toc-Cardiovascular_disease-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Uric_acid_stone_formation" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Uric_acid_stone_formation"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1.5</span> <span>Uric acid stone formation</span> </div> </a> <ul id="toc-Uric_acid_stone_formation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Diabetes" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Diabetes"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1.6</span> <span>Diabetes</span> </div> </a> <ul id="toc-Diabetes-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Low_uric_acid" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Low_uric_acid"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>Low uric acid</span> </div> </a> <ul id="toc-Low_uric_acid-sublist" class="vector-toc-list"> <li id="toc-Multiple_sclerosis" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Multiple_sclerosis"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2.1</span> <span>Multiple sclerosis</span> </div> </a> <ul id="toc-Multiple_sclerosis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Normalizing_low_uric_acid" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Normalizing_low_uric_acid"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2.2</span> <span>Normalizing low uric acid</span> </div> </a> <ul id="toc-Normalizing_low_uric_acid-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Uric acid</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 63 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-63" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">63 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%AD%D9%85%D8%B6_%D8%A7%D9%84%D8%A8%D9%88%D9%84" title="حمض البول – Arabic" lang="ar" hreflang="ar" data-title="حمض البول" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%A7%D9%88%D8%B1%DB%8C%DA%A9_%D8%A7%D8%B3%DB%8C%D8%AF" title="اوریک اسید – South Azerbaijani" lang="azb" hreflang="azb" data-title="اوریک اسید" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%87%E0%A6%89%E0%A6%B0%E0%A6%BF%E0%A6%95_%E0%A6%85%E0%A7%8D%E0%A6%AF%E0%A6%BE%E0%A6%B8%E0%A6%BF%E0%A6%A1" title="ইউরিক অ্যাসিড – Bangla" lang="bn" hreflang="bn" data-title="ইউরিক অ্যাসিড" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%9C%D0%B0%D1%87%D0%B0%D0%B2%D0%B0%D1%8F_%D0%BA%D1%96%D1%81%D0%BB%D0%B0%D1%82%D0%B0" title="Мачавая кіслата – Belarusian" lang="be" hreflang="be" data-title="Мачавая кіслата" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%9F%D0%B8%D0%BA%D0%BE%D1%87%D0%BD%D0%B0_%D0%BA%D0%B8%D1%81%D0%B5%D0%BB%D0%B8%D0%BD%D0%B0" title="Пикочна киселина – Bulgarian" lang="bg" hreflang="bg" data-title="Пикочна киселина" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Mokra%C4%87na_kiselina" title="Mokraćna kiselina – Bosnian" lang="bs" hreflang="bs" data-title="Mokraćna kiselina" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/%C3%80cid_%C3%BAric" title="Àcid úric – Catalan" lang="ca" hreflang="ca" data-title="Àcid úric" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Kyselina_mo%C4%8Dov%C3%A1" title="Kyselina močová – Czech" lang="cs" hreflang="cs" data-title="Kyselina močová" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Asid_wrig" title="Asid wrig – Welsh" lang="cy" hreflang="cy" data-title="Asid wrig" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target"><span>Cymraeg</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Urinsyre" title="Urinsyre – Danish" lang="da" hreflang="da" data-title="Urinsyre" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Harns%C3%A4ure" title="Harnsäure – German" lang="de" hreflang="de" data-title="Harnsäure" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Kusihape" title="Kusihape – Estonian" lang="et" hreflang="et" data-title="Kusihape" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%9F%CF%85%CF%81%CE%B9%CE%BA%CF%8C_%CE%BF%CE%BE%CF%8D" title="Ουρικό οξύ – Greek" lang="el" hreflang="el" data-title="Ουρικό οξύ" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/%C3%81cido_%C3%BArico" title="Ácido úrico – Spanish" lang="es" hreflang="es" data-title="Ácido úrico" 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/Ureata_acido" title="Ureata acido – Esperanto" lang="eo" hreflang="eo" data-title="Ureata acido" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Azido_uriko" title="Azido uriko – Basque" lang="eu" hreflang="eu" data-title="Azido uriko" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A7%D9%88%D8%B1%DB%8C%DA%A9_%D8%A7%D8%B3%DB%8C%D8%AF" title="اوریک اسید – Persian" lang="fa" hreflang="fa" data-title="اوریک اسید" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Acide_urique" title="Acide urique – French" lang="fr" hreflang="fr" data-title="Acide urique" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Aig%C3%A9ad_%C3%BArach" title="Aigéad úrach – Irish" lang="ga" hreflang="ga" data-title="Aigéad úrach" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/%C3%81cido_%C3%BArico" title="Ácido úrico – Galician" lang="gl" hreflang="gl" data-title="Ácido úrico" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%9A%94%EC%82%B0" title="요산 – Korean" lang="ko" hreflang="ko" data-title="요산" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-ha mw-list-item"><a href="https://ha.wikipedia.org/wiki/Uric_acid" title="Uric acid – Hausa" lang="ha" hreflang="ha" data-title="Uric acid" data-language-autonym="Hausa" data-language-local-name="Hausa" class="interlanguage-link-target"><span>Hausa</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D5%84%D5%AB%D5%A6%D5%A1%D5%A9%D5%A9%D5%B8%D6%82" title="Միզաթթու – Armenian" lang="hy" hreflang="hy" data-title="Միզաթթու" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%AF%E0%A5%82%E0%A4%B0%E0%A4%BF%E0%A4%95_%E0%A4%85%E0%A4%AE%E0%A5%8D%E0%A4%B2" title="यूरिक अम्ल – Hindi" lang="hi" hreflang="hi" data-title="यूरिक अम्ल" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Mokra%C4%87na_kiselina" title="Mokraćna kiselina – Croatian" lang="hr" hreflang="hr" data-title="Mokraćna kiselina" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Asam_urat" title="Asam urat – Indonesian" lang="id" hreflang="id" data-title="Asam urat" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-is mw-list-item"><a href="https://is.wikipedia.org/wiki/%C3%9Evags%C3%BDra" title="Þvagsýra – Icelandic" lang="is" hreflang="is" data-title="Þvagsýra" data-language-autonym="Íslenska" data-language-local-name="Icelandic" class="interlanguage-link-target"><span>Íslenska</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Acido_urico" title="Acido urico – Italian" lang="it" hreflang="it" data-title="Acido urico" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%97%D7%95%D7%9E%D7%A6%D7%AA_%D7%A9%D7%AA%D7%9F" title="חומצת שתן – Hebrew" lang="he" hreflang="he" data-title="חומצת שתן" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Acidum_uricum" title="Acidum uricum – Latin" lang="la" hreflang="la" data-title="Acidum uricum" data-language-autonym="Latina" data-language-local-name="Latin" class="interlanguage-link-target"><span>Latina</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/%C5%A0lapimo_r%C5%ABg%C5%A1tis" title="Šlapimo rūgštis – Lithuanian" lang="lt" hreflang="lt" data-title="Šlapimo rūgštis" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/H%C3%BAgysav" title="Húgysav – Hungarian" lang="hu" hreflang="hu" data-title="Húgysav" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%9C%D0%BE%D1%87%D0%BD%D0%B0_%D0%BA%D0%B8%D1%81%D0%B5%D0%BB%D0%B8%D0%BD%D0%B0" title="Мочна киселина – Macedonian" lang="mk" hreflang="mk" data-title="Мочна киселина" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Asid_urik" title="Asid urik – Malay" lang="ms" hreflang="ms" data-title="Asid urik" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-min mw-list-item"><a href="https://min.wikipedia.org/wiki/Asam_urek" title="Asam urek – Minangkabau" lang="min" hreflang="min" data-title="Asam urek" data-language-autonym="Minangkabau" data-language-local-name="Minangkabau" class="interlanguage-link-target"><span>Minangkabau</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Urinezuur" title="Urinezuur – Dutch" lang="nl" hreflang="nl" data-title="Urinezuur" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ne mw-list-item"><a href="https://ne.wikipedia.org/wiki/%E0%A4%AF%E0%A5%81%E0%A4%B0%E0%A4%BF%E0%A4%95_%E0%A4%85%E0%A4%AE%E0%A5%8D%E0%A4%B2" title="युरिक अम्ल – Nepali" lang="ne" hreflang="ne" data-title="युरिक अम्ल" data-language-autonym="नेपाली" data-language-local-name="Nepali" class="interlanguage-link-target"><span>नेपाली</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E5%B0%BF%E9%85%B8" title="尿酸 – Japanese" lang="ja" hreflang="ja" data-title="尿酸" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Urinsyre" title="Urinsyre – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Urinsyre" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Acid_uric" title="Acid uric – Occitan" lang="oc" hreflang="oc" data-title="Acid uric" data-language-autonym="Occitan" data-language-local-name="Occitan" class="interlanguage-link-target"><span>Occitan</span></a></li><li class="interlanguage-link interwiki-nds mw-list-item"><a href="https://nds.wikipedia.org/wiki/Miegs%C3%BC%C3%BCr" title="Miegsüür – Low German" lang="nds" hreflang="nds" data-title="Miegsüür" data-language-autonym="Plattdüütsch" data-language-local-name="Low German" class="interlanguage-link-target"><span>Plattdüütsch</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Kwas_moczowy" title="Kwas moczowy – Polish" lang="pl" hreflang="pl" data-title="Kwas moczowy" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/%C3%81cido_%C3%BArico" title="Ácido úrico – Portuguese" lang="pt" hreflang="pt" data-title="Ácido úrico" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Acid_uric" title="Acid uric – Romanian" lang="ro" hreflang="ro" data-title="Acid uric" 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%BE%D1%87%D0%B5%D0%B2%D0%B0%D1%8F_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0" title="Мочевая кислота – Russian" lang="ru" hreflang="ru" data-title="Мочевая кислота" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Uric_acid" title="Uric acid – Simple English" lang="en-simple" hreflang="en-simple" data-title="Uric acid" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Kyselina_mo%C4%8Dov%C3%A1" title="Kyselina močová – Slovak" lang="sk" hreflang="sk" data-title="Kyselina močová" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Se%C4%8Dna_kislina" title="Sečna kislina – Slovenian" lang="sl" hreflang="sl" data-title="Sečna kislina" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Urinska_kiselina" title="Urinska kiselina – Serbian" lang="sr" hreflang="sr" data-title="Urinska kiselina" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Uri%C4%8Dna_kiselina" title="Urična kiselina – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Urična kiselina" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-su mw-list-item"><a href="https://su.wikipedia.org/wiki/Asam_urat" title="Asam urat – Sundanese" lang="su" hreflang="su" data-title="Asam urat" data-language-autonym="Sunda" data-language-local-name="Sundanese" class="interlanguage-link-target"><span>Sunda</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Virtsahappo" title="Virtsahappo – Finnish" lang="fi" hreflang="fi" data-title="Virtsahappo" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Urinsyra" title="Urinsyra – Swedish" lang="sv" hreflang="sv" data-title="Urinsyra" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%AF%E0%AF%82%E0%AE%B0%E0%AE%BF%E0%AE%95%E0%AF%8D_%E0%AE%85%E0%AE%AE%E0%AE%BF%E0%AE%B2%E0%AE%AE%E0%AF%8D" title="யூரிக் அமிலம் – Tamil" lang="ta" hreflang="ta" data-title="யூரிக் அமிலம்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B8%81%E0%B8%A3%E0%B8%94%E0%B8%A2%E0%B8%B9%E0%B8%A3%E0%B8%B4%E0%B8%81" title="กรดยูริก – Thai" lang="th" hreflang="th" data-title="กรดยูริก" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/%C3%9Crik_asit" title="Ürik asit – Turkish" lang="tr" hreflang="tr" data-title="Ürik asit" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%A1%D0%B5%D1%87%D0%BE%D0%B2%D0%B0_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0" title="Сечова кислота – Ukrainian" lang="uk" hreflang="uk" data-title="Сечова кислота" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-ur mw-list-item"><a href="https://ur.wikipedia.org/wiki/%DB%8C%D9%88%D8%B1%DA%A9_%D8%AA%DB%8C%D8%B2%D8%A7%D8%A8" title="یورک تیزاب – Urdu" lang="ur" hreflang="ur" data-title="یورک تیزاب" data-language-autonym="اردو" data-language-local-name="Urdu" class="interlanguage-link-target"><span>اردو</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Acid_uric" title="Acid uric – Vietnamese" lang="vi" hreflang="vi" data-title="Acid uric" 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class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Organic compound</div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/Uronic_acid" title="Uronic acid">uronic acid</a> or <a href="/wiki/Urea" title="Urea">urea</a>.</div> <p> <style data-mw-deduplicate="TemplateStyles:r1084375498">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> </p> <table class="infobox ib-chembox"> <caption>Uric acid </caption> <tbody><tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Harns%C3%A4ure_Ketoform.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9b/Harns%C3%A4ure_Ketoform.svg/110px-Harns%C3%A4ure_Ketoform.svg.png" decoding="async" width="110" height="78" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9b/Harns%C3%A4ure_Ketoform.svg/165px-Harns%C3%A4ure_Ketoform.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9b/Harns%C3%A4ure_Ketoform.svg/220px-Harns%C3%A4ure_Ketoform.svg.png 2x" data-file-width="220" data-file-height="156" /></a><figcaption></figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Uric_acid3D.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/85/Uric_acid3D.png/110px-Uric_acid3D.png" decoding="async" width="110" height="90" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/85/Uric_acid3D.png/165px-Uric_acid3D.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/85/Uric_acid3D.png/220px-Uric_acid3D.png 2x" data-file-width="1924" data-file-height="1576" /></a><figcaption></figcaption></figure> </td></tr></tbody></table> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">7,9-Dihydro-1<i>H</i>-purine-2,6,8(3<i>H</i>)-trione</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;">2,6,8-Trioxypurine; 2,6,8-Trihydroxypurine; 2,6,8-Trioxopurine; 1<i>H</i>-Purine-2,6,8-trione</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=69-93-2">69-93-2</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><a href="/wiki/Lactam" title="Lactam">lactam</a> form: <span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=O%3DC1Nc2nc%28%3DO%29nc2C%28%3DO%29N1">Interactive image</a></span></li><li>intermediate form: <span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=Oc0nc%28O%29nc1c0NC%28%3DO%29N1">Interactive image</a></span></li><li><a href="/wiki/Lactim" class="mw-redirect" title="Lactim">lactim</a> form: <span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=Oc0nc%28O%29nc1c0N%3DC%28O%29N1">Interactive image</a></span></li><li>urate monoanion: <span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=Oc0nc%28O%29nc1c0N%3DC%28%5BO-%5D%29N1">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td>3DMet </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.3dmet.dna.affrc.go.jp"><a rel="nofollow" class="external text" href="http://www.3dmet.dna.affrc.go.jp/cgi/show_data.php?acc=B00094">B00094</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Beilstein_database" title="Beilstein database">Beilstein Reference</a></div> </td> <td>156158 </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=27226">CHEBI:27226</a></span><sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL792">ChEMBL792</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.1142.html">1142</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/DB01696">DB01696</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.000.655">100.000.655</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q105522#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>200-720-7</li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/IUPHAR/BPS" class="mw-redirect" title="IUPHAR/BPS">IUPHAR/BPS</a></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.guidetopharmacology.org"><a rel="nofollow" class="external text" href="http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?tab=summary&ligandId=4731">4731</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C00366">C00366</a></span><sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Medical_Subject_Headings" title="Medical Subject Headings">MeSH</a> </td> <td><span title="www.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://www.nlm.nih.gov/cgi/mesh/2014/MB_cgi?mode=&term=Uric+Acid">Uric+Acid</a></span> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/1175">1175</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/268B43MJ25">268B43MJ25</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/DTXSID3042508">DTXSID3042508</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q105522#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C5H4N4O3/c10-3-1-2(7-4(11)6-1)8-5(12)9-3/h5,12H,(H,9,10)(H,7,8,11)<sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: DZGSAURIFGGOJK-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;"><a href="/wiki/Lactam" title="Lactam">lactam</a> form: O=C1Nc2nc(=O)nc2C(=O)N1</div></li><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%;">intermediate form: Oc0nc(O)nc1c0NC(=O)N1</div></li><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%;"><a href="/wiki/Lactim" class="mw-redirect" title="Lactim">lactim</a> form: Oc0nc(O)nc1c0N=C(O)N1</div></li><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%;">urate monoanion: Oc0nc(O)nc1c0N=C([O-])N1</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>5</sub><span title="Hydrogen">H</span><sub>4</sub><span title="Nitrogen">N</span><sub>4</sub><span title="Oxygen">O</span><sub>3</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002168112000000000♠"></span>168.112</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>White crystals </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>300 °C (572 °F; 573 K) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td>6 mg/100 mL (at 20 °C) </td></tr> <tr> <td><a href="/wiki/Partition_coefficient" title="Partition coefficient">log <i>P</i></a> </td> <td>−1.107 </td></tr> <tr> <td><a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">Acidity</a> (p<i>K</i><sub>a</sub>) </td> <td>5.6 </td></tr> <tr> <td><a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">Basicity</a> (p<i>K</i><sub>b</sub>) </td> <td>8.4 </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Magnetic_susceptibility" title="Magnetic susceptibility">Magnetic susceptibility</a> (χ)</div> </td> <td><span class="nowrap"><span data-sort-value="3004337999999999999♠"></span>−6.62<span style="margin-left:0.25em;margin-right:0.15em;">×</span>10<sup>−5</sup> cm<sup>3</sup> mol<sup>−1</sup></span> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Thermochemistry </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Heat_capacity" title="Heat capacity">Heat capacity</a> <span style="font-size:112%;">(<i>C</i>)</span></div> </td> <td>166.15 J K<sup>−1</sup> mol<sup>−1</sup> (at 24.0 °C) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Standard_molar_entropy" title="Standard molar entropy">Std molar<br />entropy</a> <span style="font-size:112%;">(<i>S</i><sup>⦵</sup><sub>298</sub>)</span></div> </td> <td>173.2 J K<sup>−1</sup> mol<sup>−1</sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Standard_enthalpy_change_of_formation" class="mw-redirect" title="Standard enthalpy change of formation">Std enthalpy of<br />formation</a> <span style="font-size:112%;">(Δ<sub>f</sub><i>H</i><sup>⦵</sup><sub>298</sub>)</span></div> </td> <td>−619.69 to −617.93 kJ mol<sup>−1</sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Standard_enthalpy_change_of_combustion" class="mw-redirect" title="Standard enthalpy change of combustion">Std enthalpy of<br />combustion</a> <span style="font-size:112%;">(Δ<sub>c</sub><i>H</i><sup>⦵</sup><sub>298</sub>)</span></div> </td> <td>−1921.2 to −1919.56 kJ mol<sup>−1</sup> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/12px-X_mark.svg.png" decoding="async" width="12" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/18px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/24px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=476995734&page2=Uric+acid">verify</a></span> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <sup><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup> ?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>Uric acid</b> is a <a href="/wiki/Heterocyclic_compound" title="Heterocyclic compound">heterocyclic compound</a> of <a href="/wiki/Carbon" title="Carbon">carbon</a>, <a href="/wiki/Nitrogen" title="Nitrogen">nitrogen</a>, <a href="/wiki/Oxygen" title="Oxygen">oxygen</a>, and <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> with the <a href="/wiki/Chemical_formula" title="Chemical formula">formula</a> C<sub>5</sub>H<sub>4</sub>N<sub>4</sub>O<sub>3</sub>. It forms ions and salts known as <b>urates</b> and <b>acid urates</b>, such as ammonium acid urate. Uric acid is a product of the metabolic breakdown of <a href="/wiki/Purine" title="Purine">purine</a> <a href="/wiki/Nucleotide" title="Nucleotide">nucleotides</a>, and it is a normal component of <a href="/wiki/Urine" title="Urine">urine</a>.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Hyperuricemia" title="Hyperuricemia">High blood concentrations of uric acid</a> can lead to <a href="/wiki/Gout" title="Gout">gout</a> and are associated with other medical conditions, including <a href="/wiki/Diabetes" title="Diabetes">diabetes</a> and the formation of ammonium acid urate <a href="/wiki/Kidney_stones" class="mw-redirect" title="Kidney stones">kidney stones</a>. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Uric_acid&action=edit&section=1" title="Edit section: Chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Uric acid was first isolated from <a href="/wiki/Kidney_stone" class="mw-redirect" title="Kidney stone">kidney stones</a> in 1776 by Swedish chemist <a href="/wiki/Carl_Wilhelm_Scheele" title="Carl Wilhelm Scheele">Carl Wilhelm Scheele</a>.<sup id="cite_ref-Scheele_2-0" class="reference"><a href="#cite_note-Scheele-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> In 1882, the Ukrainian chemist <a href="/wiki/Ivan_Horbaczewski" class="mw-redirect" title="Ivan Horbaczewski">Ivan Horbaczewski</a> first synthesized uric acid by melting <a href="/wiki/Urea" title="Urea">urea</a> with <a href="/wiki/Glycine" title="Glycine">glycine</a>.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>Uric acid displays lactam–lactim <a href="/wiki/Tautomerism" class="mw-redirect" title="Tautomerism">tautomerism</a>.<sup id="cite_ref-LiebermanMarks2007_4-0" class="reference"><a href="#cite_note-LiebermanMarks2007-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Uric acid crystallizes in the lactam form,<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> with <a href="/wiki/Computational_chemistry" title="Computational chemistry">computational chemistry</a> also indicating that tautomer to be the most stable.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Uric acid is a <a href="/wiki/Diprotic_acid" class="mw-redirect" title="Diprotic acid">diprotic acid</a> with <a href="/wiki/PKa" class="mw-redirect" title="PKa">p<i>K</i><sub>a1</sub></a> = 5.4 and p<i>K</i><sub>a2</sub> = 10.3.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> At physiological pH, urate predominates in solution.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)"><span title="Material near this tag needs references to reliable medical sources. (August 2024)">medical citation needed</span></a></i>]</sup> </p> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Harns%C3%A4ure_Ketoform.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9b/Harns%C3%A4ure_Ketoform.svg/200px-Harns%C3%A4ure_Ketoform.svg.png" decoding="async" width="200" height="142" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9b/Harns%C3%A4ure_Ketoform.svg/300px-Harns%C3%A4ure_Ketoform.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9b/Harns%C3%A4ure_Ketoform.svg/400px-Harns%C3%A4ure_Ketoform.svg.png 2x" data-file-width="220" data-file-height="156" /></a><figcaption>Lactam ion, a stable tautomer of uric acid</figcaption></figure> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Urat.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c0/Urat.svg/200px-Urat.svg.png" decoding="async" width="200" height="123" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c0/Urat.svg/300px-Urat.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c0/Urat.svg/400px-Urat.svg.png 2x" data-file-width="243" data-file-height="149" /></a><figcaption>Urate ion, a conjugate base of uric acid</figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Biochemistry">Biochemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Uric_acid&action=edit&section=2" title="Edit section: Biochemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The enzyme <a href="/wiki/Xanthine_oxidase" title="Xanthine oxidase">xanthine oxidase</a> (XO) <a href="/wiki/Catalysis" title="Catalysis">catalyzes</a> the formation of uric acid from <a href="/wiki/Xanthine" title="Xanthine">xanthine</a> and <a href="/wiki/Hypoxanthine" title="Hypoxanthine">hypoxanthine</a>. XO, which is found in mammals, functions primarily as a dehydrogenase and rarely as an oxidase, despite its name.<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> Xanthine in turn is produced from other <a href="/wiki/Purine" title="Purine">purines</a>. Xanthine oxidase is a large enzyme whose <a href="/wiki/Active_site" title="Active site">active site</a> consists of the metal <a href="/wiki/Molybdenum" title="Molybdenum">molybdenum</a> bound to <a href="/wiki/Sulfur" title="Sulfur">sulfur</a> and oxygen.<sup id="cite_ref-Hille_9-0" class="reference"><a href="#cite_note-Hille-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Uric acid is released in <a href="/wiki/Hypoxia_(medical)" class="mw-redirect" title="Hypoxia (medical)">hypoxic</a> conditions (low oxygen saturation).<sup id="cite_ref-Baillie_1473-1478_10-0" class="reference"><a href="#cite_note-Baillie_1473-1478-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Water_solubility">Water solubility</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Uric_acid&action=edit&section=3" title="Edit section: Water solubility"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In general, the water <a href="/wiki/Solubility" title="Solubility">solubility</a> of uric acid and its <a href="/wiki/Alkali_metal" title="Alkali metal">alkali metal</a> and <a href="/wiki/Alkaline_earth" class="mw-redirect" title="Alkaline earth">alkaline earth</a> <a href="/wiki/Salt_(chemistry)" title="Salt (chemistry)">salts</a> is rather low. All these salts exhibit greater solubility in hot water than cold, allowing for easy recrystallization. This low solubility is significant for the <a href="/wiki/Etiology" title="Etiology">etiology</a> of gout. The solubility of the acid and its salts in <a href="/wiki/Ethanol" title="Ethanol">ethanol</a> is very low or negligible. In ethanol/water mixtures, the solubilities are somewhere between the end values for pure ethanol and pure water.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)"><span title="Material near this tag needs references to reliable medical sources. (August 2024)">medical citation needed</span></a></i>]</sup> </p> <dl><dd><table class="wikitable sortable"> <caption>Solubility of urate salts (grams of water per gram of compound) </caption> <tbody><tr> <th data-sort-type="text">Compound </th> <th data-sort-type="number">Cold water </th> <th data-sort-type="number">Boiling water </th></tr> <tr> <td>Uric acid </td> <td align="right">15,000 </td> <td align="right">2,000 </td></tr> <tr> <td>Ammonium hydrogen urate </td> <td align="center">— </td> <td align="right">1,600 </td></tr> <tr> <td>Lithium hydrogen urate </td> <td align="right">370 </td> <td align="right">39 </td></tr> <tr> <td>Sodium hydrogen urate </td> <td align="right">1,175 </td> <td align="right">124 </td></tr> <tr> <td>Potassium hydrogen urate </td> <td align="right">790 </td> <td align="right">75 </td></tr> <tr> <td>Magnesium dihydrogen diurate </td> <td align="right">3,750 </td> <td align="right">160 </td></tr> <tr> <td>Calcium dihydrogen diurate </td> <td align="right">603 </td> <td align="right">276 </td></tr> <tr> <td>Disodium urate </td> <td align="right">77 </td> <td align="center">— </td></tr> <tr> <td>Dipotassium urate </td> <td align="right">44 </td> <td align="right">35 </td></tr> <tr> <td>Calcium urate </td> <td align="right">1,500 </td> <td align="right">1,440 </td></tr> <tr> <td>Strontium urate </td> <td align="right">4,300 </td> <td align="right">1,790 </td></tr> <tr> <td>Barium urate </td> <td align="right">7,900 </td> <td align="right">2,700 </td></tr></tbody></table></dd></dl> <p>The figures given indicate what mass of water is required to dissolve a unit mass of compound indicated. The lower the number, the more soluble the substance in the said solvent.<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><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><sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Genetic_and_physiological_diversity">Genetic and physiological diversity</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Uric_acid&action=edit&section=4" title="Edit section: Genetic and physiological diversity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Primates">Primates</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Uric_acid&action=edit&section=5" title="Edit section: Primates"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In <a href="/wiki/Humans" class="mw-redirect" title="Humans">humans</a> uric acid (actually hydrogen urate ion) is the final <a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">oxidation</a> (breakdown) product of <a href="/wiki/Purine_metabolism" title="Purine metabolism">purine metabolism</a> and is excreted in urine, whereas in most other <a href="/wiki/Mammal" title="Mammal">mammals</a>, the enzyme <a href="/wiki/Uricase" class="mw-redirect" title="Uricase">uricase</a> further oxidizes uric acid to <a href="/wiki/Allantoin" title="Allantoin">allantoin</a>.<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> The loss of uricase in higher primates parallels the similar loss of the ability to synthesize <a href="/wiki/Vitamin_C" title="Vitamin C">ascorbic acid</a>, leading to the suggestion that urate may partially substitute for ascorbate in such species.<sup id="cite_ref-Proct_15-0" class="reference"><a href="#cite_note-Proct-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> Both uric acid and ascorbic acid are strong <a href="/wiki/Reducing_agent" title="Reducing agent">reducing agents</a> (<a href="/wiki/Electron_donor" title="Electron donor">electron donors</a>) and potent <a href="/wiki/Antioxidant" title="Antioxidant">antioxidants</a>. In humans, over half the antioxidant capacity of <a href="/wiki/Blood_plasma" title="Blood plasma">blood plasma</a> comes from hydrogen urate ion.<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-heading4"><h4 id="Humans">Humans</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Uric_acid&action=edit&section=6" title="Edit section: Humans"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The normal concentration range of uric acid (or hydrogen urate ion) in human blood is 25 to 80 mg/L for men and 15 to 60 mg/L for women<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> (but see below for slightly different values). An individual can have serum values as high as 96 mg/L and not have gout.<sup id="cite_ref-hyperuricemia_18-0" class="reference"><a href="#cite_note-hyperuricemia-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> In humans, about 70% of daily uric acid disposal occurs via the kidneys, and in 5–25% of humans, impaired renal (kidney) excretion leads to <a href="/wiki/Hyperuricemia" title="Hyperuricemia">hyperuricemia</a>.<sup id="cite_ref-Vitart_2008_19-0" class="reference"><a href="#cite_note-Vitart_2008-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> Normal excretion of uric acid in the urine is 270 to 360 mg per day (concentration of 270 to 360 mg/L if one litre of urine is produced per day – higher than the solubility of uric acid because it is in the form of dissolved acid urates), roughly 1% as much as the daily excretion of <a href="/wiki/Urea" title="Urea">urea</a>.<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> </p> <div class="mw-heading mw-heading3"><h3 id="Dogs">Dogs</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Uric_acid&action=edit&section=7" title="Edit section: Dogs"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <a href="/wiki/Dalmatian_(dog)#Kidney_and_bladder_stones" class="mw-redirect" title="Dalmatian (dog)">Dalmatian</a> has a genetic defect in uric acid uptake by the <a href="/wiki/Liver" title="Liver">liver</a> and <a href="/wiki/Kidney" title="Kidney">kidneys</a>, resulting in decreased conversion to <a href="/wiki/Allantoin" title="Allantoin">allantoin</a>, so this breed excretes uric acid, and not allantoin, in the urine.<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-heading3"><h3 id="Birds,_reptiles_and_desert-dwelling_mammals"><span id="Birds.2C_reptiles_and_desert-dwelling_mammals"></span>Birds, reptiles and desert-dwelling mammals</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Uric_acid&action=edit&section=8" title="Edit section: Birds, reptiles and desert-dwelling mammals"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In <a href="/wiki/Bird" title="Bird">birds</a> and <a href="/wiki/Reptile" title="Reptile">reptiles</a>, and in some desert-dwelling mammals (such as the <a href="/wiki/Kangaroo_rat" title="Kangaroo rat">kangaroo rat</a>), uric acid also is the end product of purine metabolism, but it is excreted in <a href="/wiki/Feces" title="Feces">feces</a> as a dry mass. This involves a complex <a href="/wiki/Metabolic_pathway" title="Metabolic pathway">metabolic pathway</a> that is energetically costly in comparison to processing of other nitrogenous wastes such as <a href="/wiki/Urea" title="Urea">urea</a> (from the <a href="/wiki/Urea_cycle" title="Urea cycle">urea cycle</a>) or <a href="/wiki/Ammonia" title="Ammonia">ammonia</a>, but has the advantages of reducing water loss and preventing dehydration.<sup id="cite_ref-Hazard_22-0" class="reference"><a href="#cite_note-Hazard-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Invertebrates">Invertebrates</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Uric_acid&action=edit&section=9" title="Edit section: Invertebrates"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><i><a href="/wiki/Platynereis_dumerilii" title="Platynereis dumerilii">Platynereis dumerilii</a></i>, a marine <a href="/wiki/Polychaete" title="Polychaete">polychaete</a> worm, uses uric acid as a sexual <a href="/wiki/Pheromone" title="Pheromone">pheromone</a>. The female of the species releases uric acid into the water during <a href="/wiki/Mating" title="Mating">mating</a>, which induces males to release sperm.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Bacteria">Bacteria</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Uric_acid&action=edit&section=10" title="Edit section: Bacteria"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Uric acid metabolism is done in the human gut by ∼1/5 of bacteria species hat come from 4 of 6 major phyla. Such metabolism is anaerobic involving uncharacterized ammonia lyase, peptidase, carbamoyl transferase, and oxidoreductase enzymes. The result is that uric acid is converted into <a href="/wiki/Xanthine" title="Xanthine">xanthine</a> or <a href="/wiki/Lactic_acid" title="Lactic acid">lactate</a> and the <a href="/wiki/Short-chain_fatty_acid" title="Short-chain fatty acid">short chain fatty acids</a> such as <a href="/wiki/Acetate" title="Acetate">acetate</a> and <a href="/wiki/Butyric_acid" title="Butyric acid">butyrate</a>.<sup id="cite_ref-v435_24-0" class="reference"><a href="#cite_note-v435-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> Radioisotope studies suggest about 1/3 of uric acid is removed in healthy people in their gut with this being roughly 2/3 in those with kidney disease.<sup id="cite_ref-l551_25-0" class="reference"><a href="#cite_note-l551-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> In mouse models, such bacteria compensate for the loss of uricase leading researchers to raise the possibility "that antibiotics targeting anaerobic bacteria, which would ablate gut bacteria, increase the risk for developing gout in humans".<sup id="cite_ref-v435_24-1" class="reference"><a href="#cite_note-v435-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Genetics">Genetics</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Uric_acid&action=edit&section=11" title="Edit section: Genetics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Although foods such as meat and seafood can elevate serum urate levels, genetic variation is a much greater contributor to high serum urate.<sup id="cite_ref-pmid30305269_26-0" class="reference"><a href="#cite_note-pmid30305269-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid32620198_27-0" class="reference"><a href="#cite_note-pmid32620198-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> A proportion of people have mutations in the urate transport proteins responsible for the excretion of uric acid by the kidneys. Variants of a number of genes, linked to serum urate, have so far been identified: <i><a href="/wiki/SLC2A9" title="SLC2A9">SLC2A9</a></i>; <i><a href="/wiki/ABCG2" title="ABCG2">ABCG2</a></i>; <i><a href="/wiki/SLC17A1" class="mw-redirect" title="SLC17A1">SLC17A1</a></i>; <i><a href="/wiki/SLC22A11" title="SLC22A11">SLC22A11</a></i>; <i><a href="/wiki/SLC22A12" title="SLC22A12">SLC22A12</a></i>; <i><a href="/wiki/SLC16A9" class="mw-redirect" title="SLC16A9">SLC16A9</a></i>; <i><a href="/wiki/GCKR" class="mw-redirect" title="GCKR">GCKR</a></i>; <i><a href="/wiki/LRRC16A" class="mw-redirect" title="LRRC16A">LRRC16A</a></i>; and <i><a href="/wiki/PDZK1" title="PDZK1">PDZK1</a></i>.<sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Kolz_2009_29-0" class="reference"><a href="#cite_note-Kolz_2009-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> GLUT9, encoded by the <i>SLC2A9</i> gene, is known to transport both uric acid and <a href="/wiki/Fructose" title="Fructose">fructose</a>.<sup id="cite_ref-Vitart_2008_19-1" class="reference"><a href="#cite_note-Vitart_2008-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Döring_2008_31-0" class="reference"><a href="#cite_note-Döring_2008-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> </p><p>Myogenic <a href="/wiki/Hyperuricemia" title="Hyperuricemia">hyperuricemia</a>, as a result of the <a href="/wiki/Purine_nucleotide_cycle" title="Purine nucleotide cycle">purine nucleotide cycle</a> running when ATP reservoirs in muscle cells are low, is a common pathophysiologic feature of <a href="/wiki/Glycogen_storage_disease" title="Glycogen storage disease">glycogenoses</a>, such as <a href="/wiki/Glycogen_storage_disease_type_III" title="Glycogen storage disease type III">GSD-III</a>, which is a <a href="/wiki/Metabolic_myopathy" title="Metabolic myopathy">metabolic myopathy</a> impairing the ability of ATP (energy) production for muscle cells.<sup id="cite_ref-:0_33-0" class="reference"><a href="#cite_note-:0-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> In these metabolic myopathies, myogenic hyperuricemia is exercise-induced; inosine, hypoxanthine and uric acid increase in plasma after exercise and decrease over hours with rest.<sup id="cite_ref-:0_33-1" class="reference"><a href="#cite_note-:0-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> Excess AMP (adenosine monophosphate) is converted into uric acid.<sup id="cite_ref-:0_33-2" class="reference"><a href="#cite_note-:0-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> </p><p>AMP → IMP → Inosine → Hypoxanthine → Xanthine → Uric Acid<sup id="cite_ref-:0_33-3" class="reference"><a href="#cite_note-:0-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Clinical_significance_and_research">Clinical significance and research</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Uric_acid&action=edit&section=12" title="Edit section: Clinical significance and research"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In human <a href="/wiki/Blood_plasma" title="Blood plasma">blood plasma</a>, the <a href="/wiki/Reference_ranges_for_blood_tests#Other_electrolytes_and_metabolites" title="Reference ranges for blood tests">reference range</a> of uric acid is typically 3.4–7.2 mg per 100 mL(200–430 μmol/L) for men, and 2.4–6.1 mg per 100 mL for women (140–360 μmol/L).<sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> Uric acid concentrations in blood plasma above and below the normal range are known as, respectively, <a href="/wiki/Hyperuricemia" title="Hyperuricemia">hyperuricemia</a> and <a href="/wiki/Hypouricemia" title="Hypouricemia">hypouricemia</a>. Likewise, uric acid concentrations in urine above and below normal are known as <a href="/wiki/Hyperuricosuria" title="Hyperuricosuria">hyperuricosuria</a> and hypouricosuria. Uric acid levels in saliva may be associated with blood uric acid levels.<sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="High_uric_acid">High uric acid</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Uric_acid&action=edit&section=13" title="Edit section: High uric acid"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Hyperuricemia" title="Hyperuricemia">Hyperuricemia</a> (high levels of uric acid), which induces <a href="/wiki/Gout" title="Gout">gout</a>, has various potential origins: </p> <ul><li>Diet may be a factor. High intake of dietary <a href="/wiki/Purine" title="Purine">purine</a>, <a href="/wiki/High-fructose_corn_syrup" title="High-fructose corn syrup">high-fructose corn syrup</a>, and <a href="/wiki/Table_sugar" class="mw-redirect" title="Table sugar">sucrose</a> can increase levels of uric acid.<sup id="cite_ref-Cirillo_36-0" class="reference"><a href="#cite_note-Cirillo-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Theodore_37-0" class="reference"><a href="#cite_note-Theodore-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup></li> <li>Serum uric acid can be elevated by reduced excretion via the <a href="/wiki/Kidney" title="Kidney">kidneys</a>.<sup id="cite_ref-Mayo_38-0" class="reference"><a href="#cite_note-Mayo-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup></li> <li>Fasting or rapid weight loss can temporarily elevate uric acid levels.<sup id="cite_ref-pmid7024153_39-0" class="reference"><a href="#cite_note-pmid7024153-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup></li> <li>Certain drugs, such as <a href="/wiki/Thiazide" title="Thiazide">thiazide</a> diuretics, can increase blood uric acid levels by interfering with <a href="/wiki/Clearance_(medicine)" class="mw-redirect" title="Clearance (medicine)">renal clearance</a>.<sup id="cite_ref-40" class="reference"><a href="#cite_note-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Tumor_lysis_syndrome" title="Tumor lysis syndrome">Tumor lysis syndrome</a>, a metabolic complication of certain cancers or chemotherapy, due to <a href="/wiki/Nucleobase" class="mw-redirect" title="Nucleobase">nucleobase</a> and potassium release into the plasma.<sup id="cite_ref-howard_41-0" class="reference"><a href="#cite_note-howard-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Pseudohypoxia" title="Pseudohypoxia">Pseudohypoxia</a> (disrupted NADH/NAD<sup>+</sup> ratio) caused by diabetic hyperglycemia and excessive alcohol consumption.<sup id="cite_ref-42" class="reference"><a href="#cite_note-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup></li></ul> <div class="mw-heading mw-heading4"><h4 id="Gout">Gout</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Uric_acid&action=edit&section=14" title="Edit section: Gout"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Gout" title="Gout">Gout</a></div> <p>A 2011 survey in the United States indicated that 3.9% of the population had gout, whereas 21.4% had hyperuricemia without having symptoms.<sup id="cite_ref-pmid30485934_43-0" class="reference"><a href="#cite_note-pmid30485934-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> </p><p>Excess blood uric acid (serum urate) can induce <a href="/wiki/Gout" title="Gout">gout</a>,<sup id="cite_ref-Heinig_M,_Johnson_RJ_2006_1059–64_44-0" class="reference"><a href="#cite_note-Heinig_M,_Johnson_RJ_2006_1059–64-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> a painful condition resulting from needle-like crystals of uric acid termed <i>monosodium urate crystals</i><sup id="cite_ref-Abhishek_45-0" class="reference"><a href="#cite_note-Abhishek-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> precipitating in <a href="/wiki/Joint" title="Joint">joints</a>, <a href="/wiki/Capillary" title="Capillary">capillaries</a>, <a href="/wiki/Skin" title="Skin">skin</a>, and other tissues.<sup id="cite_ref-Lancet2010_46-0" class="reference"><a href="#cite_note-Lancet2010-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> Gout can occur where serum uric acid levels are as low as 6 mg per 100 mL (357 μmol/L), but an individual can have serum values as high as 9.6 mg per 100 mL (565 μmol/L) and not have gout.<sup id="cite_ref-hyperuricemia_18-1" class="reference"><a href="#cite_note-hyperuricemia-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p><p>In humans, purines are metabolized into uric acid, which is then excreted in the urine. Consumption of large amounts of some types of purine-rich foods, particularly meat and seafood, increases gout risk.<sup id="cite_ref-Choi_47-0" class="reference"><a href="#cite_note-Choi-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> Purine-rich foods include liver, kidney, and <a href="/wiki/Sweetbread" title="Sweetbread">sweetbreads</a>, and certain types of seafood, including anchovies, herring, sardines, mussels, scallops, trout, haddock, mackerel, and tuna.<sup id="cite_ref-48" class="reference"><a href="#cite_note-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> Moderate intake of purine-rich vegetables, however, is not associated with an increased risk of gout.<sup id="cite_ref-Choi_47-1" class="reference"><a href="#cite_note-Choi-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> </p><p>One treatment for gout in the 19th century was administration of <a href="/wiki/Lithium" title="Lithium">lithium</a> salts;<sup id="cite_ref-49" class="reference"><a href="#cite_note-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> lithium urate is more soluble. Today, inflammation during attacks is more commonly treated with <a href="/wiki/NSAID" class="mw-redirect" title="NSAID">NSAIDs</a>, <a href="/wiki/Colchicine" title="Colchicine">colchicine</a>, or <a href="/wiki/Corticosteroid" title="Corticosteroid">corticosteroids</a>, and urate levels are managed with <a href="/wiki/Allopurinol" title="Allopurinol">allopurinol</a>.<sup id="cite_ref-50" class="reference"><a href="#cite_note-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup> Allopurinol, which weakly inhibits xanthine oxidase, is an analog of hypoxanthine that is hydroxylated by <a href="/wiki/Xanthine_oxidase" title="Xanthine oxidase">xanthine oxidoreductase</a> at the 2-position to give oxipurinol.<sup id="cite_ref-51" class="reference"><a href="#cite_note-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Tumor_lysis_syndrome">Tumor lysis syndrome</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Uric_acid&action=edit&section=15" title="Edit section: Tumor lysis syndrome"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Tumor_lysis_syndrome" title="Tumor lysis syndrome">Tumor lysis syndrome</a>, an emergency condition that may result from <a href="/wiki/Blood_cancer" class="mw-redirect" title="Blood cancer">blood cancers</a>, produces high uric acid levels in blood when tumor cells release their contents into the blood, either spontaneously or following <a href="/wiki/Chemotherapy" title="Chemotherapy">chemotherapy</a>.<sup id="cite_ref-howard_41-1" class="reference"><a href="#cite_note-howard-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> Tumor lysis syndrome may lead to <a href="/wiki/Acute_kidney_injury" title="Acute kidney injury">acute kidney injury</a> when uric acid crystals are deposited in the kidneys.<sup id="cite_ref-howard_41-2" class="reference"><a href="#cite_note-howard-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> Treatment includes <a href="/wiki/Hyperhydration" class="mw-redirect" title="Hyperhydration">hyperhydration</a> to dilute and excrete uric acid via <a href="/wiki/Urine" title="Urine">urine</a>, <a href="/wiki/Rasburicase" title="Rasburicase">rasburicase</a> to reduce levels of poorly soluble uric acid in blood, or <a href="/wiki/Allopurinol" title="Allopurinol">allopurinol</a> to inhibit <a href="/wiki/Purine" title="Purine">purine</a> <a href="/wiki/Catabolism" title="Catabolism">catabolism</a> from adding to uric acid levels.<sup id="cite_ref-howard_41-3" class="reference"><a href="#cite_note-howard-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Lesch–Nyhan_syndrome"><span id="Lesch.E2.80.93Nyhan_syndrome"></span>Lesch–Nyhan syndrome</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Uric_acid&action=edit&section=16" title="Edit section: Lesch–Nyhan syndrome"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Lesch%E2%80%93Nyhan_syndrome" title="Lesch–Nyhan syndrome">Lesch–Nyhan syndrome</a>, a rare inherited disorder, is also associated with high serum uric acid levels.<sup id="cite_ref-52" class="reference"><a href="#cite_note-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> Spasticity, involuntary movement, and cognitive retardation as well as manifestations of gout are seen in this syndrome.<sup id="cite_ref-53" class="reference"><a href="#cite_note-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Cardiovascular_disease">Cardiovascular disease</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Uric_acid&action=edit&section=17" title="Edit section: Cardiovascular disease"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Hyperuricemia is associated with an increase in <a href="/wiki/Risk_factors" class="mw-redirect" title="Risk factors">risk factors</a> for <a href="/wiki/Cardiovascular_disease" title="Cardiovascular disease">cardiovascular disease</a>.<sup id="cite_ref-54" class="reference"><a href="#cite_note-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup> It is also possible that high levels of uric acid may have a causal role in the development of atherosclerotic cardiovascular disease, but this is controversial and the data are conflicting.<sup id="cite_ref-55" class="reference"><a href="#cite_note-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Uric_acid_stone_formation">Uric acid stone formation</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Uric_acid&action=edit&section=18" title="Edit section: Uric acid stone formation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Urine_crystals_comparison.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/17/Urine_crystals_comparison.png/220px-Urine_crystals_comparison.png" decoding="async" width="220" height="190" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/17/Urine_crystals_comparison.png/330px-Urine_crystals_comparison.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/17/Urine_crystals_comparison.png/440px-Urine_crystals_comparison.png 2x" data-file-width="1129" data-file-height="977" /></a><figcaption>Comparison of different types of urinary crystals.</figcaption></figure> <p><a href="/wiki/Kidney_stone" class="mw-redirect" title="Kidney stone">Kidney stones</a> can form through deposits of sodium urate microcrystals.<sup id="cite_ref-Banach_56-0" class="reference"><a href="#cite_note-Banach-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup> </p><p>Saturation levels of uric acid in blood may result in one form of <a href="/wiki/Kidney_stone" class="mw-redirect" title="Kidney stone">kidney stones</a> when the urate crystallizes in the kidney. These uric acid stones are <a href="/wiki/Radiodensity" title="Radiodensity">radiolucent</a>, so do not appear on an abdominal plain <a href="/wiki/X-ray" title="X-ray">X-ray</a>.<sup id="cite_ref-57" class="reference"><a href="#cite_note-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup> Uric acid crystals can also promote the formation of <a href="/wiki/Calcium_oxalate" title="Calcium oxalate">calcium oxalate</a> stones, acting as "seed crystals".<sup id="cite_ref-58" class="reference"><a href="#cite_note-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Diabetes">Diabetes</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Uric_acid&action=edit&section=19" title="Edit section: Diabetes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Hyperuricemia is associated with components of <a href="/wiki/Metabolic_syndrome" title="Metabolic syndrome">metabolic syndrome</a>, including in children.<sup id="cite_ref-59" class="reference"><a href="#cite_note-59"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-60" class="reference"><a href="#cite_note-60"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Low_uric_acid">Low uric acid</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Uric_acid&action=edit&section=20" title="Edit section: Low uric acid"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Low uric acid (<a href="/wiki/Hypouricemia" title="Hypouricemia">hypouricemia</a>) can have numerous causes. Low dietary <a href="/wiki/Zinc" title="Zinc">zinc</a> intakes cause lower uric acid levels. This effect can be even more pronounced in women taking oral contraceptive medication.<sup id="cite_ref-61" class="reference"><a href="#cite_note-61"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Sevelamer" title="Sevelamer">Sevelamer</a>, a drug indicated for prevention of <a href="/wiki/Hyperphosphataemia" class="mw-redirect" title="Hyperphosphataemia">hyperphosphataemia</a> in people with <a href="/wiki/Chronic_kidney_failure" class="mw-redirect" title="Chronic kidney failure">chronic kidney failure</a>, can significantly reduce serum uric acid.<sup id="cite_ref-62" class="reference"><a href="#cite_note-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Multiple_sclerosis">Multiple sclerosis</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Uric_acid&action=edit&section=21" title="Edit section: Multiple sclerosis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Meta-analysis" title="Meta-analysis">Meta-analysis</a> of 10 case-control studies found that the serum uric acid levels of patients with <a href="/wiki/Multiple_sclerosis" title="Multiple sclerosis">multiple sclerosis</a> were significantly lower compared to those of healthy controls, possibly indicating a diagnostic <a href="/wiki/Biomarker" title="Biomarker">biomarker</a> for multiple sclerosis.<sup id="cite_ref-63" class="reference"><a href="#cite_note-63"><span class="cite-bracket">[</span>63<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Normalizing_low_uric_acid">Normalizing low uric acid</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Uric_acid&action=edit&section=22" title="Edit section: Normalizing low uric acid"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Correcting low or deficient zinc levels can help elevate <a href="/wiki/Blood_serum" class="mw-redirect" title="Blood serum">serum</a> uric acid.<sup id="cite_ref-64" class="reference"><a href="#cite_note-64"><span class="cite-bracket">[</span>64<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Uric_acid&action=edit&section=23" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Theacrine" title="Theacrine">Theacrine</a> or 1,3,7,9-tetramethyluric acid, a purine alkaloid found in some teas</li> <li><a href="/wiki/Uracil" title="Uracil">Uracil</a> – <a href="/wiki/Purine" title="Purine">purine</a> <a href="/wiki/Nucleobase" class="mw-redirect" title="Nucleobase">nucleobase</a> named by Robert Behrend who was attempting to synthesize derivatives of uric acid</li> <li><a href="/wiki/Metabolic_myopathy" title="Metabolic myopathy">Metabolic myopathy</a></li> <li><a href="/wiki/Purine_nucleotide_cycle" title="Purine nucleotide cycle">Purine nucleotide cycle</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Uric_acid&action=edit&section=24" 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" style="column-width: 30em;"> <ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/Uric-Acid">"Uric Acid"</a>. <i>PubChem</i>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=PubChem&rft.atitle=Uric+Acid&rft_id=https%3A%2F%2Fpubchem.ncbi.nlm.nih.gov%2Fcompound%2FUric-Acid&rfr_id=info%3Asid%2Fen.wikipedia.org%3AUric+acid" class="Z3988"></span></span> </li> <li id="cite_note-Scheele-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-Scheele_2-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFScheele1776" class="citation journal cs1"><a href="/wiki/Carl_Wilhelm_Scheele" title="Carl Wilhelm Scheele">Scheele, C. W.</a> (1776). "Examen Chemicum Calculi Urinari" [A chemical examiniation of kidney stones]. <i>Opuscula</i>. <b>2</b>: 73.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Opuscula&rft.atitle=Examen+Chemicum+Calculi+Urinari&rft.volume=2&rft.pages=73&rft.date=1776&rft.aulast=Scheele&rft.aufirst=C.+W.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AUric+acid" class="Z3988"></span></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHorbaczewski1882" class="citation journal cs1">Horbaczewski, J. (1882). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=b448AAAAIAAJ&pg=PA796">"Synthese der Harnsäure"</a> [Synthesis of uric acid]. <i>Monatshefte für Chemie und Verwandte Teile Anderer Wissenschaften</i>. <b>3</b>: 796–797. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2FBF01516847">10.1007/BF01516847</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:92323943">92323943</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Monatshefte+f%C3%BCr+Chemie+und+Verwandte+Teile+Anderer+Wissenschaften&rft.atitle=Synthese+der+Harns%C3%A4ure&rft.volume=3&rft.pages=796-797&rft.date=1882&rft_id=info%3Adoi%2F10.1007%2FBF01516847&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A92323943%23id-name%3DS2CID&rft.aulast=Horbaczewski&rft.aufirst=J.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Db448AAAAIAAJ%26pg%3DPA796&rfr_id=info%3Asid%2Fen.wikipedia.org%3AUric+acid" class="Z3988"></span></span> </li> <li id="cite_note-LiebermanMarks2007-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-LiebermanMarks2007_4-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLiebermanMarksSmithMarks2007" class="citation book cs1">Lieberman, M.; Marks, A. D.; Smith, C. M.; Marks, D. B. (2007). <span class="id-lock-registration" title="Free registration required"><a rel="nofollow" class="external text" href="https://archive.org/details/marksessentialme0000lieb"><i>Marks' Essential Medical Biochemistry</i></a></span>. Philadelphia: Lippincott Williams & Wilkins. pp. <a rel="nofollow" class="external text" href="https://archive.org/details/marksessentialme0000lieb/page/47">47</a>–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-7817-9340-7" title="Special:BookSources/978-0-7817-9340-7"><bdi>978-0-7817-9340-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Marks%27+Essential+Medical+Biochemistry&rft.place=Philadelphia&rft.pages=47-&rft.pub=Lippincott+Williams+%26+Wilkins&rft.date=2007&rft.isbn=978-0-7817-9340-7&rft.aulast=Lieberman&rft.aufirst=M.&rft.au=Marks%2C+A.+D.&rft.au=Smith%2C+C.+M.&rft.au=Marks%2C+D.+B.&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Fmarksessentialme0000lieb&rfr_id=info%3Asid%2Fen.wikipedia.org%3AUric+acid" class="Z3988"></span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRingertz1966" class="citation journal cs1">Ringertz, H. (1 March 1966). <a rel="nofollow" class="external text" href="https://doi.org/10.1107%2FS0365110X66000914">"The molecular and crystal structure of uric acid"</a>. <i>Acta Crystallographica</i>. <b>20</b> (3): 397–403. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1966AcCry..20..397R">1966AcCry..20..397R</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1107%2FS0365110X66000914">10.1107/S0365110X66000914</a></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Acta+Crystallographica&rft.atitle=The+molecular+and+crystal+structure+of+uric+acid&rft.volume=20&rft.issue=3&rft.pages=397-403&rft.date=1966-03-01&rft_id=info%3Adoi%2F10.1107%2FS0365110X66000914&rft_id=info%3Abibcode%2F1966AcCry..20..397R&rft.aulast=Ringertz&rft.aufirst=H.&rft_id=https%3A%2F%2Fdoi.org%2F10.1107%252FS0365110X66000914&rfr_id=info%3Asid%2Fen.wikipedia.org%3AUric+acid" class="Z3988"></span></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJiménezAlderete2005" class="citation journal cs1">Jiménez, V.; Alderete, J. B. (November 2005). 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href="/wiki/Template:Nucleotide_metabolism_intermediates" title="Template:Nucleotide metabolism intermediates"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Nucleotide_metabolism_intermediates" title="Template talk:Nucleotide metabolism intermediates"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Nucleotide_metabolism_intermediates" title="Special:EditPage/Template:Nucleotide metabolism intermediates"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Nucleotide_metabolic_intermediates" style="font-size:114%;margin:0 4em"><a href="/wiki/Nucleotide" title="Nucleotide">Nucleotide</a> <a href="/wiki/Metabolic_intermediate" title="Metabolic intermediate">metabolic intermediates</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Purine_metabolism" title="Purine metabolism">purine<br />metabolism</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%">anabolism</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%"><i><span class="nobold"><a href="/wiki/Ribose_5-phosphate" title="Ribose 5-phosphate">R5P</a><b>→</b><a href="/wiki/Inosinic_acid" title="Inosinic acid">IMP</a>:</span></i></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/Ribose_5-phosphate" title="Ribose 5-phosphate">Ribose 5-phosphate</a> (R5P)</li> <li><a href="/wiki/Phosphoribosyl_pyrophosphate" title="Phosphoribosyl pyrophosphate">Phosphoribosyl pyrophosphate</a> (PRPP)</li> <li><a href="/wiki/Phosphoribosylamine" title="Phosphoribosylamine">Phosphoribosylamine</a> (PRA)</li> <li><a href="/wiki/Glycineamide_ribonucleotide" title="Glycineamide ribonucleotide">Glycineamide ribonucleotide</a> (GAR)</li> <li><a href="/wiki/Phosphoribosyl-N-formylglycineamide" title="Phosphoribosyl-N-formylglycineamide">Phosphoribosyl-N-formylglycineamide</a> (FGAR)</li> <li><a href="/wiki/5%E2%80%B2-Phosphoribosylformylglycinamidine" title="5′-Phosphoribosylformylglycinamidine">5′-Phosphoribosylformylglycinamidine</a> (FGAM)</li> <li><a href="/wiki/5-Aminoimidazole_ribotide" title="5-Aminoimidazole ribotide">5-Aminoimidazole ribotide</a> (AIR)</li> <li><a href="/wiki/5%E2%80%B2-Phosphoribosyl-4-carboxy-5-aminoimidazole" title="5′-Phosphoribosyl-4-carboxy-5-aminoimidazole">5′-Phosphoribosyl-4-carboxy-5-aminoimidazole</a> (CAIR)</li> <li><a href="/wiki/Phosphoribosylaminoimidazolesuccinocarboxamide" title="Phosphoribosylaminoimidazolesuccinocarboxamide">Phosphoribosylaminoimidazolesuccinocarboxamide</a> (SAICAR)</li> <li><a href="/wiki/AICA_ribonucleotide" title="AICA ribonucleotide">AICA ribonucleotide</a> (AICAR)</li> <li><a href="/wiki/5-Formamidoimidazole-4-carboxamide_ribotide" title="5-Formamidoimidazole-4-carboxamide ribotide">5-Formamidoimidazole-4-carboxamide ribotide</a> (FAICAR)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i><span class="nobold">IMP<b>→</b><a href="/wiki/Adenosine_monophosphate" title="Adenosine monophosphate">AMP</a>:</span></i></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"><a href="/wiki/Adenylosuccinate" title="Adenylosuccinate">Adenylosuccinate</a></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i><span class="nobold">IMP<b>→</b><a href="/wiki/Guanosine_monophosphate" title="Guanosine monophosphate">GMP</a>:</span></i></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"><a href="/wiki/Xanthosine_monophosphate" title="Xanthosine monophosphate">Xanthosine monophosphate</a></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">catabolism</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-Hydroxyisourate" title="5-Hydroxyisourate">5-Hydroxyisourate</a></li> <li><a href="/wiki/Hypoxanthine" title="Hypoxanthine">Hypoxanthine</a></li> <li><a class="mw-selflink selflink">Uric acid</a></li> <li><a href="/wiki/Xanthine" title="Xanthine">Xanthine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Pyrimidine_metabolism" title="Pyrimidine metabolism">pyrimidine<br />metabolism</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%">anabolism</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/Carbamoyl_aspartic_acid" title="Carbamoyl aspartic acid">Carbamoyl aspartic acid</a></li> <li><a href="/wiki/Carbamoyl_phosphate" title="Carbamoyl phosphate">Carbamoyl phosphate</a></li> <li><a href="/wiki/4,5-Dihydroorotic_acid" title="4,5-Dihydroorotic acid">4,5-Dihydroorotic acid</a></li> <li><a href="/wiki/Orotic_acid" title="Orotic acid">Orotic acid</a></li> <li><a href="/wiki/Orotidine_5%27-monophosphate" title="Orotidine 5'-monophosphate">Orotidine 5'-monophosphate</a></li> <li><a href="/wiki/Uridine_monophosphate" title="Uridine monophosphate">Uridine monophosphate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">catabolism</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%"><i><span class="nobold"><a href="/wiki/Uracil" title="Uracil">uracil</a>:</span></i></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/%CE%92-Alanine" title="Β-Alanine">β-Alanine</a></li> <li><a href="/wiki/Dihydrouracil" title="Dihydrouracil">Dihydrouracil</a></li> <li><a href="/wiki/3-Ureidopropionic_acid" title="3-Ureidopropionic acid">3-Ureidopropionic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i><span class="nobold"><a href="/wiki/Thymine" title="Thymine">thymine</a>:</span></i></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-Aminoisobutyric_acid" title="3-Aminoisobutyric acid">3-Aminoisobutyric acid</a></li> <li><a href="/wiki/Dihydrothymine" title="Dihydrothymine">Dihydrothymine</a></li> <li><a href="/wiki/Beta-Ureidoisobutyric_acid" class="mw-redirect" title="Beta-Ureidoisobutyric acid">β-Ureidoisobutyric acid</a></li></ul> </div></td></tr></tbody></table><div></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="Antioxidants" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Antioxidants" title="Template:Antioxidants"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Antioxidants" title="Template talk:Antioxidants"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Antioxidants" title="Special:EditPage/Template:Antioxidants"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Antioxidants" style="font-size:114%;margin:0 4em"><a href="/wiki/Antioxidant" title="Antioxidant">Antioxidants</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Food antioxidants</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/6-Hydroxymelatonin" title="6-Hydroxymelatonin">6-Hydroxymelatonin</a></li> <li><a href="/wiki/Acetylcarnitine" title="Acetylcarnitine">Acetyl-<small>L</small>-carnitine</a> (ALCAR)</li> <li><a href="/wiki/Lipoic_acid" title="Lipoic acid">Alpha-lipoic acid</a> (ALA)</li> <li><a href="/wiki/Vitamin_C" title="Vitamin C">Ascorbic acid</a> (vitamin C)</li> <li><a href="/wiki/Carotenoid" title="Carotenoid">Carotenoids</a> (<a href="/wiki/Vitamin_A" title="Vitamin A">vitamin A</a>)</li> <li><a href="/wiki/Curcumin" title="Curcumin">Curcumin</a></li> <li><a href="/wiki/Edaravone" title="Edaravone">Edaravone</a></li> <li><a href="/wiki/Antioxidant_effect_of_polyphenols_and_natural_phenols" title="Antioxidant effect of polyphenols and natural phenols">Polyphenols</a></li> <li><a href="/wiki/Glutathione" title="Glutathione">Glutathione</a></li> <li><a href="/wiki/Hydroxytyrosol" title="Hydroxytyrosol">Hydroxytyrosol</a></li> <li><a href="/wiki/Carnitine" title="Carnitine"><small>L</small>-carnitine</a></li> <li><a href="/wiki/Ladostigil" title="Ladostigil">Ladostigil</a></li> <li><a href="/wiki/Melatonin" title="Melatonin">Melatonin</a></li> <li><a href="/wiki/Mofegiline" title="Mofegiline">Mofegiline</a></li> <li><a href="/wiki/Acetylcysteine" title="Acetylcysteine"><i>N</i>-Acetylcysteine</a> (NAC)</li> <li><a href="/wiki/N-Acetylserotonin" title="N-Acetylserotonin"><i>N</i>-Acetylserotonin</a> (NAS)</li> <li><a href="/wiki/Oleocanthal" title="Oleocanthal">Oleocanthal</a></li> <li><a href="/wiki/Oleuropein" title="Oleuropein">Oleuropein</a></li> <li><a href="/wiki/Rasagiline" title="Rasagiline">Rasagiline</a></li> <li><a href="/wiki/Resveratrol" title="Resveratrol">Resveratrol</a></li> <li><a href="/wiki/Selegiline" title="Selegiline">Selegiline</a></li> <li><a href="/wiki/Selenium" title="Selenium">Selenium</a></li> <li><a href="/wiki/Tocopherol" title="Tocopherol">Tocopherols</a> (<a href="/wiki/Vitamin_E" title="Vitamin E">vitamin E</a>)</li> <li><a href="/wiki/Tocotrienol" title="Tocotrienol">Tocotrienols</a> (<a href="/wiki/Vitamin_E" title="Vitamin E">vitamin E</a>)</li> <li><a href="/wiki/Tyrosol" title="Tyrosol">Tyrosol</a></li> <li><a href="/wiki/Coenzyme_Q10" title="Coenzyme Q10">Ubiquinone</a> (coenzyme Q)</li> <li><a class="mw-selflink selflink">Uric acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Fuel antioxidants</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Butylated_hydroxyanisole" title="Butylated hydroxyanisole">Butylated hydroxyanisole</a></li> <li><a href="/wiki/Butylated_hydroxytoluene" title="Butylated hydroxytoluene">Butylated hydroxytoluene</a></li> <li><a href="/wiki/2,6-Di-tert-butylphenol" title="2,6-Di-tert-butylphenol">2,6-Di-<i>tert</i>-butylphenol</a></li> <li><a href="/wiki/1,2-Diaminopropane" title="1,2-Diaminopropane">1,2-Diaminopropane</a></li> <li><a href="/wiki/2,4-Dimethyl-6-tert-butylphenol" title="2,4-Dimethyl-6-tert-butylphenol">2,4-Dimethyl-6-<i>tert</i>-butylphenol</a></li> <li><a href="/wiki/Ethylenediamine" title="Ethylenediamine">Ethylenediamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Measurements</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Folin%E2%80%93Ciocalteu_reagent" title="Folin–Ciocalteu reagent">Folin method</a></li> <li><a href="/wiki/Oxygen_radical_absorbance_capacity" title="Oxygen radical absorbance capacity">ORAC</a></li> <li><a href="/wiki/Trolox_equivalent_antioxidant_capacity" title="Trolox equivalent antioxidant capacity">TEAC</a></li> <li><a href="/wiki/Ferric_reducing_ability_of_plasma" title="Ferric reducing ability of plasma">FRAP</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Purine_receptor_modulators" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Purine_receptor_modulators" title="Template:Purine receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Purine_receptor_modulators" title="Template talk:Purine receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Purine_receptor_modulators" title="Special:EditPage/Template:Purine receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Purine_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Purine_receptor" class="mw-redirect" title="Purine receptor">Purine receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Receptor_(biochemistry)" title="Receptor (biochemistry)">Receptor</a><br /><small>(<a href="/wiki/Ligand_(biochemistry)" title="Ligand (biochemistry)">ligands</a>)</small></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;"><a href="/wiki/P0_receptor" class="mw-redirect" title="P0 receptor">P0</a> (<a href="/wiki/Adenine" title="Adenine">adenine</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/w/index.php?title=8-Aminoadenine&action=edit&redlink=1" class="new" title="8-Aminoadenine (page does not exist)">8-Aminoadenine</a></li> <li><a href="/wiki/Adenine" title="Adenine">Adenine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;"><a href="/wiki/Adenosine_receptor" title="Adenosine receptor">P1</a><br />(<a href="/wiki/Adenosine" title="Adenosine">adenosine</a>)</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/w/index.php?title=2-(1-Hexynyl)-N-methyladenosine&action=edit&redlink=1" class="new" title="2-(1-Hexynyl)-N-methyladenosine (page does not exist)">2-(1-Hexynyl)-<i>N</i>-methyladenosine</a></li> <li><a href="/w/index.php?title=2-Cl-IB-MECA&action=edit&redlink=1" class="new" title="2-Cl-IB-MECA (page does not exist)">2-Cl-IB-MECA</a></li> <li><a href="/w/index.php?title=2-Chloroadenosine&action=edit&redlink=1" class="new" title="2-Chloroadenosine (page does not exist)">2-Chloroadenosine</a></li> <li><a href="/w/index.php?title=2%27-MeCCPA&action=edit&redlink=1" class="new" title="2'-MeCCPA (page does not exist)">2'-MeCCPA</a></li> <li><a href="/w/index.php?title=4%27-O-%CE%B2-D-Glucosyl-9-O-(6%27-deoxysaccharosyl)olivil&action=edit&redlink=1" class="new" title="4'-O-β-D-Glucosyl-9-O-(6'-deoxysaccharosyl)olivil (page does not exist)">4'-O-β-D-Glucosyl-9-O-(6''-deoxysaccharosyl)olivil</a></li> <li><a href="/w/index.php?title=5%27-N-ethylcarboxamidoadenosine&action=edit&redlink=1" class="new" title="5'-N-ethylcarboxamidoadenosine (page does not exist)">5'-<i>N</i>-ethylcarboxamidoadenosine</a></li> <li><a href="/wiki/Adenosine" title="Adenosine">Adenosine</a></li> <li><a href="/wiki/Adenosine_diphosphate" title="Adenosine diphosphate">ADP</a></li> <li><a href="/wiki/Adenosine_monophosphate" title="Adenosine monophosphate">AMP</a></li> <li><a href="/w/index.php?title=Apadenoson&action=edit&redlink=1" class="new" title="Apadenoson (page does not exist)">Apadenoson</a></li> <li><a href="/wiki/ATL-146e" class="mw-redirect" title="ATL-146e">ATL-146e</a></li> <li><a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a></li> <li><a href="/wiki/BAY_60%E2%80%936583" title="BAY 60–6583">BAY 60–6583</a></li> <li><a href="/w/index.php?title=Binodenoson&action=edit&redlink=1" class="new" title="Binodenoson (page does not exist)">Binodenoson</a></li> <li><a href="/w/index.php?title=Capadenoson&action=edit&redlink=1" class="new" title="Capadenoson (page does not exist)">Capadenoson</a></li> <li><a href="/wiki/CCPA_(biochemistry)" title="CCPA (biochemistry)">CCPA</a></li> <li><a href="/wiki/CGS-21680" title="CGS-21680">CGS-21680</a></li> <li><a href="/wiki/CP-532,903" title="CP-532,903">CP-532,903</a></li> <li><a href="/w/index.php?title=CV-1808&action=edit&redlink=1" class="new" title="CV-1808 (page does not exist)">CV-1808</a></li> <li><a href="/w/index.php?title=Evodenoson&action=edit&redlink=1" class="new" title="Evodenoson (page does not exist)">Evodenoson</a></li> <li><a href="/w/index.php?title=GR_79236&action=edit&redlink=1" class="new" title="GR 79236 (page does not exist)">GR 79236</a></li> <li><a href="/w/index.php?title=HENECA&action=edit&redlink=1" class="new" title="HENECA (page does not exist)">HENECA</a></li> <li><a href="/w/index.php?title=LUF-5835&action=edit&redlink=1" class="new" title="LUF-5835 (page does not exist)">LUF-5835</a></li> <li><a href="/w/index.php?title=LUF-5845&action=edit&redlink=1" class="new" title="LUF-5845 (page does not exist)">LUF-5845</a></li> <li><a href="/wiki/N6-Cyclopentyladenosine" title="N6-Cyclopentyladenosine"><i>N</i><sup>6</sup>-Cyclopentyladenosine</a></li> <li><a href="/wiki/Namodenoson" title="Namodenoson">Namodenoson</a></li> <li><a href="/w/index.php?title=NECA_(drug)&action=edit&redlink=1" class="new" title="NECA (drug) (page does not exist)">NECA</a></li> <li><a href="/w/index.php?title=Neladenoson_dalanate&action=edit&redlink=1" class="new" title="Neladenoson dalanate (page does not exist)">Neladenoson dalanate</a></li> <li><a href="/w/index.php?title=Piclidenoson&action=edit&redlink=1" class="new" title="Piclidenoson (page does not exist)">Piclidenoson</a></li> <li><a href="/wiki/Regadenoson" title="Regadenoson">Regadenoson</a></li> <li><a href="/w/index.php?title=SDZ_WAG_994&action=edit&redlink=1" class="new" title="SDZ WAG 994 (page does not exist)">SDZ WAG 994</a></li> <li><a href="/w/index.php?title=Selodenoson&action=edit&redlink=1" class="new" title="Selodenoson (page does not exist)">Selodenoson</a></li> <li><a href="/w/index.php?title=Sonedenoson&action=edit&redlink=1" class="new" title="Sonedenoson (page does not exist)">Sonedenoson</a></li> <li><a href="/w/index.php?title=Tecadenoson&action=edit&redlink=1" class="new" title="Tecadenoson (page does not exist)">Tecadenoson</a></li> <li><a href="/w/index.php?title=Trabodenoson&action=edit&redlink=1" class="new" title="Trabodenoson (page does not exist)">Trabodenoson</a></li> <li><a href="/wiki/UK-432,097" title="UK-432,097">UK-432,097</a></li></ul> <ul><li><b>Antagonists:</b> <a href="/wiki/3-Chlorostyrylcaffeine" title="3-Chlorostyrylcaffeine">3-Chlorostyrylcaffeine (CSC)</a></li> <li><a href="/wiki/7-Methylxanthine" title="7-Methylxanthine">7-Methylxanthine</a></li> <li><a href="/wiki/8-Chlorotheophylline" title="8-Chlorotheophylline">8-Chlorotheophylline</a></li> <li><a href="/w/index.php?title=8-Phenyl-1,3-dipropylxanthine&action=edit&redlink=1" class="new" title="8-Phenyl-1,3-dipropylxanthine (page does not exist)">8-Phenyl-1,3-dipropylxanthine</a></li> <li><a href="/wiki/8-Phenyltheophylline" title="8-Phenyltheophylline">8-Phenyltheophylline</a></li> <li><a href="/wiki/Acefylline" title="Acefylline">Acefylline</a></li> <li><a href="/wiki/Aminophylline" title="Aminophylline">Aminophylline</a></li> <li><a href="/wiki/ATL-444" title="ATL-444">ATL-444</a></li> <li><a href="/w/index.php?title=AZD-4635&action=edit&redlink=1" class="new" title="AZD-4635 (page does not exist)">AZD-4635</a></li> <li><a href="/wiki/Bamifylline" title="Bamifylline">Bamifylline</a></li> <li><a href="/wiki/Cafedrine" title="Cafedrine">Cafedrine</a></li> <li><a href="/wiki/Caffeine" title="Caffeine">Caffeine</a></li> <li><a href="/wiki/Caffeine_citrate" title="Caffeine citrate">Caffeine citrate</a></li> <li><a href="/wiki/Cartazolate" title="Cartazolate">Cartazolate</a></li> <li><a href="/w/index.php?title=CGH-2466&action=edit&redlink=1" class="new" title="CGH-2466 (page does not exist)">CGH-2466</a></li> <li><a href="/wiki/CGS-15943" title="CGS-15943">CGS-15943</a></li> <li><a href="/wiki/Choline_theophyllinate" title="Choline theophyllinate">Choline theophyllinate</a></li> <li><a href="/w/index.php?title=Ciforadenant&action=edit&redlink=1" class="new" title="Ciforadenant (page does not exist)">Ciforadenant</a></li> <li><a href="/wiki/8-Cyclopentyl-1,3-dimethylxanthine" title="8-Cyclopentyl-1,3-dimethylxanthine">CPX</a></li> <li><a href="/w/index.php?title=CVT-6883&action=edit&redlink=1" class="new" title="CVT-6883 (page does not exist)">CVT-6883</a></li> <li><a href="/wiki/Dimethazan" title="Dimethazan">Dimethazan</a></li> <li><a href="/wiki/DMPX" title="DMPX">DMPX</a></li> <li><a href="/wiki/8-Cyclopentyl-1,3-dipropylxanthine" class="mw-redirect" title="8-Cyclopentyl-1,3-dipropylxanthine">DPCPX</a></li> <li><a href="/wiki/Dyphylline" class="mw-redirect" title="Dyphylline">Dyphylline</a></li> <li><a href="/wiki/Enprofylline" title="Enprofylline">Enprofylline</a></li> <li><a href="/wiki/Etazolate" title="Etazolate">Etazolate</a></li> <li><a href="/w/index.php?title=Etrumadenant&action=edit&redlink=1" class="new" title="Etrumadenant (page does not exist)">Etrumadenant</a></li> <li><a href="/wiki/Fenethylline" title="Fenethylline">Fenethylline</a></li> <li><a href="/wiki/IBMX" title="IBMX">IBMX</a></li> <li><a href="/w/index.php?title=Imaradenant&action=edit&redlink=1" class="new" title="Imaradenant (page does not exist)">Imaradenant</a></li> <li><a href="/w/index.php?title=Inupadenant&action=edit&redlink=1" class="new" title="Inupadenant (page does not exist)">Inupadenant</a></li> <li><a href="/wiki/ISAM-140" title="ISAM-140">ISAM-140</a></li> <li><a href="/w/index.php?title=ISAM-R316&action=edit&redlink=1" class="new" title="ISAM-R316 (page does not exist)">ISAM-R316</a></li> <li><a href="/wiki/Isovaleric_acid" title="Isovaleric acid">Isovaleric acid</a></li> <li><a href="/wiki/Istradefylline" title="Istradefylline">Istradefylline</a></li> <li><a href="/wiki/KF-26777" title="KF-26777">KF-26777</a></li> <li><a href="/wiki/Lu_AA41063" title="Lu AA41063">Lu AA41063</a></li> <li><a href="/wiki/Lu_AA47070" title="Lu AA47070">Lu AA47070</a></li> <li><a href="/wiki/MRE3008F20" class="mw-redirect" title="MRE3008F20">MRE3008F20</a></li> <li><a href="/wiki/MRS-1191" class="mw-redirect" title="MRS-1191">MRS-1191</a></li> <li><a href="/w/index.php?title=MRS-1220&action=edit&redlink=1" class="new" title="MRS-1220 (page does not exist)">MRS-1220</a></li> <li><a href="/w/index.php?title=MRS-1334&action=edit&redlink=1" class="new" title="MRS-1334 (page does not exist)">MRS-1334</a></li> <li><a href="/wiki/MRS-1523" class="mw-redirect" title="MRS-1523">MRS-1523</a></li> <li><a href="/wiki/MRS-1706" title="MRS-1706">MRS-1706</a></li> <li><a href="/w/index.php?title=MRS-1754&action=edit&redlink=1" class="new" title="MRS-1754 (page does not exist)">MRS-1754</a></li> <li><a href="/w/index.php?title=MRS-3777&action=edit&redlink=1" class="new" title="MRS-3777 (page does not exist)">MRS-3777</a></li> <li><a href="/wiki/MSX-2" title="MSX-2">MSX-2</a></li> <li><a href="/wiki/MSX-3" title="MSX-3">MSX-3</a></li> <li><a href="/wiki/MSX-4" title="MSX-4">MSX-4</a></li> <li><a href="/w/index.php?title=Muvadenant&action=edit&redlink=1" class="new" title="Muvadenant (page does not exist)">Muvadenant</a></li> <li><a href="/wiki/Paraxanthine" title="Paraxanthine">Paraxanthine</a></li> <li><a href="/wiki/Pentoxifylline" title="Pentoxifylline">Pentoxifylline</a></li> <li><a href="/wiki/Preladenant" title="Preladenant">Preladenant</a></li> <li><a href="/wiki/Propentofylline" title="Propentofylline">Propentofylline</a></li> <li><a href="/wiki/Proxyphylline" title="Proxyphylline">Proxyphylline</a></li> <li><a href="/wiki/PSB-10" title="PSB-10">PSB-10</a></li> <li><a href="/w/index.php?title=PSB-11&action=edit&redlink=1" class="new" title="PSB-11 (page does not exist)">PSB-11</a></li> <li><a href="/w/index.php?title=PSB-36&action=edit&redlink=1" class="new" title="PSB-36 (page does not exist)">PSB-36</a></li> <li><a href="/w/index.php?title=PSB-603&action=edit&redlink=1" class="new" title="PSB-603 (page does not exist)">PSB-603</a></li> <li><a href="/w/index.php?title=PSB-788&action=edit&redlink=1" class="new" title="PSB-788 (page does not exist)">PSB-788</a></li> <li><a href="/w/index.php?title=PSB-1115&action=edit&redlink=1" class="new" title="PSB-1115 (page does not exist)">PSB-1115</a></li> <li><a href="/w/index.php?title=PSB-1901&action=edit&redlink=1" class="new" title="PSB-1901 (page does not exist)">PSB-1901</a></li> <li><a href="/wiki/Reversine" title="Reversine">Reversine</a></li> <li><a href="/wiki/Rolofylline" title="Rolofylline">Rolofylline</a></li> <li><a href="/wiki/SCH-442,416" title="SCH-442,416">SCH-442,416</a></li> <li><a href="/wiki/SCH-58261" title="SCH-58261">SCH-58261</a></li> <li><a href="/w/index.php?title=Sipagladenant&action=edit&redlink=1" class="new" title="Sipagladenant (page does not exist)">Sipagladenant</a></li> <li><a href="/w/index.php?title=Taminadenant&action=edit&redlink=1" class="new" title="Taminadenant (page does not exist)">Taminadenant</a></li> <li><a href="/wiki/Theacrine" title="Theacrine">Theacrine</a></li> <li><a href="/wiki/Theobromine" title="Theobromine">Theobromine</a></li> <li><a href="/wiki/Theodrenaline" title="Theodrenaline">Theodrenaline</a></li> <li><a href="/wiki/Theophylline" title="Theophylline">Theophylline</a></li> <li><a href="/w/index.php?title=Tozadenant&action=edit&redlink=1" class="new" title="Tozadenant (page does not exist)">Tozadenant</a></li> <li><a href="/wiki/Tracazolate" title="Tracazolate">Tracazolate</a></li> <li><a href="/w/index.php?title=Vipadenant&action=edit&redlink=1" class="new" title="Vipadenant (page does not exist)">Vipadenant</a></li> <li><a href="/w/index.php?title=VUF-5574&action=edit&redlink=1" class="new" title="VUF-5574 (page does not exist)">VUF-5574</a></li> <li><a href="/wiki/ZM-241,385" title="ZM-241,385">ZM-241,385</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;"><a href="/wiki/P2_receptor" title="P2 receptor">P2</a><br />(<a href="/wiki/Nucleotide" title="Nucleotide">nucleotide</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:3em;;text-align:center;"><a href="/wiki/P2X_purinoreceptor" title="P2X purinoreceptor">P2X</a><br />(<a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate"><abbr title="Adenosine triphosphate">ATP</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Adenosine triphosphate</span>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/w/index.php?title=2-Methylthio-ATP&action=edit&redlink=1" class="new" title="2-Methylthio-ATP (page does not exist)">2-Me-SATP</a></li> <li><a href="/w/index.php?title=%CE%91,%CE%B2-Methylene-ATP&action=edit&redlink=1" class="new" title="Α,β-Methylene-ATP (page does not exist)">α,β-Me-ATP</a></li> <li><a href="/wiki/Adenosine" title="Adenosine">Adenosine</a></li> <li><a href="/wiki/Adenosine_diphosphate" title="Adenosine diphosphate">ADP</a></li> <li><a href="/wiki/Adenosine_monophosphate" title="Adenosine monophosphate">AMP</a></li> <li><a href="/wiki/Diadenosine_tetraphosphate" class="mw-redirect" title="Diadenosine tetraphosphate">Ap4A</a></li> <li><a href="/w/index.php?title=Diadenosine_pentaphosphate&action=edit&redlink=1" class="new" title="Diadenosine pentaphosphate (page does not exist)">Ap5A</a></li> <li><a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a></li> <li><a href="/w/index.php?title=Adenosine-5%27-(%CE%B3-thio)-triphosphate&action=edit&redlink=1" class="new" title="Adenosine-5'-(γ-thio)-triphosphate (page does not exist)">ATPγS</a></li> <li><a href="/w/index.php?title=BzATP&action=edit&redlink=1" class="new" title="BzATP (page does not exist)">BzATP</a></li> <li><a href="/w/index.php?title=Cibacron_blue&action=edit&redlink=1" class="new" title="Cibacron blue (page does not exist)">Cibacron blue</a></li> <li><a href="/wiki/Cytidine_triphosphate" title="Cytidine triphosphate">CTP</a></li> <li><a href="/w/index.php?title=D-%CE%B2,%CE%B3-Me-ATP&action=edit&redlink=1" class="new" title="D-β,γ-Me-ATP (page does not exist)">D-β,γ-Me-ATP</a></li> <li><a href="/wiki/Guanosine_triphosphate" title="Guanosine triphosphate">GTP</a></li> <li><a href="/w/index.php?title=HT-AMP&action=edit&redlink=1" class="new" title="HT-AMP (page does not exist)">HT-AMP</a></li> <li><a href="/wiki/Ivermectin" title="Ivermectin">Ivermectin</a></li> <li><a href="/w/index.php?title=L-%CE%B2,%CE%B3-Me-ATP&action=edit&redlink=1" class="new" title="L-β,γ-Me-ATP (page does not exist)">L-β,γ-Me-ATP</a></li> <li><a href="/w/index.php?title=MRS-2219&action=edit&redlink=1" class="new" title="MRS-2219 (page does not exist)">MRS-2219</a></li> <li><a href="/w/index.php?title=PAPET-ATP&action=edit&redlink=1" class="new" title="PAPET-ATP (page does not exist)">PAPET-ATP</a></li> <li><a href="/wiki/Uridine_triphosphate" title="Uridine triphosphate">UTP</a></li> <li><a href="/wiki/Zinc" title="Zinc">Zinc</a></li></ul> <ul><li><b>Antagonists:</b> <a href="/w/index.php?title=5-BDBD&action=edit&redlink=1" class="new" title="5-BDBD (page does not exist)">5-BDBD</a></li> <li><a href="/w/index.php?title=A-317491&action=edit&redlink=1" class="new" title="A-317491 (page does not exist)">A-317491</a></li> <li><a href="/w/index.php?title=A-438079&action=edit&redlink=1" class="new" title="A-438079 (page does not exist)">A-438079</a></li> <li><a href="/w/index.php?title=A-740003&action=edit&redlink=1" class="new" title="A-740003 (page does not exist)">A-740003</a></li> <li><a href="/w/index.php?title=A-804598&action=edit&redlink=1" class="new" title="A-804598 (page does not exist)">A-804598</a></li> <li><a href="/w/index.php?title=A-839977&action=edit&redlink=1" class="new" title="A-839977 (page does not exist)">A-839977</a></li> <li><a href="/wiki/AF-353" title="AF-353">AF-353</a></li> <li><a href="/w/index.php?title=AZ-10606120&action=edit&redlink=1" class="new" title="AZ-10606120 (page does not exist)">AZ-10606120</a></li> <li><a href="/w/index.php?title=AZ-11645373&action=edit&redlink=1" class="new" title="AZ-11645373 (page does not exist)">AZ-11645373</a></li> <li><a href="/wiki/Brilliant_Blue_G" class="mw-redirect" title="Brilliant Blue G">BBG</a></li> <li><a href="/wiki/Calcium" title="Calcium">Calcium</a></li> <li><a href="/w/index.php?title=Calmidazolium&action=edit&redlink=1" class="new" title="Calmidazolium (page does not exist)">Calmidazolium</a></li> <li><a href="/wiki/Chelerythrine" title="Chelerythrine">Chelerythrine</a></li> <li><a href="/wiki/Copper" title="Copper">Copper</a></li> <li><a href="/wiki/Emodin" title="Emodin">Emodin</a> (<i><a href="/wiki/Rheum_officinale" title="Rheum officinale">Rheum officinale</a></i>)</li> <li><a href="/wiki/Evans_blue_(dye)" title="Evans blue (dye)">Evans blue</a></li> <li><a href="/wiki/Gefapixant" title="Gefapixant">Gefapixant</a></li> <li><a href="/w/index.php?title=GW-791343&action=edit&redlink=1" class="new" title="GW-791343 (page does not exist)">GW-791343</a></li> <li><a href="/w/index.php?title=5-(N,N-Hexamethylene)amiloride&action=edit&redlink=1" class="new" title="5-(N,N-Hexamethylene)amiloride (page does not exist)">HMA</a></li> <li><a href="/w/index.php?title=Diinosine_pentaphosphate&action=edit&redlink=1" class="new" title="Diinosine pentaphosphate (page does not exist)">Ip5I</a></li> <li><a href="/w/index.php?title=IsoPPADS&action=edit&redlink=1" class="new" title="IsoPPADS (page does not exist)">isoPPADS</a></li> <li><a href="/w/index.php?title=JNJ-47965567&action=edit&redlink=1" class="new" title="JNJ-47965567 (page does not exist)">JNJ-47965567</a></li> <li><a href="/w/index.php?title=KN-04&action=edit&redlink=1" class="new" title="KN-04 (page does not exist)">KN-04</a></li> <li><a href="/wiki/KN-62" title="KN-62">KN-62</a></li> <li><a href="/wiki/Magnesium" title="Magnesium">Magnesium</a></li> <li><a href="/w/index.php?title=MRS-2159&action=edit&redlink=1" class="new" title="MRS-2159 (page does not exist)">MRS-2159</a></li> <li><a href="/w/index.php?title=NF-023&action=edit&redlink=1" class="new" title="NF-023 (page does not exist)">NF-023</a></li> <li><a href="/w/index.php?title=NF-110&action=edit&redlink=1" class="new" title="NF-110 (page does not exist)">NF-110</a></li> <li><a href="/w/index.php?title=NF-157&action=edit&redlink=1" class="new" title="NF-157 (page does not exist)">NF-157</a></li> <li><a href="/w/index.php?title=NF-279&action=edit&redlink=1" class="new" title="NF-279 (page does not exist)">NF-279</a></li> <li><a href="/w/index.php?title=NF-449&action=edit&redlink=1" class="new" title="NF-449 (page does not exist)">NF-449</a></li> <li><a href="/wiki/Opiranserin" title="Opiranserin">Opiranserin (VVZ-149)</a></li> <li><a href="/w/index.php?title=Oxidized-ATP&action=edit&redlink=1" class="new" title="Oxidized-ATP (page does not exist)">Oxidized-ATP</a></li> <li><a href="/wiki/Phenol_Red" class="mw-redirect" title="Phenol Red">Phenol Red</a></li> <li><a href="/wiki/Phenolphthalein" title="Phenolphthalein">Phenolphthalein</a></li> <li><a href="/wiki/PPADS" title="PPADS">PPADS</a></li> <li><a href="/w/index.php?title=PPNDS&action=edit&redlink=1" class="new" title="PPNDS (page does not exist)">PPNDS</a></li> <li><a href="/w/index.php?title=PSB-12062&action=edit&redlink=1" class="new" title="PSB-12062 (page does not exist)">PSB-12062</a></li> <li><a href="/wiki/Puerarin" title="Puerarin">Puerarin</a> (<i><a href="/wiki/Radix_puerariae" class="mw-redirect" title="Radix puerariae">Radix puerariae</a></i>)</li> <li><a href="/w/index.php?title=Purotoxin_1&action=edit&redlink=1" class="new" title="Purotoxin 1 (page does not exist)">Purotoxin 1</a></li> <li><a href="/w/index.php?title=Reactive_Blue_2&action=edit&redlink=1" class="new" title="Reactive Blue 2 (page does not exist)">RB-2</a></li> <li><a href="/w/index.php?title=Ro_0437626&action=edit&redlink=1" class="new" title="Ro 0437626 (page does not exist)">Ro 0437626</a></li> <li><a href="/w/index.php?title=Ro_51&action=edit&redlink=1" class="new" title="Ro 51 (page does not exist)">Ro 51</a></li> <li><a href="/w/index.php?title=RO-3&action=edit&redlink=1" class="new" title="RO-3 (page does not exist)">RO-3</a></li> <li><a href="/wiki/Sodium_ferulate" title="Sodium ferulate">Sodium ferulate</a> (<i><a href="/wiki/Angelica_sinensis" title="Angelica sinensis">Angelica sinensis</a></i>, <i><a href="/wiki/Ligusticum_wallichii" class="mw-redirect" title="Ligusticum wallichii">Ligusticum wallichii</a></i>)</li> <li><a href="/wiki/Suramin" title="Suramin">Suramin</a></li> <li><a href="/w/index.php?title=TC-P_262&action=edit&redlink=1" class="new" title="TC-P 262 (page does not exist)">TC-P 262</a></li> <li><a href="/wiki/Tetramethylpyrazine" title="Tetramethylpyrazine">Tetramethylpyrazine (ligustrazine)</a> (<i><a href="/wiki/Ligusticum_wallichii" class="mw-redirect" title="Ligusticum wallichii">Ligusticum wallichii</a></i>)</li> <li><a href="/wiki/TNP-ATP" title="TNP-ATP">TNP-ATP</a></li> <li><a href="/wiki/Zinc" title="Zinc">Zinc</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:3em;;text-align:center;"><a href="/wiki/P2Y_receptor" title="P2Y receptor">P2Y</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/w/index.php?title=2-Methylthioladenosine_diphosphate&action=edit&redlink=1" class="new" title="2-Methylthioladenosine diphosphate (page does not exist)">2-Me-SADP</a></li> <li><a href="/w/index.php?title=2-Methylthioadenosine_triphosphate&action=edit&redlink=1" class="new" title="2-Methylthioadenosine triphosphate (page does not exist)">2-Me-SATP</a></li> <li><a href="/w/index.php?title=2-Thio-UTP&action=edit&redlink=1" class="new" title="2-Thio-UTP (page does not exist)">2-Thio-UTP</a></li> <li><a href="/w/index.php?title=5-Bromouridine_5%E2%80%B2-diphosphate&action=edit&redlink=1" class="new" title="5-Bromouridine 5′-diphosphate (page does not exist)">5-Br-UDP</a></li> <li><a href="/w/index.php?title=5-OMe-UDP&action=edit&redlink=1" class="new" title="5-OMe-UDP (page does not exist)">5-OMe-UDP</a></li> <li><a href="/w/index.php?title=%CE%91,%CE%B2-Methylene-ATP&action=edit&redlink=1" class="new" title="Α,β-Methylene-ATP (page does not exist)">α,β-Me-ATP</a></li> <li><a href="/wiki/Adenosine" title="Adenosine">Adenosine</a></li> <li><a href="/wiki/Adenosine_diphosphate" title="Adenosine diphosphate">ADP</a></li> <li><a href="/w/index.php?title=Adenosine-5%27-(%CE%B2-thio)-diphosphate&action=edit&redlink=1" class="new" title="Adenosine-5'-(β-thio)-diphosphate (page does not exist)">ADPβS</a></li> <li><a href="/w/index.php?title=Diadenosine_triphosphate&action=edit&redlink=1" class="new" title="Diadenosine triphosphate (page does not exist)">Ap3A</a></li> <li><a href="/w/index.php?title=AR-C_67085MX&action=edit&redlink=1" class="new" title="AR-C 67085MX (page does not exist)">AR-C 67085MX</a></li> <li><a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a></li> <li><a href="/w/index.php?title=Adenosine-5%27-(%CE%B3-thio)-triphosphate&action=edit&redlink=1" class="new" title="Adenosine-5'-(γ-thio)-triphosphate (page does not exist)">ATPγS</a></li> <li><a href="/wiki/Cytidine_triphosphate" title="Cytidine triphosphate">CTP</a></li> <li><a href="/wiki/Deoxyadenosine_triphosphate" title="Deoxyadenosine triphosphate">dATP</a></li> <li><a href="/wiki/Denufosol" title="Denufosol">Denufosol</a></li> <li><a href="/wiki/Diquafosol" title="Diquafosol">Diquafosol</a></li> <li><a href="/w/index.php?title=Inosine_diphosphate&action=edit&redlink=1" class="new" title="Inosine diphosphate (page does not exist)">IDP</a></li> <li><a href="/wiki/Inosine_triphosphate" title="Inosine triphosphate">ITP</a></li> <li><a href="/wiki/INS-365" class="mw-redirect" title="INS-365">INS-365</a></li> <li><a href="/w/index.php?title=INS-37217&action=edit&redlink=1" class="new" title="INS-37217 (page does not exist)">INS-37217</a></li> <li><a href="/w/index.php?title=MRS-2365&action=edit&redlink=1" class="new" title="MRS-2365 (page does not exist)">MRS-2365</a></li> <li><a href="/w/index.php?title=MRS-2690&action=edit&redlink=1" class="new" title="MRS-2690 (page does not exist)">MRS-2690</a></li> <li><a href="/w/index.php?title=MRS-2693&action=edit&redlink=1" class="new" title="MRS-2693 (page does not exist)">MRS-2693</a></li> <li><a href="/w/index.php?title=MRS-2768&action=edit&redlink=1" class="new" title="MRS-2768 (page does not exist)">MRS-2768</a></li> <li><a href="/w/index.php?title=MRS-2957&action=edit&redlink=1" class="new" title="MRS-2957 (page does not exist)">MRS-2957</a></li> <li><a href="/w/index.php?title=MRS-4062&action=edit&redlink=1" class="new" title="MRS-4062 (page does not exist)">MRS-4062</a></li> <li><a href="/w/index.php?title=NF-546&action=edit&redlink=1" class="new" title="NF-546 (page does not exist)">NF-546</a></li> <li><a href="/w/index.php?title=PAPET-ATP&action=edit&redlink=1" class="new" title="PAPET-ATP (page does not exist)">PAPET-ATP</a></li> <li><a href="/w/index.php?title=PSB-0474&action=edit&redlink=1" class="new" title="PSB-0474 (page does not exist)">PSB-0474</a></li> <li><a href="/w/index.php?title=PSB-1114&action=edit&redlink=1" class="new" title="PSB-1114 (page does not exist)">PSB-1114</a></li> <li><a href="/wiki/Uridine_diphosphate" title="Uridine diphosphate">UDP</a></li> <li><a href="/w/index.php?title=Uridine_5%C2%B4-(%CE%B2-thio)-diphosphate&action=edit&redlink=1" class="new" title="Uridine 5´-(β-thio)-diphosphate (page does not exist)">UDPβS</a></li> <li><a href="/wiki/Uridine_diphosphate_galactose" title="Uridine diphosphate galactose">UDP-galactose</a></li> <li><a href="/wiki/Uridine_diphosphate_glucose" title="Uridine diphosphate glucose">UDP-glucose</a></li> <li><a href="/wiki/Uridine_diphosphate_N-acetylglucosamine" title="Uridine diphosphate N-acetylglucosamine">UDP-N-acetylglucosamine</a></li> <li><a href="/w/index.php?title=Diuridine_triphosphate&action=edit&redlink=1" class="new" title="Diuridine triphosphate (page does not exist)">Up3U</a></li> <li><a href="/wiki/Uridine_triphosphate" title="Uridine triphosphate">UTP</a></li> <li><a href="/w/index.php?title=Uridine-5%27-(%CE%B3-thio)-triphosphate&action=edit&redlink=1" class="new" title="Uridine-5'-(γ-thio)-triphosphate (page does not exist)">UTPγS</a></li></ul> <ul><li><b>Antagonists:</b> <a href="/w/index.php?title=2-Methylthioladenosine_monophosphate&action=edit&redlink=1" class="new" title="2-Methylthioladenosine monophosphate (page does not exist)">2-Me-SAMP</a></li> <li><a href="/w/index.php?title=A3P5PS&action=edit&redlink=1" class="new" title="A3P5PS (page does not exist)">A3P5PS</a></li> <li><a href="/w/index.php?title=AMP%CE%B1S&action=edit&redlink=1" class="new" title="AMPαS (page does not exist)">AMPαS</a></li> <li><a href="/wiki/Diadenosine_tetraphosphate" class="mw-redirect" title="Diadenosine tetraphosphate">Ap4A</a></li> <li><a href="/w/index.php?title=AR-C_66096&action=edit&redlink=1" class="new" title="AR-C 66096 (page does not exist)">AR-C 66096</a></li> <li><a href="/w/index.php?title=AR-C_67085MX&action=edit&redlink=1" class="new" title="AR-C 67085MX (page does not exist)">AR-C 67085MX</a></li> <li><a href="/w/index.php?title=AR-C_69931MX&action=edit&redlink=1" class="new" title="AR-C 69931MX (page does not exist)">AR-C 69931MX</a></li> <li><a href="/w/index.php?title=AR-C_118925XX&action=edit&redlink=1" class="new" title="AR-C 118925XX (page does not exist)">AR-C 118925XX</a></li> <li><a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a></li> <li><a href="/w/index.php?title=BzATP&action=edit&redlink=1" class="new" title="BzATP (page does not exist)">BzATP</a></li> <li><a href="/w/index.php?title=C1330-7&action=edit&redlink=1" class="new" title="C1330-7 (page does not exist)">C1330-7</a></li> <li><a href="/wiki/Cangrelor" title="Cangrelor">Cangrelor</a></li> <li><a href="/wiki/Clopidogrel" title="Clopidogrel">Clopidogrel</a></li> <li><a href="/wiki/Elinogrel" title="Elinogrel">Elinogrel</a></li> <li><a href="/w/index.php?title=Diinosine_pentaphosphate&action=edit&redlink=1" class="new" title="Diinosine pentaphosphate (page does not exist)">Ip5I</a></li> <li><a href="/w/index.php?title=MRS-2179&action=edit&redlink=1" class="new" title="MRS-2179 (page does not exist)">MRS-2179</a></li> <li><a href="/w/index.php?title=MRS-2211&action=edit&redlink=1" class="new" title="MRS-2211 (page does not exist)">MRS-2211</a></li> <li><a href="/w/index.php?title=MRS-2279&action=edit&redlink=1" class="new" title="MRS-2279 (page does not exist)">MRS-2279</a></li> <li><a href="/w/index.php?title=MRS-2395&action=edit&redlink=1" class="new" title="MRS-2395 (page does not exist)">MRS-2395</a></li> <li><a href="/w/index.php?title=MRS-2500&action=edit&redlink=1" class="new" title="MRS-2500 (page does not exist)">MRS-2500</a></li> <li><a href="/w/index.php?title=MRS-2578&action=edit&redlink=1" class="new" title="MRS-2578 (page does not exist)">MRS-2578</a></li> <li><a href="/w/index.php?title=NF-157&action=edit&redlink=1" class="new" title="NF-157 (page does not exist)">NF-157</a></li> <li><a href="/w/index.php?title=NF-340&action=edit&redlink=1" class="new" title="NF-340 (page does not exist)">NF-340</a></li> <li><a href="/w/index.php?title=2,2%27-Pyridylisatogen_tosylate&action=edit&redlink=1" class="new" title="2,2'-Pyridylisatogen tosylate (page does not exist)">PIT</a></li> <li><a href="/wiki/PPADS" title="PPADS">PPADS</a></li> <li><a href="/wiki/Prasugrel" title="Prasugrel">Prasugrel</a></li> <li><a href="/w/index.php?title=PSB-0739&action=edit&redlink=1" class="new" title="PSB-0739 (page does not exist)">PSB-0739</a></li> <li><a href="/w/index.php?title=Reactive_Blue_2&action=edit&redlink=1" class="new" title="Reactive Blue 2 (page does not exist)">RB-2</a></li> <li><a href="/wiki/Regrelor" title="Regrelor">Regrelor</a></li> <li><a href="/wiki/Suramin" title="Suramin">Suramin</a></li> <li><a href="/wiki/Ticagrelor" title="Ticagrelor">Ticagrelor</a></li> <li><a href="/wiki/Ticlopidine" title="Ticlopidine">Ticlopidine</a></li> <li><a href="/wiki/Uridine_diphosphate" title="Uridine diphosphate">UDP</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Membrane_transport_protein" title="Membrane transport protein">Transporter</a><br /><small>(<a href="/wiki/Reuptake_inhibitor" title="Reuptake inhibitor">blockers</a>)</small></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;"><a href="/wiki/Concentrative_nucleoside_transporters" class="mw-redirect" title="Concentrative nucleoside transporters"><abbr title="Concentrative nucleoside transporters">CNTs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Concentrative nucleoside transporters</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=6-Hydroxy-7-methoxyflavone&action=edit&redlink=1" class="new" title="6-Hydroxy-7-methoxyflavone (page does not exist)">6-Hydroxy-7-methoxyflavone</a></li> <li><a href="/wiki/Adenosine" title="Adenosine">Adenosine</a></li> <li><a href="/w/index.php?title=DMeThPmR&action=edit&redlink=1" class="new" title="DMeThPmR (page does not exist)">dMeThPmR</a></li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a></li> <li><a href="/w/index.php?title=KGO-2142&action=edit&redlink=1" class="new" title="KGO-2142 (page does not exist)">KGO-2142</a></li> <li><a href="/w/index.php?title=KGO-2173&action=edit&redlink=1" class="new" title="KGO-2173 (page does not exist)">KGO-2173</a></li> <li><a href="/w/index.php?title=MeThPmR&action=edit&redlink=1" class="new" title="MeThPmR (page does not exist)">MeThPmR</a></li> <li><a href="/wiki/Phloridzin" class="mw-redirect" title="Phloridzin">Phloridzin</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;"><a href="/wiki/Equilibrative_nucleoside_transporters" class="mw-redirect" title="Equilibrative nucleoside transporters"><abbr title="Equilibrative nucleoside transporters">ENTs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Equilibrative nucleoside transporters</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Barbiturate" title="Barbiturate">Barbiturates</a></li> <li><a href="/wiki/Benzodiazepine" title="Benzodiazepine">Benzodiazepines</a></li> <li><a href="/wiki/Cilostazol" title="Cilostazol">Cilostazol</a></li> <li><a href="/wiki/Dilazep" title="Dilazep">Dilazep</a></li> <li><a href="/wiki/Dipyridamole" title="Dipyridamole">Dipyridamole</a></li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a></li> <li><a href="/wiki/Ethanol" title="Ethanol">Ethanol</a></li> <li><a href="/wiki/Hexobendine" title="Hexobendine">Hexobendine</a></li> <li><a href="/w/index.php?title=6-S-((4-Nitrophenyl)methyl)-6-thioinosine&action=edit&redlink=1" class="new" title="6-S-((4-Nitrophenyl)methyl)-6-thioinosine (page does not exist)">NBMPR</a></li> <li><a href="/wiki/Pentoxifylline" title="Pentoxifylline">Pentoxifylline</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li> <li><a href="/wiki/Propentofylline" title="Propentofylline">Propentofylline</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;"><a href="/wiki/Plasma_membrane_monoamine_transporter" title="Plasma membrane monoamine transporter"><abbr title="Plasma membrane monoamine transporter">PMAT</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Plasma membrane monoamine transporter</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Decynium-22" title="Decynium-22">Decynium-22</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Enzyme" title="Enzyme">Enzyme</a><br /><small>(<a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">inhibitors</a>)</small></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;"><a href="/wiki/Xanthine_oxidase" title="Xanthine oxidase"><abbr title="Xanthine oxidase">XO</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Xanthine oxidase</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Allopurinol" title="Allopurinol">Allopurinol</a></li> <li><a href="/wiki/Amflutizole" title="Amflutizole">Amflutizole</a></li> <li><a href="/wiki/Benzbromarone" title="Benzbromarone">Benzbromarone</a></li> <li><a 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 href="/wiki/Myricetin" title="Myricetin">Myricetin</a></li> <li><a href="/w/index.php?title=Niraxostat&action=edit&redlink=1" class="new" title="Niraxostat (page does not exist)">Niraxostat</a></li> <li><a href="/wiki/Oxipurinol" title="Oxipurinol">Oxipurinol</a></li> <li><a href="/wiki/Phytic_acid" title="Phytic acid">Phytic acid</a></li> <li><i><a href="/wiki/Pistacia_integerrima" title="Pistacia integerrima">Pistacia integerrima</a></i></li> <li><a href="/wiki/Propolis" title="Propolis">Propolis</a></li> <li><a href="/wiki/Quercetin" title="Quercetin">Quercetin</a></li> <li><a href="/wiki/Tisopurine" title="Tisopurine">Tisopurine</a></li> <li><a href="/wiki/Topiroxostat" title="Topiroxostat">Topiroxostat</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;">Others</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aminopterin" title="Aminopterin">Aminopterin</a></li> <li><a href="/wiki/Azathioprine" title="Azathioprine">Azathioprine</a></li> <li><a href="/wiki/Methotrexate" title="Methotrexate">Methotrexate</a></li> <li><a href="/wiki/Mycophenolic_acid" title="Mycophenolic acid">Mycophenolic acid</a></li> <li><a href="/wiki/Pemetrexed" title="Pemetrexed">Pemetrexed</a></li> <li><a href="/wiki/Pralatrexate" title="Pralatrexate">Pralatrexate</a></li> <li><i>Many others</i></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Others</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><b>Precursors:</b> <a href="/wiki/Adenine" title="Adenine">Adenine</a></li> <li><a href="/wiki/Adenosine" title="Adenosine">Adenosine</a></li> <li><a href="/wiki/Adenosine_monophosphate" title="Adenosine monophosphate">AMP</a></li> <li><a href="/wiki/Adenosine_diphosphate" title="Adenosine diphosphate">ADP</a></li> <li><a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a></li> <li><a href="/wiki/Cytosine" title="Cytosine">Cytosine</a></li> <li><a href="/wiki/Cytidine" title="Cytidine">Cytidine</a></li> <li><a href="/wiki/Cytidine_monophosphate" title="Cytidine monophosphate">CMP</a></li> <li><a href="/wiki/Cytidine_diphosphate" title="Cytidine diphosphate">CDP</a></li> <li><a href="/wiki/Cytidine_triphosphate" title="Cytidine triphosphate">CTP</a></li> <li><a href="/wiki/Guanine" title="Guanine">Guanine</a></li> <li><a href="/wiki/Guanosine" title="Guanosine">Guanosine</a></li> <li><a href="/wiki/Guanosine_monophosphate" title="Guanosine monophosphate">GMP</a></li> <li><a href="/wiki/Guanosine_diphosphate" title="Guanosine diphosphate">GDP</a></li> <li><a href="/wiki/Guanosine_triphosphate" title="Guanosine triphosphate">GTP</a></li> <li><a href="/wiki/Hypoxanthine" title="Hypoxanthine">Hypoxanthine</a></li> <li><a href="/wiki/Inosine" title="Inosine">Inosine</a></li> <li><a href="/wiki/Inosine_monophosphate" class="mw-redirect" title="Inosine monophosphate">IMP</a></li> <li><a href="/w/index.php?title=Inosine_diphosphate&action=edit&redlink=1" class="new" title="Inosine diphosphate (page does not exist)">IDP</a></li> <li><a href="/wiki/Inosine_triphosphate" title="Inosine triphosphate">ITP</a></li> <li><a href="/wiki/Ribose" title="Ribose">Ribose</a></li> <li><a href="/wiki/Uracil" title="Uracil">Uracil</a></li> <li><a href="/wiki/Uridine" title="Uridine">Uridine</a></li> <li><a href="/wiki/Uridine_monophosphate" title="Uridine monophosphate">UMP</a></li> <li><a href="/wiki/Uridine_diphosphate" title="Uridine diphosphate">UDP</a></li> <li><a href="/wiki/Uridine_triphosphate" title="Uridine triphosphate">UTP</a></li></ul> <ul><li><b>Others:</b> <a href="/wiki/Chrysophanol" title="Chrysophanol">Chrysophanol</a> (<a href="/wiki/Rhubarb" title="Rhubarb">rhubarb</a>)</li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div><i><b>See also:</b> <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></i></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><style data-mw-deduplicate="TemplateStyles:r1038841319">.mw-parser-output .tooltip-dotted{border-bottom:1px dotted;cursor:help}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"></div><div role="navigation" class="navbox authority-control" aria-labelledby="Authority_control_databases_frameless&#124;text-top&#124;10px&#124;alt=Edit_this_at_Wikidata&#124;link=https&#58;//www.wikidata.org/wiki/Q105522#identifiers&#124;class=noprint&#124;Edit_this_at_Wikidata" style="padding:3px"><table class="nowraplinks hlist mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><div id="Authority_control_databases_frameless&#124;text-top&#124;10px&#124;alt=Edit_this_at_Wikidata&#124;link=https&#58;//www.wikidata.org/wiki/Q105522#identifiers&#124;class=noprint&#124;Edit_this_at_Wikidata" style="font-size:114%;margin:0 4em"><a href="/wiki/Help:Authority_control" title="Help:Authority control">Authority control databases</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q105522#identifiers" 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></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">International</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"><ul><li><span class="uid"><a rel="nofollow" class="external text" href="http://id.worldcat.org/fast/1162912/">FAST</a></span></li></ul></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">National</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"><ul><li><span class="uid"><a rel="nofollow" class="external text" href="https://d-nb.info/gnd/4159149-5">Germany</a></span></li><li><span class="uid"><a rel="nofollow" class="external text" href="https://id.loc.gov/authorities/sh85141398">United States</a></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="Urique"><a rel="nofollow" class="external text" href="https://catalogue.bnf.fr/ark:/12148/cb12282853q">France</a></span></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="Urique"><a rel="nofollow" class="external text" href="https://data.bnf.fr/ark:/12148/cb12282853q">BnF data</a></span></span></li><li><span class="uid"><a rel="nofollow" class="external text" href="https://id.ndl.go.jp/auth/ndlna/00568751">Japan</a></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="kyselina močová"><a rel="nofollow" class="external text" href="https://aleph.nkp.cz/F/?func=find-c&local_base=aut&ccl_term=ica=ph520079&CON_LNG=ENG">Czech 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