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class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Structure</span> </div> </a> <ul id="toc-Structure-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Functions" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Functions"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Functions</span> </div> </a> <button aria-controls="toc-Functions-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 Functions subsection</span> </button> <ul id="toc-Functions-sublist" class="vector-toc-list"> <li id="toc-Signaling_pathways" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Signaling_pathways"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Signaling pathways</span> </div> </a> <ul id="toc-Signaling_pathways-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Metabolism" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Metabolism"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Metabolism</span> </div> </a> <ul id="toc-Metabolism-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Nucleotide_biosynthesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Nucleotide_biosynthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span>Nucleotide biosynthesis</span> </div> </a> <ul id="toc-Nucleotide_biosynthesis-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Modifications" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Modifications"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Modifications</span> </div> </a> <button aria-controls="toc-Modifications-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 Modifications subsection</span> </button> <ul id="toc-Modifications-sublist" class="vector-toc-list"> <li id="toc-Modifications_in_nature" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Modifications_in_nature"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Modifications in nature</span> </div> </a> <ul id="toc-Modifications_in_nature-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Synthetic_modifications" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Synthetic_modifications"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Synthetic modifications</span> </div> </a> <ul id="toc-Synthetic_modifications-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Medical_uses" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Medical_uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Medical uses</span> </div> </a> <ul id="toc-Medical_uses-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> </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">Ribose</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 66 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-66" 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">66 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%B1%D9%8A%D8%A8%D9%88%D8%B2" title="ريبوز – Arabic" lang="ar" hreflang="ar" data-title="ريبوز" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Riboza" title="Riboza – Azerbaijani" lang="az" hreflang="az" data-title="Riboza" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%B1%DB%8C%D8%A8%D9%88%D8%B2" title="ریبوز – South Azerbaijani" lang="azb" hreflang="azb" data-title="ریبوز" 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%B0%E0%A6%BE%E0%A6%87%E0%A6%AC%E0%A7%8B%E0%A6%9C" title="রাইবোজ – Bangla" lang="bn" hreflang="bn" data-title="রাইবোজ" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-zh-min-nan mw-list-item"><a href="https://zh-min-nan.wikipedia.org/wiki/Hu%CC%8Dt-thn%CC%82g" title="Hu̍t-thn̂g – Minnan" lang="nan" hreflang="nan" data-title="Hu̍t-thn̂g" data-language-autonym="閩南語 / Bân-lâm-gú" data-language-local-name="Minnan" class="interlanguage-link-target"><span>閩南語 / Bân-lâm-gú</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%A0%D1%8B%D0%B1%D0%BE%D0%B7%D0%B0" title="Рыбоза – Belarusian" lang="be" hreflang="be" data-title="Рыбоза" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-be-x-old mw-list-item"><a href="https://be-tarask.wikipedia.org/wiki/%D0%A0%D1%8B%D0%B1%D0%BE%D0%B7%D0%B0" title="Рыбоза – Belarusian (Taraškievica orthography)" lang="be-tarask" hreflang="be-tarask" data-title="Рыбоза" data-language-autonym="Беларуская (тарашкевіца)" data-language-local-name="Belarusian (Taraškievica orthography)" class="interlanguage-link-target"><span>Беларуская (тарашкевіца)</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%A0%D0%B8%D0%B1%D0%BE%D0%B7%D0%B0" title="Рибоза – Bulgarian" lang="bg" hreflang="bg" data-title="Рибоза" 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/Riboza" title="Riboza – Bosnian" lang="bs" hreflang="bs" data-title="Riboza" 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/Ribosa" title="Ribosa – Catalan" lang="ca" hreflang="ca" data-title="Ribosa" 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/Rib%C3%B3za" title="Ribóza – Czech" lang="cs" hreflang="cs" data-title="Ribóza" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Ribose" title="Ribose – Danish" lang="da" hreflang="da" data-title="Ribose" 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/Ribose" title="Ribose – German" lang="de" hreflang="de" data-title="Ribose" 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/Riboos" title="Riboos – Estonian" lang="et" hreflang="et" data-title="Riboos" 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%A1%CE%B9%CE%B2%CF%8C%CE%B6%CE%B7" title="Ριβόζη – Greek" lang="el" hreflang="el" data-title="Ριβόζη" 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/Ribosa" title="Ribosa – Spanish" lang="es" hreflang="es" data-title="Ribosa" 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/Ribozo" title="Ribozo – Esperanto" lang="eo" hreflang="eo" data-title="Ribozo" 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/Erribosa" title="Erribosa – Basque" lang="eu" hreflang="eu" data-title="Erribosa" 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%B1%DB%8C%D8%A8%D9%88%D8%B2" title="ریبوز – Persian" lang="fa" hreflang="fa" data-title="ریبوز" 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/Ribose" title="Ribose – French" lang="fr" hreflang="fr" data-title="Ribose" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-fy mw-list-item"><a href="https://fy.wikipedia.org/wiki/Riboaze" title="Riboaze – Western Frisian" lang="fy" hreflang="fy" data-title="Riboaze" data-language-autonym="Frysk" data-language-local-name="Western Frisian" class="interlanguage-link-target"><span>Frysk</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Riob%C3%B3s" title="Riobós – Irish" lang="ga" hreflang="ga" data-title="Riobós" 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/Ribosa" title="Ribosa – Galician" lang="gl" hreflang="gl" data-title="Ribosa" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EB%A6%AC%EB%B3%B4%EC%8A%A4" title="리보스 – Korean" lang="ko" hreflang="ko" data-title="리보스" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D5%8C%D5%AB%D5%A2%D5%B8%D5%A6" title="Ռիբոզ – Armenian" lang="hy" hreflang="hy" data-title="Ռիբոզ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Riboza" title="Riboza – Croatian" lang="hr" hreflang="hr" data-title="Riboza" 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/Ribosa" title="Ribosa – Indonesian" lang="id" hreflang="id" data-title="Ribosa" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Ribosio" title="Ribosio – Italian" lang="it" hreflang="it" data-title="Ribosio" 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%A8%D7%99%D7%91%D7%95%D7%96" title="ריבוז – Hebrew" lang="he" hreflang="he" data-title="ריבוז" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-jv mw-list-item"><a href="https://jv.wikipedia.org/wiki/Ribosa" title="Ribosa – Javanese" lang="jv" hreflang="jv" data-title="Ribosa" data-language-autonym="Jawa" data-language-local-name="Javanese" class="interlanguage-link-target"><span>Jawa</span></a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%A0%E1%83%98%E1%83%91%E1%83%9D%E1%83%96%E1%83%90" title="რიბოზა – Georgian" lang="ka" hreflang="ka" data-title="რიბოზა" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%A0%D0%B8%D0%B1%D0%BE%D0%B7%D0%B0" title="Рибоза – Kazakh" lang="kk" hreflang="kk" data-title="Рибоза" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Riboze" title="Riboze – Latvian" lang="lv" hreflang="lv" data-title="Riboze" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Riboz%C4%97" title="Ribozė – Lithuanian" lang="lt" hreflang="lt" data-title="Ribozė" 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/Rib%C3%B3z" title="Ribóz – Hungarian" lang="hu" hreflang="hu" data-title="Ribóz" 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%A0%D0%B8%D0%B1%D0%BE%D0%B7%D0%B0" title="Рибоза – Macedonian" lang="mk" hreflang="mk" data-title="Рибоза" 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/Ribosa" title="Ribosa – Malay" lang="ms" hreflang="ms" data-title="Ribosa" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Ribose" title="Ribose – Dutch" lang="nl" hreflang="nl" data-title="Ribose" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%AA%E3%83%9C%E3%83%BC%E3%82%B9" title="リボース – Japanese" lang="ja" hreflang="ja" data-title="リボース" 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/Ribose" title="Ribose – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Ribose" 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-nn mw-list-item"><a href="https://nn.wikipedia.org/wiki/Ribose" title="Ribose – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Ribose" data-language-autonym="Norsk nynorsk" data-language-local-name="Norwegian Nynorsk" class="interlanguage-link-target"><span>Norsk nynorsk</span></a></li><li class="interlanguage-link interwiki-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Rib%C3%B2sa" title="Ribòsa – Occitan" lang="oc" hreflang="oc" data-title="Ribòsa" data-language-autonym="Occitan" data-language-local-name="Occitan" class="interlanguage-link-target"><span>Occitan</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Riboza" title="Riboza – Uzbek" lang="uz" hreflang="uz" data-title="Riboza" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Ryboza" title="Ryboza – Polish" lang="pl" hreflang="pl" data-title="Ryboza" 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/Ribose" title="Ribose – Portuguese" lang="pt" hreflang="pt" data-title="Ribose" 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/Riboz%C4%83" title="Riboză – Romanian" lang="ro" hreflang="ro" data-title="Riboză" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-qu mw-list-item"><a href="https://qu.wikipedia.org/wiki/Ripusa" title="Ripusa – Quechua" lang="qu" hreflang="qu" data-title="Ripusa" data-language-autonym="Runa Simi" data-language-local-name="Quechua" class="interlanguage-link-target"><span>Runa Simi</span></a></li><li class="interlanguage-link interwiki-rue mw-list-item"><a href="https://rue.wikipedia.org/wiki/%D0%A0%D0%B8%D0%B1%D0%BE%D0%B7%D0%B0" title="Рибоза – Rusyn" lang="rue" hreflang="rue" data-title="Рибоза" data-language-autonym="Русиньскый" data-language-local-name="Rusyn" class="interlanguage-link-target"><span>Русиньскый</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%A0%D0%B8%D0%B1%D0%BE%D0%B7%D0%B0" title="Рибоза – Russian" lang="ru" hreflang="ru" data-title="Рибоза" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sq mw-list-item"><a href="https://sq.wikipedia.org/wiki/Riboza" title="Riboza – Albanian" lang="sq" hreflang="sq" data-title="Riboza" data-language-autonym="Shqip" data-language-local-name="Albanian" class="interlanguage-link-target"><span>Shqip</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Ribose" title="Ribose – Simple English" lang="en-simple" hreflang="en-simple" data-title="Ribose" 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/Rib%C3%B3za" title="Ribóza – Slovak" lang="sk" hreflang="sk" data-title="Ribóza" 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/Riboza" title="Riboza – Slovenian" lang="sl" hreflang="sl" data-title="Riboza" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-ckb mw-list-item"><a href="https://ckb.wikipedia.org/wiki/%DA%95%D8%A7%DB%8C%D8%A8%DB%86%D8%B2" title="ڕایبۆز – Central Kurdish" lang="ckb" hreflang="ckb" data-title="ڕایبۆز" data-language-autonym="کوردی" data-language-local-name="Central Kurdish" class="interlanguage-link-target"><span>کوردی</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%A0%D0%B8%D0%B1%D0%BE%D0%B7%D0%B0" title="Рибоза – Serbian" lang="sr" hreflang="sr" data-title="Рибоза" 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/Riboza" title="Riboza – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Riboza" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Riboosi" title="Riboosi – Finnish" lang="fi" hreflang="fi" data-title="Riboosi" 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/Ribos" title="Ribos – Swedish" lang="sv" hreflang="sv" data-title="Ribos" 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%87%E0%AE%B0%E0%AF%88%E0%AE%AA%E0%AF%8B%E0%AE%9A%E0%AF%81" title="இரைபோசு – Tamil" lang="ta" hreflang="ta" data-title="இரைபோசு" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-tt mw-list-item"><a href="https://tt.wikipedia.org/wiki/%D0%A0%D0%B8%D0%B1%D0%BE%D0%B7%D0%B0" title="Рибоза – Tatar" lang="tt" hreflang="tt" data-title="Рибоза" data-language-autonym="Татарча / tatarça" data-language-local-name="Tatar" class="interlanguage-link-target"><span>Татарча / tatarça</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B9%84%E0%B8%A3%E0%B9%82%E0%B8%9A%E0%B8%AA" title="ไรโบส – Thai" lang="th" hreflang="th" data-title="ไรโบส" 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/Riboz" title="Riboz – Turkish" lang="tr" hreflang="tr" data-title="Riboz" 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%A0%D0%B8%D0%B1%D0%BE%D0%B7%D0%B0" title="Рибоза – Ukrainian" lang="uk" hreflang="uk" data-title="Рибоза" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Ribose" title="Ribose – Vietnamese" lang="vi" hreflang="vi" data-title="Ribose" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E6%A0%B8%E7%B3%96" title="核糖 – Wu" lang="wuu" hreflang="wuu" data-title="核糖" data-language-autonym="吴语" data-language-local-name="Wu" class="interlanguage-link-target"><span>吴语</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E6%A0%B8%E7%B3%96" title="核糖 – Chinese" lang="zh" hreflang="zh" data-title="核糖" data-language-autonym="中文" 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class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Group of simple sugar and carbohydrate compounds</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><span class="nowrap"> <style data-mw-deduplicate="TemplateStyles:r920966791">.mw-parser-output span.smallcaps{font-variant:small-caps}.mw-parser-output span.smallcaps-smaller{font-size:85%}</style><span class="smallcaps">d</span>-Ribose</span> </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:D-Ribose.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f7/D-Ribose.png/110px-D-Ribose.png" decoding="async" width="110" height="54" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f7/D-Ribose.png/165px-D-Ribose.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f7/D-Ribose.png/220px-D-Ribose.png 2x" data-file-width="1129" data-file-height="559" /></a><figcaption></figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:DRibose_Fischer.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8f/DRibose_Fischer.svg/70px-DRibose_Fischer.svg.png" decoding="async" width="70" height="117" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8f/DRibose_Fischer.svg/105px-DRibose_Fischer.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8f/DRibose_Fischer.svg/140px-DRibose_Fischer.svg.png 2x" data-file-width="72" data-file-height="120" /></a><figcaption></figcaption></figure> </td></tr></tbody></table> </td></tr> <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:Beta-D-Ribofuranose.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e2/Beta-D-Ribofuranose.svg/110px-Beta-D-Ribofuranose.svg.png" decoding="async" width="110" height="125" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e2/Beta-D-Ribofuranose.svg/165px-Beta-D-Ribofuranose.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e2/Beta-D-Ribofuranose.svg/220px-Beta-D-Ribofuranose.svg.png 2x" data-file-width="135" data-file-height="153" /></a><figcaption></figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Beta-D-Ribopyranose.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Beta-D-Ribopyranose.svg/110px-Beta-D-Ribopyranose.svg.png" decoding="async" width="110" height="94" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Beta-D-Ribopyranose.svg/165px-Beta-D-Ribopyranose.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Beta-D-Ribopyranose.svg/220px-Beta-D-Ribopyranose.svg.png 2x" data-file-width="157" data-file-height="134" /></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/Chemical_nomenclature" title="Chemical nomenclature">IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><small>D</small>-Ribose</div> </td></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature#Systematic_name" title="Chemical nomenclature">Systematic IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">(2<i>R</i>,3<i>R</i>,4<i>S</i>,5<i>R</i>)-5-(hydroxymethyl)oxolane-2,3,4-triol</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;"><span class="nowrap"> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-Ribose</span></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=50-69-1">50-69-1</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>aldehydo form D-(−)-Ribose: <span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=C%28%5BC%40H%5D%28%5BC%40H%5D%28%5BC%40H%5D%28C%3DO%29O%29O%29O%29O">Interactive image</a></span></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/ChEMBL1159662">ChEMBL1159662</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/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.4470639.html">4470639</a></span> aldehydo form D-(−)-Ribose<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/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/DB01936">DB01936</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/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>200-059-4</li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/5779">5779</a></span></li><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/5311110">5311110</a></span> aldehydo form D-(−)-Ribose</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/681HV46001">681HV46001</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 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%;">aldehydo form D-(−)-Ribose: InChI=1/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h1,3-5,7-10H,2H2/t3-,4+,5-/m0/s1</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: PYMYPHUHKUWMLA-LMVFSUKVBD</div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Aldehydo form D-(−)-Ribose: InChI=1S/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h1,3-5,7-10H,2H2/t3-,4+,5-/m0/s1</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: PYMYPHUHKUWMLA-LMVFSUKVSA-N</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%;">aldehydo form D-(−)-Ribose: C([C@H]([C@H]([C@H](C=O)O)O)O)O</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties<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><sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td>C<sub>5</sub>H<sub>10</sub>O<sub>5</sub>  </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td>150.13    </td></tr> <tr> <td>Appearance </td> <td>White solid </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>95 °C (203 °F; 368 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>100<span class="nowrap"> </span>g/L (25 °C, 77 °F) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Specific_rotation" title="Specific rotation">Chiral rotation</a> ([α]<sub>D</sub>)</div> </td> <td>−21.5° (H<sub>2</sub>O) </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Related compounds </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related <a href="/wiki/Pentose" title="Pentose">aldopentoses</a></div> </td> <td><a href="/wiki/Arabinose" title="Arabinose">Arabinose</a><br /><a href="/wiki/Xylose" title="Xylose">Xylose</a><br /><a href="/wiki/Lyxose" title="Lyxose">Lyxose</a> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related compounds</div> </td> <td><a href="/wiki/Deoxyribose" title="Deoxyribose">Deoxyribose</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="☒" 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=412792499&page2=Ribose">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> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Fischer_Projection_of_L-Ribose.jpg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/d/db/Fischer_Projection_of_L-Ribose.jpg" decoding="async" width="121" height="230" class="mw-file-element" data-file-width="121" data-file-height="230" /></a><figcaption><span class="nowrap"> <small>L</small>-Ribose</span> Fischer Projection</figcaption></figure> <p><b>Ribose</b> is a <a href="/wiki/Simple_sugar" class="mw-redirect" title="Simple sugar">simple sugar</a> and <a href="/wiki/Carbohydrate" title="Carbohydrate">carbohydrate</a> with <a href="/wiki/Molecular_formula" class="mw-redirect" title="Molecular formula">molecular formula</a> C<sub>5</sub>H<sub>10</sub>O<sub>5</sub> and the linear-form composition H−(C=O)−(CHOH)<sub>4</sub>−H. The naturally occurring form, <span class="nowrap"> <b><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-ribose</b></span>, is a component of the <a href="/wiki/Ribonucleotide" title="Ribonucleotide">ribonucleotides</a> from which <a href="/wiki/RNA" title="RNA">RNA</a> is built, and so this compound is necessary for <a href="/wiki/Genetic_code" title="Genetic code">coding</a>, <a href="/wiki/Translation_(biology)" title="Translation (biology)">decoding</a>, <a href="/wiki/Regulatory_RNA" class="mw-redirect" title="Regulatory RNA">regulation</a> and <a href="/wiki/RNA_splicing" title="RNA splicing">expression</a> of <a href="/wiki/Gene" title="Gene">genes</a>. It has a <a href="/wiki/Structural_analog" title="Structural analog">structural analog</a>, <a href="/wiki/Deoxyribose" title="Deoxyribose">deoxyribose</a>, which is a similarly essential component of <a href="/wiki/DNA" title="DNA">DNA</a>. <span class="nowrap"> <b><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">l</span>-ribose</b></span> is an unnatural sugar that was first prepared by <a href="/wiki/Emil_Fischer" title="Emil Fischer">Emil Fischer</a> and <a href="/wiki/Oscar_Piloty" class="mw-redirect" title="Oscar Piloty">Oscar Piloty</a> in 1891.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> It was not until 1909 that <a href="/wiki/Phoebus_Levene" title="Phoebus Levene">Phoebus Levene</a> and <a href="/wiki/Walter_Abraham_Jacobs" title="Walter Abraham Jacobs">Walter Jacobs</a> recognised that <span class="nowrap"> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-ribose</span> was a <a href="/wiki/Natural_product" title="Natural product">natural product</a>, the <a href="/wiki/Enantiomer" title="Enantiomer">enantiomer</a> of Fischer and Piloty's product, and an essential component of <a href="/wiki/Nucleic_acid" title="Nucleic acid">nucleic acids</a>.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-RiboseReview_6-0" class="reference"><a href="#cite_note-RiboseReview-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Fischer chose the name "ribose" as it is a partial rearrangement of the name of another sugar, <a href="/wiki/Arabinose" title="Arabinose">arabinose</a>, of which ribose is an <a href="/wiki/Epimer" title="Epimer">epimer</a> at the 2' carbon; both names also relate to <a href="/wiki/Gum_arabic" title="Gum arabic">gum arabic</a>, from which arabinose was first isolated and from which they prepared <span class="nowrap"> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">l</span>-ribose</span>.<sup id="cite_ref-RiboseReview_6-1" class="reference"><a href="#cite_note-RiboseReview-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <style data-mw-deduplicate="TemplateStyles:r1237032888/mw-parser-output/.tmulti">.mw-parser-output .tmulti .multiimageinner{display:flex;flex-direction:column}.mw-parser-output .tmulti 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.trow>.thumbcaption{text-align:center}}@media screen{html.skin-theme-clientpref-night .mw-parser-output .tmulti .multiimageinner img{background-color:white}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .tmulti .multiimageinner img{background-color:white}}</style><div class="thumb tmulti tnone center"><div class="thumbinner multiimageinner" style="width:493px;max-width:493px"><div class="trow"><div class="tsingle" style="width:123px;max-width:123px"><div class="thumbimage" style="height:137px;overflow:hidden"><span typeof="mw:File"><a href="/wiki/File:Beta-D-Ribofuranose.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e2/Beta-D-Ribofuranose.svg/121px-Beta-D-Ribofuranose.svg.png" decoding="async" width="121" height="137" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e2/Beta-D-Ribofuranose.svg/182px-Beta-D-Ribofuranose.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e2/Beta-D-Ribofuranose.svg/242px-Beta-D-Ribofuranose.svg.png 2x" data-file-width="135" data-file-height="153" /></a></span></div><div class="thumbcaption"><span class="nowrap"> β-<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-ribofuranose</span></div></div><div class="tsingle" style="width:168px;max-width:168px"><div class="thumbimage" style="height:137px;overflow:hidden"><span typeof="mw:File"><a href="/wiki/File:Alpha-D-Ribopyranose.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a3/Alpha-D-Ribopyranose.svg/166px-Alpha-D-Ribopyranose.svg.png" decoding="async" width="166" height="137" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a3/Alpha-D-Ribopyranose.svg/249px-Alpha-D-Ribopyranose.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a3/Alpha-D-Ribopyranose.svg/332px-Alpha-D-Ribopyranose.svg.png 2x" data-file-width="157" data-file-height="130" /></a></span></div><div class="thumbcaption"><span class="nowrap"> α-<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-ribopyranose</span></div></div><div class="tsingle" style="width:97px;max-width:97px"><div class="thumbimage" style="height:137px;overflow:hidden"><span typeof="mw:File"><a href="/wiki/File:D-%D1%80%D0%B8%D0%B1%D0%BE%D0%B7%D0%B0.png" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/75/D-%D1%80%D0%B8%D0%B1%D0%BE%D0%B7%D0%B0.png/95px-D-%D1%80%D0%B8%D0%B1%D0%BE%D0%B7%D0%B0.png" decoding="async" width="95" height="138" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/75/D-%D1%80%D0%B8%D0%B1%D0%BE%D0%B7%D0%B0.png/143px-D-%D1%80%D0%B8%D0%B1%D0%BE%D0%B7%D0%B0.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/75/D-%D1%80%D0%B8%D0%B1%D0%BE%D0%B7%D0%B0.png/190px-D-%D1%80%D0%B8%D0%B1%D0%BE%D0%B7%D0%B0.png 2x" data-file-width="897" data-file-height="1300" /></a></span></div><div class="thumbcaption"><span class="nowrap"> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-ribose</span></div></div><div class="tsingle" style="width:97px;max-width:97px"><div class="thumbimage" style="height:137px;overflow:hidden"><span typeof="mw:File"><a href="/wiki/File:L-%D1%80%D0%B8%D0%B1%D0%BE%D0%B7%D0%B0.png" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5d/L-%D1%80%D0%B8%D0%B1%D0%BE%D0%B7%D0%B0.png/95px-L-%D1%80%D0%B8%D0%B1%D0%BE%D0%B7%D0%B0.png" decoding="async" width="95" height="138" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5d/L-%D1%80%D0%B8%D0%B1%D0%BE%D0%B7%D0%B0.png/143px-L-%D1%80%D0%B8%D0%B1%D0%BE%D0%B7%D0%B0.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5d/L-%D1%80%D0%B8%D0%B1%D0%BE%D0%B7%D0%B0.png/190px-L-%D1%80%D0%B8%D0%B1%D0%BE%D0%B7%D0%B0.png 2x" data-file-width="897" data-file-height="1300" /></a></span></div><div class="thumbcaption"><span class="nowrap"> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">l</span>-ribose</span></div></div></div><div class="trow" style="display:flex"><div class="thumbcaption">Left: <a href="/wiki/Haworth_projection" title="Haworth projection">Haworth projections</a> of one of each of the furanose and pyranose forms of <span class="nowrap"> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-ribose</span><br />Right: <a href="/wiki/Fischer_projection" title="Fischer projection">Fischer projection</a> of the <a href="/wiki/Open_chain" class="mw-redirect" title="Open chain">open chain</a> forms of <span class="nowrap"> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>- and <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">l</span>- ribose</span></div></div></div></div> <p>Like most sugars, ribose exists as a mixture of <a href="/wiki/Cyclic_compound" title="Cyclic compound">cyclic forms</a> in <a href="/wiki/Chemical_equilibrium" title="Chemical equilibrium">equilibrium</a> with its linear form, and these readily interconvert especially in <a href="/wiki/Aqueous_solution" title="Aqueous solution">aqueous solution</a>.<sup id="cite_ref-Dewick_8-0" class="reference"><a href="#cite_note-Dewick-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> The name "ribose" is used in biochemistry and biology to refer to all of these forms, though more specific names for each are used when required. In its linear form, ribose can be recognised as the <a href="/wiki/Pentose" title="Pentose">pentose</a> sugar with all of its <a href="/wiki/Hydroxyl" class="mw-redirect" title="Hydroxyl">hydroxyl</a> <a href="/wiki/Functional_group" title="Functional group">functional groups</a> on the same side in its <a href="/wiki/Fischer_projection" title="Fischer projection">Fischer projection</a>. <span class="nowrap"> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-Ribose</span> has these hydroxyl groups on the right hand side and is associated with the <a href="/wiki/IUPAC_nomenclature_of_organic_chemistry" title="IUPAC nomenclature of organic chemistry">systematic name</a> (2<i>R</i>,3<i>R</i>,4<i>R</i>)-2,3,4,5-tetrahydroxypentanal,<sup id="cite_ref-ChemInt_9-0" class="reference"><a href="#cite_note-ChemInt-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> whilst <span class="nowrap"> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">l</span>-ribose</span> has its hydroxyl groups appear on the left hand side in a Fischer projection. Cyclisation of ribose occurs via <a href="/wiki/Hemiacetal" title="Hemiacetal">hemiacetal</a> formation due to attack on the <a href="/wiki/Aldehyde" title="Aldehyde">aldehyde</a> by the C4' hydroxyl group to produce a <a href="/wiki/Furanose" title="Furanose">furanose</a> form or by the C5' hydroxyl group to produce a <a href="/wiki/Pyranose" title="Pyranose">pyranose</a> form. In each case, there are two possible geometric outcomes, named as α- and β- and known as <a href="/wiki/Anomer" title="Anomer">anomers</a>, depending on the <a href="/wiki/Stereochemistry" title="Stereochemistry">stereochemistry</a> at the hemiacetal carbon atom (the "anomeric carbon"). At room temperature, about 76% of <span class="nowrap"> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-ribose</span> is present in pyranose forms<sup id="cite_ref-Dewick_8-1" class="reference"><a href="#cite_note-Dewick-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 228">: 228 </span></sup> (α:β = 1:2)<sup id="cite_ref-Bhutani_10-0" class="reference"><a href="#cite_note-Bhutani-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> and 24% in the furanose forms<sup id="cite_ref-Dewick_8-2" class="reference"><a href="#cite_note-Dewick-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 228">: 228 </span></sup> (α:β = 1:3),<sup id="cite_ref-Bhutani_10-1" class="reference"><a href="#cite_note-Bhutani-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> with only about 0.1% of the linear form present.<sup id="cite_ref-DrewEtAl_11-0" class="reference"><a href="#cite_note-DrewEtAl-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> </p><p>The <a href="/wiki/Ribonucleoside" title="Ribonucleoside">ribonucleosides</a> <a href="/wiki/Adenosine" title="Adenosine">adenosine</a>, <a href="/wiki/Cytidine" title="Cytidine">cytidine</a>, <a href="/wiki/Guanosine" title="Guanosine">guanosine</a>, and <a href="/wiki/Uridine" title="Uridine">uridine</a> are all <a href="/wiki/Derivative_(chemistry)" title="Derivative (chemistry)">derivatives</a> of β-<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-ribofuranose. <a href="/wiki/Metabolism" title="Metabolism">Metabolically important</a> species that include <a href="/wiki/Phosphorylated" class="mw-redirect" title="Phosphorylated">phosphorylated</a> ribose include <a href="/wiki/Adenosine_diphosphate" title="Adenosine diphosphate">ADP</a>, <a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a>, <a href="/wiki/Coenzyme_A" title="Coenzyme A">coenzyme A</a>,<sup id="cite_ref-Dewick_8-3" class="reference"><a href="#cite_note-Dewick-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 228–229">: 228–229 </span></sup> and <a href="/wiki/Nicotinamide_adenine_dinucleotide" title="Nicotinamide adenine dinucleotide">NADH</a>. <a href="/wiki/Cyclic_adenosine_monophosphate" title="Cyclic adenosine monophosphate">cAMP</a> and <a href="/wiki/Cyclic_guanosine_monophosphate" title="Cyclic guanosine monophosphate">cGMP</a> serve as secondary messengers in some signaling pathways and are also ribose derivatives. The ribose <a href="/wiki/Moiety_(chemistry)" title="Moiety (chemistry)">moiety</a> appears in some pharmaceutical agents, including the antibiotics <a href="/wiki/Neomycin" title="Neomycin">neomycin</a> and <a href="/wiki/Paromomycin" title="Paromomycin">paromomycin</a>.<sup id="cite_ref-Bhutani_10-2" class="reference"><a href="#cite_note-Bhutani-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Synthesis_and_sources">Synthesis and sources</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ribose&action=edit&section=1" title="Edit section: Synthesis and sources"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ribose as its 5-phosphate ester is typically produced from glucose by the <a href="/wiki/Pentose_phosphate_pathway" title="Pentose phosphate pathway">pentose phosphate pathway</a>. In at least some archaea, alternative pathways have been identified.<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><p>Ribose can be synthesized chemically, but commercial production relies on fermentation of glucose. Using genetically modified strains of <i><a href="/wiki/B._subtilis" class="mw-redirect" title="B. subtilis">B. subtilis</a></i>, 90 g/liter of ribose can be produced from 200 g of glucose. The conversion entails the intermediacy of gluconate and ribulose.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p><p>Ribose has been detected in <a href="/wiki/Meteorite" title="Meteorite">meteorites</a>.<sup id="cite_ref-NASA-20191118_15-0" class="reference"><a href="#cite_note-NASA-20191118-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-PNAS-20191118_16-0" class="reference"><a href="#cite_note-PNAS-20191118-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Structure">Structure</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ribose&action=edit&section=2" title="Edit section: Structure"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ribose is an <a href="/wiki/Aldopentose" class="mw-redirect" title="Aldopentose">aldopentose</a> (a monosaccharide containing five <a href="/wiki/Carbon" title="Carbon">carbon</a> atoms that, in its <a href="/wiki/Open_chain" class="mw-redirect" title="Open chain">open chain</a> form, has an <a href="/wiki/Aldehyde" title="Aldehyde">aldehyde</a> <a href="/wiki/Functional_group" title="Functional group">functional group</a> at one end). In the conventional numbering scheme for monosaccharides, the carbon atoms are numbered from C1' (in the aldehyde group) to C5'. The <a href="/wiki/Deoxyribose" title="Deoxyribose">deoxyribose</a> derivative found in DNA differs from ribose by having a <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> atom in place of the <a href="/wiki/Hydroxyl" class="mw-redirect" title="Hydroxyl">hydroxyl</a> group at C2'. This hydroxyl group performs a function in <a href="/wiki/RNA_splicing" title="RNA splicing">RNA splicing</a>. </p><p> The "<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-" in the name <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-ribose refers to the <a href="/wiki/Stereochemistry" title="Stereochemistry">stereochemistry</a> of the <a href="/wiki/Chirality_(chemistry)" title="Chirality (chemistry)">chiral</a> carbon atom farthest away from the aldehyde group (C4'). In <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-ribose, as in all <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-sugars, this carbon atom has the same configuration as in <a href="/wiki/D-glyceraldehyde" class="mw-redirect" title="D-glyceraldehyde"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-glyceraldehyde</a>.</p><ul class="gallery mw-gallery-traditional"> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Alpha-D-Ribopyranose_numbered.png" class="mw-file-description" title="α-d-Ribopyranose"><img alt="α-d-Ribopyranose" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e2/Alpha-D-Ribopyranose_numbered.png/120px-Alpha-D-Ribopyranose_numbered.png" decoding="async" width="120" height="107" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e2/Alpha-D-Ribopyranose_numbered.png/180px-Alpha-D-Ribopyranose_numbered.png 1.5x, //upload.wikimedia.org/wikipedia/commons/e/e2/Alpha-D-Ribopyranose_numbered.png 2x" data-file-width="207" data-file-height="185" /></a></span></div> <div class="gallerytext">α-<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-Ribopyranose</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Beta-D-Ribopyranose_numbered.png" class="mw-file-description" title="β-d-Ribopyranose"><img alt="β-d-Ribopyranose" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c6/Beta-D-Ribopyranose_numbered.png/120px-Beta-D-Ribopyranose_numbered.png" decoding="async" width="120" height="111" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c6/Beta-D-Ribopyranose_numbered.png/180px-Beta-D-Ribopyranose_numbered.png 1.5x, //upload.wikimedia.org/wikipedia/commons/c/c6/Beta-D-Ribopyranose_numbered.png 2x" data-file-width="197" data-file-height="182" /></a></span></div> <div class="gallerytext">β-<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-Ribopyranose</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Alpha-D-Ribofuranose_numbered.png" class="mw-file-description" title="α-d-Ribofuranose"><img alt="α-d-Ribofuranose" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0c/Alpha-D-Ribofuranose_numbered.png/109px-Alpha-D-Ribofuranose_numbered.png" decoding="async" width="109" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0c/Alpha-D-Ribofuranose_numbered.png/164px-Alpha-D-Ribofuranose_numbered.png 1.5x, //upload.wikimedia.org/wikipedia/commons/0/0c/Alpha-D-Ribofuranose_numbered.png 2x" data-file-width="198" data-file-height="217" /></a></span></div> <div class="gallerytext">α-<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-Ribofuranose</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Beta-D-Ribofuranose_Numbered.png" class="mw-file-description" title="β-d-Ribofuranose"><img alt="β-d-Ribofuranose" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Beta-D-Ribofuranose_Numbered.png/117px-Beta-D-Ribofuranose_Numbered.png" decoding="async" width="117" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/e/e6/Beta-D-Ribofuranose_Numbered.png 1.5x" data-file-width="170" data-file-height="175" /></a></span></div> <div class="gallerytext">β-<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-Ribofuranose</div> </li> </ul><p>Relative abundance of forms of ribose in solution: β-<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-ribopyranose (59%), α-<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-ribopyranose (20%), β-<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-ribofuranose (13%), α-<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-ribofuranose (7%) and open chain (0.1%).<sup id="cite_ref-DrewEtAl_11-1" class="reference"><a href="#cite_note-DrewEtAl-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p><p>For ribose residues in <a href="/wiki/Nucleoside" title="Nucleoside">nucleosides</a> and <a href="/wiki/Nucleotide" title="Nucleotide">nucleotide</a>, the torsion angles for the rotation encompassing the bonds influence the configuration of the respective nucleoside and nucleotide. The <a href="/wiki/Secondary_structure" class="mw-redirect" title="Secondary structure">secondary structure</a> of a nucleic acid is determined by the rotation of its 7 <a href="/wiki/Torsion_angle" class="mw-redirect" title="Torsion angle">torsion angles</a>.<sup id="cite_ref-:1_17-0" class="reference"><a href="#cite_note-:1-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> Having a large amount of torsion angles allows for greater flexibility. </p><p> In closed ring riboses, the observed flexibility mentioned above is not observed because the ring cycle imposes a limit on the number of torsion angles possible in the structure.<sup id="cite_ref-:1_17-1" class="reference"><a href="#cite_note-:1-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> Conformers of closed form riboses differ in regards to how the lone <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> in the molecule is positioned respective to the <a href="/wiki/Nitrogenous_base" class="mw-redirect" title="Nitrogenous base">nitrogenous base</a> (also known as a <a href="/wiki/Nucleobase" class="mw-redirect" title="Nucleobase">nucleobase</a> or just a base) attached to the ribose. If a carbon is facing towards the base, then the ribose is labeled as endo. If a carbon is facing away from the base, then the ribose is labeled as exo. If there is an oxygen molecule attached to the 2' carbon of a closed cycle ribose, then the exo confirmation is more stable because it decreases the interactions of the oxygen with the base.<sup id="cite_ref-:1_17-2" class="reference"><a href="#cite_note-:1-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> The difference itself is quite small, but when looking at an entire chain of RNA the slight difference amounts to a sizable impact.</p><ul class="gallery mw-gallery-traditional"> <li class="gallerycaption">Some pucker configurations of ribose</li> <li class="gallerybox" style="width: 235px"> <div class="thumb" style="width: 230px; height: 230px;"><span typeof="mw:File"><a href="/wiki/File:2%27_endo.jpg" class="mw-file-description" title="2' endo"><img alt="2' endo" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9d/2%27_endo.jpg/200px-2%27_endo.jpg" decoding="async" width="200" height="103" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/9/9d/2%27_endo.jpg 1.5x" data-file-width="242" data-file-height="125" /></a></span></div> <div class="gallerytext">2' endo </div> </li> <li class="gallerybox" style="width: 235px"> <div class="thumb" style="width: 230px; height: 230px;"><span typeof="mw:File"><a href="/wiki/File:2%27_endo_3%27_exo.jpg" class="mw-file-description" title="2' endo 3' exo"><img alt="2' endo 3' exo" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/30/2%27_endo_3%27_exo.jpg/200px-2%27_endo_3%27_exo.jpg" decoding="async" width="200" height="126" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/3/30/2%27_endo_3%27_exo.jpg 1.5x" data-file-width="240" data-file-height="151" /></a></span></div> <div class="gallerytext">2' endo 3' exo</div> </li> <li class="gallerybox" style="width: 235px"> <div class="thumb" style="width: 230px; height: 230px;"><span typeof="mw:File"><a href="/wiki/File:3%27_endo_2%27_exo.jpg" class="mw-file-description" title="3' endo 2' exo"><img alt="3' endo 2' exo" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f5/3%27_endo_2%27_exo.jpg/200px-3%27_endo_2%27_exo.jpg" decoding="async" width="200" height="122" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/f/f5/3%27_endo_2%27_exo.jpg 1.5x" data-file-width="245" data-file-height="150" /></a></span></div> <div class="gallerytext">3' endo 2' exo</div> </li> <li class="gallerybox" style="width: 235px"> <div class="thumb" style="width: 230px; height: 230px;"><span typeof="mw:File"><a href="/wiki/File:3%27_endo.jpg" class="mw-file-description" title="3' endo"><img alt="3' endo" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/92/3%27_endo.jpg/200px-3%27_endo.jpg" decoding="async" width="200" height="99" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/9/92/3%27_endo.jpg 1.5x" data-file-width="244" data-file-height="121" /></a></span></div> <div class="gallerytext">3' endo</div> </li> </ul><p>A ribose molecule is typically represented as a planar molecule on paper. Despite this, it is typically non-planar in nature. Even between hydrogen atoms, the many constituents on a ribose molecule cause <a href="/wiki/Steric_hindrance" class="mw-redirect" title="Steric hindrance">steric hindrance</a> and strain between them. To relieve this crowding and <a href="/wiki/Ring_strain" title="Ring strain">ring strain</a>, the ring puckers, i.e. becomes non-planar.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> This puckering is achieved by displacing an atom from the plane, relieving the strain and yielding a more stable conformation.<sup id="cite_ref-:1_17-3" class="reference"><a href="#cite_note-:1-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> Puckering, otherwise known as the sugar ring conformation (specifically ribose sugar), can be described by the amplitude of pucker as well as the <a href="/wiki/Pseudorotation" title="Pseudorotation">pseudorotation</a> angle. The pseudo-rotation angle can be described as either "north (N)" or "south (S)" range. While both ranges are found in double helices, the north range is commonly associated with RNA and the <a href="/wiki/A-DNA" title="A-DNA">A form of DNA</a>. In contrast, the south range is associated with <a href="/wiki/B_form_DNA" class="mw-redirect" title="B form DNA">B form DNA</a>. <a href="/wiki/Z-DNA" title="Z-DNA">Z-DNA</a> contains sugars in both the north and south ranges.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> When only a single atom is displaced, it is referred to as an "envelope" pucker. When two atoms are displaced, it is referred to as a "twist" pucker, in reference to the zigzag orientation.<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> In an "endo" pucker, the major displacement of atoms is on the β-face, the same side as the C4'-C5' bond and the base. In an "exo" pucker, the major displacement of atoms is on the α-face, on the opposite side of the ring. The major forms of ribose are the 3'-endo pucker (commonly adopted by RNA and A-form DNA) and 2'-endo pucker (commonly adopted by B-form DNA).<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> These ring puckers are developed from changes in ring torsion angles; there are infinite combinations of angles so therefore, there is an infinite number of transposable pucker conformations, each separated by disparate activation energies. </p><div class="mw-heading mw-heading2"><h2 id="Functions">Functions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ribose&action=edit&section=3" title="Edit section: Functions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>ATP is derived from ribose; it contains one ribose, three <a href="/wiki/Phosphate" title="Phosphate">phosphate</a> groups, and an <a href="/wiki/Adenine" title="Adenine">adenine</a> base. ATP is created during <a href="/wiki/Cellular_respiration" title="Cellular respiration">cellular respiration</a> from <a href="/wiki/Adenosine_diphosphate" title="Adenosine diphosphate">adenosine diphosphate</a> (ATP with one less phosphate group). </p> <div class="mw-heading mw-heading3"><h3 id="Signaling_pathways">Signaling pathways</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ribose&action=edit&section=4" title="Edit section: Signaling pathways"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div><p> Ribose is a building block in secondary signaling molecules such as <a href="/wiki/Cyclic_adenosine_monophosphate" title="Cyclic adenosine monophosphate">cyclic adenosine monophosphate</a> (cAMP) which is derived from ATP. One specific case in which cAMP is used is in <a href="/wiki/CAMP-dependent_pathway" title="CAMP-dependent pathway">cAMP-dependent signaling pathways</a>. In cAMP signaling pathways, either a stimulative or inhibitory hormone receptor is activated by a <a href="/wiki/Signal_molecule" class="mw-redirect" title="Signal molecule">signal molecule</a>. These receptors are linked to a stimulative or inhibitory regulative <a href="/wiki/G_protein-coupled_receptor" title="G protein-coupled receptor">G-protein</a>. When a stimulative G-protein is activated, <a href="/wiki/Adenylyl_cyclase" title="Adenylyl cyclase">adenylyl cyclase</a> <a href="/wiki/Catalysis" title="Catalysis">catalyzes</a> ATP into cAMP by using Mg<sup>2+</sup> or Mn<sup>2+</sup>. cAMP, a secondary messenger, then goes on to activate <a href="/wiki/Protein_kinase_A" title="Protein kinase A">protein kinase A</a>, which is an <a href="/wiki/Enzyme" title="Enzyme">enzyme</a> that regulates cell <a href="/wiki/Metabolism" title="Metabolism">metabolism</a>. Protein kinase A regulates metabolic enzymes by <a href="/wiki/Phosphorylation" title="Phosphorylation">phosphorylation</a> which causes a change in the cell depending on the original signal molecule. The opposite occurs when an inhibitory G-protein is activated; the G-protein inhibits adenylyl cyclase and ATP is not converted to cAMP. </p><figure typeof="mw:File/Thumb"><a href="/wiki/File:The_difference_between_ribose_and_deoxyribose.png" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fb/The_difference_between_ribose_and_deoxyribose.png/213px-The_difference_between_ribose_and_deoxyribose.png" decoding="async" width="213" height="151" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fb/The_difference_between_ribose_and_deoxyribose.png/320px-The_difference_between_ribose_and_deoxyribose.png 1.5x, //upload.wikimedia.org/wikipedia/commons/f/fb/The_difference_between_ribose_and_deoxyribose.png 2x" data-file-width="321" data-file-height="228" /></a><figcaption>The difference between ribose and deoxyribose is the presence of a 2'OH </figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Metabolism">Metabolism</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ribose&action=edit&section=5" title="Edit section: Metabolism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ribose is referred to as the "molecular currency" because of its involvement in intracellular energy transfers.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (November 2019)">citation needed</span></a></i>]</sup> For example, <a href="/wiki/Nicotinamide_adenine_dinucleotide" title="Nicotinamide adenine dinucleotide">nicotinamide adenine dinucleotide</a> (NAD), <a href="/wiki/Flavin_adenine_dinucleotide" title="Flavin adenine dinucleotide">flavin adenine dinucleotide</a> (FAD), and <a href="/wiki/Nicotinamide_adenine_dinucleotide_phosphate" title="Nicotinamide adenine dinucleotide phosphate">nicotinamide adenine dinucleotide phosphate</a> (NADP) all contain the <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-ribofuranose <a href="/wiki/Moiety_(chemistry)" title="Moiety (chemistry)">moiety</a>. They can each be <a href="/wiki/Derivative_(chemistry)" title="Derivative (chemistry)">derived from</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-ribose after it is converted to <a href="/wiki/Ribose_5-phosphate" title="Ribose 5-phosphate"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-ribose 5-phosphate</a> by the enzyme <a href="/wiki/Ribokinase" title="Ribokinase">ribokinase</a>.<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup><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> NAD, FAD, and NADP act as electron acceptors in biochemical <a href="/wiki/Redox" title="Redox">redox</a> reactions in major metabolic pathways including <a href="/wiki/Glycolysis" title="Glycolysis">glycolysis</a>, the <a href="/wiki/Citric_acid_cycle" title="Citric acid cycle">citric acid cycle</a>, <a href="/wiki/Fermentation" title="Fermentation">fermentation</a>, and the <a href="/wiki/Electron_transport_chain" title="Electron transport chain">electron transport chain</a>. </p> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Pentose_Phosphate_Pathway.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/61/Pentose_Phosphate_Pathway.png/407px-Pentose_Phosphate_Pathway.png" decoding="async" width="407" height="698" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/6/61/Pentose_Phosphate_Pathway.png 1.5x" data-file-width="485" data-file-height="831" /></a><figcaption>Pentose Phosphate Pathway: begins with <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-glucose and includes <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-ribose 5-phosphate as an intermediate</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Nucleotide_biosynthesis">Nucleotide biosynthesis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ribose&action=edit&section=6" title="Edit section: Nucleotide biosynthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Nucleotides are synthesized through salvage or <a href="/wiki/De_novo_synthesis" title="De novo synthesis">de novo synthesis</a>.<sup id="cite_ref-:2_24-0" class="reference"><a href="#cite_note-:2-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Nucleotide_salvage" title="Nucleotide salvage">Nucleotide salvage</a> uses pieces of previously made nucleotides and re-synthesizes them for future use. In de novo, amino acids, carbon dioxide, folate derivatives, and <a href="/wiki/Phosphoribosyl_pyrophosphate" title="Phosphoribosyl pyrophosphate">phosphoribosyl pyrophosphate</a> (PRPP) are used to synthesize nucleotides.<sup id="cite_ref-:2_24-1" class="reference"><a href="#cite_note-:2-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> Both de novo and salvage require PRPP which is synthesized from ATP and ribose 5-phosphate by an enzyme called <a href="/wiki/PRPP_synthetase" class="mw-redirect" title="PRPP synthetase">PRPP synthetase</a>.<sup id="cite_ref-:2_24-2" class="reference"><a href="#cite_note-:2-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Modifications">Modifications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ribose&action=edit&section=7" title="Edit section: Modifications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Modifications_in_nature">Modifications in nature</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ribose&action=edit&section=8" title="Edit section: Modifications in nature"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Ribokinase" title="Ribokinase">Ribokinase</a> catalyzes the conversion of <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-ribose to <a href="/wiki/Ribose_5-phosphate" title="Ribose 5-phosphate"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-ribose 5-phosphate</a>. Once converted, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-ribose-5-phosphate is available for the manufacturing of the <a href="/wiki/Amino_acids" class="mw-redirect" title="Amino acids">amino acids</a> <a href="/wiki/Tryptophan" title="Tryptophan">tryptophan</a> and <a href="/wiki/Histidine" title="Histidine">histidine</a>, or for use in the <a href="/wiki/Pentose_phosphate_pathway" title="Pentose phosphate pathway">pentose phosphate pathway</a>. The absorption of <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-ribose is 88–100% in the small intestines (up to 200 mg/kg·h).<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p><p>One important modification occurs at the C2' position of the ribose molecule. By adding an <a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">O-alkyl</a> group, the nuclear resistance of the RNA is increased because of additional stabilizing forces. These forces are stabilizing because of the increase of <a href="/wiki/Hydrogen_bonding" class="mw-redirect" title="Hydrogen bonding">intramolecular hydrogen bonding</a> and an increase in the <a href="/wiki/Glycosidic_bond" title="Glycosidic bond">glycosidic bond</a> stability.<sup id="cite_ref-:3_26-0" class="reference"><a href="#cite_note-:3-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> The resulting increase of resistance leads to increases in the <a href="/wiki/Half-life" title="Half-life">half-life</a> of <a href="/wiki/Small_interfering_RNA" title="Small interfering RNA">siRNA</a> and the potential therapeutic potential in cells and animals.<sup id="cite_ref-:0_27-0" class="reference"><a href="#cite_note-:0-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Methylation" title="Methylation">methylation</a> of ribose at particular sites is correlated with a decrease in immune stimulation.<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> </p> <div class="mw-heading mw-heading3"><h3 id="Synthetic_modifications">Synthetic modifications</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ribose&action=edit&section=9" title="Edit section: Synthetic modifications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Along with phosphorylation, ribofuranose molecules can exchange their oxygen with <a href="/wiki/Selenium" title="Selenium">selenium</a> and <a href="/wiki/Sulfur" title="Sulfur">sulfur</a> to produce similar sugars that only vary at the 4' position. These derivatives are more <a href="/wiki/Lipophilicity" title="Lipophilicity">lipophilic</a> than the original molecule. Increased lipophilicity makes these species more suitable for use in techniques such as <a href="/wiki/Polymerase_chain_reaction" title="Polymerase chain reaction">PCR</a>, <a href="/wiki/Aptamer" title="Aptamer">RNA aptamer</a> post-modification, <a href="/wiki/Antisense_RNA" title="Antisense RNA">antisense technology</a>, and for phasing <a href="/wiki/X-ray_crystallography" title="X-ray crystallography">X-ray crystallographic</a> data.<sup id="cite_ref-:0_27-1" class="reference"><a href="#cite_note-:0-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p><p>Similar to the 2' modifications in nature, a synthetic modification of ribose includes the addition of <a href="/wiki/Fluorine" title="Fluorine">fluorine</a> at the 2' position. This <a href="/wiki/Fluorinated" class="mw-redirect" title="Fluorinated">fluorinated</a> ribose acts similar to the methylated ribose because it is capable of suppressing immune stimulation depending on the location of the ribose in the DNA strand.<sup id="cite_ref-:3_26-1" class="reference"><a href="#cite_note-:3-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> The big difference between methylation and fluorination, is the latter only occurs through synthetic modifications. The addition of fluorine leads to an increase in the stabilization of the glycosidic bond and an increase of intramolecular hydrogen bonds.<sup id="cite_ref-:3_26-2" class="reference"><a href="#cite_note-:3-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Medical_uses">Medical uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ribose&action=edit&section=10" title="Edit section: Medical uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-ribose has been suggested for use in management of <a href="/wiki/Congestive_heart_failure" class="mw-redirect" title="Congestive heart failure">congestive heart failure</a><sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> (as well as other forms of heart disease) and for <a href="/wiki/Chronic_fatigue_syndrome" class="mw-redirect" title="Chronic fatigue syndrome">chronic fatigue syndrome</a> (CFS), also called myalgic encephalomyelitis (ME) in an open-label non-blinded, non-randomized, and non-crossover subjective study.<sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> </p><p>Supplemental <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-ribose can bypass part of the <a href="/wiki/Pentose_phosphate_pathway" title="Pentose phosphate pathway">pentose phosphate pathway</a>, an energy-producing pathway, to produce <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-ribose-5-phosphate. The enzyme <a href="/wiki/Glucose-6-phosphate_dehydrogenase" title="Glucose-6-phosphate dehydrogenase">glucose-6-phosphate-dehydrogenase</a> (G-6-PDH) is often in short supply in cells, but more so in diseased tissue, such as in <a href="/wiki/Cardiac_muscle" title="Cardiac muscle">myocardial</a> cells in patients with cardiac disease. The supply of <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-ribose in the <a href="/wiki/Mitochondrion" title="Mitochondrion">mitochondria</a> is directly correlated with ATP production; decreased <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-ribose supply reduces the amount of ATP being produced. Studies suggest that supplementing <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-ribose following tissue ischemia (e.g. myocardial ischemia) increases myocardial ATP production, and therefore mitochondrial function. Essentially, administering supplemental <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-ribose bypasses an enzymatic step in the pentose phosphate pathway by providing an alternate source of 5-phospho-<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-ribose 1-<a href="/wiki/Pyrophosphate" title="Pyrophosphate">pyrophosphate</a> for ATP production. Supplemental <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-ribose enhances recovery of ATP levels while also reducing cellular injury in humans and other animals. One study suggested that the use of supplemental <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-ribose reduces the instance of <a href="/wiki/Angina" title="Angina">angina</a> in men with diagnosed <a href="/wiki/Coronary_artery_disease" title="Coronary artery disease">coronary artery disease</a>.<sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-Ribose has been used to treat many <a href="/wiki/Pathological" class="mw-redirect" title="Pathological">pathological</a> conditions, such as chronic fatigue syndrome, <a href="/wiki/Fibromyalgia" title="Fibromyalgia">fibromyalgia</a>, and myocardial dysfunction. It is also used to reduce symptoms of cramping, pain, stiffness, etc. after exercise and to improve athletic performance<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (December 2019)">citation needed</span></a></i>]</sup>. </p> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ribose&action=edit&section=11" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><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 cs2"><i><a href="/wiki/Merck_Index" title="Merck Index">The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals</a></i> (11th ed.), Merck, 1989, <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/091191028X" title="Special:BookSources/091191028X"><bdi>091191028X</bdi></a></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Merck+Index%3A+An+Encyclopedia+of+Chemicals%2C+Drugs%2C+and+Biologicals&rft.edition=11th&rft.pub=Merck&rft.date=1989&rft.isbn=091191028X&rfr_id=info%3Asid%2Fen.wikipedia.org%3ARibose" class="Z3988"></span>, 8205</span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWeast1981" class="citation book cs1">Weast, Robert C., ed. (1981). <i>CRC Handbook of Chemistry and Physics</i> (62nd ed.). Boca Raton, FL: CRC Press. p. C-506. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-8493-0462-8" title="Special:BookSources/0-8493-0462-8"><bdi>0-8493-0462-8</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=CRC+Handbook+of+Chemistry+and+Physics&rft.place=Boca+Raton%2C+FL&rft.pages=C-506&rft.edition=62nd&rft.pub=CRC+Press&rft.date=1981&rft.isbn=0-8493-0462-8&rfr_id=info%3Asid%2Fen.wikipedia.org%3ARibose" 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="CITEREFFischerPiloty1891" class="citation journal cs1 cs1-prop-foreign-lang-source"><a href="/wiki/Emil_Fischer" title="Emil Fischer">Fischer, Emil</a>; <a href="/wiki/Oscar_Piloty" class="mw-redirect" title="Oscar Piloty">Piloty, Oscar</a> (1891). <a rel="nofollow" class="external text" href="https://zenodo.org/record/1589397">"Ueber eine neue Pentonsäure und die zweite inactive Trioxyglutarsäure"</a> [About a new pentonic acid and the second inactive trioxyglutaric acid]. <i><a href="/wiki/Berichte_der_deutschen_chemischen_Gesellschaft" class="mw-redirect" title="Berichte der deutschen chemischen Gesellschaft">Berichte der deutschen chemischen Gesellschaft</a></i> (in German). <b>24</b> (2): 4214–4225. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fcber.189102402322">10.1002/cber.189102402322</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200604184321/https://zenodo.org/record/1589397">Archived</a> from the original on 4 June 2020<span class="reference-accessdate">. Retrieved <span class="nowrap">12 March</span> 2020</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Berichte+der+deutschen+chemischen+Gesellschaft&rft.atitle=Ueber+eine+neue+Pentons%C3%A4ure+und+die+zweite+inactive+Trioxyglutars%C3%A4ure&rft.volume=24&rft.issue=2&rft.pages=4214-4225&rft.date=1891&rft_id=info%3Adoi%2F10.1002%2Fcber.189102402322&rft.aulast=Fischer&rft.aufirst=Emil&rft.au=Piloty%2C+Oscar&rft_id=https%3A%2F%2Fzenodo.org%2Frecord%2F1589397&rfr_id=info%3Asid%2Fen.wikipedia.org%3ARibose" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLeveneJacobs1909" class="citation journal cs1 cs1-prop-foreign-lang-source"><a href="/wiki/Phoebus_Levene" title="Phoebus Levene">Levene, P. A.</a>; <a href="/wiki/Walter_Abraham_Jacobs" title="Walter Abraham Jacobs">Jacobs, W. A.</a> (1909). "Über Inosinsäure" [About inosic acid]. <i><a href="/wiki/Berichte_der_deutschen_chemischen_Gesellschaft" class="mw-redirect" title="Berichte der deutschen chemischen Gesellschaft">Berichte der deutschen chemischen Gesellschaft</a></i> (in German). <b>42</b> (1): 1198–1203. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fcber.190904201196">10.1002/cber.190904201196</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Berichte+der+deutschen+chemischen+Gesellschaft&rft.atitle=%C3%9Cber+Inosins%C3%A4ure&rft.volume=42&rft.issue=1&rft.pages=1198-1203&rft.date=1909&rft_id=info%3Adoi%2F10.1002%2Fcber.190904201196&rft.aulast=Levene&rft.aufirst=P.+A.&rft.au=Jacobs%2C+W.+A.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ARibose" 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="CITEREFLeveneJacobs1909" class="citation journal cs1 cs1-prop-foreign-lang-source"><a href="/wiki/Phoebus_Levene" title="Phoebus Levene">Levene, P. A.</a>; <a href="/wiki/Walter_Abraham_Jacobs" title="Walter Abraham Jacobs">Jacobs, W. A.</a> (1909). "Über die Pentose in den Nucleinsäuren" [About the pentose in the nucleic acids]. <i><a href="/wiki/Berichte_der_deutschen_chemischen_Gesellschaft" class="mw-redirect" title="Berichte der deutschen chemischen Gesellschaft">Berichte der deutschen chemischen Gesellschaft</a></i> (in German). <b>42</b> (3): 3247–3251. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fcber.19090420351">10.1002/cber.19090420351</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Berichte+der+deutschen+chemischen+Gesellschaft&rft.atitle=%C3%9Cber+die+Pentose+in+den+Nucleins%C3%A4uren&rft.volume=42&rft.issue=3&rft.pages=3247-3251&rft.date=1909&rft_id=info%3Adoi%2F10.1002%2Fcber.19090420351&rft.aulast=Levene&rft.aufirst=P.+A.&rft.au=Jacobs%2C+W.+A.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ARibose" class="Z3988"></span></span> </li> <li id="cite_note-RiboseReview-6"><span class="mw-cite-backlink">^ <a href="#cite_ref-RiboseReview_6-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-RiboseReview_6-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJeanlozFletcher1951" class="citation book cs1"><a href="/wiki/Roger_W._Jeanloz" title="Roger W. Jeanloz">Jeanloz, Roger W.</a>; Fletcher, Hewitt G. (1951). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=W_sk8M7jtNsC&pg=PA135">"The Chemistry of Ribose"</a>. In <a href="/wiki/Claude_Hudson" title="Claude Hudson">Hudson, Claude S.</a>; Cantor, Sidney M. (eds.). <i>Advances in Carbohydrate Chemistry</i>. Vol. 6. <a href="/wiki/Academic_Press" title="Academic Press">Academic Press</a>. pp. 135–174. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0096-5332%2808%2960066-1">10.1016/S0096-5332(08)60066-1</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780080562650" title="Special:BookSources/9780080562650"><bdi>9780080562650</bdi></a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/14894350">14894350</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20231026175827/https://books.google.com/books?id=W_sk8M7jtNsC&pg=PA135#v=onepage&q&f=false">Archived</a> from the original on 26 October 2023<span class="reference-accessdate">. Retrieved <span class="nowrap">15 December</span> 2019</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=The+Chemistry+of+Ribose&rft.btitle=Advances+in+Carbohydrate+Chemistry&rft.pages=135-174&rft.pub=Academic+Press&rft.date=1951&rft_id=info%3Apmid%2F14894350&rft_id=info%3Adoi%2F10.1016%2FS0096-5332%2808%2960066-1&rft.isbn=9780080562650&rft.aulast=Jeanloz&rft.aufirst=Roger+W.&rft.au=Fletcher%2C+Hewitt+G.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DW_sk8M7jtNsC%26pg%3DPA135&rfr_id=info%3Asid%2Fen.wikipedia.org%3ARibose" class="Z3988"></span></span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFNechamkin1958" class="citation journal cs1">Nechamkin, Howard (1958). "Some interesting etymological derivations of chemical terminology". <i><a href="/wiki/Science_Education_(journal)" title="Science Education (journal)">Science Education</a></i>. <b>42</b> (5): 463–474. <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/1958SciEd..42..463N">1958SciEd..42..463N</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fsce.3730420523">10.1002/sce.3730420523</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Science+Education&rft.atitle=Some+interesting+etymological+derivations+of+chemical+terminology&rft.volume=42&rft.issue=5&rft.pages=463-474&rft.date=1958&rft_id=info%3Adoi%2F10.1002%2Fsce.3730420523&rft_id=info%3Abibcode%2F1958SciEd..42..463N&rft.aulast=Nechamkin&rft.aufirst=Howard&rfr_id=info%3Asid%2Fen.wikipedia.org%3ARibose" class="Z3988"></span></span> </li> <li id="cite_note-Dewick-8"><span class="mw-cite-backlink">^ <a href="#cite_ref-Dewick_8-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Dewick_8-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Dewick_8-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Dewick_8-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDewick2013" class="citation book cs1">Dewick, Paul M. (2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=RrKgfuRwsqsC&pg=PA227">"Oxygen as a Nucleophile: Hemicetals, Hemiketals, Acetals and Ketals"</a>. <i>Essentials of Organic Chemistry: For Students of Pharmacy, Medicinal Chemistry and Biological Chemistry</i>. <a href="/wiki/John_Wiley_%26_Sons" class="mw-redirect" title="John Wiley & Sons">John Wiley & Sons</a>. pp. 224–234. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9781118681961" title="Special:BookSources/9781118681961"><bdi>9781118681961</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20231026175827/https://books.google.com/books?id=RrKgfuRwsqsC&pg=PA227#v=onepage&q&f=false">Archived</a> from the original on 26 October 2023<span class="reference-accessdate">. Retrieved <span class="nowrap">15 December</span> 2019</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Oxygen+as+a+Nucleophile%3A+Hemicetals%2C+Hemiketals%2C+Acetals+and+Ketals&rft.btitle=Essentials+of+Organic+Chemistry%3A+For+Students+of+Pharmacy%2C+Medicinal+Chemistry+and+Biological+Chemistry&rft.pages=224-234&rft.pub=John+Wiley+%26+Sons&rft.date=2013&rft.isbn=9781118681961&rft.aulast=Dewick&rft.aufirst=Paul+M.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DRrKgfuRwsqsC%26pg%3DPA227&rfr_id=info%3Asid%2Fen.wikipedia.org%3ARibose" class="Z3988"></span></span> </li> <li id="cite_note-ChemInt-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-ChemInt_9-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLeigh2012" class="citation journal cs1">Leigh, Jeffery (July–August 2012). <a rel="nofollow" class="external text" href="http://publications.iupac.org/ci/2012/3404/nn.html">"Non-IUPAC Nomenclature Systems"</a>. <i><a href="/wiki/Chemistry_International" title="Chemistry International">Chemistry International</a></i>. <b>34</b> (4). <a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">International Union of Pure and Applied Chemistry</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20191205030458/http://publications.iupac.org/ci/2012/3404/nn.html">Archived</a> from the original on 5 December 2019<span class="reference-accessdate">. Retrieved <span class="nowrap">15 December</span> 2019</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemistry+International&rft.atitle=Non-IUPAC+Nomenclature+Systems&rft.volume=34&rft.issue=4&rft.date=2012-07%2F2012-08&rft.aulast=Leigh&rft.aufirst=Jeffery&rft_id=http%3A%2F%2Fpublications.iupac.org%2Fci%2F2012%2F3404%2Fnn.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ARibose" class="Z3988"></span></span> </li> <li id="cite_note-Bhutani-10"><span class="mw-cite-backlink">^ <a href="#cite_ref-Bhutani_10-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Bhutani_10-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Bhutani_10-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBhutani2019" class="citation book cs1">Bhutani, S. P. 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"The use of ᴅ-ribose in chronic fatigue syndrome and fibromyalgia: a pilot study". <i>The Journal of Alternative and Complementary Medicine</i>. <b>12</b> (9): 857–862. <a href="/wiki/CiteSeerX_(identifier)" class="mw-redirect" title="CiteSeerX (identifier)">CiteSeerX</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://citeseerx.ist.psu.edu/viewdoc/summary?doi=10.1.1.582.4800">10.1.1.582.4800</a></span>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1089%2Facm.2006.12.857">10.1089/acm.2006.12.857</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/17109576">17109576</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Alternative+and+Complementary+Medicine&rft.atitle=The+use+of+%E1%B4%85-ribose+in+chronic+fatigue+syndrome+and+fibromyalgia%3A+a+pilot+study.&rft.volume=12&rft.issue=9&rft.pages=857-862&rft.date=2006-11-26&rft_id=https%3A%2F%2Fciteseerx.ist.psu.edu%2Fviewdoc%2Fsummary%3Fdoi%3D10.1.1.582.4800%23id-name%3DCiteSeerX&rft_id=info%3Apmid%2F17109576&rft_id=info%3Adoi%2F10.1089%2Facm.2006.12.857&rft.aulast=Teitelbaum&rft.aufirst=Jacob+E.&rft.au=Johnson%2C+Clarence&rft.au=St+Cyr%2C+John&rfr_id=info%3Asid%2Fen.wikipedia.org%3ARibose" class="Z3988"></span></span> </li> <li id="cite_note-31"><span class="mw-cite-backlink"><b><a href="#cite_ref-31">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://wa.kaiserpermanente.org/kbase/topic.jhtml?docId=hn-3949001">"Ribose"</a>. <i>wa.kaiserpermanente.org</i>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20210303060923/https://wa.kaiserpermanente.org/kbase/topic.jhtml?docId=hn-3949001">Archived</a> from the original on 3 March 2021<span class="reference-accessdate">. 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.navbox{display:none!important}}</style></div><div role="navigation" class="navbox" aria-labelledby="Types_of_carbohydrates" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><style data-mw-deduplicate="TemplateStyles:r1239400231">.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Carbohydrates" title="Template:Carbohydrates"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Carbohydrates" title="Template talk:Carbohydrates"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Carbohydrates" title="Special:EditPage/Template:Carbohydrates"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Types_of_carbohydrates" style="font-size:114%;margin:0 4em">Types of <a href="/wiki/Carbohydrate" title="Carbohydrate">carbohydrates</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">General</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/Aldose" title="Aldose">Aldose</a></li> <li><a href="/wiki/Ketose" title="Ketose">Ketose</a></li> <li><a href="/wiki/Furanose" title="Furanose">Furanose</a></li> <li><a href="/wiki/Pyranose" title="Pyranose">Pyranose</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Geometry</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/Anomer" title="Anomer">Anomer</a></li> <li><a href="/wiki/Cyclohexane_conformation" title="Cyclohexane conformation">Cyclohexane conformation</a></li> <li><a href="/wiki/Epimer" title="Epimer">Epimer</a></li> <li><a href="/wiki/Mutarotation" title="Mutarotation">Mutarotation</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Monosaccharide" title="Monosaccharide">Monosaccharides</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Diose" title="Diose">Dioses</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Aldodiose <ul><li><a href="/wiki/Glycolaldehyde" title="Glycolaldehyde">Glycolaldehyde</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Triose" title="Triose">Trioses</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Aldotriose <ul><li><a href="/wiki/Glyceraldehyde" title="Glyceraldehyde">Glyceraldehyde</a></li></ul></li> <li>Ketotriose <ul><li><a href="/wiki/Dihydroxyacetone" title="Dihydroxyacetone">Dihydroxyacetone</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tetrose" title="Tetrose">Tetroses</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Aldotetroses <ul><li><a href="/wiki/Erythrose" title="Erythrose">Erythrose</a></li> <li><a href="/wiki/Threose" title="Threose">Threose</a></li></ul></li> <li>Ketotetrose <ul><li><a href="/wiki/Erythrulose" title="Erythrulose">Erythrulose</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Pentose" title="Pentose">Pentoses</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Aldopentoses <ul><li><a href="/wiki/Arabinose" title="Arabinose">Arabinose</a></li> <li><a href="/wiki/Lyxose" title="Lyxose">Lyxose</a></li> <li><a class="mw-selflink selflink">Ribose</a></li> <li><a href="/wiki/Xylose" title="Xylose">Xylose</a></li></ul></li> <li>Ketopentoses <ul><li><a href="/wiki/Ribulose" title="Ribulose">Ribulose</a></li> <li><a href="/wiki/Xylulose" title="Xylulose">Xylulose</a></li></ul></li> <li><a href="/wiki/Deoxy_sugar" title="Deoxy sugar">Deoxy sugars</a> <ul><li><a href="/wiki/Deoxyribose" title="Deoxyribose">Deoxyribose</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hexose" title="Hexose">Hexoses</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aldohexose" class="mw-redirect" title="Aldohexose">Aldohexoses</a> <ul><li><a href="/wiki/Allose" title="Allose">Allose</a></li> <li><a href="/wiki/Altrose" title="Altrose">Altrose</a></li> <li><a href="/wiki/Galactose" title="Galactose">Galactose</a></li> <li><a href="/wiki/Glucose" title="Glucose">Glucose</a></li> <li><a href="/wiki/Gulose" title="Gulose">Gulose</a></li> <li><a href="/wiki/Idose" title="Idose">Idose</a></li> <li><a href="/wiki/Mannose" title="Mannose">Mannose</a></li> <li><a href="/wiki/Talose" title="Talose">Talose</a></li></ul></li> <li><a href="/wiki/Ketohexose" class="mw-redirect" title="Ketohexose">Ketohexoses</a> <ul><li><a href="/wiki/Fructose" title="Fructose">Fructose</a></li> <li><a href="/wiki/Psicose" title="Psicose">Psicose</a></li> <li><a href="/wiki/Sorbose" title="Sorbose">Sorbose</a></li> <li><a href="/wiki/Tagatose" title="Tagatose">Tagatose</a></li></ul></li> <li>Deoxy sugars <ul><li><a href="/wiki/Fucose" title="Fucose">Fucose</a></li> <li><a href="/wiki/Fuculose" title="Fuculose">Fuculose</a></li> <li><a href="/wiki/Rhamnose" title="Rhamnose">Rhamnose</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Heptose" title="Heptose">Heptoses</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Ketoheptoses <ul><li><a href="/wiki/Mannoheptulose" title="Mannoheptulose">Mannoheptulose</a></li> <li><a href="/wiki/Sedoheptulose" title="Sedoheptulose">Sedoheptulose</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Above 7</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/Octose" title="Octose">Octoses</a></li> <li><a href="/wiki/Nonose" title="Nonose">Nonoses</a> <ul><li><a href="/wiki/Neuraminic_acid" title="Neuraminic acid">Neuraminic acid</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Multiple</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Disaccharide" title="Disaccharide">Disaccharides</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cellobiose" title="Cellobiose">Cellobiose</a></li> <li><a href="/wiki/Isomaltose" title="Isomaltose">Isomaltose</a></li> <li><a href="/wiki/Isomaltulose" title="Isomaltulose">Isomaltulose</a></li> <li><a href="/wiki/Lactose" title="Lactose">Lactose</a></li> <li><a href="/wiki/Lactulose" title="Lactulose">Lactulose</a></li> <li><a href="/wiki/Maltose" title="Maltose">Maltose</a></li> <li><a href="/wiki/Sucrose" title="Sucrose">Sucrose</a></li> <li><a href="/wiki/Trehalose" title="Trehalose">Trehalose</a></li> <li><a href="/wiki/Turanose" title="Turanose">Turanose</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Trisaccharide" title="Trisaccharide">Trisaccharides</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Maltotriose" title="Maltotriose">Maltotriose</a></li> <li><a href="/wiki/Melezitose" title="Melezitose">Melezitose</a></li> <li><a href="/wiki/Raffinose" title="Raffinose">Raffinose</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tetrasaccharide" title="Tetrasaccharide">Tetrasaccharides</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Stachyose" title="Stachyose">Stachyose</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other<br /> <a href="/wiki/Oligosaccharide" title="Oligosaccharide">oligosaccharides</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acarbose" title="Acarbose">Acarbose</a></li> <li><a href="/wiki/Fructooligosaccharide" title="Fructooligosaccharide">Fructooligosaccharide</a> (FOS)</li> <li><a href="/wiki/Galactooligosaccharide" title="Galactooligosaccharide">Galactooligosaccharide</a> (GOS)</li> <li><a href="/wiki/Isomaltooligosaccharide" title="Isomaltooligosaccharide">Isomaltooligosaccharide</a> (IMO)</li> <li><a href="/wiki/Maltodextrin" title="Maltodextrin">Maltodextrin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Polysaccharide" title="Polysaccharide">Polysaccharides</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Beta-glucan" title="Beta-glucan">Beta-glucan</a> <ul><li><a href="/wiki/Oat_beta-glucan" title="Oat beta-glucan">Oat beta-glucan</a></li> <li><a href="/wiki/Lentinan" title="Lentinan">Lentinan</a></li> <li><a href="/wiki/Schizophyllan" title="Schizophyllan">Sizofiran</a></li> <li><a href="/wiki/Zymosan" title="Zymosan">Zymosan</a></li> <li><a href="/wiki/Cellulose" title="Cellulose">Cellulose</a></li> <li><a href="/wiki/Chitin" title="Chitin">Chitin</a></li></ul></li> <li><a href="/wiki/Chitosan" title="Chitosan">Chitosan</a></li> <li><a href="/wiki/Dextrin" title="Dextrin">Dextrin</a> / <a href="/wiki/Dextran" title="Dextran">Dextran</a></li> <li><i><a href="/wiki/Fructose" title="Fructose">Fructose</a> / <a href="/wiki/Fructan" title="Fructan">Fructan</a></i> <ul><li><a href="/wiki/Inulin" title="Inulin">Inulin</a></li></ul></li> <li><i><a href="/wiki/Galactose" title="Galactose">Galactose</a> / <a href="/wiki/Galactose" title="Galactose">Galactan</a></i></li> <li><i><a href="/wiki/Glucose" title="Glucose">Glucose</a> / <a href="/wiki/Glucan" title="Glucan">Glucan</a></i> <ul><li><a href="/wiki/Glycogen" title="Glycogen">Glycogen</a></li></ul></li> <li><a href="/wiki/Hemicellulose" title="Hemicellulose">Hemicellulose</a></li> <li><a href="/wiki/Levan_polysaccharide" title="Levan polysaccharide">Levan beta 2→6</a></li> <li><a href="/wiki/Lignin" title="Lignin">Lignin</a></li> <li><a href="/wiki/Mannans" title="Mannans">Mannan</a></li> <li><a href="/wiki/Pectin" title="Pectin">Pectin</a></li> <li><a href="/wiki/Starch" title="Starch">Starch</a> <ul><li><a href="/wiki/Amylopectin" title="Amylopectin">Amylopectin</a></li> <li><a href="/wiki/Amylose" title="Amylose">Amylose</a></li></ul></li> <li><a href="/wiki/Xanthan_gum" title="Xanthan gum">Xanthan gum</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/23px-Symbol_category_class.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/31px-Symbol_category_class.svg.png 2x" data-file-width="180" data-file-height="185" /></span></span> <a href="/wiki/Category:Carbohydrates" title="Category:Carbohydrates">Category</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 class="mw-selflink selflink">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 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