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Cyclic adenosine monophosphate - Wikipedia
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class="vector-toc-numb">4</span> <span>Pathology</span> </div> </a> <button aria-controls="toc-Pathology-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 Pathology subsection</span> </button> <ul id="toc-Pathology-sublist" class="vector-toc-list"> <li id="toc-Role_in_human_carcinoma" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Role_in_human_carcinoma"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Role in human carcinoma</span> </div> </a> <ul id="toc-Role_in_human_carcinoma-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Role_in_prefrontal_cortex_disorders" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Role_in_prefrontal_cortex_disorders"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Role in prefrontal cortex disorders</span> </div> </a> <ul id="toc-Role_in_prefrontal_cortex_disorders-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Role_in_infectious_disease_agents'_pathogenesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Role_in_infectious_disease_agents'_pathogenesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.3</span> <span>Role in infectious disease agents' pathogenesis</span> </div> </a> <ul id="toc-Role_in_infectious_disease_agents'_pathogenesis-sublist" class="vector-toc-list"> <li id="toc-ADP-ribosyl-transferases_related_toxins" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#ADP-ribosyl-transferases_related_toxins"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.3.1</span> <span>ADP-ribosyl-transferases related toxins</span> </div> </a> <ul id="toc-ADP-ribosyl-transferases_related_toxins-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-Uses" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Uses</span> </div> </a> <ul id="toc-Uses-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> </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">Cyclic adenosine monophosphate</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 41 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-41" 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">41 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%A3%D8%AD%D8%A7%D8%AF%D9%8A_%D9%81%D9%88%D8%B3%D9%81%D8%A7%D8%AA_%D8%A7%D9%84%D8%A3%D8%AF%D9%8A%D9%86%D9%88%D8%B3%D9%8A%D9%86_%D8%A7%D9%84%D8%AD%D9%84%D9%82%D9%8A" title="أحادي فوسفات الأدينوسين الحلقي – Arabic" lang="ar" hreflang="ar" data-title="أحادي فوسفات الأدينوسين الحلقي" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%A2%D8%AF%D9%86%D9%88%D8%B2%DB%8C%D9%86_%D9%85%D9%88%D9%86%D9%88%D9%81%D9%88%D8%B3%D9%81%D8%A7%D8%AA_%D8%AD%D9%84%D9%82%D9%87%E2%80%8C%D8%A7%DB%8C" title="آدنوزین مونوفوسفات حلقهای – South Azerbaijani" lang="azb" hreflang="azb" data-title="آدنوزین مونوفوسفات حلقهای" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%A6%D0%B8%D0%BA%D0%BB%D0%B8%D1%87%D0%B5%D0%BD_%D0%B0%D0%B4%D0%B5%D0%BD%D0%BE%D0%B7%D0%B8%D0%BD%D0%BC%D0%BE%D0%BD%D0%BE%D1%84%D0%BE%D1%81%D1%84%D0%B0%D1%82" title="Цикличен аденозинмонофосфат – Bulgarian" lang="bg" hreflang="bg" data-title="Цикличен аденозинмонофосфат" 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/Cikli%C4%8Dni_adenozin-monofosfat" title="Ciklični adenozin-monofosfat – Bosnian" lang="bs" hreflang="bs" data-title="Ciklični adenozin-monofosfat" 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/Monofosfat_d%27adenosina_c%C3%ADclic" title="Monofosfat d'adenosina cíclic – Catalan" lang="ca" hreflang="ca" data-title="Monofosfat d'adenosina cíclic" 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/Cyklick%C3%BD_adenosinmonofosf%C3%A1t" title="Cyklický adenosinmonofosfát – Czech" lang="cs" hreflang="cs" data-title="Cyklický adenosinmonofosfát" 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/CAMP" title="CAMP – Danish" lang="da" hreflang="da" data-title="CAMP" 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/Cyclisches_Adenosinmonophosphat" title="Cyclisches Adenosinmonophosphat – German" lang="de" hreflang="de" data-title="Cyclisches Adenosinmonophosphat" 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/Ts%C3%BCkliline_adenosiinmonofosfaat" title="Tsükliline adenosiinmonofosfaat – Estonian" lang="et" hreflang="et" data-title="Tsükliline adenosiinmonofosfaat" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Adenos%C3%ADn_monofosfato_c%C3%ADclico" title="Adenosín monofosfato cíclico – Spanish" lang="es" hreflang="es" data-title="Adenosín monofosfato cíclico" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Adenosin_monofosfato_zikliko" title="Adenosin monofosfato zikliko – Basque" lang="eu" hreflang="eu" data-title="Adenosin monofosfato zikliko" 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%A2%D8%AF%D9%86%D9%88%D8%B2%DB%8C%D9%86_%D9%85%D9%86%D9%88%D9%81%D8%B3%D9%81%D8%A7%D8%AA_%D8%AD%D9%84%D9%82%D9%87%E2%80%8C%D8%A7%DB%8C" title="آدنوزین منوفسفات حلقهای – Persian" lang="fa" hreflang="fa" data-title="آدنوزین منوفسفات حلقهای" 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/Ad%C3%A9nosine_monophosphate_cyclique" title="Adénosine monophosphate cyclique – French" lang="fr" hreflang="fr" data-title="Adénosine monophosphate cyclique" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Adenos%C3%ADn_monofosfato_c%C3%ADclico" title="Adenosín monofosfato cíclico – Galician" lang="gl" hreflang="gl" data-title="Adenosín monofosfato cíclico" 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/%EA%B3%A0%EB%A6%AC%ED%98%95_%EC%95%84%EB%8D%B0%EB%85%B8%EC%8B%A0_%EC%9D%BC%EC%9D%B8%EC%82%B0" title="고리형 아데노신 일인산 – Korean" lang="ko" hreflang="ko" data-title="고리형 아데노신 일인산" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Cikli%C4%8Dki_adenozin_monofosfat" title="Ciklički adenozin monofosfat – Croatian" lang="hr" hreflang="hr" data-title="Ciklički adenozin monofosfat" 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/Adenosina_monofosfat_siklik" title="Adenosina monofosfat siklik – Indonesian" lang="id" hreflang="id" data-title="Adenosina monofosfat siklik" 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/Adenosina_monofosfato_ciclico" title="Adenosina monofosfato ciclico – Italian" lang="it" hreflang="it" data-title="Adenosina monofosfato ciclico" 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/CAMP" title="CAMP – Hebrew" lang="he" hreflang="he" data-title="CAMP" 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/Adenosina_monofosfat_siklik" title="Adenosina monofosfat siklik – Javanese" lang="jv" hreflang="jv" data-title="Adenosina monofosfat siklik" data-language-autonym="Jawa" data-language-local-name="Javanese" class="interlanguage-link-target"><span>Jawa</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%A6%D0%B8%D0%BA%D0%BB%D0%B4%D1%8B_%D0%B0%D0%B4%D0%B5%D0%BD%D0%BE%D0%B7%D0%B8%D0%BD%D0%BC%D0%BE%D0%BD%D0%BE%D1%84%D0%BE%D1%81%D1%84%D0%B0%D1%82" title="Циклды аденозинмонофосфат – Kazakh" lang="kk" hreflang="kk" data-title="Циклды аденозинмонофосфат" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/CAMP" title="CAMP – Lithuanian" lang="lt" hreflang="lt" data-title="CAMP" 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/Ciklikus_adenozin-monofoszf%C3%A1t" title="Ciklikus adenozin-monofoszfát – Hungarian" lang="hu" hreflang="hu" data-title="Ciklikus adenozin-monofoszfát" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Cyclisch_adenosinemonofosfaat" title="Cyclisch adenosinemonofosfaat – Dutch" lang="nl" hreflang="nl" data-title="Cyclisch adenosinemonofosfaat" 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/%E7%92%B0%E7%8A%B6%E3%82%A2%E3%83%87%E3%83%8E%E3%82%B7%E3%83%B3%E4%B8%80%E3%83%AA%E3%83%B3%E9%85%B8" title="環状アデノシン一リン酸 – Japanese" lang="ja" hreflang="ja" data-title="環状アデノシン一リン酸" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Syklisk_AMP" title="Syklisk AMP – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Syklisk AMP" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Adenosina_monofosfat_ciclic" title="Adenosina monofosfat ciclic – Occitan" lang="oc" hreflang="oc" data-title="Adenosina monofosfat ciclic" data-language-autonym="Occitan" data-language-local-name="Occitan" class="interlanguage-link-target"><span>Occitan</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Cykliczny_adenozyno-3%E2%80%B2,5%E2%80%B2-monofosforan" title="Cykliczny adenozyno-3′,5′-monofosforan – Polish" lang="pl" hreflang="pl" data-title="Cykliczny adenozyno-3′,5′-monofosforan" 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/Monofosfato_c%C3%ADclico_de_adenosina" title="Monofosfato cíclico de adenosina – Portuguese" lang="pt" hreflang="pt" data-title="Monofosfato cíclico de adenosina" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%A6%D0%B8%D0%BA%D0%BB%D0%B8%D1%87%D0%B5%D1%81%D0%BA%D0%B8%D0%B9_%D0%B0%D0%B4%D0%B5%D0%BD%D0%BE%D0%B7%D0%B8%D0%BD%D0%BC%D0%BE%D0%BD%D0%BE%D1%84%D0%BE%D1%81%D1%84%D0%B0%D1%82" title="Циклический аденозинмонофосфат – Russian" lang="ru" hreflang="ru" data-title="Циклический аденозинмонофосфат" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Cyklick%C3%BD_adenoz%C3%ADnmonofosf%C3%A1t" title="Cyklický adenozínmonofosfát – Slovak" lang="sk" hreflang="sk" data-title="Cyklický adenozínmonofosfát" 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/Cikli%C4%8Dni_AMP" title="Ciklični AMP – Slovenian" lang="sl" hreflang="sl" data-title="Ciklični AMP" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%A6%D0%B8%D0%BA%D0%BB%D0%B8%D1%87%D0%BD%D0%B8_%D0%B0%D0%B4%D0%B5%D0%BD%D0%BE%D0%B7%D0%B8%D0%BD_%D0%BC%D0%BE%D0%BD%D0%BE%D1%84%D0%BE%D1%81%D1%84%D0%B0%D1%82" title="Циклични аденозин монофосфат – Serbian" lang="sr" hreflang="sr" data-title="Циклични аденозин монофосфат" 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 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.ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> <table class="infobox ib-chembox"> <caption>Cyclic adenosine monophosphate </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:CAMP.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/CAMP.svg/220px-CAMP.svg.png" decoding="async" width="220" height="220" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/CAMP.svg/330px-CAMP.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/CAMP.svg/440px-CAMP.svg.png 2x" data-file-width="304" data-file-height="304" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Cyclic-adenosine-monophosphate-from-xtal-3D-bs-17.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Cyclic-adenosine-monophosphate-from-xtal-3D-bs-17.png/220px-Cyclic-adenosine-monophosphate-from-xtal-3D-bs-17.png" decoding="async" width="220" height="198" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Cyclic-adenosine-monophosphate-from-xtal-3D-bs-17.png/330px-Cyclic-adenosine-monophosphate-from-xtal-3D-bs-17.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Cyclic-adenosine-monophosphate-from-xtal-3D-bs-17.png/440px-Cyclic-adenosine-monophosphate-from-xtal-3D-bs-17.png 2x" data-file-width="2555" data-file-height="2297" /></a></span> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">Adenosine 3′,5′-(hydrogen phosphate)</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;">(4a<i>R</i>,6<i>R</i>,7<i>R</i>,7a<i>S</i>)-6-(6-Amino-9<i>H</i>-purin-9-yl)-2,7-dihydroxytetrahydro-2<i>H</i>,4<i>H</i>-2λ<sup>5</sup>-furo[3,2-<i>d</i>][1,3,2]dioxaphosphinin-2-one</div></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=60-92-4">60-92-4</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=c1nc%28c2c%28n1%29n%28cn2%29%5BC%40H%5D3%5BC%40%40H%5D%28%5BC%40H%5D4%5BC%40H%5D%28O3%29COP%28%3DO%29%28O4%29O%29O%29N">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=17489">CHEBI:17489</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL316966">ChEMBL316966</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.5851.html">5851</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB02527">DB02527</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.000.448">100.000.448</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q210041#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/IUPHAR/BPS" class="mw-redirect" title="IUPHAR/BPS">IUPHAR/BPS</a></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.guidetopharmacology.org"><a rel="nofollow" class="external text" href="http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?tab=summary&ligandId=2352">2352</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C00575">C00575</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Medical_Subject_Headings" title="Medical Subject Headings">MeSH</a> </td> <td><span title="www.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://www.nlm.nih.gov/cgi/mesh/2014/MB_cgi?mode=&term=Cyclic+AMP">Cyclic+AMP</a></span> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/6076">6076</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/E0399OZS9N">E0399OZS9N</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID8040436">DTXSID8040436</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q210041#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C10H12N5O6P/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7-4(20-10)1-19-22(17,18)21-7/h2-4,6-7,10,16H,1H2,(H,17,18)(H2,11,12,13)/t4-,6-,7-,10-/m1/s1<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: IVOMOUWHDPKRLL-KQYNXXCUSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/C10H12N5O6P/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7-4(20-10)1-19-22(17,18)21-7/h2-4,6-7,10,16H,1H2,(H,17,18)(H2,11,12,13)/t4-,6-,7-,10-/m1/s1</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: IVOMOUWHDPKRLL-KQYNXXCUBU</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%;">c1nc(c2c(n1)n(cn2)[C@H]3[C@@H]([C@H]4[C@H](O3)COP(=O)(O4)O)O)N</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td>C<sub>10</sub>H<sub>11</sub>N<sub>5</sub>O<sub>6</sub>P  </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td>329.206 g/mol    </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/12px-Yes_check.svg.png" decoding="async" width="12" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/18px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/24px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=476994238&page2=Cyclic+adenosine+monophosphate">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:CAMP.PNG" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c9/CAMP.PNG/220px-CAMP.PNG" decoding="async" width="220" height="140" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c9/CAMP.PNG/330px-CAMP.PNG 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c9/CAMP.PNG/440px-CAMP.PNG 2x" data-file-width="878" data-file-height="558" /></a><figcaption>cAMP represented in three ways</figcaption></figure> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:ATP_chemical_structure.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/10/ATP_chemical_structure.png/220px-ATP_chemical_structure.png" decoding="async" width="220" height="122" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/10/ATP_chemical_structure.png/330px-ATP_chemical_structure.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/10/ATP_chemical_structure.png/440px-ATP_chemical_structure.png 2x" data-file-width="3718" data-file-height="2067" /></a><figcaption><a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">Adenosine triphosphate</a></figcaption></figure> <p><b>Cyclic adenosine monophosphate</b> (<b>cAMP</b>, <b>cyclic AMP</b>, or <b>3',5'-cyclic <a href="/wiki/Adenosine_monophosphate" title="Adenosine monophosphate">adenosine monophosphate</a></b>) is a <a href="/wiki/Second_messenger" class="mw-redirect" title="Second messenger">second messenger</a>, or cellular signal occurring within cells, that is important in many biological processes. cAMP is a derivative of <a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">adenosine triphosphate</a> (ATP) and used for intracellular <a href="/wiki/Signal_transduction" title="Signal transduction">signal transduction</a> in many different organisms, conveying the <a href="/wiki/CAMP-dependent_pathway" title="CAMP-dependent pathway">cAMP-dependent pathway</a>. </p> <style data-mw-deduplicate="TemplateStyles:r886046785">.mw-parser-output .toclimit-2 .toclevel-1 ul,.mw-parser-output .toclimit-3 .toclevel-2 ul,.mw-parser-output .toclimit-4 .toclevel-3 ul,.mw-parser-output .toclimit-5 .toclevel-4 ul,.mw-parser-output .toclimit-6 .toclevel-5 ul,.mw-parser-output .toclimit-7 .toclevel-6 ul{display:none}</style><div class="toclimit-3"><meta property="mw:PageProp/toc" /></div> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyclic_adenosine_monophosphate&action=edit&section=1" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Earl_Sutherland" class="mw-redirect" title="Earl Sutherland">Earl Sutherland</a> of <a href="/wiki/Vanderbilt_University" title="Vanderbilt University">Vanderbilt University</a> won a <a href="/wiki/Nobel_Prize_in_Physiology_or_Medicine" title="Nobel Prize in Physiology or Medicine">Nobel Prize in Physiology or Medicine</a> in 1971 "for his discoveries concerning the mechanisms of the action of hormones", especially epinephrine, via <a href="/wiki/Second_messenger" class="mw-redirect" title="Second messenger">second messengers</a> (such as cyclic adenosine monophosphate, cyclic AMP). </p> <div class="mw-heading mw-heading2"><h2 id="Synthesis">Synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyclic_adenosine_monophosphate&action=edit&section=2" title="Edit section: Synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The synthesis of cAMP is stimulated by trophic hormones that bind to receptors on cell surface. cAMP levels reach maximal levels within minutes and decrease gradually over an hour in cultured cells.<sup id="cite_ref-1990-Hanukoglu_1-0" class="reference"><a href="#cite_note-1990-Hanukoglu-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Cyclic <a href="/wiki/Adenosine_monophosphate" title="Adenosine monophosphate">AMP</a> is synthesized from <a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a> by <a href="/wiki/Adenylate_cyclase" class="mw-redirect" title="Adenylate cyclase">adenylate cyclase</a> located on the inner side of the plasma membrane and anchored at various locations in the interior of the cell.<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> Adenylate cyclase is <i>activated</i> by a range of signaling molecules through the activation of adenylate cyclase stimulatory G (<a href="/wiki/Gs_alpha_subunit" title="Gs alpha subunit">G<sub>s</sub></a>)-protein-coupled receptors. Adenylate cyclase is <i>inhibited</i> by agonists of adenylate cyclase inhibitory G (<a href="/wiki/Gi_alpha_subunit" title="Gi alpha subunit">G<sub>i</sub></a>)-protein-coupled receptors. Liver adenylate cyclase responds more strongly to glucagon, and muscle adenylate cyclase responds more strongly to adrenaline. </p><p>cAMP decomposition into <a href="/wiki/Adenosine_monophosphate" title="Adenosine monophosphate">AMP</a> is catalyzed by the enzyme <a href="/wiki/Phosphodiesterase" title="Phosphodiesterase">phosphodiesterase</a>. </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=Cyclic_adenosine_monophosphate&action=edit&section=3" title="Edit section: Functions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>cAMP is a <a href="/wiki/Second_messenger_system" title="Second messenger system">second messenger</a>, used for intracellular signal transduction, such as <a href="/wiki/Second_messenger_system" title="Second messenger system">transferring</a> into cells the effects of <a href="/wiki/Hormone" title="Hormone">hormones</a> like <a href="/wiki/Glucagon" title="Glucagon">glucagon</a> and <a href="/wiki/Adrenaline" title="Adrenaline">adrenaline</a>, which cannot pass through the plasma membrane. It is also involved in the activation of <a href="/wiki/Protein_kinase" title="Protein kinase">protein kinases</a>. In addition, cAMP <a href="/wiki/Ligand_(biochemistry)" title="Ligand (biochemistry)">binds to</a> and regulates the function of <a href="/wiki/Ion_channels" class="mw-redirect" title="Ion channels">ion channels</a> such as the <a href="/wiki/HCN_channel" title="HCN channel">HCN channels</a> and a few other <a href="/wiki/Cyclic_nucleotide-binding_domain" title="Cyclic nucleotide-binding domain">cyclic nucleotide-binding proteins</a> such as <a href="/wiki/RAPGEF3" title="RAPGEF3">Epac1</a> and <a href="/wiki/RAPGEF2" title="RAPGEF2">RAPGEF2</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Role_in_eukaryotic_cells">Role in eukaryotic cells</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyclic_adenosine_monophosphate&action=edit&section=4" title="Edit section: Role in eukaryotic cells"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Function_of_cAMP-dependent_protein_kinase" class="mw-redirect" title="Function of cAMP-dependent protein kinase">function of cAMP-dependent protein kinase</a></div> <p>cAMP is associated with kinases function in several biochemical processes, including the regulation of <a href="/wiki/Glycogen" title="Glycogen">glycogen</a>, <a href="/wiki/Sugar" title="Sugar">sugar</a>, and <a href="/wiki/Lipid" title="Lipid">lipid</a> <a href="/wiki/Metabolism" title="Metabolism">metabolism</a>.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>In eukaryotes, cyclic AMP works by activating protein kinase A (PKA, or <a href="/wiki/CAMP-dependent_protein_kinase" class="mw-redirect" title="CAMP-dependent protein kinase">cAMP-dependent protein kinase</a>). PKA is normally inactive as a tetrameric <a href="/wiki/Holoenzyme" class="mw-redirect" title="Holoenzyme">holoenzyme</a>, consisting of two <a href="/wiki/Catalysis" title="Catalysis">catalytic</a> and two regulatory units (C<sub>2</sub>R<sub>2</sub>), with the regulatory units blocking the catalytic centers of the catalytic units. </p><p>Cyclic AMP binds to specific locations on the regulatory units of the protein kinase, and causes dissociation between the regulatory and catalytic subunits, thus enabling those catalytic units to <a href="/wiki/Phosphorylate" class="mw-redirect" title="Phosphorylate">phosphorylate</a> substrate proteins. </p><p>The active subunits catalyze the transfer of phosphate from ATP to specific <a href="/wiki/Serine" title="Serine">serine</a> or <a href="/wiki/Threonine" title="Threonine">threonine</a> residues of protein substrates. The phosphorylated proteins may act directly on the cell's ion channels, or may become activated or inhibited enzymes. Protein kinase A can also phosphorylate specific proteins that bind to promoter regions of DNA, causing increases in transcription. Not all protein kinases respond to cAMP. Several classes of <a href="/wiki/Protein_kinase" title="Protein kinase">protein kinases</a>, including protein kinase C, are not cAMP-dependent. </p><p>Further effects mainly depend on <a href="/wiki/Function_of_cAMP-dependent_protein_kinase" class="mw-redirect" title="Function of cAMP-dependent protein kinase">cAMP-dependent protein kinase</a>, which vary based on the type of cell. </p><p>Still, there are some minor PKA-independent functions of cAMP, e.g., activation of <a href="/wiki/Calcium_channel" title="Calcium channel">calcium channels</a>, providing a minor pathway by which <a href="/wiki/Growth_hormone-releasing_hormone" class="mw-redirect" title="Growth hormone-releasing hormone">growth hormone-releasing hormone</a> causes a release of <a href="/wiki/Growth_hormone" title="Growth hormone">growth hormone</a>. </p><p>However, the view that the majority of the effects of cAMP are controlled by PKA is an outdated one. In 1998 a family of cAMP-sensitive proteins with <a href="/wiki/Guanine_nucleotide_exchange_factor" title="Guanine nucleotide exchange factor">guanine nucleotide exchange factor</a> (GEF) activity was discovered. These are termed Exchange proteins activated by cAMP (Epac) and the family comprises <a href="/wiki/RAPGEF3" title="RAPGEF3">Epac1</a> and <a href="/wiki/RAPGEF4" title="RAPGEF4">Epac2</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> The mechanism of activation is similar to that of PKA: the GEF domain is usually masked by the N-terminal region containing the cAMP binding domain. When cAMP binds, the domain dissociates and exposes the now-active GEF domain, allowing Epac to activate small Ras-like GTPase proteins, such as <a href="/wiki/Rap1" title="Rap1">Rap1</a>. </p> <div class="mw-heading mw-heading4"><h4 id="Additional_role_of_secreted_cAMP_in_social_amoebae">Additional role of secreted cAMP in social amoebae</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyclic_adenosine_monophosphate&action=edit&section=5" title="Edit section: Additional role of secreted cAMP in social amoebae"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Fungal_behavior" title="Fungal behavior">Fungal behavior</a></div> <p>In the species <i><a href="/wiki/Dictyostelid" title="Dictyostelid">Dictyostelium discoideum</a></i>, cAMP acts outside the cell as a secreted signal. The <a href="/wiki/Chemotaxis" title="Chemotaxis">chemotactic</a> aggregation of cells is organized by periodic waves of cAMP that propagate between cells over distances as large as several centimetres. The waves are the result of a regulated production and secretion of extracellular cAMP and a spontaneous biological oscillator that initiates the waves at centers of territories.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Role_in_bacteria">Role in bacteria</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyclic_adenosine_monophosphate&action=edit&section=6" title="Edit section: Role in bacteria"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In <a href="/wiki/Bacteria" title="Bacteria">bacteria</a>, the level of cAMP varies depending on the medium used for growth. In particular, cAMP is low when glucose is the carbon source. This occurs through inhibition of the cAMP-producing enzyme, <a href="/wiki/Adenylate_cyclase" class="mw-redirect" title="Adenylate cyclase">adenylate cyclase</a>, as a side-effect of glucose transport into the cell. The transcription factor <a href="/wiki/CAMP_receptor_protein" title="CAMP receptor protein">cAMP receptor protein</a> (CRP) also called <a href="/wiki/Catabolite_activator_protein" title="Catabolite activator protein">CAP (catabolite gene activator protein)</a> forms a complex with cAMP and thereby is activated to bind to DNA. CRP-cAMP increases expression of a large number of genes, including some encoding <a href="/wiki/Enzyme" title="Enzyme">enzymes</a> that can supply energy independent of glucose. </p><p>cAMP, for example, is involved in the positive regulation of the <a href="/wiki/Lac_operon" title="Lac operon">lac operon</a>. In an environment with a low glucose concentration, cAMP accumulates and binds to the allosteric site on CRP (<a href="/wiki/CAMP_receptor_protein" title="CAMP receptor protein">cAMP receptor protein</a>), a transcription activator protein. The protein assumes its active shape and binds to a specific site upstream of the lac promoter, making it easier for RNA polymerase to bind to the adjacent promoter to start transcription of the lac operon, increasing the rate of lac operon transcription. With a high glucose concentration, the cAMP concentration decreases, and the CRP disengages from the lac operon. </p> <div class="mw-heading mw-heading2"><h2 id="Pathology">Pathology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyclic_adenosine_monophosphate&action=edit&section=7" title="Edit section: Pathology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Since cyclic AMP is a second messenger and plays vital role in cell signalling, it has been implicated in various disorders but not restricted to the roles given below: </p> <div class="mw-heading mw-heading3"><h3 id="Role_in_human_carcinoma">Role in human carcinoma</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyclic_adenosine_monophosphate&action=edit&section=8" title="Edit section: Role in human carcinoma"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Some research has suggested that a deregulation of cAMP pathways and an aberrant activation of cAMP-controlled genes is linked to the growth of some cancers.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><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><sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Role_in_prefrontal_cortex_disorders">Role in prefrontal cortex disorders</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyclic_adenosine_monophosphate&action=edit&section=9" title="Edit section: Role in prefrontal cortex disorders"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Recent research suggests that cAMP affects the function of higher-order thinking in the <a href="/wiki/Prefrontal_cortex" title="Prefrontal cortex">prefrontal cortex</a> through its regulation of ion channels called <a href="/wiki/Hyperpolarization-activated_cyclic_nucleotide-gated_channels" class="mw-redirect" title="Hyperpolarization-activated cyclic nucleotide-gated channels">hyperpolarization-activated cyclic nucleotide-gated channels</a> (HCN). When cAMP stimulates the HCN, the channels open, This research, especially the cognitive deficits in age-related illnesses and ADHD, is of interest to researchers studying the brain.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>cAMP is involved in activation of trigeminocervical system leading to neurogenic inflammation and causing migraine. <sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Role_in_infectious_disease_agents'_pathogenesis"><span id="Role_in_infectious_disease_agents.27_pathogenesis"></span>Role in infectious disease agents' pathogenesis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyclic_adenosine_monophosphate&action=edit&section=10" title="Edit section: Role in infectious disease agents' pathogenesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Disrupted functioning of cAMP has been noted as one of the mechanisms of several bacterial exotoxins. </p><p>They can be subgrouped into two distinct categories:<sup id="cite_ref-klin-wochenschr_11-0" class="reference"><a href="#cite_note-klin-wochenschr-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p> <ul><li>Toxins that interfere with enzymes <a href="/wiki/ADP-ribosylation" title="ADP-ribosylation">ADP-ribosyl-transferases</a>, and</li> <li><a href="/wiki/Adenylate_cyclase_toxin" title="Adenylate cyclase toxin">invasive adenylate cyclases</a>.</li></ul> <div class="mw-heading mw-heading4"><h4 id="ADP-ribosyl-transferases_related_toxins">ADP-ribosyl-transferases related toxins</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyclic_adenosine_monophosphate&action=edit&section=11" title="Edit section: ADP-ribosyl-transferases related toxins"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Cholera_toxin" title="Cholera toxin">Cholera toxin</a></div> <ul><li><a href="/wiki/Cholera_toxin" title="Cholera toxin">Cholera toxin</a> is an <a href="/wiki/AB_toxin" title="AB toxin">AB toxin</a> that has five B subunints and one A subunit. The toxin acts by the following mechanism: First, the B subunit ring of the cholera toxin binds to <a href="/wiki/GM1" title="GM1">GM1</a> <a href="/wiki/Ganglioside" title="Ganglioside">gangliosides</a> on the surface of target cells. If a cell lacks GM1 the toxin most likely binds to other types of glycans, such as Lewis Y and Lewis X, attached to proteins instead of lipids.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-klin-wochenschr_11-1" class="reference"><a href="#cite_note-klin-wochenschr-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup></li></ul> <div class="mw-heading mw-heading2"><h2 id="Uses">Uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyclic_adenosine_monophosphate&action=edit&section=12" title="Edit section: Uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Forskolin" title="Forskolin">Forskolin</a> is commonly used as a tool in biochemistry to raise levels of cAMP in the study and research of <a href="/wiki/Cell_(biology)" title="Cell (biology)">cell</a> physiology.<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyclic_adenosine_monophosphate&action=edit&section=13" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Cyclic_guanosine_monophosphate" title="Cyclic guanosine monophosphate">Cyclic guanosine monophosphate</a> (cGMP)</li> <li><a href="/wiki/8-Bromoadenosine_3%27,5%27-cyclic_monophosphate" title="8-Bromoadenosine 3',5'-cyclic monophosphate">8-Bromoadenosine 3',5'-cyclic monophosphate</a> (8-Br-cAMP)</li> <li><a href="/wiki/Acrasin" title="Acrasin">Acrasin</a> specific to chemotactic use in <i>Dictyostelium discoideum</i>.</li> <li><a href="/wiki/Phosphodiesterase_4" title="Phosphodiesterase 4">phosphodiesterase 4</a> (PDE 4) which degrades cAMP</li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyclic_adenosine_monophosphate&action=edit&section=14" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-1990-Hanukoglu-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1990-Hanukoglu_1-0">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output 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.navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Intracellular_signaling_peptides_and_proteins" title="Template:Intracellular signaling peptides and proteins"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Intracellular_signaling_peptides_and_proteins" title="Template talk:Intracellular signaling peptides and proteins"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Intracellular_signaling_peptides_and_proteins" title="Special:EditPage/Template:Intracellular signaling peptides and proteins"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Intracellular_signaling_peptides_and_proteins" style="font-size:114%;margin:0 4em"><a href="/wiki/Intracellular_signaling_peptides_and_proteins" class="mw-redirect" title="Intracellular signaling peptides and proteins">Intracellular signaling peptides and proteins</a></div></th></tr><tr><th scope="row" class="navbox-group" style="background-color: AntiqueWhite;width:1%">MAP</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>see <a href="/wiki/Template:MAP_kinase_pathway" title="Template:MAP kinase pathway">MAP kinase pathway</a></i></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="background-color: AntiqueWhite;width:1%">Calcium</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Intracellular_calcium-sensing_proteins" title="Intracellular calcium-sensing proteins">Intracellular calcium-sensing proteins</a></li> <li><a href="/wiki/Calcineurin" title="Calcineurin">Calcineurin</a></li> <li><a href="/wiki/Ca2%2B/calmodulin-dependent_protein_kinase" class="mw-redirect" title="Ca2+/calmodulin-dependent protein kinase">Ca2+/calmodulin-dependent protein kinase</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="background-color: AntiqueWhite;width:1%"><a href="/wiki/G_protein" title="G protein">G protein</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;background-color: AntiqueWhite"><a href="/wiki/Heterotrimeric_G_protein" title="Heterotrimeric G protein">Heterotrimeric</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%;background-color: AntiqueWhite"><a href="/wiki/CAMP-dependent_pathway" title="CAMP-dependent pathway">cAMP</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/Heterotrimeric_G_protein" title="Heterotrimeric G protein">Heterotrimeric G protein</a> <ul><li><a href="/wiki/Gs_alpha_subunit" title="Gs alpha subunit">Gs</a>/<a href="/wiki/Gi_alpha_subunit" title="Gi alpha subunit">Gi</a></li></ul></li> <li><a href="/wiki/Adenylate_cyclase" class="mw-redirect" title="Adenylate cyclase">Adenylate cyclase</a></li> <li><a class="mw-selflink selflink">cAMP</a></li> <li><a href="/wiki/3%27,5%27-cyclic-AMP_phosphodiesterase" title="3',5'-cyclic-AMP phosphodiesterase">3',5'-cyclic-AMP phosphodiesterase</a></li> <li><a href="/wiki/Protein_kinase_A" title="Protein kinase A">Protein kinase A</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background-color: AntiqueWhite"><a href="/wiki/Cyclic_guanosine_monophosphate" title="Cyclic guanosine monophosphate">cGMP</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/Transducin" title="Transducin">Transducin</a></li> <li><a href="/wiki/Gustducin" title="Gustducin">Gustducin</a></li> <li><a href="/wiki/Guanylate_cyclase" title="Guanylate cyclase">Guanylate cyclase</a></li> <li><a href="/wiki/Cyclic_guanosine_monophosphate" title="Cyclic guanosine monophosphate">cGMP</a></li> <li><a href="/wiki/3%27,5%27-cyclic-GMP_phosphodiesterase" title="3',5'-cyclic-GMP phosphodiesterase">3',5'-cyclic-GMP phosphodiesterase</a></li> <li><a href="/wiki/CGMP-dependent_protein_kinase" title="CGMP-dependent protein kinase">Protein kinase G</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/G_alpha_subunit" title="G alpha subunit">G alpha subunit</a> G<sub>α</sub> <ul><li><a href="/wiki/GNAO1" title="GNAO1">GNAO1</a></li> <li><a href="/wiki/GNAI1" title="GNAI1">GNAI1</a></li> <li><a href="/wiki/GNAI2" title="GNAI2">GNAI2</a></li> <li><a href="/wiki/GNAI3" title="GNAI3">GNAI3</a></li> <li><a href="/wiki/GNAT1" title="GNAT1">GNAT1</a></li> <li><a href="/wiki/GNAT2" title="GNAT2">GNAT2</a></li> <li><a href="/wiki/GNAT3" title="GNAT3">GNAT3</a></li> <li><a href="/wiki/GNAZ" title="GNAZ">GNAZ</a></li> <li><a href="/wiki/GNAS_complex_locus" title="GNAS complex locus">GNAS</a></li> <li><a href="/wiki/GNAL" title="GNAL">GNAL</a></li> <li><a href="/wiki/GNAQ" title="GNAQ">GNAQ</a></li> <li><a href="/wiki/GNA11" title="GNA11">GNA11</a></li> <li><a href="/wiki/GNA12" title="GNA12">GNA12</a></li> <li><a href="/wiki/GNA13" title="GNA13">GNA13</a></li> <li><a href="/wiki/GNA14" title="GNA14">GNA14</a></li> <li><a href="/w/index.php?title=GNA15/GNA16&action=edit&redlink=1" class="new" title="GNA15/GNA16 (page does not exist)">GNA15/GNA16</a></li></ul></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/G_beta-gamma_complex" title="G beta-gamma complex">G beta-gamma complex</a> G<sub>β</sub> <ul><li><a href="/wiki/GNB1" title="GNB1">GNB1</a></li> <li><a href="/wiki/GNB2" title="GNB2">GNB2</a></li> <li><a href="/wiki/GNB3" title="GNB3">GNB3</a></li> <li><a href="/wiki/GNB4" title="GNB4">GNB4</a></li> <li><a href="/wiki/GNB5" title="GNB5">GNB5</a></li></ul></li> <li>G<sub>γ</sub> <ul><li><a href="/wiki/GNGT1" title="GNGT1">GNGT1</a></li> <li><a href="/wiki/GNGT2" title="GNGT2">GNGT2</a></li> <li><a href="/wiki/GNG2" title="GNG2">GNG2</a></li> <li><a href="/wiki/GNG3" title="GNG3">GNG3</a></li> <li><a href="/wiki/GNG4" title="GNG4">GNG4</a></li> <li><a href="/wiki/GNG5" title="GNG5">GNG5</a></li> <li><a href="/wiki/GNG7" title="GNG7">GNG7</a></li> <li><a href="/w/index.php?title=GNG8&action=edit&redlink=1" class="new" title="GNG8 (page does not exist)">GNG8</a></li> <li><a href="/w/index.php?title=GNG10&action=edit&redlink=1" class="new" title="GNG10 (page does not exist)">GNG10</a></li> <li><a href="/wiki/GNG11" title="GNG11">GNG11</a></li> <li><a href="/wiki/GNG12" title="GNG12">GNG12</a></li> <li><a href="/wiki/GNG13" title="GNG13">GNG13</a></li> <li><a href="/wiki/BSCL2" title="BSCL2">BSCL2</a></li></ul></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/G_protein-coupled_receptor_kinase" title="G protein-coupled receptor kinase">G protein-coupled receptor kinase</a></li> <li><a href="/wiki/AMP-activated_protein_kinase" title="AMP-activated protein kinase">AMP-activated protein kinase</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background-color: AntiqueWhite"><a href="/wiki/Small_GTPase" title="Small GTPase">Monomeric</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/ADP_ribosylation_factor" title="ADP ribosylation factor">ARFs</a></li> <li><a href="/wiki/Rab_(G-protein)" title="Rab (G-protein)">Rabs</a></li> <li><a href="/wiki/Ras_subfamily" class="mw-redirect" title="Ras subfamily">Ras</a> <ul><li><a href="/wiki/HRAS" title="HRAS">HRAS</a></li> <li><a href="/wiki/KRAS" title="KRAS">KRAS</a></li> <li><a href="/wiki/Neuroblastoma_RAS_viral_oncogene_homolog" title="Neuroblastoma RAS viral oncogene homolog">NRAS</a></li></ul></li> <li><a href="/wiki/Rho_family_of_GTPases" title="Rho family of GTPases">Rhos</a></li> <li><a href="/wiki/ADP_ribosylation_factor" title="ADP ribosylation factor">Arfs</a></li> <li><a href="/wiki/Ran_(gene)" class="mw-redirect" title="Ran (gene)">Ran</a></li> <li><a href="/wiki/RHEB" title="RHEB">Rhebs</a></li> <li><a href="/wiki/Rap_GTP-binding_protein" title="Rap GTP-binding protein">Raps</a></li> <li><a href="/wiki/RRAD_(gene)" title="RRAD (gene)">RGKs</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="background-color: AntiqueWhite;width:1%">Cyclin</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cyclin-dependent_kinase_inhibitor_protein" title="Cyclin-dependent kinase inhibitor protein">Cyclin-dependent kinase inhibitor protein</a></li> <li><a href="/wiki/Cyclin-dependent_kinase" title="Cyclin-dependent kinase">Cyclin-dependent kinase</a></li> <li><a href="/wiki/Cyclin" title="Cyclin">Cyclin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="background-color: AntiqueWhite;width:1%">Lipid</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Phosphoinositide_phospholipase_C" title="Phosphoinositide phospholipase C">Phosphoinositide phospholipase C</a></li> <li><a href="/wiki/Phospholipase_C" title="Phospholipase C">Phospholipase C</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="background-color: AntiqueWhite;width:1%">Other <a href="/wiki/Protein_kinase" title="Protein kinase">protein kinase</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;background-color: AntiqueWhite"><a href="/wiki/Serine/threonine-specific_protein_kinase" title="Serine/threonine-specific protein kinase">Serine/threonine</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/Casein_kinase" title="Casein kinase">Casein kinase</a> <ul><li><a href="/wiki/Casein_kinase_1" title="Casein kinase 1">1</a></li> <li><a href="/wiki/Casein_kinase_2" title="Casein kinase 2">2</a></li></ul></li> <li><a href="/wiki/EIF-2_kinase" title="EIF-2 kinase">eIF-2 kinase</a> <ul><li><a href="/wiki/EIF2AK3" title="EIF2AK3">EIF2AK3</a></li></ul></li> <li><a href="/wiki/Glycogen_synthase_kinase" class="mw-redirect" title="Glycogen synthase kinase">Glycogen synthase kinase</a> <ul><li><a href="/w/index.php?title=GSK1&action=edit&redlink=1" class="new" title="GSK1 (page does not exist)">GSK1</a></li> <li><a href="/w/index.php?title=GSK2&action=edit&redlink=1" class="new" title="GSK2 (page does not exist)">GSK2</a></li> <li><a href="/wiki/GSK-3" title="GSK-3">GSK-3</a></li> <li><a href="/wiki/GSK3A" title="GSK3A">GSK3A</a></li> <li><a href="/wiki/GSK3B" class="mw-redirect" title="GSK3B">GSK3B</a></li></ul></li> <li><a href="/wiki/I%CE%BAB_kinase" title="IκB kinase">IκB kinase</a> <ul><li><a href="/wiki/CHUK" title="CHUK">CHUK</a></li> <li><a href="/wiki/IKK2" title="IKK2">IKK2</a></li> <li><a href="/wiki/IKBKG" title="IKBKG">IKBKG</a></li></ul></li> <li><a href="/wiki/Interleukin-1_receptor_associated_kinase" title="Interleukin-1 receptor associated kinase">Interleukin-1 receptor associated kinase</a> <ul><li><a href="/wiki/IRAK1" title="IRAK1">IRAK1</a></li> <li><a href="/wiki/IRAK2" title="IRAK2">IRAK2</a></li> <li><a href="/wiki/IRAK3" title="IRAK3">IRAK3</a></li> <li><a href="/wiki/IRAK4" title="IRAK4">IRAK4</a></li></ul></li> <li><a href="/wiki/Lim_kinase" title="Lim kinase">Lim kinase</a> <ul><li><a href="/wiki/LIMK1" title="LIMK1">LIMK1</a></li> <li><a href="/wiki/LIMK2" title="LIMK2">LIMK2</a></li></ul></li> <li><a href="/wiki/P21-activated_kinases" title="P21-activated kinases">p21-activated kinases</a> <ul><li><a href="/wiki/PAK1" title="PAK1">PAK1</a></li> <li><a href="/wiki/PAK2" title="PAK2">PAK2</a></li> <li><a href="/wiki/PAK3" title="PAK3">PAK3</a></li> <li><a href="/wiki/PAK4" title="PAK4">PAK4</a></li></ul></li> <li><a href="/wiki/Rho-associated_protein_kinase" title="Rho-associated protein kinase">Rho-associated protein kinase</a> <ul><li><a href="/wiki/ROCK1" title="ROCK1">ROCK1</a></li> <li><a href="/wiki/ROCK2" title="ROCK2">ROCK2</a></li></ul></li> <li><a href="/wiki/Ribosomal_s6_kinase" title="Ribosomal s6 kinase">Ribosomal s6 kinase</a> <ul><li><a href="/wiki/RPS6KA1" title="RPS6KA1">RPS6KA1</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background-color: AntiqueWhite"><a href="/wiki/Non-receptor_tyrosine_kinase" title="Non-receptor tyrosine kinase">Tyrosine</a>:</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/ZAP70" title="ZAP70">ZAP70</a></li> <li><a href="/w/index.php?title=Focal_adhesion_protein-tyrosine_kinase&action=edit&redlink=1" class="new" title="Focal adhesion protein-tyrosine kinase (page does not exist)">Focal adhesion protein-tyrosine kinase</a> <ul><li><a href="/wiki/PTK2" title="PTK2">PTK2</a></li> <li><a href="/wiki/PTK2B" title="PTK2B">PTK2B</a></li></ul></li> <li><a href="/wiki/Bruton%27s_tyrosine_kinase" title="Bruton's tyrosine kinase">BTK</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background-color: AntiqueWhite">Serine/threonine/tyrosine</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/Dual-specificity_kinase" title="Dual-specificity kinase">Dual-specificity kinase</a> <ul><li><a href="/wiki/DYRK1A" title="DYRK1A">DYRK1A</a></li> <li><a href="/wiki/DYRK1B" title="DYRK1B">DYRK1B</a></li> <li><a href="/wiki/DYRK2" title="DYRK2">DYRK2</a></li> <li><a href="/wiki/DYRK3" title="DYRK3">DYRK3</a></li> <li><a href="/w/index.php?title=DYRK4&action=edit&redlink=1" class="new" title="DYRK4 (page does not exist)">DYRK4</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background-color: AntiqueWhite">Arginine</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/Arginine_kinase" title="Arginine kinase">Arginine kinase</a></li> <li><a href="/w/index.php?title=McsB&action=edit&redlink=1" class="new" title="McsB (page does not exist)">McsB</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="background-color: AntiqueWhite;width:1%">Other <a href="/wiki/Protein_phosphatase" title="Protein phosphatase">protein phosphatase</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;background-color: AntiqueWhite"><a href="/wiki/Protein_serine/threonine_phosphatase" title="Protein serine/threonine phosphatase">Serine/threonine</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/Protein_phosphatase_2" title="Protein phosphatase 2">Protein phosphatase 2</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background-color: AntiqueWhite"><a href="/wiki/Protein_tyrosine_phosphatase" title="Protein tyrosine phosphatase">Tyrosine</a>:</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Protein_tyrosine_phosphatase" title="Protein tyrosine phosphatase">protein tyrosine phosphatase</a>: <a href="/w/index.php?title=Receptor-like_protein_tyrosine_phosphatase&action=edit&redlink=1" class="new" title="Receptor-like protein tyrosine phosphatase (page does not exist)">Receptor-like protein tyrosine phosphatase</a></li> <li><a href="/wiki/Sh2_domain-containing_protein_tyrosine_phosphatase" class="mw-redirect" title="Sh2 domain-containing protein tyrosine phosphatase">Sh2 domain-containing protein tyrosine phosphatase</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background-color: AntiqueWhite">both:</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/Dual-specificity_phosphatase" title="Dual-specificity phosphatase">Dual-specificity phosphatase</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="background-color: AntiqueWhite;width:1%"><a href="/wiki/Apoptosis" title="Apoptosis">Apoptosis</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>see <a href="/wiki/Template:Apoptosis_signaling_pathway" title="Template:Apoptosis signaling pathway">apoptosis signaling pathway</a></i></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="background-color: AntiqueWhite;width:1%"><a href="/wiki/GTP-binding_protein_regulators" title="GTP-binding protein regulators">GTP-binding protein regulators</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>see <a href="/wiki/Template:GTP-binding_protein_regulators" title="Template:GTP-binding protein regulators">GTP-binding protein regulators</a></i></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="background-color: AntiqueWhite;width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/ATF6" title="ATF6">Activating transcription factor 6</a></li> <li><a href="/wiki/Signal_transducing_adaptor_protein" title="Signal transducing adaptor protein">Signal transducing adaptor protein</a></li> <li><a href="/wiki/I%CE%BAB%CE%B1" title="IκBα">I-kappa B protein</a></li> <li><a href="/wiki/MUC4" class="mw-redirect" title="MUC4">Mucin-4</a></li> <li><a href="/wiki/Olfactory_marker_protein" title="Olfactory marker protein">Olfactory marker protein</a></li> <li><a href="/wiki/Phosphatidylethanolamine_binding_protein" class="mw-redirect" title="Phosphatidylethanolamine binding protein">Phosphatidylethanolamine binding protein</a></li> <li><a href="/wiki/EDARADD" title="EDARADD">EDARADD</a></li> <li><a href="/wiki/PRKCSH" title="PRKCSH">PRKCSH</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="background-color: AntiqueWhite"><div><i>see also <a href="/wiki/Template:Deficiencies_of_intracellular_signaling_peptides_and_proteins" title="Template:Deficiencies of intracellular signaling peptides and proteins">deficiencies of intracellular signaling peptides and proteins</a></i></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Nucleic_acid_constituents" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Nucleobases,_nucleosides,_and_nucleotides" title="Template:Nucleobases, nucleosides, and nucleotides"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Nucleobases,_nucleosides,_and_nucleotides" title="Template talk:Nucleobases, nucleosides, and nucleotides"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Nucleobases,_nucleosides,_and_nucleotides" title="Special:EditPage/Template:Nucleobases, nucleosides, and nucleotides"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Nucleic_acid_constituents" style="font-size:114%;margin:0 4em"><a href="/wiki/Nucleic_acid" title="Nucleic acid">Nucleic acid</a> constituents</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nucleobase" class="mw-redirect" title="Nucleobase">Nucleobase</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Purine" title="Purine">Purine</a> <ul><li><a href="/wiki/Adenine" title="Adenine">Adenine</a></li> <li><a href="/wiki/Guanine" title="Guanine">Guanine</a></li> <li><a href="/wiki/Hypoxanthine" title="Hypoxanthine">Hypoxanthine</a></li> <li><a href="/wiki/Xanthine" title="Xanthine">Xanthine</a></li> <li><a href="/wiki/Purine_analogue" title="Purine analogue">Purine analogue</a></li></ul></li> <li><a href="/wiki/Pyrimidine" title="Pyrimidine">Pyrimidine</a> <ul><li><a href="/wiki/Uracil" title="Uracil">Uracil</a></li> <li><a href="/wiki/Thymine" title="Thymine">Thymine</a></li> <li><a href="/wiki/Cytosine" title="Cytosine">Cytosine</a></li> <li><a href="/wiki/Pyrimidine_analogue" title="Pyrimidine analogue">Pyrimidine analogue</a></li></ul></li> <li><a href="/wiki/Base_pair#Unnatural_base_pair_(UBP)" title="Base pair">Unnatural base pair (UBP)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nucleoside" title="Nucleoside">Nucleoside</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Ribonucleoside" title="Ribonucleoside">Ribonucleoside</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/Adenosine" title="Adenosine">Adenosine</a></li> <li><a href="/wiki/Guanosine" title="Guanosine">Guanosine</a></li> <li><a href="/wiki/5-Methyluridine" title="5-Methyluridine">5-Methyluridine</a></li> <li><a href="/wiki/Uridine" title="Uridine">Uridine</a></li> <li><a href="/wiki/5-Methylcytidine" title="5-Methylcytidine">5-Methylcytidine</a></li> <li><a href="/wiki/Cytidine" title="Cytidine">Cytidine</a></li> <li><a href="/wiki/Pseudouridine" title="Pseudouridine">Pseudouridine</a></li> <li><a href="/wiki/Inosine" title="Inosine">Inosine</a></li> <li><a href="/wiki/N6-Methyladenosine" title="N6-Methyladenosine"><i>N</i><sup>6</sup>-Methyladenosine</a></li> <li><a href="/wiki/Xanthosine" title="Xanthosine">Xanthosine</a></li> <li><a href="/wiki/Wybutosine" title="Wybutosine">Wybutosine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Deoxyribonucleoside" class="mw-redirect" title="Deoxyribonucleoside">Deoxyribonucleoside</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/Deoxyadenosine" title="Deoxyadenosine">Deoxyadenosine</a></li> <li><a href="/wiki/Deoxyguanosine" title="Deoxyguanosine">Deoxyguanosine</a></li> <li><a href="/wiki/Thymidine" title="Thymidine">Thymidine</a></li> <li><a href="/wiki/Deoxyuridine" title="Deoxyuridine">Deoxyuridine</a></li> <li><a href="/wiki/Deoxycytidine" title="Deoxycytidine">Deoxycytidine</a></li> <li><a href="/w/index.php?title=Deoxyinosine&action=edit&redlink=1" class="new" title="Deoxyinosine (page does not exist)">Deoxyinosine</a></li> <li><a href="/w/index.php?title=Deoxyxanthosine&action=edit&redlink=1" class="new" title="Deoxyxanthosine (page does not exist)">Deoxyxanthosine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nucleotide" title="Nucleotide">Nucleotide</a><br />(Nucleoside monophosphate)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Ribonucleotide" title="Ribonucleotide">Ribonucleotide</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/Adenosine_monophosphate" title="Adenosine monophosphate">AMP</a></li> <li><a href="/wiki/Guanosine_monophosphate" title="Guanosine monophosphate">GMP</a></li> <li><a href="/w/index.php?title=5-Methyluridine_monophosphate&action=edit&redlink=1" class="new" title="5-Methyluridine monophosphate (page does not exist)">m<sup>5</sup>UMP</a></li> <li><a href="/wiki/Uridine_monophosphate" title="Uridine monophosphate">UMP</a></li> <li><a href="/wiki/Cytidine_monophosphate" title="Cytidine monophosphate">CMP</a></li> <li><a href="/wiki/Inosinic_acid" title="Inosinic acid">IMP</a></li> <li><a href="/wiki/Xanthosine_monophosphate" title="Xanthosine monophosphate">XMP</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Deoxyribonucleotide" title="Deoxyribonucleotide">Deoxyribonucleotide</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/Deoxyadenosine_monophosphate" title="Deoxyadenosine monophosphate">dAMP</a></li> <li><a href="/wiki/Deoxyguanosine_monophosphate" title="Deoxyguanosine monophosphate">dGMP</a></li> <li><a href="/wiki/Thymidine_monophosphate" title="Thymidine monophosphate">dTMP</a></li> <li><a href="/wiki/Deoxyuridine_monophosphate" title="Deoxyuridine monophosphate">dUMP</a></li> <li><a href="/wiki/Deoxycytidine_monophosphate" title="Deoxycytidine monophosphate">dCMP</a></li> <li><a href="/wiki/Deoxyinosine_monophosphate" title="Deoxyinosine monophosphate">dIMP</a></li> <li><a href="/w/index.php?title=Deoxyxanthosine_monophosphate&action=edit&redlink=1" class="new" title="Deoxyxanthosine monophosphate (page does not exist)">dXMP</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cyclic_nucleotide" title="Cyclic nucleotide">Cyclic nucleotide</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 class="mw-selflink selflink">cAMP</a></li> <li><a href="/wiki/Cyclic_guanosine_monophosphate" title="Cyclic guanosine monophosphate">cGMP</a></li> <li><a href="/wiki/Cyclic_di-GMP" title="Cyclic di-GMP">c-di-GMP</a></li> <li><a href="/wiki/Cyclic_di-AMP" title="Cyclic di-AMP">c-di-AMP</a></li> <li><a href="/wiki/Cyclic_ADP-ribose" title="Cyclic ADP-ribose">cADPR</a></li> <li><a href="/wiki/Cyclic_guanosine_monophosphate%E2%80%93adenosine_monophosphate" title="Cyclic guanosine monophosphate–adenosine monophosphate">cGAMP</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Nucleoside diphosphate</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Adenosine_diphosphate" title="Adenosine diphosphate">ADP</a></li> <li><a href="/wiki/Guanosine_diphosphate" title="Guanosine diphosphate">GDP</a></li> <li><a href="/w/index.php?title=5-Methyluridine_diphosphate&action=edit&redlink=1" class="new" title="5-Methyluridine diphosphate (page does not exist)">m<sup>5</sup>UDP</a></li> <li><a href="/wiki/Uridine_diphosphate" title="Uridine diphosphate">UDP</a></li> <li><a href="/wiki/Cytidine_diphosphate" title="Cytidine diphosphate">CDP</a></li> <li><a href="/w/index.php?title=Xanthosine_diphosphate&action=edit&redlink=1" class="new" title="Xanthosine diphosphate (page does not exist)">Xanthosine diphosphate</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Deoxyadenosine_diphosphate" title="Deoxyadenosine diphosphate">dADP</a></li> <li><a href="/wiki/Deoxyguanosine_diphosphate" title="Deoxyguanosine diphosphate">dGDP</a></li> <li><a href="/wiki/Thymidine_diphosphate" title="Thymidine diphosphate">dTDP</a></li> <li><a href="/w/index.php?title=Deoxyuridine_diphosphate&action=edit&redlink=1" class="new" title="Deoxyuridine diphosphate (page does not exist)">dUDP</a></li> <li><a href="/wiki/Deoxycytidine_diphosphate" title="Deoxycytidine diphosphate">dCDP</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nucleoside_triphosphate" title="Nucleoside triphosphate">Nucleoside triphosphate</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a></li> <li><a href="/wiki/Guanosine_triphosphate" title="Guanosine triphosphate">GTP</a></li> <li><a href="/wiki/5-Methyluridine_triphosphate" title="5-Methyluridine triphosphate">m<sup>5</sup>UTP</a></li> <li><a href="/wiki/Uridine_triphosphate" title="Uridine triphosphate">UTP</a></li> <li><a href="/wiki/Cytidine_triphosphate" title="Cytidine triphosphate">CTP</a></li> <li><a href="/wiki/Inosine_triphosphate" title="Inosine triphosphate">ITP</a></li> <li><a href="/wiki/Xanthosine_triphosphate" title="Xanthosine triphosphate">XTP</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Deoxyadenosine_triphosphate" title="Deoxyadenosine triphosphate">dATP</a></li> <li><a href="/wiki/Deoxyguanosine_triphosphate" title="Deoxyguanosine triphosphate">dGTP</a></li> <li><a href="/wiki/Thymidine_triphosphate" title="Thymidine triphosphate">dTTP</a></li> <li><a href="/w/index.php?title=Deoxyuridine_triphosphate&action=edit&redlink=1" class="new" title="Deoxyuridine triphosphate (page does not exist)">dUTP</a></li> <li><a href="/wiki/Deoxycytidine_triphosphate" title="Deoxycytidine triphosphate">dCTP</a></li> <li><a href="/w/index.php?title=Deoxyinosine_triphosphate&action=edit&redlink=1" class="new" title="Deoxyinosine triphosphate (page does not exist)">dITP</a></li> <li><a href="/w/index.php?title=Deoxyxanthosine_triphosphate&action=edit&redlink=1" class="new" title="Deoxyxanthosine triphosphate (page does not exist)">dXTP</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table></div> <!-- NewPP limit report Parsed by mw‐api‐ext.codfw.main‐744c7589dd‐w6fsk Cached time: 20241125102801 Cache expiry: 2592000 Reduced expiry: false Complications: [vary‐revision‐sha1, show‐toc] CPU time usage: 0.632 seconds Real time usage: 0.795 seconds Preprocessor visited node 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