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</a> <ul id="toc-Salvage_pathways-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Functions" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Functions"> <div class="vector-toc-text"> 4 Functions </div> </a> <button aria-controls="toc-Functions-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Functions subsection </button> <ul id="toc-Functions-sublist" class="vector-toc-list"> <li id="toc-Oxidoreductase_binding_of_NAD" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Oxidoreductase_binding_of_NAD"> <div class="vector-toc-text"> 4.1 Oxidoreductase binding of NAD </div> </a> <ul id="toc-Oxidoreductase_binding_of_NAD-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Role_in_redox_metabolism" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Role_in_redox_metabolism"> <div class="vector-toc-text"> 4.2 Role in redox metabolism </div> </a> <ul id="toc-Role_in_redox_metabolism-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Non-redox_roles" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Non-redox_roles"> <div class="vector-toc-text"> 4.3 Non-redox roles </div> </a> <ul id="toc-Non-redox_roles-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Extracellular_actions_of_NAD+" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Extracellular_actions_of_NAD+"> <div class="vector-toc-text"> 4.4 Extracellular actions of NAD+ </div> </a> <ul id="toc-Extracellular_actions_of_NAD+-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Clinical_significance" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Clinical_significance"> <div class="vector-toc-text"> 5 Clinical significance </div> </a> <ul id="toc-Clinical_significance-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-History" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#History"> <div class="vector-toc-text"> 6 History </div> </a> <ul id="toc-History-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"> 7 See also </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"> 8 References </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Further_reading" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Further_reading"> <div class="vector-toc-text"> 9 Further reading </div> </a> <button aria-controls="toc-Further_reading-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Further reading subsection </button> <ul id="toc-Further_reading-sublist" class="vector-toc-list"> <li id="toc-Function" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Function"> <div class="vector-toc-text"> 9.1 Function </div> </a> <ul id="toc-Function-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-History_2" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#History_2"> <div class="vector-toc-text"> 9.2 History </div> </a> <ul id="toc-History_2-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> 10 External links </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" > Toggle the table of contents </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">Nicotinamide adenine dinucleotide</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 47 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-47" aria-hidden="true" > 47 languages </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%AB%D9%86%D8%A7%D8%A6%D9%8A_%D9%86%D9%88%D9%83%D9%84%D9%8A%D9%88%D8%AA%D9%8A%D8%AF_%D8%A7%D9%84%D8%A3%D8%AF%D9%86%D9%8A%D9%86_%D9%88%D8%A3%D9%85%D9%8A%D8%AF_%D8%A7%D9%84%D9%86%D9%8A%D9%83%D9%88%D8%AA%D9%8A%D9%86" title="ثنائي نوكليوتيد الأدنين وأميد النيكوتين – Arabic" lang="ar" hreflang="ar" data-title="ثنائي نوكليوتيد الأدنين وأميد النيكوتين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target">العربية</a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D9%86%DB%8C%DA%A9%D9%88%D8%AA%DB%8C%D9%86%E2%80%8C%D8%A2%D9%85%DB%8C%D8%AF_%D8%A2%D8%AF%D9%86%DB%8C%D9%86_%D8%AF%DB%8C%E2%80%8C%D9%86%D9%88%DA%A9%D9%84%D8%A6%D9%88%D8%AA%DB%8C%D8%AF" title="نیکوتین‌آمید آدنین دی‌نوکلئوتید – South Azerbaijani" lang="azb" hreflang="azb" data-title="نیکوتین‌آمید آدنین دی‌نوکلئوتید" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target">تۆرکجه</a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%9D%D0%90%D0%94" title="НАД – Bulgarian" lang="bg" hreflang="bg" data-title="НАД" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target">Български</a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Nikotinamid_adenin_dinukleotid" title="Nikotinamid adenin dinukleotid – Bosnian" lang="bs" hreflang="bs" data-title="Nikotinamid adenin dinukleotid" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target">Bosanski</a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Dinucle%C3%B2tid_de_nicotinamida_i_adenina" title="Dinucleòtid de nicotinamida i adenina – Catalan" lang="ca" hreflang="ca" data-title="Dinucleòtid de nicotinamida i adenina" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target">Català</a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Nikotinamidadenindinukleotid" title="Nikotinamidadenindinukleotid – Czech" lang="cs" hreflang="cs" data-title="Nikotinamidadenindinukleotid" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target">Čeština</a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Deuniwcleotid_Adenin_Nicotinamid_(NAD)" title="Deuniwcleotid Adenin Nicotinamid (NAD) – Welsh" lang="cy" hreflang="cy" data-title="Deuniwcleotid Adenin Nicotinamid (NAD)" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target">Cymraeg</a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Nikotinamidadenindinukleotid" title="Nikotinamidadenindinukleotid – Danish" lang="da" hreflang="da" data-title="Nikotinamidadenindinukleotid" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target">Dansk</a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Nicotinamidadenindinukleotid" title="Nicotinamidadenindinukleotid – German" lang="de" hreflang="de" data-title="Nicotinamidadenindinukleotid" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target">Deutsch</a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/NAD" title="NAD – Estonian" lang="et" hreflang="et" data-title="NAD" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target">Eesti</a></li><li class="interlanguage-link interwiki-es badge-Q17437798 badge-goodarticle mw-list-item" title="good article badge"><a href="https://es.wikipedia.org/wiki/Nicotinamida_adenina_dinucle%C3%B3tido" title="Nicotinamida adenina dinucleótido – Spanish" lang="es" hreflang="es" data-title="Nicotinamida adenina dinucleótido" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target">Español</a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/NADH" title="NADH – Esperanto" lang="eo" hreflang="eo" data-title="NADH" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target">Esperanto</a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Nikotinamida_adenina_dinukleotido" title="Nikotinamida adenina dinukleotido – Basque" lang="eu" hreflang="eu" data-title="Nikotinamida adenina dinukleotido" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target">Euskara</a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%86%DB%8C%DA%A9%D9%88%D8%AA%DB%8C%D9%86%E2%80%8C%D8%A2%D9%85%DB%8C%D8%AF_%D8%A2%D8%AF%D9%86%DB%8C%D9%86_%D8%AF%DB%8C%E2%80%8C%D9%86%D9%88%DA%A9%D9%84%D8%A6%D9%88%D8%AA%DB%8C%D8%AF" title="نیکوتین‌آمید آدنین دی‌نوکلئوتید – Persian" lang="fa" hreflang="fa" data-title="نیکوتین‌آمید آدنین دی‌نوکلئوتید" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target">فارسی</a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Nicotinamide_ad%C3%A9nine_dinucl%C3%A9otide" title="Nicotinamide adénine dinucléotide – French" lang="fr" hreflang="fr" data-title="Nicotinamide adénine dinucléotide" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target">Français</a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Dinucle%C3%B3tido_de_nicotinamida_e_adenina" title="Dinucleótido de nicotinamida e adenina – Galician" lang="gl" hreflang="gl" data-title="Dinucleótido de nicotinamida e adenina" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target">Galego</a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EB%8B%88%EC%BD%94%ED%8B%B4%EC%95%84%EB%A7%88%EC%9D%B4%EB%93%9C_%EC%95%84%EB%8D%B0%EB%8B%8C_%EB%8B%A4%EC%9D%B4%EB%89%B4%ED%81%B4%EB%A0%88%EC%98%A4%ED%83%80%EC%9D%B4%EB%93%9C" title="니코틴아마이드 아데닌 다이뉴클레오타이드 – Korean" lang="ko" hreflang="ko" data-title="니코틴아마이드 아데닌 다이뉴클레오타이드" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target">한국어</a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D5%86%D5%AB%D5%AF%D5%B8%D5%BF%D5%AB%D5%B6%D5%A1%D5%B4%D5%AB%D5%A4%D5%A1%D5%A4%D5%A5%D5%B6%D5%AB%D5%B6%D5%A5%D6%80%D5%AF%D5%B6%D5%B8%D6%82%D5%AF%D5%AC%D5%A5%D5%B8%D5%BF%D5%AB%D5%A4" title="Նիկոտինամիդադենիներկնուկլեոտիդ – Armenian" lang="hy" hreflang="hy" data-title="Նիկոտինամիդադենիներկնուկլեոտիդ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target">Հայերեն</a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Nikotinamid_adenin_dinukleotid" title="Nikotinamid adenin dinukleotid – Croatian" lang="hr" hreflang="hr" data-title="Nikotinamid adenin dinukleotid" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target">Hrvatski</a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Nikotinamida_adenina_dinukleotida" title="Nikotinamida adenina dinukleotida – Indonesian" lang="id" hreflang="id" data-title="Nikotinamida adenina dinukleotida" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target">Bahasa Indonesia</a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Nicotinammide_adenina_dinucleotide" title="Nicotinammide adenina dinucleotide – Italian" lang="it" hreflang="it" data-title="Nicotinammide adenina dinucleotide" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target">Italiano</a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/NAD" title="NAD – Hebrew" lang="he" hreflang="he" data-title="NAD" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target">עברית</a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%9D%D0%B8%D0%BA%D0%BE%D1%82%D0%B8%D0%BD%D0%B0%D0%BC%D0%B8%D0%B4%D0%B0%D0%B4%D0%B5%D0%BD%D0%B8%D0%BD%D0%B4%D0%B8%D0%BD%D1%83%D0%BA%D0%BB%D0%B5%D0%BE%D1%82%D0%B8%D0%B4" title="Никотинамидадениндинуклеотид – Kazakh" lang="kk" hreflang="kk" data-title="Никотинамидадениндинуклеотид" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target">Қазақша</a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Nicotinamidum_adeninum_dinucleotidum" title="Nicotinamidum adeninum dinucleotidum – Latin" lang="la" hreflang="la" data-title="Nicotinamidum adeninum dinucleotidum" data-language-autonym="Latina" data-language-local-name="Latin" class="interlanguage-link-target">Latina</a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Nikot%C4%ABnam%C4%ABda_aden%C4%ABndinukleot%C4%ABds" title="Nikotīnamīda adenīndinukleotīds – Latvian" lang="lv" hreflang="lv" data-title="Nikotīnamīda adenīndinukleotīds" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target">Latviešu</a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Nikotinamid-adenin-dinukleotid" title="Nikotinamid-adenin-dinukleotid – Hungarian" lang="hu" hreflang="hu" data-title="Nikotinamid-adenin-dinukleotid" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target">Magyar</a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%9D%D0%B8%D0%BA%D0%BE%D1%82%D0%B8%D0%BD%D0%B0%D0%BC%D0%B8%D0%B4_%D0%B0%D0%B4%D0%B5%D0%BD%D0%B8%D0%BD_%D0%B4%D0%B8%D0%BD%D1%83%D0%BA%D0%BB%D0%B5%D0%BE%D1%82%D0%B8%D0%B4" title="Никотинамид аденин динуклеотид – Macedonian" lang="mk" hreflang="mk" data-title="Никотинамид аденин динуклеотид" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target">Македонски</a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Nikotinamida_adenina_dinukleotida" title="Nikotinamida adenina dinukleotida – Malay" lang="ms" hreflang="ms" data-title="Nikotinamida adenina dinukleotida" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target">Bahasa Melayu</a></li><li class="interlanguage-link interwiki-nl badge-Q17437796 badge-featuredarticle mw-list-item" title="featured article badge"><a href="https://nl.wikipedia.org/wiki/Nicotinamide-adenine-dinucleotide" title="Nicotinamide-adenine-dinucleotide – Dutch" lang="nl" hreflang="nl" data-title="Nicotinamide-adenine-dinucleotide" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target">Nederlands</a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%8B%E3%82%B3%E3%83%81%E3%83%B3%E3%82%A2%E3%83%9F%E3%83%89%E3%82%A2%E3%83%87%E3%83%8B%E3%83%B3%E3%82%B8%E3%83%8C%E3%82%AF%E3%83%AC%E3%82%AA%E3%83%81%E3%83%89" title="ニコチンアミドアデニンジヌクレオチド – Japanese" lang="ja" hreflang="ja" data-title="ニコチンアミドアデニンジヌクレオチド" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target">日本語</a></li><li class="interlanguage-link interwiki-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Nicotinamida_adenina_dinucleotid" title="Nicotinamida adenina dinucleotid – Occitan" lang="oc" hreflang="oc" data-title="Nicotinamida adenina dinucleotid" data-language-autonym="Occitan" data-language-local-name="Occitan" class="interlanguage-link-target">Occitan</a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Dinukleotyd_nikotynoamidoadeninowy" title="Dinukleotyd nikotynoamidoadeninowy – Polish" lang="pl" hreflang="pl" data-title="Dinukleotyd nikotynoamidoadeninowy" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target">Polski</a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Dinucle%C3%B3tido_de_nicotinamida_e_adenina" title="Dinucleótido de nicotinamida e adenina – Portuguese" lang="pt" hreflang="pt" data-title="Dinucleótido de nicotinamida e adenina" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target">Português</a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a 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Click here for more information."><img alt="Featured article" src="//upload.wikimedia.org/wikipedia/en/thumb/e/e7/Cscr-featured.svg/20px-Cscr-featured.svg.png" decoding="async" width="20" height="19" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/e/e7/Cscr-featured.svg/30px-Cscr-featured.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/e/e7/Cscr-featured.svg/40px-Cscr-featured.svg.png 2x" data-file-width="466" data-file-height="443" /></a></div></div> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound which is reduced and oxidized</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">"NAD(P)+" and "NAD(P)H" redirect here. For the phosphates (NADP+/NADPH), see <a href="/wiki/Nicotinamide_adenine_dinucleotide_phosphate" title="Nicotinamide adenine dinucleotide phosphate">Nicotinamide adenine dinucleotide phosphate</a>.</div> <style data-mw-deduplicate="TemplateStyles:r1084375498">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> <table class="infobox ib-chembox"> <caption>Nicotinamide adenine dinucleotide </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><a href="/wiki/File:NAD%2B.svg" class="mw-file-description" title="Skeletal formula of the oxidized form"><img alt="Skeletal formula of the oxidized form" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fe/NAD%2B.svg/180px-NAD%2B.svg.png" decoding="async" width="180" height="252" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fe/NAD%2B.svg/270px-NAD%2B.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fe/NAD%2B.svg/360px-NAD%2B.svg.png 2x" data-file-width="615" data-file-height="860" /></a> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><a href="/wiki/File:NAD%2B-from-xtal-2003-3D-balls.png" class="mw-file-description" title="Ball-and-stick model of the oxidized form"><img alt="Ball-and-stick model of the oxidized form" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/NAD%2B-from-xtal-2003-3D-balls.png/220px-NAD%2B-from-xtal-2003-3D-balls.png" decoding="async" width="220" height="201" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/NAD%2B-from-xtal-2003-3D-balls.png/330px-NAD%2B-from-xtal-2003-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4c/NAD%2B-from-xtal-2003-3D-balls.png/440px-NAD%2B-from-xtal-2003-3D-balls.png 2x" data-file-width="2652" data-file-height="2426" /></a> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">Diphosphopyridine nucleotide (DPN+), Coenzyme I</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><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=53-84-9">53-84-9</a> <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" />Y</li><li><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=53-59-8">53-59-8</a> (phosphate) <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" />Y</li><li><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=58-68-4">58-68-4</a> (NADH) <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" />Y</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>NAD+: <a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=O%3DC%28N%29c1ccc%5Bn%2B%5D%28c1%29%5BC%40%40H%5D2O%5BC%40%40H%5D%28%5BC%40%40H%5D%28O%29%5BC%40H%5D2O%29COP%28%5BO-%5D%29%28%3DO%29OP%28%3DO%29%28%5BO-%5D%29OC%5BC%40H%5D5O%5BC%40%40H%5D%28n4cnc3c%28ncnc34%29N%29%5BC%40H%5D%28O%29%5BC%40%40H%5D5O">Interactive image</a></li><li>NADH: <a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=O%3DC%28N%29C1CC%3DC%5BN%5D%28C%3D1%29%5BC%40%40H%5D2O%5BC%40%40H%5D%28%5BC%40%40H%5D%28O%29%5BC%40H%5D2O%29COP%28%5BO-%5D%29%28%3DO%29OP%28%3DO%29%28%5BO-%5D%29OC%5BC%40H%5D5O%5BC%40%40H%5D%28n4cnc3c%28ncnc34%29N%29%5BC%40H%5D%28O%29%5BC%40%40H%5D5O">Interactive image</a></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><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=16908">CHEBI:16908</a> <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" />N</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><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL1628272">ChEMBL1628272</a> <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" />N</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><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.5681.html">5681</a> <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" />Y</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><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB00157">DB00157</a> <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" />Y</li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard">ECHA InfoCard</a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.000.169">100.000.169</a> <a href="https://www.wikidata.org/wiki/Q12499775#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> </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><a rel="nofollow" class="external text" href="http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?tab=summary&ligandId=2451">2451</a></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><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C00003">C00003</a> <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" />N</li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/925">925</a></li></ul></div> </td></tr> <tr> <td><a href="/wiki/RTECS" class="mw-redirect" title="RTECS">RTECS number</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>UU3450000</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><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/0U46U6E8UK">0U46U6E8UK</a> <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" />Y</li><li><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/BY8P107XEP">BY8P107XEP</a> (phosphate) <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" />Y</li><li><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/4J24DQ0916">4J24DQ0916</a> (NADH) <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" />Y</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/C21H27N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1-4,7-8,10-11,13-16,20-21,29-32H,5-6H2,(H5-,22,23,24,25,33,34,35,36,37)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1 <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" />Y</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: BAWFJGJZGIEFAR-NNYOXOHSSA-N <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" />Y</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/C21H27N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1-4,7-8,10-11,13-16,20-21,29-32H,5-6H2,(H5-,22,23,24,25,33,34,35,36,37)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: BAWFJGJZGIEFAR-NNYOXOHSBR</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%;">NAD+: O=C(N)c1ccc[n+](c1)[C@@H]2O[C@@H]([C@@H](O)[C@H]2O)COP([O-])(=O)OP(=O)([O-])OC[C@H]5O[C@@H](n4cnc3c(ncnc34)N)[C@H](O)[C@@H]5O</div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">NADH: O=C(N)C1CC=C[N](C=1)[C@@H]2O[C@@H]([C@@H](O)[C@H]2O)COP([O-])(=O)OP(=O)([O-])OC[C@H]5O[C@@H](n4cnc3c(ncnc34)N)[C@H](O)[C@@H]5O</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>C21H28N7O14P2<a href="#cite_note-1">[1]</a><a href="#cite_note-2">[2]</a> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td>663.43 g/mol </td></tr> <tr> <td>Appearance </td> <td>White powder </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>160 °C (320 °F; 433 K) </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><a href="/wiki/Occupational_safety_and_health" title="Occupational safety and health">Occupational safety and health</a> (OHS/OSH): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Main hazards</div> </td> <td>Not hazardous </td></tr> <tr> <td><a href="/wiki/NFPA_704" title="NFPA 704">NFPA 704</a> (fire diamond) </td> <td><style data-mw-deduplicate="TemplateStyles:r1170367383">.mw-parser-output .nfpa-704-diamond-ref{float:right;padding:1px;text-align:right}.mw-parser-output .nfpa-704-diamond-container{width:82px;font-family:sans-serif;margin:0 auto}.mw-parser-output .nfpa-704-diamond-container-ref{float:left;margin-left:1em}.mw-parser-output .nfpa-704-diamond-images{float:left;font-size:20px;text-align:center;position:relative;height:80px;width:80px;padding:1px}.mw-parser-output .nfpa-704-diamond-map{position:absolute;height:80px;width:80px}.mw-parser-output .nfpa-704-diamond .noresize{margin:0 auto}.mw-parser-output .nfpa-704-diamond-code{line-height:1em;text-align:center;position:absolute}.mw-parser-output .nfpa-704-diamond-code>a{color:black}.mw-parser-output .nfpa-704-diamond-blue{width:13px;top:31px;left:15px}.mw-parser-output .nfpa-704-diamond-red{width:12px;top:12px;left:35px}.mw-parser-output .nfpa-704-diamond-yellow{width:13px;top:31px;left:54px}.mw-parser-output .nfpa-704-diamond-white-image{position:relative;top:51px;left:0}.mw-parser-output .nfpa-704-diamond-white-text{vertical-align:middle;text-align:center;line-height:80%;position:absolute;top:52px}.mw-parser-output .nfpa-704-diamond-white-text a>span{position:absolute;color:black}.mw-parser-output .nfpa-704-diamond-white-wors{font-size:15px;width:23px;left:29px}.mw-parser-output .nfpa-704-diamond-white-wox{font-size:15px;font-stretch:condensed;width:21px;line-height:80%;top:-4px;left:29px}.mw-parser-output .nfpa-704-diamond-white-abcp{font-size:13.5px;font-stretch:condensed;width:28px;left:26px}.mw-parser-output .nfpa-704-diamond-white-ac{font-size:10px;width:30px;left:25px}.mw-parser-output .nfpa-704-diamond-white-strike{text-decoration:line-through}</style><div class="nfpa-704-diamond notheme"><div class="nfpa-704-diamond-container"><div class="nfpa-704-diamond-images nounderlines"> <div class="nfpa-704-diamond-map"><figure class="noresize" typeof="mw:File"><img alt="NFPA 704 four-colored diamond" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/80px-NFPA_704.svg.png" decoding="async" width="80" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/120px-NFPA_704.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/160px-NFPA_704.svg.png 2x" data-file-width="512" data-file-height="512" usemap="#ImageMap_811dcee2cbfc5fb2" /><map name="ImageMap_811dcee2cbfc5fb2"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine" title="Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine" /><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" title="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" /><area href="/wiki/NFPA_704#Yellow" shape="poly" coords="70,23,94,47,70,70,47,47" alt="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" /><area href="/wiki/NFPA_704#White" shape="poly" coords="47,47,70,70,47,94,23,70" alt="Special hazards (white): no code" title="Special hazards (white): no code" /></map><figcaption></figcaption></figure></div><div class="nfpa-704-diamond-code nfpa-704-diamond-blue"> <a href="/wiki/NFPA_704#Blue" title="NFPA 704">1</a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-red"> <a href="/wiki/NFPA_704#Red" title="NFPA 704">1</a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-yellow"> <a href="/wiki/NFPA_704#Yellow" title="NFPA 704">0</a></div></div></div></div> </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;"><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/12px-X_mark.svg.png" decoding="async" width="12" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/18px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/24px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" />N <a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=464362739&page2=Nicotinamide+adenine+dinucleotide">verify</a> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <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" />Y<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" />N ?) </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> Nicotinamide adenine dinucleotide (NAD) is a <a href="/wiki/Cofactor_(biochemistry)" title="Cofactor (biochemistry)">coenzyme</a> central to <a href="/wiki/Metabolism" title="Metabolism">metabolism</a>.<a href="#cite_note-3">[3]</a> Found in all living <a href="/wiki/Cell_(biology)" title="Cell (biology)">cells</a>, NAD is called a dinucleotide because it consists of two <a href="/wiki/Nucleotide" title="Nucleotide">nucleotides</a> joined through their <a href="/wiki/Phosphate" title="Phosphate">phosphate</a> groups. One nucleotide contains an <a href="/wiki/Adenine" title="Adenine">adenine</a> <a href="/wiki/Nucleobase" class="mw-redirect" title="Nucleobase">nucleobase</a> and the other, <a href="/wiki/Nicotinamide" title="Nicotinamide">nicotinamide</a>. NAD exists in two forms: an <a href="/wiki/Redox" title="Redox">oxidized and reduced</a> form, abbreviated as NAD+ and NADH (H for <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a>), respectively. In cellular metabolism, NAD is involved in redox reactions, carrying <a href="/wiki/Electron" title="Electron">electrons</a> from one reaction to another, so it is found in two forms: NAD+ is an <a href="/wiki/Oxidizing_agent" title="Oxidizing agent">oxidizing agent</a>, accepting electrons from other molecules and becoming reduced; with H+, this reaction forms NADH, which can be used as a <a href="/wiki/Reducing_agent" title="Reducing agent">reducing agent</a> to donate electrons. These <a href="/wiki/Electron_transfer" title="Electron transfer">electron transfer</a> reactions are the main function of NAD. It is also used in other cellular processes, most notably as a <a href="/wiki/Substrate_(biochemistry)" class="mw-redirect" title="Substrate (biochemistry)">substrate</a> of <a href="/wiki/Enzyme" title="Enzyme">enzymes</a> in adding or removing <a href="/wiki/Chemical_group" class="mw-redirect" title="Chemical group">chemical groups</a> to or from <a href="/wiki/Protein" title="Protein">proteins</a>, in <a href="/wiki/Posttranslational_modification" class="mw-redirect" title="Posttranslational modification">posttranslational modifications</a>. Because of the importance of these functions, the enzymes involved in NAD metabolism are targets for <a href="/wiki/Drug_discovery" title="Drug discovery">drug discovery</a>. In organisms, NAD can be synthesized from simple building-blocks (<a href="/wiki/De_novo_synthesis" title="De novo synthesis">de novo</a>) from either <a href="/wiki/Tryptophan" title="Tryptophan">tryptophan</a> or <a href="/wiki/Aspartic_acid" title="Aspartic acid">aspartic acid</a>, each a case of an <a href="/wiki/Amino_acid" title="Amino acid">amino acid</a>. Alternatively, more complex components of the coenzymes are taken up from nutritive compounds such as <a href="/wiki/Niacin" title="Niacin">niacin</a>; similar compounds are produced by reactions that break down the structure of NAD, providing a <a href="/wiki/Salvage_pathway" class="mw-redirect" title="Salvage pathway">salvage pathway</a> that recycles them back into their respective active form. Some NAD is converted into the coenzyme <a href="/wiki/Nicotinamide_adenine_dinucleotide_phosphate" title="Nicotinamide adenine dinucleotide phosphate">nicotinamide adenine dinucleotide phosphate</a> (NADP), whose chemistry largely parallels that of NAD, though its predominant role is as a coenzyme in <a href="/wiki/Anabolic" class="mw-redirect" title="Anabolic">anabolic</a> metabolism. In the name NAD+, the <a href="/wiki/Subscript_and_superscript" title="Subscript and superscript">superscripted</a> plus sign indicates the positive <a href="/wiki/Formal_charge" title="Formal charge">formal charge</a> on one of its nitrogen atoms. <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Physical_and_chemical_properties">Physical and chemical properties</h2>[<a href="/w/index.php?title=Nicotinamide_adenine_dinucleotide&action=edit&section=1" title="Edit section: Physical and chemical properties">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Further information: <a href="/wiki/Redox" title="Redox">Redox</a></div> Nicotinamide adenine dinucleotide consists of two <a href="/wiki/Nucleoside" title="Nucleoside">nucleosides</a> joined by <a href="/wiki/Pyrophosphate" title="Pyrophosphate">pyrophosphate</a>. The nucleosides each contain a <a href="/wiki/Ribose" title="Ribose">ribose</a> ring, one with <a href="/wiki/Adenine" title="Adenine">adenine</a> attached to the first carbon atom (the <a href="/wiki/Nucleic_acid_nomenclature" class="mw-redirect" title="Nucleic acid nomenclature">1'</a> position) (<a href="/wiki/Adenosine_diphosphate_ribose" title="Adenosine diphosphate ribose">adenosine diphosphate ribose</a>) and the other with <a href="/wiki/Nicotinamide" title="Nicotinamide">nicotinamide</a> at this position.<a href="#cite_note-4">[4]</a><a href="#cite_note-Pollak-5">[5]</a> <figure class="mw-default-size mw-halign-left skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:NAD_oxidation_reduction.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b5/NAD_oxidation_reduction.svg/220px-NAD_oxidation_reduction.svg.png" decoding="async" width="220" height="132" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b5/NAD_oxidation_reduction.svg/330px-NAD_oxidation_reduction.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b5/NAD_oxidation_reduction.svg/440px-NAD_oxidation_reduction.svg.png 2x" data-file-width="920" data-file-height="550" /></a><figcaption>The <a href="/wiki/Redox" title="Redox">redox</a> reactions of nicotinamide adenine dinucleotide</figcaption></figure> The compound accepts or donates the equivalent of H−.<a href="#cite_note-Belenky-6">[6]</a> Such reactions (summarized in formula below) involve the removal of two hydrogen atoms from the reactant (R), in the form of a <a href="/wiki/Hydride" title="Hydride">hydride ion</a> (H−), and a <a href="/wiki/Proton" title="Proton">proton</a> (H+). The proton is released into solution, while the reductant RH2 is oxidized and NAD+ reduced to NADH by transfer of the hydride to the nicotinamide ring. <dl><dd>RH2 + NAD+ → NADH + H+ + R;</dd></dl> From the hydride electron pair, one electron is attracted to the slightly more electronegative atom of the nicotinamide ring of NAD+, becoming part of the nicotinamide moiety. The second electron and proton atom are transferred to the carbon atom adjacent to the N atom. The <a href="/wiki/Standard_electrode_potential#Non-standard_condition" title="Standard electrode potential">midpoint potential</a> of the NAD+/NADH redox pair is −0.32 <a href="/wiki/Volt" title="Volt">volts</a>, which makes NADH a moderately strong reducing agent.<a href="#cite_note-Unden-7">[7]</a> The reaction is easily reversible, when NADH reduces another molecule and is re-oxidized to NAD+. This means the coenzyme can continuously cycle between the NAD+ and NADH forms without being consumed.<a href="#cite_note-Pollak-5">[5]</a> In appearance, all forms of this coenzyme are white <a href="/wiki/Amorphous_solid" title="Amorphous solid">amorphous</a> powders that are <a href="/wiki/Hygroscopy" title="Hygroscopy">hygroscopic</a> and highly water-soluble.<a href="#cite_note-8">[8]</a> The solids are stable if stored dry and in the dark. Solutions of NAD+ are colorless and stable for about a week at 4 <a href="/wiki/Celsius" title="Celsius">°C</a> and neutral <a href="/wiki/PH" title="PH">pH</a>, but decompose rapidly in acidic or alkaline solutions. Upon decomposition, they form products that are <a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">enzyme inhibitors</a>.<a href="#cite_note-9">[9]</a> <figure class="mw-default-size skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:NADNADH.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/89/NADNADH.svg/220px-NADNADH.svg.png" decoding="async" width="220" height="174" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/89/NADNADH.svg/330px-NADNADH.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/89/NADNADH.svg/440px-NADNADH.svg.png 2x" data-file-width="364" data-file-height="288" /></a><figcaption><a href="/wiki/Ultraviolet" title="Ultraviolet">UV</a> absorption spectra of NAD+ and NADH[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">image reference needed</a>]</figcaption></figure> Both NAD+ and NADH strongly absorb <a href="/wiki/Ultraviolet" title="Ultraviolet">ultraviolet</a> light because of the adenine. For example, peak absorption of NAD+ is at a <a href="/wiki/Wavelength" title="Wavelength">wavelength</a> of 259 <a href="/wiki/Nanometer" class="mw-redirect" title="Nanometer">nanometers</a> (nm), with an <a href="/wiki/Molar_absorptivity" class="mw-redirect" title="Molar absorptivity">extinction coefficient</a> of 16,900 <a href="/wiki/Concentration#Molarity" title="Concentration">M</a>−1<a href="/wiki/Centimetre" title="Centimetre">cm</a>−1. NADH also absorbs at higher wavelengths, with a second peak in UV absorption at 339 nm with an extinction coefficient of 6,220 M−1cm−1.<a href="#cite_note-Dawson-10">[10]</a> This difference in the ultraviolet <a href="/wiki/Absorption_spectra" class="mw-redirect" title="Absorption spectra">absorption spectra</a> between the oxidized and reduced forms of the coenzymes at higher wavelengths makes it simple to measure the conversion of one to another in <a href="/wiki/Enzyme_assay" title="Enzyme assay">enzyme assays</a> – by measuring the amount of UV absorption at 340 nm using a <a href="/wiki/Spectrophotometry" title="Spectrophotometry">spectrophotometer</a>.<a href="#cite_note-Dawson-10">[10]</a> NAD+ and NADH also differ in their <a href="/wiki/Fluorescence" title="Fluorescence">fluorescence</a>. Freely diffusing NADH in aqueous solution, when excited at the nicotinamide absorbance of ~335 nm (near-UV), fluoresces at 445–460 nm (violet to blue) with a <a href="/wiki/Fluorescence#Lifetime" title="Fluorescence">fluorescence lifetime</a> of 0.4 <a href="/wiki/Nanosecond" title="Nanosecond">nanoseconds</a>, while NAD+ does not fluoresce.<a href="#cite_note-Blacker_Mann_Gale_Ziegler_p.-11">[11]</a><a href="#cite_note-Lakowicz-12">[12]</a> The properties of the fluorescence signal changes when NADH binds to <a href="/wiki/Protein" title="Protein">proteins</a>, so these changes can be used to measure <a href="/wiki/Dissociation_constant" title="Dissociation constant">dissociation constants</a>, which are useful in the study of <a href="/wiki/Enzyme_kinetics" title="Enzyme kinetics">enzyme kinetics</a>.<a href="#cite_note-Lakowicz-12">[12]</a><a href="#cite_note-13">[13]</a> These changes in fluorescence are also used to measure changes in the redox state of living cells, through <a href="/wiki/Fluorescence_microscope" title="Fluorescence microscope">fluorescence microscopy</a>.<a href="#cite_note-Kasimova-14">[14]</a> NADH can be converted to NAD+ in a reaction catalysed by copper, which requires hydrogen peroxide. Thus, the supply of NAD+ in cells requires mitochondrial copper(II).<a href="#cite_note-15">[15]</a><a href="#cite_note-16">[16]</a> <div class="mw-heading mw-heading2"><h2 id="Concentration_and_state_in_cells">Concentration and state in cells</h2>[<a href="/w/index.php?title=Nicotinamide_adenine_dinucleotide&action=edit&section=2" title="Edit section: Concentration and state in cells">edit</a>]</div> In rat liver, the total amount of NAD+ and NADH is approximately 1 <a href="/wiki/Micromole" class="mw-redirect" title="Micromole">μmole</a> per <a href="/wiki/Gram" title="Gram">gram</a> of wet weight, about 10 times the concentration of NADP+ and NADPH in the same cells.<a href="#cite_note-17">[17]</a> The actual concentration of NAD+ in cell <a href="/wiki/Cytosol" title="Cytosol">cytosol</a> is harder to measure, with recent estimates in animal cells ranging around 0.3 <a href="/wiki/Molar_concentration" title="Molar concentration">mM</a>,<a href="#cite_note-18">[18]</a><a href="#cite_note-Yang-19">[19]</a> and approximately 1.0 to 2.0 mM in <a href="/wiki/Yeast" title="Yeast">yeast</a>.<a href="#cite_note-Belenky2-20">[20]</a> However, more than 80% of NADH fluorescence in mitochondria is from bound form, so the concentration in solution is much lower.<a href="#cite_note-21">[21]</a> NAD+ concentrations are highest in the mitochondria, constituting 40% to 70% of the total cellular NAD+.<a href="#cite_note-pmid31412683-22">[22]</a> NAD+ in the cytosol is carried into the mitochondrion by a specific <a href="/wiki/Membrane_transport_protein" title="Membrane transport protein">membrane transport protein</a>, since the coenzyme cannot <a href="/wiki/Diffusion" title="Diffusion">diffuse</a> across membranes.<a href="#cite_note-23">[23]</a> The intracellular <a href="/wiki/Biological_half-life" title="Biological half-life">half-life</a> of NAD+ was claimed to be between 1–2 hours by one review,<a href="#cite_note-pmid27465020-24">[24]</a> whereas another review gave varying estimates based on compartment: intracellular 1–4 hours, cytoplasmic 2 hours, and mitochondrial 4–6 hours.<a href="#cite_note-pmid29413178-25">[25]</a> The balance between the oxidized and reduced forms of nicotinamide adenine dinucleotide is called the NAD+/NADH ratio. This ratio is an important component of what is called the redox state of a cell, a measurement that reflects both the metabolic activities and the health of cells.<a href="#cite_note-26">[26]</a> The effects of the NAD+/NADH ratio are complex, controlling the activity of several key enzymes, including <a href="/wiki/Glyceraldehyde_3-phosphate_dehydrogenase" title="Glyceraldehyde 3-phosphate dehydrogenase">glyceraldehyde 3-phosphate dehydrogenase</a> and <a href="/wiki/Pyruvate_dehydrogenase" title="Pyruvate dehydrogenase">pyruvate dehydrogenase</a>. In healthy mammalian tissues, estimates of the ratio of free NAD+ to NADH in the cytoplasm typically lie around 700:1; the ratio is thus favorable for oxidative reactions.<a href="#cite_note-Williamson-27">[27]</a><a href="#cite_note-Zhang-28">[28]</a> The ratio of total NAD+/NADH is much lower, with estimates ranging from 3–10 in mammals.<a href="#cite_note-29">[29]</a> In contrast, the <a href="/wiki/Nicotinamide_adenine_dinucleotide_phosphate" title="Nicotinamide adenine dinucleotide phosphate">NADP+/NADPH</a> ratio is normally about 0.005, so NADPH is the dominant form of this coenzyme.<a href="#cite_note-30">[30]</a> These different ratios are key to the different metabolic roles of NADH and NADPH. <div class="mw-heading mw-heading2"><h2 id="Biosynthesis">Biosynthesis</h2>[<a href="/w/index.php?title=Nicotinamide_adenine_dinucleotide&action=edit&section=3" title="Edit section: Biosynthesis">edit</a>]</div> NAD+ is synthesized through two metabolic pathways. It is produced either in a <a href="/wiki/De_novo_synthesis" title="De novo synthesis">de novo</a> pathway from amino acids or in salvage pathways by recycling preformed components such as <a href="/wiki/Nicotinamide" title="Nicotinamide">nicotinamide</a> back to NAD+. Although most tissues synthesize NAD+ by the salvage pathway in mammals, much more de novo synthesis occurs in the liver from tryptophan, and in the kidney and <a href="/wiki/Macrophage" title="Macrophage">macrophages</a> from <a href="/wiki/Nicotinic_acid" class="mw-redirect" title="Nicotinic acid">nicotinic acid</a>.<a href="#cite_note-pmid32097708-31">[31]</a> <div class="mw-heading mw-heading3"><h3 id="De_novo_production">De novo production</h3>[<a href="/w/index.php?title=Nicotinamide_adenine_dinucleotide&action=edit&section=4" title="Edit section: De novo production">edit</a>]</div> <figure class="mw-default-size skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:NAD_metabolism.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e3/NAD_metabolism.svg/330px-NAD_metabolism.svg.png" decoding="async" width="330" height="135" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e3/NAD_metabolism.svg/495px-NAD_metabolism.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e3/NAD_metabolism.svg/660px-NAD_metabolism.svg.png 2x" data-file-width="443" data-file-height="181" /></a><figcaption>Some <a href="/wiki/Metabolic_pathway" title="Metabolic pathway">metabolic pathways</a> that synthesize and consume NAD+ in <a href="/wiki/Vertebrate" title="Vertebrate">vertebrates</a>.[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">image reference needed</a>] The abbreviations are defined in the text.</figcaption></figure> Most organisms synthesize NAD+ from simple components.<a href="#cite_note-Belenky-6">[6]</a> The specific set of reactions differs among organisms, but a common feature is the generation of <a href="/wiki/Quinolinic_acid" title="Quinolinic acid">quinolinic acid</a> (QA) from an amino acid – either <a href="/wiki/Tryptophan" title="Tryptophan">tryptophan</a> (Trp) in animals and some bacteria, or <a href="/wiki/Aspartic_acid" title="Aspartic acid">aspartic acid</a> (Asp) in some bacteria and plants.<a href="#cite_note-32">[32]</a><a href="#cite_note-33">[33]</a> The quinolinic acid is converted to nicotinic acid mononucleotide (NaMN) by transfer of a phosphoribose moiety. An adenylate moiety is then transferred to form nicotinic acid adenine dinucleotide (NaAD). Finally, the nicotinic acid moiety in NaAD is <a href="/wiki/Amide" title="Amide">amidated</a> to a nicotinamide (Nam) moiety, forming nicotinamide adenine dinucleotide.<a href="#cite_note-Belenky-6">[6]</a> In a further step, some NAD+ is converted into NADP+ by <a href="/wiki/NAD%2B_kinase" title="NAD+ kinase">NAD+ kinase</a>, which <a href="/wiki/Phosphorylates" class="mw-redirect" title="Phosphorylates">phosphorylates</a> NAD+.<a href="#cite_note-34">[34]</a> In most organisms, this enzyme uses <a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">adenosine triphosphate</a> (ATP) as the source of the phosphate group, although several bacteria such as <a href="/wiki/Mycobacterium_tuberculosis" title="Mycobacterium tuberculosis">Mycobacterium tuberculosis</a> and a hyperthermophilic <a href="/wiki/Archaeon" class="mw-redirect" title="Archaeon">archaeon</a> <a href="/wiki/Pyrococcus" title="Pyrococcus">Pyrococcus horikoshii</a>, use inorganic <a href="/wiki/Polyphosphate" title="Polyphosphate">polyphosphate</a> as an alternative phosphoryl donor.<a href="#cite_note-35">[35]</a><a href="#cite_note-36">[36]</a> <figure class="mw-default-size mw-halign-left skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:NA,_N_and_NR.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/88/NA%2C_N_and_NR.svg/290px-NA%2C_N_and_NR.svg.png" decoding="async" width="290" height="126" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/88/NA%2C_N_and_NR.svg/435px-NA%2C_N_and_NR.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/88/NA%2C_N_and_NR.svg/580px-NA%2C_N_and_NR.svg.png 2x" data-file-width="1200" data-file-height="520" /></a><figcaption>Salvage pathways use three precursors for NAD+.</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Salvage_pathways">Salvage pathways</h3>[<a href="/w/index.php?title=Nicotinamide_adenine_dinucleotide&action=edit&section=5" title="Edit section: Salvage pathways">edit</a>]</div> Despite the presence of the de novo pathway, the salvage reactions are essential in humans; a lack of <a href="/wiki/Niacin" title="Niacin">niacin</a> in the diet causes the <a href="/wiki/Vitamin_deficiency" title="Vitamin deficiency">vitamin deficiency</a> disease <a href="/wiki/Pellagra" title="Pellagra">pellagra</a>.<a href="#cite_note-37">[37]</a> This high requirement for NAD+ results from the constant consumption of the coenzyme in reactions such as posttranslational modifications, since the cycling of NAD+ between oxidized and reduced forms in redox reactions does not change the overall levels of the coenzyme.<a href="#cite_note-Belenky-6">[6]</a> The major source of NAD+ in mammals is the salvage pathway which recycles the <a href="/wiki/Nicotinamide" title="Nicotinamide">nicotinamide</a> produced by enzymes utilizing NAD+.<a href="#cite_note-pmid29514064-38">[38]</a> The first step, and the rate-limiting enzyme in the salvage pathway is <a href="/wiki/Nicotinamide_phosphoribosyltransferase" title="Nicotinamide phosphoribosyltransferase">nicotinamide phosphoribosyltransferase</a> (NAMPT), which produces <a href="/wiki/Nicotinamide_mononucleotide" title="Nicotinamide mononucleotide">nicotinamide mononucleotide</a> (NMN).<a href="#cite_note-pmid29514064-38">[38]</a> NMN is the immediate precursor to NAD+ in the salvage pathway.<a href="#cite_note-39">[39]</a> Besides assembling NAD+ de novo from simple amino acid precursors, cells also salvage preformed compounds containing a pyridine base. The three vitamin precursors used in these salvage metabolic pathways are nicotinic acid (NA), nicotinamide (Nam) and <a href="/wiki/Nicotinamide_riboside" title="Nicotinamide riboside">nicotinamide riboside</a> (NR).<a href="#cite_note-Belenky-6">[6]</a> These compounds can be taken up from the diet and are termed vitamin B3 or niacin. However, these compounds are also produced within cells and by digestion of cellular NAD+. Some of the enzymes involved in these salvage pathways appear to be concentrated in the <a href="/wiki/Cell_nucleus" title="Cell nucleus">cell nucleus</a>, which may compensate for the high level of reactions that consume NAD+ in this <a href="/wiki/Organelle" title="Organelle">organelle</a>.<a href="#cite_note-40">[40]</a> There are some reports that mammalian cells can take up extracellular NAD+ from their surroundings,<a href="#cite_note-41">[41]</a> and both nicotinamide and nicotinamide riboside can be absorbed from the gut.<a href="#cite_note-42">[42]</a> The salvage pathways used in <a href="/wiki/Microorganism" title="Microorganism">microorganisms</a> differ from those of <a href="/wiki/Mammal" title="Mammal">mammals</a>.<a href="#cite_note-Rongvaux-43">[43]</a> Some pathogens, such as the yeast <a href="/wiki/Candida_glabrata" class="mw-redirect" title="Candida glabrata">Candida glabrata</a> and the bacterium <a href="/wiki/Haemophilus_influenzae" title="Haemophilus influenzae">Haemophilus influenzae</a> are NAD+ <a href="/wiki/Auxotroph" class="mw-redirect" title="Auxotroph">auxotrophs</a> – they cannot synthesize NAD+ – but possess salvage pathways and thus are dependent on external sources of NAD+ or its precursors.<a href="#cite_note-44">[44]</a><a href="#cite_note-45">[45]</a> Even more surprising is the intracellular <a href="/wiki/Pathogen" title="Pathogen">pathogen</a> <a href="/wiki/Chlamydia_trachomatis" title="Chlamydia trachomatis">Chlamydia trachomatis</a>, which lacks recognizable candidates for any genes involved in the biosynthesis or salvage of both NAD+ and NADP+, and must acquire these coenzymes from its <a href="/wiki/Host_(biology)" title="Host (biology)">host</a>.<a href="#cite_note-46">[46]</a> <div class="mw-heading mw-heading2"><h2 id="Functions">Functions</h2>[<a href="/w/index.php?title=Nicotinamide_adenine_dinucleotide&action=edit&section=6" title="Edit section: Functions">edit</a>]</div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Rossman_fold.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/31/Rossman_fold.png/220px-Rossman_fold.png" decoding="async" width="220" height="239" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/31/Rossman_fold.png/330px-Rossman_fold.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/31/Rossman_fold.png/440px-Rossman_fold.png 2x" data-file-width="941" data-file-height="1024" /></a><figcaption><a href="/wiki/Rossmann_fold" title="Rossmann fold">Rossmann fold</a> in part of the <a href="/wiki/Lactate_dehydrogenase" title="Lactate dehydrogenase">lactate dehydrogenase</a> of <a href="/wiki/Cryptosporidium_parvum" title="Cryptosporidium parvum">Cryptosporidium parvum</a>, showing NAD+ in red, beta sheets in yellow, and alpha helices in purple<a href="#cite_note-47">[47]</a></figcaption></figure> Nicotinamide adenine dinucleotide has several essential roles in <a href="/wiki/Metabolism" title="Metabolism">metabolism</a>. It acts as a <a href="/wiki/Coenzyme" class="mw-redirect" title="Coenzyme">coenzyme</a> in <a href="/wiki/Redox" title="Redox">redox</a> reactions, as a donor of ADP-ribose moieties in <a href="/wiki/ADP-ribosylation" title="ADP-ribosylation">ADP-ribosylation</a> reactions, as a precursor of the <a href="/wiki/Second_messenger" class="mw-redirect" title="Second messenger">second messenger</a> molecule <a href="/wiki/Cyclic_ADP-ribose" title="Cyclic ADP-ribose">cyclic ADP-ribose</a>, as well as acting as a substrate for bacterial <a href="/wiki/DNA_ligase" title="DNA ligase">DNA ligases</a> and a group of enzymes called <a href="/wiki/Sirtuin" title="Sirtuin">sirtuins</a> that use NAD+ to remove <a href="/wiki/Acetyl" class="mw-redirect" title="Acetyl">acetyl</a> groups from proteins. In addition to these metabolic functions, NAD+ emerges as an adenine nucleotide that can be released from cells spontaneously and by regulated mechanisms,<a href="#cite_note-Smyth-48">[48]</a><a href="#cite_note-Billington-49">[49]</a> and can therefore have important <a href="/wiki/Extracellular" class="mw-redirect" title="Extracellular">extracellular</a> roles.<a href="#cite_note-Billington-49">[49]</a> <div class="mw-heading mw-heading3"><h3 id="Oxidoreductase_binding_of_NAD">Oxidoreductase binding of NAD</h3>[<a href="/w/index.php?title=Nicotinamide_adenine_dinucleotide&action=edit&section=7" title="Edit section: Oxidoreductase binding of NAD">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Further information: <a href="/wiki/Protein_structure" title="Protein structure">Protein structure</a> and <a href="/wiki/Oxidoreductase" title="Oxidoreductase">Oxidoreductase</a></div> The main role of NAD+ in metabolism is the transfer of electrons from one molecule to another. Reactions of this type are catalyzed by a large group of enzymes called <a href="/wiki/Oxidoreductase" title="Oxidoreductase">oxidoreductases</a>. The correct names for these enzymes contain the names of both their substrates: for example <a href="/wiki/NADH_dehydrogenase" title="NADH dehydrogenase">NADH-ubiquinone oxidoreductase</a> catalyzes the oxidation of NADH by <a href="/wiki/Coenzyme_Q" class="mw-redirect" title="Coenzyme Q">coenzyme Q</a>.<a href="#cite_note-50">[50]</a> However, these enzymes are also referred to as dehydrogenases or reductases, with NADH-ubiquinone oxidoreductase commonly being called NADH dehydrogenase or sometimes coenzyme Q reductase.<a href="#cite_note-51">[51]</a> There are many different superfamilies of enzymes that bind NAD+ / NADH. One of the most common superfamilies includes a <a href="/wiki/Structural_motif" title="Structural motif">structural motif</a> known as the <a href="/wiki/Rossmann_fold" title="Rossmann fold">Rossmann fold</a>.<a href="#cite_note-2015-Hanukoglu-52">[52]</a><a href="#cite_note-53">[53]</a> The motif is named after <a href="/wiki/Michael_Rossmann" title="Michael Rossmann">Michael Rossmann</a>, who was the first scientist to notice how common this structure is within nucleotide-binding proteins.<a href="#cite_note-Rao-54">[54]</a> An example of a NAD-binding bacterial enzyme involved in <a href="/wiki/Amino_acid" title="Amino acid">amino acid</a> metabolism that does not have the Rossmann fold is found in <a href="/wiki/Pseudomonas_syringae" title="Pseudomonas syringae">Pseudomonas syringae</a> pv. tomato (<a href="/wiki/Protein_Data_Bank" title="Protein Data Bank">PDB</a>: <a rel="nofollow" class="external text" href="https://www.rcsb.org/structure/2CWH">2CWH</a>; <a href="/wiki/InterPro" title="InterPro">InterPro</a>: <a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/interpro/entry/IPR003767">IPR003767</a>).<a href="#cite_note-55">[55]</a> <figure class="mw-default-size mw-halign-left skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:NAD%2B_phys_alt.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/NAD%2B_phys_alt.svg/220px-NAD%2B_phys_alt.svg.png" decoding="async" width="220" height="320" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/NAD%2B_phys_alt.svg/330px-NAD%2B_phys_alt.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4c/NAD%2B_phys_alt.svg/440px-NAD%2B_phys_alt.svg.png 2x" data-file-width="363" data-file-height="528" /></a><figcaption>In this diagram, the hydride acceptor C4 carbon is shown at the top. When the nicotinamide ring lies in the plane of the page with the carboxy-amide to the right, as shown, the hydride donor lies either "above" or "below" the plane of the page. If "above" hydride transfer is class A, if "below" hydride transfer is class B.<a href="#cite_note-bellamacina-56">[56]</a></figcaption></figure> When bound in the active site of an oxidoreductase, the nicotinamide ring of the coenzyme is positioned so that it can accept a hydride from the other substrate. Depending on the enzyme, the hydride donor is positioned either "above" or "below" the plane of the planar C4 carbon, as defined in the figure. Class A oxidoreductases transfer the atom from above; class B enzymes transfer it from below. Since the C4 carbon that accepts the hydrogen is <a href="/wiki/Prochiral" class="mw-redirect" title="Prochiral">prochiral</a>, this can be exploited in <a href="/wiki/Enzyme_kinetics" title="Enzyme kinetics">enzyme kinetics</a> to give information about the enzyme's mechanism. This is done by mixing an enzyme with a substrate that has <a href="/wiki/Deuterium" title="Deuterium">deuterium</a> atoms substituted for the hydrogens, so the enzyme will reduce NAD+ by transferring deuterium rather than hydrogen. In this case, an enzyme can produce one of two <a href="/wiki/Stereoisomerism" title="Stereoisomerism">stereoisomers</a> of NADH.<a href="#cite_note-bellamacina-56">[56]</a> Despite the similarity in how proteins bind the two coenzymes, enzymes almost always show a high level of specificity for either NAD+ or NADP+.<a href="#cite_note-57">[57]</a> This specificity reflects the distinct metabolic roles of the respective coenzymes, and is the result of distinct sets of <a href="/wiki/Amino_acid" title="Amino acid">amino acid</a> residues in the two types of coenzyme-binding pocket. For instance, in the active site of NADP-dependent enzymes, an <a href="/wiki/Ionic_bond" class="mw-redirect" title="Ionic bond">ionic bond</a> is formed between a basic amino acid side-chain and the acidic phosphate group of NADP+. On the converse, in NAD-dependent enzymes the charge in this pocket is reversed, preventing NADP+ from binding. However, there are a few exceptions to this general rule, and enzymes such as <a href="/wiki/Aldose_reductase" title="Aldose reductase">aldose reductase</a>, <a href="/wiki/Glucose-6-phosphate_dehydrogenase" title="Glucose-6-phosphate dehydrogenase">glucose-6-phosphate dehydrogenase</a>, and <a href="/wiki/Methylenetetrahydrofolate_reductase" title="Methylenetetrahydrofolate reductase">methylenetetrahydrofolate reductase</a> can use both coenzymes in some species.<a href="#cite_note-58">[58]</a> <div class="mw-heading mw-heading3"><h3 id="Role_in_redox_metabolism">Role in redox metabolism</h3>[<a href="/w/index.php?title=Nicotinamide_adenine_dinucleotide&action=edit&section=8" title="Edit section: Role in redox metabolism">edit</a>]</div> <figure class="mw-default-size skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Catabolism_schematic.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/11/Catabolism_schematic.svg/220px-Catabolism_schematic.svg.png" decoding="async" width="220" height="202" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/11/Catabolism_schematic.svg/330px-Catabolism_schematic.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/11/Catabolism_schematic.svg/440px-Catabolism_schematic.svg.png 2x" data-file-width="425" data-file-height="390" /></a><figcaption>A simplified outline of redox <a href="/wiki/Metabolism" title="Metabolism">metabolism</a>, showing how NAD+ and NADH link the <a href="/wiki/Citric_acid_cycle" title="Citric acid cycle">citric acid cycle</a> and <a href="/wiki/Oxidative_phosphorylation" title="Oxidative phosphorylation">oxidative phosphorylation</a>[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">image reference needed</a>]</figcaption></figure> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Further information: <a href="/wiki/Cellular_respiration" title="Cellular respiration">Cellular respiration</a> and <a href="/wiki/Oxidative_phosphorylation" title="Oxidative phosphorylation">Oxidative phosphorylation</a></div> The redox reactions catalyzed by oxidoreductases are vital in all parts of metabolism, but one particularly important area where these reactions occur is in the release of energy from nutrients. Here, reduced compounds such as <a href="/wiki/Glucose" title="Glucose">glucose</a> and <a href="/wiki/Fatty_acid" title="Fatty acid">fatty acids</a> are oxidized, thereby releasing energy. This energy is transferred to NAD+ by reduction to NADH, as part of <a href="/wiki/Beta_oxidation" title="Beta oxidation">beta oxidation</a>, <a href="/wiki/Glycolysis" title="Glycolysis">glycolysis</a>, and the <a href="/wiki/Citric_acid_cycle" title="Citric acid cycle">citric acid cycle</a>. In <a href="/wiki/Eukaryote" title="Eukaryote">eukaryotes</a> the electrons carried by the NADH that is produced in the <a href="/wiki/Cytoplasm" title="Cytoplasm">cytoplasm</a> are transferred into the <a href="/wiki/Mitochondrion" title="Mitochondrion">mitochondrion</a> (to reduce mitochondrial NAD+) by <a href="/wiki/Mitochondrial_shuttle" title="Mitochondrial shuttle">mitochondrial shuttles</a>, such as the <a href="/wiki/Malate-aspartate_shuttle" class="mw-redirect" title="Malate-aspartate shuttle">malate-aspartate shuttle</a>.<a href="#cite_note-59">[59]</a> The mitochondrial NADH is then oxidized in turn by the <a href="/wiki/Electron_transport_chain" title="Electron transport chain">electron transport chain</a>, which pumps protons across a membrane and generates ATP through <a href="/wiki/Oxidative_phosphorylation" title="Oxidative phosphorylation">oxidative phosphorylation</a>.<a href="#cite_note-60">[60]</a> These shuttle systems also have the same transport function in <a href="/wiki/Chloroplast" title="Chloroplast">chloroplasts</a>.<a href="#cite_note-61">[61]</a> Since both the oxidized and reduced forms of nicotinamide adenine dinucleotide are used in these linked sets of reactions, the cell maintains significant concentrations of both NAD+ and NADH, with the high NAD+/NADH ratio allowing this coenzyme to act as both an oxidizing and a reducing agent.<a href="#cite_note-Nicholls-62">[62]</a> In contrast, the main function of NADPH is as a reducing agent in <a href="/wiki/Anabolism" title="Anabolism">anabolism</a>, with this coenzyme being involved in pathways such as <a href="/wiki/Fatty_acid_synthesis" title="Fatty acid synthesis">fatty acid synthesis</a> and <a href="/wiki/Photosynthesis" title="Photosynthesis">photosynthesis</a>. Since NADPH is needed to drive redox reactions as a strong reducing agent, the NADP+/NADPH ratio is kept very low.<a href="#cite_note-Nicholls-62">[62]</a> Although it is important in catabolism, NADH is also used in anabolic reactions, such as <a href="/wiki/Gluconeogenesis" title="Gluconeogenesis">gluconeogenesis</a>.<a href="#cite_note-63">[63]</a> This need for NADH in anabolism poses a problem for prokaryotes growing on nutrients that release only a small amount of energy. For example, <a href="/wiki/Nitrification" title="Nitrification">nitrifying</a> bacteria such as <a href="/wiki/Nitrobacter" title="Nitrobacter">Nitrobacter</a> oxidize nitrite to nitrate, which releases sufficient energy to pump protons and generate ATP, but not enough to produce NADH directly.<a href="#cite_note-64">[64]</a> As NADH is still needed for anabolic reactions, these bacteria use a <a href="/wiki/Nitrite_oxidoreductase" title="Nitrite oxidoreductase">nitrite oxidoreductase</a> to produce enough <a href="/wiki/Chemiosmosis" title="Chemiosmosis">proton-motive force</a> to run part of the electron transport chain in reverse, generating NADH.<a href="#cite_note-65">[65]</a> <div class="mw-heading mw-heading3"><h3 id="Non-redox_roles">Non-redox roles</h3>[<a href="/w/index.php?title=Nicotinamide_adenine_dinucleotide&action=edit&section=9" title="Edit section: Non-redox roles">edit</a>]</div> The coenzyme NAD+ is also consumed in ADP-ribose transfer reactions. For example, enzymes called <a href="/wiki/Glycosyltransferase" title="Glycosyltransferase">ADP-ribosyltransferases</a> add the ADP-ribose moiety of this molecule to proteins, in a <a href="/wiki/Posttranslational_modification" class="mw-redirect" title="Posttranslational modification">posttranslational modification</a> called <a href="/wiki/ADP-ribosylation" title="ADP-ribosylation">ADP-ribosylation</a>.<a href="#cite_note-66">[66]</a> ADP-ribosylation involves either the addition of a single ADP-ribose moiety, in mono-ADP-ribosylation, or the transferral of ADP-ribose to proteins in long branched chains, which is called poly(ADP-ribosyl)ation.<a href="#cite_note-Diefenbach-67">[67]</a> Mono-ADP-ribosylation was first identified as the mechanism of a group of bacterial <a href="/wiki/Toxin" title="Toxin">toxins</a>, notably <a href="/wiki/Cholera_toxin" title="Cholera toxin">cholera toxin</a>, but it is also involved in normal <a href="/wiki/Cell_signaling" title="Cell signaling">cell signaling</a>.<a href="#cite_note-68">[68]</a><a href="#cite_note-69">[69]</a> Poly(ADP-ribosyl)ation is carried out by the <a href="/wiki/Poly_ADP_ribose_polymerase" class="mw-redirect" title="Poly ADP ribose polymerase">poly(ADP-ribose) polymerases</a>.<a href="#cite_note-Diefenbach-67">[67]</a><a href="#cite_note-Burkle-70">[70]</a> The poly(ADP-ribose) structure is involved in the regulation of several cellular events and is most important in the <a href="/wiki/Cell_nucleus" title="Cell nucleus">cell nucleus</a>, in processes such as <a href="/wiki/DNA_repair" title="DNA repair">DNA repair</a> and <a href="/wiki/Telomere" title="Telomere">telomere</a> maintenance.<a href="#cite_note-Burkle-70">[70]</a> In addition to these functions within the cell, a group of <a href="/wiki/Extracellular" class="mw-redirect" title="Extracellular">extracellular</a> ADP-ribosyltransferases has recently been discovered, but their functions remain obscure.<a href="#cite_note-71">[71]</a> NAD+ may also be added onto cellular <a href="/wiki/RNA" title="RNA">RNA</a> as a 5'-terminal modification.<a href="#cite_note-72">[72]</a> <figure class="mw-default-size mw-halign-left skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Cyclic_ADP_ribose.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1a/Cyclic_ADP_ribose.svg/240px-Cyclic_ADP_ribose.svg.png" decoding="async" width="240" height="230" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1a/Cyclic_ADP_ribose.svg/360px-Cyclic_ADP_ribose.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1a/Cyclic_ADP_ribose.svg/480px-Cyclic_ADP_ribose.svg.png 2x" data-file-width="1210" data-file-height="1160" /></a><figcaption>The structure of <a href="/wiki/Cyclic_ADP-ribose" title="Cyclic ADP-ribose">cyclic ADP-ribose</a></figcaption></figure> Another function of this coenzyme in cell signaling is as a precursor of <a href="/wiki/Cyclic_ADP-ribose" title="Cyclic ADP-ribose">cyclic ADP-ribose</a>, which is produced from NAD+ by ADP-ribosyl cyclases, as part of a <a href="/wiki/Second_messenger_system" title="Second messenger system">second messenger system</a>.<a href="#cite_note-73">[73]</a> This molecule acts in <a href="/wiki/Calcium_signaling" title="Calcium signaling">calcium signaling</a> by releasing calcium from intracellular stores.<a href="#cite_note-74">[74]</a> It does this by binding to and opening a class of calcium channels called <a href="/wiki/Ryanodine_receptor" title="Ryanodine receptor">ryanodine receptors</a>, which are located in the membranes of <a href="/wiki/Organelle" title="Organelle">organelles</a>, such as the <a href="/wiki/Endoplasmic_reticulum" title="Endoplasmic reticulum">endoplasmic reticulum</a>, and inducing the activation of the <a href="/wiki/Transcription_factor" title="Transcription factor">transcription factor</a> <a href="/wiki/NFATC3" title="NFATC3">NAFC3</a><a href="#cite_note-75">[75]</a> NAD+ is also consumed by different NAD+-consuming enzymes, such as <a href="/wiki/CD38" title="CD38">CD38</a>, <a href="/wiki/BST1" title="BST1">CD157</a>, <a href="/wiki/Poly_(ADP-ribose)_polymerase" title="Poly (ADP-ribose) polymerase">PARPs</a> and the NAD-dependent <a href="/wiki/Histone_deacetylase" title="Histone deacetylase">deacetylases</a> (<a href="/wiki/Sirtuin" title="Sirtuin">sirtuins</a>,such as <a href="/wiki/Sir2" class="mw-redirect" title="Sir2">Sir2</a>.<a href="#cite_note-76">[76]</a>).<a href="#cite_note-:0-77">[77]</a> These enzymes act by transferring an <a href="/wiki/Acetyl" class="mw-redirect" title="Acetyl">acetyl</a> group from their substrate protein to the ADP-ribose moiety of NAD+; this cleaves the coenzyme and releases nicotinamide and O-acetyl-ADP-ribose. The sirtuins mainly seem to be involved in regulating <a href="/wiki/Transcription_(genetics)" class="mw-redirect" title="Transcription (genetics)">transcription</a> through deacetylating histones and altering <a href="/wiki/Nucleosome" title="Nucleosome">nucleosome</a> structure.<a href="#cite_note-78">[78]</a> However, non-histone proteins can be deacetylated by sirtuins as well. These activities of sirtuins are particularly interesting because of their importance in the regulation of <a href="/wiki/Aging" class="mw-redirect" title="Aging">aging</a>.<a href="#cite_note-79">[79]</a><a href="#cite_note-:1-80">[80]</a> Other NAD-dependent enzymes include bacterial <a href="/wiki/DNA_ligase" title="DNA ligase">DNA ligases</a>, which join two DNA ends by using NAD+ as a substrate to donate an <a href="/wiki/Adenosine_monophosphate" title="Adenosine monophosphate">adenosine monophosphate</a> (AMP) moiety to the 5' phosphate of one DNA end. This intermediate is then attacked by the 3' hydroxyl group of the other DNA end, forming a new <a href="/wiki/Phosphodiester_bond" title="Phosphodiester bond">phosphodiester bond</a>.<a href="#cite_note-81">[81]</a> This contrasts with <a href="/wiki/Eukaryotic" class="mw-redirect" title="Eukaryotic">eukaryotic</a> DNA ligases, which use ATP to form the DNA-AMP intermediate.<a href="#cite_note-82">[82]</a> Li et al. have found that NAD+ directly regulates protein-protein interactions.<a href="#cite_note-Li_2017-83">[83]</a> They also show that one of the causes of age-related decline in DNA repair may be increased binding of the protein <a href="/wiki/KIAA1967" title="KIAA1967">DBC1</a> (Deleted in Breast Cancer 1) to <a href="/wiki/PARP1" title="PARP1">PARP1</a> (poly[ADP–ribose] polymerase 1) as NAD+ levels decline during aging.<a href="#cite_note-Li_2017-83">[83]</a> The decline in cellular concentrations of NAD+ during aging likely contributes to the <a href="/wiki/Ageing" title="Ageing">aging</a> process and to the <a href="/wiki/Pathogenesis" title="Pathogenesis">pathogenesis</a> of the chronic diseases of aging.<a href="#cite_note-84">[84]</a> Thus, the modulation of NAD+ may protect against cancer, radiation, and aging.<a href="#cite_note-Li_2017-83">[83]</a> <div class="mw-heading mw-heading3"><h3 id="Extracellular_actions_of_NAD+">Extracellular actions of NAD+</h3>[<a href="/w/index.php?title=Nicotinamide_adenine_dinucleotide&action=edit&section=10" title="Edit section: Extracellular actions of NAD+">edit</a>]</div> In recent years, NAD+ has also been recognized as an <a href="/wiki/Extracellular" class="mw-redirect" title="Extracellular">extracellular</a> signaling molecule involved in cell-to-cell communication.<a href="#cite_note-Billington-49">[49]</a><a href="#cite_note-Ziegler-85">[85]</a><a href="#cite_note-Koch-Nolte-86">[86]</a> NAD+ is released from <a href="/wiki/Neuron" title="Neuron">neurons</a> in <a href="/wiki/Blood_vessel" title="Blood vessel">blood vessels</a>,<a href="#cite_note-Smyth-48">[48]</a> <a href="/wiki/Urinary_bladder" class="mw-redirect" title="Urinary bladder">urinary bladder</a>,<a href="#cite_note-Smyth-48">[48]</a><a href="#cite_note-Breen-87">[87]</a> <a href="/wiki/Large_intestine" title="Large intestine">large intestine</a>,<a href="#cite_note-Mutafova-Yambolieva-88">[88]</a><a href="#cite_note-Hwang-89">[89]</a> from neurosecretory cells,<a href="#cite_note-Yamboliev-90">[90]</a> and from brain <a href="/wiki/Synaptosome" title="Synaptosome">synaptosomes</a>,<a href="#cite_note-Durnin-91">[91]</a> and is proposed to be a novel <a href="/wiki/Neurotransmitter" title="Neurotransmitter">neurotransmitter</a> that transmits information from <a href="/wiki/Nerve" title="Nerve">nerves</a> to effector cells in <a href="/wiki/Smooth_muscle" title="Smooth muscle">smooth muscle</a> organs.<a href="#cite_note-Mutafova-Yambolieva-88">[88]</a><a href="#cite_note-Hwang-89">[89]</a> In plants, the extracellular nicotinamide adenine dinucleotide induces resistance to pathogen infection and the first extracellular NAD receptor has been identified.<a href="#cite_note-Zhou&Wang-92">[92]</a> Further studies are needed to determine the underlying mechanisms of its extracellular actions and their importance for human health and life processes in other organisms. <div class="mw-heading mw-heading2"><h2 id="Clinical_significance">Clinical significance</h2>[<a href="/w/index.php?title=Nicotinamide_adenine_dinucleotide&action=edit&section=11" title="Edit section: Clinical significance">edit</a>]</div> The enzymes that make and use NAD+ and NADH are important in both <a href="/wiki/Pharmacology" title="Pharmacology">pharmacology</a> and the research into future treatments for disease.<a href="#cite_note-93">[93]</a> <a href="/wiki/Drug_design" title="Drug design">Drug design</a> and drug development exploits NAD+ in three ways: as a direct target of drugs, by designing <a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">enzyme inhibitors</a> or activators based on its structure that change the activity of NAD-dependent enzymes, and by trying to inhibit NAD+ biosynthesis.<a href="#cite_note-94">[94]</a> Because cancer cells utilize increased <a href="/wiki/Glycolysis" title="Glycolysis">glycolysis</a>, and because NAD enhances glycolysis, nicotinamide phosphoribosyltransferase (NAD salvage pathway) is often amplified in cancer cells.<a href="#cite_note-pmid30631755-95">[95]</a><a href="#cite_note-pmid32111066-96">[96]</a> It has been studied for its potential use in the therapy of <a href="/wiki/Neurodegenerative_disease" title="Neurodegenerative disease">neurodegenerative diseases</a> such as <a href="/wiki/Alzheimer%27s" class="mw-redirect" title="Alzheimer's">Alzheimer's</a> and <a href="/wiki/Parkinson%27s_disease" title="Parkinson's disease">Parkinson's disease</a> as well as <a href="/wiki/Multiple_sclerosis" title="Multiple sclerosis">multiple sclerosis</a>.<a href="#cite_note-Belenky-6">[6]</a><a href="#cite_note-:1-80">[80]</a><a href="#cite_note-97">[97]</a><a href="#cite_note-:0-77">[77]</a> A placebo-controlled clinical trial of NADH (which excluded NADH precursors) in people with Parkinson's failed to show any effect.<a href="#cite_note-98">[98]</a> NAD+ is also a direct <a href="/wiki/Drug_target" class="mw-redirect" title="Drug target">target</a> of the drug <a href="/wiki/Isoniazid" title="Isoniazid">isoniazid</a>, which is used in the treatment of <a href="/wiki/Tuberculosis" title="Tuberculosis">tuberculosis</a>, an infection caused by <a href="/wiki/Mycobacterium_tuberculosis" title="Mycobacterium tuberculosis">Mycobacterium tuberculosis</a>. Isoniazid is a <a href="/wiki/Prodrug" title="Prodrug">prodrug</a> and once it has entered the bacteria, it is activated by a <a href="/wiki/Peroxidase" title="Peroxidase">peroxidase</a> enzyme, which oxidizes the compound into a <a href="/wiki/Free_radical" class="mw-redirect" title="Free radical">free radical</a> form.<a href="#cite_note-99">[99]</a> This radical then reacts with NADH, to produce adducts that are very potent inhibitors of the enzymes <a href="/wiki/Enoyl-acyl_carrier_protein_reductase" title="Enoyl-acyl carrier protein reductase">enoyl-acyl carrier protein reductase</a>,<a href="#cite_note-100">[100]</a> and <a href="/wiki/Dihydrofolate_reductase" title="Dihydrofolate reductase">dihydrofolate reductase</a>.<a href="#cite_note-101">[101]</a> Since many oxidoreductases use NAD+ and NADH as substrates, and bind them using a highly conserved structural motif, the idea that inhibitors based on NAD+ could be specific to one enzyme is surprising.<a href="#cite_note-Pankiewicz-102">[102]</a> However, this can be possible: for example, inhibitors based on the compounds <a href="/wiki/Mycophenolic_acid" title="Mycophenolic acid">mycophenolic acid</a> and <a href="/wiki/Tiazofurin" title="Tiazofurin">tiazofurin</a> inhibit <a href="/wiki/IMP_dehydrogenase" class="mw-redirect" title="IMP dehydrogenase">IMP dehydrogenase</a> at the NAD+ binding site. Because of the importance of this enzyme in <a href="/wiki/Purine_metabolism" title="Purine metabolism">purine metabolism</a>, these compounds may be useful as anti-cancer, anti-viral, or <a href="/wiki/Immunosuppressive_drug" title="Immunosuppressive drug">immunosuppressive drugs</a>.<a href="#cite_note-Pankiewicz-102">[102]</a><a href="#cite_note-103">[103]</a> Other drugs are not enzyme inhibitors, but instead activate enzymes involved in NAD+ metabolism. <a href="/wiki/Sirtuin" title="Sirtuin">Sirtuins</a> are a particularly interesting target for such drugs, since activation of these NAD-dependent deacetylases extends lifespan in some animal models.<a href="#cite_note-Kim-104">[104]</a> Compounds such as <a href="/wiki/Resveratrol" title="Resveratrol">resveratrol</a> increase the activity of these enzymes, which may be important in their ability to delay aging in both vertebrate,<a href="#cite_note-105">[105]</a> and invertebrate <a href="/wiki/Model_organism" title="Model organism">model organisms</a>.<a href="#cite_note-106">[106]</a><a href="#cite_note-107">[107]</a> In one experiment, mice given NAD for one week had improved nuclear-mitochrondrial communication.<a href="#cite_note-108">[108]</a> Because of the differences in the <a href="/wiki/Metabolic_pathway" title="Metabolic pathway">metabolic pathways</a> of NAD+ biosynthesis between organisms, such as between bacteria and humans, this area of metabolism is a promising area for the development of new <a href="/wiki/Antibiotic" title="Antibiotic">antibiotics</a>.<a href="#cite_note-109">[109]</a><a href="#cite_note-110">[110]</a> For example, the enzyme <a href="/wiki/Nicotinamidase" title="Nicotinamidase">nicotinamidase</a>, which converts nicotinamide to nicotinic acid, is a target for drug design, as this enzyme is absent in humans but present in yeast and bacteria.<a href="#cite_note-Rongvaux-43">[43]</a> In bacteriology, NAD, sometimes referred to factor V, is used as a supplement to culture media for some <a href="/wiki/Fastidious_organism" title="Fastidious organism">fastidious</a> bacteria.<a href="#cite_note-111">[111]</a> <div class="mw-heading mw-heading2"><h2 id="History">History</h2>[<a href="/w/index.php?title=Nicotinamide_adenine_dinucleotide&action=edit&section=12" title="Edit section: History">edit</a>]</div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:ArthurHarden.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/ff/ArthurHarden.jpg/220px-ArthurHarden.jpg" decoding="async" width="220" height="311" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/f/ff/ArthurHarden.jpg 1.5x" data-file-width="280" data-file-height="396" /></a><figcaption><a href="/wiki/Arthur_Harden" title="Arthur Harden">Arthur Harden</a>, co-discoverer of NAD</figcaption></figure> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Further information: <a href="/wiki/History_of_biochemistry" title="History of biochemistry">History of biochemistry</a></div> The coenzyme NAD+ was first discovered by the British biochemists <a href="/wiki/Arthur_Harden" title="Arthur Harden">Arthur Harden</a> and <a href="/wiki/William_John_Young_(biochemist)" title="William John Young (biochemist)">William John Young</a> in 1906.<a href="#cite_note-112">[112]</a> They noticed that adding boiled and filtered <a href="/wiki/Yeast" title="Yeast">yeast</a> extract greatly accelerated <a href="/wiki/Alcoholic_fermentation" class="mw-redirect" title="Alcoholic fermentation">alcoholic fermentation</a> in unboiled yeast extracts. They called the unidentified factor responsible for this effect a coferment. Through a long and difficult purification from yeast extracts, this heat-stable factor was identified as a <a href="/wiki/Nucleotide" title="Nucleotide">nucleotide</a> sugar phosphate by <a href="/wiki/Hans_von_Euler-Chelpin" title="Hans von Euler-Chelpin">Hans von Euler-Chelpin</a>.<a href="#cite_note-113">[113]</a> In 1936, the German scientist <a href="/wiki/Otto_Heinrich_Warburg" title="Otto Heinrich Warburg">Otto Heinrich Warburg</a> showed the function of the nucleotide coenzyme in hydride transfer and identified the nicotinamide portion as the site of redox reactions.<a href="#cite_note-114">[114]</a> Vitamin precursors of NAD+ were first identified in 1938, when <a href="/wiki/Conrad_Elvehjem" title="Conrad Elvehjem">Conrad Elvehjem</a> showed that liver has an "anti-black tongue" activity in the form of nicotinamide.<a href="#cite_note-115">[115]</a> Then, in 1939, he provided the first strong evidence that niacin is used to synthesize NAD+.<a href="#cite_note-116">[116]</a> In the early 1940s, <a href="/wiki/Arthur_Kornberg" title="Arthur Kornberg">Arthur Kornberg</a> was the first to detect an enzyme in the biosynthetic pathway.<a href="#cite_note-117">[117]</a> In 1949, the American biochemists Morris Friedkin and <a href="/wiki/Albert_L._Lehninger" title="Albert L. Lehninger">Albert L. Lehninger</a> proved that NADH linked metabolic pathways such as the <a href="/wiki/Citric_acid_cycle" title="Citric acid cycle">citric acid cycle</a> with the synthesis of ATP in oxidative phosphorylation.<a href="#cite_note-118">[118]</a> In 1958, Jack Preiss and Philip Handler discovered the intermediates and enzymes involved in the biosynthesis of NAD+;<a href="#cite_note-119">[119]</a><a href="#cite_note-120">[120]</a> salvage synthesis from nicotinic acid is termed the Preiss-Handler pathway. In 2004, <a href="/wiki/Charles_Brenner_(biochemist)" title="Charles Brenner (biochemist)">Charles Brenner</a> and co-workers uncovered the <a href="/wiki/Nicotinamide_riboside" title="Nicotinamide riboside">nicotinamide riboside</a> kinase pathway to NAD+.<a href="#cite_note-Bieganowski,_P,_Brenner,_C_2004_495–502-121">[121]</a> The non-redox roles of NAD(P) were discovered later.<a href="#cite_note-Pollak-5">[5]</a> The first to be identified was the use of NAD+ as the ADP-ribose donor in ADP-ribosylation reactions, observed in the early 1960s.<a href="#cite_note-122">[122]</a> Studies in the 1980s and 1990s revealed the activities of NAD+ and NADP+ metabolites in cell signaling – such as the action of <a href="/wiki/Cyclic_ADP-ribose" title="Cyclic ADP-ribose">cyclic ADP-ribose</a>, which was discovered in 1987.<a href="#cite_note-123">[123]</a> The metabolism of NAD+ remained an area of intense research into the 21st century, with interest heightened after the discovery of the NAD+-dependent protein deacetylases called <a href="/wiki/Sirtuin" title="Sirtuin">sirtuins</a> in 2000, by Shin-ichiro Imai and coworkers in the laboratory of <a href="/wiki/Leonard_P._Guarente" title="Leonard P. Guarente">Leonard P. Guarente</a>.<a href="#cite_note-124">[124]</a> In 2009 Imai proposed the "NAD World" hypothesis that key regulators of aging and longevity in mammals are <a href="/wiki/Sirtuin_1" title="Sirtuin 1">sirtuin 1</a> and the primary NAD+ synthesizing enzyme <a href="/wiki/Nicotinamide_phosphoribosyltransferase" title="Nicotinamide phosphoribosyltransferase">nicotinamide phosphoribosyltransferase</a> (NAMPT).<a href="#cite_note-pmid19130305-125">[125]</a> In 2016 Imai expanded his hypothesis to "NAD World 2.0", which postulates that extracellular NAMPT from <a href="/wiki/Adipose_tissue" title="Adipose tissue">adipose tissue</a> maintains NAD+ in the <a href="/wiki/Hypothalamus" title="Hypothalamus">hypothalamus</a> (the control center) in conjunction with <a href="/wiki/Myokine" title="Myokine">myokines</a> from <a href="/wiki/Skeletal_muscle" title="Skeletal muscle">skeletal muscle</a> cells.<a href="#cite_note-pmid28725474-126">[126]</a> In 2018, Napa Therapeutics was formed to develop drugs against a novel aging-related target based on the research in NAD metabolism conducted in the lab of <a href="/wiki/Eric_Verdin" title="Eric Verdin">Eric Verdin</a>.<a href="#cite_note-127">[127]</a> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2>[<a href="/w/index.php?title=Nicotinamide_adenine_dinucleotide&action=edit&section=13" title="Edit section: See also">edit</a>]</div> <ul><li><a href="/wiki/Enzyme_catalysis" title="Enzyme catalysis">Enzyme catalysis</a></li> <li><a href="/wiki/List_of_EC_numbers_(EC_1)" title="List of EC numbers (EC 1)">List of oxidoreductases</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2>[<a href="/w/index.php?title=Nicotinamide_adenine_dinucleotide&action=edit&section=14" title="Edit section: References">edit</a>]</div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output 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(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.chemspider.com/Chemical-Structure.5682.html">"NAD+ | C21H28N7O14P2 | ChemSpider"</a>. www.chemspider.com.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=www.chemspider.com&rft.atitle=NAD%2B+%7C+C21H28N7O14P2+%7C+ChemSpider&rft_id=http%3A%2F%2Fwww.chemspider.com%2FChemical-Structure.5682.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANicotinamide+adenine+dinucleotide" class="Z3988"> </li> <li id="cite_note-2"><a href="#cite_ref-2">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/Nicotinamide-Adenine-Dinucleotide">"Nicotinamide-Adenine-Dinucleotide"</a>. 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href="https://www.fightaging.org/archives/2018/08/napa-therapeutics-formed-to-develop-drugs-to-influence-nad-metabolism/">"Napa Therapeutics Formed to Develop Drugs to Influence NAD Metabolism"</a>. 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W. H. Freeman. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-7167-4339-2" title="Special:BookSources/978-0-7167-4339-2"><bdi>978-0-7167-4339-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Lehninger+Principles+of+Biochemistry&rft.edition=4th&rft.pub=W.+H.+Freeman&rft.date=2004&rft.isbn=978-0-7167-4339-2&rft.au=Nelson+DL&rft.au=Cox+MM&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Flehningerprincip00lehn_0&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANicotinamide+adenine+dinucleotide" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBugg_T2004" class="citation book cs1">Bugg T (2004). Introduction to Enzyme and Coenzyme Chemistry (2nd ed.). Blackwell Publishing Limited. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4051-1452-3" title="Special:BookSources/978-1-4051-1452-3"><bdi>978-1-4051-1452-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Introduction+to+Enzyme+and+Coenzyme+Chemistry&rft.edition=2nd&rft.pub=Blackwell+Publishing+Limited&rft.date=2004&rft.isbn=978-1-4051-1452-3&rft.au=Bugg+T&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANicotinamide+adenine+dinucleotide" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLee_HC2002" class="citation book cs1">Lee HC (2002). Cyclic ADP-Ribose and NAADP: Structure, Metabolism and Functions. Kluwer Academic Publishers. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4020-7281-9" title="Special:BookSources/978-1-4020-7281-9"><bdi>978-1-4020-7281-9</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Cyclic+ADP-Ribose+and+NAADP%3A+Structure%2C+Metabolism+and+Functions&rft.pub=Kluwer+Academic+Publishers&rft.date=2002&rft.isbn=978-1-4020-7281-9&rft.au=Lee+HC&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANicotinamide+adenine+dinucleotide" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLevineSchuchatSchwartzWenger1997" class="citation web cs1">Levine OS, Schuchat A, Schwartz B, Wenger JD, Elliott J (1997). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20040701215032/http://www.who.int/vaccine_research/documents/en/hinfluenzaeb_surveillance.pdf">"Generic protocol for population-based surveillance of Haemophilus influenzae type B"</a> (PDF). World Health Organization. Centers for Disease Control. p. 13. WHO/VRD/GEN/95.05. Archived from <a rel="nofollow" class="external text" href="https://www.who.int/vaccine_research/documents/en/hinfluenzaeb_surveillance.pdf">the original</a> (PDF) on 1 July 2004.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Generic+protocol+for+population-based+surveillance+of+Haemophilus+influenzae+type+B&rft.pages=13&rft.pub=World+Health+Organization&rft.date=1997&rft.aulast=Levine&rft.aufirst=OS&rft.au=Schuchat%2C+A&rft.au=Schwartz%2C+B&rft.au=Wenger%2C+JD&rft.au=Elliott%2C+J&rft_id=https%3A%2F%2Fwww.who.int%2Fvaccine_research%2Fdocuments%2Fen%2Fhinfluenzaeb_surveillance.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANicotinamide+adenine+dinucleotide" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKimLeeTievesPaul2019" class="citation journal cs1">Kim, Jinhyun; Lee, Sahng Ha; Tieves, Florian; Paul, Caroline E.; Hollmann, Frank; Park, Chan Beum (5 July 2019). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6641943">"Nicotinamide adenine dinucleotide as a photocatalyst"</a>. Science Advances. 5 (7): eaax0501. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2019SciA....5..501K">2019SciA....5..501K</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1126%2Fsciadv.aax0501">10.1126/sciadv.aax0501</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6641943">6641943</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/31334353">31334353</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Science+Advances&rft.atitle=Nicotinamide+adenine+dinucleotide+as+a+photocatalyst&rft.volume=5&rft.issue=7&rft.pages=eaax0501&rft.date=2019-07-05&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6641943%23id-name%3DPMC&rft_id=info%3Apmid%2F31334353&rft_id=info%3Adoi%2F10.1126%2Fsciadv.aax0501&rft_id=info%3Abibcode%2F2019SciA....5..501K&rft.aulast=Kim&rft.aufirst=Jinhyun&rft.au=Lee%2C+Sahng+Ha&rft.au=Tieves%2C+Florian&rft.au=Paul%2C+Caroline+E.&rft.au=Hollmann%2C+Frank&rft.au=Park%2C+Chan+Beum&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6641943&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANicotinamide+adenine+dinucleotide" class="Z3988"></li></ul> <div class="mw-heading mw-heading3"><h3 id="History_2">History</h3>[<a href="/w/index.php?title=Nicotinamide_adenine_dinucleotide&action=edit&section=17" title="Edit section: History">edit</a>]</div> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCornish-Bowden1997" class="citation book cs1"><a href="/wiki/Athel_Cornish-Bowden" title="Athel Cornish-Bowden">Cornish-Bowden, Athel</a> (1997). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20101213084345/http://bip.cnrs-mrs.fr/bip10/buchner.htm">New Beer in an Old Bottle. Eduard Buchner and the Growth of Biochemical Knowledge</a>. Valencia: Universitat de Valencia. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-84-370-3328-0" title="Special:BookSources/978-84-370-3328-0"><bdi>978-84-370-3328-0</bdi></a>. Archived from <a rel="nofollow" class="external text" href="http://bip.cnrs-mrs.fr/bip10/buchner.htm">the original</a> on 13 December 2010. Retrieved 8 December 2007.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=New+Beer+in+an+Old+Bottle.+Eduard+Buchner+and+the+Growth+of+Biochemical+Knowledge.&rft.place=Valencia&rft.pub=Universitat+de+Valencia&rft.date=1997&rft.isbn=978-84-370-3328-0&rft.aulast=Cornish-Bowden&rft.aufirst=Athel&rft_id=http%3A%2F%2Fbip.cnrs-mrs.fr%2Fbip10%2Fbuchner.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANicotinamide+adenine+dinucleotide" class="Z3988">, A history of early enzymology.</li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWilliams,_Henry_Smith1904" class="citation book cs1">Williams, Henry Smith (1904). <a rel="nofollow" class="external text" href="http://etext.lib.virginia.edu/toc/modeng/public/Wil4Sci.html">Modern Development of the Chemical and Biological Sciences</a>. A History of Science: in Five Volumes. Vol. IV. New York: Harper and Brothers.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Modern+Development+of+the+Chemical+and+Biological+Sciences&rft.place=New+York&rft.series=A+History+of+Science%3A+in+Five+Volumes&rft.pub=Harper+and+Brothers&rft.date=1904&rft.au=Williams%2C+Henry+Smith&rft_id=http%3A%2F%2Fetext.lib.virginia.edu%2Ftoc%2Fmodeng%2Fpublic%2FWil4Sci.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANicotinamide+adenine+dinucleotide" class="Z3988">, a textbook from the 19th century.</li></ul> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2>[<a href="/w/index.php?title=Nicotinamide_adenine_dinucleotide&action=edit&section=18" title="Edit section: External links">edit</a>]</div> <style data-mw-deduplicate="TemplateStyles:r1235681985">.mw-parser-output .side-box{margin:4px 0;box-sizing:border-box;border:1px solid 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screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .sistersitebox img[src*="Wiktionary-logo-en-v2.svg"]{background-color:white}}</style><div class="side-box side-box-right plainlinks sistersitebox"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"> <div class="side-box-flex"> <div class="side-box-image"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/30px-Commons-logo.svg.png" decoding="async" width="30" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/45px-Commons-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/59px-Commons-logo.svg.png 2x" data-file-width="1024" data-file-height="1376" /></div> <div class="side-box-text plainlist">Wikimedia Commons has media related to <a href="https://commons.wikimedia.org/wiki/Category:Nicotinamide_adenine_dinucleotide" class="extiw" title="commons:Category:Nicotinamide adenine dinucleotide">Nicotinamide adenine dinucleotide</a>.</div></div> </div> <ul><li><a rel="nofollow" class="external text" href="http://www.ebi.ac.uk/pdbe-srv/PDBeXplore/ligand/?ligand=NAD">NAD bound to proteins</a> in the <a href="/wiki/Protein_Data_Bank" title="Protein Data Bank">Protein Data Bank</a></li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20110707060740/http://www.1lecture.com/Biochemistry/How%20the%20NAD%20Works/index.html">NAD Animation</a> (Flash Required)</li> <li><a rel="nofollow" class="external text" href="http://www.sigmaaldrich.com/etc/medialib/docs/Sigma/Product_Information_Sheet/2/n8285pis.Par.0001.File.tmp/n8285pis.pdf">β-Nicotinamide adenine dinucleotide (NAD+, oxidized)</a> and <a rel="nofollow" class="external text" href="http://www.sigmaaldrich.com/etc/medialib/docs/Sigma/Product_Information_Sheet/2/n4505pis.Par.0001.File.tmp/n4505pis.pdf">NADH (reduced)</a> Chemical data sheet from <a href="/wiki/Sigma-Aldrich" title="Sigma-Aldrich">Sigma-Aldrich</a></li> <li><a rel="nofollow" class="external text" href="http://biocyc.org/META/NEW-IMAGE?type=COMPOUND&object=NAD">NAD+</a>, <a rel="nofollow" class="external text" href="http://biocyc.org/META/NEW-IMAGE?type=COMPOUND&object=NADH">NADH</a> and <a rel="nofollow" class="external text" href="http://biocyc.org/META/NEW-IMAGE?type=PATHWAY&object=PWY-3502">NAD synthesis pathway</a> at the <a href="/wiki/MetaCyc" title="MetaCyc">MetaCyc</a> database</li> <li><a rel="nofollow" class="external text" href="http://www.expasy.org/enzyme/1.-.-.-">List of oxidoreductases</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20101130025807/http://www.expasy.org/enzyme/1.-.-.-">Archived</a> 30 November 2010 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a> at the <a href="/wiki/Swiss-Prot" class="mw-redirect" title="Swiss-Prot">SWISS-PROT</a> database</li> <li><a rel="nofollow" class="external text" href="https://en.longevitywiki.org/wiki/NAD+">NAD+</a></li> <li><a rel="nofollow" class="external text" href="https://taheebo-tea.com/blogs/taheebo-tea-research/taheebo-tea-the-molecule-of-youth">NAD+ The Molecule of Youth</a></li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol dl,.mw-parser-output .hlist ol ol,.mw-parser-output .hlist ol ul,.mw-parser-output .hlist ul dl,.mw-parser-output .hlist ul ol,.mw-parser-output .hlist ul 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cofactors"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Enzyme_cofactors" style="font-size:114%;margin:0 4em"><a href="/wiki/Enzyme" title="Enzyme">Enzyme</a> <a href="/wiki/Cofactor_(biochemistry)" title="Cofactor (biochemistry)">cofactors</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Active forms</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Vitamin" title="Vitamin">vitamins</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/Thiamine_pyrophosphate" title="Thiamine pyrophosphate">TPP / ThDP</a> (B1)</li> <li><a href="/wiki/Flavin_mononucleotide" title="Flavin mononucleotide">FMN</a>, <a href="/wiki/Flavin_adenine_dinucleotide" title="Flavin adenine dinucleotide">FAD</a> (B2)</li> <li><a class="mw-selflink selflink">NAD+</a>, <a class="mw-selflink selflink">NADH</a>, <a href="/wiki/Nicotinamide_adenine_dinucleotide_phosphate" title="Nicotinamide adenine dinucleotide phosphate">NADP+</a>, <a href="/wiki/Nicotinamide_adenine_dinucleotide_phosphate" title="Nicotinamide adenine dinucleotide phosphate">NADPH</a> (B3)</li> <li><a href="/wiki/Coenzyme_A" title="Coenzyme A">Coenzyme A</a> (B5)</li> <li><a href="/wiki/Pyridoxal_phosphate" title="Pyridoxal phosphate">PLP / P5P</a> (B6)</li> <li><a href="/wiki/Biotin" title="Biotin">Biotin</a> (B7)</li> <li><a href="/wiki/Tetrahydrofolic_acid" title="Tetrahydrofolic acid">THFA / H4FA</a>, <a href="/wiki/Dihydrofolic_acid" title="Dihydrofolic acid">DHFA / H2FA</a>, <a href="/wiki/5,10-Methylenetetrahydrofolate" title="5,10-Methylenetetrahydrofolate">MTHF</a> (B9)</li> <li><a href="/wiki/Adenosylcobalamin" title="Adenosylcobalamin">AdoCbl</a>, <a href="/wiki/Methylcobalamin" title="Methylcobalamin">MeCbl</a> (B12)</li> <li><a href="/wiki/Vitamin_C" title="Vitamin C">Ascorbic acid</a> (C)</li> <li><a href="/wiki/Phytomenadione" title="Phytomenadione">Phylloquinone</a> (K1), <a href="/wiki/Vitamin_K" title="Vitamin K">Menaquinone</a> (K2)</li> <li><a href="/wiki/Coenzyme_F420" title="Coenzyme F420">Coenzyme F420</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cofactor_(biochemistry)#Non-vitamins" title="Cofactor (biochemistry)">non-vitamins</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_triphosphate" title="Adenosine triphosphate">ATP</a></li> <li><a href="/wiki/Cytidine_triphosphate" title="Cytidine triphosphate">CTP</a></li> <li><a href="/wiki/S-Adenosyl_methionine" title="S-Adenosyl methionine">SAMe</a></li> <li><a href="/wiki/3%27-Phosphoadenosine-5%27-phosphosulfate" title="3'-Phosphoadenosine-5'-phosphosulfate">PAPS</a></li> <li><a href="/wiki/Glutathione" title="Glutathione">GSH</a></li> <li><a href="/wiki/Coenzyme_B" title="Coenzyme B">Coenzyme B</a></li> <li><a href="/wiki/Cofactor_F430" title="Cofactor F430">Cofactor F430</a></li> <li><a href="/wiki/Coenzyme_M" title="Coenzyme M">Coenzyme M</a></li> <li><a href="/wiki/Coenzyme_Q10" title="Coenzyme Q10">Coenzyme Q</a></li> <li><a href="/wiki/Heme" title="Heme">Heme / Haem</a> (<a href="/wiki/Heme_A" title="Heme A">A</a>, <a href="/wiki/Heme_B" title="Heme B">B</a>, <a href="/wiki/Heme_C" title="Heme C">C</a>, <a href="/wiki/Heme_O" title="Heme O">O</a>)</li> <li><a href="/wiki/Lipoic_acid" title="Lipoic acid">Lipoic Acid</a></li> <li><a href="/wiki/Methanofuran" title="Methanofuran">Methanofuran</a></li> <li><a href="/wiki/Molybdopterin" title="Molybdopterin">Molybdopterin</a></li> <li><a href="/wiki/Mycofactocin" title="Mycofactocin">Mycofactocin</a></li> <li><a href="/wiki/Pyrroloquinoline_quinone" title="Pyrroloquinoline quinone">PQQ</a></li> <li><a href="/wiki/Tetrahydrobiopterin" title="Tetrahydrobiopterin">THB / BH4</a></li> <li><a href="/wiki/Tetrahydromethanopterin" title="Tetrahydromethanopterin">THMPT / H4MPT</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Mineral_(nutrient)" title="Mineral (nutrient)">metal ions</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/Calcium" title="Calcium">Ca2+</a></li> <li><a href="/wiki/Copper" title="Copper">Cu2+</a></li> <li><a href="/wiki/Iron" title="Iron">Fe2+, Fe3+</a></li> <li><a href="/wiki/Magnesium" title="Magnesium">Mg2+</a></li> <li><a href="/wiki/Manganese" title="Manganese">Mn2+</a></li> <li><a href="/wiki/Molybdenum" title="Molybdenum">Mo</a></li> <li><a href="/wiki/Nickel" title="Nickel">Ni2+</a></li> <li><a href="/wiki/Zinc" title="Zinc">Zn2+</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Base forms</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/Vitamin" title="Vitamin">vitamins</a>: see <a href="/wiki/Template:Vitamins" title="Template:Vitamins">vitamins</a></li></ul> </div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Nicotinamide_adenine_dinucleotide&oldid=1253979122">https://en.wikipedia.org/w/index.php?title=Nicotinamide_adenine_dinucleotide&oldid=1253979122</a>"</div></div> <div 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