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class="vector-toc-numb">6.1</span> <span>In cancer</span> </div> </a> <ul id="toc-In_cancer-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-As_a_biomarker_of_aging" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#As_a_biomarker_of_aging"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2</span> <span>As a biomarker of aging</span> </div> </a> <ul id="toc-As_a_biomarker_of_aging-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Literature" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Literature"> <div 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Available in 17 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-17" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">17 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/5-%D9%85%D9%8A%D8%AB%D9%8A%D9%84_%D8%B3%D8%A7%D9%8A%D8%AA%D9%88%D8%B3%D9%8A%D9%86" title="5-ميثيل سايتوسين – Arabic" lang="ar" hreflang="ar" data-title="5-ميثيل سايتوسين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%DB%B5-%D9%85%D8%AA%DB%8C%D9%84%E2%80%8C%D8%B3%DB%8C%D8%AA%D9%88%D8%B2%DB%8C%D9%86" title="۵-متیل‌سیتوزین – South Azerbaijani" lang="azb" hreflang="azb" data-title="۵-متیل‌سیتوزین" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/5-methylcytosin" title="5-methylcytosin – Czech" lang="cs" hreflang="cs" data-title="5-methylcytosin" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/5-Methylcytosin" title="5-Methylcytosin – German" lang="de" hreflang="de" data-title="5-Methylcytosin" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%DB%B5-%D9%85%D8%AA%DB%8C%D9%84%E2%80%8C%D8%B3%DB%8C%D8%AA%D9%88%D8%B2%DB%8C%D9%86" title="۵-متیل‌سیتوزین – Persian" lang="fa" hreflang="fa" data-title="۵-متیل‌سیتوزین" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/5-M%C3%A9thylcytosine" title="5-Méthylcytosine – French" lang="fr" hreflang="fr" data-title="5-Méthylcytosine" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/5-Metilcitosina" title="5-Metilcitosina – Galician" lang="gl" hreflang="gl" data-title="5-Metilcitosina" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/5-%EB%A9%94%ED%8B%B8%EC%82%AC%EC%9D%B4%ED%86%A0%EC%8B%A0" title="5-메틸사이토신 – Korean" lang="ko" hreflang="ko" data-title="5-메틸사이토신" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/5-metilcitosina" title="5-metilcitosina – Italian" lang="it" hreflang="it" data-title="5-metilcitosina" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/5-%E3%83%A1%E3%83%81%E3%83%AB%E3%82%B7%E3%83%88%E3%82%B7%E3%83%B3" title="5-メチルシトシン – Japanese" lang="ja" hreflang="ja" data-title="5-メチルシトシン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/5-Metilcitosina" title="5-Metilcitosina – Portuguese" lang="pt" hreflang="pt" data-title="5-Metilcitosina" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/5-Metilcitozin" title="5-Metilcitozin – Serbian" lang="sr" hreflang="sr" data-title="5-Metilcitozin" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/5-Metilcitozin" title="5-Metilcitozin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="5-Metilcitozin" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/5-metilsitozin" title="5-metilsitozin – Turkish" lang="tr" hreflang="tr" data-title="5-metilsitozin" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/5-%D0%9C%D0%B5%D1%82%D0%B8%D0%BB%D1%86%D0%B8%D1%82%D0%BE%D0%B7%D0%B8%D0%BD" title="5-Метилцитозин – Ukrainian" lang="uk" hreflang="uk" data-title="5-Метилцитозин" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li 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data-unpinned-container-id="vector-appearance-unpinned-container" > <div class="vector-pinnable-header-label">Appearance</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-appearance.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-appearance.unpin">hide</button> </div> </div> </div> </nav> </div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound which is a modified DNA base</div> <p> <style data-mw-deduplicate="TemplateStyles:r1084375498">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> </p> <table class="infobox ib-chembox"> <caption>5-Methylcytosine </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:5-Methylcytosine.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3a/5-Methylcytosine.svg/220px-5-Methylcytosine.svg.png" decoding="async" width="220" height="193" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3a/5-Methylcytosine.svg/330px-5-Methylcytosine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3a/5-Methylcytosine.svg/440px-5-Methylcytosine.svg.png 2x" data-file-width="620" data-file-height="543" /></a></span> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">4-Amino-5-methylpyrimidin-2(1<i>H</i>)-one</div></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=554-01-8">554-01-8</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=O%3DC1%2FN%3DC%5CC%28%3DC%28%5CN%29N1%29C">Interactive image</a></span></li><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=Cc1cnc%28%3DO%29%5BnH%5Dc1N">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td>3DMet </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.3dmet.dna.affrc.go.jp"><a rel="nofollow" class="external text" href="http://www.3dmet.dna.affrc.go.jp/cgi/show_data.php?acc=B00435">B00435</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Beilstein_database" title="Beilstein database">Beilstein Reference</a></div> </td> <td>120387 </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=27551">CHEBI:27551</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.58551.html">58551</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.008.236">100.008.236</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q238563#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><a href="/wiki/European_Community_number" title="European Community number"><span title="European Community number (chemical identifier)">EC Number</span></a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>209-058-3</li></ul></div> </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C02376">C02376</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Medical_Subject_Headings" title="Medical Subject Headings">MeSH</a> </td> <td><span title="www.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://www.nlm.nih.gov/cgi/mesh/2014/MB_cgi?mode=&term=5-Methylcytosine">5-Methylcytosine</a></span> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/65040">65040</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/6R795CQT4H">6R795CQT4H</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID50203948">DTXSID50203948</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q238563#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C5H7N3O/c1-3-2-7-5(9)8-4(3)6/h2H,1H3,(H3,6,7,8,9)<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: LRSASMSXMSNRBT-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></div></li><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/C5H7N3O/c1-3-2-7-5(9)8-4(3)6/h2H,1H3,(H3,6,7,8,9)</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: LRSASMSXMSNRBT-UHFFFAOYAO</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%;">O=C1/N=C\C(=C(\N)N1)C</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%;">Cc1cnc(=O)[nH]c1N</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>5</sub><span title="Hydrogen">H</span><sub>7</sub><span title="Nitrogen">N</span><sub>3</sub><span title="Oxygen">O</span> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002125131000000000♠"></span>125.131</span> g·mol<sup>−1</sup>   </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/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals" title="Globally Harmonized System of Classification and Labelling of Chemicals"><b>GHS</b> labelling</a>: </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_pictograms" title="GHS hazard pictograms">Pictograms</a></div> </td> <td><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-exclam.svg" class="mw-file-description" title="GHS07: Exclamation mark"><img alt="GHS07: Exclamation mark" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/50px-GHS-pictogram-exclam.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/75px-GHS-pictogram-exclam.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/100px-GHS-pictogram-exclam.svg.png 2x" data-file-width="512" data-file-height="512" /></a></span> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals#Signal_word" title="Globally Harmonized System of Classification and Labelling of Chemicals">Signal word</a></div> </td> <td><b>Warning</b> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_statements" title="GHS hazard statements">Hazard statements</a></div> </td> <td><abbr class="abbr" title="H317: May cause an allergic skin reaction">H317</abbr>, <abbr class="abbr" title="H319: Causes serious eye irritation">H319</abbr> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_precautionary_statements" title="GHS precautionary statements">Precautionary statements</a></div> </td> <td><abbr class="abbr" title="P261: Avoid breathing dust/fume/gas/mist/vapours/spray.">P261</abbr>, <abbr class="abbr" title="P264: Wash ... thoroughly after handling.">P264</abbr>, <abbr class="abbr" title="P272: Contaminated work clothing should not be allowed out of the workplace.">P272</abbr>, <abbr class="abbr" title="P280: Wear protective gloves/protective clothing/eye protection/face protection.">P280</abbr>, <abbr class="abbr" title="P302+P352: IF ON SKIN: Wash with soap and water.">P302+P352</abbr>, <abbr class="abbr" title="P305+P351+P338: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.">P305+P351+P338</abbr>, <abbr class="abbr" title="P321: Specific treatment (see ... on this label).">P321</abbr>, <abbr class="abbr" title="P333+P313: If skin irritation or a rash occurs: Get medical advice/attention.">P333+P313</abbr>, <abbr class="abbr" title="P337+P313: If eye irritation persists: Get medical advice/attention.">P337+P313</abbr>, <abbr class="abbr" title="P363: Wash contaminated clothing before reuse.">P363</abbr>, <abbr class="abbr" title="P501: Dispose of contents/container to ...">P501</abbr> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/12px-Yes_check.svg.png" decoding="async" width="12" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/18px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/24px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=477315520&page2=5-Methylcytosine">verify</a></span> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <sup><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup> ?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>5-Methylcytosine</b> is a <a href="/wiki/Methylation" title="Methylation">methylated</a> form of the <a href="/wiki/DNA" title="DNA">DNA</a> base <a href="/wiki/Cytosine" title="Cytosine">cytosine</a> (C) that regulates gene <a href="/wiki/Transcription_(genetics)" class="mw-redirect" title="Transcription (genetics)">transcription</a> and takes several other biological roles.<sup id="cite_ref-:3_1-0" class="reference"><a href="#cite_note-:3-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> When cytosine is methylated, the DNA maintains the same sequence, but the <a href="/wiki/Gene_expression#DNA_methylation_and_demethylation_in_transcriptional_regulation" title="Gene expression">expression of methylated genes</a> can be altered (the study of this is part of the field of <a href="/wiki/Epigenetics" title="Epigenetics">epigenetics</a>). 5-Methylcytosine is incorporated in the <a href="/wiki/Nucleoside" title="Nucleoside">nucleoside</a> <a href="/wiki/5-Methylcytidine" title="5-Methylcytidine">5-methylcytidine</a>. </p><p>In 5-methylcytosine, a <a href="/wiki/Methyl_group" title="Methyl group">methyl group</a> is attached to the 5th atom in the 6-atom ring, counting counterclockwise from the NH-bonded <a href="/wiki/Nitrogen" title="Nitrogen">nitrogen</a> at the six o'clock position. This methyl group distinguishes 5-methylcytosine from cytosine. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Discovery">Discovery</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=5-Methylcytosine&action=edit&section=1" title="Edit section: Discovery"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>While trying to isolate the bacterial <a href="/wiki/Toxin" title="Toxin">toxin</a> responsible for <a href="/wiki/Tuberculosis" title="Tuberculosis">tuberculosis</a>, W.G. Ruppel isolated a novel <a href="/wiki/Nucleic_acid" title="Nucleic acid">nucleic acid</a> named <a href="/wiki/Tuberculinic_acid" title="Tuberculinic acid">tuberculinic acid</a> in 1898 from <i><a href="/wiki/Mycobacterium_tuberculosis" title="Mycobacterium tuberculosis">Tubercle bacillus</a></i>.<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> The nucleic acid was found to be unusual, in that it contained in addition to <a href="/wiki/Thymine" title="Thymine">thymine</a>, <a href="/wiki/Guanine" title="Guanine">guanine</a> and <a href="/wiki/Cytosine" title="Cytosine">cytosine</a>, a methylated nucleotide. In 1925, <a href="/wiki/Treat_Baldwin_Johnson" title="Treat Baldwin Johnson">Johnson</a> and Coghill successfully detected a minor amount of a methylated cytosine derivative as a product of <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolysis</a> of tuberculinic acid with <a href="/wiki/Sulfuric_acid" title="Sulfuric acid">sulfuric acid</a>.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> This report was severely criticized because their identification was based solely on the optical properties of the crystalline <a href="/wiki/Picrate" title="Picrate">picrate</a>, and other scientists failed to reproduce the same result.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> But its existence was ultimately proven in 1948, when <a href="/wiki/Rollin_Douglas_Hotchkiss" class="mw-redirect" title="Rollin Douglas Hotchkiss">Hotchkiss</a> separated the nucleic acids of <a href="/wiki/DNA" title="DNA">DNA</a> from <a href="/wiki/Calf_(animal)" title="Calf (animal)">calf</a> <a href="/wiki/Thymus" title="Thymus">thymus</a> using <a href="/wiki/Paper_chromatography" title="Paper chromatography">paper chromatography</a>, by which he detected a unique methylated cytosine, quite distinct from conventional cytosine and <a href="/wiki/Uracil" title="Uracil">uracil</a>.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> After seven decades, it turned out that it is also a common feature in different <a href="/wiki/RNA" title="RNA">RNA</a> molecules, although the precise role is uncertain.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="In_vivo"><i>In vivo</i></h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=5-Methylcytosine&action=edit&section=2" title="Edit section: In vivo"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The function of this chemical varies significantly among species:<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <ul><li>In bacteria, 5-methylcytosine can be found at a variety of sites, and is often used as a marker to protect DNA from being cut by native methylation-sensitive <a href="/wiki/Restriction_enzymes" class="mw-redirect" title="Restriction enzymes">restriction enzymes</a>.</li> <li>In plants, 5-methylcytosine occurs at <a href="/wiki/CpG_site" title="CpG site">CpG</a>, CpHpG and CpHpH sequences (where H = A, C or T).</li> <li>In fungi and animals, 5-methylcytosine predominantly occurs at <a href="/wiki/CpG_site" title="CpG site">CpG</a> dinucleotides. Most <a href="/wiki/Eukaryote" title="Eukaryote">eukaryotes</a> methylate only a small percentage of these sites, but 70-80% of CpG cytosines are methylated in <a href="/wiki/Vertebrate" title="Vertebrate">vertebrates</a>. In mammalian cells, clusters of CpG at the 5' ends of genes are termed CpG islands.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> 1% of all mammalian DNA is 5mC.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup></li></ul> <p>While spontaneous <a href="/wiki/Deamination" title="Deamination">deamination</a> of cytosine forms <a href="/wiki/Uracil" title="Uracil">uracil</a>, which is recognized and removed by DNA repair enzymes, deamination of 5-methylcytosine forms <a href="/wiki/Thymine" title="Thymine">thymine</a>. This conversion of a DNA base from cytosine (C) to thymine (T) can result in a <a href="/wiki/Transition_(genetics)" title="Transition (genetics)">transition mutation</a>.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> In addition, active enzymatic deamination of cytosine or 5-methylcytosine by the <a href="/wiki/APOBEC" title="APOBEC">APOBEC</a> family of cytosine deaminases could have beneficial implications on various cellular processes as well as on organismal evolution.<sup id="cite_ref-Chahwan_R,_Wontakal_SN,_and_Roa_S_12-0" class="reference"><a href="#cite_note-Chahwan_R,_Wontakal_SN,_and_Roa_S-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> The implications of deamination on <a href="/wiki/5-hydroxymethylcytosine" class="mw-redirect" title="5-hydroxymethylcytosine">5-hydroxymethylcytosine</a>, on the other hand, remains less understood. </p> <div class="mw-heading mw-heading2"><h2 id="In_vitro"><i>In vitro</i></h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=5-Methylcytosine&action=edit&section=3" title="Edit section: In vitro"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The NH<sub>2</sub> group can be removed (deamination) from 5-methylcytosine to form <a href="/wiki/Thymine" title="Thymine">thymine</a> with use of reagents such as <a href="/wiki/Nitrous_acid" title="Nitrous acid">nitrous acid</a>; cytosine deaminates to uracil (U) under similar conditions.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (March 2024)">citation needed</span></a></i>]</sup> </p> <figure class="mw-halign-none" typeof="mw:File/Thumb"><a href="/wiki/File:Deamination_5-Methylcytosine_to_Thymine.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/ae/Deamination_5-Methylcytosine_to_Thymine.svg/300px-Deamination_5-Methylcytosine_to_Thymine.svg.png" decoding="async" width="300" height="105" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/ae/Deamination_5-Methylcytosine_to_Thymine.svg/450px-Deamination_5-Methylcytosine_to_Thymine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/ae/Deamination_5-Methylcytosine_to_Thymine.svg/600px-Deamination_5-Methylcytosine_to_Thymine.svg.png 2x" data-file-width="620" data-file-height="217" /></a><figcaption>Deamination of 5-methylcytosine to thymine</figcaption></figure> <p>5-methylcytosine is resistant to deamination by <a href="/wiki/Bisulfite" title="Bisulfite">bisulfite</a> treatment, which deaminates cytosine residues. This property is often exploited to analyze DNA cytosine methylation patterns with <a href="/wiki/Bisulfite_sequencing" title="Bisulfite sequencing">bisulfite sequencing</a>.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Addition_and_regulation_with_DNMTs_(Eukaryotes)"><span id="Addition_and_regulation_with_DNMTs_.28Eukaryotes.29"></span>Addition and regulation with DNMTs (Eukaryotes)</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=5-Methylcytosine&action=edit&section=4" title="Edit section: Addition and regulation with DNMTs (Eukaryotes)"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>5mC marks are placed on genomic DNA via <a href="/wiki/DNA_methyltransferase" title="DNA methyltransferase">DNA methyltransferases</a> (DNMTs). There are 5 DNMTs in humans: DNMT1, DNMT2, DNMT3A, DNMT3B, and DNMT3L, and in algae and fungi 3 more are present (DNMT4, DNMT5, and DNMT6).<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> DNMT1 contains the replication foci targeting sequence (RFTS) and the CXXC domain which catalyze the addition of 5mC marks. RFTS directs DNMT1 to loci of DNA replication to assist in the maintenance of 5mC on daughter strands during DNA replication, whereas CXXC contains a <a href="/wiki/Zinc_finger" title="Zinc finger">zinc finger</a> domain for <i>de novo</i> addition of methylation to the DNA.<sup id="cite_ref-:0_15-0" class="reference"><a href="#cite_note-:0-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> DNMT1 was found to be the predominant DNA methyltransferase in all human tissue.<sup id="cite_ref-:1_16-0" class="reference"><a href="#cite_note-:1-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> Primarily, DNMT3A and DNMT3B are responsible for <i>de novo</i> methylation, and DNMT1 maintains the 5mC mark after replication.<sup id="cite_ref-:3_1-1" class="reference"><a href="#cite_note-:3-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> DNMTs can interact with each other to increase methylating capability. For example, 2 DNMT3L can form a complex with 2 DNMT3A to improve interactions with the DNA, facilitating the methylation.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> Changes in the expression of DNMT results in aberrant methylation. Overexpression produces increased methylation, whereas disruption of the enzyme decreased levels of methylation.<sup id="cite_ref-:1_16-1" class="reference"><a href="#cite_note-:1-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:DNMT_reaction_mechanism.tif" class="mw-file-description"><img alt="DNMT reaction mechanism" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2f/DNMT_reaction_mechanism.tif/lossless-page1-595px-DNMT_reaction_mechanism.tif.png" decoding="async" width="595" height="150" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2f/DNMT_reaction_mechanism.tif/lossless-page1-893px-DNMT_reaction_mechanism.tif.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2f/DNMT_reaction_mechanism.tif/lossless-page1-1190px-DNMT_reaction_mechanism.tif.png 2x" data-file-width="2437" data-file-height="614" /></a><figcaption>Addition of methyl group to cytosine</figcaption></figure> <p>The mechanism of the addition is as follows: first a cysteine residue on the DNMT's PCQ motif creates a nucleophillic attack at carbon 6 on the cytosine nucleotide that is to be methylated. <a href="/wiki/S-Adenosyl_methionine" title="S-Adenosyl methionine">S-Adenosylmethionine</a> then donates a methyl group to carbon 5. A base in the DNMT enzyme deprotonates the residual hydrogen on carbon 5 restoring the double bond between carbon 5 and 6 in the ring, producing the 5-methylcytosine base pair.<sup id="cite_ref-:0_15-1" class="reference"><a href="#cite_note-:0-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Demethylation">Demethylation</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=5-Methylcytosine&action=edit&section=5" title="Edit section: Demethylation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>After a cytosine is methylated to 5mC, it can be reversed back to its initial state via multiple mechanisms. Passive DNA demethylation by dilution eliminates the mark gradually through replication by a lack of maintenance by DNMT. In active DNA demethylation, a series of oxidations converts it to <a href="/wiki/5-hydroxymethylcytosine" class="mw-redirect" title="5-hydroxymethylcytosine">5-hydroxymethylcytosine</a> (5hmC), <a href="/wiki/5-Formylcytosine" title="5-Formylcytosine">5-formylcytosine</a> (5fC), and 5-carboxylcytosine (5caC), and the latter two are eventually excised by <a href="/wiki/Thymine-DNA_glycosylase" title="Thymine-DNA glycosylase">thymine DNA glycosylase</a> (TDG), followed by base excision repair (BER) to restore the cytosine.<sup id="cite_ref-:3_1-2" class="reference"><a href="#cite_note-:3-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> TDG knockout produced a 2-fold increase of 5fC without any statistically significant change to levels of 5hmC, indicating 5mC must be iteratively oxidized at least twice before its full demethylation.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> The oxidation occurs through the <a href="/wiki/TET_enzymes" title="TET enzymes">TET</a> (Ten-eleven translocation) family dioxygenases (<a href="/wiki/TET_enzymes" title="TET enzymes">TET enzymes</a>) which can convert 5mC, 5hmC, and 5fC to their oxidized forms. However, the enzyme has the greatest preference for 5mC and the initial reaction rate for 5hmC and 5fC conversions with TET2 are 4.9-7.6 fold slower.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> TET requires Fe(II) as cofactor, and oxygen and <a href="/wiki/%CE%91-ketoglutarate" class="mw-redirect" title="Α-ketoglutarate">α-ketoglutarate</a> (α-KG) as substrates, and the latter substrate is generated from isocitrate by the enzyme <a href="/wiki/Isocitrate_dehydrogenase" title="Isocitrate dehydrogenase">isocitrate dehydrogenase</a> (IDH).<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> Cancer however can produce <a href="/wiki/2-hydroxyglutarate" class="mw-redirect" title="2-hydroxyglutarate">2-hydroxyglutarate</a> (2HG) which competes with α-KG, reducing TET activity, and in turn reducing conversion of 5mC to 5hmC.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Role_in_humans">Role in humans</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=5-Methylcytosine&action=edit&section=6" title="Edit section: Role in humans"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="In_cancer">In cancer</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=5-Methylcytosine&action=edit&section=7" title="Edit section: In cancer"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In cancer, DNA can become both overly methylated, termed <a href="/wiki/Hypermethylation" class="mw-redirect" title="Hypermethylation">hypermethylation</a>, and under-methylated, termed hypomethylation.<sup id="cite_ref-:22_22-0" class="reference"><a href="#cite_note-:22-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> CpG islands overlapping gene promoters are <i>de novo</i> methylated resulting in aberrant inactivation of genes normally associated with growth inhibition of tumors (an example of hypermethylation).<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> Comparing tumor and normal tissue, the former had elevated levels of the methyltransferases DNMT1, DNMT3A, and mostly DNMT3B, all of which are associated with the abnormal levels of 5mC in cancer.<sup id="cite_ref-:1_16-2" class="reference"><a href="#cite_note-:1-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> Repeat sequences in the genome, including satellite DNA, Alu, and long interspersed elements (LINE), are often seen hypomethylated in cancer, resulting in expression of these normally silenced genes, and levels are often significant markers of tumor progression.<sup id="cite_ref-:22_22-1" class="reference"><a href="#cite_note-:22-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> It has been hypothesized that there a connection between the hypermethylation and hypomethylation; over activity of DNA methyltransferases that produce the abnormal <i>de novo</i> 5mC methylation may be compensated by the removal of methylation, a type of epigenetic repair. However, the removal of methylation is inefficient resulting in an overshoot of genome-wide hypomethylation. The contrary may also be possible; over expression of hypomethylation may be silenced by genome-wide hypermethylation.<sup id="cite_ref-:22_22-2" class="reference"><a href="#cite_note-:22-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> Cancer hallmark capabilities are likely acquired through epigenetic changes that alter the 5mC in both the cancer cells and in surrounding tumor-associated stroma within the tumor microenvironment.<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> The anticancer drug <a href="/wiki/Cisplatin" title="Cisplatin">Cisplatin</a> has been reported to react with 5mC.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="As_a_biomarker_of_aging">As a biomarker of aging</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=5-Methylcytosine&action=edit&section=8" title="Edit section: As a biomarker of aging"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>"Epigenetic age" refers to the connection between chronological age and levels of DNA methylation in the genome.<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> Coupling the levels of DNA methylation, in specific sets of CpGs called "clock CpGs", with algorithms that regress the typical levels of collective genome-wide methylation at a given chronological age, allow for epigenetic age prediction. During youth (0–20 years old), changes in DNA methylation occur at a faster rate as development and growth progresses, and the changes begin to slow down at older ages. Multiple epigenetic age estimators exist. Horvath's clock measures a multi-tissue set of 353 CpGs, half of which positively correlate with age, and the other half negatively, to estimate the epigenetic age.<sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> Hannum's clock utilizes adult blood samples to calculate age based on an orthogonal basis of 71 CpGs.<sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> Levine's clock, known as DNAm PhenoAge, depends on 513 CpGs and surpasses the other age estimators in predicting mortality and lifespan, yet displays bias with non-blood tissues.<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> There are reports of age estimators with the methylation state of only one CpG in the gene ELOVL2.<sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> Estimation of age allows for prediction lifespan through expectations of age related conditions that individuals may be subject to based on their 5mC methylation markers.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (March 2024)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=5-Methylcytosine&action=edit&section=9" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-:3-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-:3_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:3_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-:3_1-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFWuZhang2017" class="citation journal cs1">Wu X, Zhang Y (2017-05-30). 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"DNA methylation-based biomarkers and the epigenetic clock theory of ageing". <i>Nature Reviews Genetics</i>. <b>19</b> (6): 371–384. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1038%2Fs41576-018-0004-3">10.1038/s41576-018-0004-3</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/1471-0064">1471-0064</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/29643443">29643443</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:4709691">4709691</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Nature+Reviews+Genetics&rft.atitle=DNA+methylation-based+biomarkers+and+the+epigenetic+clock+theory+of+ageing&rft.volume=19&rft.issue=6&rft.pages=371-384&rft.date=2018-06&rft.issn=1471-0064&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A4709691%23id-name%3DS2CID&rft_id=info%3Apmid%2F29643443&rft_id=info%3Adoi%2F10.1038%2Fs41576-018-0004-3&rft.aulast=Horvath&rft.aufirst=Steve&rft.au=Raj%2C+Kenneth&rfr_id=info%3Asid%2Fen.wikipedia.org%3A5-Methylcytosine" class="Z3988"></span></span> </li> <li id="cite_note-27"><span class="mw-cite-backlink"><b><a href="#cite_ref-27">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHorvath2013" class="citation journal cs1">Horvath S (2013-12-10). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4015143">"DNA methylation age of human tissues and cell types"</a>. <i>Genome Biology</i>. <b>14</b> (10): 3156. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1186%2Fgb-2013-14-10-r115">10.1186/gb-2013-14-10-r115</a></span>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/1474-760X">1474-760X</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4015143">4015143</a></span>. <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/24138928">24138928</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Genome+Biology&rft.atitle=DNA+methylation+age+of+human+tissues+and+cell+types&rft.volume=14&rft.issue=10&rft.pages=3156&rft.date=2013-12-10&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4015143%23id-name%3DPMC&rft.issn=1474-760X&rft_id=info%3Apmid%2F24138928&rft_id=info%3Adoi%2F10.1186%2Fgb-2013-14-10-r115&rft.aulast=Horvath&rft.aufirst=Steve&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4015143&rfr_id=info%3Asid%2Fen.wikipedia.org%3A5-Methylcytosine" class="Z3988"></span><span class="error" style="font-size:0.95em; font-weight:bold; color:"> (Erratum: <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1186%2Fs13059-015-0649-6">10.1186/s13059-015-0649-6</a>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><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/25968125">25968125</a>,  <a rel="nofollow" class="external text" href="http://retractionwatch.com/2015/06/15/high-profile-aging-paper-posts-old-erratum-requested-by-author-more-than-one-year-prior/"><i>Retraction Watch</i></a><span class="noprint">. If the <a href="/wiki/Erratum" title="Erratum">erratum</a> has been checked and does not affect the cited material, please replace <code>{{<a href="/wiki/Template:Erratum" title="Template:Erratum">erratum</a>|...}}</code> with <code>{{<a href="/wiki/Template:Erratum" title="Template:Erratum">erratum</a>|...|checked=yes}}</code>.</span>)</span></span> </li> <li id="cite_note-28"><span class="mw-cite-backlink"><b><a href="#cite_ref-28">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHannumGuinneyZhaoZhang2013" class="citation journal cs1">Hannum G, Guinney J, Zhao L, Zhang L, Hughes G, Sadda S, Klotzle B, Bibikova M, Fan JB, Gao Y, Deconde R (2013-01-24). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3780611">"Genome-wide Methylation Profiles Reveal Quantitative Views of Human Aging Rates"</a>. <i>Molecular Cell</i>. <b>49</b> (2): 359–367. <a 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title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Molecular+Cell&rft.atitle=Genome-wide+Methylation+Profiles+Reveal+Quantitative+Views+of+Human+Aging+Rates&rft.volume=49&rft.issue=2&rft.pages=359-367&rft.date=2013-01-24&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3780611%23id-name%3DPMC&rft.issn=1097-2765&rft_id=info%3Apmid%2F23177740&rft_id=info%3Adoi%2F10.1016%2Fj.molcel.2012.10.016&rft.aulast=Hannum&rft.aufirst=Gregory&rft.au=Guinney%2C+Justin&rft.au=Zhao%2C+Ling&rft.au=Zhang%2C+Li&rft.au=Hughes%2C+Guy&rft.au=Sadda%2C+SriniVas&rft.au=Klotzle%2C+Brandy&rft.au=Bibikova%2C+Marina&rft.au=Fan%2C+Jian-Bing&rft.au=Gao%2C+Yuan&rft.au=Deconde%2C+Rob&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3780611&rfr_id=info%3Asid%2Fen.wikipedia.org%3A5-Methylcytosine" class="Z3988"></span></span> </li> <li id="cite_note-29"><span class="mw-cite-backlink"><b><a href="#cite_ref-29">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLevineLuQuachChen2018" class="citation journal cs1">Levine ME, Lu AT, Quach A, Chen BH, Assimes TL, Bandinelli S, Hou L, Baccarelli AA, Stewart JD, Li Y, Whitsel EA (2018-04-17). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5940111">"An epigenetic biomarker of aging for lifespan and healthspan"</a>. <i>Aging (Albany NY)</i>. <b>10</b> (4): 573–591. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.18632%2Faging.101414">10.18632/aging.101414</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/1945-4589">1945-4589</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5940111">5940111</a></span>. <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/29676998">29676998</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Aging+%28Albany+NY%29&rft.atitle=An+epigenetic+biomarker+of+aging+for+lifespan+and+healthspan&rft.volume=10&rft.issue=4&rft.pages=573-591&rft.date=2018-04-17&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5940111%23id-name%3DPMC&rft.issn=1945-4589&rft_id=info%3Apmid%2F29676998&rft_id=info%3Adoi%2F10.18632%2Faging.101414&rft.aulast=Levine&rft.aufirst=Morgan+E.&rft.au=Lu%2C+Ake+T.&rft.au=Quach%2C+Austin&rft.au=Chen%2C+Brian+H.&rft.au=Assimes%2C+Themistocles+L.&rft.au=Bandinelli%2C+Stefania&rft.au=Hou%2C+Lifang&rft.au=Baccarelli%2C+Andrea+A.&rft.au=Stewart%2C+James+D.&rft.au=Li%2C+Yun&rft.au=Whitsel%2C+Eric+A.&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5940111&rfr_id=info%3Asid%2Fen.wikipedia.org%3A5-Methylcytosine" class="Z3988"></span></span> </li> <li id="cite_note-30"><span class="mw-cite-backlink"><b><a href="#cite_ref-30">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGaragnaniBacaliniPirazziniGori2012" class="citation journal cs1">Garagnani P, Bacalini MG, Pirazzini C, Gori D, Giuliani C, Mari D, Blasio AM, Gentilini D, Vitale G, Collino S, Rezzi S (2012). "Methylation of ELOVL2 gene as a new epigenetic marker of age". <i>Aging Cell</i>. <b>11</b> (6): 1132–1134. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Facel.12005">10.1111/acel.12005</a>. <a href="/wiki/Hdl_(identifier)" class="mw-redirect" title="Hdl (identifier)">hdl</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://hdl.handle.net/11585%2F128353">11585/128353</a></span>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/1474-9726">1474-9726</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/23061750">23061750</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:8775590">8775590</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Aging+Cell&rft.atitle=Methylation+of+ELOVL2+gene+as+a+new+epigenetic+marker+of+age&rft.volume=11&rft.issue=6&rft.pages=1132-1134&rft.date=2012&rft_id=info%3Ahdl%2F11585%2F128353&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A8775590%23id-name%3DS2CID&rft_id=info%3Adoi%2F10.1111%2Facel.12005&rft.issn=1474-9726&rft_id=info%3Apmid%2F23061750&rft.aulast=Garagnani&rft.aufirst=Paolo&rft.au=Bacalini%2C+Maria+G.&rft.au=Pirazzini%2C+Chiara&rft.au=Gori%2C+Davide&rft.au=Giuliani%2C+Cristina&rft.au=Mari%2C+Daniela&rft.au=Blasio%2C+Anna+M.+Di&rft.au=Gentilini%2C+Davide&rft.au=Vitale%2C+Giovanni&rft.au=Collino%2C+Sebastiano&rft.au=Rezzi%2C+Serge&rfr_id=info%3Asid%2Fen.wikipedia.org%3A5-Methylcytosine" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="Literature">Literature</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=5-Methylcytosine&action=edit&section=10" title="Edit section: Literature"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGriffiths,_Anthony_J._F.1999" class="citation book cs1">Griffiths, Anthony J. F. (1999). <i>An Introduction to genetic analysis</i>. San Francisco: W.H. Freeman. Chapter 15: Gene Mutation. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-7167-3520-2" title="Special:BookSources/0-7167-3520-2"><bdi>0-7167-3520-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=An+Introduction+to+genetic+analysis&rft.place=San+Francisco&rft.pages=Chapter+15%3A+Gene+Mutation&rft.pub=W.H.+Freeman&rft.date=1999&rft.isbn=0-7167-3520-2&rft.au=Griffiths%2C+Anthony+J.+F.&rfr_id=info%3Asid%2Fen.wikipedia.org%3A5-Methylcytosine" class="Z3988"></span> (<a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/books/bv.fcgi?call=bv.View..ShowTOC&rid=iga.TOC">available online</a> at the United States <a href="/wiki/National_Center_for_Biotechnology_Information" title="National Center for Biotechnology Information">National Center for Biotechnology Information</a>)</li></ul>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1&useformat=desktop" 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=5-Methylcytosine&oldid=1243586791">https://en.wikipedia.org/w/index.php?title=5-Methylcytosine&oldid=1243586791</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Nucleobases" title="Category:Nucleobases">Nucleobases</a></li><li><a href="/wiki/Category:Pyrimidones" title="Category:Pyrimidones">Pyrimidones</a></li><li><a href="/wiki/Category:Biomarkers" title="Category:Biomarkers">Biomarkers</a></li><li><a href="/wiki/Category:Methyl_compounds" title="Category:Methyl compounds">Methyl compounds</a></li></ul></div><div id="mw-hidden-catlinks" class="mw-hidden-catlinks mw-hidden-cats-hidden">Hidden categories: <ul><li><a href="/wiki/Category:Articles_citing_publications_with_errata" title="Category:Articles citing publications with errata">Articles citing publications with errata</a></li><li><a href="/wiki/Category:Articles_with_short_description" title="Category:Articles with short description">Articles with short description</a></li><li><a href="/wiki/Category:Short_description_is_different_from_Wikidata" title="Category:Short description is different from Wikidata">Short description is different from Wikidata</a></li><li><a href="/wiki/Category:Chemical_articles_with_multiple_compound_IDs" title="Category:Chemical articles with multiple compound IDs">Chemical articles with multiple compound IDs</a></li><li><a href="/wiki/Category:Multiple_chemicals_in_an_infobox_that_need_indexing" title="Category:Multiple chemicals in an infobox that need indexing">Multiple chemicals in an infobox that need indexing</a></li><li><a href="/wiki/Category:ECHA_InfoCard_ID_from_Wikidata" title="Category:ECHA InfoCard ID from Wikidata">ECHA InfoCard ID from Wikidata</a></li><li><a href="/wiki/Category:Chembox_having_GHS_data" title="Category:Chembox having GHS data">Chembox having GHS data</a></li><li><a href="/wiki/Category:Articles_containing_unverified_chemical_infoboxes" title="Category:Articles containing unverified chemical infoboxes">Articles containing unverified chemical infoboxes</a></li><li><a href="/wiki/Category:Short_description_matches_Wikidata" title="Category:Short description matches Wikidata">Short description matches Wikidata</a></li><li><a href="/wiki/Category:All_articles_with_unsourced_statements" title="Category:All articles with unsourced statements">All articles with unsourced statements</a></li><li><a href="/wiki/Category:Articles_with_unsourced_statements_from_March_2024" title="Category:Articles with unsourced statements from March 2024">Articles with unsourced statements from March 2024</a></li></ul></div></div> </div> </main> </div> <div class="mw-footer-container"> <footer id="footer" class="mw-footer" > <ul id="footer-info"> <li id="footer-info-lastmod"> This page was last edited on 2 September 2024, at 08:55<span class="anonymous-show"> (UTC)</span>.</li> <li id="footer-info-copyright">Text is available under the <a href="/wiki/Wikipedia:Text_of_the_Creative_Commons_Attribution-ShareAlike_4.0_International_License" title="Wikipedia:Text of the Creative Commons Attribution-ShareAlike 4.0 International License">Creative Commons Attribution-ShareAlike 4.0 License</a>; additional terms may apply. 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