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data-event-name="pinnable-header.vector-toc.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-toc.unpin">hide</button> </div> <ul class="vector-toc-contents" id="mw-panel-toc-list"> <li id="toc-mw-content-text" class="vector-toc-list-item vector-toc-level-1"> <a href="#" class="vector-toc-link"> <div class="vector-toc-text">(Top)</div> </a> </li> <li id="toc-Function" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Function"> <div class="vector-toc-text"> <span class="vector-toc-numb">1</span> <span>Function</span> </div> </a> <ul id="toc-Function-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Types" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Types"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Types</span> </div> </a> <button aria-controls="toc-Types-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Types subsection</span> </button> <ul id="toc-Types-sublist" class="vector-toc-list"> <li id="toc-Major_hemes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Major_hemes"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>Major hemes</span> </div> </a> <ul id="toc-Major_hemes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other_hemes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Other_hemes"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.2</span> <span>Other hemes</span> </div> </a> <ul id="toc-Other_hemes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Use_of_capital_letters_to_designate_the_type_of_heme" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Use_of_capital_letters_to_designate_the_type_of_heme"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3</span> <span>Use of capital letters to designate the type of heme</span> </div> </a> <ul id="toc-Use_of_capital_letters_to_designate_the_type_of_heme-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Synthesis" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Synthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Synthesis</span> </div> </a> <ul id="toc-Synthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Synthesis_for_food" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Synthesis_for_food"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Synthesis for food</span> </div> </a> <ul id="toc-Synthesis_for_food-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Degradation" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Degradation"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Degradation</span> </div> </a> <ul id="toc-Degradation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-In_health_and_disease" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#In_health_and_disease"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>In health and disease</span> </div> </a> <button aria-controls="toc-In_health_and_disease-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle In health and disease subsection</span> </button> <ul id="toc-In_health_and_disease-sublist" class="vector-toc-list"> <li id="toc-Cancer" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cancer"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1</span> <span>Cancer</span> </div> </a> <ul id="toc-Cancer-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Genes" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Genes"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Genes</span> </div> </a> <ul id="toc-Genes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Notes_and_references" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Notes_and_references"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Notes and references</span> </div> </a> <ul id="toc-Notes_and_references-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" title="Table of Contents" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Heme</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 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" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">47 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/%D9%87%D9%8A%D9%85" title="هيم – Arabic" lang="ar" hreflang="ar" data-title="هيم" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%B9%E0%A6%BF%E0%A6%AE" title="হিম – Bangla" lang="bn" hreflang="bn" data-title="হিম" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-zh-min-nan mw-list-item"><a href="https://zh-min-nan.wikipedia.org/wiki/Heme" title="Heme – Minnan" lang="nan" hreflang="nan" data-title="Heme" data-language-autonym="閩南語 / Bân-lâm-gú" data-language-local-name="Minnan" class="interlanguage-link-target"><span>閩南語 / Bân-lâm-gú</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Hem" title="Hem – Bosnian" lang="bs" hreflang="bs" data-title="Hem" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Grup_hemo" title="Grup hemo – Catalan" lang="ca" hreflang="ca" data-title="Grup hemo" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Hem" title="Hem – Czech" lang="cs" hreflang="cs" data-title="Hem" 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/H%C3%A4me_(Stoffgruppe)" title="Häme (Stoffgruppe) – German" lang="de" hreflang="de" data-title="Häme (Stoffgruppe)" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%91%CE%AF%CE%BC%CE%B7" title="Αίμη – Greek" lang="el" hreflang="el" data-title="Αίμη" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Hemo" title="Hemo – Spanish" lang="es" hreflang="es" data-title="Hemo" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Hemo" title="Hemo – Esperanto" lang="eo" hreflang="eo" data-title="Hemo" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Hemo" title="Hemo – Basque" lang="eu" hreflang="eu" data-title="Hemo" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%87%D9%85" title="هم – Persian" lang="fa" hreflang="fa" data-title="هم" 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/H%C3%A8me" title="Hème – French" lang="fr" hreflang="fr" data-title="Hème" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Haem" title="Haem – Irish" lang="ga" hreflang="ga" data-title="Haem" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Hemo" title="Hemo – Galician" lang="gl" hreflang="gl" data-title="Hemo" 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/%ED%97%B4" title="헴 – Korean" lang="ko" hreflang="ko" data-title="헴" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D5%80%D5%A5%D5%B4" title="Հեմ – Armenian" lang="hy" hreflang="hy" data-title="Հեմ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Hem" title="Hem – Croatian" lang="hr" hreflang="hr" data-title="Hem" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-io mw-list-item"><a href="https://io.wikipedia.org/wiki/Hemeo" title="Hemeo – Ido" lang="io" hreflang="io" data-title="Hemeo" data-language-autonym="Ido" data-language-local-name="Ido" class="interlanguage-link-target"><span>Ido</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Heme" title="Heme – Indonesian" lang="id" hreflang="id" data-title="Heme" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Eme" title="Eme – Italian" lang="it" hreflang="it" data-title="Eme" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%94%D7%9D" title="הם – Hebrew" lang="he" hreflang="he" data-title="הם" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%93%D0%B5%D0%BC%D0%BE%D0%BF%D1%80%D0%BE%D1%82%D0%B5%D0%B8%D0%B4%D1%82%D0%B5%D1%80" title="Гемопротеидтер – Kazakh" lang="kk" hreflang="kk" data-title="Гемопротеидтер" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/H%C4%93ms" title="Hēms – Latvian" lang="lv" hreflang="lv" data-title="Hēms" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Hem" title="Hem – Hungarian" lang="hu" hreflang="hu" data-title="Hem" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%A5%D0%B5%D0%BC" title="Хем – Macedonian" lang="mk" hreflang="mk" data-title="Хем" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Hem" title="Hem – Malay" lang="ms" hreflang="ms" data-title="Hem" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Heemverbinding" title="Heemverbinding – Dutch" lang="nl" hreflang="nl" data-title="Heemverbinding" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%98%E3%83%A0" title="ヘム – Japanese" lang="ja" hreflang="ja" data-title="ヘム" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Hem_(biokjemi)" title="Hem (biokjemi) – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Hem (biokjemi)" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-nn mw-list-item"><a href="https://nn.wikipedia.org/wiki/Heme" title="Heme – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Heme" data-language-autonym="Norsk nynorsk" data-language-local-name="Norwegian Nynorsk" class="interlanguage-link-target"><span>Norsk nynorsk</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Hem_(biochemia)" title="Hem (biochemia) – Polish" lang="pl" hreflang="pl" data-title="Hem (biochemia)" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Hemo" title="Hemo – Portuguese" lang="pt" hreflang="pt" data-title="Hemo" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Hem" title="Hem – Romanian" lang="ro" hreflang="ro" data-title="Hem" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%93%D0%B5%D0%BC_(%D0%B1%D0%B8%D0%BE%D1%85%D0%B8%D0%BC%D0%B8%D1%8F)" title="Гем (биохимия) – Russian" lang="ru" hreflang="ru" data-title="Гем (биохимия)" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Heme" title="Heme – Simple English" lang="en-simple" hreflang="en-simple" data-title="Heme" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Hem_(ch%C3%A9mia)" title="Hem (chémia) – Slovak" lang="sk" hreflang="sk" data-title="Hem (chémia)" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Hem" title="Hem – Slovenian" lang="sl" hreflang="sl" data-title="Hem" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-ckb mw-list-item"><a href="https://ckb.wikipedia.org/wiki/%DA%BE%DB%8C%D9%85" title="ھیم – Central Kurdish" lang="ckb" hreflang="ckb" data-title="ھیم" data-language-autonym="کوردی" data-language-local-name="Central Kurdish" class="interlanguage-link-target"><span>کوردی</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Hem" title="Hem – Serbian" lang="sr" hreflang="sr" data-title="Hem" 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/Hem" title="Hem – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Hem" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Hemi_(kemia)" title="Hemi (kemia) – Finnish" lang="fi" hreflang="fi" data-title="Hemi (kemia)" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Hemgrupp" title="Hemgrupp – Swedish" lang="sv" hreflang="sv" data-title="Hemgrupp" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Hem" title="Hem – Turkish" lang="tr" hreflang="tr" data-title="Hem" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%93%D0%B5%D0%BC_(%D0%B1%D1%96%D0%BE%D1%85%D1%96%D0%BC%D1%96%D1%8F)" title="Гем (біохімія) – Ukrainian" lang="uk" hreflang="uk" data-title="Гем (біохімія)" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Hem" title="Hem – Vietnamese" lang="vi" hreflang="vi" data-title="Hem" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E8%A1%80%E5%9F%BA%E8%B3%AA" title="血基質 – Chinese" lang="zh" hreflang="zh" data-title="血基質" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q189621#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="Namespaces"> <div 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class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical coordination complex of an iron ion chelated to a porphyrin</div> <p class="mw-empty-elt"> </p> <figure class="skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Mboxygenation.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/cd/Mboxygenation.png/420px-Mboxygenation.png" decoding="async" width="420" height="144" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/cd/Mboxygenation.png/630px-Mboxygenation.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/cd/Mboxygenation.png/840px-Mboxygenation.png 2x" data-file-width="4864" data-file-height="1664" /></a><figcaption>Binding of oxygen to a heme prosthetic group</figcaption></figure> <p><b>Heme</b> (<a href="/wiki/American_English" title="American English">American English</a>), or <b>haem</b> (<a href="/wiki/Commonwealth_English" class="mw-redirect" title="Commonwealth English">Commonwealth English</a>, both pronounced /<a href="/wiki/Help:IPA/English" title="Help:IPA/English">hi:m</a>/ <a href="/wiki/Help:Pronunciation_respelling_key" title="Help:Pronunciation respelling key"><i title="English pronunciation respelling"><span style="font-size:90%">HEEM</span></i></a>), is a ring-shaped iron-containing molecular <a href="/wiki/Prosthetic_group" title="Prosthetic group">component of</a> <a href="/wiki/Hemoglobin" title="Hemoglobin">hemoglobin</a>, which is necessary to bind <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> in the <a href="/wiki/Bloodstream" class="mw-redirect" title="Bloodstream">bloodstream</a>. It is composed of four <a href="/wiki/Pyrrole" title="Pyrrole">pyrrole</a> rings with 2 <a href="/wiki/Vinyl_group" title="Vinyl group">vinyl</a> and 2 <a href="/wiki/Propionic_acid" title="Propionic acid">propionic acid</a> side chains.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Heme is <a href="/wiki/Biosynthesized" class="mw-redirect" title="Biosynthesized">biosynthesized</a> in both the <a href="/wiki/Bone_marrow" title="Bone marrow">bone marrow</a> and the <a href="/wiki/Liver" title="Liver">liver</a>.<sup id="cite_ref-bloomer98_2-0" class="reference"><a href="#cite_note-bloomer98-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p>Heme plays a critical role in multiple different <a href="/wiki/Redox" title="Redox">redox</a> reactions in mammals, due to its ability to carry the oxygen molecule. Reactions include <a href="/wiki/Oxidative_metabolism" class="mw-redirect" title="Oxidative metabolism">oxidative metabolism</a> (<a href="/wiki/Cytochrome_c_oxidase" title="Cytochrome c oxidase">cytochrome c oxidase</a>, <a href="/wiki/Succinate_dehydrogenase" title="Succinate dehydrogenase">succinate dehydrogenase</a>), <a href="/wiki/Xenobiotic" title="Xenobiotic">xenobiotic</a> <a href="/wiki/Detoxification" title="Detoxification">detoxification</a> via <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450</a> pathways (including <a href="/wiki/Drug_metabolism" title="Drug metabolism">metabolism</a> of some drugs), gas sensing (<a href="/wiki/Guanylate_cyclase" title="Guanylate cyclase">guanyl cyclases</a>, <a href="/wiki/Nitric_oxide" title="Nitric oxide">nitric oxide</a> synthase), and <a href="/wiki/MicroRNA" title="MicroRNA">microRNA</a> processing (DGCR8).<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> </p><p>Heme is a <a href="/wiki/Coordination_complex" title="Coordination complex">coordination complex</a> "consisting of an iron ion coordinated to a <a href="/wiki/Tetrapyrrole" title="Tetrapyrrole">tetrapyrrole</a> acting as a <a href="/wiki/Tetradentate_ligand" title="Tetradentate ligand">tetradentate ligand</a>, and to one or two axial ligands".<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> The definition is loose, and many depictions omit the axial ligands.<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> Among the metalloporphyrins deployed by <a href="/wiki/Metalloprotein" title="Metalloprotein">metalloproteins</a> as <a href="/wiki/Prosthetic_group" title="Prosthetic group">prosthetic groups</a>, heme is one of the most widely used<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> and defines a family of proteins known as <a href="/wiki/Hemoprotein" title="Hemoprotein">hemoproteins</a>. Hemes are most commonly recognized as components of <a href="/wiki/Hemoglobin" title="Hemoglobin">hemoglobin</a>, the red <a href="/wiki/Pigment" title="Pigment">pigment</a> in <a href="/wiki/Blood" title="Blood">blood</a>, but are also found in a number of other <a href="/wiki/Biologically" class="mw-redirect" title="Biologically">biologically</a> important hemoproteins such as <a href="/wiki/Myoglobin" title="Myoglobin">myoglobin</a>, <a href="/wiki/Cytochrome" title="Cytochrome">cytochromes</a>, <a href="/wiki/Catalase" title="Catalase">catalases</a>, <a href="/wiki/Heme_peroxidase" class="mw-redirect" title="Heme peroxidase">heme peroxidase</a>, and <a href="/wiki/Endothelial_NOS" title="Endothelial NOS">endothelial nitric oxide synthase</a>.<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><sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>The word <i>haem</i> is derived from <a href="/wiki/Ancient_Greek_language" class="mw-redirect" title="Ancient Greek language">Greek</a> <span title="Ancient Greek (to 1453)-language text"><span lang="grc">αἷμα</span></span> <i>haima</i> 'blood'. </p> <div><figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Haem-B-3D-vdW.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/69/Haem-B-3D-vdW.png/200px-Haem-B-3D-vdW.png" decoding="async" width="200" height="207" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/69/Haem-B-3D-vdW.png/300px-Haem-B-3D-vdW.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/69/Haem-B-3D-vdW.png/400px-Haem-B-3D-vdW.png 2x" data-file-width="1100" data-file-height="1140" /></a><figcaption><a href="/wiki/Space-filling_model" title="Space-filling model">Space-filling model</a> of the Fe-<a href="/wiki/Protoporphyrin_IX" title="Protoporphyrin IX">protoporphyrin IX</a> subunit of heme B. Axial ligands omitted. Color scheme: grey=iron, blue=nitrogen, black=carbon, white=hydrogen, red=oxygen</figcaption></figure></div> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Function">Function</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Heme&action=edit&section=1" title="Edit section: Function"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Succinate_Dehygrogenase_1YQ3_Haem_group.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bd/Succinate_Dehygrogenase_1YQ3_Haem_group.png/220px-Succinate_Dehygrogenase_1YQ3_Haem_group.png" decoding="async" width="220" height="220" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bd/Succinate_Dehygrogenase_1YQ3_Haem_group.png/330px-Succinate_Dehygrogenase_1YQ3_Haem_group.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bd/Succinate_Dehygrogenase_1YQ3_Haem_group.png/440px-Succinate_Dehygrogenase_1YQ3_Haem_group.png 2x" data-file-width="1620" data-file-height="1620" /></a><figcaption>The heme group of <a href="/wiki/Succinate_dehydrogenase" title="Succinate dehydrogenase">succinate dehydrogenase</a> bound to <a href="/wiki/Histidine" title="Histidine">histidine</a>, an <a href="/wiki/Electron_carrier" class="mw-redirect" title="Electron carrier">electron carrier</a> in the <a href="/wiki/Mitochondria" class="mw-redirect" title="Mitochondria">mitochondrial</a> <a href="/wiki/Electron_transfer_chain" class="mw-redirect" title="Electron transfer chain">electron transfer chain</a>. The large semi-transparent sphere indicates the location of the <a href="/wiki/Iron" title="Iron">iron</a> <a href="/wiki/Ion" title="Ion">ion</a>. From <span class="plainlinks"><a href="/wiki/Protein_Data_Bank" title="Protein Data Bank">PDB</a>: <a rel="nofollow" class="external text" href="https://www.rcsb.org/structure/1YQ3">1YQ3</a></span>.</figcaption></figure> <p><a href="/wiki/Hemoproteins" class="mw-redirect" title="Hemoproteins">Hemoproteins</a> have diverse biological functions including the transportation of <a href="/wiki/Diatomic" class="mw-redirect" title="Diatomic">diatomic</a> gases, chemical <a href="/wiki/Catalysis" title="Catalysis">catalysis</a>, diatomic gas detection, and <a href="/wiki/Electron_transfer" title="Electron transfer">electron transfer</a>. The heme iron serves as a source or sink of electrons during electron transfer or <a href="/wiki/Redox" title="Redox">redox</a> chemistry. In <a href="/wiki/Peroxidase" title="Peroxidase">peroxidase</a> reactions, the <a href="/wiki/Porphyrin" title="Porphyrin">porphyrin</a> <a href="/wiki/Molecule" title="Molecule">molecule</a> also serves as an electron source, being able to delocalize radical electrons in the conjugated ring. In the transportation or detection of diatomic gases, the gas binds to the heme iron. During the detection of diatomic gases, the binding of the gas <a href="/wiki/Ligand" title="Ligand">ligand</a> to the heme iron induces <a href="/wiki/Conformational_change" title="Conformational change">conformational changes</a> in the surrounding protein.<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> In general, diatomic gases only bind to the reduced heme, as ferrous Fe(II) while most peroxidases cycle between Fe(III) and Fe(IV) and hemeproteins involved in mitochondrial redox, oxidation-reduction, cycle between Fe(II) and Fe(III). </p><p>It has been speculated that the original evolutionary function of <a href="/wiki/Hemoproteins" class="mw-redirect" title="Hemoproteins">hemoproteins</a> was electron transfer in primitive <a href="/wiki/Sulfur" title="Sulfur">sulfur</a>-based <a href="/wiki/Photosynthesis" title="Photosynthesis">photosynthesis</a> pathways in ancestral <a href="/wiki/Cyanobacteria" title="Cyanobacteria">cyanobacteria</a>-like <a href="/wiki/Living_organisms" class="mw-redirect" title="Living organisms">organisms</a> before the appearance of molecular <a href="/wiki/Oxygen" title="Oxygen">oxygen</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> </p><p>Hemoproteins achieve their remarkable functional diversity by modifying the environment of the heme macrocycle within the protein matrix.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> For example, the ability of <a href="/wiki/Hemoglobin" title="Hemoglobin">hemoglobin</a> to effectively deliver <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> to <a href="/wiki/Tissue_(biology)" title="Tissue (biology)">tissues</a> is due to specific <a href="/wiki/Amino_acid" title="Amino acid">amino acid</a> residues located near the heme molecule.<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> Hemoglobin reversibly binds to oxygen in the lungs when the <a href="/wiki/PH" title="PH">pH</a> is high, and the <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a> concentration is low. When the situation is reversed (low pH and high carbon dioxide concentrations), hemoglobin will release oxygen into the tissues. This phenomenon, which states that hemoglobin's oxygen <a href="/wiki/Binding_affinity" class="mw-redirect" title="Binding affinity">binding affinity</a> is <a href="/wiki/Inversely_proportional" class="mw-redirect" title="Inversely proportional">inversely proportional</a> to both <a href="/wiki/Acidity" class="mw-redirect" title="Acidity">acidity</a> and concentration of carbon dioxide, is known as the <a href="/wiki/Bohr_effect" title="Bohr effect">Bohr effect</a>.<sup id="cite_ref-:2_14-0" class="reference"><a href="#cite_note-:2-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> The molecular <a href="/wiki/Chemical_mechanism" class="mw-redirect" title="Chemical mechanism">mechanism</a> behind this effect is the <a href="/wiki/Steric" class="mw-redirect" title="Steric">steric</a> organization of the <a href="/wiki/Globin" title="Globin">globin</a> chain; a <a href="/wiki/Histidine" title="Histidine">histidine</a> residue, located adjacent to the heme group, becomes positively charged under acidic conditions (which are caused by <a href="/wiki/Carbonic_acid" title="Carbonic acid">dissolved CO<sub>2</sub></a> in working muscles, etc.), releasing oxygen from the heme group.<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Types">Types</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Heme&action=edit&section=2" title="Edit section: Types"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Major_hemes">Major hemes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Heme&action=edit&section=3" title="Edit section: Major hemes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>There are several biologically important kinds of heme: </p> <table class="wikitable skin-invert-image"> <tbody><tr> <td colspan="2"> </td> <th><a href="/wiki/Heme_A" title="Heme A">Heme A</a> </th> <th><a href="/wiki/Heme_B" title="Heme B">Heme B</a> </th> <th><a href="/wiki/Heme_C" title="Heme C">Heme C</a> </th> <th><a href="/wiki/Heme_O" title="Heme O">Heme O</a> </th></tr> <tr> <td colspan="2">PubChem number </td> <td><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=7888115">7888115</a> </td> <td><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=444098">444098</a> </td> <td><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=444125">444125</a> </td> <td><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=6323367">6323367</a> </td></tr> <tr> <td colspan="2">Chemical formula </td> <td>C<sub>49</sub>H<sub>56</sub>O<sub>6</sub>N<sub>4</sub>Fe </td> <td>C<sub>34</sub>H<sub>32</sub>O<sub>4</sub>N<sub>4</sub>Fe </td> <td>C<sub>34</sub>H<sub>36</sub>O<sub>4</sub>N<sub>4</sub>S<sub>2</sub>Fe </td> <td>C<sub>49</sub>H<sub>58</sub>O<sub>5</sub>N<sub>4</sub>Fe </td></tr> <tr> <td>Functional group at C<sub>3</sub> </td> <td rowspan="3"><span typeof="mw:File"><a href="/wiki/File:Porphyrin_Numbering.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/25/Porphyrin_Numbering.png/140px-Porphyrin_Numbering.png" decoding="async" width="140" height="148" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/25/Porphyrin_Numbering.png/210px-Porphyrin_Numbering.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/25/Porphyrin_Numbering.png/280px-Porphyrin_Numbering.png 2x" data-file-width="1210" data-file-height="1275" /></a></span> </td> <td>–CH(OH)CH<sub>2</sub><a href="/wiki/Farnesene" title="Farnesene">Far</a> </td> <td><a href="/wiki/Vinyl_group" title="Vinyl group">–CH=CH<sub>2</sub></a> </td> <td>–CH(<a href="/wiki/Cysteine" title="Cysteine">cystein-<i>S</i>-yl</a>)CH<sub>3</sub> </td> <td>–CH(OH)CH<sub>2</sub><a href="/wiki/Farnesene" title="Farnesene">Far</a> </td></tr> <tr> <td>Functional group at C<sub>8</sub> </td> <td>–CH=CH<sub>2</sub> </td> <td>–CH=CH<sub>2</sub> </td> <td>–CH(<a href="/wiki/Cysteine" title="Cysteine">cystein-<i>S</i>-yl</a>)CH<sub>3</sub> </td> <td>–CH=CH<sub>2</sub> </td></tr> <tr> <td>Functional group at C<sub>18</sub> </td> <td><a href="/wiki/Formyl" class="mw-redirect" title="Formyl">–CH=O</a> </td> <td><a href="/wiki/Methyl" class="mw-redirect" title="Methyl">–CH<sub>3</sub></a> </td> <td>–CH<sub>3</sub> </td> <td>–CH<sub>3</sub> </td></tr></tbody></table> <figure class="mw-halign-right skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Heme_b.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/be/Heme_b.svg/200px-Heme_b.svg.png" decoding="async" width="200" height="221" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/be/Heme_b.svg/300px-Heme_b.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/be/Heme_b.svg/400px-Heme_b.svg.png 2x" data-file-width="620" data-file-height="685" /></a><figcaption>Structure of Fe-porphyrin subunit of heme B.</figcaption></figure> <figure class="skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Heme_a.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1b/Heme_a.svg/200px-Heme_a.svg.png" decoding="async" width="200" height="201" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1b/Heme_a.svg/300px-Heme_a.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1b/Heme_a.svg/400px-Heme_a.svg.png 2x" data-file-width="620" data-file-height="623" /></a><figcaption>Structure of Fe-porphyrin subunit of heme A.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> Heme A is synthesized from heme B. In two sequential reactions a 17-hydroxyethylfarnesyl moiety is added at the 2-position and an aldehyde is added at the 8-position.<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></figcaption></figure> <p>The most common type is <i><a href="/wiki/Heme_B" title="Heme B">heme B</a></i>; other important types include <i><a href="/wiki/Heme_A" title="Heme A">heme A</a></i> and <i><a href="/wiki/Heme_C" title="Heme C">heme C</a></i>. Isolated hemes are commonly designated by capital letters while hemes bound to proteins are designated by lower case letters. Cytochrome a refers to the heme A in specific combination with membrane protein forming a portion of <a href="/wiki/Cytochrome_c_oxidase" title="Cytochrome c oxidase">cytochrome c oxidase</a>.<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> </p> <div class="mw-heading mw-heading3"><h3 id="Other_hemes">Other hemes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Heme&action=edit&section=4" title="Edit section: Other hemes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <dl><dd><i>The following carbon numbering system of porphyrins is an older numbering used by biochemists and not the 1–24 numbering system recommended by <a href="/wiki/IUPAC" class="mw-redirect" title="IUPAC">IUPAC</a>, which is shown in the table above.</i></dd></dl> <ul><li><b>Heme <i>l</i></b> is the derivative of heme B which is covalently attached to the protein of <a href="/wiki/Lactoperoxidase" title="Lactoperoxidase">lactoperoxidase</a>, <a href="/wiki/Eosinophil_peroxidase" title="Eosinophil peroxidase">eosinophil peroxidase</a>, and <a href="/wiki/Thyroid_peroxidase" title="Thyroid peroxidase">thyroid peroxidase</a>. The addition of <a href="/wiki/Peroxide" title="Peroxide">peroxide</a> with the <a href="/wiki/Glutamyl" class="mw-redirect" title="Glutamyl">glutamyl</a>-375 and <a href="/wiki/Aspartyl" class="mw-redirect" title="Aspartyl">aspartyl</a>-225 of lactoperoxidase forms ester bonds between these amino acid residues and the heme 1- and 5-methyl groups, respectively.<sup id="cite_ref-pmid9774411_19-0" class="reference"><a href="#cite_note-pmid9774411-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> Similar ester bonds with these two methyl groups are thought to form in eosinophil and thyroid peroxidases. Heme <i>l</i> is one important characteristic of animal peroxidases; plant peroxidases incorporate heme B. Lactoperoxidase and eosinophil peroxidase are protective enzymes responsible for the destruction of invading bacteria and virus. Thyroid peroxidase is the enzyme catalyzing the biosynthesis of the important thyroid hormones. Because lactoperoxidase destroys invading organisms in the lungs and excrement, it is thought to be an important protective enzyme.<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></li> <li><b>Heme <i>m</i></b> is the derivative of heme B covalently bound at the active site of <a href="/wiki/Myeloperoxidase" title="Myeloperoxidase">myeloperoxidase</a>. Heme <i>m</i> contains the two <a href="/wiki/Ester_bond" class="mw-redirect" title="Ester bond">ester bonds</a> at the heme 1- and 5-methyl groups also present in heme <i>l</i> of other mammalian peroxidases, such as lactoperoxidase and eosinophil peroxidase. In addition, a unique <a href="/wiki/Sulfonamides" class="mw-redirect" title="Sulfonamides">sulfonamide</a> ion linkage between the sulfur of a methionyl amino-acid residue and the heme 2-vinyl group is formed, giving this enzyme the unique capability of easily oxidizing <a href="/wiki/Chloride" title="Chloride">chloride</a> and <a href="/wiki/Bromide" title="Bromide">bromide</a> ions to hypochlorite and hypobromite. <a href="/wiki/Myeloperoxidase" title="Myeloperoxidase">Myeloperoxidase</a> is present in mammalian <a href="/wiki/Neutrophil" title="Neutrophil">neutrophils</a> and is responsible for the destruction of invading bacteria and viral agents. It perhaps synthesizes <a href="/wiki/Hypobromite" title="Hypobromite">hypobromite</a> by "mistake". Both hypochlorite and hypobromite are very reactive species responsible for the production of halogenated nucleosides, which are mutagenic compounds.<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><sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup></li> <li><b>Heme D</b> is another derivative of heme B, but in which the <a href="/wiki/Propionic_acid" title="Propionic acid">propionic acid</a> side chain at the carbon of position 6, which is also hydroxylated, forms a γ-<a href="/wiki/Spirolactone" title="Spirolactone">spirolactone</a>. Ring III is also hydroxylated at position 5, in a conformation <i>trans</i> to the new lactone group.<sup id="cite_ref-pmid8621527_23-0" class="reference"><a href="#cite_note-pmid8621527-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> Heme D is the site for oxygen reduction to water of many types of bacteria at low oxygen tension.<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></li> <li><b>Heme S</b> is related to heme B by having a <a href="/wiki/Formaldehyde" title="Formaldehyde">formyl</a> group at position 2 in place of the 2-vinyl group. Heme S is found in the hemoglobin of a few species of marine worms. The correct structures of heme B and heme S were first elucidated by German chemist <a href="/wiki/Hans_Fischer" title="Hans Fischer">Hans Fischer</a>.<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></li></ul> <p>The names of <a href="/wiki/Cytochrome" title="Cytochrome">cytochromes</a> typically (but not always) reflect the kinds of hemes they contain: cytochrome a contains heme A, cytochrome c contains heme C, etc. This convention may have been first introduced with the publication of the structure of <a href="/wiki/Heme_A" title="Heme A">heme A</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Use_of_capital_letters_to_designate_the_type_of_heme">Use of capital letters to designate the type of heme</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Heme&action=edit&section=5" title="Edit section: Use of capital letters to designate the type of heme"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The practice of designating hemes with upper case letters was formalized in a footnote in a paper by Puustinen and Wikstrom,<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> which explains under which conditions a capital letter should be used: "we prefer the use of capital letters to describe the heme structure as isolated. Lowercase letters may then be freely used for cytochromes and enzymes, as well as to describe individual protein-bound heme groups (for example, cytochrome bc, and aa3 complexes, cytochrome b<sub>5</sub>, heme c<sub>1</sub> of the bc<sub>1</sub> complex, heme a<sub>3</sub> of the aa<sub>3</sub> complex, etc)." In other words, the chemical compound would be designated with a capital letter, but specific instances in structures with lowercase. Thus cytochrome oxidase, which has two A hemes (heme a and heme a<sub>3</sub>) in its structure, contains two moles of heme A per mole protein. Cytochrome bc<sub>1</sub>, with hemes b<sub>H</sub>, b<sub>L</sub>, and c<sub>1</sub>, contains heme B and heme C in a 2:1 ratio. The practice seems to have originated in a paper by Caughey and York in which the product of a new isolation procedure for the heme of cytochrome aa3 was designated heme A to differentiate it from previous preparations: "Our product is not identical in all respects with the heme a obtained in solution by other workers by the reduction of the hemin a as isolated previously (2). For this reason, we shall designate our product heme A until the apparent differences can be rationalized."<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> In a later paper,<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> Caughey's group uses capital letters for isolated heme B and C as well as A. </p> <div class="mw-heading mw-heading2"><h2 id="Synthesis">Synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Heme&action=edit&section=6" title="Edit section: Synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Porphyrin#Biosynthesis" title="Porphyrin">Porphyrin § Biosynthesis</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/Cobalamin_biosynthesis" title="Cobalamin biosynthesis">Cobalamin biosynthesis</a></div> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Heme_synthesis.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/Heme_synthesis.svg/660px-Heme_synthesis.svg.png" decoding="async" width="660" height="333" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/Heme_synthesis.svg/990px-Heme_synthesis.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/Heme_synthesis.svg/1320px-Heme_synthesis.svg.png 2x" data-file-width="551" data-file-height="278" /></a><figcaption>Heme synthesis in the <a href="/wiki/Cytoplasm" title="Cytoplasm">cytoplasm</a> and <a href="/wiki/Mitochondrion" title="Mitochondrion">mitochondrion</a></figcaption></figure> <p>The enzymatic process that produces heme is properly called <a href="/wiki/Porphyrin" title="Porphyrin">porphyrin</a> synthesis, as all the intermediates are <a href="/wiki/Pyrrole" title="Pyrrole">tetrapyrroles</a> that are chemically classified as porphyrins. The process is highly conserved across biology. In humans, this pathway serves almost exclusively to form heme. In <a href="/wiki/Bacteria" title="Bacteria">bacteria</a>, it also produces more complex substances such as <a href="/wiki/Cofactor_F430" title="Cofactor F430">cofactor F430</a> and <a href="/wiki/Cobalamin" class="mw-redirect" title="Cobalamin">cobalamin</a> (<a href="/wiki/Vitamin_B12" title="Vitamin B12">vitamin B<sub>12</sub></a>).<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> </p><p>The pathway is initiated by the synthesis of <a href="/wiki/%CE%94-aminolevulinic_acid" class="mw-redirect" title="Δ-aminolevulinic acid">δ-aminolevulinic acid</a> (dALA or δALA) from the <a href="/wiki/Amino_acid" title="Amino acid">amino acid</a> <a href="/wiki/Glycine" title="Glycine">glycine</a> and <a href="/wiki/Succinyl-CoA" title="Succinyl-CoA">succinyl-CoA</a> from the <a href="/wiki/Citric_acid_cycle" title="Citric acid cycle">citric acid cycle</a> (Krebs cycle). The rate-limiting enzyme responsible for this reaction, <i>ALA synthase</i>, is negatively regulated by glucose and heme concentration. Mechanism of inhibition of ALAs by heme or hemin is by decreasing stability of mRNA synthesis and by decreasing the intake of mRNA in the mitochondria. This mechanism is of therapeutic importance: infusion of <i>heme arginate</i> or <i>hematin</i> and glucose can abort attacks of <a href="/wiki/Acute_intermittent_porphyria" title="Acute intermittent porphyria">acute intermittent porphyria</a> in patients with an <a href="/wiki/Inborn_error_of_metabolism" class="mw-redirect" title="Inborn error of metabolism">inborn error of metabolism</a> of this process, by reducing transcription of ALA synthase.<sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> </p><p>The organs mainly involved in heme synthesis are the <a href="/wiki/Liver" title="Liver">liver</a> (in which the rate of synthesis is highly variable, depending on the systemic heme pool) and the <a href="/wiki/Bone_marrow" title="Bone marrow">bone marrow</a> (in which rate of synthesis of Heme is relatively constant and depends on the production of globin chain), although every cell requires heme to function properly. However, due to its toxic properties, proteins such as <a href="/w/index.php?title=Emopexin&action=edit&redlink=1" class="new" title="Emopexin (page does not exist)">emopexin</a> (Hx) are required to help maintain physiological stores of iron in order for them to be used in synthesis.<sup id="cite_ref-ReferenceA_31-0" class="reference"><a href="#cite_note-ReferenceA-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> Heme is seen as an intermediate molecule in catabolism of hemoglobin in the process of <a href="/wiki/Bilirubin_metabolism" class="mw-redirect" title="Bilirubin metabolism">bilirubin metabolism</a>. Defects in various enzymes in synthesis of heme can lead to group of disorder called porphyrias, which include <a href="/wiki/Acute_intermittent_porphyria" title="Acute intermittent porphyria">acute intermittent porphyria</a>, <a href="/wiki/Congenital_erythropoetic_porphyria" class="mw-redirect" title="Congenital erythropoetic porphyria">congenital erythropoetic porphyria</a>, <a href="/wiki/Porphyria_cutanea_tarda" title="Porphyria cutanea tarda">porphyria cutanea tarda</a>, <a href="/wiki/Hereditary_coproporphyria" title="Hereditary coproporphyria">hereditary coproporphyria</a>, <a href="/wiki/Variegate_porphyria" title="Variegate porphyria">variegate porphyria</a>, and <a href="/wiki/Erythropoietic_protoporphyria" title="Erythropoietic protoporphyria">erythropoietic protoporphyria</a>.<sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Synthesis_for_food">Synthesis for food</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Heme&action=edit&section=7" title="Edit section: Synthesis for food"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Impossible_Foods" title="Impossible Foods">Impossible Foods</a>, producers of plant-based <a href="/wiki/Meat_analogue" class="mw-redirect" title="Meat analogue">meat substitutes</a>, use an accelerated heme synthesis process involving soybean root <a href="/wiki/Leghemoglobin" title="Leghemoglobin">leghemoglobin</a> and <a href="/wiki/Pichia_pastoris" class="mw-redirect" title="Pichia pastoris">yeast</a>, adding the resulting heme to items such as meatless (<a href="/wiki/Veganism" title="Veganism">vegan</a>) Impossible burger patties. The DNA for <a href="/wiki/Leghemoglobin" title="Leghemoglobin">leghemoglobin</a> production was extracted from the soybean root nodules and expressed in yeast cells to overproduce heme for use in the meatless burgers.<sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> This process claims to create a meaty flavor in the resulting products.<sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Degradation">Degradation</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Heme&action=edit&section=8" title="Edit section: Degradation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Heme_Breakdown.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d9/Heme_Breakdown.png/220px-Heme_Breakdown.png" decoding="async" width="220" height="269" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d9/Heme_Breakdown.png/330px-Heme_Breakdown.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d9/Heme_Breakdown.png/440px-Heme_Breakdown.png 2x" data-file-width="812" data-file-height="993" /></a><figcaption>Heme breakdown</figcaption></figure> <p>Degradation begins inside macrophages of the <a href="/wiki/Spleen" title="Spleen">spleen</a>, which remove old and damaged <a href="/wiki/Erythrocytes" class="mw-redirect" title="Erythrocytes">erythrocytes</a> from the circulation. </p><p>In the first step, heme is converted to <a href="/wiki/Biliverdin" title="Biliverdin">biliverdin</a> by the enzyme <a href="/wiki/Heme_oxygenase" title="Heme oxygenase">heme oxygenase</a> (HO).<sup id="cite_ref-36" class="reference"><a href="#cite_note-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> <a href="/wiki/NADPH" class="mw-redirect" title="NADPH">NADPH</a> is used as the reducing agent, molecular oxygen enters the reaction, <a href="/wiki/Carbon_monoxide" title="Carbon monoxide">carbon monoxide</a> (CO) is produced and the iron is released from the molecule as the <a href="/wiki/Ferrous" title="Ferrous">ferrous</a> ion (Fe<sup>2+</sup>).<sup id="cite_ref-37" class="reference"><a href="#cite_note-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> CO acts as a cellular messenger and functions in vasodilation.<sup id="cite_ref-38" class="reference"><a href="#cite_note-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> </p><p>In addition, heme degradation appears to be an evolutionarily-conserved response to <a href="/wiki/Oxidative_stress" title="Oxidative stress">oxidative stress</a>. Briefly, when cells are exposed to <a href="/wiki/Free_radical" class="mw-redirect" title="Free radical">free radicals</a>, there is a rapid induction of the expression of the stress-responsive <a href="/wiki/Heme_oxygenase-1" class="mw-redirect" title="Heme oxygenase-1">heme oxygenase-1</a> (HMOX1) isoenzyme that catabolizes heme (see below).<sup id="cite_ref-39" class="reference"><a href="#cite_note-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> The reason why cells must increase exponentially their capability to degrade heme in response to oxidative stress remains unclear but this appears to be part of a cytoprotective response that avoids the deleterious effects of free heme. When large amounts of free heme accumulates, the heme detoxification/degradation systems get overwhelmed, enabling heme to exert its damaging effects.<sup id="cite_ref-ReferenceA_31-1" class="reference"><a href="#cite_note-ReferenceA-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> </p> <table style="background-color:var(--background-color-base);font-family:inherit;"> <tbody><tr> <td style="text-align:center;font-family:inherit;background-color:light-dark(lightgreen,darkgreen);color:var(--color-base);">heme </td> <td colspan="2" style="text-align:center;font-family:inherit;color:var(--color-base);background-color:light-dark(pink,#6a331d)" width="75px"><a href="/wiki/Heme_oxygenase-1" class="mw-redirect" title="Heme oxygenase-1">heme oxygenase-1</a> </td> <td style="text-align:center;font-family:inherit;color:var(--color-base);background-color:light-dark(lightgreen,darkgreen);"><a href="/wiki/Biliverdin" title="Biliverdin">biliverdin</a> + Fe<sup>2+</sup> </td></tr> <tr> <td rowspan="5" style="text-align:center;color:var(--color-base);"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Heme_b.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/be/Heme_b.svg/150px-Heme_b.svg.png" decoding="async" width="150" height="166" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/be/Heme_b.svg/225px-Heme_b.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/be/Heme_b.svg/300px-Heme_b.svg.png 2x" data-file-width="620" data-file-height="685" /></a></span> </td> <td colspan="2" style="text-align:center;" width="75">  </td> <td rowspan="5" style="text-align:center;color:var(--color-base);"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Biliverdin3.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3e/Biliverdin3.svg/150px-Biliverdin3.svg.png" decoding="async" width="150" height="135" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3e/Biliverdin3.svg/225px-Biliverdin3.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3e/Biliverdin3.svg/300px-Biliverdin3.svg.png 2x" data-file-width="431" data-file-height="387" /></a></span> </td></tr> <tr> <td style="text-align:center;color:var(--color-base);" width="38px">H<sup>+</sup> + <a href="/wiki/NADPH" class="mw-redirect" title="NADPH">NADPH</a> + O<sub>2</sub> </td> <td style="text-align:center;color:var(--color-base);" width="38px">NADP<sup>+</sup> + CO </td></tr> <tr> <td colspan="2" width="75px" style="text-align:center;color:var(--color-base);"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Biochem_reaction_arrow_forward_YYNN_horiz_med.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/85/Biochem_reaction_arrow_forward_YYNN_horiz_med.svg/75px-Biochem_reaction_arrow_forward_YYNN_horiz_med.svg.png" decoding="async" width="75" height="75" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/85/Biochem_reaction_arrow_forward_YYNN_horiz_med.svg/113px-Biochem_reaction_arrow_forward_YYNN_horiz_med.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/85/Biochem_reaction_arrow_forward_YYNN_horiz_med.svg/150px-Biochem_reaction_arrow_forward_YYNN_horiz_med.svg.png 2x" data-file-width="75" data-file-height="75" /></a></span> </td></tr> <tr> <td style="text-align:center;color:var(--color-base);" width="38px"> </td> <td style="text-align:center;color:var(--color-base);" width="38px"> </td></tr></tbody></table> <p>In the second reaction, <a href="/wiki/Biliverdin" title="Biliverdin">biliverdin</a> is converted to <a href="/wiki/Bilirubin" title="Bilirubin">bilirubin</a> by <a href="/wiki/Biliverdin_reductase" title="Biliverdin reductase">biliverdin reductase</a> (BVR):<sup id="cite_ref-pmid18276984_40-0" class="reference"><a href="#cite_note-pmid18276984-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> </p> <table style="background-color:var(--background-color-base);font-family:inherit;"> <tbody><tr> <td style="text-align:center;font-family:inherit;background-color:light-dark(lightgreen,darkgreen);color:var(--color-base);"><a href="/wiki/Biliverdin" title="Biliverdin">biliverdin</a> </td> <td colspan="2" style="text-align:center;font-family:inherit;color:var(--color-base);background-color:light-dark(pink,#6a331d)" width="75px"><a href="/wiki/Biliverdin_reductase" title="Biliverdin reductase">biliverdin reductase</a> </td> <td style="text-align:center;font-family:inherit;color:var(--color-base);background-color:light-dark(lightgreen,darkgreen);"><a href="/wiki/Bilirubin" title="Bilirubin">bilirubin</a> </td></tr> <tr> <td rowspan="5" style="text-align:center;color:var(--color-base);"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Biliverdin3.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3e/Biliverdin3.svg/150px-Biliverdin3.svg.png" decoding="async" width="150" height="135" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3e/Biliverdin3.svg/225px-Biliverdin3.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3e/Biliverdin3.svg/300px-Biliverdin3.svg.png 2x" data-file-width="431" data-file-height="387" /></a></span> </td> <td colspan="2" style="text-align:center;" width="75">  </td> <td rowspan="5" style="text-align:center;color:var(--color-base);"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Bilirubin_ZZ.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Bilirubin_ZZ.png/150px-Bilirubin_ZZ.png" decoding="async" width="150" height="57" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Bilirubin_ZZ.png/225px-Bilirubin_ZZ.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Bilirubin_ZZ.png/300px-Bilirubin_ZZ.png 2x" data-file-width="1257" data-file-height="481" /></a></span> </td></tr> <tr> <td style="text-align:center;color:var(--color-base);" width="38px">H<sup>+</sup> + <a href="/wiki/NADPH" class="mw-redirect" title="NADPH">NADPH</a> </td> <td style="text-align:center;color:var(--color-base);" width="38px">NADP<sup>+</sup> </td></tr> <tr> <td colspan="2" width="75px" style="text-align:center;color:var(--color-base);"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Biochem_reaction_arrow_forward_YYNN_horiz_med.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/85/Biochem_reaction_arrow_forward_YYNN_horiz_med.svg/75px-Biochem_reaction_arrow_forward_YYNN_horiz_med.svg.png" decoding="async" width="75" height="75" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/85/Biochem_reaction_arrow_forward_YYNN_horiz_med.svg/113px-Biochem_reaction_arrow_forward_YYNN_horiz_med.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/85/Biochem_reaction_arrow_forward_YYNN_horiz_med.svg/150px-Biochem_reaction_arrow_forward_YYNN_horiz_med.svg.png 2x" data-file-width="75" data-file-height="75" /></a></span> </td></tr> <tr> <td style="text-align:center;color:var(--color-base);" width="38px"> </td> <td style="text-align:center;color:var(--color-base);" width="38px"> </td></tr></tbody></table> <p>Bilirubin is transported into the liver by facilitated diffusion bound to a protein (<a href="/wiki/Serum_albumin" title="Serum albumin">serum albumin</a>), where it is conjugated with <a href="/wiki/Glucuronic_acid" title="Glucuronic acid">glucuronic acid</a> to become more water-soluble. The reaction is catalyzed by the enzyme UDP-<a href="/wiki/Glucuronosyltransferase" title="Glucuronosyltransferase">glucuronosyltransferase</a>.<sup id="cite_ref-41" class="reference"><a href="#cite_note-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> </p> <table style="background-color:var(--background-color-base);font-family:inherit;"> <tbody><tr> <td style="text-align:center;font-family:inherit;background-color:light-dark(lightgreen,darkgreen);color:var(--color-base);"><a href="/wiki/Bilirubin" title="Bilirubin">bilirubin</a> </td> <td colspan="2" style="text-align:center;font-family:inherit;color:var(--color-base);background-color:light-dark(pink,#6a331d)" width="75px">UDP-<a href="/wiki/Glucuronosyltransferase" title="Glucuronosyltransferase">glucuronosyltransferase</a> </td> <td style="text-align:center;font-family:inherit;color:var(--color-base);background-color:light-dark(lightgreen,darkgreen);"><a href="/wiki/Bilirubin_diglucuronide" title="Bilirubin diglucuronide">bilirubin diglucuronide</a> </td></tr> <tr> <td rowspan="5" style="text-align:center;color:var(--color-base);"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Bilirubin_ZZ.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Bilirubin_ZZ.png/150px-Bilirubin_ZZ.png" decoding="async" width="150" height="57" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Bilirubin_ZZ.png/225px-Bilirubin_ZZ.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Bilirubin_ZZ.png/300px-Bilirubin_ZZ.png 2x" data-file-width="1257" data-file-height="481" /></a></span> </td> <td colspan="2" style="text-align:center;" width="75">  </td> <td rowspan="5" style="text-align:center;color:var(--color-base);"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Bilirubin_diglucuronide.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/50/Bilirubin_diglucuronide.svg/250px-Bilirubin_diglucuronide.svg.png" decoding="async" width="250" height="129" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/50/Bilirubin_diglucuronide.svg/375px-Bilirubin_diglucuronide.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/50/Bilirubin_diglucuronide.svg/500px-Bilirubin_diglucuronide.svg.png 2x" data-file-width="3070" data-file-height="1581" /></a></span> </td></tr> <tr> <td style="text-align:center;color:var(--color-base);" width="38px">2 <a href="/wiki/Uridine_diphosphate_glucuronic_acid" title="Uridine diphosphate glucuronic acid">UDP-glucuronide</a> </td> <td style="text-align:center;color:var(--color-base);" width="38px">2 <a href="/wiki/Uridine_monophosphate" title="Uridine monophosphate">UMP</a> + 2 <a href="/wiki/Phosphate" title="Phosphate">P<sub>i</sub></a> </td></tr> <tr> <td colspan="2" width="75px" style="text-align:center;color:var(--color-base);"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Biochem_reaction_arrow_forward_YYNN_horiz_med.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/85/Biochem_reaction_arrow_forward_YYNN_horiz_med.svg/75px-Biochem_reaction_arrow_forward_YYNN_horiz_med.svg.png" decoding="async" width="75" height="75" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/85/Biochem_reaction_arrow_forward_YYNN_horiz_med.svg/113px-Biochem_reaction_arrow_forward_YYNN_horiz_med.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/85/Biochem_reaction_arrow_forward_YYNN_horiz_med.svg/150px-Biochem_reaction_arrow_forward_YYNN_horiz_med.svg.png 2x" data-file-width="75" data-file-height="75" /></a></span> </td></tr> <tr> <td style="text-align:center;color:var(--color-base);" width="38px"> </td> <td style="text-align:center;color:var(--color-base);" width="38px"> </td></tr></tbody></table> <p>This form of bilirubin is excreted from the liver in <a href="/wiki/Bile" title="Bile">bile</a>. Excretion of bilirubin from liver to biliary canaliculi is an active, energy-dependent and rate-limiting process. The <a href="/wiki/Gut_flora" class="mw-redirect" title="Gut flora">intestinal bacteria</a> deconjugate <a href="/wiki/Bilirubin_diglucuronide" title="Bilirubin diglucuronide">bilirubin diglucuronide</a> releasing free bilirubin, which can either be reabsorbed or reduced to <a href="/wiki/Urobilinogen" title="Urobilinogen">urobilinogen</a> by the bacterial enzyme bilirubin reductase.<sup id="cite_ref-42" class="reference"><a href="#cite_note-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> </p> <table style="background-color:var(--background-color-base);font-family:inherit;"> <tbody><tr> <td style="text-align:center;font-family:inherit;background-color:light-dark(lightgreen,darkgreen);color:var(--color-base);"><a href="/wiki/Bilirubin" title="Bilirubin">bilirubin</a> </td> <td colspan="2" style="text-align:center;font-family:inherit;color:var(--color-base);background-color:light-dark(pink,#6a331d)" width="75px">bilirubin reductase </td> <td style="text-align:center;font-family:inherit;color:var(--color-base);background-color:light-dark(lightgreen,darkgreen);"><a href="/wiki/Urobilinogen" title="Urobilinogen">urobilinogen</a> </td></tr> <tr> <td rowspan="5" style="text-align:center;color:var(--color-base);"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Bilirubin_ZZ.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Bilirubin_ZZ.png/220px-Bilirubin_ZZ.png" decoding="async" width="220" height="84" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Bilirubin_ZZ.png/330px-Bilirubin_ZZ.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Bilirubin_ZZ.png/440px-Bilirubin_ZZ.png 2x" data-file-width="1257" data-file-height="481" /></a></span> </td> <td colspan="2" style="text-align:center;" width="75">  </td> <td rowspan="5" style="text-align:center;color:var(--color-base);"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Urobilinogen.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0d/Urobilinogen.svg/220px-Urobilinogen.svg.png" decoding="async" width="220" height="137" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0d/Urobilinogen.svg/330px-Urobilinogen.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0d/Urobilinogen.svg/440px-Urobilinogen.svg.png 2x" data-file-width="955" data-file-height="595" /></a></span> </td></tr> <tr> <td style="text-align:center;color:var(--color-base);" width="38px">4 <a href="/wiki/NAD(P)H" class="mw-redirect" title="NAD(P)H">NAD(P)H</a> + 4 H<sup>+</sup> </td> <td style="text-align:center;color:var(--color-base);" width="38px">4 NAD(P)<sup>+</sup> </td></tr> <tr> <td colspan="2" width="75px" style="text-align:center;color:var(--color-base);"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Biochem_reaction_arrow_forward_YYNN_horiz_med.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/85/Biochem_reaction_arrow_forward_YYNN_horiz_med.svg/75px-Biochem_reaction_arrow_forward_YYNN_horiz_med.svg.png" decoding="async" width="75" height="75" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/85/Biochem_reaction_arrow_forward_YYNN_horiz_med.svg/113px-Biochem_reaction_arrow_forward_YYNN_horiz_med.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/85/Biochem_reaction_arrow_forward_YYNN_horiz_med.svg/150px-Biochem_reaction_arrow_forward_YYNN_horiz_med.svg.png 2x" data-file-width="75" data-file-height="75" /></a></span> </td></tr> <tr> <td style="text-align:center;color:var(--color-base);" width="38px"> </td> <td style="text-align:center;color:var(--color-base);" width="38px"> </td></tr></tbody></table> <p><br /> Some urobilinogen is absorbed by intestinal cells and transported into the <a href="/wiki/Kidney" title="Kidney">kidneys</a> and excreted with <a href="/wiki/Urine" title="Urine">urine</a> (<a href="/wiki/Urobilin" title="Urobilin">urobilin</a>, which is the product of oxidation of urobilinogen, and is responsible for the yellow colour of urine). The remainder travels down the digestive tract and is converted to <a href="/wiki/Stercobilinogen" title="Stercobilinogen">stercobilinogen</a>. This is oxidized to <a href="/wiki/Stercobilin" title="Stercobilin">stercobilin</a>, which is excreted and is responsible for the brown color of <a href="/wiki/Feces" title="Feces">feces</a>.<sup id="cite_ref-43" class="reference"><a href="#cite_note-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="In_health_and_disease">In health and disease</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Heme&action=edit&section=9" title="Edit section: In health and disease"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Under <a href="/wiki/Homeostasis" title="Homeostasis">homeostasis</a>, the reactivity of heme is controlled by its insertion into the "heme pockets" of hemoproteins.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (December 2016)">citation needed</span></a></i>]</sup> Under oxidative stress however, some hemoproteins, e.g. hemoglobin, can release their heme prosthetic groups.<sup id="cite_ref-44" class="reference"><a href="#cite_note-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-45" class="reference"><a href="#cite_note-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> The non-protein-bound (free) heme produced in this manner becomes highly cytotoxic, most probably due to the iron atom contained within its protoporphyrin IX ring, which can act as a <a href="/wiki/Fenton%27s_reagent" title="Fenton's reagent">Fenton's reagent</a> to catalyze in an unfettered manner the production of free radicals.<sup id="cite_ref-46" class="reference"><a href="#cite_note-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> It catalyzes the oxidation and aggregation of protein, the formation of cytotoxic lipid peroxide via lipid peroxidation and damages DNA through oxidative stress. Due to its lipophilic properties, it impairs lipid bilayers in organelles such as mitochondria and nuclei.<sup id="cite_ref-47" class="reference"><a href="#cite_note-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> These properties of free heme can sensitize a variety of cell types to undergo <a href="/wiki/Programmed_cell_death" title="Programmed cell death">programmed cell death</a> in response to pro-inflammatory agonists, a deleterious effect that plays an important role in the pathogenesis of certain inflammatory diseases such as <a href="/wiki/Malaria" title="Malaria">malaria</a><sup id="cite_ref-pmid17496899_48-0" class="reference"><a href="#cite_note-pmid17496899-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Sepsis" title="Sepsis">sepsis</a>.<sup id="cite_ref-49" class="reference"><a href="#cite_note-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Cancer">Cancer</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Heme&action=edit&section=10" title="Edit section: Cancer"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>There is an association between high intake of heme iron sourced from meat and increased risk of <a href="/wiki/Colorectal_cancer" title="Colorectal cancer">colorectal cancer</a>.<sup id="cite_ref-50" class="reference"><a href="#cite_note-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup> </p><p>The <a href="/wiki/American_Institute_for_Cancer_Research" title="American Institute for Cancer Research">American Institute for Cancer Research</a> (AICR) and World Cancer Research Fund International (WCRF) concluded in a 2018 report that there is limited but suggestive evidence that foods containing heme iron increase risk of colorectal cancer.<sup id="cite_ref-51" class="reference"><a href="#cite_note-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> A 2019 review found that heme iron intake is associated with increased <a href="/wiki/Breast_cancer" title="Breast cancer">breast cancer</a> risk.<sup id="cite_ref-52" class="reference"><a href="#cite_note-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Genes">Genes</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Heme&action=edit&section=11" title="Edit section: Genes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The following genes are part of the chemical pathway for making heme: </p> <ul><li><i><a href="/wiki/ALAD" class="mw-redirect" title="ALAD">ALAD</a></i>: aminolevulinic acid, δ-, <a href="/wiki/Dehydratase" title="Dehydratase">dehydratase</a> (deficiency causes ala-dehydratase deficiency porphyria)<sup id="cite_ref-53" class="reference"><a href="#cite_note-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup></li> <li><i><a href="/wiki/ALAS1" title="ALAS1">ALAS1</a></i>: aminolevulinate, δ-, synthase 1</li> <li><i><a href="/wiki/ALAS2" title="ALAS2">ALAS2</a></i>: aminolevulinate, δ-, synthase 2 (deficiency causes sideroblastic/hypochromic anemia)</li> <li><i><a href="/wiki/Coproporphyrinogen_III_oxidase" title="Coproporphyrinogen III oxidase">CPOX</a></i>: coproporphyrinogen <a href="/wiki/Oxidase" title="Oxidase">oxidase</a> (deficiency causes hereditary coproporphyria)<sup id="cite_ref-54" class="reference"><a href="#cite_note-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup></li> <li><i><a href="/wiki/Ferrochelatase" title="Ferrochelatase">FECH</a></i>: <a href="/wiki/Ferrochelatase" title="Ferrochelatase">ferrochelatase</a> (deficiency causes <a href="/wiki/Erythropoietic_protoporphyria" title="Erythropoietic protoporphyria">erythropoietic protoporphyria</a>)</li> <li><i><a href="/wiki/HMBS_(gene)" class="mw-redirect" title="HMBS (gene)">HMBS</a></i>: hydroxymethylbilane <a href="/wiki/Synthase" title="Synthase">synthase</a> (deficiency causes acute intermittent porphyria)<sup id="cite_ref-55" class="reference"><a href="#cite_note-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup></li> <li><i><a href="/wiki/PPOX" class="mw-redirect" title="PPOX">PPOX</a></i>: protoporphyrinogen <a href="/wiki/Oxidase" title="Oxidase">oxidase</a> (deficiency causes variegate porphyria)<sup id="cite_ref-56" class="reference"><a href="#cite_note-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup></li> <li><i><a href="/wiki/UROD" class="mw-redirect" title="UROD">UROD</a></i>: <a href="/wiki/Uroporphyrinogen" title="Uroporphyrinogen">uroporphyrinogen</a> <a href="/wiki/Decarboxylase" class="mw-redirect" title="Decarboxylase">decarboxylase</a> (deficiency causes porphyria cutanea tarda)<sup id="cite_ref-57" class="reference"><a href="#cite_note-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup></li> <li><i><a href="/wiki/UROS" class="mw-redirect" title="UROS">UROS</a></i>: <a href="/wiki/Uroporphyrinogen" title="Uroporphyrinogen">uroporphyrinogen</a> III <a href="/wiki/Synthase" title="Synthase">synthase</a> (deficiency causes congenital erythropoietic porphyria)</li></ul> <div class="mw-heading mw-heading2"><h2 id="Notes_and_references">Notes and references</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Heme&action=edit&section=12" title="Edit section: Notes and references"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist reflist-columns references-column-width reflist-columns-2"> <ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFHodgsonRoeMailmanChambers2015" class="citation book cs1">Hodgson E, Roe RM, Mailman RB, Chambers JE, eds. (2015). <a rel="nofollow" class="external text" href="https://www.sciencedirect.com/science/article/pii/B9780124201699000084">"H"</a>. <i>Dictionary of Toxicology</i> (3rd ed.). Academic Press. pp. <span class="nowrap">173–</span>184. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FB978-0-12-420169-9.00008-4">10.1016/B978-0-12-420169-9.00008-4</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-12-420169-9" title="Special:BookSources/978-0-12-420169-9"><bdi>978-0-12-420169-9</bdi></a><span class="reference-accessdate">. Retrieved <span class="nowrap">2024-02-21</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=H&rft.btitle=Dictionary+of+Toxicology&rft.pages=%3Cspan+class%3D%22nowrap%22%3E173-%3C%2Fspan%3E184&rft.edition=3rd&rft.pub=Academic+Press&rft.date=2015&rft_id=info%3Adoi%2F10.1016%2FB978-0-12-420169-9.00008-4&rft.isbn=978-0-12-420169-9&rft_id=https%3A%2F%2Fwww.sciencedirect.com%2Fscience%2Farticle%2Fpii%2FB9780124201699000084&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHeme" class="Z3988"></span></span> </li> <li id="cite_note-bloomer98-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-bloomer98_2-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBloomer1998" class="citation journal cs1">Bloomer JR (1998). <a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1440-1746.1998.01548.x">"Liver metabolism of porphyrins and haem"</a>. <i>Journal of Gastroenterology and Hepatology</i>. <b>13</b> (3): <span class="nowrap">324–</span>329. <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/10.1111%2Fj.1440-1746.1998.01548.x">10.1111/j.1440-1746.1998.01548.x</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/9570250">9570250</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:25224821">25224821</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Gastroenterology+and+Hepatology&rft.atitle=Liver+metabolism+of+porphyrins+and+haem&rft.volume=13&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E324-%3C%2Fspan%3E329&rft.date=1998&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A25224821%23id-name%3DS2CID&rft_id=info%3Apmid%2F9570250&rft_id=info%3Adoi%2F10.1111%2Fj.1440-1746.1998.01548.x&rft.aulast=Bloomer&rft.aufirst=Joseph+R.&rft_id=https%3A%2F%2Fdoi.org%2F10.1111%252Fj.1440-1746.1998.01548.x&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHeme" class="Z3988"></span></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDuttHamzaBartnikas2022" class="citation journal cs1">Dutt S, Hamza I, Bartnikas TB (2022-08-22). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9398995">"Molecular Mechanisms of Iron and Heme Metabolism"</a>. <i>Annual Review of Nutrition</i>. <b>42</b> (1): <span class="nowrap">311–</span>335. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1146%2Fannurev-nutr-062320-112625">10.1146/annurev-nutr-062320-112625</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/0199-9885">0199-9885</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/PMC9398995">9398995</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/35508203">35508203</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Annual+Review+of+Nutrition&rft.atitle=Molecular+Mechanisms+of+Iron+and+Heme+Metabolism&rft.volume=42&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E311-%3C%2Fspan%3E335&rft.date=2022-08-22&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC9398995%23id-name%3DPMC&rft.issn=0199-9885&rft_id=info%3Apmid%2F35508203&rft_id=info%3Adoi%2F10.1146%2Fannurev-nutr-062320-112625&rft.aulast=Dutt&rft.aufirst=Sohini&rft.au=Hamza%2C+Iqbal&rft.au=Bartnikas%2C+Thomas+Benedict&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC9398995&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHeme" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFOgunJoyValentine2024" class="citation cs2">Ogun AS, Joy NV, Valentine M (2024), <a rel="nofollow" class="external text" href="http://www.ncbi.nlm.nih.gov/books/NBK537329/">"Biochemistry, Heme Synthesis"</a>, <i>StatPearls</i>, Treasure Island (FL): StatPearls Publishing, <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/30726014">30726014</a><span class="reference-accessdate">, retrieved <span class="nowrap">2024-02-22</span></span></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=StatPearls&rft.atitle=Biochemistry%2C+Heme+Synthesis&rft.date=2024&rft_id=info%3Apmid%2F30726014&rft.aulast=Ogun&rft.aufirst=Aminat+S.&rft.au=Joy%2C+Neena+V.&rft.au=Valentine%2C+Menogh&rft_id=http%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fbooks%2FNBK537329%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHeme" class="Z3988"></span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFChemistry2009" class="citation book cs1">Chemistry IU (2009). <a rel="nofollow" class="external text" href="https://goldbook.iupac.org/html/H/H02773.html">"Hemes (heme derivatives)"</a>. <i>IUPAC Compendium of Chemical Terminology</i>. IUPAC. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fgoldbook.H02773">10.1351/goldbook.H02773</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-9678550-9-7" title="Special:BookSources/978-0-9678550-9-7"><bdi>978-0-9678550-9-7</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170822011820/http://goldbook.iupac.org/html/H/H02773.html">Archived</a> from the original on 22 August 2017<span class="reference-accessdate">. Retrieved <span class="nowrap">28 April</span> 2018</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Hemes+%28heme+derivatives%29&rft.btitle=IUPAC+Compendium+of+Chemical+Terminology&rft.pub=IUPAC&rft.date=2009&rft_id=info%3Adoi%2F10.1351%2Fgoldbook.H02773&rft.isbn=978-0-9678550-9-7&rft.aulast=Chemistry&rft.aufirst=International+Union+of+Pure+and+Applied&rft_id=https%3A%2F%2Fgoldbook.iupac.org%2Fhtml%2FH%2FH02773.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHeme" class="Z3988"></span></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text">A standard biochemistry text defines heme as the "iron-porphyrin prosthetic group of heme proteins"(Nelson, D. L.; Cox, M. M. "Lehninger, Principles of Biochemistry" 3rd Ed. Worth Publishing: New York, 2000. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/1-57259-153-6" title="Special:BookSources/1-57259-153-6">1-57259-153-6</a>.)</span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPoulos2014" class="citation journal cs1">Poulos TL (2014-04-09). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3981943">"Heme Enzyme Structure and Function"</a>. <i>Chemical Reviews</i>. <b>114</b> (7): <span class="nowrap">3919–</span>3962. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" 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title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Bioscience+Reports&rft.atitle=Conformational+stability+and+activity+analysis+of+two+hydroxymethylbilane+synthase+mutants%2C+K132N+and+V215E%2C+with+different+phenotypic+association+with+acute+intermittent+porphyria&rft.volume=33&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E617-%3C%2Fspan%3E626&rft.date=2013-08-08&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3738108%23id-name%3DPMC&rft_id=info%3Apmid%2F23815679&rft_id=info%3Adoi%2F10.1042%2FBSR20130045&rft.aulast=Bustad&rft.aufirst=H.+J.&rft.au=Vorland%2C+M.&rft.au=Ronneseth%2C+E.&rft.au=Sandberg%2C+S.&rft.au=Martinez%2C+A.&rft.au=Toska%2C+K.&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3738108&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHeme" class="Z3988"></span></span> </li> <li id="cite_note-56"><span class="mw-cite-backlink"><b><a href="#cite_ref-56">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMartinez_di_MontemurosDi_PierroPattiTavazzi2002" class="citation journal cs1">Martinez di Montemuros F, Di Pierro E, Patti E, Tavazzi D, Danielli MG, Biolcati G, Rocchi E, Cappellini MD (December 2002). <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/12699245/">"Molecular characterization of porphyrias in Italy: a diagnostic flow-chart"</a>. <i>Cellular and Molecular Biology (Noisy-Le-Grand, France)</i>. <b>48</b> (8): <span class="nowrap">867–</span>876. <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/0145-5680">0145-5680</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/12699245">12699245</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Cellular+and+Molecular+Biology+%28Noisy-Le-Grand%2C+France%29&rft.atitle=Molecular+characterization+of+porphyrias+in+Italy%3A+a+diagnostic+flow-chart&rft.volume=48&rft.issue=8&rft.pages=%3Cspan+class%3D%22nowrap%22%3E867-%3C%2Fspan%3E876&rft.date=2002-12&rft_id=info%3Apmid%2F12699245&rft.issn=0145-5680&rft.aulast=Martinez+di+Montemuros&rft.aufirst=F.&rft.au=Di+Pierro%2C+E.&rft.au=Patti%2C+E.&rft.au=Tavazzi%2C+D.&rft.au=Danielli%2C+M.+G.&rft.au=Biolcati%2C+G.&rft.au=Rocchi%2C+E.&rft.au=Cappellini%2C+M.+D.&rft_id=https%3A%2F%2Fpubmed.ncbi.nlm.nih.gov%2F12699245%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHeme" class="Z3988"></span></span> </li> <li id="cite_note-57"><span class="mw-cite-backlink"><b><a href="#cite_ref-57">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBadenasTo_FiguerasPhillipsWarby2009" class="citation journal cs1">Badenas C, To Figueras J, Phillips JD, Warby CA, Muñoz C, Herrero C (April 2009). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3804340">"Identification and characterization of novel uroporphyrinogen decarboxylase gene mutations in a large series of porphyria cutanea tarda patients and relatives"</a>. <i>Clinical Genetics</i>. <b>75</b> (4): <span class="nowrap">346–</span>353. <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%2Fj.1399-0004.2009.01153.x">10.1111/j.1399-0004.2009.01153.x</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/PMC3804340">3804340</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/19419417">19419417</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Clinical+Genetics&rft.atitle=Identification+and+characterization+of+novel+uroporphyrinogen+decarboxylase+gene+mutations+in+a+large+series+of+porphyria+cutanea+tarda+patients+and+relatives&rft.volume=75&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E346-%3C%2Fspan%3E353&rft.date=2009-04&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3804340%23id-name%3DPMC&rft_id=info%3Apmid%2F19419417&rft_id=info%3Adoi%2F10.1111%2Fj.1399-0004.2009.01153.x&rft.aulast=Badenas&rft.aufirst=C.&rft.au=To+Figueras%2C+J.&rft.au=Phillips%2C+J.+D.&rft.au=Warby%2C+C.+A.&rft.au=Mu%C3%B1oz%2C+C.&rft.au=Herrero%2C+C.&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3804340&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHeme" class="Z3988"></span></span> </li> </ol></div> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist 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.navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Heme_metabolism_intermediates" title="Template:Heme metabolism intermediates"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Heme_metabolism_intermediates" title="Template talk:Heme metabolism intermediates"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Heme_metabolism_intermediates" title="Special:EditPage/Template:Heme metabolism intermediates"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Heme_metabolic_intermediates141" style="font-size:114%;margin:0 4em"><a class="mw-selflink selflink">Heme</a> <a href="/wiki/Metabolic_intermediate" title="Metabolic intermediate">metabolic intermediates</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Porphyrin#Biosynthesis" title="Porphyrin">Porphyrin biosynthesis</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><span class="nobold"><i>early mitochondrial:</i></span></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/Aminolevulinic_acid" title="Aminolevulinic acid">D-Aminolevulinic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><span class="nobold"><i>cytosolic:</i></span></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/Porphobilinogen" title="Porphobilinogen">Porphobilinogen</a></li> <li><a href="/wiki/Hydroxymethylbilane" title="Hydroxymethylbilane">Hydroxymethylbilane</a></li> <li><a href="/wiki/Uroporphyrinogen_III" title="Uroporphyrinogen III">Uroporphyrinogen III</a></li> <li><a href="/wiki/Coproporphyrinogen_III" title="Coproporphyrinogen III">Coproporphyrinogen III</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><span class="nobold"><i>late mitochondrial:</i></span></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/Protoporphyrinogen_IX" title="Protoporphyrinogen IX">Protoporphyrinogen IX</a></li> <li><a href="/wiki/Protoporphyrin_IX" title="Protoporphyrin IX">Protoporphyrin IX</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a class="mw-selflink-fragment" href="#Degradation">Heme degradation</a><br />and excretion</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Breakdown_of_heme72" scope="row" class="navbox-group" style="width:1%">Breakdown of heme</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><span class="nobold"><i>spleen:</i></span></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a class="mw-selflink selflink">Heme</a> → <a href="/wiki/Biliverdin" title="Biliverdin">Biliverdin</a> → <a href="/wiki/Bilirubin" title="Bilirubin">Bilirubin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><span class="nobold"><i>blood:</i></span></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/Bilirubin" title="Bilirubin">Bilirubin</a>+<a href="/wiki/Albumin" title="Albumin">Albumin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><span class="nobold"><i>liver:</i></span></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/Bilirubin_glucuronide" title="Bilirubin glucuronide">Bilirubin glucuronide</a></li> <li><a href="/wiki/Bilirubin_diglucuronide" title="Bilirubin diglucuronide">Bilirubin diglucuronide</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Intestine, excretion in feces</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/Stercobilinogen" title="Stercobilinogen">Stercobilinogen</a></li> <li><a href="/wiki/Stercobilin" title="Stercobilin">Stercobilin</a></li> <li><a href="/wiki/Urobilinogen" title="Urobilinogen">Urobilinogen</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Kidney, excretion in urine</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/Urobilin" title="Urobilin">Urobilin</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Types_of_tetrapyrroles84" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Tetrapyrroles" title="Template:Tetrapyrroles"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Tetrapyrroles" title="Template talk:Tetrapyrroles"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Tetrapyrroles" title="Special:EditPage/Template:Tetrapyrroles"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Types_of_tetrapyrroles84" style="font-size:114%;margin:0 4em">Types of <a href="/wiki/Tetrapyrrole" title="Tetrapyrrole">tetrapyrroles</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Bilin_(biochemistry)" title="Bilin (biochemistry)">Bilanes</a><br />(Linear)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Bilirubin" title="Bilirubin">Bilirubin</a></li> <li><a href="/wiki/Biliverdin" title="Biliverdin">Biliverdin</a></li> <li><a href="/wiki/Stercobilinogen" title="Stercobilinogen">Stercobilinogen</a></li> <li><a href="/wiki/Stercobilin" title="Stercobilin">Stercobilin</a></li> <li><a href="/wiki/Urobilinogen" title="Urobilinogen">Urobilinogen</a></li> <li><a href="/wiki/Urobilin" title="Urobilin">Urobilin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/w/index.php?title=Phytobilin&action=edit&redlink=1" class="new" title="Phytobilin (page does not exist)">Phytobilins</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Phytochromobilin" class="mw-redirect" title="Phytochromobilin">Phytochromobilin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phycobilin" title="Phycobilin">Phycobilins</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/Phycoerythrobilin" title="Phycoerythrobilin">Phycoerythrobilin</a></li> <li><a href="/wiki/Phycocyanobilin" title="Phycocyanobilin">Phycocyanobilin</a></li> <li><a href="/wiki/Phycourobilin" title="Phycourobilin">Phycourobilin</a></li> <li><a href="/w/index.php?title=Phycoviolobilin&action=edit&redlink=1" class="new" title="Phycoviolobilin (page does not exist)">Phycoviolobilin</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Macrocycle" title="Macrocycle">Macrocycle</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Corrinoid" title="Corrinoid">Corrinoids</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/Adenosylcobalamin" title="Adenosylcobalamin">Adenosylcobalamin</a></li> <li><a href="/wiki/Cyanocobalamin" title="Cyanocobalamin">Cyanocobalamin</a></li> <li><a href="/wiki/Methylcobalamin" title="Methylcobalamin">Methylcobalamin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Porphyrin" title="Porphyrin">Porphyrins</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Protoporphyrin" class="mw-redirect" title="Protoporphyrin">Protoporphyrins</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 class="mw-selflink selflink">Heme</a> (<a href="/wiki/Heme_b" class="mw-redirect" title="Heme b"><i>b</i></a>, <a href="/wiki/Heme_c" class="mw-redirect" title="Heme c"><i>c</i></a>, <a href="/wiki/Heme_a" class="mw-redirect" title="Heme a"><i>a</i></a>, <a href="/wiki/Heme_o" class="mw-redirect" title="Heme o"><i>o</i></a>)</li> <li><a href="/w/index.php?title=Magnesium_protoporphyrin&action=edit&redlink=1" class="new" title="Magnesium protoporphyrin (page does not exist)">Magnesium protoporphyrin</a></li> <li><a href="/wiki/Protoporphyrin_IX" title="Protoporphyrin IX">Protoporphyrin IX</a></li> <li><a href="/wiki/Pterobilin" title="Pterobilin">Pterobilin</a></li> <li><a href="/wiki/Zinc_protoporphyrin" title="Zinc protoporphyrin">Zinc protoporphyrin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/w/index.php?title=Phytoporphyrin&action=edit&redlink=1" class="new" title="Phytoporphyrin (page does not exist)">Phytoporphyrins</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/Chlorophyll_c" title="Chlorophyll c">Chlorophyll <i>c</i></a></li> <li><a href="/wiki/Protochlorophyllide" title="Protochlorophyllide">Protochlorophyllide</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Reduced<br />porphyrins</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Porphyrinogens85" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Porphyrinogen" title="Porphyrinogen">Porphyrinogens</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/Uroporphyrinogen" title="Uroporphyrinogen">Uroporphyrinogen</a> (<a href="/wiki/Uroporphyrinogen_I" title="Uroporphyrinogen I">I</a>, <a href="/wiki/Uroporphyrinogen_III" title="Uroporphyrinogen III">III</a>)</li> <li><a href="/wiki/Coproporphyrinogens" title="Coproporphyrinogens">Coproporphyrinogen</a> (<a href="/wiki/Coproporphyrinogen_I" title="Coproporphyrinogen I">I</a>, <a href="/wiki/Coproporphyrinogen_III" title="Coproporphyrinogen III">III</a>)</li> <li><a href="/wiki/Protoporphyrinogen_IX" title="Protoporphyrinogen IX">Protoporphyrinogen IX</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Chlorin" title="Chlorin">Chlorins</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/Chlorophyllide" title="Chlorophyllide">Chlorophyllide</a> (<a href="/wiki/Chlorophyllide_a" class="mw-redirect" title="Chlorophyllide a"><i>a</i></a>, <a href="/wiki/Chlorophyllide_b" class="mw-redirect" title="Chlorophyllide b"><i>b</i></a>)</li> <li><a href="/wiki/Chlorophyll" title="Chlorophyll">Chlorophyll</a> (<a href="/wiki/Chlorophyll_a" title="Chlorophyll a"><i>a</i></a>, <a href="/wiki/Chlorophyll_b" title="Chlorophyll b"><i>b</i></a>)</li> <li><a href="/wiki/Pheophytin" title="Pheophytin">Pheophytin</a> (<a href="/wiki/Pheophytin_a" class="mw-redirect" title="Pheophytin a"><i>a</i></a>, <a href="/w/index.php?title=Pheophytin_b&action=edit&redlink=1" class="new" title="Pheophytin b (page does not exist)"><i>b</i></a>)</li> <li><a href="/wiki/Bacteriochlorophyll_c" class="mw-redirect" title="Bacteriochlorophyll c">Bacteriochlorophyll <i>c</i></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Bacteriochlorin" class="mw-redirect" title="Bacteriochlorin">Bacteriochlorins</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/Bacteriochlorophyll_a" class="mw-redirect" title="Bacteriochlorophyll a">Bacteriochlorophyll <i>a</i></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Isobacteriochlorin" class="mw-redirect" title="Isobacteriochlorin">Isobacteriochlorins</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/Siroheme" title="Siroheme">Siroheme</a></li> <li><a href="/wiki/Sirohydrochlorin" title="Sirohydrochlorin">Sirohydrochlorin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/w/index.php?title=Corphin&action=edit&redlink=1" class="new" title="Corphin (page does not exist)">Corphins</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/Cofactor_F430" title="Cofactor F430">Cofactor F430</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Enzyme_cofactors70" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Enzyme_cofactors" title="Template:Enzyme cofactors"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Enzyme_cofactors" title="Template talk:Enzyme cofactors"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Enzyme_cofactors" title="Special:EditPage/Template:Enzyme cofactors"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Enzyme_cofactors70" 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> (B<sub>1</sub>)</li> <li><a href="/wiki/Flavin_mononucleotide" title="Flavin mononucleotide">FMN</a>, <a href="/wiki/Flavin_adenine_dinucleotide" title="Flavin adenine dinucleotide">FAD</a> (B<sub>2</sub>)</li> <li><a href="/wiki/Nicotinamide_adenine_dinucleotide" title="Nicotinamide adenine dinucleotide">NAD<sup>+</sup></a>, <a href="/wiki/Nicotinamide_adenine_dinucleotide" title="Nicotinamide adenine dinucleotide">NADH</a>, <a href="/wiki/Nicotinamide_adenine_dinucleotide_phosphate" title="Nicotinamide adenine dinucleotide phosphate">NADP<sup>+</sup></a>, <a href="/wiki/Nicotinamide_adenine_dinucleotide_phosphate" title="Nicotinamide adenine dinucleotide phosphate">NADPH</a> (B<sub>3</sub>)</li> <li><a href="/wiki/Coenzyme_A" title="Coenzyme A">Coenzyme A</a> (B<sub>5</sub>)</li> <li><a href="/wiki/Pyridoxal_phosphate" title="Pyridoxal phosphate">PLP / P5P</a> (B<sub>6</sub>)</li> <li><a href="/wiki/Biotin" title="Biotin">Biotin</a> (B<sub>7</sub>)</li> <li><a href="/wiki/Tetrahydrofolic_acid" title="Tetrahydrofolic acid">THFA / H<sub>4</sub>FA</a>, <a href="/wiki/Dihydrofolic_acid" title="Dihydrofolic acid">DHFA / H<sub>2</sub>FA</a>, <a href="/wiki/5,10-Methylenetetrahydrofolate" title="5,10-Methylenetetrahydrofolate">MTHF</a> (B<sub>9</sub>)</li> <li><a href="/wiki/Adenosylcobalamin" title="Adenosylcobalamin">AdoCbl</a>, <a href="/wiki/Methylcobalamin" title="Methylcobalamin">MeCbl</a> (B<sub>12</sub>)</li> <li><a href="/wiki/Vitamin_C" title="Vitamin C">Ascorbic acid</a> (C)</li> <li><a href="/wiki/Phytomenadione" title="Phytomenadione">Phylloquinone</a> (K<sub>1</sub>), <a href="/wiki/Vitamin_K" title="Vitamin K">Menaquinone</a> (K<sub>2</sub>)</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 class="mw-selflink selflink">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 / BH<sub>4</sub></a></li> <li><a href="/wiki/Tetrahydromethanopterin" title="Tetrahydromethanopterin">THMPT / H<sub>4</sub>MPT</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">Ca<sup>2+</sup></a></li> <li><a href="/wiki/Copper" title="Copper">Cu<sup>2+</sup></a></li> <li><a href="/wiki/Iron" title="Iron">Fe<sup>2+</sup>, Fe<sup>3+</sup></a></li> <li><a href="/wiki/Magnesium" title="Magnesium">Mg<sup>2+</sup></a></li> <li><a href="/wiki/Manganese" title="Manganese">Mn<sup>2+</sup></a></li> <li><a href="/wiki/Molybdenum" title="Molybdenum">Mo</a></li> <li><a href="/wiki/Nickel" title="Nickel">Ni<sup>2+</sup></a></li> <li><a href="/wiki/Zinc" title="Zinc">Zn<sup>2+</sup></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><i><a href="/wiki/Vitamin" title="Vitamin">vitamins</a></i>: <i>see <a href="/wiki/Template:Vitamins" title="Template:Vitamins">vitamins</a></i></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><style data-mw-deduplicate="TemplateStyles:r1038841319">.mw-parser-output .tooltip-dotted{border-bottom:1px dotted;cursor:help}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"></div><div role="navigation" class="navbox authority-control" aria-labelledby="Authority_control_databases_frameless&#124;text-top&#124;10px&#124;alt=Edit_this_at_Wikidata&#124;link=https&#58;//www.wikidata.org/wiki/Q189621#identifiers&#124;class=noprint&#124;Edit_this_at_Wikidata1314" style="padding:3px"><table class="nowraplinks hlist mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><div id="Authority_control_databases_frameless&#124;text-top&#124;10px&#124;alt=Edit_this_at_Wikidata&#124;link=https&#58;//www.wikidata.org/wiki/Q189621#identifiers&#124;class=noprint&#124;Edit_this_at_Wikidata1314" style="font-size:114%;margin:0 4em"><a href="/wiki/Help:Authority_control" title="Help:Authority control">Authority control databases</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q189621#identifiers" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">International</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"><ul><li><span class="uid"><a rel="nofollow" class="external text" href="http://id.worldcat.org/fast/954948/">FAST</a></span></li></ul></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">National</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"><ul><li><span class="uid"><a rel="nofollow" class="external text" href="https://d-nb.info/gnd/4244498-6">Germany</a></span></li><li><span class="uid"><a rel="nofollow" class="external text" href="https://id.loc.gov/authorities/sh85060147">United States</a></span></li><li><span class="uid"><a rel="nofollow" class="external text" href="https://catalogue.bnf.fr/ark:/12148/cb119813059">France</a></span></li><li><span class="uid"><a rel="nofollow" class="external text" href="https://data.bnf.fr/ark:/12148/cb119813059">BnF data</a></span></li><li><span class="uid"><a rel="nofollow" class="external text" href="https://www.nli.org.il/en/authorities/987007555531005171">Israel</a></span></li></ul></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"><ul><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="Hème"><a rel="nofollow" class="external text" href="https://www.idref.fr/02786183X">IdRef</a></span></span><ul><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="Hème"><a rel="nofollow" class="external text" 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