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class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Glycerophospholipids"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3</span> <span>Glycerophospholipids</span> </div> </a> <ul id="toc-Glycerophospholipids-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Sphingolipids" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Sphingolipids"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.4</span> <span>Sphingolipids</span> </div> </a> <ul id="toc-Sphingolipids-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Sterols" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Sterols"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.5</span> <span>Sterols</span> </div> </a> <ul id="toc-Sterols-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Prenols" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Prenols"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.6</span> <span>Prenols</span> </div> </a> <ul id="toc-Prenols-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Saccharolipids" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Saccharolipids"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.7</span> <span>Saccharolipids</span> </div> </a> <ul id="toc-Saccharolipids-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Polyketides" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Polyketides"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.8</span> <span>Polyketides</span> </div> </a> <ul id="toc-Polyketides-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Biological_functions" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Biological_functions"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Biological functions</span> </div> </a> <button aria-controls="toc-Biological_functions-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Biological functions subsection</span> </button> <ul id="toc-Biological_functions-sublist" class="vector-toc-list"> <li id="toc-Component_of_biological_membranes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Component_of_biological_membranes"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Component of biological membranes</span> </div> </a> <ul id="toc-Component_of_biological_membranes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Energy_storage" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Energy_storage"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Energy storage</span> </div> </a> <ul id="toc-Energy_storage-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Signaling" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Signaling"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span>Signaling</span> </div> </a> <ul id="toc-Signaling-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other_functions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Other_functions"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.4</span> <span>Other functions</span> </div> </a> <ul id="toc-Other_functions-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Metabolism" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Metabolism"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Metabolism</span> </div> </a> <button aria-controls="toc-Metabolism-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 Metabolism subsection</span> </button> <ul id="toc-Metabolism-sublist" class="vector-toc-list"> <li id="toc-Biosynthesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Biosynthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Biosynthesis</span> </div> </a> <ul id="toc-Biosynthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Degradation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Degradation"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Degradation</span> </div> </a> <ul id="toc-Degradation-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Nutrition_and_health" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Nutrition_and_health"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Nutrition and health</span> </div> </a> <ul id="toc-Nutrition_and_health-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>References</span> </div> </a> <button aria-controls="toc-References-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 References subsection</span> </button> <ul id="toc-References-sublist" class="vector-toc-list"> <li id="toc-Bibliography" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Bibliography"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.1</span> <span>Bibliography</span> </div> </a> <ul id="toc-Bibliography-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><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">Lipid</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 112 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-112" 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">112 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Lipied" title="Lipied – Afrikaans" lang="af" hreflang="af" data-title="Lipied" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target"><span>Afrikaans</span></a></li><li class="interlanguage-link interwiki-als mw-list-item"><a href="https://als.wikipedia.org/wiki/Lipide" title="Lipide – Alemannic" lang="gsw" hreflang="gsw" data-title="Lipide" data-language-autonym="Alemannisch" data-language-local-name="Alemannic" class="interlanguage-link-target"><span>Alemannisch</span></a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%84%D9%8A%D8%A8%D9%8A%D8%AF" title="ليبيد – Arabic" lang="ar" hreflang="ar" data-title="ليبيد" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-an mw-list-item"><a href="https://an.wikipedia.org/wiki/Lipido" title="Lipido – Aragonese" lang="an" hreflang="an" data-title="Lipido" data-language-autonym="Aragonés" data-language-local-name="Aragonese" class="interlanguage-link-target"><span>Aragonés</span></a></li><li class="interlanguage-link interwiki-as mw-list-item"><a href="https://as.wikipedia.org/wiki/%E0%A6%B2%E0%A6%BF%E0%A6%AA%E0%A6%BF%E0%A6%A1" title="লিপিড – Assamese" lang="as" hreflang="as" data-title="লিপিড" data-language-autonym="অসমীয়া" data-language-local-name="Assamese" class="interlanguage-link-target"><span>অসমীয়া</span></a></li><li class="interlanguage-link interwiki-ast mw-list-item"><a href="https://ast.wikipedia.org/wiki/L%C3%ADpidu" title="Lípidu – Asturian" lang="ast" hreflang="ast" data-title="Lípidu" data-language-autonym="Asturianu" data-language-local-name="Asturian" class="interlanguage-link-target"><span>Asturianu</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Lipidl%C9%99r" title="Lipidlər – Azerbaijani" lang="az" hreflang="az" data-title="Lipidlər" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D9%84%DB%8C%D9%BE%DB%8C%D8%AF" title="لیپید – South Azerbaijani" lang="azb" hreflang="azb" data-title="لیپید" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%B2%E0%A6%BF%E0%A6%AA%E0%A6%BF%E0%A6%A1" title="লিপিড – Bangla" lang="bn" hreflang="bn" data-title="লিপিড" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-ba mw-list-item"><a href="https://ba.wikipedia.org/wiki/%D0%9B%D0%B8%D0%BF%D0%B8%D0%B4%D1%82%D0%B0%D1%80" title="Липидтар – Bashkir" lang="ba" hreflang="ba" data-title="Липидтар" data-language-autonym="Башҡортса" data-language-local-name="Bashkir" class="interlanguage-link-target"><span>Башҡортса</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%9B%D1%96%D0%BF%D1%96%D0%B4%D1%8B" title="Ліпіды – Belarusian" lang="be" hreflang="be" data-title="Ліпіды" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-be-x-old mw-list-item"><a href="https://be-tarask.wikipedia.org/wiki/%D0%9B%D1%96%D0%BF%D1%96%D0%B4%D1%8B" title="Ліпіды – Belarusian (Taraškievica orthography)" lang="be-tarask" hreflang="be-tarask" data-title="Ліпіды" data-language-autonym="Беларуская (тарашкевіца)" data-language-local-name="Belarusian (Taraškievica orthography)" class="interlanguage-link-target"><span>Беларуская (тарашкевіца)</span></a></li><li class="interlanguage-link interwiki-bcl mw-list-item"><a href="https://bcl.wikipedia.org/wiki/Lipid" title="Lipid – Central Bikol" lang="bcl" hreflang="bcl" data-title="Lipid" data-language-autonym="Bikol Central" data-language-local-name="Central Bikol" class="interlanguage-link-target"><span>Bikol Central</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%9B%D0%B8%D0%BF%D0%B8%D0%B4" title="Липид – Bulgarian" lang="bg" hreflang="bg" data-title="Липид" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Lipidi" title="Lipidi – Bosnian" lang="bs" hreflang="bs" data-title="Lipidi" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-br mw-list-item"><a href="https://br.wikipedia.org/wiki/Lipid" title="Lipid – Breton" lang="br" hreflang="br" data-title="Lipid" data-language-autonym="Brezhoneg" data-language-local-name="Breton" class="interlanguage-link-target"><span>Brezhoneg</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/L%C3%ADpid" title="Lípid – Catalan" lang="ca" hreflang="ca" data-title="Lípid" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-ceb mw-list-item"><a href="https://ceb.wikipedia.org/wiki/Lipid" title="Lipid – Cebuano" lang="ceb" hreflang="ceb" data-title="Lipid" data-language-autonym="Cebuano" data-language-local-name="Cebuano" class="interlanguage-link-target"><span>Cebuano</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Lipidy" title="Lipidy – Czech" lang="cs" hreflang="cs" data-title="Lipidy" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Lipid" title="Lipid – Welsh" lang="cy" hreflang="cy" data-title="Lipid" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target"><span>Cymraeg</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Lipid" title="Lipid – Danish" lang="da" hreflang="da" data-title="Lipid" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-ary mw-list-item"><a href="https://ary.wikipedia.org/wiki/%D9%84%D9%8A%D9%BE%D9%8A%D8%AF" title="ليپيد – Moroccan Arabic" lang="ary" hreflang="ary" data-title="ليپيد" data-language-autonym="الدارجة" data-language-local-name="Moroccan Arabic" class="interlanguage-link-target"><span>الدارجة</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Lipide" title="Lipide – German" lang="de" hreflang="de" data-title="Lipide" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-dv mw-list-item"><a href="https://dv.wikipedia.org/wiki/%DE%8A%DE%AC%DE%93%DE%B0" title="ފެޓް – Divehi" lang="dv" hreflang="dv" data-title="ފެޓް" data-language-autonym="ދިވެހިބަސް" data-language-local-name="Divehi" class="interlanguage-link-target"><span>ދިވެހިބަސް</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Lipiidid" title="Lipiidid – Estonian" lang="et" hreflang="et" data-title="Lipiidid" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%9B%CE%B9%CF%80%CE%AF%CE%B4%CE%B9%CE%BF" title="Λιπίδιο – Greek" lang="el" hreflang="el" data-title="Λιπίδιο" 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/L%C3%ADpido" title="Lípido – Spanish" lang="es" hreflang="es" data-title="Lípido" 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/Lipido" title="Lipido – Esperanto" lang="eo" hreflang="eo" data-title="Lipido" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-ext mw-list-item"><a href="https://ext.wikipedia.org/wiki/L%C3%ADpiu" title="Lípiu – Extremaduran" lang="ext" hreflang="ext" data-title="Lípiu" data-language-autonym="Estremeñu" data-language-local-name="Extremaduran" class="interlanguage-link-target"><span>Estremeñu</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Lipido" title="Lipido – Basque" lang="eu" hreflang="eu" data-title="Lipido" 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%84%DB%8C%D9%BE%DB%8C%D8%AF" title="لیپید – Persian" lang="fa" hreflang="fa" data-title="لیپید" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-hif mw-list-item"><a href="https://hif.wikipedia.org/wiki/Lipid" title="Lipid – Fiji Hindi" lang="hif" hreflang="hif" data-title="Lipid" data-language-autonym="Fiji Hindi" data-language-local-name="Fiji Hindi" class="interlanguage-link-target"><span>Fiji Hindi</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Lipide" title="Lipide – French" lang="fr" hreflang="fr" data-title="Lipide" 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/Lipid%C3%AD" title="Lipidí – Irish" lang="ga" hreflang="ga" data-title="Lipidí" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-gl badge-Q17437798 badge-goodarticle mw-list-item" title="good article badge"><a href="https://gl.wikipedia.org/wiki/L%C3%ADpido" title="Lípido – Galician" lang="gl" hreflang="gl" data-title="Lípido" 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/%EC%A7%80%EC%A7%88_(%EC%83%9D%EB%AC%BC%ED%95%99)" title="지질 (생물학) – Korean" lang="ko" hreflang="ko" data-title="지질 (생물학)" 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/%D4%BC%D5%AB%D5%BA%D5%AB%D5%A4" title="Լիպիդ – Armenian" lang="hy" hreflang="hy" data-title="Լիպիդ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%B2%E0%A4%BF%E0%A4%AA%E0%A4%BF%E0%A4%A1" title="लिपिड – Hindi" lang="hi" hreflang="hi" data-title="लिपिड" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Lipidi" title="Lipidi – Croatian" lang="hr" hreflang="hr" data-title="Lipidi" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Lipida" title="Lipida – Indonesian" lang="id" hreflang="id" data-title="Lipida" 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-ia mw-list-item"><a href="https://ia.wikipedia.org/wiki/Lipido" title="Lipido – Interlingua" lang="ia" hreflang="ia" data-title="Lipido" data-language-autonym="Interlingua" data-language-local-name="Interlingua" class="interlanguage-link-target"><span>Interlingua</span></a></li><li class="interlanguage-link interwiki-is mw-list-item"><a href="https://is.wikipedia.org/wiki/Fita" title="Fita – Icelandic" lang="is" hreflang="is" data-title="Fita" data-language-autonym="Íslenska" data-language-local-name="Icelandic" class="interlanguage-link-target"><span>Íslenska</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Lipidi" title="Lipidi – Italian" lang="it" hreflang="it" data-title="Lipidi" 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%9C%D7%99%D7%A4%D7%99%D7%93" title="ליפיד – Hebrew" lang="he" hreflang="he" data-title="ליפיד" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-jv mw-list-item"><a href="https://jv.wikipedia.org/wiki/Gajih" title="Gajih – Javanese" lang="jv" hreflang="jv" data-title="Gajih" data-language-autonym="Jawa" data-language-local-name="Javanese" class="interlanguage-link-target"><span>Jawa</span></a></li><li class="interlanguage-link interwiki-pam mw-list-item"><a href="https://pam.wikipedia.org/wiki/Lipid" title="Lipid – Pampanga" lang="pam" hreflang="pam" data-title="Lipid" data-language-autonym="Kapampangan" data-language-local-name="Pampanga" class="interlanguage-link-target"><span>Kapampangan</span></a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%9A%E1%83%98%E1%83%9E%E1%83%98%E1%83%93%E1%83%94%E1%83%91%E1%83%98" title="ლიპიდები – Georgian" lang="ka" hreflang="ka" data-title="ლიპიდები" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%9B%D0%B8%D0%BF%D0%B8%D0%B4%D1%82%D0%B5%D1%80" title="Липидтер – Kazakh" lang="kk" hreflang="kk" data-title="Липидтер" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-kw mw-list-item"><a href="https://kw.wikipedia.org/wiki/Lipid" title="Lipid – Cornish" lang="kw" hreflang="kw" data-title="Lipid" data-language-autonym="Kernowek" data-language-local-name="Cornish" class="interlanguage-link-target"><span>Kernowek</span></a></li><li class="interlanguage-link interwiki-sw mw-list-item"><a href="https://sw.wikipedia.org/wiki/Lipidi" title="Lipidi – Swahili" lang="sw" hreflang="sw" data-title="Lipidi" data-language-autonym="Kiswahili" data-language-local-name="Swahili" class="interlanguage-link-target"><span>Kiswahili</span></a></li><li class="interlanguage-link interwiki-ht mw-list-item"><a href="https://ht.wikipedia.org/wiki/Lipid" title="Lipid – Haitian Creole" lang="ht" hreflang="ht" data-title="Lipid" data-language-autonym="Kreyòl ayisyen" data-language-local-name="Haitian Creole" class="interlanguage-link-target"><span>Kreyòl ayisyen</span></a></li><li class="interlanguage-link interwiki-ku mw-list-item"><a href="https://ku.wikipedia.org/wiki/L%C3%AEp%C3%AEd" title="Lîpîd – Kurdish" lang="ku" hreflang="ku" data-title="Lîpîd" data-language-autonym="Kurdî" data-language-local-name="Kurdish" class="interlanguage-link-target"><span>Kurdî</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%9B%D0%B8%D0%BF%D0%B8%D0%B4" title="Липид – Kyrgyz" lang="ky" hreflang="ky" data-title="Липид" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-lo mw-list-item"><a href="https://lo.wikipedia.org/wiki/%E0%BB%84%E0%BA%82%E0%BA%A1%E0%BA%B1%E0%BA%99" title="ໄຂມັນ – Lao" lang="lo" hreflang="lo" data-title="ໄຂມັນ" data-language-autonym="ລາວ" data-language-local-name="Lao" class="interlanguage-link-target"><span>ລາວ</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Lipidum" title="Lipidum – Latin" lang="la" hreflang="la" data-title="Lipidum" data-language-autonym="Latina" data-language-local-name="Latin" class="interlanguage-link-target"><span>Latina</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Lip%C4%ABdi" title="Lipīdi – Latvian" lang="lv" hreflang="lv" data-title="Lipīdi" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-lb mw-list-item"><a href="https://lb.wikipedia.org/wiki/Lipid" title="Lipid – Luxembourgish" lang="lb" hreflang="lb" data-title="Lipid" data-language-autonym="Lëtzebuergesch" data-language-local-name="Luxembourgish" class="interlanguage-link-target"><span>Lëtzebuergesch</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Lipidai" title="Lipidai – Lithuanian" lang="lt" hreflang="lt" data-title="Lipidai" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-lmo mw-list-item"><a href="https://lmo.wikipedia.org/wiki/Lipid" title="Lipid – Lombard" lang="lmo" hreflang="lmo" data-title="Lipid" data-language-autonym="Lombard" data-language-local-name="Lombard" class="interlanguage-link-target"><span>Lombard</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Lipidek" title="Lipidek – Hungarian" lang="hu" hreflang="hu" data-title="Lipidek" 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%9B%D0%B8%D0%BF%D0%B8%D0%B4" title="Липид – Macedonian" lang="mk" hreflang="mk" data-title="Липид" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-mg mw-list-item"><a href="https://mg.wikipedia.org/wiki/Lipida" title="Lipida – Malagasy" lang="mg" hreflang="mg" data-title="Lipida" data-language-autonym="Malagasy" data-language-local-name="Malagasy" class="interlanguage-link-target"><span>Malagasy</span></a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%B2%E0%B4%BF%E0%B4%AA%E0%B5%8D%E0%B4%AA%E0%B4%BF%E0%B4%A1%E0%B5%8D" title="ലിപ്പിഡ് – Malayalam" lang="ml" hreflang="ml" data-title="ലിപ്പിഡ്" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Lipid" title="Lipid – Malay" lang="ms" hreflang="ms" data-title="Lipid" 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-fj mw-list-item"><a href="https://fj.wikipedia.org/wiki/Lipid" title="Lipid – Fijian" lang="fj" hreflang="fj" data-title="Lipid" data-language-autonym="Na Vosa Vakaviti" data-language-local-name="Fijian" class="interlanguage-link-target"><span>Na Vosa Vakaviti</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Lipide" title="Lipide – Dutch" lang="nl" hreflang="nl" data-title="Lipide" 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/%E8%84%82%E8%B3%AA" title="脂質 – Japanese" lang="ja" hreflang="ja" data-title="脂質" 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/Lipid" title="Lipid – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Lipid" 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/Lipid" title="Lipid – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Lipid" data-language-autonym="Norsk nynorsk" data-language-local-name="Norwegian Nynorsk" class="interlanguage-link-target"><span>Norsk nynorsk</span></a></li><li class="interlanguage-link interwiki-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Lipid" title="Lipid – Occitan" lang="oc" hreflang="oc" data-title="Lipid" data-language-autonym="Occitan" data-language-local-name="Occitan" class="interlanguage-link-target"><span>Occitan</span></a></li><li class="interlanguage-link interwiki-or mw-list-item"><a href="https://or.wikipedia.org/wiki/%E0%AC%B8%E0%AD%8D%E0%AC%A8%E0%AD%87%E0%AC%B9%E0%AC%B8%E0%AC%BE%E0%AC%B0" title="ସ୍ନେହସାର – Odia" lang="or" hreflang="or" data-title="ସ୍ନେହସାର" data-language-autonym="ଓଡ଼ିଆ" data-language-local-name="Odia" class="interlanguage-link-target"><span>ଓଡ଼ିଆ</span></a></li><li class="interlanguage-link interwiki-om mw-list-item"><a href="https://om.wikipedia.org/wiki/Suuphana" title="Suuphana – Oromo" lang="om" hreflang="om" data-title="Suuphana" data-language-autonym="Oromoo" data-language-local-name="Oromo" class="interlanguage-link-target"><span>Oromoo</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Lipidlar" title="Lipidlar – Uzbek" lang="uz" hreflang="uz" data-title="Lipidlar" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-pa mw-list-item"><a href="https://pa.wikipedia.org/wiki/%E0%A8%B5%E0%A8%B8%E0%A8%BE" title="ਵਸਾ – Punjabi" lang="pa" hreflang="pa" data-title="ਵਸਾ" data-language-autonym="ਪੰਜਾਬੀ" data-language-local-name="Punjabi" class="interlanguage-link-target"><span>ਪੰਜਾਬੀ</span></a></li><li class="interlanguage-link interwiki-pnb mw-list-item"><a href="https://pnb.wikipedia.org/wiki/%D9%84%D9%BE%DA%88" title="لپڈ – Western Punjabi" lang="pnb" hreflang="pnb" data-title="لپڈ" data-language-autonym="پنجابی" data-language-local-name="Western Punjabi" class="interlanguage-link-target"><span>پنجابی</span></a></li><li class="interlanguage-link interwiki-ps mw-list-item"><a href="https://ps.wikipedia.org/wiki/%D8%BA%D9%88%DA%93" title="غوړ – Pashto" lang="ps" hreflang="ps" data-title="غوړ" data-language-autonym="پښتو" data-language-local-name="Pashto" class="interlanguage-link-target"><span>پښتو</span></a></li><li class="interlanguage-link interwiki-nds mw-list-item"><a href="https://nds.wikipedia.org/wiki/Lipid" title="Lipid – Low German" lang="nds" hreflang="nds" data-title="Lipid" data-language-autonym="Plattdüütsch" data-language-local-name="Low German" class="interlanguage-link-target"><span>Plattdüütsch</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Lipidy" title="Lipidy – Polish" lang="pl" hreflang="pl" data-title="Lipidy" 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/L%C3%ADpido" title="Lípido – Portuguese" lang="pt" hreflang="pt" data-title="Lípido" 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/Lipid%C4%83" title="Lipidă – Romanian" lang="ro" hreflang="ro" data-title="Lipidă" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-rue mw-list-item"><a href="https://rue.wikipedia.org/wiki/%D0%9B%D1%96%D0%BF%D1%96%D0%B4%D1%8B" title="Ліпіды – Rusyn" lang="rue" hreflang="rue" data-title="Ліпіды" data-language-autonym="Русиньскый" data-language-local-name="Rusyn" class="interlanguage-link-target"><span>Русиньскый</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%9B%D0%B8%D0%BF%D0%B8%D0%B4%D1%8B" title="Липиды – Russian" lang="ru" hreflang="ru" data-title="Липиды" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sah mw-list-item"><a href="https://sah.wikipedia.org/wiki/%D0%9B%D0%B8%D0%BF%D0%B8%D0%B8%D1%82%D1%82%D1%8D%D1%80" title="Липииттэр – Yakut" lang="sah" hreflang="sah" data-title="Липииттэр" data-language-autonym="Саха тыла" data-language-local-name="Yakut" class="interlanguage-link-target"><span>Саха тыла</span></a></li><li class="interlanguage-link interwiki-sco mw-list-item"><a href="https://sco.wikipedia.org/wiki/Lipid" title="Lipid – Scots" lang="sco" hreflang="sco" data-title="Lipid" data-language-autonym="Scots" data-language-local-name="Scots" class="interlanguage-link-target"><span>Scots</span></a></li><li class="interlanguage-link interwiki-sq mw-list-item"><a href="https://sq.wikipedia.org/wiki/Lipidet" title="Lipidet – Albanian" lang="sq" hreflang="sq" data-title="Lipidet" data-language-autonym="Shqip" data-language-local-name="Albanian" class="interlanguage-link-target"><span>Shqip</span></a></li><li class="interlanguage-link interwiki-scn mw-list-item"><a href="https://scn.wikipedia.org/wiki/Lipidi" title="Lipidi – Sicilian" lang="scn" hreflang="scn" data-title="Lipidi" data-language-autonym="Sicilianu" data-language-local-name="Sicilian" class="interlanguage-link-target"><span>Sicilianu</span></a></li><li class="interlanguage-link interwiki-si mw-list-item"><a href="https://si.wikipedia.org/wiki/%E0%B6%BD%E0%B7%92%E0%B6%B4%E0%B7%92%E0%B6%A9" title="ලිපිඩ – Sinhala" lang="si" hreflang="si" data-title="ලිපිඩ" data-language-autonym="සිංහල" data-language-local-name="Sinhala" class="interlanguage-link-target"><span>සිංහල</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Lipid" title="Lipid – Simple English" lang="en-simple" hreflang="en-simple" data-title="Lipid" 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/Lipid" title="Lipid – Slovak" lang="sk" hreflang="sk" data-title="Lipid" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl badge-Q17437796 badge-featuredarticle mw-list-item" title="featured article badge"><a href="https://sl.wikipedia.org/wiki/Lipid" title="Lipid – Slovenian" lang="sl" hreflang="sl" data-title="Lipid" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-so mw-list-item"><a href="https://so.wikipedia.org/wiki/Baruur" title="Baruur – Somali" lang="so" hreflang="so" data-title="Baruur" data-language-autonym="Soomaaliga" data-language-local-name="Somali" class="interlanguage-link-target"><span>Soomaaliga</span></a></li><li class="interlanguage-link interwiki-ckb mw-list-item"><a href="https://ckb.wikipedia.org/wiki/%D9%84%DB%8C%D9%BE%DB%8C%D8%AF" title="لیپید – Central Kurdish" lang="ckb" hreflang="ckb" data-title="لیپید" data-language-autonym="کوردی" data-language-local-name="Central Kurdish" class="interlanguage-link-target"><span>کوردی</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%9B%D0%B8%D0%BF%D0%B8%D0%B4" title="Липид – Serbian" lang="sr" hreflang="sr" data-title="Липид" 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/Lipidi" title="Lipidi – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Lipidi" 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-su mw-list-item"><a href="https://su.wikipedia.org/wiki/Lipid" title="Lipid – Sundanese" lang="su" hreflang="su" data-title="Lipid" data-language-autonym="Sunda" data-language-local-name="Sundanese" class="interlanguage-link-target"><span>Sunda</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Lipidi" title="Lipidi – Finnish" lang="fi" hreflang="fi" data-title="Lipidi" 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/Lipid" title="Lipid – Swedish" lang="sv" hreflang="sv" data-title="Lipid" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-tl mw-list-item"><a href="https://tl.wikipedia.org/wiki/Lipido" title="Lipido – Tagalog" lang="tl" hreflang="tl" data-title="Lipido" data-language-autonym="Tagalog" data-language-local-name="Tagalog" class="interlanguage-link-target"><span>Tagalog</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%95%E0%AF%8A%E0%AE%B4%E0%AF%81%E0%AE%AE%E0%AE%BF%E0%AE%AF%E0%AE%AE%E0%AF%8D" title="கொழுமியம் – Tamil" lang="ta" hreflang="ta" data-title="கொழுமியம்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-te mw-list-item"><a href="https://te.wikipedia.org/wiki/%E0%B0%95%E0%B1%8A%E0%B0%B5%E0%B1%8D%E0%B0%B5%E0%B1%81_%E0%B0%AA%E0%B0%A6%E0%B0%BE%E0%B0%B0%E0%B1%8D%E0%B0%A7%E0%B0%BE%E0%B0%B2%E0%B1%81" title="కొవ్వు పదార్ధాలు – Telugu" lang="te" hreflang="te" data-title="కొవ్వు పదార్ధాలు" data-language-autonym="తెలుగు" data-language-local-name="Telugu" class="interlanguage-link-target"><span>తెలుగు</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B8%A5%E0%B8%B4%E0%B8%9E%E0%B8%B4%E0%B8%94" title="ลิพิด – Thai" lang="th" hreflang="th" data-title="ลิพิด" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Lipit" title="Lipit – Turkish" lang="tr" hreflang="tr" data-title="Lipit" 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%9B%D1%96%D0%BF%D1%96%D0%B4%D0%B8" title="Ліпіди – Ukrainian" lang="uk" hreflang="uk" data-title="Ліпіди" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-ur mw-list-item"><a href="https://ur.wikipedia.org/wiki/%D8%B4%D8%AD%D9%85%DB%8C%D8%A7%D8%AA" title="شحمیات – Urdu" lang="ur" hreflang="ur" data-title="شحمیات" data-language-autonym="اردو" data-language-local-name="Urdu" class="interlanguage-link-target"><span>اردو</span></a></li><li class="interlanguage-link interwiki-vec mw-list-item"><a href="https://vec.wikipedia.org/wiki/Lipidi" title="Lipidi – Venetian" lang="vec" hreflang="vec" data-title="Lipidi" data-language-autonym="Vèneto" data-language-local-name="Venetian" class="interlanguage-link-target"><span>Vèneto</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Lipid" title="Lipid – Vietnamese" lang="vi" hreflang="vi" data-title="Lipid" 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-war mw-list-item"><a href="https://war.wikipedia.org/wiki/Lipido" title="Lipido – Waray" lang="war" hreflang="war" data-title="Lipido" data-language-autonym="Winaray" data-language-local-name="Waray" class="interlanguage-link-target"><span>Winaray</span></a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E8%84%82%E7%B1%BB" title="脂类 – Wu" lang="wuu" hreflang="wuu" data-title="脂类" data-language-autonym="吴语" data-language-local-name="Wu" class="interlanguage-link-target"><span>吴语</span></a></li><li class="interlanguage-link interwiki-yi mw-list-item"><a href="https://yi.wikipedia.org/wiki/%D7%9C%D7%99%D7%A4%D7%99%D7%93" title="ליפיד – Yiddish" lang="yi" hreflang="yi" data-title="ליפיד" data-language-autonym="ייִדיש" data-language-local-name="Yiddish" class="interlanguage-link-target"><span>ייִדיש</span></a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E8%84%82" title="脂 – Cantonese" lang="yue" hreflang="yue" data-title="脂" 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</div> </div> </div> </nav> </div> </div> </div> <div class="vector-column-end"> <div class="vector-sticky-pinned-container"> <nav class="vector-page-tools-landmark" aria-label="Page tools"> <div id="vector-page-tools-pinned-container" class="vector-pinned-container"> </div> </nav> <nav class="vector-appearance-landmark" aria-label="Appearance"> <div id="vector-appearance-pinned-container" class="vector-pinned-container"> <div id="vector-appearance" class="vector-appearance vector-pinnable-element"> <div class="vector-pinnable-header vector-appearance-pinnable-header vector-pinnable-header-pinned" data-feature-name="appearance-pinned" data-pinnable-element-id="vector-appearance" data-pinned-container-id="vector-appearance-pinned-container" data-unpinned-container-id="vector-appearance-unpinned-container" > <div class="vector-pinnable-header-label">Appearance</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" 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is soluble in nonpolar solvents</div> <p class="mw-empty-elt"> </p> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Common_lipid_types.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5a/Common_lipid_types.svg/450px-Common_lipid_types.svg.png" decoding="async" width="450" height="497" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5a/Common_lipid_types.svg/675px-Common_lipid_types.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5a/Common_lipid_types.svg/900px-Common_lipid_types.svg.png 2x" data-file-width="1630" data-file-height="1800" /></a><figcaption>Structures of some common lipids. At the top are <a href="/wiki/Cholesterol" title="Cholesterol">cholesterol</a><sup id="cite_ref-Maitland_1998_1-0" class="reference"><a href="#cite_note-Maitland_1998-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Oleic_acid" title="Oleic acid">oleic acid</a>.<sup id="cite_ref-Stryer_2007_2-0" class="reference"><a href="#cite_note-Stryer_2007-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 328">: 328 </span></sup> The middle structure is a <a href="/wiki/Triglyceride" title="Triglyceride">triglyceride</a> composed of <a href="/wiki/Oleate" class="mw-redirect" title="Oleate">oleoyl</a>, <a href="/wiki/Stearic_acid" title="Stearic acid">stearoyl</a>, and <a href="/wiki/Palmitate" class="mw-redirect" title="Palmitate">palmitoyl</a> chains attached to a <a href="/wiki/Glycerol" title="Glycerol">glycerol</a> backbone. At the bottom is the common <a href="/wiki/Phospholipid" title="Phospholipid">phospholipid</a> <a href="/wiki/Phosphatidylcholine" title="Phosphatidylcholine">phosphatidylcholine</a>.</figcaption></figure> <p><b>Lipids</b> are a broad group of organic compounds which include <a href="/wiki/Fat" title="Fat">fats</a>, <a href="/wiki/Wax" title="Wax">waxes</a>, <a href="/wiki/Sterol" title="Sterol">sterols</a>, <a href="/wiki/Fat-soluble_vitamin" class="mw-redirect" title="Fat-soluble vitamin">fat-soluble vitamins</a> (such as vitamins <a href="/wiki/Vitamin_A" title="Vitamin A">A</a>, <a href="/wiki/Vitamin_D" title="Vitamin D">D</a>, <a href="/wiki/Vitamin_E" title="Vitamin E">E</a> and <a href="/wiki/Vitamin_K" title="Vitamin K">K</a>), <a href="/wiki/Monoglyceride" title="Monoglyceride">monoglycerides</a>, <a href="/wiki/Diglyceride" title="Diglyceride">diglycerides</a>, <a href="/wiki/Phospholipid" title="Phospholipid">phospholipids</a>, and others. The functions of lipids include storing energy, <a href="/wiki/Lipid_signaling" title="Lipid signaling">signaling</a>, and acting as structural components of <a href="/wiki/Cell_membrane" title="Cell membrane">cell membranes</a>.<sup id="cite_ref-Fahy_2009_3-0" class="reference"><a href="#cite_note-Fahy_2009-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Subramaniam_2011_4-0" class="reference"><a href="#cite_note-Subramaniam_2011-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Lipids have applications in the <a href="/wiki/Cosmetic_industry" title="Cosmetic industry">cosmetic</a> and <a href="/wiki/Food_industry" title="Food industry">food industries</a>, and in <a href="/wiki/Nanotechnology" title="Nanotechnology">nanotechnology</a>.<sup id="cite_ref-Mashaghi_2013_5-0" class="reference"><a href="#cite_note-Mashaghi_2013-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>Lipids may be broadly defined as <a href="/wiki/Hydrophobe" title="Hydrophobe">hydrophobic</a> or <a href="/wiki/Amphiphile" title="Amphiphile">amphiphilic</a> small molecules; the amphiphilic nature of some lipids allows them to form structures such as <a href="/wiki/Vesicle_(biology)" class="mw-redirect" title="Vesicle (biology)">vesicles</a>, multilamellar/<a href="/wiki/Unilamellar_liposome" title="Unilamellar liposome">unilamellar liposomes</a>, or membranes in an aqueous environment. Biological lipids originate entirely or in part from two distinct types of biochemical subunits or "building-blocks": <a href="https://en.wiktionary.org/wiki/ketoacyl" class="extiw" title="wikt:ketoacyl">ketoacyl</a> and <a href="/wiki/Isoprene" title="Isoprene">isoprene</a> groups.<sup id="cite_ref-Fahy_2009_3-1" class="reference"><a href="#cite_note-Fahy_2009-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Using this approach, lipids may be divided into eight categories: <a href="/wiki/Fatty_acid" title="Fatty acid">fatty acyls</a>, <a href="/wiki/Glycerolipid" class="mw-redirect" title="Glycerolipid">glycerolipids</a>, <a href="/wiki/Glycerophospholipid" title="Glycerophospholipid">glycerophospholipids</a>, <a href="/wiki/Sphingolipid" title="Sphingolipid">sphingolipids</a>, <a href="/wiki/Saccharolipid" title="Saccharolipid">saccharolipids</a>, and <a href="/wiki/Polyketide" title="Polyketide">polyketides</a> (derived from condensation of ketoacyl subunits); and sterol lipids and prenol lipids (derived from condensation of isoprene subunits).<sup id="cite_ref-Fahy_2009_3-2" class="reference"><a href="#cite_note-Fahy_2009-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>Although the term "lipid" is sometimes used as a synonym for fats, fats are a subgroup of lipids called <a href="/wiki/Triglyceride" title="Triglyceride">triglycerides</a>. Lipids also encompass molecules such as <a href="/wiki/Fatty_acid" title="Fatty acid">fatty acids</a> and their derivatives (including tri-, di-, monoglycerides, and phospholipids), as well as other <a href="/wiki/Sterol" title="Sterol">sterol</a>-containing <a href="/wiki/Metabolite" title="Metabolite">metabolites</a> such as <a href="/wiki/Cholesterol" title="Cholesterol">cholesterol</a>.<sup id="cite_ref-Michelle_1993_6-0" class="reference"><a href="#cite_note-Michelle_1993-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Although humans and other mammals use various <a href="/wiki/Metabolism" title="Metabolism">biosynthetic pathways</a> both to break down and to synthesize lipids, some essential lipids cannot be made this way and must be obtained from the diet. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lipid&action=edit&section=1" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In 1815, <a href="/wiki/Henri_Braconnot" title="Henri Braconnot">Henri Braconnot</a> classified lipids (<i>graisses</i>) in two categories, <i>suifs</i> (solid greases or tallow) and <i>huiles</i> (fluid oils).<sup id="cite_ref-Braconnot_1815_7-0" class="reference"><a href="#cite_note-Braconnot_1815-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> In 1823, <a href="/wiki/Michel_Eug%C3%A8ne_Chevreul" title="Michel Eugène Chevreul">Michel Eugène Chevreul</a> developed a more detailed classification, including oils, greases, tallow, waxes, resins, balsams and volatile oils (or essential oils).<sup id="cite_ref-Chevreul_1823_8-0" class="reference"><a href="#cite_note-Chevreul_1823-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Leray_2012_9-0" class="reference"><a href="#cite_note-Leray_2012-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Leray_2015_10-0" class="reference"><a href="#cite_note-Leray_2015-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p><p>The first synthetic triglyceride was reported by <a href="/wiki/Th%C3%A9ophile-Jules_Pelouze" title="Théophile-Jules Pelouze">Théophile-Jules Pelouze</a> in 1844, when he produced <a href="/wiki/Tributyrin" title="Tributyrin">tributyrin</a> by treating <a href="/wiki/Butyric_acid" title="Butyric acid">butyric acid</a> with <a href="/wiki/Glycerin" class="mw-redirect" title="Glycerin">glycerin</a> in the presence of concentrated <a href="/wiki/Sulfuric_acid" title="Sulfuric acid">sulfuric acid</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> Several years later, <a href="/wiki/Marcellin_Berthelot" title="Marcellin Berthelot">Marcellin Berthelot</a>, one of Pelouze's students, synthesized <a href="/wiki/Tristearin" class="mw-redirect" title="Tristearin">tristearin</a> and <a href="/wiki/Tripalmitin" title="Tripalmitin">tripalmitin</a> by reaction of the analogous <a href="/wiki/Fatty_acid" title="Fatty acid">fatty acids</a> with glycerin in the presence of gaseous <a href="/wiki/Hydrogen_chloride" title="Hydrogen chloride">hydrogen chloride</a> at high temperature.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p><p>In 1827, <a href="/wiki/William_Prout" title="William Prout">William Prout</a> recognized fat ("oily" alimentary matters), along with protein ("albuminous") and carbohydrate ("saccharine"), as an important nutrient for humans and animals.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p><p>For a century, chemists regarded "fats" as only simple lipids made of fatty acids and glycerol (glycerides), but new forms were described later. <a href="/wiki/Theodore_Nicolas_Gobley" class="mw-redirect" title="Theodore Nicolas Gobley">Theodore Gobley</a> (1847) discovered phospholipids in mammalian brain and hen egg, called by him as "<a href="/wiki/Lecithin" title="Lecithin">lecithins</a>". <a href="/wiki/Johann_Ludwig_Wilhelm_Thudichum" title="Johann Ludwig Wilhelm Thudichum">Thudichum</a> discovered in human brain some phospholipids (<a href="/wiki/Cephalin" class="mw-redirect" title="Cephalin">cephalin</a>), glycolipids (<a href="/wiki/Cerebroside" title="Cerebroside">cerebroside</a>) and sphingolipids (<a href="/wiki/Sphingomyelin" title="Sphingomyelin">sphingomyelin</a>).<sup id="cite_ref-Leray_2012_9-1" class="reference"><a href="#cite_note-Leray_2012-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>The terms lipoid, lipin, lipide and lipid have been used with varied meanings from author to author.<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> In 1912, Rosenbloom and <a href="/wiki/William_John_Gies" title="William John Gies">Gies</a> proposed the substitution of "lipoid" by "lipin".<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> In 1920, Bloor introduced a new classification for "lipoids": simple lipoids (greases and waxes), compound lipoids (phospholipoids and glycolipoids), and the derived lipoids (fatty acids, <a href="/wiki/Alcohols" class="mw-redirect" title="Alcohols">alcohols</a>, sterols).<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><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><p>The word <i>lipide</i>, which stems etymologically from Greek λίπος, <i>lipos</i> 'fat', was introduced in 1923 by the French pharmacologist <a href="/wiki/Gabriel_Bertrand" title="Gabriel Bertrand">Gabriel Bertrand</a>.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> Bertrand included in the concept not only the traditional fats (glycerides), but also the "lipoids", with a complex constitution.<sup id="cite_ref-Leray_2012_9-2" class="reference"><a href="#cite_note-Leray_2012-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> The word <i>lipide</i> was unanimously approved by the international commission of the <i>Société de Chimie Biologique</i> during the plenary session on July 3, 1923. The word <i>lipide</i> was later anglicized as <i>lipid</i> because of its pronunciation ('lɪpɪd). In French, the suffix <i>-ide</i>, from Ancient Greek -ίδης (meaning 'son of' or 'descendant of'), is always pronounced (ɪd). </p><p>In 1947, <a href="https://de.wikipedia.org/wiki/Thomas_Percy_Hilditch" class="extiw" title="de:Thomas Percy Hilditch">T. P. Hilditch</a> defined "simple lipids" as greases and waxes (true waxes, sterols, alcohols).<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><sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citing_sources" title="Wikipedia:Citing sources"><span title="This citation requires a reference to the specific page or range of pages in which the material appears. (April 2024)">page needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading2"><h2 id="Categories">Categories</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lipid&action=edit&section=2" title="Edit section: Categories"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Lipids have been classified into eight categories by the <a href="/wiki/LIPID_MAPS" title="LIPID MAPS">Lipid MAPS</a> consortium<sup id="cite_ref-Fahy_2009_3-3" class="reference"><a href="#cite_note-Fahy_2009-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> as follows: </p> <div class="mw-heading mw-heading3"><h3 id="Fatty_acyls">Fatty acyls</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lipid&action=edit&section=3" title="Edit section: Fatty acyls"><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/Fatty_acid" title="Fatty acid">Fatty acid</a></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Prostacyclin-2D-skeletal.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3f/Prostacyclin-2D-skeletal.png/220px-Prostacyclin-2D-skeletal.png" decoding="async" width="220" height="273" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3f/Prostacyclin-2D-skeletal.png/330px-Prostacyclin-2D-skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3f/Prostacyclin-2D-skeletal.png/440px-Prostacyclin-2D-skeletal.png 2x" data-file-width="1614" data-file-height="2000" /></a><figcaption><a href="/wiki/Prostacyclin" title="Prostacyclin">I<sub>2</sub> – Prostacyclin</a> (an example of a <a href="/wiki/Prostaglandin" title="Prostaglandin">prostaglandin</a>, an eicosanoid fatty acid)</figcaption></figure> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Leukotriene_B4.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/77/Leukotriene_B4.svg/220px-Leukotriene_B4.svg.png" decoding="async" width="220" height="67" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/77/Leukotriene_B4.svg/330px-Leukotriene_B4.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/77/Leukotriene_B4.svg/440px-Leukotriene_B4.svg.png 2x" data-file-width="420" data-file-height="128" /></a><figcaption><a href="/wiki/Leukotriene_B4" title="Leukotriene B4">LTB<sub>4</sub></a> (an example of a <a href="/wiki/Leukotriene" title="Leukotriene">leukotriene</a>, an eicosanoid fatty acid)</figcaption></figure> <p>Fatty acyls, a generic term for describing fatty acids, their conjugates and derivatives, are a diverse group of molecules synthesized by chain-elongation of an <a href="/wiki/Acetyl-CoA" title="Acetyl-CoA">acetyl-CoA</a> primer with <a href="/wiki/Malonyl-CoA" title="Malonyl-CoA">malonyl-CoA</a> or <a href="/wiki/Methylmalonyl-CoA" title="Methylmalonyl-CoA">methylmalonyl-CoA</a> groups in a process called <a href="/wiki/Fatty_acid_synthesis" title="Fatty acid synthesis">fatty acid synthesis</a>.<sup id="cite_ref-Vance_2002_21-0" class="reference"><a href="#cite_note-Vance_2002-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Brown_2007_22-0" class="reference"><a href="#cite_note-Brown_2007-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> They are made of a <a href="/wiki/Hydrocarbon_chain" class="mw-redirect" title="Hydrocarbon chain">hydrocarbon chain</a> that terminates with a <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a> group; this arrangement confers the molecule with a <a href="/wiki/Chemical_polarity" title="Chemical polarity">polar</a>, <a href="/wiki/Hydrophilic" class="mw-redirect" title="Hydrophilic">hydrophilic</a> end, and a nonpolar, <a href="/wiki/Hydrophobic" class="mw-redirect" title="Hydrophobic">hydrophobic</a> end that is <a href="/wiki/Insoluble" class="mw-redirect" title="Insoluble">insoluble</a> in water. The fatty acid structure is one of the most fundamental categories of biological lipids and is commonly used as a building-block of more structurally complex lipids. The carbon chain, typically between four and 24 carbons long,<sup id="cite_ref-Hunt_1995_23-0" class="reference"><a href="#cite_note-Hunt_1995-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> may be saturated or <a href="/wiki/Unsaturated_compound" class="mw-redirect" title="Unsaturated compound">unsaturated</a>, and may be attached to <a href="/wiki/Functional_group" title="Functional group">functional groups</a> containing <a href="/wiki/Oxygen" title="Oxygen">oxygen</a>, <a href="/wiki/Halogen" title="Halogen">halogens</a>, <a href="/wiki/Nitrogen" title="Nitrogen">nitrogen</a>, and <a href="/wiki/Sulfur" title="Sulfur">sulfur</a>. If a fatty acid contains a double bond, there is the possibility of either a <i>cis</i> or <i>trans</i> <a href="/wiki/Cis%E2%80%93trans_isomerism" title="Cis–trans isomerism">geometric isomerism</a>, which significantly affects the molecule's <a href="/wiki/Molecular_configuration" title="Molecular configuration">configuration</a>. <i>Cis</i>-double bonds cause the fatty acid chain to bend, an effect that is compounded with more double bonds in the chain. Three double bonds in 18-carbon <i><a href="/wiki/Linolenic_acid" title="Linolenic acid">linolenic acid</a></i>, the most abundant fatty-acyl chains of plant <i>thylakoid membranes</i>, render these membranes highly <i>fluid</i> despite environmental low-temperatures,<sup id="cite_ref-YashRoy_1987_24-0" class="reference"><a href="#cite_note-YashRoy_1987-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> and also makes linolenic acid give dominating sharp peaks in high resolution 13-C NMR spectra of chloroplasts. This in turn plays an important role in the structure and function of cell membranes.<sup id="cite_ref-Devlin_1997_25-0" class="reference"><a href="#cite_note-Devlin_1997-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 193–5">: 193–5 </span></sup> Most naturally occurring fatty acids are of the <i>cis</i> configuration, although the <i>trans</i> form does exist in some natural and partially hydrogenated fats and oils.<sup id="cite_ref-Hunter_2006_26-0" class="reference"><a href="#cite_note-Hunter_2006-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> </p><p>Examples of biologically important fatty acids include the <a href="/wiki/Eicosanoid" title="Eicosanoid">eicosanoids</a>, derived primarily from <a href="/wiki/Arachidonic_acid" title="Arachidonic acid">arachidonic acid</a> and <a href="/wiki/Eicosapentaenoic_acid" title="Eicosapentaenoic acid">eicosapentaenoic acid</a>, that include <a href="/wiki/Prostaglandin" title="Prostaglandin">prostaglandins</a>, <a href="/wiki/Leukotriene" title="Leukotriene">leukotrienes</a>, and <a href="/wiki/Thromboxane" title="Thromboxane">thromboxanes</a>. <a href="/wiki/Docosahexaenoic_acid" title="Docosahexaenoic acid">Docosahexaenoic acid</a> is also important in biological systems, particularly with respect to sight.<sup id="cite_ref-The_Lipid_Chronicles_27-0" class="reference"><a href="#cite_note-The_Lipid_Chronicles-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup><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> Other major lipid classes in the fatty acid category are the fatty esters and fatty amides. Fatty esters include important biochemical intermediates such as <a href="/wiki/Wax_ester" title="Wax ester">wax esters</a>, fatty acid thioester <a href="/wiki/Coenzyme_A" title="Coenzyme A">coenzyme A</a> derivatives, fatty acid thioester <a href="/wiki/Acyl_carrier_protein" title="Acyl carrier protein">ACP</a> derivatives and fatty acid carnitines. The fatty amides include <a href="/wiki/N-acylethanolamine" class="mw-redirect" title="N-acylethanolamine">N-acyl ethanolamines</a>, such as the <a href="/wiki/Cannabinoid" title="Cannabinoid">cannabinoid</a> neurotransmitter <a href="/wiki/Anandamide" title="Anandamide">anandamide</a>.<sup id="cite_ref-Fezza_2008_29-0" class="reference"><a href="#cite_note-Fezza_2008-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Glycerolipids">Glycerolipids</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lipid&action=edit&section=4" title="Edit section: Glycerolipids"><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:Fat_triglyceride_shorthand_formula.PNG" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/be/Fat_triglyceride_shorthand_formula.PNG/290px-Fat_triglyceride_shorthand_formula.PNG" decoding="async" width="290" height="128" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/be/Fat_triglyceride_shorthand_formula.PNG/435px-Fat_triglyceride_shorthand_formula.PNG 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/be/Fat_triglyceride_shorthand_formula.PNG/580px-Fat_triglyceride_shorthand_formula.PNG 2x" data-file-width="1152" data-file-height="510" /></a><figcaption>Example of an unsaturated fat triglyceride (C<sub>55</sub>H<sub>98</sub>O<sub>6</sub>). Left part: <a href="/wiki/Glycerol" title="Glycerol">glycerol</a>; right part, from top to bottom: <a href="/wiki/Palmitic_acid" title="Palmitic acid">palmitic acid</a>, <a href="/wiki/Oleic_acid" title="Oleic acid">oleic acid</a>, <a href="/wiki/Alpha-linolenic_acid" class="mw-redirect" title="Alpha-linolenic acid">alpha-linolenic acid</a>.</figcaption></figure> <p>Glycerolipids are composed of mono-, di-, and tri-substituted <a href="/wiki/Glycerol" title="Glycerol">glycerols</a>,<sup id="cite_ref-Coleman_2004_30-0" class="reference"><a href="#cite_note-Coleman_2004-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> the best-known being the fatty acid <a href="/wiki/Ester" title="Ester">triesters</a> of glycerol, called <a href="/wiki/Triglyceride" title="Triglyceride">triglycerides</a>. The word "triacylglycerol" is sometimes used synonymously with "triglyceride". In these compounds, the three hydroxyl groups of glycerol are each esterified, typically by different fatty acids. Because they function as an energy store, these lipids comprise the bulk of storage <a href="/wiki/Fat" title="Fat">fat</a> in animal tissues. The hydrolysis of the ester bonds of triglycerides and the release of glycerol and fatty acids from <a href="/wiki/Adipose_tissue" title="Adipose tissue">adipose tissue</a> are the initial steps in metabolizing fat.<sup id="cite_ref-van_Holde_1996_31-0" class="reference"><a href="#cite_note-van_Holde_1996-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 630–1">: 630–1 </span></sup> </p><p>Additional subclasses of glycerolipids are represented by glycosylglycerols, which are characterized by the presence of one or more <a href="/wiki/Monosaccharide" title="Monosaccharide">sugar residues</a> attached to glycerol via a <a href="/wiki/Glycosidic_linkage" class="mw-redirect" title="Glycosidic linkage">glycosidic linkage</a>. Examples of structures in this category are the digalactosyldiacylglycerols found in plant membranes<sup id="cite_ref-Hölzl_2007_32-0" class="reference"><a href="#cite_note-Hölzl_2007-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> and seminolipid from mammalian <a href="/wiki/Sperm_cells" class="mw-redirect" title="Sperm cells">sperm cells</a>.<sup id="cite_ref-Honke_2004_33-0" class="reference"><a href="#cite_note-Honke_2004-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Glycerophospholipids">Glycerophospholipids</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lipid&action=edit&section=5" title="Edit section: Glycerophospholipids"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Glycerophospholipid" title="Glycerophospholipid">Glycerophospholipid</a></div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Phosphatidyl-ethanolamine.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c7/Phosphatidyl-ethanolamine.svg/300px-Phosphatidyl-ethanolamine.svg.png" decoding="async" width="300" height="130" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c7/Phosphatidyl-ethanolamine.svg/450px-Phosphatidyl-ethanolamine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c7/Phosphatidyl-ethanolamine.svg/600px-Phosphatidyl-ethanolamine.svg.png 2x" data-file-width="660" data-file-height="286" /></a><figcaption><a href="/wiki/Phosphatidylethanolamine" title="Phosphatidylethanolamine">Phosphatidylethanolamine</a></figcaption></figure> <p>Glycerophospholipids, usually referred to as <a href="/wiki/Phospholipid" title="Phospholipid">phospholipids</a> (though <a href="/wiki/Sphingomyelin" title="Sphingomyelin">sphingomyelins</a> are also classified as phospholipids), are ubiquitous in nature and are key components of the <a href="/wiki/Lipid_bilayer" title="Lipid bilayer">lipid bilayer</a> of cells,<sup id="cite_ref-The_Structure_of_a_Membrane_34-0" class="reference"><a href="#cite_note-The_Structure_of_a_Membrane-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> as well as being involved in <a href="/wiki/Metabolism" title="Metabolism">metabolism</a> and <a href="/wiki/Cell_signaling" title="Cell signaling">cell signaling</a>.<sup id="cite_ref-Berridge_1989_35-0" class="reference"><a href="#cite_note-Berridge_1989-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> Neural tissue (including the brain) contains relatively high amounts of glycerophospholipids, and alterations in their composition has been implicated in various neurological disorders.<sup id="cite_ref-pmid10878232_36-0" class="reference"><a href="#cite_note-pmid10878232-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> Glycerophospholipids may be subdivided into distinct classes, based on the nature of the polar headgroup at the <i>sn</i>-3 position of the glycerol backbone in <a href="/wiki/Eukaryote" title="Eukaryote">eukaryotes</a> and eubacteria, or the <i>sn</i>-1 position in the case of <a href="/wiki/Archaebacteria" class="mw-redirect" title="Archaebacteria">archaebacteria</a>.<sup id="cite_ref-Ivanova_2007_37-0" class="reference"><a href="#cite_note-Ivanova_2007-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> </p><p>Examples of glycerophospholipids found in <a href="/wiki/Biological_membrane" title="Biological membrane">biological membranes</a> are <a href="/wiki/Phosphatidylcholine" title="Phosphatidylcholine">phosphatidylcholine</a> (also known as PC, GPCho or <a href="/wiki/Lecithin" title="Lecithin">lecithin</a>), <a href="/wiki/Phosphatidylethanolamine" title="Phosphatidylethanolamine">phosphatidylethanolamine</a> (PE or GPEtn) and <a href="/wiki/Phosphatidylserine" title="Phosphatidylserine">phosphatidylserine</a> (PS or GPSer). In addition to serving as a primary component of cellular membranes and binding sites for intra- and intercellular proteins, some glycerophospholipids in eukaryotic cells, such as <a href="/wiki/Phosphatidylinositol" title="Phosphatidylinositol">phosphatidylinositols</a> and <a href="/wiki/Phosphatidic_acid" title="Phosphatidic acid">phosphatidic acids</a> are either precursors of or, themselves, membrane-derived <a href="/wiki/Second_messenger_system" title="Second messenger system">second messengers</a>.<sup id="cite_ref-van_Holde_1996_31-1" class="reference"><a href="#cite_note-van_Holde_1996-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 844">: 844 </span></sup> Typically, one or both of these hydroxyl groups are acylated with long-chain fatty acids, but there are also alkyl-linked and 1Z-alkenyl-linked (<a href="/wiki/Plasmalogen" title="Plasmalogen">plasmalogen</a>) glycerophospholipids, as well as dialkylether variants in archaebacteria.<sup id="cite_ref-Paltauf_1994_38-0" class="reference"><a href="#cite_note-Paltauf_1994-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Sphingolipids">Sphingolipids</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lipid&action=edit&section=6" title="Edit section: Sphingolipids"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Sphingolipid" title="Sphingolipid">Sphingolipid</a></div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Sphingomyelin-horizontal-2D-skeletal.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/92/Sphingomyelin-horizontal-2D-skeletal.png/300px-Sphingomyelin-horizontal-2D-skeletal.png" decoding="async" width="300" height="86" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/92/Sphingomyelin-horizontal-2D-skeletal.png/450px-Sphingomyelin-horizontal-2D-skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/92/Sphingomyelin-horizontal-2D-skeletal.png/600px-Sphingomyelin-horizontal-2D-skeletal.png 2x" data-file-width="1100" data-file-height="314" /></a><figcaption><a href="/wiki/Sphingomyelin" title="Sphingomyelin">Sphingomyelin</a></figcaption></figure> <p>Sphingolipids are a complicated family of compounds<sup id="cite_ref-Merrill_39-0" class="reference"><a href="#cite_note-Merrill-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> that share a common structural feature, a <a href="/wiki/Sphingoid_base" class="mw-redirect" title="Sphingoid base">sphingoid base</a> backbone that is synthesized <a href="/wiki/De_novo_synthesis" title="De novo synthesis"><i>de novo</i></a> from the amino acid <a href="/wiki/Serine" title="Serine">serine</a> and a long-chain fatty acyl CoA, then converted into <a href="/wiki/Ceramide" title="Ceramide">ceramides</a>, phosphosphingolipids, glycosphingolipids and other compounds. The major sphingoid base of mammals is commonly referred to as <a href="/wiki/Sphingosine" title="Sphingosine">sphingosine</a>. Ceramides (N-acyl-sphingoid bases) are a major subclass of sphingoid base derivatives with an <a href="/wiki/Amide" title="Amide">amide</a>-linked fatty acid. The fatty acids are typically saturated or mono-unsaturated with chain lengths from 16 to 26 carbon atoms.<sup id="cite_ref-Devlin_1997_25-1" class="reference"><a href="#cite_note-Devlin_1997-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 421–2">: 421–2 </span></sup> </p><p>The major phosphosphingolipids of mammals are <a href="/wiki/Sphingomyelin" title="Sphingomyelin">sphingomyelins</a> (ceramide phosphocholines),<sup id="cite_ref-Hori_1993_40-0" class="reference"><a href="#cite_note-Hori_1993-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> whereas insects contain mainly ceramide phosphoethanolamines<sup id="cite_ref-Wiegandt_1992_41-0" class="reference"><a href="#cite_note-Wiegandt_1992-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> and fungi have phytoceramide phosphoinositols and <a href="/wiki/Mannose" title="Mannose">mannose</a>-containing headgroups.<sup id="cite_ref-Guan_2008_42-0" class="reference"><a href="#cite_note-Guan_2008-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> The glycosphingolipids are a diverse family of molecules composed of one or more sugar residues linked via a <a href="/wiki/Glycosidic_bond" title="Glycosidic bond">glycosidic bond</a> to the sphingoid base. Examples of these are the simple and complex glycosphingolipids such as <a href="/wiki/Cerebroside" title="Cerebroside">cerebrosides</a> and <a href="/wiki/Ganglioside" title="Ganglioside">gangliosides</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Sterols">Sterols</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lipid&action=edit&section=7" title="Edit section: Sterols"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Cholesterol.svg" class="mw-file-description"><img alt="Chemical diagram" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9a/Cholesterol.svg/280px-Cholesterol.svg.png" decoding="async" width="280" height="178" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9a/Cholesterol.svg/420px-Cholesterol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9a/Cholesterol.svg/560px-Cholesterol.svg.png 2x" data-file-width="613" data-file-height="390" /></a><figcaption>Chemical structure of <a href="/wiki/Cholesterol" title="Cholesterol">cholesterol</a></figcaption></figure> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Sterol" title="Sterol">Sterol</a></div> <p>Sterols, such as <a href="/wiki/Cholesterol" title="Cholesterol">cholesterol</a> and its derivatives, are an important component of membrane lipids,<sup id="cite_ref-Bach_2003_43-0" class="reference"><a href="#cite_note-Bach_2003-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> along with the glycerophospholipids and sphingomyelins. Other examples of sterols are the <a href="/wiki/Bile_acid" title="Bile acid">bile acids</a> and their conjugates,<sup id="cite_ref-Russell_2003_44-0" class="reference"><a href="#cite_note-Russell_2003-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> which in mammals are oxidized derivatives of cholesterol and are synthesized in the liver. The plant equivalents are the <a href="/wiki/Phytosterols" class="mw-redirect" title="Phytosterols">phytosterols</a>, such as <a href="/wiki/%CE%92-sitosterol" class="mw-redirect" title="Β-sitosterol">β-sitosterol</a>, <a href="/wiki/Stigmasterol" title="Stigmasterol">stigmasterol</a>, and <a href="/wiki/Brassicasterol" title="Brassicasterol">brassicasterol</a>; the latter compound is also used as a <a href="/wiki/Biomarker" title="Biomarker">biomarker</a> for <a href="/wiki/Algae" title="Algae">algal</a> growth.<sup id="cite_ref-Villinski_2008_45-0" class="reference"><a href="#cite_note-Villinski_2008-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> The predominant sterol in <a href="/wiki/Fungal" class="mw-redirect" title="Fungal">fungal</a> cell membranes is <a href="/wiki/Ergosterol" title="Ergosterol">ergosterol</a>.<sup id="cite_ref-Deacon_2005_46-0" class="reference"><a href="#cite_note-Deacon_2005-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> </p><p>Sterols are <a href="/wiki/Steroid" title="Steroid">steroids</a> in which one of the hydrogen atoms is substituted with a <a href="/wiki/Hydroxyl_group" class="mw-redirect" title="Hydroxyl group">hydroxyl group</a>, at position 3 in the carbon chain. They have in common with steroids the same fused four-ring core structure. Steroids have different biological roles as <a href="/wiki/Hormone" title="Hormone">hormones</a> and <a href="/wiki/Signaling_molecules" class="mw-redirect" title="Signaling molecules">signaling molecules</a>. The eighteen-carbon (C18) steroids include the <a href="/wiki/Estrogen" title="Estrogen">estrogen</a> family whereas the C19 steroids comprise the <a href="/wiki/Androgen" title="Androgen">androgens</a> such as <a href="/wiki/Testosterone" title="Testosterone">testosterone</a> and <a href="/wiki/Androsterone" title="Androsterone">androsterone</a>. The C21 subclass includes the <a href="/wiki/Progestogens" class="mw-redirect" title="Progestogens">progestogens</a> as well as the <a href="/wiki/Glucocorticoid" title="Glucocorticoid">glucocorticoids</a> and <a href="/wiki/Mineralocorticoids" class="mw-redirect" title="Mineralocorticoids">mineralocorticoids</a>.<sup id="cite_ref-Stryer_2007_2-1" class="reference"><a href="#cite_note-Stryer_2007-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 749">: 749 </span></sup> The <a href="/wiki/Secosteroid" title="Secosteroid">secosteroids</a>, comprising various forms of <a href="/wiki/Vitamin_D" title="Vitamin D">vitamin D</a>, are characterized by cleavage of the B ring of the core structure.<sup id="cite_ref-Bouillon_2006_47-0" class="reference"><a href="#cite_note-Bouillon_2006-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Prenols">Prenols</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lipid&action=edit&section=8" title="Edit section: Prenols"><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:Geraniol_structure.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/39/Geraniol_structure.png/220px-Geraniol_structure.png" decoding="async" width="220" height="51" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/39/Geraniol_structure.png/330px-Geraniol_structure.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/39/Geraniol_structure.png/440px-Geraniol_structure.png 2x" data-file-width="3716" data-file-height="863" /></a><figcaption>Prenol lipid (2<i>E</i>-geraniol)</figcaption></figure> <p><a href="/wiki/Prenol" title="Prenol">Prenol</a> lipids are synthesized from the five-carbon-unit precursors <a href="/wiki/Isopentenyl_diphosphate" class="mw-redirect" title="Isopentenyl diphosphate">isopentenyl diphosphate</a> and <a href="/wiki/Dimethylallyl_diphosphate" class="mw-redirect" title="Dimethylallyl diphosphate">dimethylallyl diphosphate</a>, which are produced mainly via the <a href="/wiki/Mevalonic_acid" title="Mevalonic acid">mevalonic acid</a> (MVA) pathway.<sup id="cite_ref-Kuzuyama_2003_48-0" class="reference"><a href="#cite_note-Kuzuyama_2003-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> The simple isoprenoids (linear alcohols, diphosphates, etc.) are formed by the successive addition of C5 units, and are classified according to number of these <a href="/wiki/Terpene" title="Terpene">terpene</a> units. Structures containing greater than 40 carbons are known as polyterpenes. <a href="/wiki/Carotenoid" title="Carotenoid">Carotenoids</a> are important simple isoprenoids that function as <a href="/wiki/Antioxidant" title="Antioxidant">antioxidants</a> and as precursors of <a href="/wiki/Vitamin_A" title="Vitamin A">vitamin A</a>.<sup id="cite_ref-Rao_2007_49-0" class="reference"><a href="#cite_note-Rao_2007-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> Another biologically important class of molecules is exemplified by the <a href="/wiki/Quinone" title="Quinone">quinones</a> and <a href="/wiki/Hydroquinone" title="Hydroquinone">hydroquinones</a>, which contain an isoprenoid tail attached to a quinonoid core of non-isoprenoid origin.<sup id="cite_ref-Brunmark_1989_50-0" class="reference"><a href="#cite_note-Brunmark_1989-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Vitamin_E" title="Vitamin E">Vitamin E</a> and <a href="/wiki/Vitamin_K" title="Vitamin K">vitamin K</a>, as well as the <a href="/wiki/Ubiquinone" class="mw-redirect" title="Ubiquinone">ubiquinones</a>, are examples of this class. Prokaryotes synthesize polyprenols (called <a href="/wiki/Bactoprenol" title="Bactoprenol">bactoprenols</a>) in which the terminal isoprenoid unit attached to oxygen remains unsaturated, whereas in animal polyprenols (<a href="/wiki/Dolichol" title="Dolichol">dolichols</a>) the terminal isoprenoid is reduced.<sup id="cite_ref-Swiezewska_2005_51-0" class="reference"><a href="#cite_note-Swiezewska_2005-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Saccharolipids">Saccharolipids</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lipid&action=edit&section=9" title="Edit section: Saccharolipids"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Kdo2-lipidA.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3c/Kdo2-lipidA.png/300px-Kdo2-lipidA.png" decoding="async" width="300" height="259" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3c/Kdo2-lipidA.png/450px-Kdo2-lipidA.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3c/Kdo2-lipidA.png/600px-Kdo2-lipidA.png 2x" data-file-width="1667" data-file-height="1440" /></a><figcaption>Structure of the saccharolipid Kdo<sub>2</sub>-lipid A.<sup id="cite_ref-Raetz_2006_52-0" class="reference"><a href="#cite_note-Raetz_2006-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Glucosamine" title="Glucosamine">Glucosamine</a> residues in blue, <a href="/wiki/3-Deoxy-D-manno-oct-2-ulosonic_acid" title="3-Deoxy-D-manno-oct-2-ulosonic acid">Kdo</a> residues in red, <a href="/wiki/Acyl" class="mw-redirect" title="Acyl">acyl</a> chains in black and <a href="/wiki/Phosphate" title="Phosphate">phosphate</a> groups in green.</figcaption></figure> <p><a href="/wiki/Saccharolipid" title="Saccharolipid">Saccharolipids</a> describe compounds in which fatty acids are linked to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a <a href="/wiki/Monosaccharide" title="Monosaccharide">monosaccharide</a> substitutes for the glycerol backbone present in glycerolipids and glycerophospholipids. The most familiar saccharolipids are the acylated <a href="/wiki/Glucosamine" title="Glucosamine">glucosamine</a> precursors of the <a href="/wiki/Lipid_A" title="Lipid A">Lipid A</a> component of the <a href="/wiki/Lipopolysaccharide" title="Lipopolysaccharide">lipopolysaccharides</a> in <a href="/wiki/Gram-negative_bacteria" title="Gram-negative bacteria">Gram-negative bacteria</a>. Typical lipid A molecules are <a href="/wiki/Disaccharides" class="mw-redirect" title="Disaccharides">disaccharides</a> of glucosamine, which are derivatized with as many as seven fatty-acyl chains. The minimal lipopolysaccharide required for growth in <a href="/wiki/Escherichia_coli" title="Escherichia coli"><i>E. coli</i></a> is Kdo<sub>2</sub>-Lipid A, a hexa-acylated disaccharide of glucosamine that is glycosylated with two 3-deoxy-D-manno-octulosonic acid (Kdo) residues.<sup id="cite_ref-Raetz_2006_52-1" class="reference"><a href="#cite_note-Raetz_2006-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Polyketides">Polyketides</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lipid&action=edit&section=10" title="Edit section: Polyketides"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Polyketides are synthesized by polymerization of <a href="/wiki/Acetyl" class="mw-redirect" title="Acetyl">acetyl</a> and <a href="/wiki/Propionyl-CoA" title="Propionyl-CoA">propionyl</a> subunits by classic enzymes as well as iterative and multimodular enzymes that share mechanistic features with the <a href="/wiki/Fatty_acid_synthase" title="Fatty acid synthase">fatty acid synthases</a>. They comprise many <a href="/wiki/Secondary_metabolite" title="Secondary metabolite">secondary metabolites</a> and <a href="/wiki/Natural_products" class="mw-redirect" title="Natural products">natural products</a> from animal, plant, bacterial, fungal and marine sources, and have great structural diversity.<sup id="cite_ref-Walsh_2004_53-0" class="reference"><a href="#cite_note-Walsh_2004-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Caffrey_2008_54-0" class="reference"><a href="#cite_note-Caffrey_2008-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup> Many <a href="/wiki/Polyketide" title="Polyketide">polyketides</a> are cyclic molecules whose backbones are often further modified by <a href="/wiki/Glycosylation" title="Glycosylation">glycosylation</a>, <a href="/wiki/Methylation" title="Methylation">methylation</a>, <a href="/wiki/Hydroxylation" title="Hydroxylation">hydroxylation</a>, <a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">oxidation</a>, or other processes. Many commonly used <a href="/wiki/Antimicrobial" title="Antimicrobial">antimicrobial</a>, <a href="/wiki/Antiparasitic" title="Antiparasitic">antiparasitic</a>, and <a href="/wiki/Anticancer" class="mw-redirect" title="Anticancer">anticancer</a> agents are polyketides or polyketide derivatives, such as <a href="/wiki/Erythromycin" title="Erythromycin">erythromycins</a>, <a href="/wiki/Tetracycline_antibiotics" title="Tetracycline antibiotics">tetracyclines</a>, <a href="/wiki/Avermectin" title="Avermectin">avermectins</a>, and antitumor <a href="/wiki/Epothilone" title="Epothilone">epothilones</a>.<sup id="cite_ref-Minto_2008_55-0" class="reference"><a href="#cite_note-Minto_2008-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Biological_functions">Biological functions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lipid&action=edit&section=11" title="Edit section: Biological functions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Component_of_biological_membranes">Component of biological membranes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lipid&action=edit&section=12" title="Edit section: Component of biological membranes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Eukaryote" title="Eukaryote">Eukaryotic</a> cells feature the compartmentalized membrane-bound <a href="/wiki/Organelle" title="Organelle">organelles</a> that carry out different biological functions. The <a href="/wiki/Glycerophospholipids" class="mw-redirect" title="Glycerophospholipids">glycerophospholipids</a> are the main structural component of <a href="/wiki/Biological_membranes" class="mw-redirect" title="Biological membranes">biological membranes</a>, as the cellular <a href="/wiki/Plasma_membrane" class="mw-redirect" title="Plasma membrane">plasma membrane</a> and the intracellular membranes of organelles; in animal cells, the plasma membrane physically separates the <a href="/wiki/Intracellular" class="mw-redirect" title="Intracellular">intracellular</a> components from the <a href="/wiki/Extracellular" class="mw-redirect" title="Extracellular">extracellular</a> environment.<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. (January 2015)">citation needed</span></a></i>]</sup> The glycerophospholipids are <a href="/wiki/Amphipathic" class="mw-redirect" title="Amphipathic">amphipathic</a> molecules (containing both hydrophobic and hydrophilic regions) that contain a glycerol core linked to two fatty acid-derived "tails" by ester linkages and to one "head" group by a <a href="/wiki/Phosphate" title="Phosphate">phosphate</a> ester linkage.<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. (January 2015)">citation needed</span></a></i>]</sup> While glycerophospholipids are the major component of biological membranes, other non-glyceride lipid components such as <a href="/wiki/Sphingomyelin" title="Sphingomyelin">sphingomyelin</a> and <a href="/wiki/Sterol" title="Sterol">sterols</a> (mainly cholesterol in animal cell membranes) are also found in biological membranes.<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><sup id="cite_ref-Stryer_2007_2-2" class="reference"><a href="#cite_note-Stryer_2007-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 329–331">: 329–331 </span></sup> In plants and algae, the galactosyldiacylglycerols,<sup id="cite_ref-Heinz_57-0" class="reference"><a href="#cite_note-Heinz-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup> and sulfoquinovosyldiacylglycerol,<sup id="cite_ref-Hölzl_2007_32-1" class="reference"><a href="#cite_note-Hölzl_2007-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> which lack a phosphate group, are important components of membranes of chloroplasts and related organelles and are among the most abundant lipids in photosynthetic tissues, including those of higher plants, algae and certain bacteria.<sup id="cite_ref-Lyu_et_al._2021_58-0" class="reference"><a href="#cite_note-Lyu_et_al._2021-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup> </p><p>Plant thylakoid membranes have the largest lipid component of a non-bilayer forming monogalactosyl diglyceride (MGDG), and little phospholipids; despite this unique lipid composition, chloroplast thylakoid membranes have been shown to contain a dynamic lipid-bilayer matrix as revealed by magnetic resonance and electron microscope studies.<sup id="cite_ref-Yashroy_1990_59-0" class="reference"><a href="#cite_note-Yashroy_1990-59"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup> </p> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Phospholipids_aqueous_solution_structures.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c6/Phospholipids_aqueous_solution_structures.svg/250px-Phospholipids_aqueous_solution_structures.svg.png" decoding="async" width="250" height="307" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c6/Phospholipids_aqueous_solution_structures.svg/375px-Phospholipids_aqueous_solution_structures.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c6/Phospholipids_aqueous_solution_structures.svg/500px-Phospholipids_aqueous_solution_structures.svg.png 2x" data-file-width="331" data-file-height="407" /></a><figcaption>Self-organization of <a href="/wiki/Phospholipid" title="Phospholipid">phospholipids</a>: a spherical <a href="/wiki/Liposome" title="Liposome">liposome</a>, a <a href="/wiki/Micelle" title="Micelle">micelle</a>, and a <a href="/wiki/Lipid_bilayer" title="Lipid bilayer">lipid bilayer</a>.</figcaption></figure> <p>A biological membrane is a form of <a href="/wiki/Lamellar_phase" title="Lamellar phase">lamellar phase</a> <a href="/wiki/Lipid_bilayer" title="Lipid bilayer">lipid bilayer</a>. The formation of lipid bilayers is an energetically preferred process when the <a href="/wiki/Glycerophospholipids" class="mw-redirect" title="Glycerophospholipids">glycerophospholipids</a> described above are in an aqueous environment.<sup id="cite_ref-Stryer_2007_2-3" class="reference"><a href="#cite_note-Stryer_2007-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 333–4">: 333–4 </span></sup> This is known as the <a href="/wiki/Hydrophobic_effect" title="Hydrophobic effect">hydrophobic effect</a>. In an aqueous system, the polar heads of lipids align towards the polar, aqueous environment, while the hydrophobic tails minimize their contact with water and tend to cluster together, forming a <a href="/wiki/Vesicle_(biology)" class="mw-redirect" title="Vesicle (biology)">vesicle</a>; depending on the <a href="/wiki/Critical_micelle_concentration" title="Critical micelle concentration">concentration</a> of the lipid, this biophysical interaction may result in the formation of <a href="/wiki/Micelle" title="Micelle">micelles</a>, <a href="/wiki/Liposomes" class="mw-redirect" title="Liposomes">liposomes</a>, or <a href="/wiki/Lipid_bilayer" title="Lipid bilayer">lipid bilayers</a>. Other aggregations are also observed and form part of the polymorphism of <a href="/wiki/Amphiphile" title="Amphiphile">amphiphile</a> (lipid) behavior. <a href="/wiki/Phase_behaviour" class="mw-redirect" title="Phase behaviour">Phase behavior</a> is an area of study within <a href="/wiki/Biophysics" title="Biophysics">biophysics</a>.<sup id="cite_ref-van_Meer_2008_60-0" class="reference"><a href="#cite_note-van_Meer_2008-60"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Feigenson_2006_61-0" class="reference"><a href="#cite_note-Feigenson_2006-61"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup> Micelles and bilayers form in the polar medium by a process known as the hydrophobic effect.<sup id="cite_ref-Wiggins_1990_62-0" class="reference"><a href="#cite_note-Wiggins_1990-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup> When dissolving a lipophilic or amphiphilic substance in a polar environment, the polar molecules (i.e., water in an aqueous solution) become more ordered around the dissolved lipophilic substance, since the polar molecules cannot form <a href="/wiki/Hydrogen_bond" title="Hydrogen bond">hydrogen bonds</a> to the lipophilic areas of the amphiphile. So in an aqueous environment, the water molecules form an ordered "<a href="/wiki/Clathrate" class="mw-redirect" title="Clathrate">clathrate</a>" cage around the dissolved lipophilic molecule.<sup id="cite_ref-Raschke_2005_63-0" class="reference"><a href="#cite_note-Raschke_2005-63"><span class="cite-bracket">[</span>63<span class="cite-bracket">]</span></a></sup> </p><p>The formation of lipids into <a href="/wiki/Protocell" title="Protocell">protocell</a> membranes represents a key step in models of <a href="/wiki/Abiogenesis" title="Abiogenesis">abiogenesis</a>, the origin of life.<sup id="cite_ref-Segré_2001_64-0" class="reference"><a href="#cite_note-Segré_2001-64"><span class="cite-bracket">[</span>64<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Energy_storage">Energy storage</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lipid&action=edit&section=13" title="Edit section: Energy storage"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Triglycerides, stored in adipose tissue, are a major form of energy storage both in animals and plants. They are a major source of energy in aerobic respiration. The complete oxidation of fatty acids releases about 38 kJ/g (9 <a href="/wiki/Calorie#Kilogram_and_gram_calories" title="Calorie">kcal/g</a>), compared with only 17 kJ/g (4 kcal/g) for the oxidative breakdown of <a href="/wiki/Carbohydrate" title="Carbohydrate">carbohydrates</a> and <a href="/wiki/Protein" title="Protein">proteins</a>. The <a href="/wiki/Adipocyte" title="Adipocyte">adipocyte</a>, or fat cell, is designed for continuous synthesis and breakdown of triglycerides in animals, with breakdown controlled mainly by the activation of hormone-sensitive enzyme <a href="/wiki/Lipase" title="Lipase">lipase</a>.<sup id="cite_ref-Brasaemle_2007_65-0" class="reference"><a href="#cite_note-Brasaemle_2007-65"><span class="cite-bracket">[</span>65<span class="cite-bracket">]</span></a></sup> Migratory birds that must fly long distances without eating use triglycerides to fuel their flights.<sup id="cite_ref-Stryer_2007_2-4" class="reference"><a href="#cite_note-Stryer_2007-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 619">: 619 </span></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Signaling">Signaling</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lipid&action=edit&section=14" title="Edit section: Signaling"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Evidence has emerged showing that <a href="/wiki/Lipid_signaling" title="Lipid signaling">lipid signaling</a> is a vital part of the <a href="/wiki/Cell_signaling" title="Cell signaling">cell signaling</a>.<sup id="cite_ref-pmid21743455_66-0" class="reference"><a href="#cite_note-pmid21743455-66"><span class="cite-bracket">[</span>66<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid=18256869_67-0" class="reference"><a href="#cite_note-pmid=18256869-67"><span class="cite-bracket">[</span>67<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Wang_2004_68-0" class="reference"><a href="#cite_note-Wang_2004-68"><span class="cite-bracket">[</span>68<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Dinasarapu_2011_69-0" class="reference"><a href="#cite_note-Dinasarapu_2011-69"><span class="cite-bracket">[</span>69<span class="cite-bracket">]</span></a></sup> Lipid signaling may occur via activation of <a href="/wiki/G_protein-coupled_receptor" title="G protein-coupled receptor">G protein-coupled</a> or <a href="/wiki/Nuclear_receptor" title="Nuclear receptor">nuclear receptors</a>, and members of several different lipid categories have been identified as signaling molecules and <a href="/wiki/Second_messenger_system" title="Second messenger system">cellular messengers</a>.<sup id="cite_ref-Eyster_2007_70-0" class="reference"><a href="#cite_note-Eyster_2007-70"><span class="cite-bracket">[</span>70<span class="cite-bracket">]</span></a></sup> These include <a href="/wiki/Sphingosine-1-phosphate" title="Sphingosine-1-phosphate">sphingosine-1-phosphate</a>, a sphingolipid derived from ceramide that is a potent messenger molecule involved in regulating calcium mobilization,<sup id="cite_ref-Hinkovska-Galcheva_2008_71-0" class="reference"><a href="#cite_note-Hinkovska-Galcheva_2008-71"><span class="cite-bracket">[</span>71<span class="cite-bracket">]</span></a></sup> cell growth, and apoptosis;<sup id="cite_ref-Saddoughi_2008_72-0" class="reference"><a href="#cite_note-Saddoughi_2008-72"><span class="cite-bracket">[</span>72<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Diacylglycerol" class="mw-redirect" title="Diacylglycerol">diacylglycerol</a> and the <a href="/wiki/Phosphatidylinositol" title="Phosphatidylinositol">phosphatidylinositol</a> phosphates (PIPs), involved in calcium-mediated activation of <a href="/wiki/Protein_kinase_C" title="Protein kinase C">protein kinase C</a>;<sup id="cite_ref-Klein_2008_73-0" class="reference"><a href="#cite_note-Klein_2008-73"><span class="cite-bracket">[</span>73<span class="cite-bracket">]</span></a></sup> the <a href="/wiki/Prostaglandins" class="mw-redirect" title="Prostaglandins">prostaglandins</a>, which are one type of fatty-acid derived eicosanoid involved in <a href="/wiki/Inflammation" title="Inflammation">inflammation</a> and <a href="/wiki/Immunity_(medical)" class="mw-redirect" title="Immunity (medical)">immunity</a>;<sup id="cite_ref-Boyce_2008_74-0" class="reference"><a href="#cite_note-Boyce_2008-74"><span class="cite-bracket">[</span>74<span class="cite-bracket">]</span></a></sup> the steroid hormones such as <a href="/wiki/Estrogen" title="Estrogen">estrogen</a>, <a href="/wiki/Testosterone" title="Testosterone">testosterone</a> and <a href="/wiki/Cortisol" title="Cortisol">cortisol</a>, which modulate a host of functions such as reproduction, metabolism and blood pressure; and the <a href="/wiki/Oxysterol" title="Oxysterol">oxysterols</a> such as 25-hydroxy-cholesterol that are <a href="/wiki/Liver_X_receptor" title="Liver X receptor">liver X receptor</a> <a href="/wiki/Agonist" title="Agonist">agonists</a>.<sup id="cite_ref-Bełtowski_2008_75-0" class="reference"><a href="#cite_note-Bełtowski_2008-75"><span class="cite-bracket">[</span>75<span class="cite-bracket">]</span></a></sup> Phosphatidylserine lipids are known to be involved in signaling for the phagocytosis of apoptotic cells or pieces of cells. They accomplish this by being exposed to the extracellular face of the cell membrane after the inactivation of <a href="/wiki/Flippase" title="Flippase">flippases</a> which place them exclusively on the cytosolic side and the activation of scramblases, which scramble the orientation of the phospholipids. After this occurs, other cells recognize the phosphatidylserines and phagocytosize the cells or cell fragments exposing them.<sup id="cite_ref-Biermann_2013_76-0" class="reference"><a href="#cite_note-Biermann_2013-76"><span class="cite-bracket">[</span>76<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Other_functions">Other functions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lipid&action=edit&section=15" title="Edit section: Other functions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The "fat-soluble" vitamins (<a href="/wiki/Retinol" title="Retinol">A</a>, <a href="/wiki/Calciferol" class="mw-redirect" title="Calciferol">D</a>, <a href="/wiki/Tocopherol" title="Tocopherol">E</a> and <a href="/wiki/Phylloquinone" class="mw-redirect" title="Phylloquinone">K</a>) – which are <a href="/wiki/Isoprene" title="Isoprene">isoprene</a>-based lipids – are essential nutrients stored in the liver and fatty tissues, with a diverse range of functions. <a href="/wiki/Carnitine#Role_in_fatty_acid_metabolism" title="Carnitine">Acyl-carnitines</a> are involved in the transport and metabolism of fatty acids in and out of mitochondria, where they undergo <a href="/wiki/Beta_oxidation" title="Beta oxidation">beta oxidation</a>.<sup id="cite_ref-77" class="reference"><a href="#cite_note-77"><span class="cite-bracket">[</span>77<span class="cite-bracket">]</span></a></sup> Polyprenols and their phosphorylated derivatives also play important transport roles, in this case the transport of <a href="/wiki/Oligosaccharide" title="Oligosaccharide">oligosaccharides</a> across membranes. Polyprenol phosphate sugars and polyprenol diphosphate sugars function in extra-cytoplasmic glycosylation reactions, in extracellular polysaccharide biosynthesis (for instance, <a href="/wiki/Peptidoglycan" title="Peptidoglycan">peptidoglycan</a> polymerization in bacteria), and in eukaryotic protein N-<a href="/wiki/Glycosylation" title="Glycosylation">glycosylation</a>.<sup id="cite_ref-Parodi_1979_78-0" class="reference"><a href="#cite_note-Parodi_1979-78"><span class="cite-bracket">[</span>78<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Helenius_2001_79-0" class="reference"><a href="#cite_note-Helenius_2001-79"><span class="cite-bracket">[</span>79<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Cardiolipin" title="Cardiolipin">Cardiolipins</a> are a subclass of glycerophospholipids containing four acyl chains and three glycerol groups that are particularly abundant in the inner mitochondrial membrane.<sup id="cite_ref-Nowicki_2005_80-0" class="reference"><a href="#cite_note-Nowicki_2005-80"><span class="cite-bracket">[</span>80<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Gohil_2009_81-0" class="reference"><a href="#cite_note-Gohil_2009-81"><span class="cite-bracket">[</span>81<span class="cite-bracket">]</span></a></sup> They are believed to activate enzymes involved with <a href="/wiki/Oxidative_phosphorylation" title="Oxidative phosphorylation">oxidative phosphorylation</a>.<sup id="cite_ref-Hoch_1992_82-0" class="reference"><a href="#cite_note-Hoch_1992-82"><span class="cite-bracket">[</span>82<span class="cite-bracket">]</span></a></sup> Lipids also form the basis of steroid hormones.<sup id="cite_ref-83" class="reference"><a href="#cite_note-83"><span class="cite-bracket">[</span>83<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Metabolism">Metabolism</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lipid&action=edit&section=16" title="Edit section: Metabolism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The major dietary lipids for humans and other animals are animal and plant triglycerides, sterols, and membrane phospholipids. The process of lipid metabolism synthesizes and degrades the lipid stores and produces the structural and functional lipids characteristic of individual tissues. </p> <div class="mw-heading mw-heading3"><h3 id="Biosynthesis">Biosynthesis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lipid&action=edit&section=17" title="Edit section: Biosynthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In animals, when there is an oversupply of dietary carbohydrate, the excess carbohydrate is converted to triglycerides. This involves the synthesis of fatty acids from <a href="/wiki/Acetyl-CoA" title="Acetyl-CoA">acetyl-CoA</a> and the <a href="/wiki/Esterification" class="mw-redirect" title="Esterification">esterification</a> of fatty acids in the production of triglycerides, a process called <a href="/wiki/Lipogenesis" title="Lipogenesis">lipogenesis</a>.<sup id="cite_ref-Stryer_2007_2-5" class="reference"><a href="#cite_note-Stryer_2007-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 634">: 634 </span></sup> Fatty acids are made by <a href="/wiki/Fatty_acid_synthase" title="Fatty acid synthase">fatty acid synthases</a> that polymerize and then reduce acetyl-CoA units. The acyl chains in the fatty acids are extended by a cycle of reactions that add the acetyl group, reduce it to an alcohol, <a href="/wiki/Dehydration_reaction" title="Dehydration reaction">dehydrate</a> it to an <a href="/wiki/Alkene" title="Alkene">alkene</a> group and then reduce it again to an <a href="/wiki/Alkane" title="Alkane">alkane</a> group. The enzymes of fatty acid biosynthesis are divided into two groups, in animals and fungi all these fatty acid synthase reactions are carried out by a single multifunctional protein,<sup id="cite_ref-Chirala_2004_84-0" class="reference"><a href="#cite_note-Chirala_2004-84"><span class="cite-bracket">[</span>84<span class="cite-bracket">]</span></a></sup> while in plant <a href="/wiki/Plastid" title="Plastid">plastids</a> and bacteria separate enzymes perform each step in the pathway.<sup id="cite_ref-White_2005_85-0" class="reference"><a href="#cite_note-White_2005-85"><span class="cite-bracket">[</span>85<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Ohlrogge_1997_86-0" class="reference"><a href="#cite_note-Ohlrogge_1997-86"><span class="cite-bracket">[</span>86<span class="cite-bracket">]</span></a></sup> The fatty acids may be subsequently converted to triglycerides that are packaged in <a href="/wiki/Lipoproteins" class="mw-redirect" title="Lipoproteins">lipoproteins</a> and secreted from the liver. </p><p>The synthesis of <a href="/wiki/Unsaturated_fatty_acid" class="mw-redirect" title="Unsaturated fatty acid">unsaturated fatty acids</a> involves a <a href="/wiki/Desaturase" class="mw-redirect" title="Desaturase">desaturation</a> reaction, whereby a double bond is introduced into the fatty acyl chain. For example, in humans, the desaturation of <a href="/wiki/Stearic_acid" title="Stearic acid">stearic acid</a> by <a href="/wiki/Stearoyl-CoA_desaturase-1" class="mw-redirect" title="Stearoyl-CoA desaturase-1">stearoyl-CoA desaturase-1</a> produces <a href="/wiki/Oleic_acid" title="Oleic acid">oleic acid</a>. The doubly unsaturated fatty acid <a href="/wiki/Linoleic_acid" title="Linoleic acid">linoleic acid</a> as well as the triply unsaturated <a href="/wiki/Alpha-Linolenic_acid" class="mw-redirect" title="Alpha-Linolenic acid">α-linolenic acid</a> cannot be synthesized in mammalian tissues, and are therefore <a href="/wiki/Essential_fatty_acid" title="Essential fatty acid">essential fatty acids</a> and must be obtained from the diet.<sup id="cite_ref-Stryer_2007_2-6" class="reference"><a href="#cite_note-Stryer_2007-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 643">: 643 </span></sup> </p><p>Triglyceride synthesis takes place in the <a href="/wiki/Endoplasmic_reticulum" title="Endoplasmic reticulum">endoplasmic reticulum</a> by metabolic pathways in which acyl groups in fatty acyl-CoAs are transferred to the hydroxyl groups of glycerol-3-phosphate and diacylglycerol.<sup id="cite_ref-Stryer_2007_2-7" class="reference"><a href="#cite_note-Stryer_2007-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 733–9">: 733–9 </span></sup> </p><p><a href="/wiki/Terpene" title="Terpene">Terpenes</a> and <a href="/wiki/Terpenoid" title="Terpenoid">isoprenoids</a>, including the <a href="/wiki/Carotenoid" title="Carotenoid">carotenoids</a>, are made by the assembly and modification of isoprene units donated from the reactive precursors <a href="/wiki/Isopentenyl_pyrophosphate" title="Isopentenyl pyrophosphate">isopentenyl pyrophosphate</a> and <a href="/wiki/Dimethylallyl_pyrophosphate" title="Dimethylallyl pyrophosphate">dimethylallyl pyrophosphate</a>.<sup id="cite_ref-Kuzuyama_2003_48-1" class="reference"><a href="#cite_note-Kuzuyama_2003-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> These precursors can be made in different ways. In animals and <a href="/wiki/Archaea" title="Archaea">archaea</a>, the <a href="/wiki/Mevalonate_pathway" title="Mevalonate pathway">mevalonate pathway</a> produces these compounds from acetyl-CoA,<sup id="cite_ref-Grochowski_2006_87-0" class="reference"><a href="#cite_note-Grochowski_2006-87"><span class="cite-bracket">[</span>87<span class="cite-bracket">]</span></a></sup> while in plants and bacteria the <a href="/wiki/Non-mevalonate_pathway" title="Non-mevalonate pathway">non-mevalonate pathway</a> uses pyruvate and <a href="/wiki/Glyceraldehyde_3-phosphate" title="Glyceraldehyde 3-phosphate">glyceraldehyde 3-phosphate</a> as substrates.<sup id="cite_ref-Kuzuyama_2003_48-2" class="reference"><a href="#cite_note-Kuzuyama_2003-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Lichtenthaler_1999_88-0" class="reference"><a href="#cite_note-Lichtenthaler_1999-88"><span class="cite-bracket">[</span>88<span class="cite-bracket">]</span></a></sup> One important reaction that uses these activated isoprene donors is <a href="/wiki/Steroid_biosynthesis" class="mw-redirect" title="Steroid biosynthesis">steroid biosynthesis</a>. Here, the isoprene units are joined together to make <a href="/wiki/Squalene" title="Squalene">squalene</a> and then folded up and formed into a set of rings to make <a href="/wiki/Lanosterol" title="Lanosterol">lanosterol</a>.<sup id="cite_ref-Schroepfer_1981_89-0" class="reference"><a href="#cite_note-Schroepfer_1981-89"><span class="cite-bracket">[</span>89<span class="cite-bracket">]</span></a></sup> Lanosterol can then be converted into other steroids such as cholesterol and ergosterol.<sup id="cite_ref-Schroepfer_1981_89-1" class="reference"><a href="#cite_note-Schroepfer_1981-89"><span class="cite-bracket">[</span>89<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Lees_1995_90-0" class="reference"><a href="#cite_note-Lees_1995-90"><span class="cite-bracket">[</span>90<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Degradation">Degradation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lipid&action=edit&section=18" title="Edit section: Degradation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Beta_oxidation" title="Beta oxidation">Beta oxidation</a> is the metabolic process by which fatty acids are broken down in the <a href="/wiki/Mitochondria" class="mw-redirect" title="Mitochondria">mitochondria</a> or in <a href="/wiki/Peroxisomes" class="mw-redirect" title="Peroxisomes">peroxisomes</a> to generate <a href="/wiki/Acetyl-CoA" title="Acetyl-CoA">acetyl-CoA</a>. For the most part, fatty acids are oxidized by a mechanism that is similar to, but not identical with, a reversal of the process of fatty acid synthesis. That is, two-carbon fragments are removed sequentially from the carboxyl end of the acid after steps of <a href="/wiki/Dehydrogenation" title="Dehydrogenation">dehydrogenation</a>, <a href="/wiki/Hydration_reaction" title="Hydration reaction">hydration</a>, and <a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">oxidation</a> to form a <a href="/wiki/Keto_acid" title="Keto acid">beta-keto acid</a>, which is split by <a href="/wiki/Thiolysis" title="Thiolysis">thiolysis</a>. The acetyl-CoA is then ultimately converted into <a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">adenosine triphosphate</a> (ATP), CO<sub>2</sub>, and H<sub>2</sub>O using the <a href="/wiki/Citric_acid_cycle" title="Citric acid cycle">citric acid cycle</a> and the <a href="/wiki/Electron_transport_chain" title="Electron transport chain">electron transport chain</a>. Hence the citric acid cycle can start at acetyl-CoA when fat is being broken down for energy if there is little or no glucose available. The energy yield of the complete oxidation of the fatty acid palmitate is 106 ATP.<sup id="cite_ref-Stryer_2007_2-8" class="reference"><a href="#cite_note-Stryer_2007-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 625–6">: 625–6 </span></sup> Unsaturated and odd-chain fatty acids require additional enzymatic steps for degradation. </p> <div class="mw-heading mw-heading2"><h2 id="Nutrition_and_health">Nutrition and health</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lipid&action=edit&section=19" title="Edit section: Nutrition and health"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Most of the fat found in food is in the form of triglycerides, cholesterol, and phospholipids. Some dietary fat is necessary to facilitate absorption of fat-soluble vitamins (<a href="/wiki/Retinol" title="Retinol">A</a>, <a href="/wiki/Calciferol" class="mw-redirect" title="Calciferol">D</a>, <a href="/wiki/Tocopherol" title="Tocopherol">E</a>, and <a href="/wiki/Phylloquinone" class="mw-redirect" title="Phylloquinone">K</a>) and <a href="/wiki/Carotenoids" class="mw-redirect" title="Carotenoids">carotenoids</a>.<sup id="cite_ref-Bhagavan_2002_91-0" class="reference"><a href="#cite_note-Bhagavan_2002-91"><span class="cite-bracket">[</span>91<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 903">: 903 </span></sup> Humans and other mammals have a dietary requirement for certain essential fatty acids, such as <a href="/wiki/Linoleic_acid" title="Linoleic acid">linoleic acid</a> (an <a href="/wiki/Omega-6_fatty_acid" title="Omega-6 fatty acid">omega-6 fatty acid</a>) and <a href="/wiki/Alpha-linolenic_acid" class="mw-redirect" title="Alpha-linolenic acid">alpha-linolenic acid</a> (an omega-3 fatty acid) because they cannot be synthesized from simple precursors in the diet.<sup id="cite_ref-Stryer_2007_2-9" class="reference"><a href="#cite_note-Stryer_2007-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 643">: 643 </span></sup> Both of these fatty acids are 18-carbon <a href="/wiki/Polyunsaturated_fat" title="Polyunsaturated fat">polyunsaturated fatty acids</a> differing in the number and position of the double bonds. Most <a href="/wiki/Vegetable_oil" title="Vegetable oil">vegetable oils</a> are rich in linoleic acid (<a href="/wiki/Safflower_oil" class="mw-redirect" title="Safflower oil">safflower</a>, <a href="/wiki/Sunflower_oil" title="Sunflower oil">sunflower</a>, and <a href="/wiki/Corn_oil" title="Corn oil">corn</a> oils). Alpha-linolenic acid is found in the green leaves of plants and in some seeds, nuts, and legumes (in particular <a href="/wiki/Linseed_oil" title="Linseed oil">flax</a>, <a href="/wiki/Rapeseed" title="Rapeseed">rapeseed</a>, <a href="/wiki/Walnut" title="Walnut">walnut</a>, and <a href="/wiki/Soy" class="mw-redirect" title="Soy">soy</a>).<sup id="cite_ref-Russo_2009_92-0" class="reference"><a href="#cite_note-Russo_2009-92"><span class="cite-bracket">[</span>92<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Fish_oil" title="Fish oil">Fish oils</a> are particularly rich in the longer-chain omega-3 fatty acids <a href="/wiki/Eicosapentaenoic_acid" title="Eicosapentaenoic acid">eicosapentaenoic acid</a> and <a href="/wiki/Docosahexaenoic_acid" title="Docosahexaenoic acid">docosahexaenoic acid</a>.<sup id="cite_ref-Bhagavan_2002_91-1" class="reference"><a href="#cite_note-Bhagavan_2002-91"><span class="cite-bracket">[</span>91<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 388">: 388 </span></sup> Many studies have shown positive health benefits associated with consumption of omega-3 fatty acids on infant development, cancer, cardiovascular diseases, and various mental illnesses (such as depression, attention-deficit hyperactivity disorder, and dementia).<sup id="cite_ref-Riediger_2009_93-0" class="reference"><a href="#cite_note-Riediger_2009-93"><span class="cite-bracket">[</span>93<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Galli_2009_94-0" class="reference"><a href="#cite_note-Galli_2009-94"><span class="cite-bracket">[</span>94<span class="cite-bracket">]</span></a></sup> </p><p>In contrast, it is now well-established that consumption of <a href="/wiki/Trans_fat" title="Trans fat">trans fats</a>, such as those present in <a href="/wiki/Partially_hydrogenated_vegetable_oil#In_the_food_industry" class="mw-redirect" title="Partially hydrogenated vegetable oil">partially hydrogenated vegetable oils</a>, are a risk factor for <a href="/wiki/Cardiovascular_disease" title="Cardiovascular disease">cardiovascular disease</a>. Fats that are good for one may be turned into trans fats by improper cooking methods that result in overcooking the lipids.<sup id="cite_ref-Micha_2008_95-0" class="reference"><a href="#cite_note-Micha_2008-95"><span class="cite-bracket">[</span>95<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Dalainas_2008_96-0" class="reference"><a href="#cite_note-Dalainas_2008-96"><span class="cite-bracket">[</span>96<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Mozaffarian_2007_97-0" class="reference"><a href="#cite_note-Mozaffarian_2007-97"><span class="cite-bracket">[</span>97<span class="cite-bracket">]</span></a></sup> </p><p>A few studies have suggested that total dietary fat intake is linked to an increased risk of obesity.<sup id="cite_ref-Astrup_2008_98-0" class="reference"><a href="#cite_note-Astrup_2008-98"><span class="cite-bracket">[</span>98<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Astrup_2005_99-0" class="reference"><a href="#cite_note-Astrup_2005-99"><span class="cite-bracket">[</span>99<span class="cite-bracket">]</span></a></sup> and diabetes;<sup id="cite_ref-Astrup_2008b_100-0" class="reference"><a href="#cite_note-Astrup_2008b-100"><span class="cite-bracket">[</span>100<span class="cite-bracket">]</span></a></sup> Others, including the Women's Health Initiative Dietary Modification Trial, an eight-year study of 49,000 women, the Nurses' Health Study, and the Health Professionals Follow-up Study, revealed no such links.<sup id="cite_ref-Beresford_2005_101-0" class="reference"><a href="#cite_note-Beresford_2005-101"><span class="cite-bracket">[</span>101<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Howard_2006_102-0" class="reference"><a href="#cite_note-Howard_2006-102"><span class="cite-bracket">[</span>102<span class="cite-bracket">]</span></a></sup> None of these studies suggested any connection between percentage of calories from fat and risk of cancer, heart disease, or weight gain. The Nutrition Source,<sup id="cite_ref-103" class="reference"><a href="#cite_note-103"><span class="cite-bracket">[</span>103<span class="cite-bracket">]</span></a></sup> a website maintained by the department of nutrition at the <a href="/wiki/Harvard_School_of_Public_Health" class="mw-redirect" title="Harvard School of Public Health">T. H. Chan School of Public Health</a> at <a href="/wiki/Harvard_University" title="Harvard University">Harvard University</a>, summarizes the current evidence on the effect of dietary fat: "Detailed research—much of it done at Harvard—shows that the total amount of fat in the diet isn't really linked with weight or disease."<sup id="cite_ref-urlFats_104-0" class="reference"><a href="#cite_note-urlFats-104"><span class="cite-bracket">[</span>104<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lipid&action=edit&section=20" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Solid_lipid_nanoparticle" title="Solid lipid nanoparticle">Solid lipid nanoparticle</a> – Novel drug delivery system</li> <li><a href="/wiki/Simple_lipid" title="Simple lipid">Simple lipid</a></li> <li><a href="/wiki/Emulsion_test" title="Emulsion test">Emulsion test</a></li> <li><a href="/wiki/Lipid_microdomain" title="Lipid microdomain">Lipid microdomain</a></li> <li><a href="/wiki/Membrane_lipid" title="Membrane lipid">Membrane lipid</a> – Lipid molecules on cell membrane</li> <li><a href="/wiki/Lipidomics" title="Lipidomics">Lipidomics</a> – large scale study of an organism's lipid metabolism using high-end chemical analysis techniques<span style="display:none" class="category-wikidata-fallback-annotation">Pages displaying wikidata descriptions as a fallback</span> <ul><li><a href="/wiki/Lipidome" title="Lipidome">Lipidome</a> – Totality of lipids in cells</li></ul></li> <li><a href="/wiki/Protein%E2%80%93lipid_interaction" title="Protein–lipid interaction">Protein–lipid interaction</a></li> <li><a href="/wiki/Phenolic_lipid" title="Phenolic lipid">Phenolic lipid</a> – Class of organic compounds, a class of natural products composed of long aliphatic chains and phenolic rings that occur in plants, fungi and bacteria</li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lipid&action=edit&section=21" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist reflist-columns references-column-width" style="column-width: 30em;"> <ol class="references"> <li id="cite_note-Maitland_1998-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-Maitland_1998_1-0">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .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="CITEREFMaitland1998" class="citation book cs1">Maitland J Jr (1998). <i>Organic Chemistry</i>. W W Norton & Co Inc (Np). p. 139. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-393-97378-5" title="Special:BookSources/978-0-393-97378-5"><bdi>978-0-393-97378-5</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Organic+Chemistry&rft.pages=139&rft.pub=W+W+Norton+%26+Co+Inc+%28Np%29&rft.date=1998&rft.isbn=978-0-393-97378-5&rft.aulast=Maitland&rft.aufirst=J+Jr&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALipid" class="Z3988"></span></span> </li> <li id="cite_note-Stryer_2007-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-Stryer_2007_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Stryer_2007_2-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Stryer_2007_2-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Stryer_2007_2-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-Stryer_2007_2-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-Stryer_2007_2-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-Stryer_2007_2-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-Stryer_2007_2-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-Stryer_2007_2-8"><sup><i><b>i</b></i></sup></a> <a href="#cite_ref-Stryer_2007_2-9"><sup><i><b>j</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFStryerBergTymoczko2007" class="citation book cs1">Stryer L, Berg JM, Tymoczko JL (2007). <i>Biochemistry</i> (6th ed.). 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Freeman. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-7167-8724-2" title="Special:BookSources/978-0-7167-8724-2"><bdi>978-0-7167-8724-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Biochemistry&rft.place=San+Francisco&rft.edition=6th&rft.pub=W.H.+Freeman&rft.date=2007&rft.isbn=978-0-7167-8724-2&rft.aulast=Stryer&rft.aufirst=L&rft.au=Berg%2C+JM&rft.au=Tymoczko%2C+JL&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALipid" class="Z3988"></span></span> </li> <li id="cite_note-Fahy_2009-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-Fahy_2009_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Fahy_2009_3-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Fahy_2009_3-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Fahy_2009_3-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><link 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Harvard School of Public Health.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Fats+and+Cholesterol%3A+Out+with+the+Bad%2C+In+with+the+Good+%E2%80%94+What+Should+You+Eat%3F+%E2%80%93+The+Nutrition+Source&rft.pub=Harvard+School+of+Public+Health&rft_id=https%3A%2F%2Fwww.hsph.harvard.edu%2Fnutritionsource%2Fwhat-should-you-eat%2Ffats-full-story%2Findex.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALipid" class="Z3988"></span></span> </li> </ol></div> <div class="mw-heading mw-heading3"><h3 id="Bibliography">Bibliography</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lipid&action=edit&section=22" title="Edit section: Bibliography"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="Bhagavan" class="citation book cs1">Bhagavan NV (2002). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=vT9YttFTPi0C"><i>Medical Biochemistry</i></a>. San Diego: Harcourt/Academic Press. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-12-095440-7" title="Special:BookSources/978-0-12-095440-7"><bdi>978-0-12-095440-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Medical+Biochemistry&rft.place=San+Diego&rft.pub=Harcourt%2FAcademic+Press&rft.date=2002&rft.isbn=978-0-12-095440-7&rft.aulast=Bhagavan&rft.aufirst=NV&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DvT9YttFTPi0C&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALipid" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="Devlin" class="citation book cs1">Devlin TM (1997). <i>Textbook of Biochemistry: With Clinical Correlations</i> (4th ed.). Chichester: John Wiley & Sons. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-471-17053-2" title="Special:BookSources/978-0-471-17053-2"><bdi>978-0-471-17053-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Textbook+of+Biochemistry%3A+With+Clinical+Correlations&rft.place=Chichester&rft.edition=4th&rft.pub=John+Wiley+%26+Sons&rft.date=1997&rft.isbn=978-0-471-17053-2&rft.aulast=Devlin&rft.aufirst=TM&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALipid" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="Stryer" class="citation book cs1">Stryer L, Berg JM, Tymoczko JL (2007). <i>Biochemistry</i> (6th ed.). San Francisco: W.H. Freeman. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-7167-8724-2" title="Special:BookSources/978-0-7167-8724-2"><bdi>978-0-7167-8724-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Biochemistry&rft.place=San+Francisco&rft.edition=6th&rft.pub=W.H.+Freeman&rft.date=2007&rft.isbn=978-0-7167-8724-2&rft.aulast=Stryer&rft.aufirst=L&rft.au=Berg%2C+JM&rft.au=Tymoczko%2C+JL&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALipid" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="Holde" class="citation book cs1">van Holde KE, Mathews CK (1996). <a rel="nofollow" class="external text" href="https://archive.org/details/biochemistry00math"><i>Biochemistry</i></a> (2nd ed.). Menlo Park, California: Benjamin/Cummings Pub. Co. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-8053-3931-4" title="Special:BookSources/978-0-8053-3931-4"><bdi>978-0-8053-3931-4</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Biochemistry&rft.place=Menlo+Park%2C+California&rft.edition=2nd&rft.pub=Benjamin%2FCummings+Pub.+Co&rft.date=1996&rft.isbn=978-0-8053-3931-4&rft.aulast=van+Holde&rft.aufirst=KE&rft.au=Mathews%2C+CK&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Fbiochemistry00math&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALipid" class="Z3988"></span></li></ul> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lipid&action=edit&section=23" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1235681985">.mw-parser-output .side-box{margin:4px 0;box-sizing:border-box;border:1px solid #aaa;font-size:88%;line-height:1.25em;background-color:var(--background-color-interactive-subtle,#f8f9fa);display:flow-root}.mw-parser-output .side-box-abovebelow,.mw-parser-output .side-box-text{padding:0.25em 0.9em}.mw-parser-output .side-box-image{padding:2px 0 2px 0.9em;text-align:center}.mw-parser-output .side-box-imageright{padding:2px 0.9em 2px 0;text-align:center}@media(min-width:500px){.mw-parser-output .side-box-flex{display:flex;align-items:center}.mw-parser-output .side-box-text{flex:1;min-width:0}}@media(min-width:720px){.mw-parser-output .side-box{width:238px}.mw-parser-output .side-box-right{clear:right;float:right;margin-left:1em}.mw-parser-output .side-box-left{margin-right:1em}}</style><style data-mw-deduplicate="TemplateStyles:r1237033735">@media print{body.ns-0 .mw-parser-output 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srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/99/Wiktionary-logo-en-v2.svg/60px-Wiktionary-logo-en-v2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/99/Wiktionary-logo-en-v2.svg/80px-Wiktionary-logo-en-v2.svg.png 2x" data-file-width="512" data-file-height="512" /></span></span></div> <div class="side-box-text plainlist">Look up <i><b><a href="https://en.wiktionary.org/wiki/lipid" class="extiw" title="wiktionary:lipid">lipid</a></b></i> in Wiktionary, the free dictionary.</div></div> </div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1235681985"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1237033735"><div class="side-box side-box-right plainlinks sistersitebox"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"> <div class="side-box-flex"> <div class="side-box-image"><span class="noviewer" typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/30px-Commons-logo.svg.png" decoding="async" width="30" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/45px-Commons-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/59px-Commons-logo.svg.png 2x" data-file-width="1024" data-file-height="1376" /></span></span></div> <div class="side-box-text plainlist">Wikimedia Commons has media related to <span style="font-weight: bold; font-style: italic;"><a href="https://commons.wikimedia.org/wiki/Category:Lipids" class="extiw" title="commons:Category:Lipids">Lipids</a></span>.</div></div> </div> <p><b>Introductory</b> </p> <ul><li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20100818084308/http://www.cyberlipid.org/cyberlip/link0041.htm">List of lipid-related web sites</a></li> <li><a rel="nofollow" class="external text" href="http://www.lipidmaps.org/">Nature Lipidomics Gateway</a> – Round-up and summaries of recent lipid research</li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20060414162931/http://www.lipidlibrary.co.uk/">Lipid Library</a> – General reference on lipid chemistry and biochemistry</li> <li><a rel="nofollow" class="external text" href="http://www.cyberlipid.org/">Cyberlipid.org</a> – Resources and history for lipids.</li> <li><a rel="nofollow" class="external text" href="http://www.fos.su.se/~sasha/Lipid_membranes.html">Molecular Computer Simulations</a> – Modeling of Lipid Membranes</li> <li><a rel="nofollow" class="external text" href="http://biochemweb.fenteany.com/lipids_membranes.shtml">Lipids, Membranes and Vesicle Trafficking</a> – The Virtual Library of Biochemistry, Molecular Biology and Cell Biology</li></ul> <p><b>Nomenclature</b> </p> <ul><li><a rel="nofollow" class="external text" href="http://www.chem.qmul.ac.uk/iupac/lipid/">IUPAC nomenclature of lipids</a></li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20110406044322/http://www.chem.qmul.ac.uk/iupac/class/lipid.html">IUPAC glossary entry for the lipid class of molecules</a></li></ul> <p><b>Databases</b> </p> <ul><li><a rel="nofollow" class="external text" href="http://www.lipidmaps.org/data/databases.html">LIPID MAPS</a> – Comprehensive lipid and lipid-associated gene/protein databases.</li> <li><a rel="nofollow" class="external text" href="http://lipidbank.jp/">LipidBank</a> – Japanese database of lipids and related properties, spectral data and references.</li></ul> <p><b>General</b> </p> <ul><li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20050720194241/http://www.apollolipids.org/">ApolloLipids</a> – Provides dyslipidemia and cardiovascular disease prevention and treatment information as well as continuing medical education programs</li> <li><a rel="nofollow" class="external text" href="http://www.lipid.org/">National Lipid Association</a> – Professional medical education organization for health care professionals who seek to prevent morbidity and mortality stemming from dyslipidemias and other cholesterol-related disorders.</li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol dl,.mw-parser-output .hlist ol ol,.mw-parser-output .hlist ol ul,.mw-parser-output .hlist ul dl,.mw-parser-output .hlist ul ol,.mw-parser-output .hlist ul ul{display:inline}.mw-parser-output .hlist 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.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:Lipids" title="Template:Lipids"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Lipids" title="Template talk:Lipids"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Lipids" title="Special:EditPage/Template:Lipids"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Types_of_lipids" style="font-size:114%;margin:0 4em">Types of <a class="mw-selflink selflink">lipids</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">General</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Saturation</i>: <a href="/wiki/Saturated_fat" title="Saturated fat">Saturated fat</a></li> <li><a href="/wiki/Unsaturated_fat" title="Unsaturated fat">Unsaturated fat</a></li> <li><a href="/wiki/Monounsaturated_fatty_acid" class="mw-redirect" title="Monounsaturated fatty acid">Monounsaturated fatty acid</a></li> <li><a href="/wiki/Polyunsaturated_fatty_acid" class="mw-redirect" title="Polyunsaturated fatty acid">Polyunsaturated fatty acid</a></li> <li><a href="/wiki/Essential_fatty_acid" title="Essential fatty acid">Essential fatty acid</a></li> <li><i>Other</i>: <a href="/wiki/Fat" title="Fat">Fat</a></li> <li><a href="/wiki/Oil" title="Oil">Oil</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Geometry</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Trans_fat" title="Trans fat">Trans fat</a></li> <li><a href="/wiki/Omega-3_fatty_acid" title="Omega-3 fatty acid">Omega−3 fatty acid</a></li> <li><a href="/wiki/Omega-6_fatty_acid" title="Omega-6 fatty acid">Omega−6 fatty acid</a></li> <li><a href="/wiki/Omega-9_fatty_acid" title="Omega-9 fatty acid">Omega−9 fatty acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Eicosanoid" title="Eicosanoid">Eicosanoids</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/Arachidonic_acid" title="Arachidonic acid">Arachidonic acid</a></li> <li><a href="/wiki/Prostaglandin" title="Prostaglandin">Prostaglandins</a></li> <li><a href="/wiki/Prostacyclin" title="Prostacyclin">Prostacyclin</a></li> <li><a href="/wiki/Thromboxane" title="Thromboxane">Thromboxane</a></li> <li><a href="/wiki/Leukotriene" title="Leukotriene">Leukotrienes</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Fatty_acid" title="Fatty acid">Fatty acids</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/Caprylic_acid" title="Caprylic acid">Caprylic acid</a></li> <li><a href="/wiki/Capric_acid" title="Capric acid">Capric acid</a></li> <li><a href="/wiki/Lauric_acid" title="Lauric acid">Lauric acid</a></li> <li><a href="/wiki/Myristic_acid" title="Myristic acid">Myristic acid</a></li> <li><a href="/wiki/Palmitic_acid" title="Palmitic acid">Palmitic acid</a></li> <li><a href="/wiki/Stearic_acid" title="Stearic acid">Stearic acid</a></li> <li><a href="/wiki/Arachidic_acid" title="Arachidic acid">Arachidic acid</a></li> <li><a href="/wiki/Behenic_acid" title="Behenic acid">Behenic acid</a></li> <li><a href="/wiki/Lignoceric_acid" title="Lignoceric acid">Lignoceric acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Glyceride" title="Glyceride">Glycerides</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/Monoglyceride" title="Monoglyceride">Monoglyceride</a></li> <li><a href="/wiki/Diglyceride" title="Diglyceride">Diglyceride</a></li> <li><a href="/wiki/Triglyceride" title="Triglyceride">Triglyceride</a> <ul><li><a href="/wiki/Triheptanoin" title="Triheptanoin">Triheptanoin</a></li> <li><a href="/wiki/Trimyristin" title="Trimyristin">Trimyristin</a></li> <li><a href="/wiki/Tripalmitin" title="Tripalmitin">Tripalmitin</a></li> <li><a href="/wiki/Stearin" title="Stearin">Tristearin</a></li> <li><a href="/wiki/Linolein" title="Linolein">Trilinolein</a></li> <li><a href="/wiki/Triolein" title="Triolein">Triolein</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phospholipid" title="Phospholipid">Phospholipids</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/Phosphatidylserine" title="Phosphatidylserine">Phosphatidylserine</a></li> <li><a href="/wiki/Phosphatidylinositol" title="Phosphatidylinositol">Phosphatidylinositol</a></li> <li><a href="/wiki/Phosphatidylethanolamine" title="Phosphatidylethanolamine">Phosphatidyl ethanolamine</a></li> <li><a href="/wiki/Cardiolipin" title="Cardiolipin">Cardiolipin</a></li> <li><a href="/wiki/Dipalmitoylphosphatidylcholine" title="Dipalmitoylphosphatidylcholine">Dipalmitoylphosphatidylcholine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sphingolipid" title="Sphingolipid">Sphingolipids</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/Ceramide" title="Ceramide">Ceramide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Steroid" title="Steroid">Steroids</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/Cholesterol" title="Cholesterol">Cholesterol</a></li> <li><a href="/wiki/Corticosteroid" title="Corticosteroid">Corticosteroids</a></li> <li><a href="/wiki/Sex_steroid" class="mw-redirect" title="Sex steroid">Sex steroids</a></li> <li><a href="/wiki/Secosteroid" title="Secosteroid">Secosteroids</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Lipids:_fatty_acids" 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:Fatty_acids" title="Template:Fatty acids"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Fatty_acids" title="Template talk:Fatty acids"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Fatty_acids" title="Special:EditPage/Template:Fatty acids"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Lipids:_fatty_acids" style="font-size:114%;margin:0 4em"><a class="mw-selflink selflink">Lipids</a>: <a href="/wiki/Fatty_acid" title="Fatty acid">fatty acids</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Saturated_fat" title="Saturated fat">Saturated</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Propionic_acid" title="Propionic acid">Propionic</a> (C3)</li> <li><a href="/wiki/Butyric_acid" title="Butyric acid">Butyric</a> (C4)</li> <li><a href="/wiki/Valeric_acid" title="Valeric acid">Valeric</a> (C5)</li> <li><a href="/wiki/Caproic_acid" title="Caproic acid">Caproic</a> (C6)</li> <li><a href="/wiki/Enanthic_acid" title="Enanthic acid">Enanthic</a> (C7)</li> <li><a href="/wiki/Caprylic_acid" title="Caprylic acid">Caprylic</a> (C8)</li> <li><a href="/wiki/Pelargonic_acid" title="Pelargonic acid">Pelargonic</a> (C9)</li> <li><a href="/wiki/Capric_acid" title="Capric acid">Capric</a> (C10)</li> <li><a href="/wiki/Undecylic_acid" title="Undecylic acid">Undecylic</a> (C11)</li> <li><a href="/wiki/Lauric_acid" title="Lauric acid">Lauric</a> (C12)</li> <li><a href="/wiki/Tridecylic_acid" title="Tridecylic acid">Tridecylic</a> (C13)</li> <li><a href="/wiki/Myristic_acid" title="Myristic acid">Myristic</a> (C14)</li> <li><a href="/wiki/Pentadecylic_acid" title="Pentadecylic acid">Pentadecylic</a> (C15)</li> <li><a href="/wiki/Palmitic_acid" title="Palmitic acid">Palmitic</a> (C16)</li> <li><a href="/wiki/Margaric_acid" title="Margaric acid">Margaric</a> (C17)</li> <li><a href="/wiki/Stearic_acid" title="Stearic acid">Stearic</a> (C18)</li> <li><a href="/wiki/Nonadecylic_acid" title="Nonadecylic acid">Nonadecylic</a> (C19)</li> <li><a href="/wiki/Arachidic_acid" title="Arachidic acid">Arachidic</a> (C20)</li> <li><a href="/wiki/Heneicosylic_acid" title="Heneicosylic acid">Heneicosylic</a> (C21)</li> <li><a href="/wiki/Behenic_acid" title="Behenic acid">Behenic</a> (C22)</li> <li><a href="/wiki/Tricosylic_acid" title="Tricosylic acid">Tricosylic</a> (C23)</li> <li><a href="/wiki/Lignoceric_acid" title="Lignoceric acid">Lignoceric</a> (C24)</li> <li><a href="/wiki/Pentacosylic_acid" title="Pentacosylic acid">Pentacosylic</a> (C25)</li> <li><a href="/wiki/Cerotic_acid" title="Cerotic acid">Cerotic</a> (C26)</li> <li><a href="/wiki/Carboceric_acid" title="Carboceric acid">Carboceric</a> (C27)</li> <li><a href="/wiki/Montanic_acid" title="Montanic acid">Montanic</a> (C28)</li> <li><a href="/wiki/Nonacosylic_acid" title="Nonacosylic acid">Nonacosylic</a> (C29)</li> <li><a href="/wiki/Melissic_acid" title="Melissic acid">Melissic</a> (C30)</li> <li><a href="/wiki/Hentriacontylic_acid" title="Hentriacontylic acid">Hentriacontylic</a> (C31)</li> <li><a href="/wiki/Lacceroic_acid" title="Lacceroic acid">Lacceroic</a> (C32)</li> <li><a href="/wiki/Psyllic_acid" title="Psyllic acid">Psyllic</a> (C33)</li> <li><a href="/wiki/Geddic_acid" title="Geddic acid">Geddic</a> (C34)</li> <li><a href="/wiki/Ceroplastic_acid" title="Ceroplastic acid">Ceroplastic</a> (C35)</li> <li><a href="/wiki/Hexatriacontylic_acid" title="Hexatriacontylic acid">Hexatriacontylic</a> (C36)</li> <li><a href="/wiki/Heptatriacontanoic_acid" title="Heptatriacontanoic acid">Heptatriacontanoic</a> (C37)</li> <li><a href="/w/index.php?title=Octatriacontanoic_acid&action=edit&redlink=1" class="new" title="Octatriacontanoic acid (page does not exist)">Octatriacontanoic</a> (C38)</li> <li><a href="/w/index.php?title=Nonatriacontanoic_acid&action=edit&redlink=1" class="new" title="Nonatriacontanoic acid (page does not exist)">Nonatriacontanoic</a> (C39)</li> <li><a href="/w/index.php?title=Tetracontanoic_acid&action=edit&redlink=1" class="new" title="Tetracontanoic acid (page does not exist)">Tetracontanoic</a> (C40)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Omega-3_fatty_acid" title="Omega-3 fatty acid">ω−3 Unsaturated</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=5-Octenoic_acid&action=edit&redlink=1" class="new" title="5-Octenoic acid (page does not exist)">Octenoic</a> (8:1)</li> <li><a href="/w/index.php?title=7-Decenoic_acid&action=edit&redlink=1" class="new" title="7-Decenoic acid (page does not exist)">Decenoic</a> (10:1)</li> <li><a href="/w/index.php?title=4,7-Decadienoic_acid&action=edit&redlink=1" class="new" title="4,7-Decadienoic acid (page does not exist)">Decadienoic</a> (10:2)</li> <li><a href="/w/index.php?title=9-Dodecenoic_acid&action=edit&redlink=1" class="new" title="9-Dodecenoic acid (page does not exist)">Lauroleic</a> (12:1)</li> <li><a href="/w/index.php?title=6,9-Dodecadienoic_acid&action=edit&redlink=1" class="new" title="6,9-Dodecadienoic acid (page does not exist)">Laurolinoleic</a> (12:2)</li> <li><a href="/w/index.php?title=11-Tetradecenoic_acid&action=edit&redlink=1" class="new" title="11-Tetradecenoic acid (page does not exist)">Myristovaccenic</a> (14:1)</li> <li><a href="/w/index.php?title=8,11-Tetradecadienoic_acid&action=edit&redlink=1" class="new" title="8,11-Tetradecadienoic acid (page does not exist)">Myristolinoleic</a> (14:2)</li> <li><a href="/w/index.php?title=5,8,11-Tetradecatrienoic_acid&action=edit&redlink=1" class="new" title="5,8,11-Tetradecatrienoic acid (page does not exist)">Myristolinolenic</a> (14:3)</li> <li><a href="/w/index.php?title=7,10,13-Hexadecatrienoic_acid&action=edit&redlink=1" class="new" title="7,10,13-Hexadecatrienoic acid (page does not exist)">Palmitolinolenic</a> (16:3)</li> <li><a href="/w/index.php?title=4,7,10,13-Hexadecatetraenoic_acid&action=edit&redlink=1" class="new" title="4,7,10,13-Hexadecatetraenoic acid (page does not exist)">Palmitidonic</a> (16:4)</li> <li><a href="/wiki/%CE%91-Linolenic_acid" title="Α-Linolenic acid">α-Linolenic</a> (18:3)</li> <li><a href="/wiki/Stearidonic_acid" title="Stearidonic acid">Stearidonic</a> (18:4)</li> <li><a href="/wiki/%CE%91-Parinaric_acid" title="Α-Parinaric acid">α-Parinaric</a> (18:4)</li> <li><a href="/w/index.php?title=11,14,17-Eicosatrienoic_acid&action=edit&redlink=1" class="new" title="11,14,17-Eicosatrienoic acid (page does not exist)">Dihomo-α-linolenic</a> (20:3)</li> <li><a href="/wiki/Eicosatetraenoic_acid" title="Eicosatetraenoic acid">Eicosatetraenoic</a> (20:4)</li> <li><a href="/wiki/Eicosapentaenoic_acid" title="Eicosapentaenoic acid">Eicosapentaenoic</a> (20:5)</li> <li><a href="/wiki/Docosapentaenoic_acid" title="Docosapentaenoic acid">Clupanodonic</a> (22:5)</li> <li><a href="/wiki/Docosahexaenoic_acid" title="Docosahexaenoic acid">Docosahexaenoic</a> (22:6)</li> <li><a href="/w/index.php?title=9,12,15,18,21-Tetracosapentaenoic_acid&action=edit&redlink=1" class="new" title="9,12,15,18,21-Tetracosapentaenoic acid (page does not exist)">9,12,15,18,21-Tetracosapentaenoic</a> (24:5)</li> <li><a href="/w/index.php?title=6,9,12,15,18,21-Tetracosahexaenoic_acid&action=edit&redlink=1" class="new" title="6,9,12,15,18,21-Tetracosahexaenoic acid (page does not exist)">6,9,12,15,18,21-Tetracosahexaenoic</a> (24:6)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/w/index.php?title=Omega-5_fatty_acid&action=edit&redlink=1" class="new" title="Omega-5 fatty acid (page does not exist)">ω−5 Unsaturated</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Myristoleic_acid" title="Myristoleic acid">Myristoleic</a> (14:1)</li> <li><a href="/w/index.php?title=11-Hexadecenoic_acid&action=edit&redlink=1" class="new" title="11-Hexadecenoic acid (page does not exist)">Palmitovaccenic</a> (16:1)</li> <li><a href="/wiki/%CE%91-Eleostearic_acid" title="Α-Eleostearic acid">α-Eleostearic</a> (18:3)</li> <li><a href="/wiki/%CE%92-Eleostearic_acid" title="Β-Eleostearic acid">β-Eleostearic</a> (<i>trans</i>-18:3)</li> <li><a href="/wiki/Punicic_acid" title="Punicic acid">Punicic</a> (18:3)</li> <li><a href="/w/index.php?title=7,10,13-Octadecatrienoic_acid&action=edit&redlink=1" class="new" title="7,10,13-Octadecatrienoic acid (page does not exist)">7,10,13-Octadecatrienoic</a> (18:3)</li> <li><a href="/w/index.php?title=9,12,15-Eicosatrienoic_acid&action=edit&redlink=1" class="new" title="9,12,15-Eicosatrienoic acid (page does not exist)">9,12,15-Eicosatrienoic</a> (20:3)</li> <li><a href="/w/index.php?title=6,9,12,15-Eicosatetraenoic_acid&action=edit&redlink=1" class="new" title="6,9,12,15-Eicosatetraenoic acid (page does not exist)">β-Eicosatetraenoic</a> (20:4)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Omega-6_fatty_acid" title="Omega-6 fatty acid">ω−6 Unsaturated</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=8-Tetradecenoic_acid&action=edit&redlink=1" class="new" title="8-Tetradecenoic acid (page does not exist)">8-Tetradecenoic</a> (14:1)</li> <li><a href="/w/index.php?title=12-Octadecenoic_acid&action=edit&redlink=1" class="new" title="12-Octadecenoic acid (page does not exist)">12-Octadecenoic</a> (18:1)</li> <li><a href="/wiki/Linoleic_acid" title="Linoleic acid">Linoleic</a> (18:2)</li> <li><a href="/wiki/Linolelaidic_acid" title="Linolelaidic acid">Linolelaidic</a> (<i>trans</i>-18:2)</li> <li><a href="/wiki/Gamma-Linolenic_acid" class="mw-redirect" title="Gamma-Linolenic acid">γ-Linolenic</a> (18:3)</li> <li><a href="/wiki/Calendic_acid" title="Calendic acid">Calendic</a> (18:3)</li> <li><a href="/wiki/Pinolenic_acid" title="Pinolenic acid">Pinolenic</a> (18:3)</li> <li><a href="/w/index.php?title=Dihomo-linoleic_acid&action=edit&redlink=1" class="new" title="Dihomo-linoleic acid (page does not exist)">Dihomo-linoleic</a> (20:2)</li> <li><a href="/wiki/Dihomo-%CE%B3-linolenic_acid" title="Dihomo-γ-linolenic acid">Dihomo-γ-linolenic</a> (20:3)</li> <li><a href="/wiki/Sciadonic_acid" title="Sciadonic acid">Sciadonic</a> (20:3)</li> <li><a href="/wiki/Arachidonic_acid" title="Arachidonic acid">Arachidonic</a> (20:4)</li> <li><a href="/wiki/Docosatetraenoic_acid" title="Docosatetraenoic acid">Adrenic</a> (22:4)</li> <li><a href="/wiki/Docosapentaenoic_acid" title="Docosapentaenoic acid">Osbond</a> (22:5)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Omega-7_fatty_acid" title="Omega-7 fatty acid">ω−7 Unsaturated</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Palmitoleic_acid" title="Palmitoleic acid">Palmitoleic</a> (16:1)</li> <li><a href="/wiki/Vaccenic_acid" title="Vaccenic acid">Vaccenic</a> (18:1)</li> <li><a href="/wiki/Rumenic_acid" title="Rumenic acid">Rumenic</a> (18:2)</li> <li><a href="/wiki/Paullinic_acid" title="Paullinic acid">Paullinic</a> (20:1)</li> <li><a href="/w/index.php?title=7,10,13-Eicosatrienoic_acid&action=edit&redlink=1" class="new" title="7,10,13-Eicosatrienoic acid (page does not exist)">7,10,13-Eicosatrienoic</a> (20:3)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Omega-9_fatty_acid" title="Omega-9 fatty acid">ω−9 Unsaturated</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Oleic_acid" title="Oleic acid">Oleic</a> (18:1)</li> <li><a href="/wiki/Elaidic_acid" title="Elaidic acid">Elaidic</a> (<i>trans</i>-18:1)</li> <li><a href="/wiki/11-Eicosenoic_acid" title="11-Eicosenoic acid">Gondoic</a> (20:1)</li> <li><a href="/wiki/Erucic_acid" title="Erucic acid">Erucic</a> (22:1)</li> <li><a href="/wiki/Nervonic_acid" title="Nervonic acid">Nervonic</a> (24:1)</li> <li><a href="/w/index.php?title=8,11-Eicosadienoic_acid&action=edit&redlink=1" class="new" title="8,11-Eicosadienoic acid (page does not exist)">8,11-Eicosadienoic</a> (20:2)</li> <li><a href="/wiki/Mead_acid" title="Mead acid">Mead</a> (20:3)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/w/index.php?title=Omega-10_fatty_acid&action=edit&redlink=1" class="new" title="Omega-10 fatty acid (page does not exist)">ω−10 Unsaturated</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Sapienic_acid" title="Sapienic acid">Sapienic</a> (16:1)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/w/index.php?title=Omega-11_fatty_acid&action=edit&redlink=1" class="new" title="Omega-11 fatty acid (page does not exist)">ω−11 Unsaturated</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Gadoleic_acid" title="Gadoleic acid">Gadoleic</a> (20:1)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/w/index.php?title=Omega-12_fatty_acid&action=edit&redlink=1" class="new" title="Omega-12 fatty acid (page does not exist)">ω−12 Unsaturated</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=4-Hexadecenoic_acid&action=edit&redlink=1" class="new" title="4-Hexadecenoic acid (page does not exist)">4-Hexadecenoic</a> (16:1)</li> <li><a href="/wiki/Petroselinic_acid" title="Petroselinic acid">Petroselinic</a> (18:1)</li> <li><a href="/w/index.php?title=8-Eicosenoic_acid&action=edit&redlink=1" class="new" title="8-Eicosenoic acid (page does not exist)">8-Eicosenoic</a> (20:1)</li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Lipids:_lipoprotein_particle_metabolism" 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="3"><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:Lipoprotein_metabolism" title="Template:Lipoprotein metabolism"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Lipoprotein_metabolism" title="Template talk:Lipoprotein metabolism"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Lipoprotein_metabolism" title="Special:EditPage/Template:Lipoprotein metabolism"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Lipids:_lipoprotein_particle_metabolism" style="font-size:114%;margin:0 4em"><a class="mw-selflink selflink">Lipids</a>: <a href="/wiki/Lipoprotein" title="Lipoprotein">lipoprotein</a> particle metabolism</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Lipoprotein" title="Lipoprotein">Lipoprotein</a> particle classes<br /> and subclasses</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>delivery of <a href="/wiki/Triglyceride" title="Triglyceride">TGs</a>: <a href="/wiki/Chylomicron" title="Chylomicron">Chylomicron</a></li> <li><a href="/wiki/Very_low-density_lipoprotein" title="Very low-density lipoprotein">VLDL</a></li> <li>delivery of <a href="/wiki/Cholesterol" title="Cholesterol">C</a> and <a href="/wiki/Cholesteryl_ester" title="Cholesteryl ester">CE</a>: <a href="/wiki/Intermediate-density_lipoprotein" title="Intermediate-density lipoprotein">IDL</a></li> <li><a href="/wiki/Low-density_lipoprotein" title="Low-density lipoprotein">LDL</a></li> <li>lb LDL</li> <li>sd LDL</li> <li><a href="/wiki/Lipoprotein(a)" title="Lipoprotein(a)">Lp(a)</a></li> <li><a href="/wiki/High-density_lipoprotein" title="High-density lipoprotein">HDL</a></li> <li><a href="/wiki/Remnant_cholesterol" title="Remnant cholesterol">Remnant cholesterol</a></li></ul> </div></td><td class="noviewer navbox-image" rowspan="6" style="width:1px;padding:0 0 0 2px"><div><span typeof="mw:File"><a href="/wiki/File:2512_Chylomicrons_Contain_Triglycerides_Cholesterol_Molecules_and_Other_Lipids.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/ab/2512_Chylomicrons_Contain_Triglycerides_Cholesterol_Molecules_and_Other_Lipids.jpg/350px-2512_Chylomicrons_Contain_Triglycerides_Cholesterol_Molecules_and_Other_Lipids.jpg" decoding="async" width="350" height="280" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/ab/2512_Chylomicrons_Contain_Triglycerides_Cholesterol_Molecules_and_Other_Lipids.jpg/525px-2512_Chylomicrons_Contain_Triglycerides_Cholesterol_Molecules_and_Other_Lipids.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/ab/2512_Chylomicrons_Contain_Triglycerides_Cholesterol_Molecules_and_Other_Lipids.jpg/700px-2512_Chylomicrons_Contain_Triglycerides_Cholesterol_Molecules_and_Other_Lipids.jpg 2x" data-file-width="1228" data-file-height="981" /></a></span></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Apolipoprotein" title="Apolipoprotein">Apolipoproteins</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>APOA <ul><li><a href="/wiki/Apolipoprotein_AI" title="Apolipoprotein AI">1</a></li> <li><a href="/wiki/APOA2" class="mw-redirect" title="APOA2">2</a></li> <li><a href="/wiki/APOA4" title="APOA4">4</a></li> <li><a href="/wiki/APOA5" title="APOA5">5</a></li></ul></li> <li><a href="/wiki/Apolipoprotein_B" title="Apolipoprotein B">APOB</a></li> <li>APOC <ul><li><a href="/wiki/Apolipoprotein_C1" class="mw-redirect" title="Apolipoprotein C1">1</a></li> <li><a href="/wiki/Apolipoprotein_C2" class="mw-redirect" title="Apolipoprotein C2">2</a></li> <li><a href="/wiki/Apolipoprotein_C3" class="mw-redirect" title="Apolipoprotein C3">3</a></li> <li><a href="/wiki/Apolipoprotein_C4" class="mw-redirect" title="Apolipoprotein C4">4</a></li></ul></li> <li><a href="/wiki/Apolipoprotein_D" title="Apolipoprotein D">APOD</a></li> <li><a href="/wiki/Apolipoprotein_E" title="Apolipoprotein E">APOE</a></li> <li><a href="/wiki/Apolipoprotein_H" title="Apolipoprotein H">APOH</a></li> <li><a href="/wiki/Serum_amyloid_A" title="Serum amyloid A">SAA</a> <ul><li><a href="/wiki/Serum_amyloid_A1" title="Serum amyloid A1">SAA1</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Extracellular <a href="/wiki/Enzyme" title="Enzyme">enzymes</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/Lecithin%E2%80%94cholesterol_acyltransferase" class="mw-redirect" title="Lecithin—cholesterol acyltransferase">LCAT</a></li> <li><a href="/wiki/Hepatic_lipase" title="Hepatic lipase">LIPC</a></li> <li><a href="/wiki/Lipoprotein_lipase" title="Lipoprotein lipase">LPL</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Plant_lipid_transfer_proteins" title="Plant lipid transfer proteins">Lipid transfer proteins</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/Cholesterylester_transfer_protein" class="mw-redirect" title="Cholesterylester transfer protein">CETP</a></li> <li><a href="/wiki/Microsomal_triglyceride_transfer_protein" title="Microsomal triglyceride transfer protein">MTTP</a></li> <li><a href="/wiki/Phospholipid_transfer_protein" title="Phospholipid transfer protein">PLTP</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cell_surface_receptor" title="Cell surface receptor">Cell surface receptors</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>HDL: <a href="/wiki/SCARB1" title="SCARB1">SCARB1</a></li></ul> <ul><li>IDL: <a href="/wiki/Lipoprotein_receptor-related_protein" title="Lipoprotein receptor-related protein">LRP</a> <ul><li><a href="/wiki/LRP1" title="LRP1">LRP1</a></li> <li><a href="/wiki/LRP1B" title="LRP1B">LRP1B</a></li> <li><a href="/wiki/LRP2" title="LRP2">LRP2</a></li> <li><a href="/wiki/LRP3" title="LRP3">LRP3</a></li> <li><a href="/wiki/Low-density_lipoprotein_receptor-related_protein_4" title="Low-density lipoprotein receptor-related protein 4">LRP4</a></li> <li><a href="/wiki/LRP5" title="LRP5">LRP5</a></li> <li><a href="/w/index.php?title=LRP5L&action=edit&redlink=1" class="new" title="LRP5L (page does not exist)">LRP5L</a></li> <li><a href="/wiki/LRP6" title="LRP6">LRP6</a></li> <li><a href="/wiki/Low-density_lipoprotein_receptor-related_protein_8" title="Low-density lipoprotein receptor-related protein 8">LRP8</a></li> <li><a href="/wiki/LRP10" title="LRP10">LRP10</a></li> <li><a href="/wiki/LRP11" title="LRP11">LRP11</a></li> <li><a href="/w/index.php?title=LRP12&action=edit&redlink=1" class="new" title="LRP12 (page does not exist)">LRP12</a></li></ul></li> <li>LDL: <a href="/wiki/LDL_receptor" title="LDL receptor">LDLR</a></li> <li><a href="/wiki/LDL-receptor-related_protein-associated_protein" title="LDL-receptor-related protein-associated protein">LRPAP1</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/ATP-binding_cassette_transporter" class="mw-redirect" title="ATP-binding cassette transporter">ATP-binding <br />cassette transporter</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/ABCA1" title="ABCA1">ABCA1</a></li> <li><a href="/wiki/ABCG5" title="ABCG5">ABCG5</a></li> <li><a href="/wiki/ABCG8" title="ABCG8">ABCG8</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Lipids:_phospholipids" 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:Phospholipids" title="Template:Phospholipids"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Phospholipids" title="Template talk:Phospholipids"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Phospholipids" title="Special:EditPage/Template:Phospholipids"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Lipids:_phospholipids" style="font-size:114%;margin:0 4em"><a class="mw-selflink selflink">Lipids</a>: <a href="/wiki/Phospholipid" title="Phospholipid">phospholipids</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Glycerol" title="Glycerol">Glycerol</a> backbone<br />(<a href="/wiki/Glycerophospholipid" title="Glycerophospholipid">Glycerophospholipids/<br />Phosphoglycerides</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/Phosphatidic_acid" title="Phosphatidic acid">Phosphatidyl-</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/Phosphatidylethanolamine" title="Phosphatidylethanolamine">-ethanolamine/cephalin (PE)</a></li> <li><a href="/wiki/Phosphatidylcholine" title="Phosphatidylcholine">-choline/lecithin (PC)</a></li> <li><a href="/wiki/Phosphatidylserine" title="Phosphatidylserine">-serine (PS)</a></li> <li><a href="/wiki/Phosphatidylglycerol" title="Phosphatidylglycerol">-glycerol (PG)</a></li> <li><a href="/wiki/Phosphatidylinositol" title="Phosphatidylinositol">-inositol (PI)</a> <ul><li><a href="/wiki/Glycophosphatidylinositol" class="mw-redirect" title="Glycophosphatidylinositol">glyco-</a> (GPI)</li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Phosphoinositides:</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>PIP <ul><li><a href="/wiki/Phosphatidylinositol_3-phosphate" title="Phosphatidylinositol 3-phosphate">PI(3)P</a></li> <li><a href="/wiki/Phosphatidylinositol_4-phosphate" title="Phosphatidylinositol 4-phosphate">PI(4)P</a></li> <li><a href="/wiki/Phosphatidylinositol_5-phosphate" title="Phosphatidylinositol 5-phosphate">PI(5)P</a></li></ul></li> <li>PIP<sub>2</sub> <ul><li><a href="/wiki/Phosphatidylinositol_3,4-bisphosphate" title="Phosphatidylinositol 3,4-bisphosphate">PI(3,4)P<sub>2</sub></a></li> <li><a href="/wiki/Phosphatidylinositol_3,5-bisphosphate" title="Phosphatidylinositol 3,5-bisphosphate">PI(3,5)P<sub>2</sub></a></li> <li><a href="/wiki/Phosphatidylinositol_4,5-bisphosphate" title="Phosphatidylinositol 4,5-bisphosphate">PI(4,5)P<sub>2</sub></a></li></ul></li> <li><a href="/wiki/Phosphatidylinositol_(3,4,5)-trisphosphate" title="Phosphatidylinositol (3,4,5)-trisphosphate">PIP<sub>3</sub></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Ether_lipid" title="Ether lipid">Ether lipids</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/Plasmalogen" title="Plasmalogen">Plasmalogen</a> <ul><li><a href="/wiki/Platelet-activating_factor" title="Platelet-activating factor">Platelet-activating factor</a></li></ul></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cardiolipin" title="Cardiolipin">Cardiolipin</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sphingosine" title="Sphingosine">Sphingosine</a> backbone</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Sphingomyelin" title="Sphingomyelin">Sphingomyelin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Metabolites</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-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Inositol_phosphate" title="Inositol phosphate">Inositol phosphate</a></li> <li><a href="/wiki/Inositol" title="Inositol">Inositol</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Lysophosphatidic_acid" title="Lysophosphatidic acid">Lysophosphatidic acid</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Choline" title="Choline">Choline</a></li> <li><a href="/wiki/Phosphocholine" title="Phosphocholine">Phosphocholine</a></li> <li><a href="/wiki/Citicoline" title="Citicoline">Citicoline</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="Glycoconjugates,_lipids,_and_glycolipids:_sphingolipids_and_glycosphingolipids,_and_metabolic_intermediates" 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:Sphingolipids" title="Template:Sphingolipids"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Sphingolipids" title="Template talk:Sphingolipids"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Sphingolipids" title="Special:EditPage/Template:Sphingolipids"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Glycoconjugates,_lipids,_and_glycolipids:_sphingolipids_and_glycosphingolipids,_and_metabolic_intermediates" style="font-size:114%;margin:0 4em"><a href="/wiki/Glycoconjugate" title="Glycoconjugate">Glycoconjugates</a>, <a class="mw-selflink selflink">lipids</a>, and <a href="/wiki/Glycolipid" title="Glycolipid">glycolipids</a>: <a href="/wiki/Sphingolipid" title="Sphingolipid">sphingolipids</a> and <a href="/wiki/Glycosphingolipid" title="Glycosphingolipid">glycosphingolipids</a>, and <a href="/wiki/Metabolic_intermediate" title="Metabolic intermediate">metabolic intermediates</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Simple glycosphingolipids</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cerebroside" title="Cerebroside">Cerebroside</a> <ul><li><a href="/wiki/Galactocerebroside" class="mw-redirect" title="Galactocerebroside">Galactocerebroside</a></li> <li><a href="/wiki/Glucocerebroside" title="Glucocerebroside">Glucocerebroside</a></li></ul></li> <li><a href="/wiki/Sulfatide" title="Sulfatide">Sulfatide</a></li> <li><a href="/wiki/Lactosylceramide" title="Lactosylceramide">Lactosylceramide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Globosides" class="mw-redirect" title="Globosides">Globosides</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Globotriaosylceramide" title="Globotriaosylceramide">Globotriaosylceramide</a></li> <li><a href="/wiki/Stage-specific_embryonic_antigen_3" title="Stage-specific embryonic antigen 3">Stage-specific embryonic antigen 3</a></li> <li><a href="/wiki/Globo_H" title="Globo H">Globo H</a></li> <li><a href="/wiki/Forssman_antigen" title="Forssman antigen">Forssman antigen</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Gangliosides" class="mw-redirect" title="Gangliosides">Gangliosides</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/GM1" title="GM1">GM1</a></li> <li><a href="/wiki/GM2_(ganglioside)" title="GM2 (ganglioside)">GM2</a></li> <li><a href="/wiki/GM3" title="GM3">GM3</a></li> <li><a href="/wiki/GD2" title="GD2">GD2</a></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-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Sphingomyelin" title="Sphingomyelin">Sphingomyelin</a></li> <li><a href="/wiki/Sphingosine-1-phosphate" title="Sphingosine-1-phosphate">Sphingosine-1-phosphate</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Metabolism,_catabolism,_anabolism" 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"><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:Metabolism" title="Template:Metabolism"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Metabolism" title="Template talk:Metabolism"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Metabolism" title="Special:EditPage/Template:Metabolism"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Metabolism,_catabolism,_anabolism" style="font-size:114%;margin:0 4em"><a href="/wiki/Metabolism" title="Metabolism">Metabolism</a>, <a href="/wiki/Catabolism" title="Catabolism">catabolism</a>, <a href="/wiki/Anabolism" title="Anabolism">anabolism</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">General</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Metabolic_pathway" title="Metabolic pathway">Metabolic pathway</a></li> <li><a href="/wiki/Metabolic_network" title="Metabolic network">Metabolic network</a></li> <li><a href="/wiki/Primary_nutritional_groups" title="Primary nutritional groups">Primary nutritional groups</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Bioenergetics" title="Bioenergetics">Energy<br /> metabolism</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/Aerobic_respiration" class="mw-redirect" title="Aerobic respiration">Aerobic respiration</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/Glycolysis" title="Glycolysis">Glycolysis</a> → <a href="/wiki/Pyruvate_dehydrogenase" title="Pyruvate dehydrogenase">Pyruvate decarboxylation</a> → <a href="/wiki/Citric_acid_cycle" title="Citric acid cycle">Citric acid cycle</a> → <a href="/wiki/Oxidative_phosphorylation" title="Oxidative phosphorylation">Oxidative phosphorylation</a> (<span style="font-size:85%;"><a href="/wiki/Electron_transport_chain" title="Electron transport chain">electron transport chain</a> + <a href="/wiki/ATP_synthase" title="ATP synthase">ATP synthase</a></span>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Anaerobic_respiration" title="Anaerobic respiration">Anaerobic respiration</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>Electron acceptors other than oxygen</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Fermentation" title="Fermentation">Fermentation</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/Glycolysis" title="Glycolysis">Glycolysis</a> → <a href="/wiki/Substrate-level_phosphorylation" title="Substrate-level phosphorylation">Substrate-level phosphorylation</a> <ul><li><a href="/wiki/Acetone%E2%80%93butanol%E2%80%93ethanol_fermentation" title="Acetone–butanol–ethanol fermentation">ABE</a></li> <li><a href="/wiki/Ethanol_fermentation" title="Ethanol fermentation">Ethanol</a></li> <li><a href="/wiki/Lactic_acid_fermentation" title="Lactic acid fermentation">Lactic acid</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Specific<br /> paths</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/Protein_metabolism" title="Protein metabolism">Protein metabolism</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Protein_biosynthesis" title="Protein biosynthesis">Protein synthesis</a></li> <li><a href="/wiki/Protein_catabolism" title="Protein catabolism">Catabolism</a> (protein→peptide→amino acid)</li></ul> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Amino_acid" title="Amino acid">Amino acid</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/Amino_acid_synthesis" title="Amino acid synthesis">Amino acid synthesis</a></li> <li><a href="/wiki/Protein_catabolism#Amino_acid_degradation" title="Protein catabolism">Amino acid degradation</a> (amino acid→pyruvate, acetyl CoA, or TCA intermediate)</li> <li><a href="/wiki/Urea_cycle" title="Urea cycle">Urea cycle</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nucleic_acid_metabolism" title="Nucleic acid metabolism">Nucleotide<br /> metabolism</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/Purine_metabolism" title="Purine metabolism">Purine metabolism</a></li> <li><a href="/wiki/Nucleotide_salvage" title="Nucleotide salvage">Nucleotide salvage</a></li> <li><a href="/wiki/Pyrimidine_metabolism" title="Pyrimidine metabolism">Pyrimidine metabolism</a></li> <li><a href="/wiki/Purine_nucleotide_cycle" title="Purine nucleotide cycle">Purine nucleotide cycle</a></li></ul> </div></td></tr></tbody></table><div> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carbohydrate_metabolism" title="Carbohydrate metabolism">Carbohydrate metabolism</a><br />(<a href="/wiki/Carbohydrate_catabolism" title="Carbohydrate catabolism">carbohydrate catabolism</a><br />and <a href="/wiki/Anabolism" title="Anabolism">anabolism</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%">Human</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/Glycolysis" title="Glycolysis">Glycolysis</a> ⇄ <a href="/wiki/Gluconeogenesis" title="Gluconeogenesis">Gluconeogenesis</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Glycogenolysis" title="Glycogenolysis">Glycogenolysis</a> ⇄ <a href="/wiki/Glycogenesis" title="Glycogenesis">Glycogenesis</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Pentose_phosphate_pathway" title="Pentose phosphate pathway">Pentose phosphate pathway</a></li> <li><a href="/wiki/Fructolysis" title="Fructolysis">Fructolysis</a> <ul><li><a href="/wiki/Polyol_pathway" title="Polyol pathway">Polyol pathway</a></li></ul></li> <li><a href="/wiki/Galactolysis" title="Galactolysis">Galactolysis</a> <ul><li><a href="/wiki/Leloir_pathway" title="Leloir pathway">Leloir pathway</a></li></ul></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Glycosylation" title="Glycosylation">Glycosylation</a> <ul><li><a href="/wiki/N-linked_glycosylation" title="N-linked glycosylation">N-linked</a></li> <li><a href="/wiki/O-linked_glycosylation" title="O-linked glycosylation">O-linked</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Nonhuman</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/Photosynthesis" title="Photosynthesis">Photosynthesis</a></li> <li><a href="/wiki/Anoxygenic_photosynthesis" title="Anoxygenic photosynthesis">Anoxygenic photosynthesis</a></li> <li><a href="/wiki/Chemosynthesis" title="Chemosynthesis">Chemosynthesis</a></li> <li><a href="/wiki/Carbon_fixation" class="mw-redirect" title="Carbon fixation">Carbon fixation</a></li> <li><a href="/w/index.php?title=DeLey-Doudoroff_pathway&action=edit&redlink=1" class="new" title="DeLey-Doudoroff pathway (page does not exist)">DeLey-Doudoroff pathway</a></li> <li><a href="/wiki/Entner-Doudoroff_pathway" class="mw-redirect" title="Entner-Doudoroff pathway">Entner-Doudoroff pathway</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Xylose_metabolism" title="Xylose metabolism">Xylose metabolism</a></li> <li><a href="/wiki/Radiotrophic_fungus" title="Radiotrophic fungus">Radiotrophism</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/Lipid_metabolism" title="Lipid metabolism">Lipid metabolism</a> <br />(<a href="/wiki/Lipolysis" title="Lipolysis">lipolysis</a>, <a href="/wiki/Lipogenesis" title="Lipogenesis">lipogenesis</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/Fatty_acid_metabolism" title="Fatty acid metabolism">Fatty acid metabolism</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/Fatty_acid_degradation" title="Fatty acid degradation">Fatty acid degradation</a> (<a href="/wiki/Beta_oxidation" title="Beta oxidation">Beta oxidation</a>)</li> <li><a href="/wiki/Fatty_acid_synthesis" title="Fatty acid synthesis">Fatty acid synthesis</a></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><a href="/wiki/Steroid" title="Steroid">Steroid metabolism</a></li> <li><a href="/wiki/Sphingolipid_metabolism" class="mw-redirect" title="Sphingolipid metabolism">Sphingolipid metabolism</a></li> <li><a href="/wiki/Eicosanoid_metabolism" class="mw-redirect" title="Eicosanoid metabolism">Eicosanoid metabolism</a></li> <li><a href="/wiki/Ketosis" title="Ketosis">Ketosis</a></li> <li><a href="/wiki/Reverse_cholesterol_transport" title="Reverse cholesterol transport">Reverse cholesterol transport</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</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/Bioinorganic_chemistry" title="Bioinorganic chemistry">Metal metabolism</a> <ul><li><a href="/wiki/Human_iron_metabolism" title="Human iron metabolism">Iron metabolism</a></li></ul></li> <li><a href="/wiki/Ethanol_metabolism" class="mw-redirect" title="Ethanol metabolism">Ethanol metabolism</a></li> <li><a href="/wiki/Phosphagen" title="Phosphagen">Phospagen system (ATP-PCr)</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="Food_chemistry" 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:Food_chemistry" title="Template:Food chemistry"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Food_chemistry" title="Template talk:Food chemistry"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Food_chemistry" title="Special:EditPage/Template:Food chemistry"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Food_chemistry" style="font-size:114%;margin:0 4em"><a href="/wiki/Food_chemistry" title="Food chemistry">Food chemistry</a></div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Food_additive" title="Food additive">Additives</a></li> <li><a href="/wiki/Carbohydrate" title="Carbohydrate">Carbohydrates</a></li> <li><a href="/wiki/Food_coloring" title="Food coloring">Coloring</a></li> <li><a href="/wiki/Enzyme" title="Enzyme">Enzymes</a></li> <li><a href="/wiki/Essential_fatty_acid" title="Essential fatty acid">Essential fatty acids</a></li> <li><a href="/wiki/Flavoring" title="Flavoring">Flavors</a></li> <li><a href="/wiki/Food_fortification" title="Food fortification">Fortification</a></li> <li><a class="mw-selflink selflink">Lipids</a></li> <li><a href="/wiki/Mineral_(nutrient)" title="Mineral (nutrient)">"Minerals" (Chemical elements)</a></li> <li><a href="/wiki/Protein" title="Protein">Proteins</a></li> <li><a href="/wiki/Vitamin" title="Vitamin">Vitamins</a></li> <li><a href="/wiki/Water" title="Water">Water</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"></div><div role="navigation" class="navbox authority-control" aria-label="Navbox" style="padding:3px"><table class="nowraplinks hlist navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Help:Authority_control" title="Help:Authority control">Authority control databases</a>: National <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q11367#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></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="https://d-nb.info/gnd/4035873-2">Germany</a></span></li><li><span class="uid"><a rel="nofollow" class="external text" href="https://id.loc.gov/authorities/sh85077296">United States</a></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="Lipides"><a rel="nofollow" class="external text" href="https://catalogue.bnf.fr/ark:/12148/cb11965343d">France</a></span></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="Lipides"><a rel="nofollow" class="external text" href="https://data.bnf.fr/ark:/12148/cb11965343d">BnF data</a></span></span></li><li><span class="uid"><a rel="nofollow" class="external text" href="https://id.ndl.go.jp/auth/ndlna/00571254">Japan</a></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="lipidy"><a rel="nofollow" class="external text" href="https://aleph.nkp.cz/F/?func=find-c&local_base=aut&ccl_term=ica=ph122358&CON_LNG=ENG">Czech Republic</a></span></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="Lípidos"><a rel="nofollow" class="external text" href="http://catalogo.bne.es/uhtbin/authoritybrowse.cgi?action=display&authority_id=XX529935">Spain</a></span></span></li><li><span class="uid"><a rel="nofollow" class="external text" href="http://olduli.nli.org.il/F/?func=find-b&local_base=NLX10&find_code=UID&request=987007531509805171">Israel</a></span></li></ul></div></td></tr></tbody></table></div> <style data-mw-deduplicate="TemplateStyles:r1130092004">.mw-parser-output .portal-bar{font-size:88%;font-weight:bold;display:flex;justify-content:center;align-items:baseline}.mw-parser-output .portal-bar-bordered{padding:0 2em;background-color:#fdfdfd;border:1px solid #a2a9b1;clear:both;margin:1em auto 0}.mw-parser-output .portal-bar-related{font-size:100%;justify-content:flex-start}.mw-parser-output .portal-bar-unbordered{padding:0 1.7em;margin-left:0}.mw-parser-output .portal-bar-header{margin:0 1em 0 0.5em;flex:0 0 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