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<span class="vector-toc-numb">2</span> <span>Main phospholipids</span> </div> </a> <button aria-controls="toc-Main_phospholipids-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 Main phospholipids subsection</span> </button> <ul id="toc-Main_phospholipids-sublist" class="vector-toc-list"> <li id="toc-Diacylglyceride_structures" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Diacylglyceride_structures"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>Diacylglyceride structures</span> </div> </a> <ul id="toc-Diacylglyceride_structures-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Phosphosphingolipids" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Phosphosphingolipids"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.2</span> <span>Phosphosphingolipids</span> </div> </a> <ul id="toc-Phosphosphingolipids-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Applications" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Applications"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Applications</span> </div> </a> <ul id="toc-Applications-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Simulations" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Simulations"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Simulations</span> </div> </a> <ul id="toc-Simulations-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Characterization" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Characterization"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Characterization</span> </div> </a> <button aria-controls="toc-Characterization-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 Characterization subsection</span> </button> <ul id="toc-Characterization-sublist" class="vector-toc-list"> <li id="toc-Analysis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Analysis"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Analysis</span> </div> </a> <ul id="toc-Analysis-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Phospholipid_synthesis" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Phospholipid_synthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Phospholipid synthesis</span> </div> </a> <ul id="toc-Phospholipid_synthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Sources" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Sources"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Sources</span> </div> </a> <ul id="toc-Sources-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-In_signal_transduction" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#In_signal_transduction"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>In signal transduction</span> </div> </a> <ul id="toc-In_signal_transduction-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Food_technology" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Food_technology"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>Food technology</span> </div> </a> <ul id="toc-Food_technology-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Phospholipid_derivatives" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Phospholipid_derivatives"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>Phospholipid derivatives</span> </div> </a> <ul id="toc-Phospholipid_derivatives-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Abbreviations_used_and_chemical_information_of_glycerophospholipids" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Abbreviations_used_and_chemical_information_of_glycerophospholipids"> <div class="vector-toc-text"> <span class="vector-toc-numb">11</span> <span>Abbreviations used and chemical information of glycerophospholipids</span> </div> </a> <ul id="toc-Abbreviations_used_and_chemical_information_of_glycerophospholipids-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">12</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">13</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Phospholipid</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 61 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-61" 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">61 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%AF%D9%87%D9%86_%D9%81%D8%B3%D9%81%D9%88%D8%B1%D9%8A" title="دهن فسفوري – Arabic" lang="ar" hreflang="ar" data-title="دهن فسفوري" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%AB%E0%A6%B8%E0%A6%AB%E0%A7%8B%E0%A6%B2%E0%A6%BF%E0%A6%AA%E0%A6%BF%E0%A6%A1" title="ফসফোলিপিড – Bangla" lang="bn" hreflang="bn" data-title="ফসফোলিপিড" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%A4%D0%BE%D1%81%D1%84%D0%BE%D0%BB%D0%B8%D0%BF%D0%B8%D0%B4" title="Фосфолипид – Bulgarian" lang="bg" hreflang="bg" data-title="Фосфолипид" 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/Fosfolipid" title="Fosfolipid – Bosnian" lang="bs" hreflang="bs" data-title="Fosfolipid" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Fosfol%C3%ADpid" title="Fosfolípid – Catalan" lang="ca" hreflang="ca" data-title="Fosfolípid" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Fosfolipid" title="Fosfolipid – Czech" lang="cs" hreflang="cs" data-title="Fosfolipid" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Fosfolipid" title="Fosfolipid – Danish" lang="da" hreflang="da" data-title="Fosfolipid" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Phospholipide" title="Phospholipide – German" lang="de" hreflang="de" data-title="Phospholipide" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Fosfolipiidid" title="Fosfolipiidid – Estonian" lang="et" hreflang="et" data-title="Fosfolipiidid" 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%A6%CF%89%CF%83%CF%86%CE%BF%CE%BB%CE%B9%CF%80%CE%AF%CE%B4%CE%B9%CE%B1" title="Φωσφολιπίδια – Greek" lang="el" hreflang="el" data-title="Φωσφολιπίδια" 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/Fosfol%C3%ADpido" title="Fosfolípido – Spanish" lang="es" hreflang="es" data-title="Fosfolípido" 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/Fosfolipido" title="Fosfolipido – Esperanto" lang="eo" hreflang="eo" data-title="Fosfolipido" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Fosfolipido" title="Fosfolipido – Basque" lang="eu" hreflang="eu" data-title="Fosfolipido" 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%81%D8%B3%D9%81%D9%88%D9%84%DB%8C%D9%BE%DB%8C%D8%AF" title="فسفولیپید – Persian" lang="fa" hreflang="fa" data-title="فسفولیپید" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Phospholipide" title="Phospholipide – French" lang="fr" hreflang="fr" data-title="Phospholipide" 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/Fosfailipid" title="Fosfailipid – Irish" lang="ga" hreflang="ga" data-title="Fosfailipid" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Fosfol%C3%ADpido" title="Fosfolípido – Galician" lang="gl" hreflang="gl" data-title="Fosfolípido" 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%9D%B8%EC%A7%80%EC%A7%88" title="인지질 – Korean" lang="ko" hreflang="ko" data-title="인지질" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D5%96%D5%B8%D5%BD%D6%86%D5%B8%D5%AC%D5%AB%D5%BA%D5%AB%D5%A4" title="Ֆոսֆոլիպիդ – Armenian" lang="hy" hreflang="hy" data-title="Ֆոսֆոլիպիդ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Fosfolipidi" title="Fosfolipidi – Croatian" lang="hr" hreflang="hr" data-title="Fosfolipidi" 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/Fosfolipid" title="Fosfolipid – Indonesian" lang="id" hreflang="id" data-title="Fosfolipid" 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-is mw-list-item"><a href="https://is.wikipedia.org/wiki/Fosf%C3%B3l%C3%ADp%C3%AD%C3%B0" title="Fosfólípíð – Icelandic" lang="is" hreflang="is" data-title="Fosfólípíð" 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/Fosfolipide" title="Fosfolipide – Italian" lang="it" hreflang="it" data-title="Fosfolipide" 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%A4%D7%95%D7%A1%D7%A4%D7%95%D7%9C%D7%99%D7%A4%D7%99%D7%93" title="פוספוליפיד – Hebrew" lang="he" hreflang="he" data-title="פוספוליפיד" 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/Fosfolipid" title="Fosfolipid – Javanese" lang="jv" hreflang="jv" data-title="Fosfolipid" data-language-autonym="Jawa" data-language-local-name="Javanese" class="interlanguage-link-target"><span>Jawa</span></a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%A4%E1%83%9D%E1%83%A1%E1%83%A4%E1%83%9D%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="ფოსფოლიპიდები – Georgian" lang="ka" hreflang="ka" data-title="ფოსფოლიპიდები" 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%A4%D0%BE%D1%81%D1%84%D0%BE%D0%BB%D0%B8%D0%BF%D0%B8%D0%B4%D1%82%D0%B5%D1%80" title="Фосфолипидтер – Kazakh" lang="kk" hreflang="kk" data-title="Фосфолипидтер" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Phospholipidum" title="Phospholipidum – Latin" lang="la" hreflang="la" data-title="Phospholipidum" 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/Fosfolip%C4%ABdi" title="Fosfolipīdi – Latvian" lang="lv" hreflang="lv" data-title="Fosfolipīdi" 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/Phospholipid" title="Phospholipid – Luxembourgish" lang="lb" hreflang="lb" data-title="Phospholipid" 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/Fosfolipidai" title="Fosfolipidai – Lithuanian" lang="lt" hreflang="lt" data-title="Fosfolipidai" 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/Fosfolipid" title="Fosfolipid – Lombard" lang="lmo" hreflang="lmo" data-title="Fosfolipid" 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/Foszfolipidek" title="Foszfolipidek – Hungarian" lang="hu" hreflang="hu" data-title="Foszfolipidek" 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%A4%D0%BE%D1%81%D1%84%D0%BE%D0%BB%D0%B8%D0%BF%D0%B8%D0%B4" title="Фосфолипид – Macedonian" lang="mk" hreflang="mk" data-title="Фосфолипид" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Fosfolipid" title="Fosfolipid – Malay" lang="ms" hreflang="ms" data-title="Fosfolipid" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Fosfolipide" title="Fosfolipide – Dutch" lang="nl" hreflang="nl" data-title="Fosfolipide" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%AA%E3%83%B3%E8%84%82%E8%B3%AA" title="リン脂質 – Japanese" lang="ja" hreflang="ja" data-title="リン脂質" 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/Fosfolipid" title="Fosfolipid – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Fosfolipid" 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/Fosfolipid" title="Fosfolipid – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Fosfolipid" 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-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Fosfolipidlar" title="Fosfolipidlar – Uzbek" lang="uz" hreflang="uz" data-title="Fosfolipidlar" 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-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Fosfolipidy" title="Fosfolipidy – Polish" lang="pl" hreflang="pl" data-title="Fosfolipidy" 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/Fosfol%C3%ADpido" title="Fosfolípido – Portuguese" lang="pt" hreflang="pt" data-title="Fosfolípido" 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/Fosfolipid%C4%83" title="Fosfolipidă – Romanian" lang="ro" hreflang="ro" data-title="Fosfolipidă" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%A4%D0%BE%D1%81%D1%84%D0%BE%D0%BB%D0%B8%D0%BF%D0%B8%D0%B4%D1%8B" title="Фосфолипиды – Russian" lang="ru" hreflang="ru" data-title="Фосфолипиды" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sq mw-list-item"><a href="https://sq.wikipedia.org/wiki/Fosfolipidet" title="Fosfolipidet – Albanian" lang="sq" hreflang="sq" data-title="Fosfolipidet" data-language-autonym="Shqip" data-language-local-name="Albanian" class="interlanguage-link-target"><span>Shqip</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Phospholipid" title="Phospholipid – Simple English" lang="en-simple" hreflang="en-simple" data-title="Phospholipid" 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/Fosfolipid" title="Fosfolipid – Slovak" lang="sk" hreflang="sk" data-title="Fosfolipid" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Fosfolipid" title="Fosfolipid – Slovenian" lang="sl" hreflang="sl" data-title="Fosfolipid" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-ckb mw-list-item"><a href="https://ckb.wikipedia.org/wiki/%DA%86%DB%95%D9%88%D8%B1%DB%8C%DB%8C_%D9%81%DB%86%D8%B3%D9%81%DB%86%D8%B1%DB%8C" title="چەوریی فۆسفۆری – Central Kurdish" lang="ckb" hreflang="ckb" data-title="چەوریی فۆسفۆری" 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/Fosfolipid" title="Fosfolipid – Serbian" lang="sr" hreflang="sr" data-title="Fosfolipid" 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/Fosfolipid" title="Fosfolipid – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Fosfolipid" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Fosfolipidi" title="Fosfolipidi – Finnish" lang="fi" hreflang="fi" data-title="Fosfolipidi" 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/Fosfolipid" title="Fosfolipid – Swedish" lang="sv" hreflang="sv" data-title="Fosfolipid" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%AA%E0%AE%BE%E0%AE%B8%E0%AF%8D%E0%AE%AA%E0%AF%8B%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="பாஸ்போகொழுமியம் – Tamil" lang="ta" hreflang="ta" data-title="பாஸ்போகொழுமியம்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B8%9F%E0%B8%AD%E0%B8%AA%E0%B9%82%E0%B8%9F%E0%B8%A5%E0%B8%B4%E0%B8%9E%E0%B8%B4%E0%B8%94" title="ฟอสโฟลิพิด – Thai" lang="th" hreflang="th" data-title="ฟอสโฟลิพิด" 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/Fosfolipit" title="Fosfolipit – Turkish" lang="tr" hreflang="tr" data-title="Fosfolipit" 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%A4%D0%BE%D1%81%D1%84%D0%BE%D0%BB%D1%96%D0%BF%D1%96%D0%B4%D0%B8" title="Фосфоліпіди – Ukrainian" lang="uk" hreflang="uk" data-title="Фосфоліпіди" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Phospholipid" title="Phospholipid – Vietnamese" lang="vi" hreflang="vi" data-title="Phospholipid" 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-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E7%A3%B7%E8%84%82" title="磷脂 – Wu" lang="wuu" hreflang="wuu" data-title="磷脂" 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href="/wiki/File:Phospholipid_TvanBrussel.edit.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/48/Phospholipid_TvanBrussel.edit.jpg/220px-Phospholipid_TvanBrussel.edit.jpg" decoding="async" width="220" height="157" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/48/Phospholipid_TvanBrussel.edit.jpg/330px-Phospholipid_TvanBrussel.edit.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/48/Phospholipid_TvanBrussel.edit.jpg/440px-Phospholipid_TvanBrussel.edit.jpg 2x" data-file-width="614" data-file-height="437" /></a><figcaption>Phospholipid arrangement in cell membranes.</figcaption></figure> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Phosphatidyl-Choline.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1a/Phosphatidyl-Choline.svg/220px-Phosphatidyl-Choline.svg.png" decoding="async" width="220" height="86" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1a/Phosphatidyl-Choline.svg/330px-Phosphatidyl-Choline.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1a/Phosphatidyl-Choline.svg/440px-Phosphatidyl-Choline.svg.png 2x" data-file-width="391" data-file-height="152" /></a><figcaption><a href="/wiki/Phosphatidylcholine" title="Phosphatidylcholine">Phosphatidylcholine</a> is the major component of <a href="/wiki/Lecithin" title="Lecithin">lecithin</a>. It is also a source for <a href="/wiki/Choline" title="Choline">choline</a> in the synthesis of acetylcholine in cholinergic neurons.</figcaption></figure> <p><b>Phospholipids</b><sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> are a class of <a href="/wiki/Lipid" title="Lipid">lipids</a> whose molecule has a <a href="/wiki/Hydrophile" title="Hydrophile">hydrophilic</a> "head" containing a <a href="/wiki/Phosphate" title="Phosphate">phosphate</a> group and two <a href="/wiki/Hydrophobic" class="mw-redirect" title="Hydrophobic">hydrophobic</a> "tails" derived from <a href="/wiki/Fatty_acid" title="Fatty acid">fatty acids</a>, joined by an <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohol</a> residue (usually a <a href="/wiki/Glycerol" title="Glycerol">glycerol</a> molecule). Marine phospholipids typically have <a href="/wiki/Omega-3_fatty_acid" title="Omega-3 fatty acid">omega-3 fatty acids</a> <a href="/wiki/Eicosapentaenoic_acid" title="Eicosapentaenoic acid">EPA</a> and <a href="/wiki/Docosahexaenoic_acid" title="Docosahexaenoic acid">DHA</a> integrated as part of the phospholipid molecule.<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> The phosphate group can be modified with simple organic molecules such as <a href="/wiki/Choline" title="Choline">choline</a>, <a href="/wiki/Ethanolamine" title="Ethanolamine">ethanolamine</a> or <a href="/wiki/Serine" title="Serine">serine</a>.<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. (October 2023)">citation needed</span></a></i>]</sup> </p><p>Phospholipids are a key component of all <a href="/wiki/Cell_membrane" title="Cell membrane">cell membranes</a>. They can form <a href="/wiki/Lipid_bilayer" title="Lipid bilayer">lipid bilayers</a> because of their <a href="/wiki/Amphiphilic" class="mw-redirect" title="Amphiphilic">amphiphilic</a> characteristic. In <a href="/wiki/Eukaryote" title="Eukaryote">eukaryotes</a>, cell membranes also contain another class of lipid, <a href="/wiki/Sterol" title="Sterol">sterol</a>, interspersed among the phospholipids. The combination provides fluidity in two dimensions combined with mechanical strength against rupture. Purified phospholipids are produced commercially and have found applications in <a href="/wiki/Nanotechnology" title="Nanotechnology">nanotechnology</a> and <a href="/wiki/Materials_science" title="Materials science">materials science</a>.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>The first phospholipid identified in 1847 as such in biological tissues was <a href="/wiki/Lecithin" title="Lecithin">lecithin</a>, or <a href="/wiki/Phosphatidylcholine" title="Phosphatidylcholine">phosphatidylcholine</a>, in the egg yolk of chickens by the French chemist and pharmacist <a href="/wiki/Theodore_Nicolas_Gobley" class="mw-redirect" title="Theodore Nicolas Gobley">Theodore Nicolas Gobley</a>. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Phospholipids_in_biological_membranes">Phospholipids in biological membranes</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phospholipid&action=edit&section=1" title="Edit section: Phospholipids in biological membranes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Arrangement">Arrangement</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phospholipid&action=edit&section=2" title="Edit section: Arrangement"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The phospholipids are <a href="/wiki/Amphiphilic" class="mw-redirect" title="Amphiphilic">amphiphilic</a>. The hydrophilic end usually contains a negatively charged phosphate group, and the hydrophobic end usually consists of two "tails" that are long <a href="/wiki/Fatty_acid" title="Fatty acid">fatty acid</a> residues.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><p>In aqueous solutions, phospholipids are driven by <a href="/wiki/Hydrophobic_interactions" class="mw-redirect" title="Hydrophobic interactions">hydrophobic interactions</a>, which result in the fatty acid tails aggregating to minimize interactions with the water molecules. The result is often a <a href="/wiki/Phospholipid_bilayer" class="mw-redirect" title="Phospholipid bilayer">phospholipid bilayer</a>: a membrane that consists of two layers of oppositely oriented phospholipid molecules, with their heads exposed to the liquid on both sides, and with the tails directed into the membrane. That is the dominant structural motif of the membranes of all <a href="/wiki/Cell_(biology)" title="Cell (biology)">cells</a> and of some other biological structures, such as <a href="/wiki/Vesicle_(biology)" class="mw-redirect" title="Vesicle (biology)">vesicles</a> or <a href="/wiki/Virus" title="Virus">virus</a> coatings.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Cell_membrane_detailed_diagram_4.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3a/Cell_membrane_detailed_diagram_4.svg/185px-Cell_membrane_detailed_diagram_4.svg.png" decoding="async" width="185" height="217" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3a/Cell_membrane_detailed_diagram_4.svg/278px-Cell_membrane_detailed_diagram_4.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3a/Cell_membrane_detailed_diagram_4.svg/370px-Cell_membrane_detailed_diagram_4.svg.png 2x" data-file-width="1690" data-file-height="1982" /></a><figcaption>Phospholipid bilayers are the main structural component of the cell membranes.</figcaption></figure> <p>In biological membranes, the phospholipids often occur with other molecules (e.g., <a href="/wiki/Protein" title="Protein">proteins</a>, <a href="/wiki/Glycolipid" title="Glycolipid">glycolipids</a>, <a href="/wiki/Sterol" title="Sterol">sterols</a>) in a <a href="/wiki/Bilayer" title="Bilayer">bilayer</a> such as a <a href="/wiki/Cell_membrane" title="Cell membrane">cell membrane</a>.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Lipid bilayers occur when hydrophobic tails line up against one another, forming a membrane of hydrophilic heads on both sides facing the water.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Dynamics">Dynamics</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phospholipid&action=edit&section=3" title="Edit section: Dynamics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>These specific properties allow phospholipids to play an important role in the cell membrane. Their movement can be described by the <a href="/wiki/Fluid_mosaic_model" title="Fluid mosaic model">fluid mosaic model</a>, which describes the membrane as a mosaic of lipid molecules that act as a solvent for all the substances and proteins within it, so proteins and lipid molecules are then free to diffuse laterally through the lipid matrix and migrate over the membrane. <a href="/wiki/Sterol" title="Sterol">Sterols</a> contribute to membrane fluidity by hindering the packing together of phospholipids. However, this model has now been superseded, as through the study of <a href="/wiki/Lipid_polymorphism" title="Lipid polymorphism">lipid polymorphism</a> it is now known that the behaviour of lipids under physiological (and other) conditions is not simple.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (December 2014)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading2"><h2 id="Main_phospholipids">Main phospholipids</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phospholipid&action=edit&section=4" title="Edit section: Main phospholipids"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Diacylglyceride_structures">Diacylglyceride structures</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phospholipid&action=edit&section=5" title="Edit section: Diacylglyceride structures"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <dl><dd><i>See: <a href="/wiki/Glycerophospholipid" title="Glycerophospholipid">Glycerophospholipid</a></i></dd></dl> <ul><li><a href="/wiki/Phosphatidic_acid" title="Phosphatidic acid">Phosphatidic acid</a> (phosphatidate) (PA)</li> <li><a href="/wiki/Phosphatidylethanolamine" title="Phosphatidylethanolamine">Phosphatidylethanolamine</a> (cephalin) (PE)</li> <li><a href="/wiki/Phosphatidylcholine" title="Phosphatidylcholine">Phosphatidylcholine</a> (lecithin) (PC)</li> <li><a href="/wiki/Phosphatidylserine" title="Phosphatidylserine">Phosphatidylserine</a> (PS)</li> <li>Phosphoinositides: <ul><li><a href="/wiki/Phosphatidylinositol" title="Phosphatidylinositol">Phosphatidylinositol</a> (PI)</li> <li><a href="/wiki/Phosphatidylinositol_phosphate_(disambiguation)" class="mw-redirect mw-disambig" title="Phosphatidylinositol phosphate (disambiguation)">Phosphatidylinositol phosphate</a> (PIP)</li> <li><a href="/wiki/Phosphatidylinositol_(4,5)-bisphosphate" class="mw-redirect" title="Phosphatidylinositol (4,5)-bisphosphate">Phosphatidylinositol bisphosphate</a> (PIP2) and</li> <li><a href="/wiki/Phosphatidylinositol_(3,4,5)-trisphosphate" title="Phosphatidylinositol (3,4,5)-trisphosphate">Phosphatidylinositol trisphosphate</a> (PIP3)</li></ul></li></ul> <div class="mw-heading mw-heading3"><h3 id="Phosphosphingolipids">Phosphosphingolipids</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phospholipid&action=edit&section=6" title="Edit section: Phosphosphingolipids"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <dl><dd><i>See <a href="/wiki/Sphingolipid" title="Sphingolipid">Sphingolipid</a></i></dd></dl> <ul><li>Ceramide phosphorylcholine (<a href="/wiki/Sphingomyelin" title="Sphingomyelin">Sphingomyelin</a>) (SPH)</li> <li>Ceramide phosphorylethanolamine (<a href="/wiki/Sphingomyelin" title="Sphingomyelin">Sphingomyelin</a>) (Cer-PE)</li> <li>Ceramide phosphoryllipid</li></ul> <div class="mw-heading mw-heading2"><h2 id="Applications">Applications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phospholipid&action=edit&section=7" title="Edit section: Applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Phospholipids have been widely used to prepare liposomal, ethosomal and other nanoformulations of topical, oral and <a href="/wiki/Route_of_administration#Parenteral" title="Route of administration">parenteral</a> drugs for differing reasons like improved bio-availability, reduced toxicity and increased permeability across membranes. Liposomes<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> are often composed of <a href="/wiki/Phosphatidylcholine" title="Phosphatidylcholine">phosphatidylcholine</a>-enriched phospholipids and may also contain mixed phospholipid chains with <a href="/wiki/Surfactant" title="Surfactant">surfactant</a> properties. The ethosomal formulation of <a href="/wiki/Ketoconazole" title="Ketoconazole">ketoconazole</a> using phospholipids is a promising option for transdermal delivery in fungal infections.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> Advances in phospholipid research lead to exploring these biomolecules and their conformations using lipidomics<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>.<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. (September 2022)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading2"><h2 id="Simulations">Simulations</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phospholipid&action=edit&section=8" title="Edit section: Simulations"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Computational simulations of phospholipids are often performed using <a href="/wiki/Molecular_dynamics" title="Molecular dynamics">molecular dynamics</a> with <a href="/wiki/Force_field_(chemistry)" title="Force field (chemistry)">force fields</a> such as <a href="/wiki/GROMOS" title="GROMOS">GROMOS</a>, <a href="/wiki/CHARMM" title="CHARMM">CHARMM</a>, or <a href="/wiki/AMBER" title="AMBER">AMBER</a>.<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. (October 2023)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading2"><h2 id="Characterization">Characterization</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phospholipid&action=edit&section=9" title="Edit section: Characterization"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Phospholipids are optically highly <a href="/wiki/Birefringent" class="mw-redirect" title="Birefringent">birefringent</a>, i.e. their refractive index is different along their axis as opposed to perpendicular to it. Measurement of <a href="/wiki/Birefringence" title="Birefringence">birefringence</a> can be achieved using cross polarisers in a microscope to obtain an image of e.g. <a href="/wiki/Vesicle_(biology)" class="mw-redirect" title="Vesicle (biology)">vesicle</a> walls or using techniques such as <a href="/wiki/Dual_polarisation_interferometry" class="mw-redirect" title="Dual polarisation interferometry">dual polarisation interferometry</a> to quantify lipid order or disruption in supported bilayers.<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. (September 2022)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading3"><h3 id="Analysis">Analysis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phospholipid&action=edit&section=10" title="Edit section: Analysis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>There are no simple methods available for analysis of phospholipids, since the close range of polarity between different phospholipid species makes detection difficult. Oil chemists often use spectroscopy to determine total phosphorus abundance and then calculate approximate mass of phospholipids based on molecular weight of expected fatty acid species. Modern lipid profiling employs more absolute methods of analysis, with <a href="/wiki/NMR_spectroscopy" class="mw-redirect" title="NMR spectroscopy">NMR spectroscopy</a>, particularly <a href="/wiki/Phosphorus-31_nuclear_magnetic_resonance" title="Phosphorus-31 nuclear magnetic resonance"><sup>31</sup>P-NMR</a>,<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> while <a href="/wiki/High-performance_liquid_chromatography" title="High-performance liquid chromatography">HPLC</a>-<a href="/wiki/Evaporative_light_scattering_detector" title="Evaporative light scattering detector">ELSD</a><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> provides relative values. </p> <div class="mw-heading mw-heading2"><h2 id="Phospholipid_synthesis">Phospholipid synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phospholipid&action=edit&section=11" title="Edit section: Phospholipid synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Biosynthesis#Phospholipids" title="Biosynthesis">Biosynthesis § Phospholipids</a></div> <p>Phospholipid synthesis occurs in the cytosolic side of <a href="/wiki/Endoplasmic_reticulum" title="Endoplasmic reticulum">ER</a> membrane <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> that is studded with proteins that act in synthesis (<a href="/wiki/Glycerol-3-phosphate_O-acyltransferase" title="Glycerol-3-phosphate O-acyltransferase">GPAT</a> and LPAAT acyl transferases, phosphatase and choline phosphotransferase) and allocation (<a href="/wiki/Flippase" title="Flippase">flippase</a> and floppase). Eventually a vesicle will bud off from the ER containing phospholipids destined for the cytoplasmic cellular membrane on its exterior leaflet and phospholipids destined for the exoplasmic cellular membrane on its inner leaflet.<sup id="cite_ref-Lodish_16-0" class="reference"><a href="#cite_note-Lodish-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid27956138_17-0" class="reference"><a href="#cite_note-pmid27956138-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Sources">Sources</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phospholipid&action=edit&section=12" title="Edit section: Sources"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Common sources of industrially produced phospholipids are soya, rapeseed, sunflower, chicken eggs, bovine milk, fish eggs etc. Phospholipids for gene delivery, such as <a href="/wiki/Distearoylphosphatidylcholine" title="Distearoylphosphatidylcholine">distearoylphosphatidylcholine</a> and <a href="/wiki/Dioleoyl-3-trimethylammonium_propane" title="Dioleoyl-3-trimethylammonium propane">dioleoyl-3-trimethylammonium propane</a>, are produced synthetically.<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. (July 2024)">citation needed</span></a></i>]</sup> Each source has a unique profile of individual phospholipid species, as well as fatty acids, and consequently differing applications in food, nutrition, pharmaceuticals, cosmetics, and drug delivery.<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. (September 2022)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading2"><h2 id="In_signal_transduction">In signal transduction</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phospholipid&action=edit&section=13" title="Edit section: In signal transduction"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Some types of phospholipid can be split to produce products that function as <a href="/wiki/Second_messengers" class="mw-redirect" title="Second messengers">second messengers</a> in <a href="/wiki/Signal_transduction" title="Signal transduction">signal transduction</a>. Examples include <a href="/wiki/Phosphatidylinositol_(4,5)-bisphosphate" class="mw-redirect" title="Phosphatidylinositol (4,5)-bisphosphate">phosphatidylinositol (4,5)-bisphosphate</a> (PIP<sub>2</sub>), that can be split by the enzyme <a href="/wiki/Phospholipase_C" title="Phospholipase C">phospholipase C</a> into <a href="/wiki/Inositol_triphosphate" class="mw-redirect" title="Inositol triphosphate">inositol triphosphate</a> (IP<sub>3</sub>) and <a href="/wiki/Diacylglycerol" class="mw-redirect" title="Diacylglycerol">diacylglycerol</a> (DAG), which both carry out the <a href="/wiki/Gq_alpha_subunit#Function" title="Gq alpha subunit">functions of the G<sub>q</sub> type of G protein</a> in response to various stimuli and intervene in various processes from <a href="/wiki/Long_term_depression" class="mw-redirect" title="Long term depression">long term depression</a> in neurons<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> to <a href="/wiki/Leukocyte" class="mw-redirect" title="Leukocyte">leukocyte</a> signal pathways started by <a href="/wiki/Chemokine" title="Chemokine">chemokine</a> receptors.<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> </p><p>Phospholipids also intervene in <a href="/wiki/Prostaglandin" title="Prostaglandin">prostaglandin</a> signal pathways as the raw material used by <a href="/wiki/Lipase" title="Lipase">lipase</a> enzymes to produce the prostaglandin precursors. In plants they serve as the raw material to produce <a href="/wiki/Jasmonic_acid" title="Jasmonic acid">jasmonic acid</a>, a <a href="/wiki/Plant_hormone" title="Plant hormone">plant hormone</a> similar in structure to prostaglandins that mediates defensive responses against pathogens.<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. (October 2023)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading2"><h2 id="Food_technology">Food technology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phospholipid&action=edit&section=14" title="Edit section: Food technology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Phospholipids can act as <a href="/wiki/Emulsion#Emulsifiers" title="Emulsion">emulsifiers</a>, enabling oils to form a <a href="/wiki/Colloid" title="Colloid">colloid</a> with water. Phospholipids are one of the components of <a href="/wiki/Lecithin" title="Lecithin">lecithin</a>, which is found in egg yolks, as well as being extracted from <a href="/wiki/Soybean" title="Soybean">soybeans</a>, and is used as a <a href="/wiki/Food_additive" title="Food additive">food additive</a> in many products and can be purchased as a <a href="/wiki/Dietary_supplement" title="Dietary supplement">dietary supplement</a>. Lysolecithins are typically used for water–oil emulsions like <a href="/wiki/Margarine" title="Margarine">margarine</a>, due to their higher <a href="/wiki/Hydrophilic-lipophilic_balance" title="Hydrophilic-lipophilic balance">HLB ratio</a>.<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. (October 2023)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading2"><h2 id="Phospholipid_derivatives">Phospholipid derivatives</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phospholipid&action=edit&section=15" title="Edit section: Phospholipid derivatives"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <dl><dd><i>See table below for an extensive list.</i></dd></dl> <ul><li>Natural phospholipid derivates: <dl><dd>egg PC (<a href="/wiki/Egg_lecithin" title="Egg lecithin">Egg lecithin</a>), egg PG, soy PC, hydrogenated soy PC, <a href="/wiki/Sphingomyelin" title="Sphingomyelin">sphingomyelin</a> as natural phospholipids.</dd></dl></li> <li>Synthetic phospholipid derivates: <ul><li><a href="/wiki/Phosphatidic_acid" title="Phosphatidic acid">Phosphatidic acid</a> (DMPA, DPPA, DSPA)</li> <li><a href="/wiki/Phosphatidylcholine" title="Phosphatidylcholine">Phosphatidylcholine</a> (DDPC, DLPC, DMPC, <a href="/wiki/Dipalmitoylphosphatidylcholine" title="Dipalmitoylphosphatidylcholine">DPPC</a>, DSPC, DOPC, <a href="/wiki/POPC" title="POPC">POPC</a>, DEPC)</li> <li><a href="/wiki/Phosphatidylglycerol" title="Phosphatidylglycerol">Phosphatidylglycerol</a> (DMPG, DPPG, DSPG, POPG)</li> <li><a href="/wiki/Phosphatidylethanolamine" title="Phosphatidylethanolamine">Phosphatidylethanolamine</a> (DMPE, DPPE, DSPE DOPE)</li> <li><a href="/wiki/Phosphatidylserine" title="Phosphatidylserine">Phosphatidylserine</a> (DOPS)</li> <li>PEG phospholipid (mPEG-phospholipid, polyglycerin-phospholipid, functionalized-phospholipid, terminal activated-phospholipid)</li></ul></li></ul> <div class="mw-heading mw-heading2"><h2 id="Abbreviations_used_and_chemical_information_of_glycerophospholipids">Abbreviations used and chemical information of glycerophospholipids</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phospholipid&action=edit&section=16" title="Edit section: Abbreviations used and chemical information of glycerophospholipids"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <table class="sortable wikitable"> <tbody><tr> <th>Abbreviation </th> <th>CAS </th> <th>Name </th> <th>Type </th></tr> <tr> <td>DDPC</td> <td>3436-44-0</td> <td>1,2-Didecanoyl-<i>sn</i>-glycero-3-phosphocholine</td> <td><a href="/wiki/Phosphatidylcholine" title="Phosphatidylcholine">Phosphatidylcholine</a> </td></tr> <tr> <td><a href="/w/index.php?title=DEPA-NA&action=edit&redlink=1" class="new" title="DEPA-NA (page does not exist)">DEPA-NA</a></td> <td>80724-31-8</td> <td>1,2-Dierucoyl-<i>sn</i>-glycero-3-phosphate (sodium salt)</td> <td><a href="/wiki/Phosphatidic_acid" title="Phosphatidic acid">Phosphatidic acid</a> </td></tr> <tr> <td><a href="/w/index.php?title=1,2-Erucoyl-sn-Glycero-3-phosphocholine&action=edit&redlink=1" class="new" title="1,2-Erucoyl-sn-Glycero-3-phosphocholine (page does not exist)">DEPC</a></td> <td>56649-39-9</td> <td>1,2-Dierucoyl-<i>sn</i>-glycero-3-phosphocholine</td> <td><a href="/wiki/Phosphatidylcholine" title="Phosphatidylcholine">Phosphatidylcholine</a> </td></tr> <tr> <td><a href="/w/index.php?title=DEPE&action=edit&redlink=1" class="new" title="DEPE (page does not exist)">DEPE</a></td> <td>988-07-2</td> <td>1,2-Dierucoyl-<i>sn</i>-glycero-3-phosphoethanolamine</td> <td><a href="/wiki/Phosphatidylethanolamine" title="Phosphatidylethanolamine">Phosphatidylethanolamine</a> </td></tr> <tr> <td><a href="/w/index.php?title=DEPG-NA&action=edit&redlink=1" class="new" title="DEPG-NA (page does not exist)">DEPG-NA</a></td> <td></td> <td>1,2-Dierucoyl-<i>sn</i>-glycero-3[phospho-rac-(1-glycerol...) (sodium salt)</td> <td><a href="/wiki/Phosphatidylglycerol" title="Phosphatidylglycerol">Phosphatidylglycerol</a> </td></tr> <tr> <td><a href="/w/index.php?title=DLOPC&action=edit&redlink=1" class="new" title="DLOPC (page does not exist)">DLOPC</a></td> <td>998-06-1</td> <td>1,2-Dilinoleoyl-<i>sn</i>-glycero-3-phosphocholine</td> <td><a href="/wiki/Phosphatidylcholine" title="Phosphatidylcholine">Phosphatidylcholine</a> </td></tr> <tr> <td><a href="/w/index.php?title=DLPA-NA&action=edit&redlink=1" class="new" title="DLPA-NA (page does not exist)">DLPA-NA</a></td> <td></td> <td>1,2-Dilauroyl-<i>sn</i>-glycero-3-phosphate (sodium salt)</td> <td><a href="/wiki/Phosphatidic_acid" title="Phosphatidic acid">Phosphatidic acid</a> </td></tr> <tr> <td>DLPC</td> <td>18194-25-7</td> <td>1,2-Dilauroyl-<i>sn</i>-glycero-3-phosphocholine</td> <td><a href="/wiki/Phosphatidylcholine" title="Phosphatidylcholine">Phosphatidylcholine</a> </td></tr> <tr> <td><a href="/w/index.php?title=DLPE&action=edit&redlink=1" class="new" title="DLPE (page does not exist)">DLPE</a></td> <td></td> <td>1,2-Dilauroyl-<i>sn</i>-glycero-3-phosphoethanolamine</td> <td><a href="/wiki/Phosphatidylethanolamine" title="Phosphatidylethanolamine">Phosphatidylethanolamine</a> </td></tr> <tr> <td><a href="/w/index.php?title=DLPG-NA&action=edit&redlink=1" class="new" title="DLPG-NA (page does not exist)">DLPG-NA</a></td> <td></td> <td>1,2-Dilauroyl-<i>sn</i>-glycero-3[phospho-rac-(1-glycerol...) (sodium salt)</td> <td><a href="/wiki/Phosphatidylglycerol" title="Phosphatidylglycerol">Phosphatidylglycerol</a> </td></tr> <tr> <td><a href="/w/index.php?title=DLPG-NH4&action=edit&redlink=1" class="new" title="DLPG-NH4 (page does not exist)">DLPG-NH4</a></td> <td></td> <td>1,2-Dilauroyl-<i>sn</i>-glycero-3[phospho-rac-(1-glycerol...) (ammonium salt)</td> <td><a href="/wiki/Phosphatidylglycerol" title="Phosphatidylglycerol">Phosphatidylglycerol</a> </td></tr> <tr> <td><a href="/w/index.php?title=DLPS-NA&action=edit&redlink=1" class="new" title="DLPS-NA (page does not exist)">DLPS-NA</a></td> <td></td> <td>1,2-Dilauroyl-<i>sn</i>-glycero-3-phosphoserine (sodium salt)</td> <td><a href="/wiki/Phosphatidylserine" title="Phosphatidylserine">Phosphatidylserine</a> </td></tr> <tr> <td><a href="/w/index.php?title=DMPA-NA&action=edit&redlink=1" class="new" title="DMPA-NA (page does not exist)">DMPA-NA</a></td> <td>80724-3</td> <td>1,2-Dimyristoyl-<i>sn</i>-glycero-3-phosphate (sodium salt)</td> <td><a href="/wiki/Phosphatidic_acid" title="Phosphatidic acid">Phosphatidic acid</a> </td></tr> <tr> <td><a href="/wiki/DMPC" class="mw-redirect" title="DMPC">DMPC</a></td> <td>18194-24-6</td> <td>1,2-Dimyristoyl-<i>sn</i>-glycero-3-phosphocholine</td> <td><a href="/wiki/Phosphatidylcholine" title="Phosphatidylcholine">Phosphatidylcholine</a> </td></tr> <tr> <td><a href="/wiki/Dimyristoylphosphatidylethanolamine" title="Dimyristoylphosphatidylethanolamine">DMPE</a></td> <td>988-07-2</td> <td>1,2-Dimyristoyl-<i>sn</i>-glycero-3-phosphoethanolamine</td> <td><a href="/wiki/Phosphatidylethanolamine" title="Phosphatidylethanolamine">Phosphatidylethanolamine</a> </td></tr> <tr> <td><a href="/w/index.php?title=DMPG-NA&action=edit&redlink=1" class="new" title="DMPG-NA (page does not exist)">DMPG-NA</a></td> <td>67232-80-8</td> <td>1,2-Dimyristoyl-<i>sn</i>-glycero-3[phospho-rac-(1-glycerol...) (sodium salt)</td> <td><a href="/wiki/Phosphatidylglycerol" title="Phosphatidylglycerol">Phosphatidylglycerol</a> </td></tr> <tr> <td><a href="/w/index.php?title=DMPG-NH4&action=edit&redlink=1" class="new" title="DMPG-NH4 (page does not exist)">DMPG-NH4</a></td> <td></td> <td>1,2-Dimyristoyl-<i>sn</i>-glycero-3[phospho-rac-(1-glycerol...) (ammonium salt)</td> <td><a href="/wiki/Phosphatidylglycerol" title="Phosphatidylglycerol">Phosphatidylglycerol</a> </td></tr> <tr> <td><a href="/w/index.php?title=DMPG-NH4/NA&action=edit&redlink=1" class="new" title="DMPG-NH4/NA (page does not exist)">DMPG-NH4/NA</a></td> <td></td> <td>1,2-Dimyristoyl-<i>sn</i>-glycero-3[phospho-rac-(1-glycerol...) (sodium/ammonium salt)</td> <td><a href="/wiki/Phosphatidylglycerol" title="Phosphatidylglycerol">Phosphatidylglycerol</a> </td></tr> <tr> <td><a href="/w/index.php?title=DMPS-NA&action=edit&redlink=1" class="new" title="DMPS-NA (page does not exist)">DMPS-NA</a></td> <td></td> <td>1,2-Dimyristoyl-<i>sn</i>-glycero-3-phosphoserine (sodium salt)</td> <td><a href="/wiki/Phosphatidylserine" title="Phosphatidylserine">Phosphatidylserine</a> </td></tr> <tr> <td><a href="/w/index.php?title=DOPA-NA&action=edit&redlink=1" class="new" title="DOPA-NA (page does not exist)">DOPA-NA</a></td> <td></td> <td>1,2-Dioleoyl-<i>sn</i>-glycero-3-phosphate (sodium salt)</td> <td><a href="/wiki/Phosphatidic_acid" title="Phosphatidic acid">Phosphatidic acid</a> </td></tr> <tr> <td><a href="/w/index.php?title=DOPC&action=edit&redlink=1" class="new" title="DOPC (page does not exist)">DOPC</a></td> <td>4235-95-4</td> <td>1,2-Dioleoyl-<i>sn</i>-glycero-3-phosphocholine</td> <td><a href="/wiki/Phosphatidylcholine" title="Phosphatidylcholine">Phosphatidylcholine</a> </td></tr> <tr> <td><a href="/w/index.php?title=DOPE_(lipid)&action=edit&redlink=1" class="new" title="DOPE (lipid) (page does not exist)">DOPE</a></td> <td>4004-5-1-</td> <td>1,2-Dioleoyl-<i>sn</i>-glycero-3-phosphoethanolamine</td> <td><a href="/wiki/Phosphatidylethanolamine" title="Phosphatidylethanolamine">Phosphatidylethanolamine</a> </td></tr> <tr> <td><a href="/w/index.php?title=DOPG-NA&action=edit&redlink=1" class="new" title="DOPG-NA (page does not exist)">DOPG-NA</a></td> <td>62700-69-0</td> <td>1,2-Dioleoyl-<i>sn</i>-glycero-3[phospho-rac-(1-glycerol...) (sodium salt)</td> <td><a href="/wiki/Phosphatidylglycerol" title="Phosphatidylglycerol">Phosphatidylglycerol</a> </td></tr> <tr> <td><a href="/w/index.php?title=DOPS-NA&action=edit&redlink=1" class="new" title="DOPS-NA (page does not exist)">DOPS-NA</a></td> <td>70614-14-1</td> <td>1,2-Dioleoyl-<i>sn</i>-glycero-3-phosphoserine (sodium salt)</td> <td><a href="/wiki/Phosphatidylserine" title="Phosphatidylserine">Phosphatidylserine</a> </td></tr> <tr> <td><a href="/w/index.php?title=DPPA-NA&action=edit&redlink=1" class="new" title="DPPA-NA (page does not exist)">DPPA-NA</a></td> <td>71065-87-7</td> <td>1,2-Dipalmitoyl-<i>sn</i>-glycero-3-phosphate (sodium salt)</td> <td><a href="/wiki/Phosphatidic_acid" title="Phosphatidic acid">Phosphatidic acid</a> </td></tr> <tr> <td><a href="/wiki/Dipalmitoylphosphatidylcholine" title="Dipalmitoylphosphatidylcholine">DPPC</a></td> <td>63-89-8</td> <td>1,2-Dipalmitoyl-<i>sn</i>-glycero-3-phosphocholine</td> <td><a href="/wiki/Phosphatidylcholine" title="Phosphatidylcholine">Phosphatidylcholine</a> </td></tr> <tr> <td><a href="/wiki/Dipalmitoylphosphatidylethanolamine" title="Dipalmitoylphosphatidylethanolamine">DPPE</a></td> <td>923-61-5</td> <td>1,2-Dipalmitoyl-<i>sn</i>-glycero-3-phosphoethanolamine</td> <td><a href="/wiki/Phosphatidylethanolamine" title="Phosphatidylethanolamine">Phosphatidylethanolamine</a> </td></tr> <tr> <td><a href="/w/index.php?title=DPPG-NA&action=edit&redlink=1" class="new" title="DPPG-NA (page does not exist)">DPPG-NA</a></td> <td>67232-81-9</td> <td>1,2-Dipalmitoyl-<i>sn</i>-glycero-3[phospho-rac-(1-glycerol...) (sodium salt)</td> <td><a href="/wiki/Phosphatidylglycerol" title="Phosphatidylglycerol">Phosphatidylglycerol</a> </td></tr> <tr> <td><a href="/w/index.php?title=DPPG-NH4&action=edit&redlink=1" class="new" title="DPPG-NH4 (page does not exist)">DPPG-NH4</a></td> <td>73548-70-6</td> <td>1,2-Dipalmitoyl-<i>sn</i>-glycero-3[phospho-rac-(1-glycerol...) (ammonium salt)</td> <td><a href="/wiki/Phosphatidylglycerol" title="Phosphatidylglycerol">Phosphatidylglycerol</a> </td></tr> <tr> <td><a href="/w/index.php?title=DPPS-NA&action=edit&redlink=1" class="new" title="DPPS-NA (page does not exist)">DPPS-NA</a></td> <td></td> <td>1,2-Dipalmitoyl-<i>sn</i>-glycero-3-phosphoserine (sodium salt)</td> <td><a href="/wiki/Phosphatidylserine" title="Phosphatidylserine">Phosphatidylserine</a> </td></tr> <tr> <td><a href="/w/index.php?title=DSPA-NA&action=edit&redlink=1" class="new" title="DSPA-NA (page does not exist)">DSPA-NA</a></td> <td>108321-18-2</td> <td>1,2-Distearoyl-<i>sn</i>-glycero-3-phosphate (sodium salt)</td> <td><a href="/wiki/Phosphatidic_acid" title="Phosphatidic acid">Phosphatidic acid</a> </td></tr> <tr> <td><a href="/wiki/DSPC" class="mw-redirect" title="DSPC">DSPC</a></td> <td>816-94-4</td> <td>1,2-Distearoyl-<i>sn</i>-glycero-3-phosphocholine</td> <td><a href="/wiki/Phosphatidylcholine" title="Phosphatidylcholine">Phosphatidylcholine</a> </td></tr> <tr> <td><a href="/wiki/DSPE" class="mw-redirect" title="DSPE">DSPE</a></td> <td>1069-79-0</td> <td>1,2-Distearoyl-<i>sn</i>-glycero-3-phosphoethanolamine</td> <td><a href="/wiki/Phosphatidylethanolamine" title="Phosphatidylethanolamine">Phosphatidylethanolamine</a> </td></tr> <tr> <td><a href="/w/index.php?title=DSPG-NA&action=edit&redlink=1" class="new" title="DSPG-NA (page does not exist)">DSPG-NA</a></td> <td>67232-82-0</td> <td>1,2-Distearoyl-<i>sn</i>-glycero-3[phospho-rac-(1-glycerol...) (sodium salt)</td> <td><a href="/wiki/Phosphatidylglycerol" title="Phosphatidylglycerol">Phosphatidylglycerol</a> </td></tr> <tr> <td><a href="/w/index.php?title=DSPG-NH4&action=edit&redlink=1" class="new" title="DSPG-NH4 (page does not exist)">DSPG-NH4</a></td> <td>108347-80-4</td> <td>1,2-Distearoyl-<i>sn</i>-glycero-3[phospho-rac-(1-glycerol...) (ammonium salt)</td> <td><a href="/wiki/Phosphatidylglycerol" title="Phosphatidylglycerol">Phosphatidylglycerol</a> </td></tr> <tr> <td><a href="/w/index.php?title=DSPS-NA&action=edit&redlink=1" class="new" title="DSPS-NA (page does not exist)">DSPS-NA</a></td> <td></td> <td>1,2-Distearoyl-<i>sn</i>-glycero-3-phosphoserine (sodium salt)</td> <td><a href="/wiki/Phosphatidylserine" title="Phosphatidylserine">Phosphatidylserine</a> </td></tr> <tr> <td><a href="/wiki/Phosphatidylcholine" title="Phosphatidylcholine">EPC</a></td> <td></td> <td>Egg-PC</td> <td><a href="/wiki/Phosphatidylcholine" title="Phosphatidylcholine">Phosphatidylcholine</a> </td></tr> <tr> <td>HEPC</td> <td></td> <td>Hydrogenated egg PC</td> <td><a href="/wiki/Phosphatidylcholine" title="Phosphatidylcholine">Phosphatidylcholine</a> </td></tr> <tr> <td><a href="/wiki/Phosphatidylcholine" title="Phosphatidylcholine">HSPC</a></td> <td></td> <td>Hydrogenated soy PC</td> <td><a href="/wiki/Phosphatidylcholine" title="Phosphatidylcholine">Phosphatidylcholine</a> </td></tr> <tr> <td><a href="/w/index.php?title=LYSOPC_MYRISTIC&action=edit&redlink=1" class="new" title="LYSOPC MYRISTIC (page does not exist)">LYSOPC MYRISTIC</a></td> <td>18194-24-6</td> <td>1-Myristoyl-<i>sn</i>-glycero-3-phosphocholine</td> <td><a href="/wiki/Lysophosphatidylcholine" title="Lysophosphatidylcholine">Lysophosphatidylcholine</a> </td></tr> <tr> <td><a href="/w/index.php?title=LYSOPC_PALMITIC&action=edit&redlink=1" class="new" title="LYSOPC PALMITIC (page does not exist)">LYSOPC PALMITIC</a></td> <td>17364-16-8</td> <td>1-Palmitoyl-<i>sn</i>-glycero-3-phosphocholine</td> <td><a href="/wiki/Lysophosphatidylcholine" title="Lysophosphatidylcholine">Lysophosphatidylcholine</a> </td></tr> <tr> <td><a href="/w/index.php?title=LYSOPC_STEARIC&action=edit&redlink=1" class="new" title="LYSOPC STEARIC (page does not exist)">LYSOPC STEARIC</a></td> <td>19420-57-6</td> <td>1-Stearoyl-<i>sn</i>-glycero-3-phosphocholine</td> <td><a href="/wiki/Lysophosphatidylcholine" title="Lysophosphatidylcholine">Lysophosphatidylcholine</a> </td></tr> <tr> <td><a href="/wiki/Milk" title="Milk">Milk</a> <a href="/wiki/Sphingomyelin" title="Sphingomyelin">Sphingomyelin MPPC</a></td> <td></td> <td>1-Myristoyl-2-palmitoyl-<i>sn</i>-glycero 3-phosphocholine</td> <td><a href="/wiki/Phosphatidylcholine" title="Phosphatidylcholine">Phosphatidylcholine</a> </td></tr> <tr> <td><a href="/w/index.php?title=MSPC&action=edit&redlink=1" class="new" title="MSPC (page does not exist)">MSPC</a></td> <td></td> <td>1-Myristoyl-2-stearoyl-<i>sn</i>-glycero-3–phosphocholine</td> <td><a href="/wiki/Phosphatidylcholine" title="Phosphatidylcholine">Phosphatidylcholine</a> </td></tr> <tr> <td><a href="/w/index.php?title=PMPC&action=edit&redlink=1" class="new" title="PMPC (page does not exist)">PMPC</a></td> <td></td> <td>1-Palmitoyl-2-myristoyl-<i>sn</i>-glycero-3–phosphocholine</td> <td><a href="/wiki/Phosphatidylcholine" title="Phosphatidylcholine">Phosphatidylcholine</a> </td></tr> <tr> <td><a href="/wiki/POPC" title="POPC">POPC</a></td> <td>26853-31-6</td> <td>1-Palmitoyl-2-oleoyl-<i>sn</i>-glycero-3-phosphocholine</td> <td><a href="/wiki/Phosphatidylcholine" title="Phosphatidylcholine">Phosphatidylcholine</a> </td></tr> <tr> <td><a href="/w/index.php?title=POPE_(lipid)&action=edit&redlink=1" class="new" title="POPE (lipid) (page does not exist)">POPE</a></td> <td></td> <td>1-Palmitoyl-2-oleoyl-<i>sn</i>-glycero-3-phosphoethanolamine</td> <td><a href="/wiki/Phosphatidylethanolamine" title="Phosphatidylethanolamine">Phosphatidylethanolamine</a> </td></tr> <tr> <td><a href="/w/index.php?title=POPG-NA&action=edit&redlink=1" class="new" title="POPG-NA (page does not exist)">POPG-NA</a></td> <td>81490-05-3</td> <td>1-Palmitoyl-2-oleoyl-<i>sn</i>-glycero-3[phospho-rac-(1-glycerol)...] (sodium salt)</td> <td><a href="/wiki/Phosphatidylglycerol" title="Phosphatidylglycerol">Phosphatidylglycerol</a> </td></tr> <tr> <td><a href="/w/index.php?title=PSPC_(lipid)&action=edit&redlink=1" class="new" title="PSPC (lipid) (page does not exist)">PSPC</a></td> <td></td> <td>1-Palmitoyl-2-stearoyl-<i>sn</i>-glycero-3–phosphocholine</td> <td><a href="/wiki/Phosphatidylcholine" title="Phosphatidylcholine">Phosphatidylcholine</a> </td></tr> <tr> <td><a href="/w/index.php?title=SMPC&action=edit&redlink=1" class="new" title="SMPC (page does not exist)">SMPC</a></td> <td></td> <td>1-Stearoyl-2-myristoyl-<i>sn</i>-glycero-3–phosphocholine</td> <td><a href="/wiki/Phosphatidylcholine" title="Phosphatidylcholine">Phosphatidylcholine</a> </td></tr> <tr> <td><a href="/w/index.php?title=SOPC&action=edit&redlink=1" class="new" title="SOPC (page does not exist)">SOPC</a></td> <td></td> <td>1-Stearoyl-2-oleoyl-<i>sn</i>-glycero-3-phosphocholine</td> <td><a href="/wiki/Phosphatidylcholine" title="Phosphatidylcholine">Phosphatidylcholine</a> </td></tr> <tr> <td><a href="/wiki/SPPC" class="mw-redirect" title="SPPC">SPPC</a></td> <td></td> <td>1-Stearoyl-2-palmitoyl-<i>sn</i>-glycero-3-phosphocholine</td> <td><a href="/wiki/Phosphatidylcholine" title="Phosphatidylcholine">Phosphatidylcholine</a> </td></tr></tbody></table> <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=Phospholipid&action=edit&section=17" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Cable_theory" title="Cable theory">Cable theory</a></li> <li><a href="/wiki/Galactolipid" title="Galactolipid">Galactolipid</a></li> <li><a href="/wiki/Sulfolipid" title="Sulfolipid">Sulfolipid</a></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=Phospholipid&action=edit&section=18" 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 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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 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(2005). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6725895">"Multiple Receptors Coupled to Phospholipase C Gate Long-Term Depression in Visual Cortex"</a>. <i>Journal of Neuroscience</i>. <b>25</b> (49): 11433–11443. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1523%2FJNEUROSCI.4084-05.2005">10.1523/JNEUROSCI.4084-05.2005</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6725895">6725895</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16339037">16339037</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Neuroscience&rft.atitle=Multiple+Receptors+Coupled+to+Phospholipase+C+Gate+Long-Term+Depression+in+Visual+Cortex&rft.volume=25&rft.issue=49&rft.pages=11433-11443&rft.date=2005&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6725895%23id-name%3DPMC&rft_id=info%3Apmid%2F16339037&rft_id=info%3Adoi%2F10.1523%2FJNEUROSCI.4084-05.2005&rft.aulast=Choi&rft.aufirst=S.-Y.&rft.au=Chang%2C+J.&rft.au=Jiang%2C+B.&rft.au=Seol%2C+G.+H.&rft.au=Min%2C+S.+S.&rft.au=Han%2C+J.+S.&rft.au=Shin%2C+H.+S.&rft.au=Gallagher%2C+M.&rft.au=Kirkwood%2C+A.&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6725895&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhospholipid" class="Z3988"></span></span> </li> <li id="cite_note-19"><span class="mw-cite-backlink"><b><a href="#cite_ref-19">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCronshawKouroumalisParryWebb2006" class="citation journal cs1">Cronshaw, D. G.; Kouroumalis, A.; Parry, R.; Webb, A.; Brown, Z.; Ward, S. G. (2006). <a rel="nofollow" class="external text" href="https://doi.org/10.1189%2Fjlb.0106035">"Evidence that phospholipase C-dependent, calcium-independent mechanisms are required for directional migration of T lymphocytes in response to the CCR4 ligands CCL17 and CCL22"</a>. <i>Journal of Leukocyte Biology</i>. <b>79</b> (6): 1369–1380. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1189%2Fjlb.0106035">10.1189/jlb.0106035</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16614259">16614259</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Leukocyte+Biology&rft.atitle=Evidence+that+phospholipase+C-dependent%2C+calcium-independent+mechanisms+are+required+for+directional+migration+of+T+lymphocytes+in+response+to+the+CCR4+ligands+CCL17+and+CCL22&rft.volume=79&rft.issue=6&rft.pages=1369-1380&rft.date=2006&rft_id=info%3Adoi%2F10.1189%2Fjlb.0106035&rft_id=info%3Apmid%2F16614259&rft.aulast=Cronshaw&rft.aufirst=D.+G.&rft.au=Kouroumalis%2C+A.&rft.au=Parry%2C+R.&rft.au=Webb%2C+A.&rft.au=Brown%2C+Z.&rft.au=Ward%2C+S.+G.&rft_id=https%3A%2F%2Fdoi.org%2F10.1189%252Fjlb.0106035&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhospholipid" class="Z3988"></span></span> </li> </ol></div></div> <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 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class="mw-selflink selflink">Phospholipids</a></li> <li><a href="/wiki/Lipoprotein" title="Lipoprotein">Lipoproteins</a></li> <li><a href="/wiki/Sphingolipid" title="Sphingolipid">Sphingolipids</a></li> <li><a href="/wiki/Sterol" title="Sterol">Sterols</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Membrane_protein" title="Membrane protein">Membrane proteins</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/Membrane_glycoproteins" title="Membrane glycoproteins">Membrane glycoproteins</a></li> <li><a href="/wiki/Integral_membrane_protein" title="Integral membrane protein">Integral membrane proteins</a>/<a href="/wiki/Transmembrane_protein" title="Transmembrane protein">transmembrane protein</a></li> <li><a href="/wiki/Peripheral_membrane_protein" title="Peripheral membrane protein">Peripheral membrane protein</a>/<a href="/wiki/Lipid-anchored_protein" title="Lipid-anchored protein">Lipid-anchored protein</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 hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Caveolae" title="Caveolae">Caveolae/Coated pits</a></li> <li><a href="/wiki/Cell_junction" title="Cell junction">Cell junctions</a></li> <li><a href="/wiki/Glycocalyx" title="Glycocalyx">Glycocalyx</a></li> <li><a href="/wiki/Lipid_raft" title="Lipid raft">Lipid raft/microdomains</a></li> <li><a href="/wiki/Membrane_contact_site" title="Membrane contact site">Membrane contact sites</a></li> <li><a href="/wiki/Membrane_nanotube" class="mw-redirect" title="Membrane nanotube">Membrane nanotubes</a></li> <li><a href="/wiki/Myelin" title="Myelin">Myelin sheath</a></li> <li><a href="/wiki/Node_of_Ranvier" title="Node of Ranvier">Nodes of Ranvier</a></li> <li><a href="/wiki/Nuclear_envelope" title="Nuclear envelope">Nuclear envelope</a></li> <li><a href="/wiki/Phycobilisome" title="Phycobilisome">Phycobilisomes</a></li> <li><a href="/wiki/Porosome" title="Porosome">Porosomes</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 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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"><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" 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