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Inositol phosphate - Wikipedia

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class="vector-toc-list"> <li id="toc-Inositol_trisphosphate" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Inositol_trisphosphate"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1</span> <span>Inositol trisphosphate</span> </div> </a> <ul id="toc-Inositol_trisphosphate-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Other"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.2</span> <span>Other</span> </div> </a> <ul id="toc-Other-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Inositol_hexaphosphate" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Inositol_hexaphosphate"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.3</span> <span>Inositol hexaphosphate</span> </div> </a> <ul id="toc-Inositol_hexaphosphate-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> 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href="https://ca.wikipedia.org/wiki/Fosfatidilinositol" title="Fosfatidilinositol – Catalan" lang="ca" hreflang="ca" data-title="Fosfatidilinositol" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Inositolphosphate" title="Inositolphosphate – German" lang="de" hreflang="de" data-title="Inositolphosphate" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Fosfoinos%C3%ADtido" title="Fosfoinosítido – Spanish" lang="es" hreflang="es" data-title="Fosfoinosítido" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Inositol_phosphate" title="Inositol phosphate – French" lang="fr" hreflang="fr" data-title="Inositol phosphate" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Inositol_fosfato" title="Inositol fosfato – Galician" lang="gl" hreflang="gl" data-title="Inositol fosfato" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%A4%E3%83%8E%E3%82%B7%E3%83%88%E3%83%BC%E3%83%AB%E3%83%AA%E3%83%B3%E9%85%B8" title="イノシトールリン酸 – Japanese" lang="ja" hreflang="ja" data-title="イノシトールリン酸" data-language-autonym="日本語" data-language-local-name="Japanese" 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<div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Inositol_structure.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/Inositol_structure.png/220px-Inositol_structure.png" decoding="async" width="220" height="203" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/Inositol_structure.png/330px-Inositol_structure.png 1.5x, //upload.wikimedia.org/wikipedia/commons/a/a2/Inositol_structure.png 2x" data-file-width="357" data-file-height="329" /></a><figcaption><a href="/wiki/Inositol" title="Inositol">Inositol</a></figcaption></figure> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Phosphate_Group.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d2/Phosphate_Group.svg/220px-Phosphate_Group.svg.png" decoding="async" width="220" height="133" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d2/Phosphate_Group.svg/330px-Phosphate_Group.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d2/Phosphate_Group.svg/440px-Phosphate_Group.svg.png 2x" data-file-width="1025" data-file-height="621" /></a><figcaption><a href="/wiki/Phosphate" title="Phosphate">Phosphate</a> group</figcaption></figure> <p><b>Inositol phosphates</b> are a group of mono- to hexa<a href="/wiki/Phosphorylated" class="mw-redirect" title="Phosphorylated">phosphorylated</a> <a href="/wiki/Inositol" title="Inositol">inositols</a>. Each form of inositol phosphate is distinguished by the number and position of the phosphate group on the inositol ring. </p> <ul><li>inositol monophosphate (IP)</li> <li>inositol bisphosphate (IP<sub>2</sub>)</li> <li><a href="/wiki/Inositol_trisphosphate" title="Inositol trisphosphate">inositol trisphosphate</a> (IP<sub>3</sub>)</li> <li>inositol tetrakisphosphate (IP<sub>4</sub>)</li> <li><a href="/wiki/Inositol_pentakisphosphate" title="Inositol pentakisphosphate">inositol pentakisphosphate</a> (IP<sub>5</sub>)</li> <li>inositol hexaphosphate (IP<sub>6</sub>) also known as <a href="/wiki/Phytic_acid" title="Phytic acid">phytic acid</a>, or phytate (as a salt).</li></ul> <p>A series of phosphorylation and dephosphorylation reactions are carried out by at least 19 phosphoinositide <a href="/wiki/Kinase" title="Kinase">kinases</a> and 28 phosphoinositide <a href="/wiki/Phosphatase" title="Phosphatase">phosphatase</a> enzymes<sup id="cite_ref-Shamsuddin_2015_1-0" class="reference"><a href="#cite_note-Shamsuddin_2015-1"><span class="cite-bracket">&#91;</span>1<span class="cite-bracket">&#93;</span></a></sup> allowing for the inter-conversion between the inositol phosphate compounds based on cellular demand. </p><p>Inositol phosphates play a crucial role in various signal transduction pathways responsible for cell growth and differentiation, apoptosis, DNA repair, RNA export, regeneration of ATP and more. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Functions">Functions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Inositol_phosphate&amp;action=edit&amp;section=1" title="Edit section: Functions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Inositol_trisphosphate">Inositol trisphosphate</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Inositol_phosphate&amp;action=edit&amp;section=2" title="Edit section: Inositol trisphosphate"><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/Inositol_trisphosphate" title="Inositol trisphosphate">Inositol trisphosphate</a></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:IP3_veikimas.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7f/IP3_veikimas.png/220px-IP3_veikimas.png" decoding="async" width="220" height="92" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7f/IP3_veikimas.png/330px-IP3_veikimas.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7f/IP3_veikimas.png/440px-IP3_veikimas.png 2x" data-file-width="956" data-file-height="401" /></a><figcaption>inositol-phospholipid signaling pathway</figcaption></figure> <p>The inositol-phospholipid signaling pathway is responsible for the generation of IP3 through the cleavage of <a href="/wiki/Phosphatidylinositol_4,5-bisphosphate" title="Phosphatidylinositol 4,5-bisphosphate">Phosphatidylinositol 4,5-bisphosphate</a> (PIP2) found in the lipid bi-layer of the plasma membrane by <a href="/wiki/Phospholipase_C" title="Phospholipase C">phospholipase C</a> in response to either <a href="/wiki/Receptor_tyrosine_kinase" title="Receptor tyrosine kinase">receptor tyrosine kinase</a> or <a href="/wiki/Gq_alpha_subunit" title="Gq alpha subunit">Gq alpha subunit</a>-<a href="/wiki/G_protein-coupled_receptor" title="G protein-coupled receptor">G protein-coupled receptor</a> signaling. Soluble <a href="/wiki/Inositol_trisphosphate" title="Inositol trisphosphate">inositol trisphosphate</a> (IP3) is able to rapidly diffuse into the cytosol and bind to the <a href="/wiki/Inositol_trisphosphate_receptor" title="Inositol trisphosphate receptor">inositol trisphosphate receptor</a> (InsP3Rs) calcium channels located in the endoplasmic reticulum. This releases calcium into the cytosol, serving as a rapid and potent signal for various cellular processes.<sup id="cite_ref-Shamsuddin_2015_1-1" class="reference"><a href="#cite_note-Shamsuddin_2015-1"><span class="cite-bracket">&#91;</span>1<span class="cite-bracket">&#93;</span></a></sup> </p><p><i>Further reading: <a href="/wiki/Function_of_calcium_in_humans" class="mw-redirect" title="Function of calcium in humans">Function of calcium in humans</a></i> </p> <div class="mw-heading mw-heading3"><h3 id="Other">Other</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Inositol_phosphate&amp;action=edit&amp;section=3" title="Edit section: Other"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Inositol tetra-, <a href="/wiki/Inositol_pentakisphosphate" title="Inositol pentakisphosphate">penta-</a>, and hexa-phosphates have been implicated in <a href="/wiki/Gene_expression" title="Gene expression">gene expression</a>.<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">&#91;</span>2<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">&#91;</span>3<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Inositol_hexaphosphate">Inositol hexaphosphate</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Inositol_phosphate&amp;action=edit&amp;section=4" title="Edit section: Inositol hexaphosphate"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Inositol hexaphosphate (IP6) is the most abundant inositol phosphate isomer found. IP6 is solely involved in various biological activities such as neurotransmission, immune response, regulation of kinase and phosphatase proteins as well as activation of calcium channels. <sup id="cite_ref-Shamsuddin_2015_1-2" class="reference"><a href="#cite_note-Shamsuddin_2015-1"><span class="cite-bracket">&#91;</span>1<span class="cite-bracket">&#93;</span></a></sup> IP6 is also involved in ATP regeneration seen in plants as well as insulin <a href="/wiki/Exocytosis" title="Exocytosis">exocytosis</a> in <a href="/wiki/Beta_cell" title="Beta cell">pancreatic β cells</a>. </p><p>Inositol hexaphosphate also facilitates the formation of the six-helix bundle and assembly of the immature HIV-1 Gag lattice. IP6 makes ionic contacts with two rings of lysine residues at the centre of the Gag hexamer. Proteolytic cleavage then unmasks an alternative binding site, where IP6 interaction promotes the assembly of the mature capsid lattice. These studies identify IP6 as a naturally occurring small molecule that promotes both assembly and maturation of HIV-1.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">&#91;</span>4<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Inositol_phosphate&amp;action=edit&amp;section=5" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-Shamsuddin_2015-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-Shamsuddin_2015_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Shamsuddin_2015_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Shamsuddin_2015_1-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFShamsuddinYang2015" class="citation book cs1">Shamsuddin AK, Yang GY (2015-03-04). "Safety of Inositol and Inositol Phosphates". In Shamsuddin A, Yang GY (eds.). <i>Inositol &amp; its Phosphates: Basic Science to Practical Applications</i>. Bentham Science Publishers. pp.&#160;275–282. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.2174%2F9781681080079115010024">10.2174/9781681080079115010024</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/9781681080079" title="Special:BookSources/9781681080079"><bdi>9781681080079</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=bookitem&amp;rft.atitle=Safety+of+Inositol+and+Inositol+Phosphates&amp;rft.btitle=Inositol+%26+its+Phosphates%3A+Basic+Science+to+Practical+Applications&amp;rft.pages=275-282&amp;rft.pub=Bentham+Science+Publishers&amp;rft.date=2015-03-04&amp;rft_id=info%3Adoi%2F10.2174%2F9781681080079115010024&amp;rft.isbn=9781681080079&amp;rft.aulast=Shamsuddin&amp;rft.aufirst=AK&amp;rft.au=Yang%2C+GY&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AInositol+phosphate" class="Z3988"></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFShenXiaoRanalloWu2003" class="citation journal cs1">Shen X, Xiao H, Ranallo R, Wu WH, Wu C (January 2003). <a rel="nofollow" class="external text" href="https://zenodo.org/record/1230822">"Modulation of ATP-dependent chromatin-remodeling complexes by inositol polyphosphates"</a>. <i>Science</i>. <b>299</b> (5603): 112–114. <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/10.1126%2Fscience.1078068">10.1126/science.1078068</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/12434013">12434013</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a>&#160;<a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:8381889">8381889</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Science&amp;rft.atitle=Modulation+of+ATP-dependent+chromatin-remodeling+complexes+by+inositol+polyphosphates&amp;rft.volume=299&amp;rft.issue=5603&amp;rft.pages=112-114&amp;rft.date=2003-01&amp;rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A8381889%23id-name%3DS2CID&amp;rft_id=info%3Apmid%2F12434013&amp;rft_id=info%3Adoi%2F10.1126%2Fscience.1078068&amp;rft.aulast=Shen&amp;rft.aufirst=X&amp;rft.au=Xiao%2C+H&amp;rft.au=Ranallo%2C+R&amp;rft.au=Wu%2C+WH&amp;rft.au=Wu%2C+C&amp;rft_id=https%3A%2F%2Fzenodo.org%2Frecord%2F1230822&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AInositol+phosphate" class="Z3988"></span></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFStegerHaswellMillerWente2003" class="citation journal cs1">Steger DJ, Haswell ES, Miller AL, Wente SR, O'Shea EK (January 2003). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1458531">"Regulation of chromatin remodeling by inositol polyphosphates"</a>. <i>Science</i>. <b>299</b> (5603): 114–116. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1126%2Fscience.1078062">10.1126/science.1078062</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a>&#160;<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1458531">1458531</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/12434012">12434012</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Science&amp;rft.atitle=Regulation+of+chromatin+remodeling+by+inositol+polyphosphates&amp;rft.volume=299&amp;rft.issue=5603&amp;rft.pages=114-116&amp;rft.date=2003-01&amp;rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1458531%23id-name%3DPMC&amp;rft_id=info%3Apmid%2F12434012&amp;rft_id=info%3Adoi%2F10.1126%2Fscience.1078062&amp;rft.aulast=Steger&amp;rft.aufirst=DJ&amp;rft.au=Haswell%2C+ES&amp;rft.au=Miller%2C+AL&amp;rft.au=Wente%2C+SR&amp;rft.au=O%27Shea%2C+EK&amp;rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1458531&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AInositol+phosphate" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link 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(identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/30069050">30069050</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Nature&amp;rft.atitle=Inositol+phosphates+are+assembly+co-factors+for+HIV-1&amp;rft.volume=560&amp;rft.issue=7719&amp;rft.pages=509-512&amp;rft.date=2018-08&amp;rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6242333%23id-name%3DPMC&amp;rft_id=info%3Apmid%2F30069050&amp;rft_id=info%3Adoi%2F10.1038%2Fs41586-018-0396-4&amp;rft_id=info%3Abibcode%2F2018Natur.560..509D&amp;rft.aulast=Dick&amp;rft.aufirst=RA&amp;rft.au=Zadrozny%2C+KK&amp;rft.au=Xu%2C+C&amp;rft.au=Schur%2C+FK&amp;rft.au=Lyddon%2C+TD&amp;rft.au=Ricana%2C+CL&amp;rft.au=Wagner%2C+JM&amp;rft.au=Perilla%2C+JR&amp;rft.au=Ganser-Pornillos%2C+BK&amp;rft.au=Johnson%2C+MC&amp;rft.au=Pornillos%2C+O&amp;rft.au=Vogt%2C+VM&amp;rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6242333&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AInositol+phosphate" class="Z3988"></span></span> </li> </ol></div> 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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 class="mw-selflink selflink">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> <!-- NewPP limit report Parsed by mw‐api‐ext.codfw.main‐f5fb67494‐hsxzx Cached time: 20241128224247 Cache expiry: 2592000 Reduced expiry: false Complications: [vary‐revision‐sha1, show‐toc] CPU time usage: 0.223 seconds Real time usage: 0.276 seconds Preprocessor visited node count: 379/1000000 Post‐expand include size: 27871/2097152 bytes Template argument size: 0/2097152 bytes Highest expansion depth: 6/100 Expensive parser function count: 2/500 Unstrip recursion depth: 1/20 Unstrip post‐expand size: 25709/5000000 bytes Lua time usage: 0.159/10.000 seconds Lua memory usage: 4089257/52428800 bytes Number of Wikibase entities loaded: 0/400 --> <!-- Transclusion expansion time report (%,ms,calls,template) 100.00% 229.752 1 -total 39.05% 89.715 1 Template:Phospholipids 38.78% 89.101 3 Template:Navbox 34.19% 78.543 1 Template:Cite_book 15.82% 36.344 1 Template:Main 6.83% 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