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<tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Cerebrosterol.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4b/Cerebrosterol.svg/200px-Cerebrosterol.svg.png" decoding="async" width="200" height="142" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4b/Cerebrosterol.svg/300px-Cerebrosterol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4b/Cerebrosterol.svg/400px-Cerebrosterol.svg.png 2x" data-file-width="541" data-file-height="384" /></a></span> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">(24<i>S</i>)-Cholest-5-ene-3β,24-diol</div> </td></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature#Systematic_name" title="Chemical nomenclature">Systematic IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">(1<i>R</i>,3a<i>S</i>,3b<i>S</i>,7<i>S</i>,9a<i>R</i>,9b<i>S</i>,11a<i>R</i>)-1-[(2<i>R</i>,5<i>S</i>)-5-Hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-2,3,3a,3b,4,6,7,8,9,9a,9b,10,11,11a-tetradecahydro-1<i>H</i>-cyclopenta[<i>a</i>]phenanthren-7-ol</div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">cerebrosterol</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=474-73-7">474-73-7</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=C%5BC%40H%5D%28CC%5BC%40%40H%5D%28C%28C%29C%29O%29%5BC%40H%5D1CC%5BC%40%40H%5D2%5BC%40%40%5D1%28CC%5BC%40H%5D3%5BC%40H%5D2CC%3DC4%5BC%40%40%5D3%28CC%5BC%40%40H%5D%28C4%29O%29C%29C">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Beilstein_database" title="Beilstein database">Beilstein Reference</a></div> </td> <td>3218472 </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=34310">CHEBI:34310</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" 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Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID101313419">DTXSID101313419</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q27071873#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C27H46O2/c1-17(2)25(29)11-6-18(3)22-9-10-23-21-8-7-19-16-20(28)12-14-26(19,4)24(21)13-15-27(22,23)5/h7,17-18,20-25,28-29H,6,8-16H2,1-5H3/t18-,20+,21+,22-,23+,24+,25+,26+,27-/m1/s1</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: IOWMKBFJCNLRTC-XWXSNNQWSA-N</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">C[C@H](CC[C@@H](C(C)C)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>27</sub><span title="Hydrogen">H</span><sub>46</sub><span title="Oxygen">O</span><sub>2</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002402663000000000♠"></span>402.663</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>24<i>S</i>-Hydroxycholesterol</b> (<b>24S-HC</b>), also known as <b>cholest-5-ene-3,24-diol</b> or <b>cerebrosterol</b>, is an <a href="/wiki/Endogenous" class="mw-redirect" title="Endogenous">endogenous</a> <a href="/wiki/Oxysterol" title="Oxysterol">oxysterol</a> produced by <a href="/wiki/Neuron" title="Neuron">neurons</a> in the <a href="/wiki/Brain" title="Brain">brain</a> to maintain <a href="/wiki/Cholesterol" title="Cholesterol">cholesterol</a> <a href="/wiki/Homeostasis" title="Homeostasis">homeostasis</a>.<sup id="cite_ref-pmid27174096_1-0" class="reference"><a href="#cite_note-pmid27174096-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> It was discovered in 1953 by Alberto Ercoli, S. Di Frisco, and Pietro de Ruggieri, who first isolated the molecule in the horse brain<sup id="cite_ref-pmid13105923_2-0" class="reference"><a href="#cite_note-pmid13105923-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> and then demonstrated its presence in the <a href="/wiki/Human_brain" title="Human brain">human brain</a>.<sup id="cite_ref-pmid13140512_3-0" class="reference"><a href="#cite_note-pmid13140512-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Structure">Structure</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=24S-Hydroxycholesterol&action=edit&section=1" title="Edit section: Structure"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>24S-HC is produced by a <a href="/wiki/Hydroxy_group" title="Hydroxy group">hydroxy group</a> <a href="/wiki/Substitution_reaction" title="Substitution reaction">substitution</a> at <a href="/wiki/Steroid#Nomenclature" title="Steroid">carbon number</a> 24 in cholesterol, catalyzed by the <a href="/wiki/Enzyme" title="Enzyme">enzyme</a> <a href="/wiki/Cholesterol_24-hydroxylase" title="Cholesterol 24-hydroxylase">cholesterol 24-hydroxylase</a> (CYP46A1).<sup id="cite_ref-pmid12686551_4-0" class="reference"><a href="#cite_note-pmid12686551-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-default-size mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Coversion_of_cholesterol_into_24s-hydroxycholesterol.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b8/Coversion_of_cholesterol_into_24s-hydroxycholesterol.png/440px-Coversion_of_cholesterol_into_24s-hydroxycholesterol.png" decoding="async" width="440" height="134" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b8/Coversion_of_cholesterol_into_24s-hydroxycholesterol.png/660px-Coversion_of_cholesterol_into_24s-hydroxycholesterol.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b8/Coversion_of_cholesterol_into_24s-hydroxycholesterol.png/880px-Coversion_of_cholesterol_into_24s-hydroxycholesterol.png 2x" data-file-width="1110" data-file-height="338" /></a><figcaption>Production of 24S-hydroxycholesterol from cholesterol, as catalyzed by <a href="/wiki/CYP46A1" class="mw-redirect" title="CYP46A1">CYP46A1</a>.</figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Function">Function</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=24S-Hydroxycholesterol&action=edit&section=2" title="Edit section: Function"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>24S-HC binds to <a href="/wiki/Apolipoprotein" title="Apolipoprotein">apolipoproteins</a> such as <a href="/wiki/ApoE" class="mw-redirect" title="ApoE">apoE</a>, <a href="/wiki/Clusterin" title="Clusterin">apoJ</a>, and <a href="/wiki/ApoA1" class="mw-redirect" title="ApoA1">apoA1</a> to form <a href="/wiki/High-density_lipoprotein" title="High-density lipoprotein">HDL</a>-like complexes<sup id="cite_ref-pmid20211758_5-0" class="reference"><a href="#cite_note-pmid20211758-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> which can cross the <a href="/wiki/Blood%E2%80%93brain_barrier" title="Blood–brain barrier">blood–brain barrier</a> more easily than free <a href="/wiki/Cholesterol" title="Cholesterol">cholesterol</a>. Thus, 24S-HC production serves as one of several counterbalancing mechanisms for cholesterol synthesis in the brain.<sup id="cite_ref-pmid27174096_1-1" class="reference"><a href="#cite_note-pmid27174096-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid17393206_6-0" class="reference"><a href="#cite_note-pmid17393206-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> After entering general blood circulation and traveling to the <a href="/wiki/Liver" title="Liver">liver</a>, 24S-HC can be <a href="/wiki/Sulfation" title="Sulfation">sulfated</a>, <a href="/wiki/Glucuronidation" title="Glucuronidation">glucuronidated</a>, or converted into <a href="/wiki/Bile_acid" title="Bile acid">bile acids</a>, which can ultimately be <a href="/wiki/Excretion" title="Excretion">excreted</a>.<sup id="cite_ref-pmid16866909_7-0" class="reference"><a href="#cite_note-pmid16866909-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p><p>24S-HC is an agonist of <a href="/wiki/Liver_X_receptor" title="Liver X receptor">liver X receptors</a>, a class of <a href="/wiki/Nuclear_receptor" title="Nuclear receptor">nuclear receptors</a> that sense oxysterols. In the brain, <a href="/wiki/Liver_X_receptor_beta" title="Liver X receptor beta">liver X receptor beta</a> is the primary LXR type, which interacts with 24S-HC.<sup id="cite_ref-pmid20211758_5-1" class="reference"><a href="#cite_note-pmid20211758-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> 24S-HC levels sensed by LXRs can regulate the expression of <a href="/wiki/SREBP" class="mw-redirect" title="SREBP">SREBP</a> mRNA and protein, which in turn regulate <a href="/wiki/Cholesterol#Biosynthesis" title="Cholesterol">cholesterol synthesis</a> and <a href="/wiki/Fatty_acid_synthesis" title="Fatty acid synthesis">fatty acid synthesis</a>.<sup id="cite_ref-pmid20053345_8-0" class="reference"><a href="#cite_note-pmid20053345-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p><p>24S-HC may participate in several aspects of <a href="/wiki/Brain_development" class="mw-redirect" title="Brain development">brain development</a> and function, such as <a href="/wiki/Axon" title="Axon">axon</a> and <a href="/wiki/Dendrite" title="Dendrite">dendrite</a> growth or <a href="/wiki/Synaptogenesis" title="Synaptogenesis">synaptogenesis</a>,<sup id="cite_ref-pmid12686551_4-1" class="reference"><a href="#cite_note-pmid12686551-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> as well as acting as a positive <a href="/wiki/Allosteric_modulator" title="Allosteric modulator">allosteric modulator</a> of <a href="/wiki/NMDA_receptor" title="NMDA receptor">NMDA receptors</a>.<sup id="cite_ref-pmid24174662_9-0" class="reference"><a href="#cite_note-pmid24174662-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Regulation of 24S-HC metabolism in neurons may play a role in their health and function, as well as their response to injury or disease.<sup id="cite_ref-pmid25628343_10-0" class="reference"><a href="#cite_note-pmid25628343-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Blood_plasma" title="Blood plasma">Blood plasma</a> levels of 24S-HC may be altered after acute <a href="/wiki/Brain_damage" class="mw-redirect" title="Brain damage">brain injuries</a> such as <a href="/wiki/Stroke" title="Stroke">stroke</a><sup id="cite_ref-pmid28346482_11-0" class="reference"><a href="#cite_note-pmid28346482-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> or in <a href="/wiki/Neurodegenerative_disease" title="Neurodegenerative disease">neurodegenerative diseases</a> such as <a href="/wiki/Alzheimer%27s_disease" title="Alzheimer's disease">Alzheimer's disease</a>, <a href="/wiki/Huntington%27s_disease" title="Huntington's disease">Huntington's disease</a>, and <a href="/wiki/Multiple_sclerosis" title="Multiple sclerosis">multiple sclerosis</a>.<sup id="cite_ref-pmid23041502_12-0" class="reference"><a href="#cite_note-pmid23041502-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid25539717_13-0" class="reference"><a href="#cite_note-pmid25539717-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</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=24S-Hydroxycholesterol&action=edit&section=3" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-pmid27174096-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-pmid27174096_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid27174096_1-1"><sup><i><b>b</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="CITEREFMahley2016" class="citation journal cs1">Mahley RW (2016). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4942259">"Central Nervous System Lipoproteins: ApoE and Regulation of Cholesterol Metabolism"</a>. <i>Arterioscler Thromb Vasc Biol</i>. <b>36</b> (7): 1305–15. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1161%2FATVBAHA.116.307023">10.1161/ATVBAHA.116.307023</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/PMC4942259">4942259</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/27174096">27174096</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Arterioscler+Thromb+Vasc+Biol&rft.atitle=Central+Nervous+System+Lipoproteins%3A+ApoE+and+Regulation+of+Cholesterol+Metabolism.&rft.volume=36&rft.issue=7&rft.pages=1305-15&rft.date=2016&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4942259%23id-name%3DPMC&rft_id=info%3Apmid%2F27174096&rft_id=info%3Adoi%2F10.1161%2FATVBAHA.116.307023&rft.aulast=Mahley&rft.aufirst=RW&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4942259&rfr_id=info%3Asid%2Fen.wikipedia.org%3A24S-Hydroxycholesterol" class="Z3988"></span></span> </li> <li id="cite_note-pmid13105923-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid13105923_2-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFErcoliDi_FriscoDe_Ruggieri1953" class="citation journal cs1">Ercoli A, Di Frisco S, De Ruggieri P (1953). "Isolation, constitution and biological significance of cerebrosterol, a companion of cholesterol in the horse brain". <i>Boll Soc Ital Biol Sper</i>. <b>29</b> (4): 494–7. <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/13105923">13105923</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Boll+Soc+Ital+Biol+Sper&rft.atitle=Isolation%2C+constitution+and+biological+significance+of+cerebrosterol%2C+a+companion+of+cholesterol+in+the+horse+brain.&rft.volume=29&rft.issue=4&rft.pages=494-7&rft.date=1953&rft_id=info%3Apmid%2F13105923&rft.aulast=Ercoli&rft.aufirst=A&rft.au=Di+Frisco%2C+S&rft.au=De+Ruggieri%2C+P&rfr_id=info%3Asid%2Fen.wikipedia.org%3A24S-Hydroxycholesterol" class="Z3988"></span></span> </li> <li id="cite_note-pmid13140512-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid13140512_3-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDi_FriscoDe_RuggieriErcoli1953" class="citation journal cs1">Di Frisco S, De Ruggieri P, Ercoli A (1953). "Isolation of cerebrosterol from human brain". <i>Boll Soc Ital Biol Sper</i>. <b>29</b> (7): 1351–2. <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/13140512">13140512</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Boll+Soc+Ital+Biol+Sper&rft.atitle=Isolation+of+cerebrosterol+from+human+brain.&rft.volume=29&rft.issue=7&rft.pages=1351-2&rft.date=1953&rft_id=info%3Apmid%2F13140512&rft.aulast=Di+Frisco&rft.aufirst=S&rft.au=De+Ruggieri%2C+P&rft.au=Ercoli%2C+A&rfr_id=info%3Asid%2Fen.wikipedia.org%3A24S-Hydroxycholesterol" class="Z3988"></span></span> </li> <li id="cite_note-pmid12686551-4"><span class="mw-cite-backlink">^ <a href="#cite_ref-pmid12686551_4-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid12686551_4-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLundXieKottiTurley2003" class="citation journal cs1">Lund EG, Xie C, Kotti T, Turley SD, Dietschy JM, Russell DW (2003). <a rel="nofollow" class="external text" href="https://doi.org/10.1074%2Fjbc.M303415200">"Knockout of the cholesterol 24-hydroxylase gene in mice reveals a brain-specific mechanism of cholesterol turnover"</a>. <i>J Biol Chem</i>. <b>278</b> (25): 22980–8. <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/10.1074%2Fjbc.M303415200">10.1074/jbc.M303415200</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/12686551">12686551</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J+Biol+Chem&rft.atitle=Knockout+of+the+cholesterol+24-hydroxylase+gene+in+mice+reveals+a+brain-specific+mechanism+of+cholesterol+turnover.&rft.volume=278&rft.issue=25&rft.pages=22980-8&rft.date=2003&rft_id=info%3Adoi%2F10.1074%2Fjbc.M303415200&rft_id=info%3Apmid%2F12686551&rft.aulast=Lund&rft.aufirst=EG&rft.au=Xie%2C+C&rft.au=Kotti%2C+T&rft.au=Turley%2C+SD&rft.au=Dietschy%2C+JM&rft.au=Russell%2C+DW&rft_id=https%3A%2F%2Fdoi.org%2F10.1074%252Fjbc.M303415200&rfr_id=info%3Asid%2Fen.wikipedia.org%3A24S-Hydroxycholesterol" class="Z3988"></span></span> </li> <li id="cite_note-pmid20211758-5"><span class="mw-cite-backlink">^ <a href="#cite_ref-pmid20211758_5-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid20211758_5-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWangKumarCrumbleyGriffin2010" class="citation journal cs1">Wang Y, Kumar N, Crumbley C, Griffin PR, Burris TP (2010). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2886165">"A second class of nuclear receptors for oxysterols: Regulation of RORalpha and RORgamma activity by 24S-hydroxycholesterol (cerebrosterol)"</a>. <i>Biochim Biophys Acta</i>. <b>1801</b> (8): 917–23. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.bbalip.2010.02.012">10.1016/j.bbalip.2010.02.012</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/PMC2886165">2886165</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/20211758">20211758</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Biochim+Biophys+Acta&rft.atitle=A+second+class+of+nuclear+receptors+for+oxysterols%3A+Regulation+of+RORalpha+and+RORgamma+activity+by+24S-hydroxycholesterol+%28cerebrosterol%29.&rft.volume=1801&rft.issue=8&rft.pages=917-23&rft.date=2010&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2886165%23id-name%3DPMC&rft_id=info%3Apmid%2F20211758&rft_id=info%3Adoi%2F10.1016%2Fj.bbalip.2010.02.012&rft.aulast=Wang&rft.aufirst=Y&rft.au=Kumar%2C+N&rft.au=Crumbley%2C+C&rft.au=Griffin%2C+PR&rft.au=Burris%2C+TP&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2886165&rfr_id=info%3Asid%2Fen.wikipedia.org%3A24S-Hydroxycholesterol" class="Z3988"></span></span> </li> <li id="cite_note-pmid17393206-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid17393206_6-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBjörkhem2007" class="citation journal cs1">Björkhem I (2007). "Rediscovery of cerebrosterol". <i>Lipids</i>. <b>42</b> (1): 5–14. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2Fs11745-006-1003-2">10.1007/s11745-006-1003-2</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/17393206">17393206</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:4005673">4005673</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Lipids&rft.atitle=Rediscovery+of+cerebrosterol.&rft.volume=42&rft.issue=1&rft.pages=5-14&rft.date=2007&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A4005673%23id-name%3DS2CID&rft_id=info%3Apmid%2F17393206&rft_id=info%3Adoi%2F10.1007%2Fs11745-006-1003-2&rft.aulast=Bj%C3%B6rkhem&rft.aufirst=I&rfr_id=info%3Asid%2Fen.wikipedia.org%3A24S-Hydroxycholesterol" class="Z3988"></span></span> </li> <li id="cite_note-pmid16866909-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid16866909_7-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLütjohann2006" class="citation journal cs1">Lütjohann D (2006). "Cholesterol metabolism in the brain: importance of 24S-hydroxylation". <i>Acta Neurol Scand Suppl</i>. <b>185</b>: 33–42. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1600-0404.2006.00683.x">10.1111/j.1600-0404.2006.00683.x</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16866909">16866909</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:44809894">44809894</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Acta+Neurol+Scand+Suppl&rft.atitle=Cholesterol+metabolism+in+the+brain%3A+importance+of+24S-hydroxylation.&rft.volume=185&rft.pages=33-42&rft.date=2006&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A44809894%23id-name%3DS2CID&rft_id=info%3Apmid%2F16866909&rft_id=info%3Adoi%2F10.1111%2Fj.1600-0404.2006.00683.x&rft.aulast=L%C3%BCtjohann&rft.aufirst=D&rfr_id=info%3Asid%2Fen.wikipedia.org%3A24S-Hydroxycholesterol" class="Z3988"></span></span> </li> <li id="cite_note-pmid20053345-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid20053345_8-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCartagenaBurnsRebeck2010" class="citation journal cs1">Cartagena CM, Burns MP, Rebeck GW (2010). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2826556">"24S-hydroxycholesterol effects on lipid metabolism genes are modeled in traumatic brain injury"</a>. <i>Brain Res</i>. <b>1319</b>: 1–12. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.brainres.2009.12.080">10.1016/j.brainres.2009.12.080</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/PMC2826556">2826556</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/20053345">20053345</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Brain+Res&rft.atitle=24S-hydroxycholesterol+effects+on+lipid+metabolism+genes+are+modeled+in+traumatic+brain+injury.&rft.volume=1319&rft.pages=1-12&rft.date=2010&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2826556%23id-name%3DPMC&rft_id=info%3Apmid%2F20053345&rft_id=info%3Adoi%2F10.1016%2Fj.brainres.2009.12.080&rft.aulast=Cartagena&rft.aufirst=CM&rft.au=Burns%2C+MP&rft.au=Rebeck%2C+GW&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2826556&rfr_id=info%3Asid%2Fen.wikipedia.org%3A24S-Hydroxycholesterol" class="Z3988"></span></span> </li> <li id="cite_note-pmid24174662-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid24174662_9-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPaulDohertyRobichaudBelfort2013" class="citation journal cs1">Paul SM, Doherty JJ, Robichaud AJ, Belfort GM, Chow BY, Hammond RS, Crawford DC, Linsenbardt AJ, Shu HJ, Izumi Y, Mennerick SJ, Zorumski CF (October 2013). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3812502">"The major brain cholesterol metabolite 24(S)-hydroxycholesterol is a potent allosteric modulator of N-methyl-D-aspartate receptors"</a>. <i><a href="/wiki/The_Journal_of_Neuroscience" title="The Journal of Neuroscience">The Journal of Neuroscience</a></i>. <b>33</b> (44): 17290–300. <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.2619-13.2013">10.1523/JNEUROSCI.2619-13.2013</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/PMC3812502">3812502</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/24174662">24174662</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Neuroscience&rft.atitle=The+major+brain+cholesterol+metabolite+24%28S%29-hydroxycholesterol+is+a+potent+allosteric+modulator+of+N-methyl-D-aspartate+receptors&rft.volume=33&rft.issue=44&rft.pages=17290-300&rft.date=2013-10&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3812502%23id-name%3DPMC&rft_id=info%3Apmid%2F24174662&rft_id=info%3Adoi%2F10.1523%2FJNEUROSCI.2619-13.2013&rft.aulast=Paul&rft.aufirst=SM&rft.au=Doherty%2C+JJ&rft.au=Robichaud%2C+AJ&rft.au=Belfort%2C+GM&rft.au=Chow%2C+BY&rft.au=Hammond%2C+RS&rft.au=Crawford%2C+DC&rft.au=Linsenbardt%2C+AJ&rft.au=Shu%2C+HJ&rft.au=Izumi%2C+Y&rft.au=Mennerick%2C+SJ&rft.au=Zorumski%2C+CF&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3812502&rfr_id=info%3Asid%2Fen.wikipedia.org%3A24S-Hydroxycholesterol" class="Z3988"></span></span> </li> <li id="cite_note-pmid25628343-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid25628343_10-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSunLinsenbardtEmnettEisenman2016" class="citation journal cs1">Sun MY, Linsenbardt AJ, Emnett CM, Eisenman LN, Izumi Y, Zorumski CF, Mennerick S (2016). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4821654">"24(S)-Hydroxycholesterol as a Modulator of Neuronal Signaling and Survival"</a>. <i>Neuroscientist</i>. <b>22</b> (2): 132–44. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1177%2F1073858414568122">10.1177/1073858414568122</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/PMC4821654">4821654</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/25628343">25628343</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Neuroscientist&rft.atitle=24%28S%29-Hydroxycholesterol+as+a+Modulator+of+Neuronal+Signaling+and+Survival.&rft.volume=22&rft.issue=2&rft.pages=132-44&rft.date=2016&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4821654%23id-name%3DPMC&rft_id=info%3Apmid%2F25628343&rft_id=info%3Adoi%2F10.1177%2F1073858414568122&rft.aulast=Sun&rft.aufirst=MY&rft.au=Linsenbardt%2C+AJ&rft.au=Emnett%2C+CM&rft.au=Eisenman%2C+LN&rft.au=Izumi%2C+Y&rft.au=Zorumski%2C+CF&rft.au=Mennerick%2C+S&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4821654&rfr_id=info%3Asid%2Fen.wikipedia.org%3A24S-Hydroxycholesterol" class="Z3988"></span></span> </li> <li id="cite_note-pmid28346482-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid28346482_11-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSunTaylorZorumskiMennerick2017" class="citation journal cs1">Sun MY, Taylor A, Zorumski CF, Mennerick S (2017). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5367825">"24S-hydroxycholesterol and 25-hydroxycholesterol differentially impact hippocampal neuronal survival following oxygen-glucose deprivation"</a>. <i>PLOS ONE</i>. <b>12</b> (3): e0174416. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2017PLoSO..1274416S">2017PLoSO..1274416S</a>. <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/10.1371%2Fjournal.pone.0174416">10.1371/journal.pone.0174416</a></span>. <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/PMC5367825">5367825</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/28346482">28346482</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=PLOS+ONE&rft.atitle=24S-hydroxycholesterol+and+25-hydroxycholesterol+differentially+impact+hippocampal+neuronal+survival+following+oxygen-glucose+deprivation.&rft.volume=12&rft.issue=3&rft.pages=e0174416&rft.date=2017&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5367825%23id-name%3DPMC&rft_id=info%3Apmid%2F28346482&rft_id=info%3Adoi%2F10.1371%2Fjournal.pone.0174416&rft_id=info%3Abibcode%2F2017PLoSO..1274416S&rft.aulast=Sun&rft.aufirst=MY&rft.au=Taylor%2C+A&rft.au=Zorumski%2C+CF&rft.au=Mennerick%2C+S&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5367825&rfr_id=info%3Asid%2Fen.wikipedia.org%3A24S-Hydroxycholesterol" class="Z3988"></span></span> </li> <li id="cite_note-pmid23041502-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid23041502_12-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLeoniCaccia2013" class="citation journal cs1">Leoni V, Caccia C (2013). "24S-hydroxycholesterol in plasma: a marker of cholesterol turnover in neurodegenerative diseases". <i>Biochimie</i>. <b>95</b> (3): 595–612. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.biochi.2012.09.025">10.1016/j.biochi.2012.09.025</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/23041502">23041502</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Biochimie&rft.atitle=24S-hydroxycholesterol+in+plasma%3A+a+marker+of+cholesterol+turnover+in+neurodegenerative+diseases.&rft.volume=95&rft.issue=3&rft.pages=595-612&rft.date=2013&rft_id=info%3Adoi%2F10.1016%2Fj.biochi.2012.09.025&rft_id=info%3Apmid%2F23041502&rft.aulast=Leoni&rft.aufirst=V&rft.au=Caccia%2C+C&rfr_id=info%3Asid%2Fen.wikipedia.org%3A24S-Hydroxycholesterol" class="Z3988"></span></span> </li> <li id="cite_note-pmid25539717-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid25539717_13-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBandaruHaughey2014" class="citation journal cs1">Bandaru VV, Haughey NJ (2014). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4304132">"Quantitative detection of free 24S-hydroxycholesterol, and 27-hydroxycholesterol from human serum"</a>. <i>BMC Neurosci</i>. <b>15</b>: 137. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1186%2Fs12868-014-0137-z">10.1186/s12868-014-0137-z</a></span>. <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/PMC4304132">4304132</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/25539717">25539717</a>.</cite><span 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title="Cholesterol">Cholesterol</a></li> <li><a href="/wiki/22R-Hydroxycholesterol" title="22R-Hydroxycholesterol">22<i>R</i>-Hydroxycholesterol</a></li> <li><a href="/wiki/20%CE%B1,22R-Dihydroxycholesterol" title="20α,22R-Dihydroxycholesterol">20α,22<i>R</i>-Dihydroxycholesterol</a></li> <li><a href="/wiki/Pregnenolone" title="Pregnenolone">Pregnenolone</a></li> <li><a href="/w/index.php?title=11%CE%B2-Hydroxypregnenolone&action=edit&redlink=1" class="new" title="11β-Hydroxypregnenolone (page does not exist)">11β-Hydroxypregnenolone</a></li> <li><a href="/wiki/17%CE%B1-Hydroxypregnenolone" title="17α-Hydroxypregnenolone">17α-Hydroxypregnenolone</a></li> <li><a href="/wiki/21-Hydroxypregnenolone" title="21-Hydroxypregnenolone">21-Hydroxypregnenolone</a></li> <li><a href="/w/index.php?title=17%CE%B1,21-Dihydroxypregnenolone&action=edit&redlink=1" class="new" title="17α,21-Dihydroxypregnenolone (page does not exist)">17α,21-Dihydroxypregnenolone</a></li> <li><a href="/w/index.php?title=11%CE%B2,17%CE%B1,21-Trihydroxypregnenolone&action=edit&redlink=1" class="new" title="11β,17α,21-Trihydroxypregnenolone (page does not exist)">11β,17α,21-Trihydroxypregnenolone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Corticosteroid" title="Corticosteroid">Corticosteroids</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Glucocorticoid" title="Glucocorticoid">Glucocorticoids</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Tetrahydrocorticosterone" title="Tetrahydrocorticosterone">3α,5α-Tetrahydrocorticosterone</a></li> <li><a href="/wiki/5%CE%B1-Dihydrocorticosterone" title="5α-Dihydrocorticosterone">5α-Dihydrocorticosterone</a></li> <li><a href="/wiki/11-Deoxycorticosterone" title="11-Deoxycorticosterone">11-Deoxycorticosterone</a></li> <li><a href="/wiki/11-Deoxycortisol" title="11-Deoxycortisol">11-Deoxycortisol</a></li> <li><a href="/wiki/11-Ketoprogesterone" title="11-Ketoprogesterone">11-Ketoprogesterone</a></li> <li><a href="/wiki/21-Deoxycortisol" title="21-Deoxycortisol">21-Deoxycortisol</a></li> <li><a href="/wiki/21-Deoxycortisone" title="21-Deoxycortisone">21-Deoxycortisone</a></li> <li><a href="/wiki/Corticosterone" title="Corticosterone">Corticosterone</a></li> <li><a href="/wiki/Cortisol" title="Cortisol">Cortisol</a></li> <li><a href="/wiki/Cortisone" title="Cortisone">Cortisone</a></li> <li><a href="/wiki/17%CE%B1-Hydroxypregnenolone" title="17α-Hydroxypregnenolone">17α-Hydroxypregnenolone</a></li> <li><a href="/wiki/17%CE%B1-Hydroxyprogesterone" title="17α-Hydroxyprogesterone">17α-Hydroxyprogesterone</a></li> <li><a href="/wiki/Pregnenolone" title="Pregnenolone">Pregnenolone</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li></ul> <ul><li><i>Metabolites:</i> <a href="/wiki/5%CE%B1-Dihydrocortisol" title="5α-Dihydrocortisol">5α-Dihydrocortisol</a></li> <li><a href="/w/index.php?title=3%CE%B1,5%CE%B1-Tetrahydrocortisol&action=edit&redlink=1" class="new" title="3α,5α-Tetrahydrocortisol (page does not exist)">3α,5α-Tetrahydrocortisol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Mineralocorticoid" title="Mineralocorticoid">Mineralocorticoids</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/5%CE%B1-Dihydroaldosterone" title="5α-Dihydroaldosterone">5α-Dihydroaldosterone</a></li> <li><a href="/wiki/11-Dehydrocorticosterone" title="11-Dehydrocorticosterone">11-Dehydrocorticosterone (11-oxocorticosterone, 17-deoxycortisone)</a></li> <li><a href="/wiki/11-Deoxycortisol" title="11-Deoxycortisol">11-Deoxycortisol</a></li> <li><a href="/wiki/11-Deoxycorticosterone" title="11-Deoxycorticosterone">11-Deoxycorticosterone</a></li> <li><a href="/wiki/11%CE%B2-Hydroxyprogesterone" title="11β-Hydroxyprogesterone">11β-Hydroxyprogesterone (21-deoxycorticosterone)</a></li> <li><a href="/wiki/18-Hydroxy-11-deoxycorticosterone" title="18-Hydroxy-11-deoxycorticosterone">18-Hydroxy-11-deoxycorticosterone</a></li> <li><a href="/wiki/18-Hydroxycorticosterone" title="18-Hydroxycorticosterone">18-Hydroxycorticosterone</a></li> <li><a href="/w/index.php?title=18-Hydroxyprogesterone&action=edit&redlink=1" class="new" title="18-Hydroxyprogesterone (page does not exist)">18-Hydroxyprogesterone</a></li> <li><a href="/wiki/Aldosterone" title="Aldosterone">Aldosterone</a></li> <li><a href="/wiki/Corticosterone" title="Corticosterone">Corticosterone</a></li> <li><a href="/wiki/Cortisol" title="Cortisol">Cortisol</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/Sex_steroid" class="mw-redirect" title="Sex steroid">Sex steroids</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Androgen" title="Androgen">Androgens</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/11-Ketodihydrotestosterone" title="11-Ketodihydrotestosterone">11-Ketodihydrotestosterone</a></li> <li><a href="/wiki/11-Ketotestosterone" title="11-Ketotestosterone">11-Ketotestosterone</a></li> <li><a href="/wiki/7%CE%B2-Hydroxyepiandrosterone" title="7β-Hydroxyepiandrosterone">7β-Hydroxyepiandrosterone</a></li> <li><a href="/wiki/11%CE%B2-Hydroxyandrostenedione" title="11β-Hydroxyandrostenedione">11β-Hydroxyandrostenedione</a></li> <li><a href="/wiki/Adrenosterone" title="Adrenosterone">Adrenosterone (11-ketoandrostenedione)</a></li> <li><a href="/wiki/Androstenediol" title="Androstenediol">Androstenediol</a></li> <li><a href="/wiki/Androstenedione" title="Androstenedione">Androstenedione</a></li> <li><a href="/wiki/Androsterone" title="Androsterone">Androsterone</a></li> <li><a href="/wiki/Dehydroandrosterone" title="Dehydroandrosterone">Dehydroandrosterone</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a></li> <li><a href="/wiki/Dehydroepiandrosterone_sulfate" title="Dehydroepiandrosterone sulfate">DHEA sulfate</a></li> <li><a href="/wiki/Dihydrotestosterone" title="Dihydrotestosterone">Dihydrotestosterone</a></li> <li><a href="/wiki/Epiandrosterone" title="Epiandrosterone">Epiandrosterone</a></li> <li><a href="/wiki/Epitestosterone" title="Epitestosterone">Epitestosterone</a></li> <li><a href="/wiki/16%CE%B1-Hydroxyandrostenedione" title="16α-Hydroxyandrostenedione">16α-Hydroxyandrostenedione</a></li> <li><a href="/wiki/16-Hydroxydehydroepiandrosterone" class="mw-redirect" title="16-Hydroxydehydroepiandrosterone">16α-Hydroxy-DHEA</a></li> <li><a href="/wiki/16-Hydroxydehydroepiandrosterone_sulfate" class="mw-redirect" title="16-Hydroxydehydroepiandrosterone sulfate">16α-Hydroxy-DHEA sulfate</a></li> <li><a href="/wiki/Testosterone" title="Testosterone">Testosterone</a></li></ul> <ul><li><i>Metabolites:</i> <a href="/wiki/3%CE%B1-Androstanediol" title="3α-Androstanediol">3α-Androstanediol</a></li> <li><a href="/wiki/3%CE%B1-Androstanediol_glucuronide" class="mw-redirect" title="3α-Androstanediol glucuronide">3α-Androstanediol glucuronide</a></li> <li><a href="/wiki/3%CE%B2-Androstanediol" title="3β-Androstanediol">3β-Androstanediol</a></li> <li><a href="/wiki/5%CE%B2-Dihydrotestosterone" title="5β-Dihydrotestosterone">5β-Dihydrotestosterone</a></li> <li><a href="/wiki/3%CE%B1-Etiocholanediol" title="3α-Etiocholanediol">3α-Etiocholanediol</a></li> <li><a href="/wiki/3%CE%B2-Etiocholanediol" title="3β-Etiocholanediol">3β-Etiocholanediol</a></li> <li><a href="/w/index.php?title=Androstanetriol&action=edit&redlink=1" class="new" title="Androstanetriol (page does not exist)">Androstanetriols</a></li> <li><a href="/wiki/Androstenediol_sulfate" title="Androstenediol sulfate">Androstenediol sulfate</a></li> <li><a href="/wiki/Androstenetriol" title="Androstenetriol">Androstenetriol</a></li> <li><a href="/wiki/Androsterone_glucuronide" title="Androsterone glucuronide">Androsterone glucuronide</a></li> <li><a href="/wiki/Androsterone_sulfate" title="Androsterone sulfate">Androsterone sulfate</a></li> <li><a href="/w/index.php?title=Dihydrotestosterone_glucuronide&action=edit&redlink=1" class="new" title="Dihydrotestosterone glucuronide (page does not exist)">Dihydrotestosterone glucuronide</a></li> <li><a href="/w/index.php?title=Dihydrotestosterone_sulfate&action=edit&redlink=1" class="new" title="Dihydrotestosterone sulfate (page does not exist)">Dihydrotestosterone sulfate</a></li> <li><a href="/wiki/Etiocholanedione" title="Etiocholanedione">Etiocholanedione</a></li> <li><a href="/wiki/Etiocholanolone" title="Etiocholanolone">Etiocholanolone</a></li> <li><a href="/wiki/Etiocholanolone_glucuronide" title="Etiocholanolone glucuronide">Etiocholanolone glucuronide</a></li> <li><a href="/wiki/Epietiocholanolone" title="Epietiocholanolone">Epietiocholanolone</a></li> <li><a href="/wiki/Testosterone_glucuronide" title="Testosterone glucuronide">Testosterone glucuronide</a></li> <li><a href="/wiki/Testosterone_sulfate" title="Testosterone sulfate">Testosterone sulfate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Estrogen" title="Estrogen">Estrogens</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><i>Estranes:</i> <a href="/wiki/Estetrol" title="Estetrol">Estetrol</a></li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a></li> <li><a href="/wiki/Estrone" title="Estrone">Estrone</a></li> <li><a href="/wiki/Estriol" title="Estriol">Estriol</a></li> <li><a href="/wiki/17%CE%B1-Estradiol" title="17α-Estradiol">17α-Estradiol</a></li> <li><a href="/wiki/Epiestriol" title="Epiestriol">16β-Epiestriol (16β-hydroxyestradiol)</a></li> <li><a href="/wiki/17%CE%B1-Epiestriol" title="17α-Epiestriol">17α-Epiestriol (16α-hydroxy-17α-estradiol)</a></li> <li><a href="/wiki/16%CE%B2,17%CE%B1-Epiestriol" title="16β,17α-Epiestriol">16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)</a></li> <li><a href="/wiki/2-Hydroxyestradiol" title="2-Hydroxyestradiol">2-Hydroxyestradiol</a></li> <li><a href="/wiki/2-Hydroxyestriol" title="2-Hydroxyestriol">2-Hydroxyestriol</a></li> <li><a href="/wiki/2-Hydroxyestrone" title="2-Hydroxyestrone">2-Hydroxyestrone</a></li> <li><a href="/wiki/4-Hydroxyestradiol" title="4-Hydroxyestradiol">4-Hydroxyestradiol</a></li> <li><a href="/wiki/4-Hydroxyestriol" title="4-Hydroxyestriol">4-Hydroxyestriol</a></li> <li><a href="/wiki/4-Hydroxyestrone" title="4-Hydroxyestrone">4-Hydroxyestrone</a></li> <li><a href="/wiki/4-Methoxyestradiol" title="4-Methoxyestradiol">4-Methoxyestradiol</a></li> <li><a href="/wiki/4-Methoxyestrone" title="4-Methoxyestrone">4-Methoxyestrone</a></li> <li><a href="/wiki/16%CE%B1-Hydroxyestrone" title="16α-Hydroxyestrone">16α-Hydroxyestrone</a></li> <li><a href="/wiki/16%CE%B2-Hydroxyestrone" title="16β-Hydroxyestrone">16β-Hydroxyestrone</a></li> <li><a href="/wiki/16-Ketoestradiol" title="16-Ketoestradiol">16-Ketoestradiol</a></li> <li><a href="/wiki/16-Ketoestrone" title="16-Ketoestrone">16-Ketoestrone</a></li></ul> <ul><li><i>Others:</i> <a href="/wiki/27-Hydroxycholesterol" title="27-Hydroxycholesterol">27-Hydroxycholesterol</a></li> <li><a href="/wiki/3%CE%B1-Androstanediol" title="3α-Androstanediol">3α-Androstanediol</a></li> <li><a href="/wiki/3%CE%B2-Androstanediol" title="3β-Androstanediol">3β-Androstanediol</a></li> <li><a href="/wiki/4-Androstenedione" class="mw-redirect" title="4-Androstenedione">4-Androstenedione</a></li> <li><a href="/wiki/5-Androstenediol" class="mw-redirect" title="5-Androstenediol">5-Androstenediol</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a></li> <li><a href="/wiki/Dehydroepiandrosterone_sulfate" title="Dehydroepiandrosterone sulfate">DHEA sulfate</a></li> <li><a href="/wiki/7-Keto-DHEA" title="7-Keto-DHEA">7-Keto-DHEA</a></li> <li><a href="/wiki/7%CE%B1-Hydroxy-DHEA" title="7α-Hydroxy-DHEA">7α-Hydroxy-DHEA</a></li> <li><a href="/wiki/16-Hydroxydehydroepiandrosterone" class="mw-redirect" title="16-Hydroxydehydroepiandrosterone">16α-Hydroxy-DHEA</a></li></ul> <ul><li><i>Metabolites:</i> <a href="/wiki/2-Methoxyestradiol" title="2-Methoxyestradiol">2-Methoxyestradiol</a></li> <li><a href="/wiki/2-Methoxyestrone" title="2-Methoxyestrone">2-Methoxyestrone</a></li> <li><a href="/wiki/2-Methoxyestriol" title="2-Methoxyestriol">2-Methoxyestriol</a></li> <li><a href="/wiki/4-Methoxyestriol" title="4-Methoxyestriol">4-Methoxyestriol</a></li> <li><a href="/wiki/Estradiol_disulfate" title="Estradiol disulfate">Estradiol disulfate</a></li> <li><a href="/wiki/Estradiol_glucuronide" title="Estradiol glucuronide">Estradiol glucuronide</a></li> <li><a href="/wiki/Estradiol_3-glucuronide" title="Estradiol 3-glucuronide">Estradiol 3-glucuronide</a></li> <li><a href="/wiki/Estradiol_3-glucuronide_17%CE%B2-sulfate" title="Estradiol 3-glucuronide 17β-sulfate">Estradiol 3-glucuronide 17β-sulfate</a></li> <li><a href="/wiki/Estradiol_sulfate" title="Estradiol sulfate">Estradiol sulfate</a></li> <li><a href="/wiki/Estradiol_17%CE%B2-sulfate" title="Estradiol 17β-sulfate">Estradiol 17β-sulfate</a></li> <li><a href="/wiki/Estrone_glucuronide" title="Estrone glucuronide">Estrone glucuronide</a></li> <li><a href="/wiki/Estrone_sulfate" title="Estrone sulfate">Estrone sulfate</a></li> <li><a href="/wiki/Estriol_glucuronide" title="Estriol glucuronide">Estriol glucuronide</a></li> <li><a href="/wiki/Estriol_sulfate" title="Estriol sulfate">Estriol sulfate</a></li> <li><a href="/wiki/Lipoidal_estradiol" title="Lipoidal estradiol">Lipoidal estradiol</a> (e.g., <a href="/wiki/Estradiol_stearate" title="Estradiol stearate">estradiol stearate</a>, <a href="/wiki/Estradiol_palmitate" title="Estradiol palmitate">estradiol palmitate</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Progestogen" title="Progestogen">Progestogens</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li> <li><a href="/wiki/16%CE%B1-Hydroxyprogesterone" title="16α-Hydroxyprogesterone">16α-Hydroxyprogesterone</a></li> <li><a href="/wiki/17%CE%B1-Hydroxyprogesterone" title="17α-Hydroxyprogesterone">17α-Hydroxyprogesterone</a></li> <li><a href="/wiki/20%CE%B1-Dihydroprogesterone" title="20α-Dihydroprogesterone">20α-Dihydroprogesterone</a></li> <li><a href="/wiki/20%CE%B2-Dihydroprogesterone" title="20β-Dihydroprogesterone">20β-Dihydroprogesterone</a></li> <li><a href="/wiki/5%CE%B1-Dihydroprogesterone" title="5α-Dihydroprogesterone">5α-Dihydroprogesterone</a></li> <li><a href="/wiki/11-Deoxycorticosterone" title="11-Deoxycorticosterone">11-Deoxycorticosterone</a></li> <li><a href="/wiki/Dihydrodeoxycorticosterone" title="Dihydrodeoxycorticosterone">5α-DHDOC</a></li></ul> <ul><li><i>Metabolites:</i> <a href="/wiki/Allopregnanediol" title="Allopregnanediol">Allopregnanediol</a></li> <li><a href="/wiki/Pregnanediol" title="Pregnanediol">Pregnanediol</a></li> <li><a href="/wiki/Pregnanediol_glucuronide" title="Pregnanediol glucuronide">Pregnanediol glucuronide</a></li> <li><a href="/wiki/Pregnanetriol" title="Pregnanetriol">Pregnanetriol</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/Neuroactive_steroid" class="mw-redirect" title="Neuroactive steroid">Neurosteroids</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Cholestanes:</i> <a href="/wiki/24S-hydroxycholesterol" class="mw-redirect" title="24S-hydroxycholesterol">24<i>S</i>-Hydroxycholesterol</a></li> <li><a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a></li></ul> <ul><li><i>Pregnanes:</i> <a href="/wiki/3%CE%B1-Dihydroprogesterone" title="3α-Dihydroprogesterone">3α-Dihydroprogesterone</a></li> <li><a href="/wiki/3%CE%B2-Dihydroprogesterone" title="3β-Dihydroprogesterone">3β-Dihydroprogesterone</a></li> <li><a href="/wiki/5%CE%B1-Dihydrocorticosterone" title="5α-Dihydrocorticosterone">5α-Dihydrocorticosterone</a></li> <li><a href="/wiki/5%CE%B1-Dihydroprogesterone" title="5α-Dihydroprogesterone">5α-Dihydroprogesterone</a></li> <li><a href="/wiki/5%CE%B2-Dihydroprogesterone" title="5β-Dihydroprogesterone">5β-Dihydroprogesterone</a></li> <li><a href="/wiki/Allopregnanolone" title="Allopregnanolone">Allopregnanolone</a></li> <li><a href="/wiki/Corticosterone" title="Corticosterone">Corticosterone</a></li> <li><a href="/wiki/Dihydrocorticosterone" class="mw-redirect" title="Dihydrocorticosterone">DHC</a></li> <li><a href="/wiki/Dihydrodeoxycorticosterone" title="Dihydrodeoxycorticosterone">DHDOC</a></li> <li><a href="/wiki/11-Deoxycorticosterone" title="11-Deoxycorticosterone">11-Deoxycorticosterone</a></li> <li><a href="/wiki/Epipregnanolone" title="Epipregnanolone">Epipregnanolone</a></li> <li><a href="/wiki/Isopregnanolone" title="Isopregnanolone">Isopregnanolone</a></li> <li><a href="/wiki/Pregnanolone" title="Pregnanolone">Pregnanolone</a></li> <li><a href="/wiki/Pregnenolone" title="Pregnenolone">Pregnenolone</a></li> <li><a href="/wiki/Pregnenolone_sulfate" title="Pregnenolone sulfate">Pregnenolone sulfate</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li> <li><a href="/wiki/Tetrahydrocorticosterone" title="Tetrahydrocorticosterone">THB</a></li> <li><a href="/wiki/Tetrahydrodeoxycorticosterone" title="Tetrahydrodeoxycorticosterone">THDOC</a></li></ul> <ul><li><i>Androstanes:</i> <a href="/wiki/3%CE%B1-Androstanediol" title="3α-Androstanediol">3α-Androstanediol</a></li> <li><a href="/wiki/3%CE%B1-Androstenol" class="mw-redirect" title="3α-Androstenol">3α-Androstenol</a></li> <li><a href="/wiki/7-Keto-DHEA" title="7-Keto-DHEA">7-Keto-DHEA</a></li> <li><a href="/wiki/7%CE%B1-Hydroxy-DHEA" title="7α-Hydroxy-DHEA">7α-Hydroxy-DHEA</a></li> <li><a href="/wiki/7%CE%B2-Hydroxy-DHEA" title="7β-Hydroxy-DHEA">7β-Hydroxy-DHEA</a></li> <li><a href="/wiki/7%CE%B1-Hydroxyepiandrosterone" title="7α-Hydroxyepiandrosterone">7α-Hydroxyepiandrosterone</a></li> <li><a href="/wiki/7%CE%B2-Hydroxyepiandrosterone" title="7β-Hydroxyepiandrosterone">7β-Hydroxyepiandrosterone</a></li> <li><a href="/wiki/Androsterone" title="Androsterone">Androsterone</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a></li> <li><a href="/wiki/Dehydroepiandrosterone_sulfate" title="Dehydroepiandrosterone sulfate">DHEA sulfate</a></li> <li><a href="/wiki/Etiocholanolone" title="Etiocholanolone">Etiocholanolone</a></li></ul> <ul><li><b><a href="/wiki/Pheromone" title="Pheromone">Pheromones</a>:</b> <a href="/wiki/3%CE%B1-Androstenol" class="mw-redirect" title="3α-Androstenol">3α-Androstenol</a></li> <li><a href="/wiki/3%CE%B2-Androstenol" title="3β-Androstenol">3β-Androstenol</a></li> <li><a href="/wiki/Androstadienol" title="Androstadienol">Androstadienol</a></li> <li><a href="/wiki/Androstadienone" title="Androstadienone">Androstadienone</a></li> <li><a href="/wiki/Androstenone" title="Androstenone">Androstenone</a></li> <li><a href="/wiki/Androsterone" title="Androsterone">Androsterone</a></li> <li><a href="/wiki/Estratetraenol" title="Estratetraenol">Estratetraenol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</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><b><a href="/wiki/Vitamin_D" title="Vitamin D">Vitamin D</a>:</b> <a href="/wiki/7-Dehydrocholesterol" title="7-Dehydrocholesterol">7-Dehydrocholesterol</a></li> <li><a href="/wiki/Calcifediol" title="Calcifediol">Calcidiol/Calcifediol</a></li> <li><a href="/wiki/Calcitriol" title="Calcitriol">Calcitriol</a></li> <li><a href="/wiki/Cholecalciferol" title="Cholecalciferol">Cholecalciferol</a></li></ul> <ul><li><b>Others:</b> <a href="/wiki/7%CE%B1-Hydroxycholesterol" title="7α-Hydroxycholesterol">7α-Hydroxycholesterol</a></li> <li><a href="/wiki/11%CE%B1-Hydroxyprogesterone" title="11α-Hydroxyprogesterone">11α-Hydroxyprogesterone</a></li> <li><a href="/wiki/11%CE%B2-Hydroxyprogesterone" title="11β-Hydroxyprogesterone">11β-Hydroxyprogesterone</a></li> <li><a href="/wiki/Cholesterol_sulfate" title="Cholesterol sulfate">Cholesterol sulfate</a></li></ul> </div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" 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