{{Use dmy dates|date=December 2023}}{{cs1 config|name-list-style=vanc}}{{chembox |ImageFile=25-Hydroxycholesterol.svg |ImageClass = skin-invert-image |ImageSize= |IUPACName=Cholest-5-ene-3β,25-diol |SystematicName=(1''R'',3a''S'',3b''S'',7''S'',9a''R'',9b''S'',11a''R'')-1-[(2''R'')-6-Hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-2,3,3a,3b,4,6,7,8,9,9a,9b,10,11,11a-tetradecahydro-1''H''-cyclopenta[''a'']phenanthren-7-ol |OtherNames= |Section1={{Chembox Identifiers | CASNo=2140-46-7 | PubChem=65094 | ChEBI=42977 | ChemSpiderID=58604 | EC_number=635-752-4 | KEGG=C15519 | UNII=767JTD2N31 | DrugBank=04705 | InChI=1S/C27H46O2/c1-18(7-6-14-25(2,3)29)22-10-11-23-21-9-8-19-17-20(28)12-15-26(19,4)24(21)13-16-27(22,23)5/h8,18,20-24,28-29H,6-7,9-17H2,1-5H3/t18-,20+,21+,22-,23+,24+,26+,27-/m1/s1 | InChIKey=INBGSXNNRGWLJU-ZHHJOTBYSA-N | SMILES=CC(CCCC(C)(C)O)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C }} |Section2={{Chembox Properties | Formula=C<sub>27</sub>H<sub>46</sub>O<sub>2</sub> | MolarMass=402.7 | Appearance= | Density= | MeltingPt= | BoilingPt= | Solubility= }} |Section3={{Chembox Hazards | MainHazards= | FlashPt= | Autoignition= }} }}'''25-Hydroxycholesterol''' is a derivative of cholesterol, which plays a role in various biological processes in humans and other species. It is involved in cholesterol metabolism, antiviral process, inflammatory and immune response, and survival signaling pathway. 25-hydroxycholesterol is biosynthesized from cholesterol by adding a hydroxyl group at the position 25-carbon of a steroid nucleus. This reaction is catalyzed by cholesterol 25-hydroxylase, a family of enzymes that use oxygen and a di-iron cofactor to catalyze hydroxylation reaction.<ref name="pmid37781400">{{cite journal |vauthors=Zhang J, Zhu Y, Wang X, Wang J |title=25-hydroxycholesterol: an integrator of antiviral ability and signaling |journal=Front Immunol |volume=14 |issue= |article-number=1268104 |date=2023 |pmid=37781400 |pmc=10533924 |doi=10.3389/fimmu.2023.1268104 |url= |doi-access=free }}</ref><ref name="pmid33274010">{{cite journal |vauthors=Cao Q, Liu Z, Xiong Y, Zhong Z, Ye Q |title=Multiple Roles of 25-Hydroxycholesterol in Lipid Metabolism, Antivirus Process, Inflammatory Response, and Cell Survival |journal=Oxid Med Cell Longev |volume=2020 |issue= |article-number=8893305 |date=2020 |pmid=33274010 |pmc=7695496 |doi=10.1155/2020/8893305 |url= |doi-access=free }}</ref>
The CYP3A4 enzyme, a member of the cytochrome P450 family, can catalyze the oxidation of 25-hydroxycholesterol to 7α,25-dihydroxycholesterol, whereas 25-hydroxycholesterol can inhibit CYP4F2 mRNA expression, so that members of the cytochrome P450 family are also involved in the metabolism of 25-hydroxycholesterol besides cholesterol 25-hydroxylase.<ref name="pmid17142457">{{cite journal |vauthors=Hsu MH, Savas U, Griffin KJ, Johnson EF |title=Regulation of human cytochrome P450 4F2 expression by sterol regulatory element-binding protein and lovastatin |journal=J Biol Chem |volume=282 |issue=8 |pages=5225–36 |date=February 2007 |pmid=17142457 |doi=10.1074/jbc.M608176200 |url= |doi-access=free }}</ref>
25-hydroxycholesterol has been found in various organisms such as mice, rats, rabbits, and cows. {{As of|2023|post=,}} its presence in other species has not been extensively studied.<ref name="pmid33274010"/><ref name="pmid37781400"/>
== See also == * {{Annotated link|desc_first_letter_case=lower|cholesterol}}; * {{Annotated link|desc_first_letter_case=lower|cholesterol 25-hydroxylase}}; * {{Annotated link|desc_first_letter_case=lower|27-hydroxycholesterol}}.
== References ==
{{reflist}} ==Further reading== * {{cite journal |last1=Zu |first1=Shulong |last2=Deng |first2=Yong-Qiang |last3=Zhou |first3=Chao |last4=Li |first4=Jie |last5=Li |first5=Lili |last6=Chen |first6=Qi |last7=Li |first7=Xiao-Feng |last8=Zhao |first8=Hui |last9=Gold |first9=Sarah |last10=He |first10=Jun |last11=Li |first11=Xiang |last12=Zhang |first12=Changqing |last13=Yang |first13=Heng |last14=Cheng |first14=Genhong |last15=Qin |first15=Cheng-Feng |title=25-Hydroxycholesterol is a potent SARS-CoV-2 inhibitor |journal=Cell Research |date=November 2020 |volume=30 |issue=11 |pages=1043–1045 |doi=10.1038/s41422-020-00398-1 |pmid=32811977 |pmc=7431750 |s2cid=221146053 |language=en |issn=1748-7838}} {{DEFAULTSORT:Hydroxycholesterol, 25}}
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Category:Cholestanes Category:Sterols Category:Metabolic intermediates