25-Hydroxycholesterol

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, antivirus 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.^[1][2]

25-Hydroxycholesterol

Identifiers
CAS Number	2140-46-7
3D model (JSmol)	Interactive image
ChEBI	CHEBI:42977
ChemSpider	58604
DrugBank	04705
ECHA InfoCard	100.163.612
EC Number	635-752-4
KEGG	C15519
PubChem CID	65094
UNII	767JTD2N31
CompTox Dashboard (EPA)	DTXSID5044023
InChI 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 Key: INBGSXNNRGWLJU-ZHHJOTBYSA-N
SMILES CC(CCCC(C)(C)O)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C
Properties
Chemical formula	C27H46O2
Molar mass	402.7
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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.^[3]

25-hydroxycholesterol has been found in various organisms such as mice, rats, rabbits, and cows. As of 2023,^[update] its presence in other species has not been extensively studied.^[2][1]

See also

• cholesterol – sterol biosynthesized by all animal cells;
• cholesterol 25-hydroxylase – class of enzymes;
• 27-hydroxycholesterol – chemical compoundPages displaying wikidata descriptions as a fallback.

References

1. Zhang J, Zhu Y, Wang X, Wang J (2023). "25-hydroxycholesterol: an integrator of antiviral ability and signaling". Front Immunol. 14: 1268104. doi:10.3389/fimmu.2023.1268104. PMC 10533924. PMID 37781400.
2. Cao Q, Liu Z, Xiong Y, Zhong Z, Ye Q (2020). "Multiple Roles of 25-Hydroxycholesterol in Lipid Metabolism, Antivirus Process, Inflammatory Response, and Cell Survival". Oxid Med Cell Longev. 2020: 8893305. doi:10.1155/2020/8893305. PMC 7695496. PMID 33274010.
3. Hsu MH, Savas U, Griffin KJ, Johnson EF (February 2007). "Regulation of human cytochrome P450 4F2 expression by sterol regulatory element-binding protein and lovastatin". J Biol Chem. 282 (8): 5225–36. doi:10.1074/jbc.M608176200. PMID 17142457.

Further reading

• Zu S, Deng YQ, Zhou C, Li J, Li L, Chen Q, Li XF, Zhao H, Gold S, He J, Li X, Zhang C, Yang H, Cheng G, Qin CF (November 2020). "25-Hydroxycholesterol is a potent SARS-CoV-2 inhibitor". Cell Research. 30 (11): 1043–1045. doi:10.1038/s41422-020-00398-1. ISSN 1748-7838. PMC 7431750. PMID 32811977. S2CID 221146053.