25-Hydroxycholesterol

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 Edit this at Wikidata
EC Number
  • 635-752-4
KEGG
  • C15519
PubChem CID
  • 65094
UNII
  • 767JTD2N31
CompTox Dashboard (EPA)
  • DTXSID5044023 Edit this at Wikidata
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
  • 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
Chemical compound

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]

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

References

  1. ^ a b 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. ^ a b 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.