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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
  • 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
  • 65094
UNII
  • 767JTD2N31
  • DTXSID5044023
  • 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
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).

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, its presence in other species has not been extensively studied.[2][1]

See also edit

References edit

  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 edit

  • 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.

hydroxycholesterol, derivative, cholesterol, which, plays, role, various, biological, processes, humans, other, species, involved, cholesterol, metabolism, antivirus, process, inflammatory, immune, response, survival, signaling, pathway, hydroxycholesterol, bi. 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 IdentifiersCAS Number 2140 46 73D model JSmol Interactive imageChEBI CHEBI 42977ChemSpider 58604DrugBank 04705ECHA InfoCard 100 163 612EC Number 635 752 4KEGG C15519PubChem CID 65094UNII 767JTD2N31CompTox Dashboard EPA DTXSID5044023InChI 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 s1Key INBGSXNNRGWLJU ZHHJOTBYSA NSMILES CC CCCC C C O C1CCC2C1 CCC3C2CC C4C3 CCC C4 O C CPropertiesChemical formula C27H46O2Molar mass 402 7Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox referencesThe CYP3A4 enzyme a member of the cytochrome P450 family can catalyze the oxidation of 25 hydroxycholesterol to 7a 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 editcholesterol sterol biosynthesized by all animal cells cholesterol 25 hydroxylase class of enzymes 27 hydroxycholesterol chemical compoundPages displaying wikidata descriptions as a fallback References edit 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 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 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 editZu 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 Retrieved from https en wikipedia org w index php title 25 Hydroxycholesterol amp oldid 1217556570, wikipedia, wiki, book, books, library,

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