7α-Hydroxycholesterol

7α-Hydroxycholesterol is a precursor of bile acids, created by cholesterol 7α-hydroxylase (CYP7A1). Its formation is the rate-determining step in bile acid synthesis.[1]

7α-Hydroxycholesterol
Names
IUPAC name
Cholest-5-ene-3β,7α-diol
Systematic IUPAC name
(1R,3aS,3bS,4S,7S,9aR,9bS,11aR)-9a,11a-Dimethyl-1-[(2R)-6-methylheptan-2-yl]-2,3,3a,3b,4,6,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthrene-4,7-diol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
MeSH 7+alpha-hydroxycholesterol
UNII
  • InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h16-18,20-25,28-29H,6-15H2,1-5H3/t18-,20+,21-,22+,23+,24-,25+,26+,27-/m1/s1 checkY
    Key: OYXZMSRRJOYLLO-RVOWOUOISA-N checkY
  • InChI=1/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h16-18,20-25,28-29H,6-15H2,1-5H3/t18-,20+,21-,22+,23+,24-,25+,26+,27-/m1/s1
    Key: OYXZMSRRJOYLLO-RVOWOUOIBF
  • CC(C)CCC[C@@H](C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2[C@@H](C=C4[C@@]3(CC[C@@H](C4)O)C)O)C
  • O[C@@H]4C/C3=C/[C@@H](O)[C@@H]1[C@H](CC[C@]2([C@H]1CC[C@@H]2[C@H](C)CCCC(C)C)C)[C@@]3(C)CC4
Properties
C27H46O2
Molar mass 402.653 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

References
  1. Chiang JY, Ferrell JM (March 2020). "Bile acid receptors FXR and TGR5 signaling in fatty liver diseases and therapy". American Journal of Physiology. Gastrointestinal and Liver Physiology. 318 (3): G554–G573. doi:10.1152/ajpgi.00223.2019. PMC 7099488. PMID 31984784.



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