7α-Hydroxycholesterol

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

7α-Hydroxycholesterol

Names
IUPAC name (3S,7S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol
Identifiers
CAS Number	566-26-7
3D model (JSmol)	Interactive image Interactive image
ChemSpider	96891
IUPHAR/BPS	4351
MeSH	7+alpha-hydroxycholesterol
PubChem CID	107722
UNII	95D0I22I0V
CompTox Dashboard (EPA)	DTXSID40903965
InChI 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 Key: OYXZMSRRJOYLLO-RVOWOUOISA-N 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
SMILES 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
Chemical formula	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. Miao J (2008). Regulation of Bile Acid Biosynthesis by Orphan Nuclear Receptor Small Heterodimer Partner (Ph.D.). University of Illinois at Urbana-Champaign.