7α-Hydroxycholesterol - Misplaced Pages

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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--2,3,3a,3b,4,6,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopentaphenanthrene-4,7-diol
Identifiers
CAS Number	566-26-7
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:17500
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/s1Key: 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/s1Key: OYXZMSRRJOYLLO-RVOWOUOIBF
SMILES CC(C)CCC(C)1CC21(CC32(C=C43(CC(C4)O)C)O)C O4C/C3=C/(O)1(CC2(1CC2(C)CCCC(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 , 100 kPa). Y verify (what is ?) Infobox references

Chemical compound

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.

References

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.

to HMG-CoA	Acetyl-CoA Acetoacetyl-CoA HMB HMB-CoA HMG-CoA
Ketone bodies	Acetone Acetoacetic acid β-Hydroxybutyric acid
to DMAPP	Mevalonic acid Phosphomevalonic acid 5-Diphosphomevalonic acid Isopentenyl pyrophosphate Dimethylallyl pyrophosphate
Geranyl-	Geranyl pyrophosphate Geranylgeranyl pyrophosphate
Carotenoid	Prephytoene diphosphate Phytoene

Nonhuman

To Sitosterol	Cycloartenol Cycloeucalenol Obtusifoliol 4α-methylfecosterol Isofucosterol 24-Methylenelophenol Sitosterol More Phytosterols see here instead.
To Ergocalciferol	Fecosterol Episterol Ergostatrienol Ergostatetraenol Ergosterol Ergocalciferol

Others

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