7α-Hydroxycholesterol

7α-Hydroxycholesterol

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
PubChem	107722
ChemSpider	96891^Y
MeSH	7+alpha-hydroxycholesterol
Jmol-3D images	Image 1 Image 2
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
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^Y Key: OYXZMSRRJOYLLO-RVOWOUOISA-N^Y 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
Properties
Molecular formula	C₂₇H₄₆O₂
Molar mass	402.653 g/mol
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

7α-Hydroxycholesterol is a precursor of bile acids, created by cholesterol 7 alpha-hydroxylase. It is the rate-determining step.

to HMG-CoA	Acetyl-CoA · Acetoacetyl-CoA · HMG-CoA

Ketone bodies	Acetone · Acetoacetic acid · beta-Hydroxybutyric acid

to DMAPP	Mevalonic acid · Phosphomevalonic acid · 5-Diphosphomevalonic acid · Isopentenyl pyrophosphate · Dimethylallyl pyrophosphate

Geranyl-	Geranyl pyrophosphate · Geranylgeranyl pyrophosphate

Carotenoid	Prephytoene diphosphate · Phytoene

Mineralocorticoids	Pregnenolone · Progesterone · Cortodoxone · Corticosterone · Aldosterone

Glucocorticoids	Pregnenolone · 17-Hydroxypregnenolone · 17-Hydroxyprogesterone · Cortisol Cortisol · Cortisone

Androgens (C19 androstane)	DHEA · Androstenedione/5-Androstenediol · Testosterone · Dihydrotestosterone DHEA sulfate · Epitestosterone

Estrogens (C18 estrane)	Estrone · Estradiol · Estriol

Nonhuman

Phytosterols	Stigmasterol · Brassicasterol

Ergosterols	Ergosterol · Ergocalciferol

mt, k, c/g/r/p/y/i, f/h/s/l/o/e, a/u, n, m

k, cgrp/y/i, f/h/s/l/o/e, au, n, m, epon

m(A16/C10),i(k, c/g/r/p/y/i, f/h/s/o/e, a/u, n, m)

anat/phys/devp/horm

noco(d)/cong/tumr, sysi/epon

proc, drug (A10/H1/H2/H3/H5)

biochemical families: prot · nucl · carb (glpr, alco, glys) · lipd (fata/i, phld, strd, gllp, eico) · amac/i · ncbs/i · ttpy/i