22R-Hydroxycholesterol, or (3β)-cholest-5-ene-3,22-diol is an endogenous, metabolic intermediate in the biosynthesis of the steroid hormones from cholesterol.[1][2] Cholesterol ((3β)-cholest-5-en-3-ol) is hydroxylated by cholesterol side-chain cleavage enzyme (P450scc) to form 22R-hydroxycholesterol, which is subsequently hydroxylated again by P450scc to form 20α,22R-dihydroxycholesterol, and finally the bond between carbons 20 and 22 is cleaved by P450scc to form pregnenolone ((3β)-3-hydroxypregn-5-en-20-one),[1][2] the precursor to the steroid hormones.
Names | |
---|---|
IUPAC name
(22R)-Cholest-5-ene-3β,22-diol
| |
Systematic IUPAC name
(1R,3aS,3bS,7S,9aR,9bS,11aS)-1-[(2S,3R)-3-Hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-2,3,3a,3b,4,6,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-7-ol | |
Identifiers | |
| |
3D model (JSmol)
|
|
ChEBI |
|
ChEMBL |
|
ChemSpider |
|
PubChem CID
|
|
UNII |
|
CompTox Dashboard (EPA)
|
|
| |
| |
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).
Infobox references
|
It is an agonist of the liver X receptor.