Structure via PubChem · Public domain (PubChem)
22R-Hydroxycholesterol
Sign in to save'22R-Hydroxycholesterol, or (3β)-cholest-5-ene-3,22-diol' is an endogenous, metabolic intermediate in the biosynthesis of the steroid hormones from cholesterol. 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), the precursor to the steroid hormones.
Chemical data
- Formula
- C27H46O2
- Molecular weight
- 402.7 g/mol
- IUPAC name
- (3S,8S,9S,10R,13S,14S,17R)-17-[(2S,3R)-3-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
- SMILES
- C[C@@H]([C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C)[C@@H](CCC(C)C)O
- InChIKey
- RZPAXNJLEKLXNO-GFKLAVDKSA-N
- XLogP
- 7
- Polar surface area
- 40.5 Ų
- H-bond donors
- 2
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- sterol
- Mass
- 402.349781
Show 4 more facts
- chemical formula
- C₂₇H₄₆O₂
- isomeric SMILES
- [H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)[C@H](O)CCC(C)C
- canonical SMILES
- CC(C)CCC(C(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C)O
- found in taxon
- Ruscus aculeatus
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- See also
- References
'22R-Hydroxycholesterol, or (3β)-cholest-5-ene-3,22-diol' is an endogenous, metabolic intermediate in the biosynthesis of the steroid hormones from cholesterol. 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), the precursor to the steroid hormones.
It is an agonist of the liver X receptor.
Excerpted from Wikipedia’s “22R-Hydroxycholesterol” article, available under the CC BY-SA 4.0 licence.