22-Hydroxycholesterol
Basic information
- CAS
17711-16-9- Standard SMILES
CC(C)CCC(O)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C- InChIKey
RZPAXNJLEKLXNO-UKNNTIGFSA-N- Molecular formula
- C27H46O2
- Average molar mass
- 402.7 g/mol
- Monoisotopic mass
- 402.34978071
Overview
22-Hydroxycholesterol is a cholanoid.
Names & identifiers
- Preferred name
- 22-Hydroxycholesterol
- IUPAC
- (3S,8S,9S,10R,13S,14S,17R)-17-[(2S)-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
- English name
- 22-hydroxycholesterol
- Molecular formula
- C27H46O2
- Molecular weight
- 402.65
Names & synonyms
22-Hydroxycholesterol17711-16-9Cholest-5-ene-3beta,22-diolcholest-5-en-3beta,22-diolTJ9HV8VPD2DTXSID3090434022(R)OH cholesterolRefChem:89715DTXCID401333496(3S,8S,9S,10R,13S,14S,17R)-17-[(2S)-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-olCholest-5-ene-3,22-diol, (3beta)-UNII-TJ9HV8VPD2
Show more names
Cholest-5-ene-3β,22-diol(3β)-Cholest-5-ene-3,22-diolCholest-5-ene-3,22-diol, (3β)-22-Hydroxy Cholesterol (Mixture of DiastereoMers)
SCHEMBL103514CHEMBL3218924CHEBI:166802LMST01010054(1R,3aS,3bS,7S,9aR,9bS,11aS)-1-[(2S)-3-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-olCHOLEST-5-ENE-3.BETA.,22-DIOLPD015597DB-220267
Database identifiers
- CAS
Properties
Computed structural properties
- XLogP
- 7
- Topological polar surface area
- 40.5 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 5
- Heavy atoms
- 29
- Formal charge
- 0
- Complexity
- 624
Experimental & physicochemical properties
LipidsLipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Cholesterol and derivatives [ST0101]
Physicochemical properties
- Melting point
- 168 · 168-175 °C
- Boiling point
- 513.1 · 513.1±23.0 °C(Predicted)
- Density
- 1.03 · 1.03±0.1 g/cm3(Predicted)
- pka
- 15.01 · 15.01±0.20(Predicted)
- FDA UNII
- 9 HV8VPD2 · TJ9HV8VPD2
Chemistry & industry
Applications
UsesA metabolite of Cholesterol (C432501). 22-Hydroxycholesterol inhibits chemokine receptor activity.
Upstream & downstream products
Upstream raw materials
Additional notes
DefinitionChEBI: 22-Hydroxycholesterol is a cholanoid.
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Compound notes
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