Compound
4beta-hydroxycholesterol
A oxysterol that is cholesterol in which the hydrogen at the 4β position has been replaced by a hydroxy group. A metabolite of cholesterol formed by the drug-metabolizing enzyme cytochrome P450 3A4, it is one of the major oxysterols in the human circulation.
Definition from ChEBI (CHEBI:85778), read 2026-09-23. CC BY 4.0.
Structure
- Class
- Organic compound
- Formula
- C27H46O2
- Mass
- 402.663 g/mol
- Charge
- 0
- InChIKey
- CZDKQKOAHAICSF-JSAMMMMSSA-N
- SMILES
- [H][C@@]12CC=C3[C@@H](O)[C@@H](O)CC[C@]3(C)[C@@]1([H])CC[C@@]1(C)[C@@]2([H])CC[C@]1([H])[C@H](C)CCCC(C)C
- Look it up
- ChEBIBy InChIKey
Identity from ChEBI. Not evidence.
What it touches on the way
Mechanistic reach
1 entity
1 entities reached.
0 reported hops1 assembled from the scaffold
What the reference databases state
Chemical structure
- 4beta-hydroxycholesterol has the functional parent cholesterolCompoundChEBI CHEBI:85778Inferred only
Statements
1 statement
1 statement · 1 reference database · Subject: 4beta-hydroxycholesterol · Sources: Rhea
- 4beta-hydroxycholesterol is metabolised by CYP3A4ProteinRhea RHEA:46128Inferred only
Reactions
4 reactions
4beta-hydroxycholesterol+reduced [NADPH--hemoprotein reductase]+dioxygenCHEBI:85779+oxidized [NADPH--hemoprotein reductase]+water+hydron
Catalysed by CYP7A1
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:46120CC BY 4.0Reference data
cholesterol+reduced [NADPH--hemoprotein reductase]+dioxygen4beta-hydroxycholesterol+oxidized [NADPH--hemoprotein reductase]+water+hydron
Catalysed by CYP3A4
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:46128CC BY 4.0Reference data
4beta-hydroxycholesterol+reduced [NADPH--hemoprotein reductase]+dioxygenCHEBI:86087+oxidized [NADPH--hemoprotein reductase]+water+hydron
Catalysed by CYP46A1
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:46392CC BY 4.0Reference data
4beta-hydroxycholesterol+2reduced [adrenodoxin]+dioxygen+2hydronCHEBI:86113+2oxidized [adrenodoxin]+water
Catalysed by CYP27A1
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:46428CC BY 4.0Reference data
Other names
8 names
Resolves to: 4beta-hydroxycholesterol
- Also called
- (3beta,4beta)-cholest-5-ene-3,4-diol(3β,4β)-cholest-5-ene-3,4-diol4beta-hydroxy-cholesterolcholest-5-en-3beta,4beta-diolcholest-5-en-3β,4β-diolST 27:1;O2
- Systematic name
- cholest-5-ene-3beta,4beta-diolcholest-5-ene-3β,4β-diol