Compound
4-hydroxyestrone
A 4-hydroxy steroid that is estrone substituted by a hydroxy group at position 4.
Definition from ChEBI (CHEBI:87602), read 2026-09-23. CC BY 4.0.
Structure
- Class
- Organic compound
- Formula
- C18H22O3
- Mass
- 286.371 g/mol
- Charge
- 0
- InChIKey
- XQZVQQZZOVBNLU-QDTBLXIISA-N
- SMILES
- [H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])c3ccc(O)c(O)c3CC[C@@]21[H]
- Look it up
- ChEBIBy InChIKey
Identity from ChEBI. Not evidence.
What it touches on the way
Mechanistic reach
4 entities
4 entities reached.
0 reported hops4 assembled from the scaffold
What the reference databases state
Chemical structure
- 4-hydroxyestrone has the functional parent estroneCompoundChEBI CHEBI:87602Inferred only
Statements
8 statements
8 statements · 1 reference database · Subject: 4-hydroxyestrone · Sources: Rhea
- 4-hydroxyestrone is converted to 4-hydroxyestrone 3-O-(beta-D-glucuronate)CompoundRhea RHEA:53052Inferred only
- 4-hydroxyestrone is converted to 4-methoxyestroneCompoundRhea RHEA:53104Inferred only
- 4-hydroxyestrone is converted to estrone 4-O-(beta-D-glucuronate)CompoundRhea RHEA:53060Inferred only
- 4-hydroxyestrone is metabolised by COMTProteinRhea RHEA:53104Inferred only
- 4-hydroxyestrone is metabolised by UGT1A8ProteinRhea RHEA:53052Inferred only
- 4-hydroxyestrone is metabolised by UGT1A8ProteinRhea RHEA:53060Inferred only
- 4-hydroxyestrone is metabolised by UGT1A9ProteinRhea RHEA:53060Inferred only
- 4-hydroxyestrone is metabolised by UGT2B7ProteinRhea RHEA:53060Inferred only
Reactions
6 reactions
estrone+reduced [NADPH--hemoprotein reductase]+dioxygen4-hydroxyestrone+oxidized [NADPH--hemoprotein reductase]+water+hydron
Catalysed by CYP1A1 or CYP1A2 or CYP3A4 or CYP3A5 or CYP3A7 or CYP1B1
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:47292CC BY 4.0Reference data
4-hydroxyestrone+UDP-alpha-D-glucuronate4-hydroxyestrone 3-O-(beta-D-glucuronate)+UDP+hydron
Catalysed by UGT1A8
Reaction pageLeft to rightBalanced
Rhea RHEA:53052CC BY 4.0Reference data
4-hydroxyestrone+UDP-alpha-D-glucuronateestrone 4-O-(beta-D-glucuronate)+UDP+hydron
Catalysed by UGT1A9 or UGT2B7 or UGT1A8
Reaction pageLeft to rightBalanced
Rhea RHEA:53060CC BY 4.0Reference data
4-hydroxyestrone+S-adenosyl-L-methionine4-methoxyestrone+S-adenosyl-L-homocysteine+hydron
Catalysed by COMT
Reaction pageLeft to rightBalanced
Rhea RHEA:53104CC BY 4.0Reference data
4-hydroxyestrone+dioxygenCHEBI:137521+hydron
Reaction pageDirection not assertedBalanced
Rhea RHEA:53608CC BY 4.0Reference data
4-hydroxyestrone+ammonium+dioxygenCHEBI:137549+2water+2hydron
Reaction pageDirection not assertedBalanced
Rhea RHEA:57684CC BY 4.0Reference data
Other names
5 names
Resolves to: 4-hydroxyestrone
- Also called
- 3,4-dihydroxy-1,3,5(10)-estratrien-17-one3,4-dihydroxy-estra-1,3,5(10)-trien-17-oneestra-1,3,5(10)-triene-3,4-diol-17-oneST 18:4;O3
- Systematic name
- 3,4-dihydroxyestra-1,3,5(10)-trien-17-one