Compound

2-hydroxyestrone

A 2-hydroxy steroid that is estrone substituted by a hydroxy group at position 2.

Definition from ChEBI (CHEBI:1156), read 2026-09-23. CC BY 4.0.

CHEBI:1156ChEBI

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Structure

2D depiction · 3D model shown

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A generated conformer of 2-hydroxyestrone — one low-energy arrangement PubChem computed, not a measured structure. Hydrogens are not drawn; the formula counts them.

Class: Organic compound
Formula: C18H22O3
Mass: 286.371 g/mol
Charge: 0
InChIKey: SWINWPBPEKHUOD-JPVZDGGYSA-N
SMILES: [H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])c3cc(O)c(O)cc3CC[C@@]21[H]
Look it up: ChEBI PubChem By InChIKey

Identity from ChEBI, geometry from PubChem. Not evidence.

What it touches on the way

Mechanistic reach

9 entities

9 entities reached.

0 reported hops9 assembled from the scaffold

What the reference databases state

Chemical structure

2-hydroxy-3-methoxy-estrone has the functional parent 2-hydroxyestroneCompoundChEBI CHEBI:136980Inferred only
2-hydroxyestrone has the functional parent estroneCompoundChEBI CHEBI:1156Inferred only

Statements

36 statements

36 statements · 2 reference databases · Subject: 2-hydroxyestrone · Sources: Human-GEM, Rhea

Order

2-hydroxyestrone is converted to 2-hydroxy-3-methoxy-estroneCompoundRhea RHEA:53108Inferred only
2-hydroxyestrone is converted to 2-hydroxyestrone 3-O-(beta-D-glucuronate)CompoundRhea RHEA:53048Inferred only
2-methoxyestrone is converted to 2-hydroxyestroneCompoundHuman-GEM MAR02059Inferred only
2-hydroxyestrone is converted to 2-methoxyestroneCompoundHuman-GEM MAR02058Inferred only
2-hydroxyestrone is converted to 2-methoxyestroneCompoundHuman-GEM MAR02059Inferred only
2-hydroxyestrone is converted to 2-methoxyestroneCompoundRhea RHEA:53100Inferred only
2-methoxyestrone is converted to 2-hydroxyestroneCompoundHuman-GEM MAR02058Inferred only
estrone is converted to 2-hydroxyestroneCompoundHuman-GEM MAR02055Inferred only
estrone is converted to 2-hydroxyestroneCompoundHuman-GEM MAR02056Inferred only
estrone is converted to 2-hydroxyestroneCompoundHuman-GEM MAR02057Inferred only
2-hydroxyestrone is metabolised by COMTProteinRhea RHEA:53100Inferred only
2-hydroxyestrone is metabolised by COMTProteinHuman-GEM MAR02058Inferred only

Show the remaining 24

2-hydroxyestrone is metabolised by COMTProteinRhea RHEA:53108Inferred only
2-hydroxyestrone is metabolised by COMTProteinHuman-GEM MAR02059Inferred only
2-hydroxyestrone is metabolised by COMTProteinHuman-GEM MAR02060Inferred only
2-hydroxyestrone is metabolised by UGT1A1ProteinRhea RHEA:53048Inferred only
2-hydroxyestrone is metabolised by UGT1A8ProteinRhea RHEA:53048Inferred only
2-hydroxyestrone is metabolised by UGT1A9ProteinRhea RHEA:53048Inferred only
2-hydroxyestrone is a substrate of EPXProteinHuman-GEM MAR02063Inferred only
2-hydroxyestrone is a substrate of EPXProteinHuman-GEM MAR02062Inferred only
2-hydroxyestrone is a substrate of EPXProteinHuman-GEM MAR02061Inferred only
2-hydroxyestrone is a substrate of LPOProteinHuman-GEM MAR02062Inferred only
2-hydroxyestrone is a substrate of LPOProteinHuman-GEM MAR02063Inferred only
2-hydroxyestrone is a substrate of LPOProteinHuman-GEM MAR02061Inferred only
2-hydroxyestrone is a substrate of LRTOMTProteinHuman-GEM MAR02058Inferred only
2-hydroxyestrone is a substrate of LRTOMTProteinHuman-GEM MAR02060Inferred only
2-hydroxyestrone is a substrate of LRTOMTProteinHuman-GEM MAR02059Inferred only
2-hydroxyestrone is a substrate of MPOProteinHuman-GEM MAR02061Inferred only
2-hydroxyestrone is a substrate of MPOProteinHuman-GEM MAR02063Inferred only
2-hydroxyestrone is a substrate of MPOProteinHuman-GEM MAR02062Inferred only
2-hydroxyestrone is a substrate of PRDX6ProteinHuman-GEM MAR02062Inferred only
2-hydroxyestrone is a substrate of PRDX6ProteinHuman-GEM MAR02063Inferred only
2-hydroxyestrone is a substrate of PRDX6ProteinHuman-GEM MAR02061Inferred only
2-hydroxyestrone is a substrate of TPOProteinHuman-GEM MAR02063Inferred only
2-hydroxyestrone is a substrate of TPOProteinHuman-GEM MAR02062Inferred only
2-hydroxyestrone is a substrate of TPOProteinHuman-GEM MAR02061Inferred only

Reactions

15 reactions

estrone+proton+NADPH(4-)+dioxygen2-hydroxyestrone+water+NADP(3-)
Catalysed by CYP3A4
Reaction pageLeft to rightBalancedEC 1.14.14.55cytosol
Human-GEM MAR02055CC BY 4.0Reference data
estrone+proton+NADPH(4-)+dioxygen2-hydroxyestrone+water+NADP(3-)
Catalysed by CYP3A4
Reaction pageLeft to rightBalancedEC 1.14.14.55lysosome
Human-GEM MAR02056CC BY 4.0Reference data
estrone+proton+NADPH(4-)+dioxygen2-hydroxyestrone+water+NADP(3-)
Catalysed by CYP3A4
Reaction pageLeft to rightBalancedEC 1.14.14.55endoplasmic reticulum
Human-GEM MAR02057CC BY 4.0Reference data
2-hydroxyestrone+S-adenosyl-L-methionine2-methoxyestrone+proton+CHEBI:16680
Catalysed by COMT or LRTOMT
Reaction pageReversibleBalancedEC 2.1.1.6cytosol
Human-GEM MAR02058CC BY 4.0Reference data
2-hydroxyestrone+S-adenosyl-L-methionine2-methoxyestrone+proton+CHEBI:16680
Catalysed by COMT or LRTOMT
Reaction pageReversibleBalancedEC 2.1.1.6endoplasmic reticulum
Human-GEM MAR02059CC BY 4.0Reference data
MAM00645c+proton+CHEBI:166802-hydroxyestrone+S-adenosyl-L-methionine
Catalysed by COMT or LRTOMT
Reaction pageReversibleBalancedEC 2.1.1.6cytosol
Human-GEM MAR02060CC BY 4.0Reference data
2-hydroxyestrone+proton+hydrogen peroxideMAM01792c+2water
Catalysed by MPO or TPO or PRDX6 or EPX or LPO
Reaction pageReversibleUnbalancedEC 1.11.1.7, 1.11.1.8, 1.11.2.2cytosol
Human-GEM MAR02061CC BY 4.0Reference data
2-hydroxyestrone+proton+hydrogen peroxideMAM01792l+2water
Catalysed by MPO or TPO or PRDX6 or EPX or LPO
Reaction pageReversibleUnbalancedEC 1.11.1.7, 1.11.1.8, 1.11.2.2lysosome
Human-GEM MAR02062CC BY 4.0Reference data
2-hydroxyestrone+proton+hydrogen peroxideMAM01792r+2water
Catalysed by MPO or TPO or PRDX6 or EPX or LPO
Reaction pageReversibleUnbalancedEC 1.11.1.7, 1.11.1.8, 1.11.2.2endoplasmic reticulum
Human-GEM MAR02063CC BY 4.0Reference data
2-hydroxyestrone+ATP+water2-hydroxyestrone+ADP+proton+phosphate(3-)
Reaction pageLeft to rightBalancedcytosol, extracellular space
Human-GEM MAR11859CC BY 4.0Reference data
2-hydroxyestrone
Reaction pageReversibleBalance undeterminableextracellular space
Human-GEM MAR11860CC BY 4.0Reference data
estrone+reduced [NADPH--hemoprotein reductase]+dioxygen2-hydroxyestrone+oxidized [NADPH--hemoprotein reductase]+water+hydron
Catalysed by CYP1A1 or CYP1A2 or CYP3A4 or CYP19A1 or CYP2C9 or CYP2B6 or CYP3A5 or CYP3A7 or CYP1B1
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:47208CC BY 4.0Reference data

Show the remaining 3

Other names

3 names

Resolves to: 2-hydroxyestrone

Also called: 2,3-dihydroxy-estra-1,3,5(10)-trien-17-oneST 18:4;O3
Systematic name: 2,3-dihydroxyestra-1,3,5(10)-trien-17-one