Compound

4-hydroxy-17beta-estradiol

A 4-hydroxy steroid that consists of 17β-estradiol having an additional hydroxy group at position 4.

Definition from ChEBI (CHEBI:62845), read 2026-09-23. CC BY 4.0.

CHEBI:62845ChEBI

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Structure

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A generated conformer of 4-hydroxy-17beta-estradiol — one low-energy arrangement PubChem computed, not a measured structure. Hydrogens are not drawn; the formula counts them.

Class: Organic compound
Formula: C18H24O3
Mass: 288.387 g/mol
Charge: 0
InChIKey: QOZFCKXEVSGWGS-ZHIYBZGJSA-N
SMILES: [H][C@@]12CCc3c(ccc(O)c3O)[C@@]1([H])CC[C@]1(C)[C@@H](O)CC[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

4-hydroxy-17beta-estradiol has the functional parent 17beta-estradiolCompoundChEBI CHEBI:62845Inferred only

Statements

21 statements

21 statements · 2 reference databases · Subject: 4-hydroxy-17beta-estradiol · Sources: Human-GEM, Rhea

Order

17beta-estradiol is converted to 4-hydroxy-17beta-estradiolCompoundHuman-GEM MAR02047Inferred only
17beta-estradiol is converted to 4-hydroxy-17beta-estradiolCompoundHuman-GEM MAR02046Inferred only
4-hydroxy-17beta-estradiol is converted to 17beta-estradiol 4-O-(beta-D-glucuronate)CompoundRhea RHEA:53040Inferred only
4-hydroxy-17beta-estradiol is converted to 4-hydroxy-17beta-estradiol 3-O-(beta-D-glucuronate)CompoundRhea RHEA:53036Inferred only
4-hydroxy-17beta-estradiol is converted to 4-methoxy-17beta-estradiolCompoundRhea RHEA:53096Inferred only
4-hydroxy-17beta-estradiol is metabolised by COMTProteinHuman-GEM MAR02048Inferred only
4-hydroxy-17beta-estradiol is metabolised by COMTProteinRhea RHEA:53096Inferred only
4-hydroxy-17beta-estradiol is metabolised by UGT1A8ProteinRhea RHEA:53040Inferred only
4-hydroxy-17beta-estradiol is metabolised by UGT1A8ProteinRhea RHEA:53036Inferred only
4-hydroxy-17beta-estradiol is metabolised by UGT1A9ProteinRhea RHEA:53040Inferred only
4-hydroxy-17beta-estradiol is metabolised by UGT2B7ProteinRhea RHEA:53040Inferred only
4-hydroxy-17beta-estradiol is a substrate of EPXProteinHuman-GEM MAR02088Inferred only

Show the remaining 9

4-hydroxy-17beta-estradiol is a substrate of EPXProteinHuman-GEM MAR02089Inferred only
4-hydroxy-17beta-estradiol is a substrate of LPOProteinHuman-GEM MAR02089Inferred only
4-hydroxy-17beta-estradiol is a substrate of LPOProteinHuman-GEM MAR02088Inferred only
4-hydroxy-17beta-estradiol is a substrate of LRTOMTProteinHuman-GEM MAR02048Inferred only
4-hydroxy-17beta-estradiol is a substrate of MPOProteinHuman-GEM MAR02088Inferred only
4-hydroxy-17beta-estradiol is a substrate of MPOProteinHuman-GEM MAR02089Inferred only
4-hydroxy-17beta-estradiol is a substrate of PRDX6ProteinHuman-GEM MAR02089Inferred only
4-hydroxy-17beta-estradiol is a substrate of PRDX6ProteinHuman-GEM MAR02088Inferred only
4-hydroxy-17beta-estradiol is a substrate of TPOProteinHuman-GEM MAR02088Inferred only

Reactions

13 reactions

17beta-estradiol+proton+NADPH(4-)+dioxygen4-hydroxy-17beta-estradiol+water+NADP(3-)
Catalysed by CYP3A4
Reaction pageLeft to rightBalancedEC 1.14.14.55cytosol
Human-GEM MAR02046CC BY 4.0Reference data
17beta-estradiol+proton+NADPH(4-)+dioxygen4-hydroxy-17beta-estradiol+water+NADP(3-)
Catalysed by CYP3A4
Reaction pageLeft to rightBalancedEC 1.14.14.55endoplasmic reticulum
Human-GEM MAR02047CC BY 4.0Reference data
4-hydroxy-17beta-estradiol+S-adenosyl-L-methionineMAM01011c+proton+CHEBI:16680
Catalysed by COMT or LRTOMT
Reaction pageReversibleBalancedEC 2.1.1.6cytosol
Human-GEM MAR02048CC BY 4.0Reference data
4-hydroxy-17beta-estradiol4-hydroxy-17beta-estradiol
Reaction pageReversibleBalancedcytosol, lysosome
Human-GEM MAR02087CC BY 4.0Reference data
MAM00413c+2water4-hydroxy-17beta-estradiol+hydrogen peroxide
Catalysed by MPO or TPO or PRDX6 or EPX or LPO
Reaction pageReversibleBalancedEC 1.11.1.7, 1.11.1.8, 1.11.2.2cytosol
Human-GEM MAR02088CC BY 4.0Reference data
MAM00413l+2water4-hydroxy-17beta-estradiol+hydrogen peroxide
Catalysed by MPO or PRDX6 or EPX or LPO
Reaction pageReversibleBalancedEC 1.11.1.7, 1.11.1.8, 1.11.2.2lysosome
Human-GEM MAR02089CC BY 4.0Reference data
4-hydroxy-17beta-estradiol4-hydroxy-17beta-estradiol
Reaction pageReversibleBalancedcytosol, extracellular space
Human-GEM MAR08905CC BY 4.0Reference data
4-hydroxy-17beta-estradiol4-hydroxy-17beta-estradiol
Reaction pageReversibleBalancedcytosol, endoplasmic reticulum
Human-GEM MAR08906CC BY 4.0Reference data
4-hydroxy-17beta-estradiol
Reaction pageReversibleBalance undeterminableextracellular space
Human-GEM MAR09355CC BY 4.0Reference data
17beta-estradiol+reduced [NADPH--hemoprotein reductase]+dioxygen4-hydroxy-17beta-estradiol+oxidized [NADPH--hemoprotein reductase]+water+hydron
Catalysed by CYP1A1 or CYP1A2 or CYP3A4 or CYP3A5 or CYP1B1
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:47280CC BY 4.0Reference data
4-hydroxy-17beta-estradiol+UDP-alpha-D-glucuronate4-hydroxy-17beta-estradiol 3-O-(beta-D-glucuronate)+UDP+hydron
Catalysed by UGT1A8
Reaction pageLeft to rightBalanced
Rhea RHEA:53036CC BY 4.0Reference data
4-hydroxy-17beta-estradiol+UDP-alpha-D-glucuronate17beta-estradiol 4-O-(beta-D-glucuronate)+UDP+hydron
Catalysed by UGT1A9 or UGT2B7 or UGT1A8
Reaction pageLeft to rightBalanced
Rhea RHEA:53040CC BY 4.0Reference data

Show the remaining 1

Other names

10 names

Resolves to: 4-hydroxy-17beta-estradiol

Also called: 3,4,17beta-estriol3,4,17beta-trihydroxy-1,3,5[10]-estratriene4-hydroxyestradiol4-Hydroxyestradiol-17beta4-OH-Estradiol4OHE2estra-1,3,5(10)-triene-2,4,17beta-triolST 18:3;O3
Systematic name: estra-1,3,5(10)-triene-3,14,17beta-triolestra-1,3,5(10)-triene-3,14,17β-triol