Compound
16alpha-hydroxyestrone
The 16α-hydroxy derivative of estrone; a minor estrogen metabolite.
Definition from ChEBI (CHEBI:776), read 2026-09-23. CC BY 4.0.
Structure
- Class
- Organic compound
- Formula
- C18H22O3
- Mass
- 286.371 g/mol
- Charge
- 0
- InChIKey
- WPOCIZJTELRQMF-QFXBJFAPSA-N
- SMILES
- [H][C@@]12C[C@@H](O)C(=O)[C@@]1(C)CC[C@]1([H])c3ccc(O)cc3CC[C@@]21[H]
- Look it up
- ChEBIBy InChIKey
Identity from ChEBI. Not evidence.
What it touches on the way
Mechanistic reach
2 entities
2 entities reached.
0 reported hops2 assembled from the scaffold
What the reference databases state
Chemical structure
- 16alpha-hydroxyestrone 16-O-(beta-D-glucuronate) has the functional parent 16alpha-hydroxyestroneCompoundChEBI CHEBI:136636Inferred only
- 16alpha-hydroxyestrone 3-O-(beta-D-glucuronate) has the functional parent 16alpha-hydroxyestroneCompoundChEBI CHEBI:136635Inferred only
- 16alpha-hydroxyestrone has the functional parent estroneCompoundChEBI CHEBI:776Inferred only
Statements
7 statements
7 statements · 2 reference databases · Subject: 16alpha-hydroxyestrone · Sources: Human-GEM, Rhea
- 16alpha-hydroxyestrone is converted to 16alpha-hydroxyestrone 16-O-(beta-D-glucuronate)CompoundRhea RHEA:52452Inferred only
- 16alpha-hydroxyestrone is converted to 16alpha-hydroxyestrone 3-O-(beta-D-glucuronate)CompoundRhea RHEA:52448Inferred only
- 16alpha-hydroxyestrone is converted to 16alpha,17beta-estriolCompoundHuman-GEM MAR11369Inferred only
- estrone is converted to 16alpha-hydroxyestroneCompoundHuman-GEM MAR02054Inferred only
- estrone is converted to 16alpha-hydroxyestroneCompoundHuman-GEM MAR02053Inferred only
- 16alpha-hydroxyestrone is metabolised by UGT1A10ProteinRhea RHEA:52448Inferred only
- 16alpha-hydroxyestrone is metabolised by UGT2B7ProteinRhea RHEA:52452Inferred only
Reactions
9 reactions
16alpha-hydroxyestrone+16alpha-hydroxyestrone+MAM00432r+MAM00604c+MAM00624c+MAM00641c+MAM00641m+MAM00641r+MAM00641x+MAM00642c+MAM00642m+MAM00642r+MAM00642x+MAM00644c+MAM00645c+2-hydroxy-17beta-estradiol+2-hydroxy-17beta-estradiol+MAM00651c+MAM00651m+MAM00651r+MAM00651x+MAM00652c+MAM00652m+MAM00652r+MAM00652x+2-methoxy-17beta-estradiol+2-methoxyestrone+2-methoxyestrone+MAM00747r+MAM00828r+MAM00830c+MAM00925c+MAM00927c+MAM00945c+MAM00947c+MAM00949c+MAM00987c+MAM00987m+MAM00987r+MAM00987x+(E)-4-hydroxynon-2-enal+MAM01001c+MAM01001m+MAM01001r+MAM01001x+MAM01011c+4-methoxyestrone+3alpha-hydroxy-5alpha-pregnan-20-one+MAM01792r+MAM01794r+MAM02469cMAM10001e
Reaction pageLeft to rightBalance undeterminablecytosol, endoplasmic reticulum, mitochondrial matrix, peroxisome, lysosome, extracellular space
Human-GEM MAR00037CC BY 4.0Reference data
estrone+proton+NADPH(4-)+dioxygen16alpha-hydroxyestrone+water+NADP(3-)
Catalysed by CYP3A43 or CYP2D6 or CYP3A5 or CYP2E1 or CYP2J2 or CYP19A1 or CYP1B1 or CYP2C9 or CYP2C8 or CYP1A1 or CYP1A2 or CYP4B1 and 12 more alternatives
Reaction pageLeft to rightBalancedEC 1.14.14.1cytosol
Human-GEM MAR02053CC BY 4.0Reference data
estrone+proton+NADPH(4-)+dioxygen16alpha-hydroxyestrone+water+NADP(3-)
Catalysed by CYP3A43 or CYP2D6 or CYP3A5 or CYP2C18 or CYP2E1 or CYP2J2 or CYP19A1 or CYP1B1 or CYP2C9 or CYP2C8 or CYP1A1 or CYP1A2 and 12 more alternatives
Reaction pageLeft to rightBalancedEC 1.14.14.1endoplasmic reticulum
Human-GEM MAR02054CC BY 4.0Reference data
16alpha-hydroxyestrone16alpha-hydroxyestrone
Reaction pageReversibleBalancedcytosol, extracellular space
Human-GEM MAR10482CC BY 4.0Reference data
Reaction pageReversibleBalance undeterminableextracellular space
Human-GEM MAR10491CC BY 4.0Reference data
16alpha-hydroxyestrone+proton+NADH(2-)16alpha,17beta-estriol+NAD(+)
Reaction pageLeft to rightBalancedEC 6.2.1.2endoplasmic reticulum
Human-GEM MAR11369CC BY 4.0Reference data
estrone+reduced [NADPH--hemoprotein reductase]+dioxygen16alpha-hydroxyestrone+oxidized [NADPH--hemoprotein reductase]+water+hydron
Catalysed by CYP1A1 or CYP3A4 or CYP2C8 or CYP3A7
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:47204CC BY 4.0Reference data
16alpha-hydroxyestrone+UDP-alpha-D-glucuronate16alpha-hydroxyestrone 3-O-(beta-D-glucuronate)+UDP+hydron
Catalysed by UGT1A10
Reaction pageLeft to rightBalanced
Rhea RHEA:52448CC BY 4.0Reference data
16alpha-hydroxyestrone+UDP-alpha-D-glucuronate16alpha-hydroxyestrone 16-O-(beta-D-glucuronate)+UDP+hydron
Catalysed by UGT2B7
Reaction pageLeft to rightBalanced
Rhea RHEA:52452CC BY 4.0Reference data
Other names
11 names
Resolves to: 16alpha-hydroxyestrone
- Also called
- 1.16a-Hydroxyestrone16 alpha OHE16alpha-OHE16alpha-OHE13,16alpha-dihydroxy-1,3,5(10)-estratrien-17-one3,16alpha-Dihydroxyestra-1,3,5(10)-trien-17-one3,16α-dihydroxy-1,3,5(10)-estratrien-17-oneestra-1,3,5(10)-triene-3,16alpha-diol-17-oneestra-1,3,5(10)-triene-3,16α-diol-17-oneST 18:4;O3
- Systematic name
- 3,16α-dihydroxyestra-1,3,5(10)-trien-17-one