Structure Database (LMSD)
Common Name
16alpha-hydroxyestrone
Systematic Name
3,16α-dihydroxy-1,3,5(10)-estratrien-17-one
Synonyms
- 1.16a-Hydroxyestrone
LM ID
LMST02010041
Formula
Exact Mass
Calculate m/z
286.156895
Sum Composition
Status
Curated
3D model of 16alpha-hydroxyestrone
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Biological Context
16α-hydroxy Estrone (16α-OHE1) is a hydroxylated metabolite of E1 as well as an interconversion product with E2.1,2 E1 is 16α-hydroxylated by cytochrome P450 (CYP) isoforms, including CYP1A1, CYP3A5, CYP3A4, and CYP3A7, with CYP3A5 being breast-specific.3 16α-OHE1 is sulphatized or glucuronidated before excretion.3 It is increased in rheumatoid arthritis and decreased by physical activity.1,2 Unlike the parent estrogens and other hydroxylated metabolites of E1, 16α-OHE1 binds covalently and persistently activates estrogen receptors.4 In addition, this metabolite increases cell proliferation and does not suppress TNF-α secretion, whereas other estrogen metabolites are not pro-proliferative and have marked effects on TNF-α secretion.1,3 The levels of 16α-OHE1 are increased in some forms of hormone therapy.5 Because hormone therapy increases breast cancer risk, 16α-OHE1 has been implicated as a risk factor for breast cancer, although supportive data remains elusive.6,3,5
This information has been provided by Cayman Chemical
References
Reactions
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String Representations
InChiKey (Click to copy)
WPOCIZJTELRQMF-QFXBJFAPSA-N
InChi (Click to copy)
InChI=1S/C18H22O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-16,19-20H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,18+/m1/s1
SMILES (Click to copy)
C1(=CC2=C(C=C1)[C@]1([H])[C@]([H])([C@@]3([H])[C@@](CC1)(C)C(=O)[C@H](O)C3)CC2)O
Other Databases
KEGG ID
HMDB ID
CHEBI ID
PubChem CID
SwissLipids ID
Cayman ID
PDB ID
GuidePharm ID
Calculated Physicochemical Properties
Heavy Atoms
21
Rings
4
Aromatic Rings
1
Rotatable Bonds
0
Van der Waals Molecular Volume
275.43
Topological Polar Surface Area
57.53
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
3
logP
3.07
Molar Refractivity
79.63
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Created at
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Updated at
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