16α-hydroxyestrone   Click here for help

GtoPdb Ligand ID: 12965

Synonyms: 16α-OHE1 | 16-hydroxyestrone | 16alpha-hydroxyestrone | 16alpha-OHE1
PDB Ligand
Compound class: Synthetic organic
Comment: 16α-hydroxyestrone is an estrogenic metabolite that is a 16-hydroxylation product generated during the catalytic breakdown of estrone by cytochrome P450 enzymes in the liver (principally CYP3A4 and 3A5).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 0
Topological polar surface area 57.53
Molecular weight 286.37
XLogP 2.53
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES C[C@@]12CC[C@@H]3C4=CC=C(C=C4CC[C@H]3[C@@H]2C[C@H](C1=O)O)O
Isomeric SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1C[C@H](C2=O)O)CCC4=C3C=CC(=C4)O
InChI 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
InChI Key WPOCIZJTELRQMF-QFXBJFAPSA-N
Bioactivity Comments
16α-hydroxyestrone interacts with estrogen receptors [5], has uterotrophic effects and decreases circulating luteinizing hormone concentrations in rats [1,3]. Overproduction of 16α-hydroxyestrone has been implicated in the pathophysiology of breast cancer [2,4].
Selectivity at nuclear hormone receptors
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
Estrogen receptor-α Hs Agonist Agonist 9.1 – 9.1 pKd - 5
pKd 9.1 – 9.1 (Kd 9x10-10 – 7x10-10 M) [5]
Description: Apparent equilibrium dissociation constant determined for cytosolic estrogen binding sites in MCF-7 cells