diethylstilbestrol   Click here for help

GtoPdb Ligand ID: 2801

Synonyms: stilboestrol
Approved drug PDB Ligand
diethylstilbestrol is an approved drug (FDA (1973))
Comment: Estrogen receptor alpha agonist
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 0
Hydrogen bond donors 2
Rotatable bonds 4
Topological polar surface area 40.46
Molecular weight 268.15
XLogP 5.56
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES CCC(=C(c1ccc(cc1)O)CC)c1ccc(cc1)O
Isomeric SMILES CC/C(=C(\c1ccc(cc1)O)/CC)/c1ccc(cc1)O
InChI InChI=1S/C18H20O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h5-12,19-20H,3-4H2,1-2H3/b18-17+
InChI Key RGLYKWWBQGJZGM-ISLYRVAYSA-N
Selectivity at nuclear hormone receptors
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
Estrogen receptor-α Primary target of this compound Hs Agonist Agonist 10.4 pKi - 2
pKi 10.4 [2]
Estrogen receptor-β Hs Agonist Agonist 9.8 pKi - 2
pKi 9.8 [2]
Estrogen-related receptor-α Mm Antagonist Antagonist 4.8 – 5.3 pIC50 - 3
pIC50 4.8 – 5.3 [3]
Estrogen-related receptor-β Hs Antagonist Antagonist 4.8 – 5.3 pIC50 - 3
pIC50 4.8 – 5.3 [3]
Estrogen-related receptor-γ Hs Antagonist Antagonist 4.8 – 5.3 pIC50 - 1,3
pIC50 4.8 – 5.3 [1,3]