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
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2D Structure
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Physico-chemical Properties
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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
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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
References
1. Coward P, Lee D, Hull MV, Lehmann JM. (2001)
4-Hydroxytamoxifen binds to and deactivates the estrogen-related receptor gamma.
Proc Natl Acad Sci USA, 98 (15): 8880-4. [PMID:11447273]
2. Kuiper GG, Carlsson B, Grandien K, Enmark E, Häggblad J, Nilsson S, Gustafsson JA. (1997)
Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta.
Endocrinology, 138 (3): 863-70. [PMID:9048584]
3. Tremblay GB, Kunath T, Bergeron D, Lapointe L, Champigny C, Bader JA, Rossant J, Giguère V. (2001)
Diethylstilbestrol regulates trophoblast stem cell differentiation as a ligand of orphan nuclear receptor ERR beta.
Genes Dev, 15 (7): 833-8. [PMID:11297507]