estriol   Click here for help

GtoPdb Ligand ID: 2821

Synonyms: Trimesta®
Approved drug PDB Ligand
estriol is an approved drug
Comment: Estriol (E3) is one of the three main endogenous human estrogens. E3 is only produced in significant amounts during pregnancy, being synthesised in the placenta from 16-hydroxydehydroepiandrosterone sulfate (16-OH DHEAS), an androgen of fetal origin.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 3
Rotatable bonds 0
Topological polar surface area 60.69
Molecular weight 288.17
XLogP 3.63
No. Lipinski's rules broken 0
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Canonical SMILES Oc1ccc2c(c1)CCC1C2CCC2(C1CC(C2O)O)C
Isomeric SMILES Oc1ccc2c(c1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1C[C@H]([C@@H]2O)O)C
InChI InChI=1S/C18H24O3/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/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,17+,18+/m1/s1
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Summary of Clinical Use Click here for help
The US FDA does not approve marketing of estriol, although this compound has been approved and marketed in Europe and Asia for >40 years for the treatment of post-menopausal hot flashes.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Estriol binds to its the estrogen receptor α, acting as a transcription factor to target gene transcription and protein synthesis.