estriol   Click here for help

GtoPdb Ligand ID: 2821

Synonyms: Trimesta®
Approved drug PDB Ligand
estriol is an approved drug
Compound class: Metabolite
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
SMILES / InChI / InChIKey
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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
InChI Key PROQIPRRNZUXQM-ZXXIGWHRSA-N
References
1. 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]