17β-estradiol   Click here for help

GtoPdb Ligand ID: 1013

Abbreviated name: E2
Synonyms: estrogen | oestrodiol | oestrogen
Approved drug PDB Ligand
17β-estradiol is an approved drug (FDA (1954, prior history unavailable))
Comment: 17β-estradiol is the predominant form of circulating estrogen and is the endogenous agonist of the estrogen receptor α. In pre-menopausal women 17β-estradiol is mainly produced by the ovaries and placenta and is produced by adipose tissue in men and postmenopausal women.
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: estradiol

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 1
Hydrogen bond donors 2
Rotatable bonds 0
Topological polar surface area 40.46
Molecular weight 272.18
XLogP 4.23
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES Oc1ccc2c(c1)CCC1C2CCC2(C1CCC2O)C
Isomeric SMILES Oc1ccc2c(c1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2O)C
InChI InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3/t14-,15-,16+,17+,18+/m1/s1
InChI Key VOXZDWNPVJITMN-ZBRFXRBCSA-N
Classification Click here for help
Compound class Metabolite or derivative
Approved drug? Yes (FDA (1954, prior history unavailable))
Prodrug estradiol valerate
IUPAC Name Click here for help
(8R,9S,13S,14S,17S)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol
International Nonproprietary Names Click here for help
INN number INN
406 estradiol
Synonyms Click here for help
estrogen | oestrodiol | oestrogen
Database Links Click here for help
CAS Registry No. 50-28-2 (source: DrugBank)
ChEBI CHEBI:16469
ChEMBL Ligand CHEMBL135
DrugBank Ligand DB00783
DrugCentral Ligand 1057
GtoPdb PubChem SID 135651381
PubChem CID 5757
RCSB PDB Ligand EST
Search Google for chemical match using the InChIKey VOXZDWNPVJITMN-ZBRFXRBCSA-N
Search Google for chemicals with the same backbone VOXZDWNPVJITMN
Search PubMed clinical trials estradiol
Search PubMed titles estradiol
Search PubMed titles/abstracts estradiol
Search UniChem for chemical match using the InChIKey VOXZDWNPVJITMN-ZBRFXRBCSA-N
Search UniChem for chemicals with the same backbone VOXZDWNPVJITMN
SynPHARM 6509 (in complex with Estrogen receptor-α)
6522 (in complex with Estrogen receptor-β)
Wikipedia Estradiol

Product suppliers

View disclaimer

Tocris
β-Estradiol
Cat. No. 2824