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.
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2D Structure
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Physico-chemical Properties
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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
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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
Natural/Endogenous Targets
Target
Estrogen receptor-α
Estrogen receptor-β
GPER
Pregnane X receptor
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
GPER Ligand is endogenous in the given species Hs Agonist Full agonist 8.2 – 8.5 pKi - 3-4
pKi 8.2 – 8.5 [3-4]
Selectivity at ion channels
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
KCa1.1 Hs Activator - 5.6 pEC50 - 5
pEC50 5.6 [5]
Selectivity at nuclear hormone receptors
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
Estrogen receptor-α Primary target of this compound Ligand is endogenous in the given species Hs Agonist Agonist 9.8 pKi - 2
pKi 9.8 [2]
Estrogen receptor-β Ligand is endogenous in the given species Hs Agonist Agonist 9.3 pKi - 2
pKi 9.3 [2]
Pregnane X receptor Ligand is endogenous in the given species Hs Agonist Agonist - - - 1
[1]
Targets where the ligand is described in the comment field
Target Comment
Ligand mentioned in the following text fields