2-Methoxyestradiol   Click here for help

GtoPdb Ligand ID: 12058

Synonyms: 2-ME2 | 2-MeO-E2 | 2ME2 | NSC-659853 | Panzem®
PDB Ligand
Comment: 2-Methoxyestradiol is a high-affinity agonist of the G protein-coupled estrogen receptor (GPER) [6,9]. It is an endogenous metabolite of estradiol (17β-estradiol) and 2-hydroxyestradiol. 2-Methoxyestradiol has anti-angogenic and vasodilatory activities [3-5], but it has limited oral bioavailability [1,7] and failed to show significant efficacy in clinical trials.
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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 1
Topological polar surface area 49.69
Molecular weight 302.19
XLogP 3.88
No. Lipinski's rules broken 0
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Canonical SMILES COc1cc2c(cc1O)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2O)C
Isomeric SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCc1cc(c(cc31)OC)O
InChI InChI=1S/C19H26O3/c1-19-8-7-12-13(15(19)5-6-18(19)21)4-3-11-9-16(20)17(22-2)10-14(11)12/h9-10,12-13,15,18,20-21H,3-8H2,1-2H3/t12-,13+,15-,18-,19-/m0/s1
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
GPER Hs Agonist Agonist 8.0 pKd - 2
pKd 8.0 (Kd 1x10-8 M) [2]
Description: Specific binding affinity of [3H]2ME2 to GPER in vitro