2-Methoxyestradiol   Click here for help

GtoPdb Ligand ID: 12058

Synonyms: 2-ME2 | 2-MeO-E2 | 2ME2 | NSC-659853 | Panzem®
PDB Ligand
Compound class: Metabolite
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.
Click here for help
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 1
Topological polar surface area 49.69
Molecular weight 302.19
XLogP 3.88
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help
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
InChI Key CQOQDQWUFQDJMK-SSTWWWIQSA-N
Classification Click here for help
Compound class Metabolite
IUPAC Name Click here for help
(8R,9S,13S,14S,17S)-2-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol
Synonyms Click here for help
2-ME2 | 2-MeO-E2 | 2ME2 | NSC-659853 | Panzem®
Database Links Click here for help
Specialist databases
GPCRdb Ligand 2-Methoxyestradiol
Other databases
BindingDB Ligand 50060957
CAS Registry No. 362-07-2 (source: PubChem)
ChEMBL Ligand CHEMBL299613
DrugBank Ligand DB02342
GtoPdb PubChem SID 472319180
LIPID MAPS LMST02010035
PubChem CID 66414
RCSB PDB Ligand ESM, ESM
Search Google for chemical match using the InChIKey CQOQDQWUFQDJMK-SSTWWWIQSA-N
Search Google for chemicals with the same backbone CQOQDQWUFQDJMK
UniChem Compound Search for chemical match using the InChIKey CQOQDQWUFQDJMK-SSTWWWIQSA-N
UniChem Connectivity Search for chemical match using the InChIKey CQOQDQWUFQDJMK-SSTWWWIQSA-N