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.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

2-Methoxyestradiol is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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
InChI Key CQOQDQWUFQDJMK-SSTWWWIQSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
2-Methoxyestradiol was evaluated in Phase 2 studies for anti-tumour activity in solid and haematologic cancers, but development was terminated.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT00028821 2-Methoxyestradiol in Treating Patients With Advanced Solid Tumors Phase 1 Interventional National Cancer Institute (NCI)
NCT00481455 Phase 2 Study of Panzem Nanocrystal Colloidal Dispersion (NCD) in Combination With Fixed-Dose Temozolomide to Patients With Recurrent Glioblastoma Multiforme (GBM) Phase 2 Interventional CASI Pharmaceuticals, Inc.
NCT00394810 Efficacy and Pharmacodynamic Study of Panzem® NCD in Patients With Hormone-Refractory Prostate Cancer Phase 2 Interventional CASI Pharmaceuticals, Inc. 8