WAY200070   Click here for help

GtoPdb Ligand ID: 4052

Synonyms: WAY 200070 | WAY-200070
Compound class: Synthetic organic
Comment: WAY200070 is an estrogen receptor β (ERβ) selective agonist (68-fold selective over ERα) [1-2]. It displays antianxiolytic and antidepressive effects in vivo [2].
The PubChem CID above represents an alternative tautomer which is an intermediate of the equilibrium shift between phenol and phenolate undergone by the phenol group.
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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

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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 66.49
Molecular weight 304.97
XLogP 3.15
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 Oc1ccc(cc1)c1oc2c(n1)cc(cc2Br)O
Isomeric SMILES Oc1ccc(cc1)c1oc2c(n1)cc(cc2Br)O
InChI InChI=1S/C13H8BrNO3/c14-10-5-9(17)6-11-12(10)18-13(15-11)7-1-3-8(16)4-2-7/h1-6,16-17H
InChI Key BAAILVWEAXFTSF-UHFFFAOYSA-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/)
References
1. Clipperton AE, Spinato JM, Chernets C, Pfaff DW, Choleris E. (2008)
Differential effects of estrogen receptor alpha and beta specific agonists on social learning of food preferences in female mice.
Neuropsychopharmacology, 33 (10): 2362-75. [PMID:18004284]
2. Hughes ZA, Liu F, Platt BJ, Dwyer JM, Pulicicchio CM, Zhang G, Schechter LE, Rosenzweig-Lipson S, Day M. (2008)
WAY-200070, a selective agonist of estrogen receptor beta as a potential novel anxiolytic/antidepressant agent.
Neuropharmacology, 54 (7): 1136-42. [PMID:18423777]
3. Malamas MS, Manas ES, McDevitt RE, Gunawan I, Xu ZB, Collini MD, Miller CP, Dinh T, Henderson RA, Keith JC et al.. (2004)
Design and synthesis of aryl diphenolic azoles as potent and selective estrogen receptor-beta ligands.
J Med Chem, 47 (21): 5021-40. [PMID:15456246]