GAT211   Click here for help

GtoPdb Ligand ID: 10272

Compound class: Synthetic organic
Comment: GAT211 is an agonist and positive allosteric modulator (ago-PAM) of cannabinoid receptor 1 (CB1R) and is a racemic mixture of GAT228 (R-enantiomer) and GAT229 (S-enantiomer), each of which contribute different components of GAT211's molecular pharmacology. GAT228 provides the CB1R partial agonist activity, whereas PAM activity resides with GAT229 [1].

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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 0
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 58.93
Molecular weight 342.14
XLogP 5.6
No. Lipinski's rules broken 1

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 [O-][N+](=O)CC(c1c([nH]c2c1cccc2)c1ccccc1)c1ccccc1
Isomeric SMILES [O-][N+](=O)CC(c1c([nH]c2c1cccc2)c1ccccc1)c1ccccc1
InChI InChI=1S/C22H18N2O2/c25-24(26)15-19(16-9-3-1-4-10-16)21-18-13-7-8-14-20(18)23-22(21)17-11-5-2-6-12-17/h1-14,19,23H,15H2
InChI Key OHZDCJJHWPHZJD-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/)
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
3-(2-nitro-1-phenylethyl)-2-phenyl-1H-indole
Database Links Click here for help
Specialist databases
GPCRdb Ligand GAT211
Other databases
GtoPdb PubChem SID 381744953
PubChem CID 4402318
Search Google for chemical match using the InChIKey OHZDCJJHWPHZJD-UHFFFAOYSA-N
Search Google for chemicals with the same backbone OHZDCJJHWPHZJD
UniChem Compound Search for chemical match using the InChIKey OHZDCJJHWPHZJD-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey OHZDCJJHWPHZJD-UHFFFAOYSA-N

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MedChemExpress
GAT211 (links to external site)
Cat. No. HY-113689