compound 3a [Badolato et al., 2019]   Click here for help

GtoPdb Ligand ID: 10345

Compound class: Synthetic organic
Comment: Compound 3a has been reported as an inverse agonist of GPR55 [1]. It exhibits antiproliferative activity against breast cancer cells in vitro (e.g. MDA-MB-231 IC50 2700 nM, MCF10A IC50 3700 nM).
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 4
Hydrogen bond donors 2
Rotatable bonds 1
Topological polar surface area 87.07
Molecular weight 309.04
XLogP 1.46
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 ClC1=C(N2CCOCC2)C(=O)c2c(C1=O)c(O)ccc2O
Isomeric SMILES ClC1=C(N2CCOCC2)C(=O)c2c(C1=O)c(O)ccc2O
InChI InChI=1S/C14H12ClNO5/c15-11-12(16-3-5-21-6-4-16)14(20)10-8(18)2-1-7(17)9(10)13(11)19/h1-2,17-18H,3-6H2
InChI Key FTMCZTSKCXEXCO-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. Badolato M, Carullo G, Caroleo MC, Cione E, Aiello F, Manetti F. (2019)
Discovery of 1,4-Naphthoquinones as a New Class of Antiproliferative Agents Targeting GPR55.
ACS Med Chem Lett, 10 (4): 402-406. DOI: 10.1021/acsmedchemlett.8b00333 [PMID:30996770]