laquinimod   Click here for help

GtoPdb Ligand ID: 7639

Synonyms: ABR-215062 | TV-5600
Compound class: Synthetic organic
Comment: Laquinimod is an experimental immunomodulator being investigated as an oral treatment for multiple sclerosis (MS) [2-5].

laquinimod 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 3
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 62.54
Molecular weight 356.09
XLogP 5.05
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 CCN(C(=O)c1c(O)c2c(Cl)cccc2n(c1=O)C)c1ccccc1
Isomeric SMILES CCN(C(=O)c1c(O)c2c(Cl)cccc2n(c1=O)C)c1ccccc1
InChI InChI=1S/C19H17ClN2O3/c1-3-22(12-8-5-4-6-9-12)19(25)16-17(23)15-13(20)10-7-11-14(15)21(2)18(16)24/h4-11,23H,3H2,1-2H3
InChI Key GKWPCEFFIHSJOE-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
5-chloro-N-ethyl-4-hydroxy-1-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide
Synonyms Click here for help
ABR-215062 | TV-5600
Database Links Click here for help
CAS Registry No. 248281-84-7 (source: SciFinder)
ChEMBL Ligand CHEMBL66092
DrugCentral Ligand 4825
GtoPdb PubChem SID 223365974
PubChem CID 54677946
Search Google for chemical match using the InChIKey GKWPCEFFIHSJOE-UHFFFAOYSA-N
Search Google for chemicals with the same backbone GKWPCEFFIHSJOE
UniChem Compound Search for chemical match using the InChIKey GKWPCEFFIHSJOE-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey GKWPCEFFIHSJOE-UHFFFAOYSA-N
Wikipedia Laquinimod

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MedChemExpress
Laquinimod (links to external site)
Cat. No. HY-13010