compound 33 [PMID: 19364658]   Click here for help

GtoPdb Ligand ID: 8163

Compound class: Synthetic organic
Comment: Compound 33 is a small molecule analogue designed and assessed for inhibitory activity against mitogen activated protein kinase-activated protein kinase 2 (MK2) [1].
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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
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 7
Hydrogen bond donors 4
Rotatable bonds 6
Topological polar surface area 134.41
Molecular weight 338.1
XLogP 0.44
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 Oc1cccc(c1)C(C(=O)N)NC1=C(C(=O)C1=O)Nc1ccncc1
Isomeric SMILES Oc1cccc(c1)C(C(=O)N)NC1=C(C(=O)C1=O)Nc1ccncc1
InChI InChI=1S/C17H14N4O4/c18-17(25)12(9-2-1-3-11(22)8-9)21-14-13(15(23)16(14)24)20-10-4-6-19-7-5-10/h1-8,12,21-22H,(H2,18,25)(H,19,20)
InChI Key GPXKVULNYYNGDP-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/)
Bioactivity Comments
Although compound 33 was designed as a MK2 inhibitor it has more potent off-target effects at other kinases in a kinase selectivity screen [1]. The highest potency effects are shown in the table below. We tag MK2 as the primary interaction as this was the intended molecular target.
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
Rho associated coiled-coil containing protein kinase 1 Hs Inhibitor Inhibition 7.2 pIC50 - 1
⤷ pIC50 7.2 (IC50 6x10-8 M) [1]
checkpoint kinase 1 Hs Inhibitor Inhibition 7.1 pIC50 - 1
⤷ pIC50 7.1 (IC50 9x10-8 M) [1]
casein kinase 1 gamma 1 Hs Inhibitor Inhibition 6.8 pIC50 - 1
⤷ pIC50 6.8 (IC50 1.6x10-7 M) [1]
protein kinase A Hs Inhibitor Inhibition 6.6 pIC50 - 1
⤷ pIC50 6.6 (IC50 2.7x10-7 M) [1]
ribosomal protein S6 kinase A1 Hs Inhibitor Inhibition 6.5 pIC50 - 1
⤷ pIC50 6.5 (IC50 2.9x10-7 M) [1]
MAPK activated protein kinase 2 Primary target of this compound Hs Inhibitor Inhibition 6.4 pIC50 - 1
⤷ pIC50 6.4 (IC50 3.9x10-7 M) [1]