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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2D Structure
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Physico-chemical Properties
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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
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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)
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
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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]