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Compound Detail

CHEMBL478649

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Cc1ccc(C(=O)NC2CC2)cc1-c1ccc(C(=O)NCC2CC2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL478649
Phase Preclinical
Structure Type MOL
InChI Key BOPSUAHGQHFKGG-UHFFFAOYSA-N
6
Targets
20
Activities
2
Assay Types
3
PK Parameters
20
Publications
0
Known Names

Molecular Properties

348.4
MW (Da)
3.69
ALogP
2
HBA
2
HBD
58.2
PSA (Ų)
0.84
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C22H24N2O2
MW 348.45
Aromatic Rings 2
Heavy Atoms 26
NP-Likeness -1.00

Activity Summary

IC50 13 meas. best 7.75
Ki 7 meas. best 8.05

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Mitogen-activated protein kinase 14
CHEMBL260
 Ki 8.05 7.9517 9.0 6
Mitogen-activated protein kinase 14
CHEMBL260
 IC50 7.75 6.898 18.0 5
Mitogen-activated protein kinase 11
CHEMBL3961
 Ki 7.62 7.62 24.0 1
Heat shock protein beta-1
CHEMBL5976
 IC50 7.28 7.28 53.0 1
PBMC
CHEMBL613107
 IC50 6.6 6.6 250.0 2
Blood
CHEMBL613416
 IC50 6.0 6.0 1000.0 2
Cytochrome P450 2C9
CHEMBL3397
 IC50 5.4 5.38 3981.1 2

Pharmacokinetic Data

Parameter Value Units Species
CL 6.0 mL.min-1.kg-1 Rattus norvegicus
F 113.0 % Rattus norvegicus
T1/2 1.3 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Mitogen-activated protein kinase 14 Ki = 9.0 nM 8.05 Inhibition of human recombinant p38alpha-mediated ATF2 phosphorylation by TR-FRE... 18602262
Mitogen-activated protein kinase 14 Ki = 10.0 nM 8.0 Inhibition of human recombinant His-tagged p38alpha-mediated ATF2 phosphorylatio... 18614366
Mitogen-activated protein kinase 14 Ki = 12.0 nM 7.92 Inhibition of P38alpha MAPK (unknown origin) 31445234
Mitogen-activated protein kinase 14 Ki = 12.0 nM 7.92 Displacement of rhodamine-green labelled (2-(6-amino-3-imino-3H-xanthen-9-yl)-5-... 18614366
Mitogen-activated protein kinase 14 Ki = 12.0 nM 7.92 Displacement of rhodamine-green labeled (2-(6-amino-3-imino-3H-xanthen-9-yl)-5-{... 18602262
Mitogen-activated protein kinase 14 Ki = 12.59 nM 7.9 Inhibition of GST-tagged p38alpha by fluorescence polarization method 19772287
Mitogen-activated protein kinase 14 IC50 = 18.0 nM 7.75 Inhibition of p38alpha phosphorylation in IL-1-alpha-stimulated HLF cells 18602262
Mitogen-activated protein kinase 11 Ki = 24.0 nM 7.62 Displacement of rhodamine-green labelled (2-(6-amino-3-imino-3H-xanthen-9-yl)-5-... 18614366
Heat shock protein beta-1 IC50 = 53.0 nM 7.28 Inhibition of HSP27 phosphorylation in IL-1-alpha-stimulated HLF cells 18602262
Mitogen-activated protein kinase 14 IC50 = 75.0 nM 7.12 Inhibition of P38alpha MAPK (unknown origin) 31445234
Mitogen-activated protein kinase 14 IC50 = 75.0 nM 7.12 Displacement of rhodamine-green labelled (2-(6-amino-3-imino-3H-xanthen-9-yl)-5-... 18614366
Mitogen-activated protein kinase 14 IC50 = 199.53 nM 6.7 Inhibition of p38alpha-dependent TNFalpha production in human PBMC preincubated ... 19772287
PBMC IC50 = 250.0 nM 6.6 Inhibition of LPS-stimulated TNFalpha release in human PBMC by ELISA 18602262
PBMC IC50 = 250.0 nM 6.6 Inhibition of LPS-stimulated TNFalpha release in human PBMCs 18789685
Blood IC50 = 1000.0 nM 6.0 Inhibition of LPS-stimulated TNF alpha release in human whole blood cells by ELI... 18614366
Blood IC50 = 1000.0 nM 6.0 Inhibition of LPS-stimulated TNFalpha release in human whole blood 18789685
Mitogen-activated protein kinase 14 IC50 = 1584.89 nM 5.8 Inhibition of p38alpha-dependent TNFalpha production in human whole blood preinc... 19772287
Cytochrome P450 2C9 IC50 = 3981.07 nM 5.4 Inhibition of human CYP2C9 expressed in Escherichia coli by fluorimetric assay 19772287
Cytochrome P450 2C9 IC50 = 4400.0 nM 5.36 Inhibition of human recombinant CYP2C9 transfected in Escherichia coli co-expres... 18614366

Literature References

PubMed DOI Target Context # Activities
18614366 10.1016/j.bmcl.2008.06.048 Unchecked 9
19035792 10.1021/jm8011036 Unchecked 8
18614366 10.1016/j.bmcl.2008.06.048 Rattus norvegicus 5
18602262 10.1016/j.bmcl.2008.06.028 Mitogen-activated protein kinase 14 4
18614366 10.1016/j.bmcl.2008.06.048 Mitogen-activated protein kinase 14 3
19772287 10.1021/jm9004779 Mitogen-activated protein kinase 14 3
31445234 10.1016/j.ejmech.2019.111624 Mitogen-activated protein kinase 14 2
18614366 10.1016/j.bmcl.2008.06.048 Mus musculus 2
19035792 10.1021/jm8011036 Atypical kinase COQ8B, mitochondrial 2
19035792 10.1021/jm8011036 Ribosomal protein S6 kinase alpha-4 2
19035792 10.1021/jm8011036 Mitogen-activated protein kinase kinase kinase kinase 4 2
18602262 10.1016/j.bmcl.2008.06.028 Unchecked 2
18789685 10.1016/j.bmcl.2008.08.051 Mitogen-activated protein kinase 10 1
18602262 10.1016/j.bmcl.2008.06.028 Mitogen-activated protein kinase 11 1
18789685 10.1016/j.bmcl.2008.08.051 Tyrosine-protein kinase Lck 1
18789685 10.1016/j.bmcl.2008.08.051 Epidermal growth factor receptor 1
18789685 10.1016/j.bmcl.2008.08.051 Macrophage colony-stimulating factor 1 receptor 1
18789685 10.1016/j.bmcl.2008.08.051 Dual specificity mitogen-activated protein kinase kinase 1 1
18789685 10.1016/j.bmcl.2008.08.051 Blood 1
18789685 10.1016/j.bmcl.2008.08.051 Vascular endothelial growth factor receptor 2 1

Data from ChEMBL 36 via Core Engine