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Compound Detail

CHEMBL594192

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Nc1ccc2c(c1)/C(=C1/Nc3ccccc3C1=O)C(=O)N2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL594192
Phase Preclinical
Structure Type MOL
InChI Key UKVQMBJHWHGXOI-YPKPFQOOSA-N
12
Targets
14
Activities
1
Assay Types
0
PK Parameters
14
Publications
0
Known Names

Molecular Properties

277.3
MW (Da)
2.24
ALogP
4
HBA
3
HBD
84.2
PSA (Ų)
0.51
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C16H11N3O2
MW 277.28
Aromatic Rings 2
Heavy Atoms 21
NP-Likeness 0.32

Activity Summary

IC50 14 meas. best 7.1

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Glycogen synthase kinase-3
CHEMBL2366565
 IC50 7.1 7.1 80.0 1
Receptor-type tyrosine-protein kinase FLT3
CHEMBL1974
 IC50 6.45 6.45 359.0 1
Cyclin-dependent kinase 5/CDK5 activator 1
CHEMBL1907600
 IC50 6.23 6.23 590.0 1
Unchecked
CHEMBL612545
 IC50 6.19 6.005 650.0 2
Serine/threonine-protein kinase 17B
CHEMBL3980
 IC50 5.85 5.85 1400.0 1
Caco-2
CHEMBL614058
 IC50 5.7 5.7 2000.0 1
Dual specificity tyrosine-phosphorylation-regulated kinase 1A
CHEMBL5508
 IC50 5.6 5.6 2500.0 1
MV4-11
CHEMBL613835
 IC50 5.37 5.37 4300.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.33 5.015 4670.0 2
PC-3
CHEMBL390
 IC50 5.3 5.3 5000.0 1
Huh-7
CHEMBL614039
 IC50 5.22 5.22 6000.0 1
HCT-116
CHEMBL394
 IC50 4.82 4.82 15000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Glycogen synthase kinase-3 IC50 = 80.0 nM 7.1 Inhibition of porcine brain GSK3alpha/beta assessed as [gamma-33P]ATP incorporat... 19665384
Receptor-type tyrosine-protein kinase FLT3 IC50 = 359.0 nM 6.45 Inhibition of FLT3 by HTRF assay 20153646
Cyclin-dependent kinase 5/CDK5 activator 1 IC50 = 590.0 nM 6.23 Inhibition of GST-fused CDK5/p25 expressed in Escherichia coli assessed as [gamm... 19665384
Unchecked IC50 = 650.0 nM 6.19 Inhibition of porcine brain CK1 assessed as [gamma-33P]ATP incorporation after 1... 19665384
Serine/threonine-protein kinase 17B IC50 = 1400.0 nM 5.85 Inhibition of DRAK2 (unknown origin) using MRLC3 peptide as substrate incubated ... 27106709
Unchecked IC50 = 1500.0 nM 5.82 Inhibition of Marthasterias glacialis CDK1/cyclin-B assessed as [gamma-33P]ATP i... 19665384
Caco-2 IC50 = 2000.0 nM 5.7 Antiproliferative activity against human Caco-2 cells after 72 hrs by imaging an... 19665384
Dual specificity tyrosine-phosphorylation-regulated kinase 1A IC50 = 2500.0 nM 5.6 Inhibition of GST-fused rat recombinant DYRK1A expressed in Escherichia coli ass... 19665384
MV4-11 IC50 = 4300.0 nM 5.37 Antiproliferative activity against wild type FLT3 expressing human MV411 cells a... 20153646
NON-PROTEIN TARGET IC50 = 4670.0 nM 5.33 Antiproliferative activity against human RS4:11 cells having FLT3-ITD mutation a... 20153646
PC-3 IC50 = 5000.0 nM 5.3 Antiproliferative activity against human PC3 cells after 72 hrs by imaging analy... 19665384
Huh-7 IC50 = 6000.0 nM 5.22 Antiproliferative activity against human HuH7 cells after 72 hrs by imaging anal... 19665384
HCT-116 IC50 = 15000.0 nM 4.82 Antiproliferative activity against human HCT116 cells after 72 hrs by imaging an... 19665384
NON-PROTEIN TARGET IC50 = 20000.0 nM 4.7 Antiproliferative activity against human NCI/ADR cells after 72 hrs by imaging a... 19665384

Literature References

PubMed DOI Target Context # Activities
19665384 10.1016/j.bmc.2009.07.051 Unchecked 2
19665384 10.1016/j.bmc.2009.07.051 Glycogen synthase kinase-3 1
19665384 10.1016/j.bmc.2009.07.051 Cyclin-dependent kinase 5/CDK5 activator 1 1
19665384 10.1016/j.bmc.2009.07.051 Dual specificity tyrosine-phosphorylation-regulated kinase 1A 1
19665384 10.1016/j.bmc.2009.07.051 Caco-2 1
19665384 10.1016/j.bmc.2009.07.051 PC-3 1
19665384 10.1016/j.bmc.2009.07.051 Huh-7 1
19665384 10.1016/j.bmc.2009.07.051 HCT-116 1
19665384 10.1016/j.bmc.2009.07.051 NON-PROTEIN TARGET 1
19665384 10.1016/j.bmc.2009.07.051 ADMET 1
20153646 10.1016/j.bmcl.2010.01.039 Receptor-type tyrosine-protein kinase FLT3 1
20153646 10.1016/j.bmcl.2010.01.039 NON-PROTEIN TARGET 1
20153646 10.1016/j.bmcl.2010.01.039 MV4-11 1
27106709 10.1016/j.bmcl.2016.03.111 Serine/threonine-protein kinase 17B 1

Data from ChEMBL 36 via Core Engine