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Compound Detail

CHEMBL393545

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O=C1NC(=O)c2c1c1c3ccccc3[nH]c1c1cccn21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL393545
Phase Preclinical
Structure Type MOL
InChI Key FDOURPSVRVOTSM-UHFFFAOYSA-N
15
Targets
19
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

275.3
MW (Da)
2.46
ALogP
3
HBA
2
HBD
66.4
PSA (Ų)
0.48
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 C16H9N3O2
MW 275.27
Aromatic Rings 4
Heavy Atoms 21
NP-Likeness -0.19

Activity Summary

IC50 19 meas. best 7.62

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Serine/threonine-protein kinase Chk1
CHEMBL4630
 IC50 7.62 7.62 24.0 2
Dual specificity protein kinase CLK1
CHEMBL1075280
 IC50 6.28 6.28 520.0 1
Glycogen synthase kinase-3
CHEMBL2366565
 IC50 6.24 6.24 570.0 1
Dual specificity tyrosine-phosphorylation-regulated kinase 1A
CHEMBL5508
 IC50 5.89 5.89 1300.0 1
DU-145
CHEMBL613508
 IC50 5.85 5.85 1400.0 1
A549
CHEMBL392
 IC50 5.7 5.225 2000.0 2
Cyclin-dependent kinase 5/CDK5 activator 1
CHEMBL1907600
 IC50 5.68 5.68 2100.0 1
L1210
CHEMBL386
 IC50 5.51 5.51 3100.0 1
HT-29
CHEMBL384
 IC50 5.48 5.48 3300.0 1
Unchecked
CHEMBL612545
 IC50 5.0 5.0 10000.0 1
LoVo
CHEMBL614721
 IC50 4.96 4.96 11000.0 1
B16-F10
CHEMBL612656
 IC50 4.72 4.72 19000.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.48 4.2933 33000.0 3
MCF7
CHEMBL387
 IC50 4.31 4.31 49000.0 1
PC-3
CHEMBL390
 IC50 4.3 4.3 50000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Serine/threonine-protein kinase Chk1 IC50 = 24.0 nM 7.62 Inhibition of human Chk1 22809559
Serine/threonine-protein kinase Chk1 IC50 = 24.0 nM 7.62 Inhibition of human Chk1 17582773
Dual specificity protein kinase CLK1 IC50 = 520.0 nM 6.28 Inhibition of GST-fused mouse recombinant CLK1 expressed in Escherichia coli usi... 22809559
Glycogen synthase kinase-3 IC50 = 570.0 nM 6.24 Inhibition of porcine brain GSK3alpha/beta using GS1 as substrate 22809559
Dual specificity tyrosine-phosphorylation-regulated kinase 1A IC50 = 1300.0 nM 5.89 Inhibition of GST-fused rat recombinant DYRK1A expressed in Escherichia coli usi... 22809559
DU-145 IC50 = 1400.0 nM 5.85 Antiproliferative activity against human DU145 cells after 4 hrs by microculture... 17582773
A549 IC50 = 2000.0 nM 5.7 Antiproliferative activity against human A549 cells after 4 hrs by microculture ... 17582773
Cyclin-dependent kinase 5/CDK5 activator 1 IC50 = 2100.0 nM 5.68 Inhibition of human recombinant CDK5/p25 22809559
L1210 IC50 = 3100.0 nM 5.51 Antiproliferative activity against mouse L1210 cells after 4 hrs by microculture... 17582773
HT-29 IC50 = 3300.0 nM 5.48 Antiproliferative activity against human HT29 cells after 4 hrs by microculture ... 17582773
Unchecked IC50 = 10000.0 nM 5.0 Inhibition of porcine brain CK1delta/epsilon using CKS peptide as substrate 22809559
LoVo IC50 = 11000.0 nM 4.96 Cytotoxicity against human LoVo cells after 72 hrs by MTT assay 22809559
A549 IC50 = 18000.0 nM 4.75 Cytotoxicity against human A549 cells after 72 hrs by MTT assay 22809559
B16-F10 IC50 = 19000.0 nM 4.72 Cytotoxicity against mouse B16F10 cells after 72 hrs by MTT assay 22809559
NON-PROTEIN TARGET IC50 = 33000.0 nM 4.48 Cytotoxicity against p53-mutant human U373 cells after 72 hrs by MTT assay 22809559
MCF7 IC50 = 49000.0 nM 4.31 Cytotoxicity against human MCF7 cells after 72 hrs by MTT assay 22809559
PC-3 IC50 = 50000.0 nM 4.3 Cytotoxicity against human PC3 cells after 72 hrs by MTT assay 22809559
NON-PROTEIN TARGET IC50 = 52000.0 nM 4.28 Cytotoxicity against human Hs683 cells after 72 hrs by MTT assay 22809559
NON-PROTEIN TARGET IC50 = 75000.0 nM 4.12 Cytotoxicity against human OE21 cells after 72 hrs by MTT assay 22809559

Literature References

PubMed DOI Target Context # Activities
22809559 10.1016/j.ejmech.2012.06.012 NON-PROTEIN TARGET 3
17582773 10.1016/j.bmc.2007.05.073 DNA topoisomerase 1 2
22809559 10.1016/j.ejmech.2012.06.012 A549 2
17582773 10.1016/j.bmc.2007.05.073 Serine/threonine-protein kinase Chk1 2
22809559 10.1016/j.ejmech.2012.06.012 LoVo 1
33831559 10.1016/j.bmcl.2021.128009 HCT-116 1
22809559 10.1016/j.ejmech.2012.06.012 Glycogen synthase kinase-3 1
22809559 10.1016/j.ejmech.2012.06.012 Dual specificity tyrosine-phosphorylation-regulated kinase 1A 1
22809559 10.1016/j.ejmech.2012.06.012 Dual specificity protein kinase CLK1 1
22809559 10.1016/j.ejmech.2012.06.012 Unchecked 1
22809559 10.1016/j.ejmech.2012.06.012 Cyclin-dependent kinase 5/CDK5 activator 1 1
22809559 10.1016/j.ejmech.2012.06.012 HCT-116 1
22809559 10.1016/j.ejmech.2012.06.012 B16-F10 1
22809559 10.1016/j.ejmech.2012.06.012 PC-3 1
22809559 10.1016/j.ejmech.2012.06.012 MCF7 1
17582773 10.1016/j.bmc.2007.05.073 Unchecked 1
17582773 10.1016/j.bmc.2007.05.073 Proto-oncogene tyrosine-protein kinase Src 1
17582773 10.1016/j.bmc.2007.05.073 HT-29 1
17582773 10.1016/j.bmc.2007.05.073 A549 1
17582773 10.1016/j.bmc.2007.05.073 DU-145 1

Data from ChEMBL 36 via Core Engine