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Compound Detail

CHEMBL369303

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O=Nc1c(-c2c(O)[nH]c3ccc([N+](=O)[O-])cc23)[nH]c2ccccc12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL369303
Phase Preclinical
Structure Type MOL
InChI Key GIMRHZPQMMMJKH-UHFFFAOYSA-N
13
Targets
16
Activities
1
Assay Types
0
PK Parameters
19
Publications
0
Known Names

Molecular Properties

322.3
MW (Da)
4.33
ALogP
5
HBA
3
HBD
124.4
PSA (Ų)
0.29
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C16H10N4O4
MW 322.28
Aromatic Rings 4
Heavy Atoms 24
NP-Likeness -0.30

Activity Summary

IC50 16 meas. best 8.68

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Glycogen synthase kinase-3
CHEMBL2366565
 IC50 8.68 8.68 2.1 1
Cyclin-dependent kinase 5/CDK5 activator 1
CHEMBL1907600
 IC50 8.22 8.22 6.0 1
Cyclin-dependent kinase 2/cyclin E1
CHEMBL1907605
 IC50 8.13 8.13 7.3 1
Unchecked
CHEMBL612545
 IC50 7.72 6.155 19.0 2
Receptor-type tyrosine-protein kinase FLT3
CHEMBL1974
 IC50 7.21 7.21 62.0 1
MV4-11
CHEMBL613835
 IC50 6.35 6.35 450.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 6.25 5.52 560.0 3
SNU-638
CHEMBL614935
 IC50 5.92 5.92 1200.0 1
Dual specificity tyrosine-phosphorylation-regulated kinase 1A
CHEMBL5508
 IC50 5.89 5.89 1300.0 1
MCF7
CHEMBL387
 IC50 5.85 5.85 1400.0 1
A549
CHEMBL392
 IC50 5.27 5.27 5400.0 1
HT-1080
CHEMBL614580
 IC50 5.23 5.23 5900.0 1
HL-60
CHEMBL383
 IC50 5.04 5.04 9200.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Glycogen synthase kinase-3 IC50 = 2.1 nM 8.68 Inhibition of porcine brain GSK3alpha/beta assessed as [gamma-33P]ATP incorporat... 19665384
Cyclin-dependent kinase 5/CDK5 activator 1 IC50 = 6.0 nM 8.22 Inhibition of GST-fused CDK5/p25 expressed in Escherichia coli assessed as [gamm... 19665384
Cyclin-dependent kinase 2/cyclin E1 IC50 = 7.35 nM 8.13 Inhibition of CDK2/cyclin E 20361800
Unchecked IC50 = 19.0 nM 7.72 Inhibition of Marthasterias glacialis CDK1/cyclin-B assessed as [gamma-33P]ATP i... 19665384
Receptor-type tyrosine-protein kinase FLT3 IC50 = 62.0 nM 7.21 Inhibition of FLT3 by HTRF assay 20153646
MV4-11 IC50 = 450.0 nM 6.35 Antiproliferative activity against wild type FLT3 expressing human MV411 cells a... 20153646
NON-PROTEIN TARGET IC50 = 560.0 nM 6.25 Antiproliferative activity against human RS4:11 cells having FLT3-ITD mutation a... 20153646
SNU-638 IC50 = 1200.0 nM 5.92 Antiproliferative activity against human SNU638 cells 23290050
Dual specificity tyrosine-phosphorylation-regulated kinase 1A IC50 = 1300.0 nM 5.89 Inhibition of GST-fused rat recombinant DYRK1A expressed in Escherichia coli ass... 19665384
MCF7 IC50 = 1400.0 nM 5.85 Antiproliferative activity against human MCF7 cells 23290050
A549 IC50 = 5400.0 nM 5.27 Inhibitory activity on the proliferation of Human lung carcinoma A549 cancer cel... 15993584
NON-PROTEIN TARGET IC50 = 5400.0 nM 5.27 Antiproliferative activity against human lung cancer cells 23290050
HT-1080 IC50 = 5900.0 nM 5.23 Inhibitory activity on the proliferation of Human fibrosarcoma HT1080 cancer cel... 15993584
HL-60 IC50 = 9200.0 nM 5.04 Inhibitory activity on the proliferation of Human myeloid leukemia HL-60 cancer ... 15993584
NON-PROTEIN TARGET IC50 = 9200.0 nM 5.04 Antiproliferative activity against human leukemia cells 23290050
Unchecked IC50 = 25500.0 nM 4.59 Inhibitory activity on the proliferation of Human colon carcinoma Co12 cancer ce... 15993584

Literature References

PubMed DOI Target Context # Activities
15993584 10.1016/j.bmcl.2005.05.105 A549 13
19282173 10.1016/j.bmcl.2009.02.083 Molecular identity unknown 4
20361800 10.1021/jm100080z No relevant target 4
23290050 10.1016/j.bmcl.2012.12.006 NON-PROTEIN TARGET 2
18824607 10.1128/aac.00903-08 ADMET 2
19665384 10.1016/j.bmc.2009.07.051 Unchecked 2
20153646 10.1016/j.bmcl.2010.01.039 Receptor-type tyrosine-protein kinase FLT3 1
23290050 10.1016/j.bmcl.2012.12.006 SNU-638 1
23290050 10.1016/j.bmcl.2012.12.006 MCF7 1
18824607 10.1128/aac.00903-08 Toxoplasma gondii 1
20361800 10.1021/jm100080z Cyclin-dependent kinase 2/cyclin E1 1
20153646 10.1016/j.bmcl.2010.01.039 MV4-11 1
20153646 10.1016/j.bmcl.2010.01.039 NON-PROTEIN TARGET 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 Cyclin-dependent kinase 5/CDK5 activator 1 1
19665384 10.1016/j.bmc.2009.07.051 Glycogen synthase kinase-3 1
15993584 10.1016/j.bmcl.2005.05.105 HL-60 1
15993584 10.1016/j.bmcl.2005.05.105 HT-1080 1
15993584 10.1016/j.bmcl.2005.05.105 Unchecked 1

Data from ChEMBL 36 via Core Engine