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Compound Detail

CHEMBL4783398

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Cc1ccc(-n2cc(COc3cccc4cnc(Nc5cccc(Cl)c5)nc34)nn2)c([N+](=O)[O-])c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4783398
Phase Preclinical
Structure Type MOL
InChI Key JEPGNFQKCRZPHJ-UHFFFAOYSA-N
11
Targets
15
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

487.9
MW (Da)
5.40
ALogP
9
HBA
1
HBD
120.9
PSA (Ų)
0.24
QED
1
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C24H18ClN7O3
MW 487.91
Aromatic Rings 5
Heavy Atoms 35
NP-Likeness -2.04

Activity Summary

IC50 14 meas. best 7.96
Kd 1 meas. best 6.95

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Dual specificity protein kinase CLK1
CHEMBL4224
 IC50 7.96 6.685 11.0 2
Dual specificity protein kinase CLK4
CHEMBL4203
 IC50 7.7 6.62 20.0 2
Dual specificity protein kinase CLK2
CHEMBL4225
 IC50 7.57 6.69 27.0 2
Dual specificity protein kinase CLK1
CHEMBL4224
 Kd 6.95 6.95 112.2 1
Dual specificity tyrosine-phosphorylation-regulated kinase 1A
CHEMBL5508
 IC50 6.92 6.92 120.0 1
Dual specificity protein kinase CLK3
CHEMBL4226
 IC50 5.89 5.89 1280.0 1
MCF7
CHEMBL387
 IC50 5.4 5.4 4000.0 1
PC-3
CHEMBL390
 IC50 5.16 5.16 7000.0 1
Fibroblast
CHEMBL5314315
 IC50 4.68 4.68 21000.0 1
Huh-7
CHEMBL614039
 IC50 4.6 4.6 25000.0 1
Caco-2
CHEMBL614058
 IC50 4.43 4.43 37000.0 1
HT-22
CHEMBL614316
 IC50 4.0 4.0 100000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Dual specificity protein kinase CLK1 IC50 = 11.0 nM 7.96 Inhibition of recombinant human CLK1 (130 to end residues) using ERMRPRKRQGSVRRR... 33422908
Dual specificity protein kinase CLK4 IC50 = 20.0 nM 7.7 Inhibition of recombinant human CLK4 (128 to end residues) using YRRAAVPPSPSLSRH... 33422908
Dual specificity protein kinase CLK2 IC50 = 27.0 nM 7.57 Inhibition of recombinant human CLK2 (138 to end residues) using YRRAAVPPSPSLSRH... 33422908
Dual specificity protein kinase CLK1 Kd = 112.24 nM 6.95 Binding affinity to human CLK1 assessed as equilibrium dissociation constant mea... 36876904
Dual specificity tyrosine-phosphorylation-regulated kinase 1A IC50 = 120.0 nM 6.92 Inhibition of rat DYRK1A (1 to 499 residues) assessed as residual activity by AD... 33422908
Dual specificity protein kinase CLK3 IC50 = 1280.0 nM 5.89 Inhibition of recombinant human full length CLK3 using ERMRPRKRQGSVRRRV as subst... 33422908
Dual specificity protein kinase CLK2 IC50 = 1542.0 nM 5.81 Inhibition of recombinant human CLK2 expressed in Sf9 insect cells incubated for... 36876904
Dual specificity protein kinase CLK4 IC50 = 2919.0 nM 5.54 Inhibition of recombinant human CLK4 expressed in Sf9 insect cells incubated for... 36876904
Dual specificity protein kinase CLK1 IC50 = 3879.0 nM 5.41 Inhibition of recombinant human CLK1 expressed in Sf9 insect cells incubated for... 36876904
MCF7 IC50 = 4000.0 nM 5.4 Cytotoxicity against human MCF7 cells assessed as reduction in cell viability in... 33422908
PC-3 IC50 = 7000.0 nM 5.16 Cytotoxicity against human PC-3 cells assessed as reduction in cell viability in... 33422908
Fibroblast IC50 = 21000.0 nM 4.68 Cytotoxicity against human Fibroblast cells assessed as reduction in cell viabil... 33422908
Huh-7 IC50 = 25000.0 nM 4.6 Cytotoxicity against human HuH-7 cells assessed as reduction in cell viability i... 33422908
Caco-2 IC50 = 37000.0 nM 4.43 Cytotoxicity against human CaCo-2 cells assessed as reduction in cell viability ... 33422908
HT-22 IC50 = 100000.0 nM 4.0 Cytotoxicity against mouse HT-22 cells assessed as reduction in cell viability i... 36876904

Literature References

PubMed DOI Target Context # Activities
33422908 10.1016/j.bmc.2020.115962 Dual specificity tyrosine-phosphorylation-regulated kinase 1A 4
36876904 10.1021/acs.jmedchem.2c02068 Dual specificity protein kinase CLK1 3
36876904 10.1021/acs.jmedchem.2c02068 Dual specificity tyrosine-phosphorylation-regulated kinase 1A 3
36876904 10.1021/acs.jmedchem.2c02068 Glycogen synthase kinase-3 beta 3
33422908 10.1016/j.bmc.2020.115962 Dual specificity protein kinase CLK1 2
33422908 10.1016/j.bmc.2020.115962 Dual specificity protein kinase CLK4 1
33422908 10.1016/j.bmc.2020.115962 Fibroblast 1
33422908 10.1016/j.bmc.2020.115962 MCF7 1
33422908 10.1016/j.bmc.2020.115962 PC-3 1
33422908 10.1016/j.bmc.2020.115962 HCT-116 1
33422908 10.1016/j.bmc.2020.115962 MDA-MB-231 1
33422908 10.1016/j.bmc.2020.115962 Caco-2 1
33422908 10.1016/j.bmc.2020.115962 Huh-7 1
33422908 10.1016/j.bmc.2020.115962 Cyclin-dependent kinase 5/CDK5 activator 1 1
36876904 10.1021/acs.jmedchem.2c02068 HT-22 1
33422908 10.1016/j.bmc.2020.115962 Dual specificity protein kinase CLK2 1
33422908 10.1016/j.bmc.2020.115962 Casein kinase I isoform epsilon 1
33422908 10.1016/j.bmc.2020.115962 Glycogen synthase kinase-3 beta 1
33422908 10.1016/j.bmc.2020.115962 Serine/threonine-protein kinase haspin 1
33422908 10.1016/j.bmc.2020.115962 Serine/threonine-protein kinase pim-1 1

Data from ChEMBL 36 via Core Engine