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Compound Detail

CHEMBL177688

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OCCCNc1cncc(-c2cncc(Nc3cccc(Cl)c3)n2)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL177688
Phase Preclinical
Structure Type MOL
InChI Key UCHQCSDTPQKAKL-UHFFFAOYSA-N
12
Targets
22
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

355.8
MW (Da)
3.73
ALogP
6
HBA
3
HBD
83.0
PSA (Ų)
0.56
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C18H18ClN5O
MW 355.83
Aromatic Rings 3
Heavy Atoms 25
NP-Likeness -1.48

Activity Summary

IC50 22 meas. best 8.3

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Vascular endothelial growth factor receptor
CHEMBL2095227
 IC50 8.3 8.3 5.0 1
Vascular endothelial growth factor receptor 2
CHEMBL279
 IC50 7.08 7.08 83.2 3
HUVEC
CHEMBL613979
 IC50 6.79 6.1167 164.0 3
Fibroblast growth factor receptor 2
CHEMBL4142
 IC50 6.68 6.68 210.0 2
Platelet-derived growth factor receptor
CHEMBL2095189
 IC50 6.44 6.44 360.0 1
Unchecked
CHEMBL612545
 IC50 6.44 6.44 360.0 1
Glycogen synthase kinase-3
CHEMBL2095188
 IC50 6.32 6.32 478.0 2
Epidermal growth factor receptor
CHEMBL203
 IC50 5.87 5.87 1360.0 2
Insulin receptor
CHEMBL1981
 IC50 5.77 5.77 1690.0 2
HASMC
CHEMBL614150
 IC50 5.41 5.41 3870.0 2
MRC5
CHEMBL614181
 IC50 5.18 5.18 6600.0 2
HeLa
CHEMBL399
 IC50 5.0 5.0 10000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Vascular endothelial growth factor receptor IC50 = 5.0 nM 8.3 Inhibition of VEGF-stimulated human umbilical vein endothelial cell proliferatio... 15771433
Vascular endothelial growth factor receptor 2 IC50 = 84.0 nM 7.08 Inhibition of human vascular endothelial growth factor receptor 2 15771433
Vascular endothelial growth factor receptor 2 IC50 = 84.0 nM 7.08 Inhibition of vascular endothelial growth factor receptor 2 16033269
Vascular endothelial growth factor receptor 2 IC50 = 83.18 nM 7.08 Inhibitory concentration (experimental) against vascular endothelial growth fact... 16033269
HUVEC IC50 = 164.0 nM 6.79 Concentration inhibiting VEGF stimulated (2 ng/well) HUVE cell proliferation 16033269
Fibroblast growth factor receptor 2 IC50 = 210.0 nM 6.68 Inhibition of fibroblast growth factor receptor 2 15771433
Fibroblast growth factor receptor 2 IC50 = 210.0 nM 6.68 Inhibitory concentration against Fibroblast growth factor receptor 2 16033269
Platelet-derived growth factor receptor IC50 = 360.0 nM 6.44 Inhibition of platelet-derived growth factor receptor 15771433
Unchecked IC50 = 360.0 nM 6.44 Inhibition of platelet-derived growth factor receptor 16033269
Glycogen synthase kinase-3 IC50 = 478.0 nM 6.32 Inhibition of glycogen synthase kinase-3 15771433
Glycogen synthase kinase-3 IC50 = 478.0 nM 6.32 Inhibition of glycogen synthase kinase-3 16033269
Epidermal growth factor receptor IC50 = 1360.0 nM 5.87 Inhibition of epidermal growth factor receptor 15771433
Epidermal growth factor receptor IC50 = 1360.0 nM 5.87 Inhibition of epidermal growth factor receptor 16033269
HUVEC IC50 = 1680.0 nM 5.78 Inhibitory concentration against Proliferation of human umbilical vein endotheli... 15771433
HUVEC IC50 = 1680.0 nM 5.78 Concentration required to inhibit proliferation of HUVEC 16033269
Insulin receptor IC50 = 1690.0 nM 5.77 Inhibition of insulin-Receptor kinase 15771433
Insulin receptor IC50 = 1690.0 nM 5.77 Inhibition of insulin Receptor kinase 16033269
HASMC IC50 = 3870.0 nM 5.41 Inhibitory concentration against Proliferation of human aortic smooth muscle cel... 15771433
HASMC IC50 = 3870.0 nM 5.41 Concentration required to inhibit proliferation of HASMC 16033269
MRC5 IC50 = 6600.0 nM 5.18 Inhibitory concentration against Proliferation of MRC5 lung fibroblasts 15771433

Literature References

PubMed DOI Target Context # Activities
16033269 10.1021/jm058205b Unchecked 4
16033269 10.1021/jm058205b Vascular endothelial growth factor receptor 2 3
16033269 10.1021/jm058205b HUVEC 2
15771433 10.1021/jm040099a MRC5 1
15771433 10.1021/jm040099a Cyclin-dependent kinase 4 1
15771433 10.1021/jm040099a Casein kinase II 1
15771433 10.1021/jm040099a CaM kinase II 1
15771433 10.1021/jm040099a A-375 1
15771433 10.1021/jm040099a HCT-116 1
15771433 10.1021/jm040099a HeLa 1
15771433 10.1021/jm040099a Cyclin-dependent kinase 1 1
15771433 10.1021/jm040099a Vascular endothelial growth factor receptor 2 1
16033269 10.1021/jm058205b Glycogen synthase kinase-3 1
15771433 10.1021/jm040099a HUVEC 1
15771433 10.1021/jm040099a Vascular endothelial growth factor receptor 1
15771433 10.1021/jm040099a Protein kinase C gamma type 1
15771433 10.1021/jm040099a Protein kinase C beta type 1
15771433 10.1021/jm040099a cAMP-dependent protein kinase (PKA) 1
15771433 10.1021/jm040099a Platelet-derived growth factor receptor 1
15771433 10.1021/jm040099a Mitogen-activated protein kinase 1 1

Data from ChEMBL 36 via Core Engine