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Compound Detail

CHEMBL150315

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COc1cc2ncnc(Nc3ccc(Cl)cc3F)c2cc1OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL150315
Phase Preclinical
Structure Type MOL
InChI Key YHUIUSRCUKUUQA-UHFFFAOYSA-N
6
Targets
17
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

333.8
MW (Da)
4.18
ALogP
5
HBA
1
HBD
56.3
PSA (Ų)
0.78
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C16H13ClFN3O2
MW 333.75
Aromatic Rings 3
Heavy Atoms 23
NP-Likeness -1.46

Activity Summary

IC50 15 meas. best 7.0
Kd 2 meas. best 5.21

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Vascular endothelial growth factor receptor 2
CHEMBL279
 IC50 7.0 6.41 100.0 2
Vascular endothelial growth factor receptor
CHEMBL2095227
 IC50 6.0 6.0 1000.0 1
Vascular endothelial growth factor receptor 1
CHEMBL1868
 IC50 5.7 5.0056 2000.0 9
Ephrin type-B receptor 2
CHEMBL3290
 Kd 5.21 5.21 6200.0 1
Unchecked
CHEMBL612545
 Kd 5.21 5.21 6200.0 1
Fibroblast growth factor receptor 1
CHEMBL3650
 IC50 5.16 5.16 7000.0 1
Ephrin type-B receptor 2
CHEMBL3290
 IC50 5.07 5.07 8500.0 1
Unchecked
CHEMBL612545
 IC50 5.07 5.07 8500.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Vascular endothelial growth factor receptor 2 IC50 = 100.0 nM 7.0 Vascular endothelial growth factor receptor 2 inhibitory activity at 2 uM of ATP... 10639280
Vascular endothelial growth factor receptor IC50 = 1000.0 nM 6.0 Inhibitory activity against VEGF-stimulated proliferation in HUVEC 16216503
Vascular endothelial growth factor receptor 2 IC50 = 1500.0 nM 5.82 Inhibitory activity against VEGFR2 kinase 16216503
Vascular endothelial growth factor receptor 1 IC50 = 2000.0 nM 5.7 In vitro vascular endothelial growth factor receptor 1 inhibitory activity at 2 ... 10639280
Vascular endothelial growth factor receptor 1 IC50 = 2000.0 nM 5.7 Inhibitory activity against flt kinase 16216503
Ephrin type-B receptor 2 Kd = 6200.0 nM 5.21 Equilibrium binding constant for EPH receptor B2 15857128
Unchecked Kd = 6200.0 nM 5.21 Binding constant for EphB2 tyrosine kinase 15456253
Fibroblast growth factor receptor 1 IC50 = 7000.0 nM 5.16 FGFR-1 (FTK) inhibitory activity at 2 uM of ATP in vitro. 10639280
Ephrin type-B receptor 2 IC50 = 8500.0 nM 5.07 Inhibition of EPH receptor B2 using ELISA 15857128
Unchecked IC50 = 8500.0 nM 5.07 Inhibition of EphB2 receptor tyrosine kinase in ELISA assay 15456253
Vascular endothelial growth factor receptor 1 IC50 = 14100.0 nM 4.85 Inhibition of VEGFR1 in human A498 cells by phosphotyrosine cell-based ELISA 20092323
Vascular endothelial growth factor receptor 1 IC50 = 14100.0 nM 4.85 Inhibition of VEGFR1 phosphorylation in human A498 cells after 10 mins by FLISA 20403700
Vascular endothelial growth factor receptor 1 IC50 = 14100.0 nM 4.85 Inhibition of VEGFR1 tyrosine kinase activity in VEGF-stimulated human A498 cell... 22204741
Vascular endothelial growth factor receptor 1 IC50 = 14100.0 nM 4.85 Inhibition of VEGF-induced VEGFR1 phosphorylation in human A498 cells overexpres... 23375090
Vascular endothelial growth factor receptor 1 IC50 = 17700.0 nM 4.75 Inhibition of VEGFR1 expressed in human tumor cells 18467105
Vascular endothelial growth factor receptor 1 IC50 = 17700.0 nM 4.75 Inhibition of VEGFR1 20403693
Vascular endothelial growth factor receptor 1 IC50 = 17700.0 nM 4.75 Inhibition of VEGF-induced VEGFR1 autophosphorylation in human A498 cells incuba... 22370340

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
15456253 10.1021/jm049733a Unchecked 2
15857128 10.1021/jm0492204 Ephrin type-B receptor 2 2
16216503 10.1016/j.bmcl.2005.09.036 Vascular endothelial growth factor receptor 1 1
38157838 10.1016/j.bmc.2023.117561 Unchecked 1
23375090 10.1016/j.bmc.2012.12.045 Vascular endothelial growth factor receptor 1 1
22370340 10.1016/j.bmc.2012.01.029 Vascular endothelial growth factor receptor 1 1
22204741 10.1016/j.bmc.2011.11.058 Vascular endothelial growth factor receptor 1 1
20403700 10.1016/j.bmc.2010.03.052 Vascular endothelial growth factor receptor 1 1
20403693 10.1016/j.bmcl.2010.03.064 Vascular endothelial growth factor receptor 1 1
20092323 10.1021/jm9011142 Vascular endothelial growth factor receptor 1 1
18467105 10.1016/j.bmc.2008.04.019 Vascular endothelial growth factor receptor 1 1
10639280 10.1021/jm990345w Vascular endothelial growth factor receptor 1 1
16216503 10.1016/j.bmcl.2005.09.036 Vascular endothelial growth factor receptor 1
16216503 10.1016/j.bmcl.2005.09.036 Vascular endothelial growth factor receptor 2 1
10639280 10.1021/jm990345w VEGF-receptor 2 and Fibroblast growth factor receptor 1 1
10639280 10.1021/jm990345w Unchecked 1
10639280 10.1021/jm990345w Rattus norvegicus 1
10639280 10.1021/jm990345w Fibroblast growth factor receptor 1 1

Data from ChEMBL 36 via Core Engine