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Compound Detail

CHEMBL272198

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COc1cc2nccc(Oc3ccc4c(C(=O)NC5CC5)cccc4c3)c2cc1OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL272198
Phase Preclinical
Structure Type MOL
InChI Key ZATGFXTWDKIEKC-UHFFFAOYSA-N
10
Targets
16
Activities
1
Assay Types
8
PK Parameters
20
Publications
0
Known Names

Molecular Properties

414.5
MW (Da)
5.09
ALogP
5
HBA
1
HBD
69.7
PSA (Ų)
0.48
QED
1
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C25H22N2O4
MW 414.46
Aromatic Rings 4
Heavy Atoms 31
NP-Likeness -0.70

Activity Summary

IC50 16 meas. best 9.22

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Vascular endothelial growth factor receptor 2
CHEMBL279
 IC50 9.22 9.22 0.6 4
HUVEC
CHEMBL613979
 IC50 9.04 7.8975 0.9 4
Tyrosine-protein kinase Lyn
CHEMBL3905
 IC50 7.57 7.57 27.0 1
Aurora kinase B
CHEMBL2185
 IC50 6.93 6.93 118.0 1
Tyrosine-protein kinase Lck
CHEMBL258
 IC50 6.48 6.48 330.0 1
Tyrosine-protein kinase Fgr
CHEMBL4454
 IC50 6.4 6.4 396.0 1
Tyrosine-protein kinase ABL1
CHEMBL1862
 IC50 6.33 6.33 466.0 1
Aurora kinase A
CHEMBL4722
 IC50 5.7 5.7 2000.0 1
Hepatocyte growth factor receptor
CHEMBL3717
 IC50 4.7 4.7 20000.0 1
Angiopoietin-1 receptor
CHEMBL4128
 IC50 4.6 4.6 25000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 50228.0 ng.hr.mL-1 Rattus norvegicus
AUC 132.63 ng.hr.mL-1 Rattus norvegicus
CL 2.183 mL.min-1.kg-1 Rattus norvegicus
Cmax 14843.41 nM Rattus norvegicus
Cmax 20.0 nM Rattus norvegicus
F 66.0 % Rattus norvegicus
T1/2 8.4 hr Rattus norvegicus
Tmax 2.5 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Vascular endothelial growth factor receptor 2 IC50 = 0.6 nM 9.22 Inhibition of KDR 18324759
Vascular endothelial growth factor receptor 2 IC50 = 0.6 nM 9.22 Inhibition of KDR by HTRF assay 18324761
Vascular endothelial growth factor receptor 2 IC50 = 0.6 nM 9.22 Inhibition of KDR 20000735
Vascular endothelial growth factor receptor 2 IC50 = 0.6026 nM 9.22 Inhibition of human VEGFR2 after 60 mins 19081278
HUVEC IC50 = 0.91 nM 9.04 Inhibition of VEGF-induced proliferation of HUVEC 18324759
HUVEC IC50 = 1.0 nM 9.0 Inhibition of VEGF-induced proliferation of HUVEC cells 18324761
Tyrosine-protein kinase Lyn IC50 = 27.0 nM 7.57 Inhibition of Lyn 18324759
Aurora kinase B IC50 = 118.0 nM 6.93 Inhibition of Aurora B 18324759
HUVEC IC50 = 167.0 nM 6.78 Inhibition of bFGF-induced proliferation of HUVEC cells 18324761
HUVEC IC50 = 170.0 nM 6.77 Inhibition of bFGF-induced proliferation of HUVEC 18324759
Tyrosine-protein kinase Lck IC50 = 330.0 nM 6.48 Inhibition of Lck 18324759
Tyrosine-protein kinase Fgr IC50 = 396.0 nM 6.4 Inhibition of FGR 18324759
Tyrosine-protein kinase ABL1 IC50 = 466.0 nM 6.33 Inhibition of Abl 18324759
Aurora kinase A IC50 = 2000.0 nM 5.7 Inhibition of Aurora A 18324759
Hepatocyte growth factor receptor IC50 = 20000.0 nM 4.7 Inhibition of c-Met 18324759
Angiopoietin-1 receptor IC50 = 25000.0 nM 4.6 Inhibition of Tie2 18324759

Literature References

PubMed DOI Target Context # Activities
18324759 10.1021/jm701098w Rattus norvegicus 10
18324759 10.1021/jm701098w Liver microsomes 8
18324759 10.1021/jm701098w HUVEC 3
18324761 10.1021/jm701097z HUVEC 2
18324759 10.1021/jm701098w Unchecked 2
18324759 10.1021/jm701098w No relevant target 1
19081278 10.1016/j.jmgm.2008.10.006 Vascular endothelial growth factor receptor 2 1
18324759 10.1021/jm701098w Tyrosine-protein kinase ABL1 1
18324759 10.1021/jm701098w Receptor-type tyrosine-protein kinase FLT3 1
18324759 10.1021/jm701098w Platelet-derived growth factor receptor alpha 1
18324759 10.1021/jm701098w Macrophage colony-stimulating factor 1 receptor 1
18324759 10.1021/jm701098w Mast/stem cell growth factor receptor Kit 1
18324759 10.1021/jm701098w Vascular endothelial growth factor receptor 3 1
18324759 10.1021/jm701098w Vascular endothelial growth factor receptor 1 1
18324759 10.1021/jm701098w Mus musculus 1
18324759 10.1021/jm701098w Vascular endothelial growth factor receptor 2 1
18324759 10.1021/jm701098w Aurora kinase B 1
18324759 10.1021/jm701098w Aurora kinase A 1
18324759 10.1021/jm701098w Tyrosine-protein kinase Lck 1
18324759 10.1021/jm701098w Hepatocyte growth factor receptor 1

Data from ChEMBL 36 via Core Engine