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Compound Detail

CHEMBL4062877

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Cc1n[nH]c2ccc(-c3cc(N[C@@H](CO)c4ccccc4)cnc3-c3cc(F)ccc3O)cc12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4062877
Phase Preclinical
Structure Type MOL
InChI Key QXIOZIFTPMAING-VWLOTQADSA-N
22
Targets
36
Activities
1
Assay Types
26
PK Parameters
20
Publications
0
Known Names

Molecular Properties

454.5
MW (Da)
5.59
ALogP
5
HBA
4
HBD
94.1
PSA (Ų)
0.27
QED
1
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C27H23FN4O2
MW 454.51
Aromatic Rings 5
Heavy Atoms 34
NP-Likeness -0.90

Activity Summary

IC50 36 meas. best 9.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Proto-oncogene tyrosine-protein kinase receptor Ret
CHEMBL2041
 IC50 9.7 8.1 0.2 2
Epidermal growth factor receptor
CHEMBL203
 IC50 9.4 8.116 0.4 5
Discoidin domain-containing receptor 2
CHEMBL5122
 IC50 9.1 7.8 0.8 2
Vascular endothelial growth factor receptor 1
CHEMBL1868
 IC50 9.0 9.0 1.0 1
Fibroblast growth factor receptor 2
CHEMBL4142
 IC50 8.8 7.74 1.6 3
Vascular endothelial growth factor receptor 2
CHEMBL279
 IC50 8.77 8.39 1.7 2
Tyrosine-protein kinase ABL1
CHEMBL1862
 IC50 8.54 8.54 2.9 1
Proto-oncogene tyrosine-protein kinase Src
CHEMBL267
 IC50 8.24 8.24 5.7 1
Receptor tyrosine-protein kinase erbB-4
CHEMBL3009
 IC50 8.21 8.21 6.2 1
Fibroblast growth factor receptor 1
CHEMBL3650
 IC50 7.84 7.3333 14.5 3
KG-1
CHEMBL612264
 IC50 7.84 7.84 14.5 1
SNU-16
CHEMBL613529
 IC50 7.61 7.61 24.8 1
Fibroblast growth factor receptor 3
CHEMBL2742
 IC50 7.56 7.235 27.5 2
Tyrosine-protein kinase Mer
CHEMBL5331
 IC50 7.43 7.43 36.9 1
ALK tyrosine kinase receptor
CHEMBL4247
 IC50 7.0 7.0 101.1 1
Leukocyte tyrosine kinase receptor
CHEMBL5627
 IC50 6.91 6.91 122.9 1
RT-112
CHEMBL614145
 IC50 6.91 6.91 122.5 1
Unchecked
CHEMBL612545
 IC50 6.89 6.8633 128.1 3
Fibroblast growth factor receptor 4
CHEMBL3973
 IC50 6.52 6.52 299.4 1
NCI-H1581
CHEMBL1075516
 IC50 6.41 6.41 391.2 1
Insulin receptor
CHEMBL1981
 IC50 6.38 6.38 417.5 1
Mitogen-activated protein kinase 1
CHEMBL4040
 IC50 6.24 6.24 574.7 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 16629.1 ng.hr.mL-1 Rattus norvegicus
AUC 13748.4 ng.hr.mL-1 Rattus norvegicus
AUC 2402.0 ng.hr.mL-1 Mus musculus
AUC 289.0 ng.hr.mL-1 Mus musculus
AUC 18705.5 ng.hr.mL-1 Rattus norvegicus
AUC 13756.9 ng.hr.mL-1 Rattus norvegicus
AUC 2409.0 ng.hr.mL-1 Mus musculus
AUC 290.0 ng.hr.mL-1 Mus musculus
CL 12.12 mL.min-1.kg-1 Rattus norvegicus
Cmax 4569.76 nM Rattus norvegicus
Cmax 14378.12 nM Rattus norvegicus
Cmax 2114.36 nM Mus musculus
Cmax 233.22 nM Mus musculus
F 60.0 % Rattus norvegicus
MRT 6.72 hr Rattus norvegicus
MRT 3.41 hr Rattus norvegicus
MRT 3.59 hr Mus musculus
MRT 3.74 hr Mus musculus
T1/2 8.0 hr Rattus norvegicus
T1/2 2.39 hr Rattus norvegicus
T1/2 2.72 hr Mus musculus
T1/2 2.5 hr Mus musculus
Tmax 1.0 hr Rattus norvegicus
Tmax 0.25 hr Rattus norvegicus
Tmax 0.42 hr Mus musculus
Tmax 1.5 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Proto-oncogene tyrosine-protein kinase receptor Ret IC50 = 0.2 nM 9.7 Inhibition of recombinant Ret (unknown origin) using poly (Glu,Tyr) 4:1 as subst... 28714692
Epidermal growth factor receptor IC50 = 0.4 nM 9.4 Inhibition of EGFR exon 19 deletion mutant in human HCC827 cells assessed as inh... 28714692
Discoidin domain-containing receptor 2 IC50 = 0.8 nM 9.1 Inhibition of recombinant DDR2 (unknown origin) using poly (Glu,Tyr) 4:1 as subs... 28714692
Vascular endothelial growth factor receptor 1 IC50 = 1.0 nM 9.0 Inhibition of recombinant VEGFR-1 (unknown origin) using poly (Glu,Tyr) 4:1 as s... 28714692
Fibroblast growth factor receptor 2 IC50 = 1.6 nM 8.8 Inhibition of recombinant human FGFR2 using poly (Glu,Tyr) 4:1 as substrate afte... 28714692
Vascular endothelial growth factor receptor 2 IC50 = 1.7 nM 8.77 Inhibition of recombinant KDR (unknown origin) using poly (Glu,Tyr) 4:1 as subst... 28714692
Tyrosine-protein kinase ABL1 IC50 = 2.9 nM 8.54 Inhibition of recombinant ABL (unknown origin) using poly (Glu,Tyr) 4:1 as subst... 28714692
Epidermal growth factor receptor IC50 = 4.7 nM 8.33 Inhibition of recombinant EGFR (unknown origin) using poly (Glu,Tyr) 4:1 as subs... 28714692
Epidermal growth factor receptor IC50 = 5.3 nM 8.28 Inhibition of EGFR L858R mutant in human PC9 cells assessed as inhibition of cel... 28714692
Proto-oncogene tyrosine-protein kinase Src IC50 = 5.7 nM 8.24 Inhibition of recombinant c-Src (unknown origin) using poly (Glu,Tyr) 4:1 as sub... 28714692
Epidermal growth factor receptor IC50 = 6.0 nM 8.22 Inhibition of recombinant EGFR T790M/L858R mutant (unknown origin) using poly (G... 28714692
Receptor tyrosine-protein kinase erbB-4 IC50 = 6.2 nM 8.21 Inhibition of recombinant ErbB4 (unknown origin) using poly (Glu,Tyr) 4:1 as sub... 28714692
Vascular endothelial growth factor receptor 2 IC50 = 9.8 nM 8.01 Inhibition of TEL-fused KDR (unknown origin) expressed in mouse Ba/F3 cells asse... 28714692
Fibroblast growth factor receptor 1 IC50 = 14.5 nM 7.84 Inhibition of FGFR1OP2 fused FGFR1 in human KG1 cells assessed as inhibition of ... 28714692
KG-1 IC50 = 14.5 nM 7.84 Antiproliferative activity against human KG-1 cells assessed as inhibition of ce... 31761386
Fibroblast growth factor receptor 1 IC50 = 18.0 nM 7.75 Inhibition of recombinant human FGFR1 using poly (Glu,Tyr) 4:1 as substrate afte... 28714692
Fibroblast growth factor receptor 2 IC50 = 24.8 nM 7.61 Inhibition of FGFR2 in human SNU16 cells assessed as inhibition of cell prolifer... 28714692
SNU-16 IC50 = 24.8 nM 7.61 Antiproliferative activity against human SNU-16 cells assessed as inhibition of ... 31761386
Fibroblast growth factor receptor 3 IC50 = 27.5 nM 7.56 Inhibition of recombinant human FGFR3 using poly (Glu,Tyr) 4:1 as substrate afte... 28714692
Tyrosine-protein kinase Mer IC50 = 36.9 nM 7.43 Inhibition of recombinant Mer (unknown origin) using poly (Glu,Tyr) 4:1 as subst... 28714692

Literature References

PubMed DOI Target Context # Activities
28714692 10.1021/acs.jmedchem.7b00076 Mus musculus 17
28714692 10.1021/acs.jmedchem.7b00076 Rattus norvegicus 14
28714692 10.1021/acs.jmedchem.7b00076 Fibroblast growth factor receptor 1 11
28714692 10.1021/acs.jmedchem.7b00076 Fibroblast growth factor receptor 2 7
28714692 10.1021/acs.jmedchem.7b00076 Vascular endothelial growth factor receptor 2 6
28714692 10.1021/acs.jmedchem.7b00076 Proto-oncogene tyrosine-protein kinase receptor Ret 6
28714692 10.1021/acs.jmedchem.7b00076 Epidermal growth factor receptor 5
28714692 10.1021/acs.jmedchem.7b00076 Discoidin domain-containing receptor 2 5
28714692 10.1021/acs.jmedchem.7b00076 Unchecked 5
28714692 10.1021/acs.jmedchem.7b00076 NCI-H1581 3
31761386 10.1016/j.ejmech.2019.111884 Unchecked 2
28714692 10.1021/acs.jmedchem.7b00076 Fibroblast growth factor receptor 3 2
28714692 10.1021/acs.jmedchem.7b00076 Tyrosine-protein kinase ABL1 1
28714692 10.1021/acs.jmedchem.7b00076 Proto-oncogene tyrosine-protein kinase Src 1
28714692 10.1021/acs.jmedchem.7b00076 Vascular endothelial growth factor receptor 1 1
28714692 10.1021/acs.jmedchem.7b00076 Insulin receptor 1
28714692 10.1021/acs.jmedchem.7b00076 Insulin-like growth factor 1 receptor 1
31761386 10.1016/j.ejmech.2019.111884 RT-112 1
28714692 10.1021/acs.jmedchem.7b00076 Receptor tyrosine-protein kinase erbB-2 1
28714692 10.1021/acs.jmedchem.7b00076 ALK tyrosine kinase receptor 1

Data from ChEMBL 36 via Core Engine