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Compound Detail

CHEMBL4473365

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C=CC(=O)Nc1cc(Nc2ncc(Cl)c(Nc3ccccc3S(=O)(=O)C(C)C)n2)c(OC)cc1N(C)CCN(C)C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4473365
Phase Preclinical
Structure Type MOL
InChI Key GDRLJBDXWDATLA-UHFFFAOYSA-N
15
Targets
23
Activities
2
Assay Types
9
PK Parameters
20
Publications
0
Known Names

Molecular Properties

602.2
MW (Da)
4.93
ALogP
10
HBA
3
HBD
128.8
PSA (Ų)
0.23
QED
1
Ro5 Violations
13
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C28H36ClN7O4S
MW 602.16
Aromatic Rings 3
Heavy Atoms 41
NP-Likeness -1.40

Activity Summary

IC50 15 meas. best 8.7
EC50 8 meas. best 8.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Epidermal growth factor receptor
CHEMBL203
 IC50 8.7 7.9733 2.0 3
Tyrosine-protein kinase Fer
CHEMBL3982
 IC50 8.7 8.7 2.0 1
Tyrosine-protein kinase BTK
CHEMBL5251
 IC50 8.7 8.7 2.0 1
Proto-oncogene tyrosine-protein kinase ROS
CHEMBL5568
 IC50 8.7 8.7 2.0 1
Receptor tyrosine-protein kinase erbB-4
CHEMBL3009
 IC50 8.52 8.52 3.0 1
Epidermal growth factor receptor
CHEMBL203
 EC50 8.4 8.128 4.0 5
Leukocyte tyrosine kinase receptor
CHEMBL5627
 IC50 8.4 8.4 4.0 1
EML4-ALK
CHEMBL3883330
 EC50 8.15 8.15 7.0 1
Insulin receptor
CHEMBL1981
 IC50 8.1 8.1 8.0 1
Tyrosine-protein kinase Blk
CHEMBL2250
 IC50 8.1 8.1 8.0 1
Activated CDC42 kinase 1
CHEMBL4599
 IC50 7.89 7.89 13.0 1
Focal adhesion kinase 1
CHEMBL2695
 IC50 7.75 7.75 18.0 1
ALK tyrosine kinase receptor
CHEMBL4247
 IC50 7.75 7.75 18.0 1
Receptor tyrosine-protein kinase erbB-2
CHEMBL1824
 IC50 7.43 7.43 37.0 1
STE20-like serine/threonine-protein kinase
CHEMBL4202
 IC50 7.24 7.24 58.0 1
Unchecked
CHEMBL612545
 EC50 6.77 6.43 170.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 1287.0 ng.hr.mL-1 Mus musculus
AUC 1551.0 ng.hr.mL-1 Mus musculus
CL 28.99 mL.min-1.kg-1 Mus musculus
CL 114.54 mL.min-1.kg-1 Mus musculus
Cmax 1464.73 nM Mus musculus
Cmax 863.56 nM Mus musculus
F 24.0 % Mus musculus
T1/2 1.25 hr Mus musculus
Tmax 1.17 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Proto-oncogene tyrosine-protein kinase ROS IC50 = 2.0 nM 8.7 Inhibition of recombinant GST-tagged human ROS1 cytoplasmic domain expressed in ... 28528303
Tyrosine-protein kinase Fer IC50 = 2.0 nM 8.7 Inhibition of recombinant GST/His-tagged human FER catalytic domain expressed in... 28528303
Tyrosine-protein kinase BTK IC50 = 2.0 nM 8.7 Inhibition of recombinant full length His-tagged human BTK cytoplasmic domain ex... 28528303
Epidermal growth factor receptor IC50 = 2.0 nM 8.7 Inhibition of GST-tagged human EGFR T790M mutant cytoplasmic domain (668 to 1210... 28528303
Receptor tyrosine-protein kinase erbB-4 IC50 = 3.0 nM 8.52 Inhibition of recombinant N-terminal GST-tagged human ErbB4 cytoplasmic domain e... 28528303
Epidermal growth factor receptor EC50 = 4.0 nM 8.4 Inhibition of EGFR L858R mutant (unknown origin) transfected in mouse BAF3 cells... 28528303
Leukocyte tyrosine kinase receptor IC50 = 4.0 nM 8.4 Inhibition of recombinant GST-tagged human LTK cytoplasmic domain (440 to 864 re... 28528303
Epidermal growth factor receptor IC50 = 4.0 nM 8.4 Inhibition of GST-tagged human EGFR T790M/L858R double mutant cytoplasmic domain... 28528303
Epidermal growth factor receptor EC50 = 5.0 nM 8.3 Inhibition of EGFR T790M exon19 deletion double mutant (unknown origin) transfec... 28528303
Epidermal growth factor receptor EC50 = 6.0 nM 8.22 Inhibition of EGFR T790M/L858R double mutant (unknown origin) transfected in mou... 28528303
Epidermal growth factor receptor EC50 = 6.0 nM 8.22 Inhibition of EGFR exon19 deletion mutant (unknown origin) transfected in mouse ... 28528303
EML4-ALK EC50 = 7.0 nM 8.15 Inhibition of EML4/ALK (unknown origin) transfected in mouse BAF3 cells assessed... 28528303
Tyrosine-protein kinase Blk IC50 = 8.0 nM 8.1 Inhibition of recombinant full length His-tagged human Blk cytoplasmic domain ex... 28528303
Insulin receptor IC50 = 8.0 nM 8.1 Inhibition of recombinant His-tagged human InsR (1011 to 1382 residues) expresse... 28528303
Activated CDC42 kinase 1 IC50 = 13.0 nM 7.89 Inhibition of recombinant GST-tagged human TNK2 catalytic/cytoplasmic domain (11... 28528303
ALK tyrosine kinase receptor IC50 = 18.0 nM 7.75 Inhibition of GST-tagged human ALK cytoplasmic domain (1058 to 1620 residues) ex... 28528303
Focal adhesion kinase 1 IC50 = 18.0 nM 7.75 Inhibition of recombinant full length GST-tagged human FAK expressed in baculovi... 28528303
Epidermal growth factor receptor EC50 = 32.0 nM 7.5 Inhibition of wild type EGFR (unknown origin) transfected in mouse BAF3 cells as... 28528303
Receptor tyrosine-protein kinase erbB-2 IC50 = 37.0 nM 7.43 Inhibition of recombinant His-tagged human ErbB2 cytoplasmic domain expressed in... 28528303
STE20-like serine/threonine-protein kinase IC50 = 58.0 nM 7.24 Inhibition of recombinant full length GST-tagged human SLK expressed in baculovi... 28528303

Literature References

PubMed DOI Target Context # Activities
28528303 10.1016/j.ejmech.2017.04.079 Epidermal growth factor receptor 23
28528303 10.1016/j.ejmech.2017.04.079 ADMET 22
28528303 10.1016/j.ejmech.2017.04.079 Tyrosine-protein kinase ABL1 15
28528303 10.1016/j.ejmech.2017.04.079 Receptor-type tyrosine-protein kinase FLT3 11
28528303 10.1016/j.ejmech.2017.04.079 Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform 10
28528303 10.1016/j.ejmech.2017.04.079 Mast/stem cell growth factor receptor Kit 9
28528303 10.1016/j.ejmech.2017.04.079 Unchecked 8
28528303 10.1016/j.ejmech.2017.04.079 ALK tyrosine kinase receptor 4
28528303 10.1016/j.ejmech.2017.04.079 Proto-oncogene tyrosine-protein kinase receptor Ret 4
28528303 10.1016/j.ejmech.2017.04.079 EML4-ALK 4
28528303 10.1016/j.ejmech.2017.04.079 Hepatocyte growth factor receptor 3
28528303 10.1016/j.ejmech.2017.04.079 Macrophage colony-stimulating factor 1 receptor 2
28528303 10.1016/j.ejmech.2017.04.079 Tyrosine-protein kinase JAK1 2
28528303 10.1016/j.ejmech.2017.04.079 Leucine-rich repeat serine/threonine-protein kinase 2 2
28528303 10.1016/j.ejmech.2017.04.079 Insulin receptor 2
28528303 10.1016/j.ejmech.2017.04.079 Focal adhesion kinase 1 2
28528303 10.1016/j.ejmech.2017.04.079 Receptor tyrosine-protein kinase erbB-4 2
28528303 10.1016/j.ejmech.2017.04.079 Tyrosine-protein kinase BTK 2
28528303 10.1016/j.ejmech.2017.04.079 Tyrosine-protein kinase Fer 2
28528303 10.1016/j.ejmech.2017.04.079 Tyrosine-protein kinase Blk 2

Data from ChEMBL 36 via Core Engine