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Compound Detail

CHEMBL2180204

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C=CC(=O)N1CCC[C@@H](n2nc(-c3cccc(C(F)(F)F)c3)c3c(N)ncnc32)C1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2180204
Phase Preclinical
Structure Type MOL
InChI Key YEVHVFSOXUYCOT-CQSZACIVSA-N
7
Targets
9
Activities
2
Assay Types
3
PK Parameters
11
Publications
0
Known Names

Molecular Properties

416.4
MW (Da)
3.44
ALogP
6
HBA
1
HBD
89.9
PSA (Ų)
0.66
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C20H19F3N6O
MW 416.41
Aromatic Rings 3
Heavy Atoms 30
NP-Likeness -1.20

Activity Summary

IC50 5 meas. best 7.52
EC50 4 meas. best 6.19

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Epidermal growth factor receptor
CHEMBL203
 IC50 7.52 6.87 30.0 3
Unchecked
CHEMBL612545
 IC50 6.8 6.8 159.0 1
HCC827
CHEMBL4296422
 EC50 6.19 6.19 650.0 1
NCI-H1975
CHEMBL614348
 EC50 5.38 5.38 4160.0 1
A-431
CHEMBL614069
 EC50 4.8 4.8 16000.0 1
Tyrosine-protein kinase ITK/TSK
CHEMBL2959
 IC50 4.75 4.75 17744.0 1
A549
CHEMBL392
 EC50 4.65 4.65 22200.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 2773.0 mL.min-1.g-1 Mus musculus
CL 578.0 mL.min-1.g-1 Homo sapiens
Fu 0.09 - Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Epidermal growth factor receptor IC50 = 30.0 nM 7.52 Inhibition of human recombinant GST-tagged EGFR L858R mutant expressed in baculo... 28853575
Unchecked IC50 = 159.0 nM 6.8 Inhibition of MKK7 beta1 S273D/T275D double mutant (unknown origin) using JNK1 K... 31083997
Epidermal growth factor receptor IC50 = 220.0 nM 6.66 Inhibition of recombinant human GST-tagged EGFR L858R/T790M double mutant expres... 28853575
Epidermal growth factor receptor IC50 = 370.0 nM 6.43 Inhibition of wild type N-terminal GST-fused human EGFR cytoplasmic domain expre... 28853575
HCC827 EC50 = 650.0 nM 6.19 Antiproliferative activity against human HCC827 cells harboring EGFR-delE746_A75... 28853575
NCI-H1975 EC50 = 4160.0 nM 5.38 Antiproliferative activity against human NCI-H1975 cells harboring EGFR-L858R/T7... 28853575
A-431 EC50 = 16000.0 nM 4.8 Antiproliferative activity against human A431 cells expressing wild type EGFR in... 28853575
Tyrosine-protein kinase ITK/TSK IC50 = 17744.0 nM 4.75 Covalent inhibition of ITK in presence of 1 mM ATP 23098091
A549 EC50 = 22200.0 nM 4.65 Antiproliferative activity against human A549 cells harboring KRAS-G12S mutant i... 28853575

Literature References

PubMed DOI Target Context # Activities
28853575 10.1021/acs.jmedchem.7b00515 Epidermal growth factor receptor 3
28853575 10.1021/acs.jmedchem.7b00515 Plasma 3
31083997 10.1021/acs.jmedchem.9b00472 Unchecked 3
28853575 10.1021/acs.jmedchem.7b00515 Unchecked 2
28853575 10.1021/acs.jmedchem.7b00515 No relevant target 2
28853575 10.1021/acs.jmedchem.7b00515 Liver 2
23098091 10.1021/jm301190s Tyrosine-protein kinase ITK/TSK 1
28853575 10.1021/acs.jmedchem.7b00515 A-431 1
28853575 10.1021/acs.jmedchem.7b00515 HCC827 1
28853575 10.1021/acs.jmedchem.7b00515 NCI-H1975 1
28853575 10.1021/acs.jmedchem.7b00515 A549 1

Data from ChEMBL 36 via Core Engine