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Compound Detail

CHEMBL4094959

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C=CC(=O)N1CCC[C@@H](n2nc(-c3cn(C)c4ccccc34)c3c(N)ncnc32)C1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4094959
Phase Preclinical
Structure Type MOL
InChI Key KFYRXHYWURCCBT-CQSZACIVSA-N
6
Targets
16
Activities
2
Assay Types
14
PK Parameters
17
Publications
0
Known Names

Molecular Properties

401.5
MW (Da)
2.92
ALogP
7
HBA
1
HBD
94.9
PSA (Ų)
0.53
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 C22H23N7O
MW 401.47
Aromatic Rings 4
Heavy Atoms 30
NP-Likeness -0.78

Activity Summary

IC50 12 meas. best 8.72
EC50 4 meas. best 7.05

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Epidermal growth factor receptor
CHEMBL203
 IC50 8.72 7.87 1.9 10
HCC827
CHEMBL4296422
 EC50 7.05 7.05 90.0 1
NCI-H1975
CHEMBL614348
 EC50 6.64 6.64 230.0 1
Unchecked
CHEMBL612545
 IC50 6.52 6.52 302.0 2
A-431
CHEMBL614069
 EC50 5.17 5.17 6780.0 1
A549
CHEMBL392
 EC50 4.63 4.63 23300.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 121.0 ng.hr.mL-1 Mus musculus
AUC 1888.0 ng.hr.mL-1 Mus musculus
AUC 29.0 ng.hr.mL-1 Mus musculus
CL 1980.0 mL.min-1.g-1 Mus musculus
CL 462.0 mL.min-1.g-1 Homo sapiens
CL 276.67 mL.min-1.kg-1 Mus musculus
Cmax 11305.95 nM Mus musculus
Cmax 94.65 nM Mus musculus
F 156.0 % Mus musculus
F 2.4 % Mus musculus
Fu 0.12 - Mus musculus
T1/2 0.6 hr Mus musculus
T1/2 0.24 hr Mus musculus
T1/2 0.59 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Epidermal growth factor receptor IC50 = 1.9 nM 8.72 Inhibition of EGFR T790M/C797S mutant (unknown origin) 36324498
Epidermal growth factor receptor IC50 = 2.0 nM 8.7 Inhibition of human recombinant GST-tagged EGFR L858R mutant expressed in baculo... 28853575
Epidermal growth factor receptor IC50 = 2.5 nM 8.6 Inhibition of N-terminal GST-fused human EGFR cytoplasmic domain T790M/C797S mut... 29136465
Epidermal growth factor receptor IC50 = 3.0 nM 8.52 Inhibition of recombinant human GST-tagged EGFR L858R/T790M double mutant expres... 28853575
Epidermal growth factor receptor IC50 = 3.0 nM 8.52 Inhibition of EGFR L858R/T790M double mutant (unknown origin) by HTRF assay 30768270
Epidermal growth factor receptor IC50 = 35.0 nM 7.46 Inhibition of wild type N-terminal GST-fused human EGFR cytoplasmic domain expre... 29136465
Epidermal growth factor receptor IC50 = 35.0 nM 7.46 Inhibition of wild type EGFR (unknown origin) by HTRF assay 30768270
Epidermal growth factor receptor IC50 = 40.0 nM 7.4 Inhibition of wild type N-terminal GST-fused human EGFR cytoplasmic domain expre... 28853575
Epidermal growth factor receptor IC50 = 58.0 nM 7.24 Inhibition of wild type EGFR (unknown origin) 36324498
HCC827 EC50 = 90.0 nM 7.05 Antiproliferative activity against human HCC827 cells harboring EGFR-delE746_A75... 28853575
NCI-H1975 EC50 = 230.0 nM 6.64 Antiproliferative activity against human NCI-H1975 cells harboring EGFR-L858R/T7... 28853575
Unchecked IC50 = 302.0 nM 6.52 Inhibition of MKK7 beta1 S273D/T275D double mutant (unknown origin) using JNK1 K... 31083997
Unchecked IC50 = 302.0 nM 6.52 Inhibition of N-terminal His-tagged MKK7 beta1 S273D/T275D double mutant (unknow... 30768270
Epidermal growth factor receptor IC50 = 838.0 nM 6.08 Inhibition of recombinant human EGFR L858R/T790M/C797S mutant using TK-substrate... 29136465
A-431 EC50 = 6780.0 nM 5.17 Antiproliferative activity against human A431 cells expressing wild type EGFR in... 28853575
A549 EC50 = 23300.0 nM 4.63 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 Mus musculus 19
28853575 10.1021/acs.jmedchem.7b00515 Unchecked 4
28853575 10.1021/acs.jmedchem.7b00515 Epidermal growth factor receptor 4
28853575 10.1021/acs.jmedchem.7b00515 Plasma 3
31083997 10.1021/acs.jmedchem.9b00472 Unchecked 3
29136465 10.1021/acs.jmedchem.7b01310 Epidermal growth factor receptor 3
28853575 10.1021/acs.jmedchem.7b00515 ADMET 3
28853575 10.1021/acs.jmedchem.7b00515 No relevant target 2
28853575 10.1021/acs.jmedchem.7b00515 Liver 2
30768270 10.1021/acs.jmedchem.9b00102 Epidermal growth factor receptor 2
36324498 10.1039/d2md00139j Epidermal growth factor receptor 2
28853575 10.1021/acs.jmedchem.7b00515 A549 1
28853575 10.1021/acs.jmedchem.7b00515 NCI-H1975 1
28853575 10.1021/acs.jmedchem.7b00515 HCC827 1
29136465 10.1021/acs.jmedchem.7b01310 NCI-H1975 1
28853575 10.1021/acs.jmedchem.7b00515 A-431 1
30768270 10.1021/acs.jmedchem.9b00102 Unchecked 1

Data from ChEMBL 36 via Core Engine