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Compound Detail

CHEMBL4090601

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C=CC(=O)N1CCC[C@@H](n2nc(-c3ccc4ccccc4c3)c3c(N)ncnc32)C1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4090601
Phase Preclinical
Structure Type MOL
InChI Key UTTWFQUHUQLZGF-GOSISDBHSA-N
5
Targets
11
Activities
2
Assay Types
3
PK Parameters
15
Publications
0
Known Names

Molecular Properties

398.5
MW (Da)
3.58
ALogP
6
HBA
1
HBD
89.9
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 C23H22N6O
MW 398.47
Aromatic Rings 4
Heavy Atoms 30
NP-Likeness -0.78

Activity Summary

IC50 8 meas. best 9.0
EC50 3 meas. best 6.85

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Epidermal growth factor receptor
CHEMBL203
 IC50 9.0 7.64 1.0 7
Unchecked
CHEMBL612545
 IC50 6.95 6.95 113.0 1
NCI-H1975
CHEMBL614348
 EC50 6.85 6.85 140.0 1
A-431
CHEMBL614069
 EC50 5.44 5.44 3600.0 1
A549
CHEMBL392
 EC50 4.94 4.94 11600.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 2311.0 mL.min-1.g-1 Mus musculus
CL 770.0 mL.min-1.g-1 Homo sapiens
Fu 0.02 - Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Epidermal growth factor receptor IC50 = 1.0 nM 9.0 Inhibition of human recombinant GST-tagged EGFR L858R mutant expressed in baculo... 28853575
Epidermal growth factor receptor IC50 = 16.0 nM 7.8 Inhibition of wild type N-terminal GST-fused human EGFR cytoplasmic domain expre... 29136465
Epidermal growth factor receptor IC50 = 16.0 nM 7.8 Inhibition of wild type EGFR (unknown origin) 36324498
Epidermal growth factor receptor IC50 = 20.0 nM 7.7 Inhibition of wild type N-terminal GST-fused human EGFR cytoplasmic domain expre... 28853575
Epidermal growth factor receptor IC50 = 88.0 nM 7.06 Inhibition of recombinant human EGFR L858R/T790M/C797S mutant using TK-substrate... 29136465
Epidermal growth factor receptor IC50 = 88.0 nM 7.06 Inhibition of EGFR L858R/T790M/C797S triple mutant (unknown origin) 34323489
Epidermal growth factor receptor IC50 = 88.0 nM 7.06 Inhibition of EGFR L858R T790M/C797S mutant (unknown origin) 36324498
Unchecked IC50 = 113.0 nM 6.95 Inhibition of MKK7 beta1 S273D/T275D double mutant (unknown origin) using JNK1 K... 31083997
NCI-H1975 EC50 = 140.0 nM 6.85 Antiproliferative activity against human NCI-H1975 cells harboring EGFR-L858R/T7... 28853575
A-431 EC50 = 3600.0 nM 5.44 Antiproliferative activity against human A431 cells expressing wild type EGFR in... 28853575
A549 EC50 = 11600.0 nM 4.94 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 4
28853575 10.1021/acs.jmedchem.7b00515 ADMET 3
28853575 10.1021/acs.jmedchem.7b00515 Plasma 3
29136465 10.1021/acs.jmedchem.7b01310 Epidermal growth factor receptor 3
31083997 10.1021/acs.jmedchem.9b00472 Unchecked 3
36324498 10.1039/d2md00139j Epidermal growth factor receptor 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
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
29136465 10.1021/acs.jmedchem.7b01310 NCI-H1975 1
34323489 10.1021/acs.jmedchem.1c00876 Epidermal growth factor receptor 1

Data from ChEMBL 36 via Core Engine