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Compound Detail

CHEMBL111038

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COc1cc2ncc(C#N)c(Nc3cccc(Br)c3)c2cc1OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL111038
Phase Preclinical
Structure Type MOL
InChI Key CQKFTSMPIIYOBX-UHFFFAOYSA-N
7
Targets
15
Activities
2
Assay Types
0
PK Parameters
13
Publications
0
Known Names

Molecular Properties

384.2
MW (Da)
4.63
ALogP
5
HBA
1
HBD
67.2
PSA (Ų)
0.71
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C18H14BrN3O2
MW 384.23
Aromatic Rings 3
Heavy Atoms 24
NP-Likeness -1.21

Activity Summary

IC50 13 meas. best 8.12
Kd 2 meas. best 8.62

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Epidermal growth factor receptor
CHEMBL203
 Kd 8.62 8.62 2.4 1
Epidermal growth factor receptor
CHEMBL203
 IC50 8.12 7.066 7.5 5
Cyclin-G-associated kinase
CHEMBL4355
 Kd 7.92 7.92 12.0 1
Cyclin-G-associated kinase
CHEMBL4355
 IC50 6.89 6.89 130.0 1
Epidermal growth factor receptor and ErbB2 (HER1 and HER2)
CHEMBL2111431
 IC50 6.72 6.72 190.0 1
SK-BR-3
CHEMBL613834
 IC50 6.32 6.32 480.0 1
A-431
CHEMBL614069
 IC50 6.11 6.11 780.0 1
SW-620
CHEMBL612262
 IC50 5.43 5.43 3720.0 1
Unchecked
CHEMBL612545
 IC50 5.06 4.9567 8800.0 3

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Epidermal growth factor receptor Kd = 2.4 nM 8.62 Binding affinity to wild-type human partial length EGFR (R669 to V1011 residues)... 30973735
Epidermal growth factor receptor IC50 = 7.5 nM 8.12 Inhibition of EGFR (unknown origin) 36375337
Cyclin-G-associated kinase Kd = 12.0 nM 7.92 Binding affinity to wild-type human partial length GAK (G13 to Y338 residues) ex... 30973735
Epidermal growth factor receptor IC50 = 90.0 nM 7.05 Inhibition of EGFR in human A431 cells assessed as reduction in EGF-stimulated E... 30973735
Cyclin-G-associated kinase IC50 = 130.0 nM 6.89 Inhibition of tracer 5 binding to human N-terminal nano luciferase-fused GAK exp... 30973735
Epidermal growth factor receptor and ErbB2 (HER1 and HER2) IC50 = 190.0 nM 6.72 Concentration needed to inhibit the autophosphorylation of the cytoplasmic domai... 10966743
Epidermal growth factor receptor IC50 = 190.0 nM 6.72 Inhibition of autophosphorylation of cytoplasmic domain of epidermal growth fact... 12502359
Epidermal growth factor receptor IC50 = 190.55 nM 6.72 Inhibition autophosphorylation of EGFR in human DiFi cells after 2 hrs by ELISA 17689836
Epidermal growth factor receptor IC50 = 190.0 nM 6.72 Inhibition of human EGFR kinase activity 21413808
SK-BR-3 IC50 = 480.0 nM 6.32 Concentration needed to inhibit 50% growth of human SKBr3 (breast carcinoma) cel... 10966743
A-431 IC50 = 780.0 nM 6.11 Concentration needed to inhibit 50% growth of the human A431 (epidermoid carcino... 10966743
SW-620 IC50 = 3720.0 nM 5.43 Concentration needed to inhibit 50% growth of human SW620 (colon carcinoma) cell... 10966743
Unchecked IC50 = 8800.0 nM 5.06 Antiproliferative activity against human UCH1 cells measured after 72 hrs by ala... 30973735
Unchecked IC50 = 11000.0 nM 4.96 Cytotoxicity in human WS1 cells assessed as reduction in cell viability incubate... 31378571
Unchecked IC50 = 14000.0 nM 4.85 Cytotoxicity against human WS1 cells measured after 72 hrs by alamar blue assay 30973735

Literature References

PubMed DOI Target Context # Activities
31378571 10.1016/j.bmcl.2019.07.012 Mycobacterium tuberculosis 5
30973735 10.1021/acs.jmedchem.9b00350 Unchecked 3
30973735 10.1021/acs.jmedchem.9b00350 Epidermal growth factor receptor 2
30973735 10.1021/acs.jmedchem.9b00350 Cyclin-G-associated kinase 2
10966743 10.1021/jm000206a Epidermal growth factor receptor and ErbB2 (HER1 and HER2) 1
10966743 10.1021/jm000206a A-431 1
10966743 10.1021/jm000206a SK-BR-3 1
10966743 10.1021/jm000206a SW-620 1
12502359 10.1021/jm020241c Epidermal growth factor receptor 1
17689836 10.1016/j.ejmech.2007.06.006 Epidermal growth factor receptor 1
21413808 10.1021/jm1013693 Epidermal growth factor receptor 1
31378571 10.1016/j.bmcl.2019.07.012 Unchecked 1
36375337 10.1016/j.ejmech.2022.114889 Epidermal growth factor receptor 1

Data from ChEMBL 36 via Core Engine