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Compound Detail

CHEMBL91867

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CC#CC(=O)Nc1ccc2ncnc(Nc3cccc(Br)c3)c2c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL91867
Phase Preclinical
Structure Type MOL
InChI Key BTYYWOYVBXILOJ-UHFFFAOYSA-N
16
Targets
38
Activities
2
Assay Types
1
PK Parameters
20
Publications
0
Known Names

Molecular Properties

381.2
MW (Da)
4.10
ALogP
4
HBA
2
HBD
66.9
PSA (Ų)
0.67
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 C18H13BrN4O
MW 381.23
Aromatic Rings 3
Heavy Atoms 24
NP-Likeness -1.22

Activity Summary

IC50 36 meas. best 9.7
EC50 2 meas. best 7.3

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Epidermal growth factor receptor
CHEMBL203
 IC50 9.7 8.8329 0.2 7
Proto-oncogene tyrosine-protein kinase Src
CHEMBL3655
 IC50 9.0 9.0 1.0 1
HCC827
CHEMBL4296422
 IC50 8.7 8.7 2.0 1
BaF3
CHEMBL614524
 IC50 8.7 7.119 2.0 10
PC-9
CHEMBL614102
 IC50 8.7 8.7 2.0 1
Receptor tyrosine-protein kinase erbB-4
CHEMBL3009
 IC50 7.92 7.92 12.0 1
Receptor tyrosine-protein kinase erbB-2
CHEMBL1824
 IC50 7.77 7.095 17.0 2
SK-BR-3
CHEMBL613834
 IC50 7.77 7.77 17.0 1
NCI-H3255
CHEMBL4296476
 IC50 7.64 7.64 23.0 1
Epidermal growth factor receptor
CHEMBL203
 EC50 7.3 6.65 50.0 2
A-431
CHEMBL614069
 IC50 7.1 7.1 79.0 1
Unchecked
CHEMBL612545
 IC50 7.06 6.6825 88.0 4
Calu-3
CHEMBL614534
 IC50 7.0 7.0 100.0 1
Broad substrate specificity ATP-binding cassette transporter ABCG2
CHEMBL5393
 IC50 6.7 6.7 200.0 1
Schistosoma mansoni
CHEMBL612893
 IC50 6.16 5.795 700.0 2
NCI-H1975
CHEMBL614348
 IC50 6.07 6.07 850.0 1
SW-620
CHEMBL612262
 IC50 5.82 5.82 1500.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 3.317 hr -

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Epidermal growth factor receptor IC50 = 0.2 nM 9.7 Inhibition of erbB1 fusion protein expressed in baculovirus by ELISA 16480284
Epidermal growth factor receptor IC50 = 0.25 nM 9.6 Inhibition of epidermal growth factor receptor kinase (unknown origin) using [33... 26256032
Epidermal growth factor receptor IC50 = 0.37 nM 9.43 Inhibition of EGFR 22621397
Proto-oncogene tyrosine-protein kinase Src IC50 = 1.0 nM 9.0 Inhibition of chicken c-Src T338G mutant 22621397
HCC827 IC50 = 2.0 nM 8.7 Antiproliferative activity against human HCC827 cells harboring EGFR Del E746_A7... 20033049
PC-9 IC50 = 2.0 nM 8.7 Antiproliferative activity against human PC-9 cells harboring EGFR Del E746_A750... 20033049
BaF3 IC50 = 2.0 nM 8.7 Antiproliferative activity against mouse BaF3 cells harboring EGFR E746_A750 mut... 20033049
BaF3 IC50 = 2.0 nM 8.7 Antiproliferative activity against mouse BaF3 cells harboring EGFR vIII mutant a... 20033049
Epidermal growth factor receptor IC50 = 2.5 nM 8.6 Inhibition of EGF stimulated human erbB1 autophosphorylation in NIH3T3 cells 16480284
BaF3 IC50 = 4.0 nM 8.4 Antiproliferative activity against mouse BaF3 cells harboring EGFR L858R mutant ... 20033049
Epidermal growth factor receptor IC50 = 5.0 nM 8.3 Inhibition of EGF-induced autophosphorylation of EGFR in human A431 cells 22621397
Epidermal growth factor receptor IC50 = 8.0 nM 8.1 Inhibition of epidermal growth factor receptor using enzyme assay 11495584
Epidermal growth factor receptor IC50 = 8.0 nM 8.1 Inhibition of human recombinant EGFR 19170633
BaF3 IC50 = 8.0 nM 8.1 Antiproliferative activity against mouse BaF3 cells harboring ERBB2 Ins G776V,C ... 20033049
Receptor tyrosine-protein kinase erbB-4 IC50 = 12.0 nM 7.92 Inhibition of erbB4 fusion protein expressed in baculovirus by ELISA 16480284
SK-BR-3 IC50 = 17.0 nM 7.77 Inhibition of cell growth of SKBr3 cell lines using cell-based assay 11495584
Receptor tyrosine-protein kinase erbB-2 IC50 = 17.0 nM 7.77 Inhibition of erbB2 fusion protein expressed in baculovirus by ELISA 16480284
NCI-H3255 IC50 = 23.0 nM 7.64 Antiproliferative activity against human NCI-H3255 cells harboring EGFR L858R mu... 20033049
BaF3 IC50 = 26.0 nM 7.58 Antiproliferative activity against mouse BaF3 cells harboring wildtype ERBB2 ass... 20033049
Epidermal growth factor receptor EC50 = 50.0 nM 7.3 Inhibition of EGFR by cellular assay 18077425

Literature References

PubMed DOI Target Context # Activities
18077425 10.1073/pnas.0707498104 NON-PROTEIN TARGET 115
20033049 10.1038/nature08622 BaF3 11
20033049 10.1038/nature08622 Unchecked 5
18077425 10.1073/pnas.0707498104 COLO 3
18077425 10.1073/pnas.0707498104 Epidermal growth factor receptor 3
33479649 10.1039/D0MD00062K Schistosoma mansoni 3
15155841 10.1124/mol.65.6.1485 Broad substrate specificity ATP-binding cassette transporter ABCG2 2
20033049 10.1038/nature08622 RAC-alpha serine/threonine-protein kinase 2
16480284 10.1021/jm050936o Epidermal growth factor receptor 2
20033049 10.1038/nature08622 Mitogen-activated protein kinase; ERK1/ERK2 2
22621397 10.1021/jm3003203 Proto-oncogene tyrosine-protein kinase Src 2
22621397 10.1021/jm3003203 Epidermal growth factor receptor 2
20033049 10.1038/nature08622 Epidermal growth factor receptor 2
18077425 10.1073/pnas.0707498104 NCI-H2170 1
18077425 10.1073/pnas.0707498104 NCI-H23 1
18077425 10.1073/pnas.0707498104 NCI-H2228 1
16480284 10.1021/jm050936o Receptor tyrosine-protein kinase erbB-4 1
16480284 10.1021/jm050936o Receptor tyrosine-protein kinase erbB-2 1
11495584 10.1021/jm0005555 SW-620 1
11495584 10.1021/jm0005555 A-431 1

Data from ChEMBL 36 via Core Engine