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Compound Detail

CHEMBL598377

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COc1cc2ncnc(Nc3ccc(F)c(Cl)c3)c2cc1OCCCCCCC(=O)NO
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL598377
Phase Preclinical
Structure Type MOL
InChI Key RQYVKBOWLRVISJ-UHFFFAOYSA-N
14
Targets
28
Activities
1
Assay Types
0
PK Parameters
16
Publications
0
Known Names

Molecular Properties

462.9
MW (Da)
5.01
ALogP
7
HBA
3
HBD
105.6
PSA (Ų)
0.21
QED
1
Ro5 Violations
11
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C22H24ClFN4O4
MW 462.91
Aromatic Rings 3
Heavy Atoms 32
NP-Likeness -1.08

Activity Summary

IC50 28 meas. best 8.51

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Epidermal growth factor receptor
CHEMBL203
 IC50 8.51 8.51 3.1 3
Histone deacetylase
CHEMBL2093865
 IC50 8.19 8.17 6.5 3
Receptor tyrosine-protein kinase erbB-2
CHEMBL1824
 IC50 7.72 7.72 19.0 2
Vascular endothelial growth factor receptor 2
CHEMBL279
 IC50 7.0 7.0 100.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 7.0 6.524 100.0 10
SK-BR-3
CHEMBL613834
 IC50 6.77 6.77 170.0 1
HepG2
CHEMBL395
 IC50 6.54 6.54 290.0 1
SK-HEP1
CHEMBL614912
 IC50 6.48 6.48 330.0 1
MDA-MB-231
CHEMBL400
 IC50 6.43 6.43 370.0 1
BXPC-3
CHEMBL614530
 IC50 6.42 6.42 380.0 1
NCI-H358
CHEMBL614135
 IC50 6.15 6.15 710.0 1
NCI-H460
CHEMBL396
 IC50 6.05 6.05 900.0 1
MCF7
CHEMBL387
 IC50 5.96 5.96 1100.0 1
CAPAN-1
CHEMBL614536
 IC50 5.76 5.76 1730.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Epidermal growth factor receptor IC50 = 3.1 nM 8.51 Inhibition of N-terminal GST-fused human EGFR (His672 to Ala1210 residues) expre... -
Epidermal growth factor receptor IC50 = 3.1 nM 8.51 Inhibition of EGFR (unknown origin) 33077264
Epidermal growth factor receptor IC50 = 3.1 nM 8.51 Inhibition of EGFR 20143778
Histone deacetylase IC50 = 6.5 nM 8.19 Inhibition of HDAC in human HeLa cell nuclear extract 20143778
Histone deacetylase IC50 = 6.5 nM 8.19 Inhibition of HDAC (unknown origin) 33077264
Histone deacetylase IC50 = 7.4 nM 8.13 Inhibition of HDAC in human HeLa nuclear extract using Fluor de Lys as substrate... -
Receptor tyrosine-protein kinase erbB-2 IC50 = 19.0 nM 7.72 Inhibition of HER2 20143778
Receptor tyrosine-protein kinase erbB-2 IC50 = 19.0 nM 7.72 Inhibition of HER2 (unknown origin) 33077264
Vascular endothelial growth factor receptor 2 IC50 = 100.0 nM 7.0 Inhibition of N-terminal GST-His6-thrombin cleavage site-fused human VEGFR2 (Asp... -
NON-PROTEIN TARGET IC50 = 100.0 nM 7.0 Cytotoxicity against human NCI-H1975 cells assessed as growth inhibition by meas... -
NON-PROTEIN TARGET IC50 = 100.0 nM 7.0 Cytotoxicity against human NCI-H2122 cells assessed as growth inhibition by meas... -
NON-PROTEIN TARGET IC50 = 100.0 nM 7.0 Cytotoxicity against human NCI-H358 cells assessed as growth inhibition by measu... -
NON-PROTEIN TARGET IC50 = 100.0 nM 7.0 Cytotoxicity against human NCI-H460 cells assessed as growth inhibition by measu... -
SK-BR-3 IC50 = 170.0 nM 6.77 Antiproliferative activity against human SK-BR-3 cells after hrs by ATP content ... 20143778
HepG2 IC50 = 290.0 nM 6.54 Antiproliferative activity against human HepG2 cells after hrs by ATP content as... 20143778
SK-HEP1 IC50 = 330.0 nM 6.48 Antiproliferative activity against human SKHEP1 cells after hrs by ATP content a... 20143778
MDA-MB-231 IC50 = 370.0 nM 6.43 Antiproliferative activity against human MDA-MB-231 cells after hrs by ATP conte... 20143778
BXPC-3 IC50 = 380.0 nM 6.42 Antiproliferative activity against human BxPC3 cells after hrs by ATP content as... 20143778
NON-PROTEIN TARGET IC50 = 380.0 nM 6.42 Cytotoxicity against human BxPC3 cells assessed as growth inhibition by measurin... -
NON-PROTEIN TARGET IC50 = 440.0 nM 6.36 Cytotoxicity against human NCI-H1703 cells assessed as growth inhibition by meas... -

Literature References

PubMed DOI Target Context # Activities
20143778 10.1021/jm901453q NON-PROTEIN TARGET 2
20143778 10.1021/jm901453q Histone deacetylase 1
20143778 10.1021/jm901453q Epidermal growth factor receptor 1
20143778 10.1021/jm901453q Receptor tyrosine-protein kinase erbB-2 1
20143778 10.1021/jm901453q NCI-H358 1
20143778 10.1021/jm901453q NCI-H460 1
20143778 10.1021/jm901453q HepG2 1
20143778 10.1021/jm901453q SK-HEP1 1
20143778 10.1021/jm901453q CAPAN-1 1
20143778 10.1021/jm901453q BXPC-3 1
20143778 10.1021/jm901453q MCF7 1
20143778 10.1021/jm901453q MDA-MB-231 1
20143778 10.1021/jm901453q SK-BR-3 1
33077264 10.1016/j.ejmech.2020.112904 Histone deacetylase 1
33077264 10.1016/j.ejmech.2020.112904 Epidermal growth factor receptor 1
33077264 10.1016/j.ejmech.2020.112904 Receptor tyrosine-protein kinase erbB-2 1

Data from ChEMBL 36 via Core Engine