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Compound Detail

CHEMBL1630109

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O=C(/C=C/c1cccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)c1)NO
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1630109
Phase Preclinical
Structure Type MOL
InChI Key HRIQVCCRXNQUAH-KPKJPENVSA-N
19
Targets
24
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

541.0
MW (Da)
6.93
ALogP
6
HBA
3
HBD
96.4
PSA (Ų)
0.11
QED
2
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C30H22ClFN4O3
MW 540.98
Aromatic Rings 5
Heavy Atoms 39
NP-Likeness -1.07

Activity Summary

IC50 23 meas. best 7.96
EC50 1 meas. best 5.33

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Receptor tyrosine-protein kinase erbB-2
CHEMBL1824
 IC50 7.96 7.96 11.0 1
Epidermal growth factor receptor
CHEMBL203
 IC50 7.75 7.025 18.0 2
Histone deacetylase 1
CHEMBL325
 IC50 7.46 7.46 35.0 2
Histone deacetylase
CHEMBL2093865
 IC50 7.33 7.33 47.0 1
Histone deacetylase 3
CHEMBL1829
 IC50 7.18 7.18 66.0 2
Histone deacetylase 6
CHEMBL1865
 IC50 7.07 7.07 86.0 2
SK-BR-3
CHEMBL613834
 IC50 6.46 6.46 350.0 1
CAL-27
CHEMBL1075408
 IC50 6.23 6.23 590.0 1
Histone deacetylase 8
CHEMBL3192
 IC50 6.2 6.2 630.0 2
A-431
CHEMBL614069
 IC50 6.14 6.14 720.0 1
Cyclin-dependent kinase 2
CHEMBL301
 IC50 6.04 6.04 920.0 1
HeLa
CHEMBL399
 IC50 6.01 6.01 970.0 1
SK-OV-3
CHEMBL614925
 IC50 6.0 6.0 1000.0 1
A549
CHEMBL392
 IC50 5.92 5.92 1200.0 1
Platelet-derived growth factor receptor beta
CHEMBL1913
 IC50 5.6 5.6 2500.0 1
Insulin receptor
CHEMBL1981
 IC50 5.44 5.44 3600.0 1
Unchecked
CHEMBL612545
 EC50 5.33 5.33 4700.0 1
Tyrosine-protein kinase ABL1
CHEMBL1862
 IC50 5.28 5.28 5300.0 1
Serine/threonine-protein kinase PLK1
CHEMBL3024
 IC50 5.17 5.17 6800.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Receptor tyrosine-protein kinase erbB-2 IC50 = 11.0 nM 7.96 Inhibition of HER2 by flash plate based radioactive enzyme assay 21080629
Epidermal growth factor receptor IC50 = 18.0 nM 7.75 Inhibition of EGFR by flash plate based radioactive enzyme assay 21080629
Histone deacetylase 1 IC50 = 35.0 nM 7.46 Inhibition of human recombinant HDAC1 expressed in HEK293 cells 21080629
Histone deacetylase 1 IC50 = 35.0 nM 7.46 Inhibition of HDAC1 (unknown origin) 27318122
Histone deacetylase IC50 = 47.0 nM 7.33 Inhibition of HDAC in human HeLa cell nuclear extracts 21080629
Histone deacetylase 3 IC50 = 66.0 nM 7.18 Inhibition of Flag tagged human recombinant HDAC3 expressed in Sf21 cells coexpr... 21080629
Histone deacetylase 3 IC50 = 66.0 nM 7.18 Inhibition of HDAC3 (unknown origin) 27318122
Histone deacetylase 6 IC50 = 86.0 nM 7.07 Inhibition of human recombinant HDAC6 expressed in HEK293 cells 21080629
Histone deacetylase 6 IC50 = 86.0 nM 7.07 Inhibition of HDAC6 (unknown origin) 27318122
SK-BR-3 IC50 = 350.0 nM 6.46 Cytotoxicity against human SKBR3 cells overexpressing HER2 by resazurin dye redu... 21080629
Epidermal growth factor receptor IC50 = 500.0 nM 6.3 Inhibition of EGF-induced EGFR phosphorylation in human CAL27 cells overexpressi... 21080629
CAL-27 IC50 = 590.0 nM 6.23 Cytotoxicity against human CAL27 cells overexpressing EGFR by resazurin dye redu... 21080629
Histone deacetylase 8 IC50 = 630.0 nM 6.2 Inhibition of Flag tagged human recombinant HDAC8 expressed in Sf21 cells 21080629
Histone deacetylase 8 IC50 = 630.0 nM 6.2 Inhibition of HDAC8 (unknown origin) 27318122
A-431 IC50 = 720.0 nM 6.14 Cytotoxicity against human A431 cells overexpressing EGFR by resazurin dye reduc... 21080629
Cyclin-dependent kinase 2 IC50 = 920.0 nM 6.04 Inhibition of CDK2 by flash plate based radioactive enzyme assay 21080629
HeLa IC50 = 970.0 nM 6.01 Cytotoxicity against human HeLa cells overexpressing HDAC by resazurin dye reduc... 21080629
SK-OV-3 IC50 = 1000.0 nM 6.0 Cytotoxicity against human SKOV3 cells overexpressing HER2 by resazurin dye redu... 21080629
A549 IC50 = 1200.0 nM 5.92 Cytotoxicity against human A549 cells overexpressing HDAC by resazurin dye reduc... 21080629
Platelet-derived growth factor receptor beta IC50 = 2500.0 nM 5.6 Inhibition of PDGFRbeta by flash plate based radioactive enzyme assay 21080629

Literature References

PubMed DOI Target Context # Activities
21080629 10.1021/jm100665z Unchecked 2
21080629 10.1021/jm100665z Histone deacetylase 2
21080629 10.1021/jm100665z Epidermal growth factor receptor 2
27318122 10.1016/j.ejmech.2016.05.047 Histone deacetylase 8 1
27318122 10.1016/j.ejmech.2016.05.047 Histone deacetylase 1 1
21080629 10.1021/jm100665z SK-OV-3 1
21080629 10.1021/jm100665z SK-BR-3 1
21080629 10.1021/jm100665z CAL-27 1
21080629 10.1021/jm100665z A-431 1
21080629 10.1021/jm100665z HeLa 1
21080629 10.1021/jm100665z A549 1
21080629 10.1021/jm100665z Serine/threonine-protein kinase PLK1 1
21080629 10.1021/jm100665z Cyclin-dependent kinase 2 1
21080629 10.1021/jm100665z Tyrosine-protein kinase ABL1 1
21080629 10.1021/jm100665z Insulin receptor 1
21080629 10.1021/jm100665z Platelet-derived growth factor receptor beta 1
21080629 10.1021/jm100665z Receptor tyrosine-protein kinase erbB-2 1
21080629 10.1021/jm100665z Histone deacetylase 8 1
21080629 10.1021/jm100665z Histone deacetylase 3 1
21080629 10.1021/jm100665z Histone deacetylase 6 1

Data from ChEMBL 36 via Core Engine