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Compound Detail

CHEMBL4642874

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O=C(NO)c1ccc(NC(=O)C2(c3ccc4ccccc4c3)CCOCC2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4642874
Phase Preclinical
Structure Type MOL
InChI Key VNRCXPZNHIIBGH-UHFFFAOYSA-N
11
Targets
18
Activities
2
Assay Types
0
PK Parameters
12
Publications
0
Known Names

Molecular Properties

390.4
MW (Da)
3.65
ALogP
4
HBA
3
HBD
87.7
PSA (Ų)
0.47
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C23H22N2O4
MW 390.44
Aromatic Rings 3
Heavy Atoms 29
NP-Likeness -0.99

Activity Summary

IC50 11 meas. best 9.14
EC50 7 meas. best 7.22

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase 1
CHEMBL325
 IC50 9.14 9.14 0.7 1
Histone deacetylase 3
CHEMBL1829
 IC50 8.7 8.7 2.0 1
Histone deacetylase 2
CHEMBL1937
 IC50 8.1 8.1 8.0 1
MM96L
CHEMBL614170
 IC50 7.7 7.7 20.0 1
HeLa
CHEMBL399
 IC50 7.52 7.52 30.0 1
HT-29
CHEMBL384
 IC50 7.4 7.4 40.0 1
Histone deacetylase 8
CHEMBL3192
 IC50 7.36 7.36 44.0 1
MM96L
CHEMBL614170
 EC50 7.22 7.22 60.0 1
A549
CHEMBL392
 IC50 7.0 7.0 100.0 1
MDA-MB-231
CHEMBL400
 IC50 7.0 7.0 100.0 1
HT-29
CHEMBL384
 EC50 6.7 6.7 200.0 1
Histone deacetylase 1
CHEMBL325
 EC50 6.7 6.7 200.0 1
Histone deacetylase 7
CHEMBL2716
 IC50 6.68 6.68 210.0 1
MDA-MB-231
CHEMBL400
 EC50 6.52 6.52 300.0 1
NFF
CHEMBL614198
 IC50 6.4 6.4 400.0 1
HeLa
CHEMBL399
 EC50 6.16 6.16 700.0 1
A549
CHEMBL392
 EC50 5.58 5.58 2600.0 1
NFF
CHEMBL614198
 EC50 5.37 5.37 4300.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase 1 IC50 = 0.72 nM 9.14 Inhibition of human recombinant HDAC1 pre-incubated for 30 mins before Ac-Leu- G... 32383881
Histone deacetylase 3 IC50 = 2.0 nM 8.7 Inhibition of human recombinant HDAC3 pre-incubated for 30 mins before Ac-Leu- G... 32383881
Histone deacetylase 2 IC50 = 8.0 nM 8.1 Inhibition of human recombinant HDAC2 pre-incubated for 30 mins before Ac-Leu- G... 32383881
MM96L IC50 = 20.0 nM 7.7 Cytotoxicity against human MM96L cells assessed as reduction in cell viability i... 32383881
HeLa IC50 = 30.0 nM 7.52 Cytotoxicity against human HeLa cells assessed as reduction in cell viability in... 32383881
HT-29 IC50 = 40.0 nM 7.4 Cytotoxicity against human HT-29 cells assessed as reduction in cell viability i... 32383881
Histone deacetylase 8 IC50 = 44.0 nM 7.36 Inhibition of human recombinant HDAC8 pre-incubated for 30 mins before Ac-Leu- G... 32383881
MM96L EC50 = 60.0 nM 7.22 Cytotoxicity against human MM96L cells assessed as increase in intracellular cas... 32383881
MDA-MB-231 IC50 = 100.0 nM 7.0 Cytotoxicity against human MDA-MB-231 cells assessed as reduction in cell viabil... 32383881
A549 IC50 = 100.0 nM 7.0 Cytotoxicity against human A549 cells assessed as reduction in cell viability in... 32383881
HT-29 EC50 = 200.0 nM 6.7 Cytotoxicity against human HT-29 cells assessed as increase in intracellular cas... 32383881
Histone deacetylase 1 EC50 = 200.0 nM 6.7 Inhibition of HDAC1 in human MM96L cells assessed as activation of histone H4 ac... 32383881
Histone deacetylase 7 IC50 = 210.0 nM 6.68 Inhibition of human recombinant HDAC7 pre-incubated for 15 mins before Ac-Leu-Gl... 32383881
MDA-MB-231 EC50 = 300.0 nM 6.52 Cytotoxicity against human MDA-MB-231 cells assessed as increase in intracellula... 32383881
NFF IC50 = 400.0 nM 6.4 Cytotoxicity against human NFF cells assessed as reduction in cell viability inc... 32383881
HeLa EC50 = 700.0 nM 6.16 Cytotoxicity against human HeLa cells assessed as increase in intracellular casp... 32383881
A549 EC50 = 2600.0 nM 5.58 Cytotoxicity against human A549 cells assessed as increase in intracellular casp... 32383881
NFF EC50 = 4300.0 nM 5.37 Cytotoxicity against human NFF cells assessed as increase in intracellular caspa... 32383881

Literature References

PubMed DOI Target Context # Activities
32383881 10.1021/acs.jmedchem.0c00230 Unchecked 14
32383881 10.1021/acs.jmedchem.0c00230 Histone deacetylase 1 5
32383881 10.1021/acs.jmedchem.0c00230 A549 4
32383881 10.1021/acs.jmedchem.0c00230 HT-29 4
32383881 10.1021/acs.jmedchem.0c00230 HeLa 4
32383881 10.1021/acs.jmedchem.0c00230 MDA-MB-231 4
32383881 10.1021/acs.jmedchem.0c00230 MM96L 4
32383881 10.1021/acs.jmedchem.0c00230 NFF 2
32383881 10.1021/acs.jmedchem.0c00230 Histone deacetylase 2 1
32383881 10.1021/acs.jmedchem.0c00230 Histone deacetylase 3 1
32383881 10.1021/acs.jmedchem.0c00230 Histone deacetylase 8 1
32383881 10.1021/acs.jmedchem.0c00230 Histone deacetylase 7 1

Data from ChEMBL 36 via Core Engine