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Compound Detail

CHEMBL2178342

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O=C(NO)c1cccc(-c2cn(CSc3ccccc3)nn2)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2178342
Phase Preclinical
Structure Type MOL
InChI Key DORPIZJGSLWDIY-UHFFFAOYSA-N
8
Targets
19
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

326.4
MW (Da)
2.81
ALogP
6
HBA
2
HBD
80.0
PSA (Ų)
0.43
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C16H14N4O2S
MW 326.38
Aromatic Rings 3
Heavy Atoms 23
NP-Likeness -1.66

Activity Summary

IC50 17 meas. best 7.36
Kd 2 meas. best 7.09

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase 8
CHEMBL3192
 IC50 7.36 6.8617 44.0 6
Histone deacetylase 8
CHEMBL3797017
 Kd 7.09 7.09 81.7 1
Histone deacetylase 8
CHEMBL3192
 Kd 7.05 7.05 89.6 1
Histone deacetylase 8
CHEMBL3797017
 IC50 7.02 7.02 95.4 1
Unchecked
CHEMBL612545
 IC50 6.56 6.2433 274.0 3
Histone deacetylase 6
CHEMBL1865
 IC50 5.62 5.62 2400.0 1
Histone deacetylase 1
CHEMBL325
 IC50 4.42 4.42 38000.0 2
Histone deacetylase 4
CHEMBL3524
 IC50 4.36 4.36 44000.0 2
Histone deacetylase
CHEMBL2093865
 IC50 4.27 4.27 54000.0 1
Histone deacetylase 3
CHEMBL1829
 IC50 4.17 4.17 68000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase 8 IC50 = 44.0 nM 7.36 Inhibition of human His-thioredoxin-tagged HDAC8 expressed in Escherichia coli B... 30347148
Histone deacetylase 8 IC50 = 70.0 nM 7.16 Inhibition of HDAC8 by fluorometric assay 23116147
Histone deacetylase 8 IC50 = 70.0 nM 7.16 Inhibition of HDAC8 (unknown origin) assessed as release of fluorogenic AMC pre-... 37429084
Histone deacetylase 8 IC50 = 70.0 nM 7.16 Inhibition of human recombinant full length HDAC8 expressed in baculovirus infec... 37429084
Histone deacetylase 8 Kd = 81.7 nM 7.09 Binding affinity to Schistosoma mansoni His-tagged HDAC8 expressed in Escherichi... 30347148
Histone deacetylase 8 Kd = 89.6 nM 7.05 Binding affinity to human His-thioredoxin-tagged HDAC8 expressed in Escherichia ... 30347148
Histone deacetylase 8 IC50 = 95.4 nM 7.02 Inhibition of Schistosoma mansoni His-tagged HDAC8 expressed in Escherichia coli... 30347148
Unchecked IC50 = 274.0 nM 6.56 Inhibition of human His-thioredoxin-tagged HDAC8 mL1/mL6 mutant expressed in Esc... 30347148
Unchecked IC50 = 283.0 nM 6.55 Inhibition of human His-thioredoxin-tagged HDAC8 mL6 mutant expressed in Escheri... 30347148
Histone deacetylase 8 IC50 = 628.0 nM 6.2 Inhibition of human His-thioredoxin-tagged HDAC8 mL1/mL6/L179I mutant expressed ... 30347148
Histone deacetylase 8 IC50 = 746.0 nM 6.13 Inhibition of human His-thioredoxin-tagged HDAC8 mL6/L179I mutant expressed in E... 30347148
Histone deacetylase 6 IC50 = 2400.0 nM 5.62 Inhibition of HDAC6 by fluorometric assay 23116147
Unchecked IC50 = 2400.0 nM 5.62 Inhibition of HDAC6 (unknown origin) assessed as release of fluorogenic AMC pre-... 37429084
Histone deacetylase 1 IC50 = 38000.0 nM 4.42 Inhibition of HDAC1 by fluorometric assay 23116147
Histone deacetylase 1 IC50 = 38000.0 nM 4.42 Inhibition of HDAC1 (unknown origin) using Ac-Leu-Gly-Lys(Ac)-AMC as substrate p... 37429084
Histone deacetylase 4 IC50 = 44000.0 nM 4.36 Inhibition of HDAC4 by fluorometric assay 23116147
Histone deacetylase 4 IC50 = 44000.0 nM 4.36 Inhibition of HDAC4 (unknown origin) assessed as release of fluorogenic AMC pre-... 37429084
Histone deacetylase IC50 = 54000.0 nM 4.27 Inhibition of HDAC in human HeLa cells nuclear extracts by fluorometric assay 23116147
Histone deacetylase 3 IC50 = 68000.0 nM 4.17 Inhibition of HDAC3 (unknown origin) 31050421

Literature References

PubMed DOI Target Context # Activities
30347148 10.1021/acs.jmedchem.8b01087 Histone deacetylase 8 12
30347148 10.1021/acs.jmedchem.8b01087 Unchecked 6
30347148 10.1021/acs.jmedchem.8b01087 Schistosoma mansoni 4
23116147 10.1021/jm300837y Histone deacetylase 3
23116147 10.1021/jm300837y Histone deacetylase 8 3
37429084 10.1016/j.ejmech.2023.115594 Histone deacetylase 8 2
23116147 10.1021/jm300837y PBMC 2
23116147 10.1021/jm300837y MT2 1
23116147 10.1021/jm300837y HH 1
23116147 10.1021/jm300837y Jurkat 1
23116147 10.1021/jm300837y Histone deacetylase 6 1
23116147 10.1021/jm300837y Histone deacetylase 4 1
23116147 10.1021/jm300837y Histone deacetylase 2 1
23116147 10.1021/jm300837y Histone deacetylase 1 1
23116147 10.1021/jm300837y MT4 1
23116147 10.1021/jm300837y NB1 1
23116147 10.1021/jm300837y NON-PROTEIN TARGET 1
31050421 10.1021/acs.jmedchem.9b00359 Histone deacetylase 3 1
37429084 10.1016/j.ejmech.2023.115594 Histone deacetylase 1 1
37429084 10.1016/j.ejmech.2023.115594 Histone deacetylase 2 1

Data from ChEMBL 36 via Core Engine