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Compound Detail

CHEMBL552465

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O=C(/C=C/c1ccc(NC(=O)Nc2ccc(Cl)cc2)cc1)NO
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL552465
Phase Preclinical
Structure Type MOL
InChI Key BPQUKDOJAFTDQI-XCVCLJGOSA-N
7
Targets
12
Activities
1
Assay Types
0
PK Parameters
10
Publications
0
Known Names

Molecular Properties

331.8
MW (Da)
3.50
ALogP
3
HBA
4
HBD
90.5
PSA (Ų)
0.39
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C16H14ClN3O3
MW 331.76
Aromatic Rings 2
Heavy Atoms 23
NP-Likeness -0.80

Activity Summary

IC50 12 meas. best 8.09

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase 6
CHEMBL1865
 IC50 8.09 8.09 8.1 1
Jurkat
CHEMBL397
 IC50 7.4 6.4 40.0 3
NAMALVA
CHEMBL614049
 IC50 6.7 6.7 200.0 1
Histone deacetylase 8
CHEMBL3192
 IC50 6.08 6.08 840.0 1
Histone deacetylase 1
CHEMBL325
 IC50 6.08 5.785 840.0 2
Unchecked
CHEMBL612545
 IC50 6.08 5.9767 831.8 3
HCT-116
CHEMBL394
 IC50 4.53 4.53 29860.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase 6 IC50 = 8.1 nM 8.09 Inhibition of recombinant human full-length N-terminal GST-tagged HDAC6 (1 to 12... 33668008
Jurkat IC50 = 40.0 nM 7.4 Cytotoxicity against human Jurkat cells assessed as reduction in cell viability ... 33668008
NAMALVA IC50 = 200.0 nM 6.7 Cytotoxicity against human NAMALVA cells assessed as reduction in cell viability... 33668008
Jurkat IC50 = 600.0 nM 6.22 Cytotoxicity against human Jurkat cells assessed as reduction in cell viability ... 33668008
Unchecked IC50 = 840.0 nM 6.08 Inhibition of HDAC 19136179
Unchecked IC50 = 831.76 nM 6.08 Inhibition of HDAC 19136179
Histone deacetylase 8 IC50 = 840.0 nM 6.08 Inhibition of Homo sapiens (human) HDAC8 -
Histone deacetylase 1 IC50 = 840.0 nM 6.08 Inhibition of Histone Deacetylase Enzymatic Assay: For deacetylase assays, 20,00... -
Unchecked IC50 = 1700.0 nM 5.77 Cytotoxicity against human HS5 cells assessed as reduction in cell viability mea... 33668008
Jurkat IC50 = 2600.0 nM 5.58 Cytotoxicity against human Jurkat cells assessed as reduction in cell viability ... 33668008
Histone deacetylase 1 IC50 = 3260.0 nM 5.49 Inhibition of recombinant human full-length C-terminal FLAG/His-tagged HDAC1 (1 ... 33668008
HCT-116 IC50 = 29860.0 nM 4.53 Cytotoxicity against human HCT-116 cells assessed as reduction in cell viability... 33668008

Literature References

PubMed DOI Target Context # Activities
33668008 10.1016/j.bmc.2021.116085 Jurkat 13
33668008 10.1016/j.bmc.2021.116085 Unchecked 10
33668008 10.1016/j.bmc.2021.116085 NAMALVA 9
33668008 10.1016/j.bmc.2021.116085 Histone deacetylase 6 3
33668008 10.1016/j.bmc.2021.116085 Histone deacetylase 3
19136179 10.1016/j.ejmech.2008.12.008 Unchecked 2
- 10.1007/s00044-011-9571-y Histone deacetylase 8 1
33668008 10.1016/j.bmc.2021.116085 HCT-116 1
33668008 10.1016/j.bmc.2021.116085 MCF7 1
33668008 10.1016/j.bmc.2021.116085 Histone deacetylase 1 1

Data from ChEMBL 36 via Core Engine