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Compound Detail

CHEMBL556532

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O=C(/C=C/c1ccc(-c2ccccc2)cc1)NO
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL556532
Phase Preclinical
Structure Type MOL
InChI Key YMXJQEHWXZULBO-DHZHZOJOSA-N
6
Targets
17
Activities
1
Assay Types
2
PK Parameters
20
Publications
0
Known Names

Molecular Properties

239.3
MW (Da)
2.87
ALogP
2
HBA
2
HBD
49.3
PSA (Ų)
0.49
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C15H13NO2
MW 239.27
Aromatic Rings 2
Heavy Atoms 18
NP-Likeness -0.05

Activity Summary

IC50 17 meas. best 6.09

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase 2
CHEMBL1937
 IC50 6.09 6.09 820.0 3
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 6.05 5.472 900.0 5
NB-4
CHEMBL614188
 IC50 6.05 6.05 900.0 1
HCT-116
CHEMBL394
 IC50 5.8 5.8 1580.0 3
IGROV-1
CHEMBL613984
 IC50 5.46 5.445 3500.0 4
NCI-H460
CHEMBL396
 IC50 5.27 5.27 5400.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 6.0 hr Rattus norvegicus
T1/2 6.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase 2 IC50 = 820.0 nM 6.09 Inhibition of HDAC2 in human HeLa cells using KI-104 as substrate after 40 mins ... 24742384
Histone deacetylase 2 IC50 = 820.0 nM 6.09 Inhibition of human HDAC2 after 40 mins by fluorescence analysis 26376355
Histone deacetylase 2 IC50 = 820.0 nM 6.09 Inhibition of HDAC2 in human HeLa cells 19084294
NB-4 IC50 = 900.0 nM 6.05 Antiproliferative activity against human NB4 cells after 72 hrs 19084294
NON-PROTEIN TARGET IC50 = 900.0 nM 6.05 Growth inhibition of human NB4 cells after 72 hrs 26376355
HCT-116 IC50 = 1580.0 nM 5.8 Antiproliferative activity against human HCT116 cells after 72 hrs 19084294
HCT-116 IC50 = 1580.0 nM 5.8 Antiproliferative activity against human HCT116 cells assessed as growth inhibit... 24742384
HCT-116 IC50 = 1600.0 nM 5.8 Growth inhibition of human HCT116 cells after 72 hrs 26376355
IGROV-1 IC50 = 3500.0 nM 5.46 Antiproliferative activity against human IGROV1 cells after 72 hrs 19084294
IGROV-1 IC50 = 3500.0 nM 5.46 Growth inhibition of human IGROV1 cells after 72 hrs 26376355
IGROV-1 IC50 = 3500.0 nM 5.46 Antiproliferative activity against human IGROV1 cells assessed as growth inhibit... 24742384
IGROV-1 IC50 = 4000.0 nM 5.4 Antiproliferative activity against cisplatin-resistant human IGROV1 cells after ... 19084294
NON-PROTEIN TARGET IC50 = 4000.0 nM 5.4 Growth inhibition of human IGROV1/Pt1 cells after 72 hrs 26376355
NON-PROTEIN TARGET IC50 = 4300.0 nM 5.37 Antiproliferative activity against p53 defective cis-platinum-resistant human IG... 24742384
NCI-H460 IC50 = 5400.0 nM 5.27 Antiproliferative activity against human H460 cells after 72 hrs 19084294
NON-PROTEIN TARGET IC50 = 5400.0 nM 5.27 Antiproliferative activity against human H460 cells assessed as growth inhibitio... 24742384
NON-PROTEIN TARGET IC50 = 5400.0 nM 5.27 Growth inhibition of human H460 cells after 72 hrs 26376355

Literature References

PubMed DOI Target Context # Activities
26376355 10.1016/j.bmcl.2015.09.006 NON-PROTEIN TARGET 3
35307568 10.1016/j.bmcl.2022.128692 Mycobacterium tuberculosis 2
19084294 10.1016/j.ejmech.2008.11.005 IGROV-1 2
35307568 10.1016/j.bmcl.2022.128692 Mycobacterium marinum 2
19084294 10.1016/j.ejmech.2008.11.005 Mus musculus 2
35307568 10.1016/j.bmcl.2022.128692 Mycobacteroides abscessus 2
24742384 10.1016/j.ejmech.2014.04.021 NON-PROTEIN TARGET 2
28985084 10.1021/acs.jmedchem.7b01444 Plasma 2
26376355 10.1016/j.bmcl.2015.09.006 Histone deacetylase 2 1
35307568 10.1016/j.bmcl.2022.128692 BMDM 1
- 10.1039/C6MD00477F T98G 1
- 10.1039/C6MD00477F LN-18 1
26376355 10.1016/j.bmcl.2015.09.006 HCT-116 1
26376355 10.1016/j.bmcl.2015.09.006 IGROV-1 1
19084294 10.1016/j.ejmech.2008.11.005 Histone deacetylase 2 1
24742384 10.1016/j.ejmech.2014.04.021 IGROV-1 1
24742384 10.1016/j.ejmech.2014.04.021 HCT-116 1
24742384 10.1016/j.ejmech.2014.04.021 Histone deacetylase 2 1
19084294 10.1016/j.ejmech.2008.11.005 NCI-H460 1
19084294 10.1016/j.ejmech.2008.11.005 HCT-116 1

Data from ChEMBL 36 via Core Engine