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Compound Detail

CHEMBL556332

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O=C(/C=C/c1ccc(-c2ccc(O)cc2)cc1)NO
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL556332
Phase Preclinical
Structure Type MOL
InChI Key MGGQEULGVBEMAL-XCVCLJGOSA-N
16
Targets
22
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

255.3
MW (Da)
2.58
ALogP
3
HBA
3
HBD
69.6
PSA (Ų)
0.45
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 C15H13NO3
MW 255.27
Aromatic Rings 2
Heavy Atoms 19
NP-Likeness 0.28

Activity Summary

IC50 22 meas. best 7.38

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase 6
CHEMBL1865
 IC50 7.38 7.38 41.8 1
Histone deacetylase 8
CHEMBL3192
 IC50 6.79 6.51 162.0 2
HCT-116
CHEMBL394
 IC50 6.48 6.48 330.0 2
Histone deacetylase 2
CHEMBL1937
 IC50 6.23 6.23 590.0 2
NB-4
CHEMBL614188
 IC50 5.64 5.64 2300.0 1
Histone deacetylase 3
CHEMBL1829
 IC50 5.34 5.34 4570.0 1
Histone deacetylase 11
CHEMBL3310
 IC50 5.3 5.3 5010.0 1
Histone deacetylase 1
CHEMBL325
 IC50 5.26 5.26 5510.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.22 5.205 6000.0 2
NCI-H460
CHEMBL396
 IC50 5.22 5.22 6000.0 1
IGROV-1
CHEMBL613984
 IC50 5.19 5.1433 6500.0 3
Histone deacetylase 9
CHEMBL4145
 IC50 5.05 5.05 8920.0 1
Polyamine deacetylase HDAC10
CHEMBL5103
 IC50 4.96 4.96 11000.0 1
Histone deacetylase 5
CHEMBL2563
 IC50 4.95 4.95 11200.0 1
Histone deacetylase 7
CHEMBL2716
 IC50 4.81 4.81 15600.0 1
Histone deacetylase 4
CHEMBL3524
 IC50 4.77 4.77 17100.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase 6 IC50 = 41.8 nM 7.38 Inhibition of human HDAC6 using fluorogenic tetrapeptide RHKKAc as substrate 24742384
Histone deacetylase 8 IC50 = 162.0 nM 6.79 Inhibition of human HDAC8 using fluorogenic tetrapeptide RHKKAc as substrate 24742384
HCT-116 IC50 = 330.0 nM 6.48 Antiproliferative activity against human HCT116 cells after 72 hrs 19084294
HCT-116 IC50 = 330.0 nM 6.48 Antiproliferative activity against human HCT116 cells assessed as growth inhibit... 24742384
Histone deacetylase 2 IC50 = 590.0 nM 6.23 Inhibition of HDAC2 in human HeLa cells 19084294
Histone deacetylase 8 IC50 = 590.0 nM 6.23 Inhibition of Homo sapiens (human) HDAC8 -
Histone deacetylase 2 IC50 = 590.0 nM 6.23 Inhibition of HDAC2 in human HeLa cells using KI-104 as substrate after 40 mins ... 24742384
NB-4 IC50 = 2300.0 nM 5.64 Antiproliferative activity against human NB4 cells after 72 hrs 19084294
Histone deacetylase 3 IC50 = 4570.0 nM 5.34 Inhibition of human HDAC3 complexed with NCOR2 using fluorogenic tetrapeptide RH... 24742384
Histone deacetylase 11 IC50 = 5010.0 nM 5.3 Inhibition of human HDAC11 using fluorogenic tetrapeptide RHKKAc as substrate 24742384
Histone deacetylase 1 IC50 = 5510.0 nM 5.26 Inhibition of human HDAC1 using fluorogenic tetrapeptide RHKKAc as substrate 24742384
NCI-H460 IC50 = 6000.0 nM 5.22 Antiproliferative activity against human H460 cells after 72 hrs 19084294
NON-PROTEIN TARGET IC50 = 6000.0 nM 5.22 Antiproliferative activity against human H460 cells assessed as growth inhibitio... 24742384
IGROV-1 IC50 = 6500.0 nM 5.19 Antiproliferative activity against cisplatin-resistant human IGROV1 cells after ... 19084294
NON-PROTEIN TARGET IC50 = 6500.0 nM 5.19 Antiproliferative activity against p53 defective cis-platinum-resistant human IG... 24742384
IGROV-1 IC50 = 7600.0 nM 5.12 Antiproliferative activity against human IGROV1 cells after 72 hrs 19084294
IGROV-1 IC50 = 7600.0 nM 5.12 Antiproliferative activity against human IGROV1 cells assessed as growth inhibit... 24742384
Histone deacetylase 9 IC50 = 8920.0 nM 5.05 Inhibition of human HDAC9 using fluorogenic tetrapeptide RHKKAc as substrate 24742384
Polyamine deacetylase HDAC10 IC50 = 11000.0 nM 4.96 Inhibition of human HDAC10 using fluorogenic tetrapeptide RHKKAc as substrate 24742384
Histone deacetylase 5 IC50 = 11200.0 nM 4.95 Inhibition of human HDAC5 using fluorogenic tetrapeptide RHKKAc as substrate 24742384

Literature References

PubMed DOI Target Context # Activities
19084294 10.1016/j.ejmech.2008.11.005 IGROV-1 6
19084294 10.1016/j.ejmech.2008.11.005 Histone deacetylase 6
19084294 10.1016/j.ejmech.2008.11.005 Histone deacetylase 6 6
19084294 10.1016/j.ejmech.2008.11.005 Mus musculus 5
24742384 10.1016/j.ejmech.2014.04.021 NON-PROTEIN TARGET 2
19084294 10.1016/j.ejmech.2008.11.005 HCT-116 2
24742384 10.1016/j.ejmech.2014.04.021 Histone deacetylase 2 1
24742384 10.1016/j.ejmech.2014.04.021 Histone deacetylase 9 1
24742384 10.1016/j.ejmech.2014.04.021 Histone deacetylase 11 1
24742384 10.1016/j.ejmech.2014.04.021 Histone deacetylase 3 1
24742384 10.1016/j.ejmech.2014.04.021 Histone deacetylase 6 1
24742384 10.1016/j.ejmech.2014.04.021 Histone deacetylase 4 1
24742384 10.1016/j.ejmech.2014.04.021 Histone deacetylase 8 1
24742384 10.1016/j.ejmech.2014.04.021 Histone deacetylase 7 1
24742384 10.1016/j.ejmech.2014.04.021 Histone deacetylase 5 1
24742384 10.1016/j.ejmech.2014.04.021 Polyamine deacetylase HDAC10 1
24742384 10.1016/j.ejmech.2014.04.021 HCT-116 1
- 10.1007/s00044-011-9571-y Histone deacetylase 8 1
19084294 10.1016/j.ejmech.2008.11.005 NCI-H460 1
19084294 10.1016/j.ejmech.2008.11.005 NB-4 1

Data from ChEMBL 36 via Core Engine