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Compound Detail

CHEMBL561209

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COc1ccc(-c2ccc(/C=C/C(=O)NO)cc2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL561209
Phase Preclinical
Structure Type MOL
InChI Key WKQPXLKFQLGQSM-NYYWCZLTSA-N
16
Targets
27
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

269.3
MW (Da)
2.88
ALogP
3
HBA
2
HBD
58.6
PSA (Ų)
0.51
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 C16H15NO3
MW 269.30
Aromatic Rings 2
Heavy Atoms 20
NP-Likeness -0.02

Activity Summary

IC50 27 meas. best 7.43

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase 6
CHEMBL1865
 IC50 7.43 7.43 36.8 1
Histone deacetylase 8
CHEMBL3192
 IC50 7.16 7.16 69.8 1
HCT-116
CHEMBL394
 IC50 6.66 6.66 220.0 2
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 6.58 5.84 260.0 5
IGROV-1
CHEMBL613984
 IC50 6.12 5.96 750.0 3
Histone deacetylase 2
CHEMBL1937
 IC50 5.94 5.94 1160.0 2
HT-29
CHEMBL384
 IC50 5.8 5.78 1580.0 2
NCI-H460
CHEMBL396
 IC50 5.43 5.43 3700.0 1
Histone deacetylase 1
CHEMBL325
 IC50 5.07 5.07 8550.0 1
Histone deacetylase
CHEMBL2093865
 IC50 5.06 4.775 8700.0 2
Histone deacetylase 5
CHEMBL2563
 IC50 4.53 4.53 29600.0 1
Histone deacetylase 9
CHEMBL4145
 IC50 4.41 4.41 39300.0 1
Histone deacetylase 11
CHEMBL3310
 IC50 4.14 4.14 73000.0 1
Histone deacetylase 3
CHEMBL1829
 IC50 4.07 4.07 84500.0 1
Polyamine deacetylase HDAC10
CHEMBL5103
 IC50 4.04 4.04 91000.0 1
Histone deacetylase 4
CHEMBL3524
 IC50 4.0 4.0 99400.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase 6 IC50 = 36.8 nM 7.43 Inhibition of human HDAC6 using fluorogenic tetrapeptide RHKKAc as substrate 24742384
Histone deacetylase 8 IC50 = 69.8 nM 7.16 Inhibition of human HDAC8 using fluorogenic tetrapeptide RHKKAc as substrate 24742384
HCT-116 IC50 = 220.0 nM 6.66 Antiproliferative activity against human HCT116 cells after 72 hrs 19084294
HCT-116 IC50 = 220.0 nM 6.66 Antiproliferative activity against human HCT116 cells assessed as growth inhibit... 24742384
NON-PROTEIN TARGET IC50 = 260.0 nM 6.58 Antiproliferative activity human HCT116 cells assessed as reduction in cell numb... 26890116
IGROV-1 IC50 = 750.0 nM 6.12 Antiproliferative activity against human IGROV1 cells after 72 hrs 19084294
IGROV-1 IC50 = 750.0 nM 6.12 Antiproliferative activity against human IGROV1 cells assessed as growth inhibit... 24742384
NON-PROTEIN TARGET IC50 = 750.0 nM 6.12 Antiproliferative activity against human IGROV1 cells assessed as reduction in c... 26890116
Histone deacetylase 2 IC50 = 1160.0 nM 5.94 Inhibition of HDAC2 in human HeLa cells 19084294
Histone deacetylase 2 IC50 = 1160.0 nM 5.94 Inhibition of HDAC2 in human HeLa cells using KI-104 as substrate after 40 mins ... 24742384
HT-29 IC50 = 1580.0 nM 5.8 Antiproliferative activity against human HT-29 cells assessed as reduction in ce... 26890116
HT-29 IC50 = 1730.0 nM 5.76 Antiproliferative activity against mitoxantrone resistant human HT-29 cells asse... 26890116
NON-PROTEIN TARGET IC50 = 2300.0 nM 5.64 Antiproliferative activity against p53 defective cis-platinum-resistant human IG... 24742384
IGROV-1 IC50 = 2300.0 nM 5.64 Antiproliferative activity against cisplatin-resistant human IGROV1 cells after ... 19084294
NCI-H460 IC50 = 3700.0 nM 5.43 Antiproliferative activity against human H460 cells after 72 hrs 19084294
NON-PROTEIN TARGET IC50 = 3700.0 nM 5.43 Antiproliferative activity against human H460 cells assessed as growth inhibitio... 24742384
NON-PROTEIN TARGET IC50 = 3700.0 nM 5.43 Antiproliferative activity against human H460 cells assessed as reduction in cel... 26890116
Histone deacetylase 1 IC50 = 8550.0 nM 5.07 Inhibition of human HDAC1 using fluorogenic tetrapeptide RHKKAc as substrate 24742384
Histone deacetylase IC50 = 8700.0 nM 5.06 Inhibition of HDAC in human HeLa cells using BOC-Ac-Lys-AMC as substrate incubat... 26890116
Histone deacetylase 5 IC50 = 29600.0 nM 4.53 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 8
19084294 10.1016/j.ejmech.2008.11.005 Mus musculus 7
19084294 10.1016/j.ejmech.2008.11.005 Histone deacetylase 6
19084294 10.1016/j.ejmech.2008.11.005 Histone deacetylase 6 6
26890116 10.1016/j.ejmech.2016.02.001 NON-PROTEIN TARGET 4
24742384 10.1016/j.ejmech.2014.04.021 IGROV-1 4
19084294 10.1016/j.ejmech.2008.11.005 HCT-116 3
19084294 10.1016/j.ejmech.2008.11.005 NCI-H460 3
26890116 10.1016/j.ejmech.2016.02.001 Histone deacetylase 2
26890116 10.1016/j.ejmech.2016.02.001 HT-29 2
24742384 10.1016/j.ejmech.2014.04.021 Histone deacetylase 6 2
24742384 10.1016/j.ejmech.2014.04.021 NON-PROTEIN TARGET 2
24742384 10.1016/j.ejmech.2014.04.021 Histone deacetylase 7 1
24742384 10.1016/j.ejmech.2014.04.021 Molecular identity unknown 1
24742384 10.1016/j.ejmech.2014.04.021 Histone deacetylase 5 1
24742384 10.1016/j.ejmech.2014.04.021 Histone deacetylase 2 1
24742384 10.1016/j.ejmech.2014.04.021 HCT-116 1
24742384 10.1016/j.ejmech.2014.04.021 Histone deacetylase 8 1
24742384 10.1016/j.ejmech.2014.04.021 Histone deacetylase 11 1
19084294 10.1016/j.ejmech.2008.11.005 NB-4 1

Data from ChEMBL 36 via Core Engine