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Compound Detail

CHEMBL390452

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O=C(/C=C/c1cccc(C(=O)c2cc3ccccc3o2)c1)NO
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL390452
Phase Preclinical
Structure Type MOL
InChI Key KMVDSQMVUNRCNZ-CMDGGOBGSA-N
25
Targets
31
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

307.3
MW (Da)
3.18
ALogP
4
HBA
2
HBD
79.5
PSA (Ų)
0.34
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 C18H13NO4
MW 307.31
Aromatic Rings 3
Heavy Atoms 23
NP-Likeness -0.17

Activity Summary

IC50 30 meas. best 7.31
EC50 1 meas. best 6.54

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
EOL1
CHEMBL614489
 IC50 7.31 7.31 49.0 1
Histone deacetylase 1
CHEMBL325
 IC50 7.28 7.28 52.0 1
Histone deacetylase
CHEMBL2093865
 IC50 7.24 7.24 57.0 1
Histone deacetylase 3
CHEMBL1829
 IC50 7.1 7.1 79.0 1
Histone deacetylase 8
CHEMBL3192
 IC50 7.1 7.1 79.0 1
K562
CHEMBL385
 IC50 6.82 6.82 150.0 1
PC-3
CHEMBL390
 IC50 6.8 6.8 160.0 1
CCRF-CEM
CHEMBL382
 IC50 6.75 6.685 180.0 2
NCI
CHEMBL614877
 IC50 6.72 6.72 190.0 1
NCI-H460
CHEMBL396
 IC50 6.6 6.6 250.0 1
Histone deacetylase
CHEMBL2093865
 EC50 6.54 6.54 290.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 6.51 6.05 310.0 5
SK-BR-3
CHEMBL613834
 IC50 6.51 6.51 310.0 1
A2780
CHEMBL614004
 IC50 6.46 6.46 350.0 1
HCT-116
CHEMBL394
 IC50 6.44 6.44 360.0 1
MDA-MB-468
CHEMBL614335
 IC50 6.3 6.3 500.0 1
A-431
CHEMBL614069
 IC50 6.23 6.23 590.0 1
CAL-27
CHEMBL1075408
 IC50 6.18 6.18 660.0 1
HeLa
CHEMBL399
 IC50 6.17 6.17 680.0 1
MDA-MB-231
CHEMBL400
 IC50 6.14 6.14 730.0 1
HCT-15
CHEMBL612263
 IC50 6.13 6.13 740.0 1
SK-OV-3
CHEMBL614925
 IC50 6.13 6.13 740.0 1
A549
CHEMBL392
 IC50 6.11 6.11 770.0 1
SAOS-2
CHEMBL614894
 IC50 6.04 6.04 920.0 1
MCF7
CHEMBL387
 IC50 5.89 5.89 1300.0 1
ASPC1
CHEMBL612588
 IC50 5.46 5.46 3500.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
EOL1 IC50 = 49.0 nM 7.31 Cytotoxicity against human EOL1cells 17691763
Histone deacetylase 1 IC50 = 52.0 nM 7.28 Inhibition of recombinant HDAC1 in HeLa cells 17691763
Histone deacetylase IC50 = 57.0 nM 7.24 Inhibition of HDAC in HeLa cells 17691763
Histone deacetylase 3 IC50 = 79.0 nM 7.1 Inhibition of recombinant HDAC3 17691763
Histone deacetylase 8 IC50 = 79.0 nM 7.1 Inhibition of recombinant HDAC8 17691763
K562 IC50 = 150.0 nM 6.82 Cytotoxicity against human K562 cells 17691763
PC-3 IC50 = 160.0 nM 6.8 Cytotoxicity against human PC3 cells 17691763
CCRF-CEM IC50 = 180.0 nM 6.75 Cytotoxicity against human CCRF-CEM cells 17691763
NCI IC50 = 190.0 nM 6.72 Cytotoxicity against human NCI H69 cells 17691763
CCRF-CEM IC50 = 240.0 nM 6.62 Cytotoxicity against vincristine resistant human CCRF-CEM cells 17691763
NCI-H460 IC50 = 250.0 nM 6.6 Cytotoxicity against human NCI H460 cells 17691763
Histone deacetylase EC50 = 290.0 nM 6.54 Inhibition of HDAC in HeLa cells assessed as induction of human histone H3 hyper... 17691763
SK-BR-3 IC50 = 310.0 nM 6.51 Cytotoxicity against human SKBR3 cells 17691763
NON-PROTEIN TARGET IC50 = 310.0 nM 6.51 Cytotoxicity against human WM 266-4 cells 17691763
A2780 IC50 = 350.0 nM 6.46 Cytotoxicity against human A2780 cells 17691763
HCT-116 IC50 = 360.0 nM 6.44 Cytotoxicity against human HCT116 cells 17691763
NON-PROTEIN TARGET IC50 = 470.0 nM 6.33 Cytotoxicity against human Hec-1-A cells 17691763
MDA-MB-468 IC50 = 500.0 nM 6.3 Cytotoxicity against human MDA-MB-468 cells 17691763
A-431 IC50 = 590.0 nM 6.23 Cytotoxicity against human A431 cells 17691763
CAL-27 IC50 = 660.0 nM 6.18 Cytotoxicity against human Cal27 cells 17691763

Literature References

PubMed DOI Target Context # Activities
17691763 10.1021/jm0703136 NON-PROTEIN TARGET 5
17691763 10.1021/jm0703136 A549 3
17691763 10.1021/jm0703136 CCRF-CEM 2
17691763 10.1021/jm0703136 Unchecked 2
17691763 10.1021/jm0703136 Histone deacetylase 2
17691763 10.1021/jm0703136 MDA-MB-231 1
17691763 10.1021/jm0703136 SAOS-2 1
17691763 10.1021/jm0703136 A-431 1
17691763 10.1021/jm0703136 Histone deacetylase 8 1
17691763 10.1021/jm0703136 PC-3 1
17691763 10.1021/jm0703136 HCT-116 1
17691763 10.1021/jm0703136 HCT-15 1
17691763 10.1021/jm0703136 A2780 1
17691763 10.1021/jm0703136 SK-OV-3 1
17691763 10.1021/jm0703136 SK-BR-3 1
17691763 10.1021/jm0703136 NCI 1
17691763 10.1021/jm0703136 NCI-H460 1
17691763 10.1021/jm0703136 Histone deacetylase 1 1
17691763 10.1021/jm0703136 CAL-27 1
17691763 10.1021/jm0703136 MCF7 1

Data from ChEMBL 36 via Core Engine