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Compound Detail

CHEMBL242533

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O=C(/C=C/c1cccc(C(=O)c2cc3ccccc3[nH]2)c1)NO
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL242533
Phase Preclinical
Structure Type MOL
InChI Key YONXIFHNDNWCKF-CMDGGOBGSA-N
25
Targets
31
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

306.3
MW (Da)
2.92
ALogP
3
HBA
3
HBD
82.2
PSA (Ų)
0.30
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 C18H14N2O3
MW 306.32
Aromatic Rings 3
Heavy Atoms 23
NP-Likeness -0.18

Activity Summary

IC50 30 meas. best 7.51
EC50 1 meas. best 5.89

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase 1
CHEMBL325
 IC50 7.51 7.51 31.0 1
Histone deacetylase 8
CHEMBL3192
 IC50 7.5 7.5 32.0 1
Histone deacetylase
CHEMBL2093865
 IC50 7.41 7.41 39.0 1
Histone deacetylase 3
CHEMBL1829
 IC50 7.3 7.3 50.0 1
EOL1
CHEMBL614489
 IC50 7.14 7.14 73.0 1
K562
CHEMBL385
 IC50 6.77 6.77 170.0 1
CCRF-CEM
CHEMBL382
 IC50 6.7 6.65 200.0 2
PC-3
CHEMBL390
 IC50 6.68 6.68 210.0 1
NCI-H460
CHEMBL396
 IC50 6.58 6.58 260.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 6.51 6.058 310.0 5
NCI
CHEMBL614877
 IC50 6.48 6.48 330.0 1
A2780
CHEMBL614004
 IC50 6.47 6.47 340.0 1
HCT-116
CHEMBL394
 IC50 6.44 6.44 360.0 1
SK-BR-3
CHEMBL613834
 IC50 6.28 6.28 530.0 1
MDA-MB-468
CHEMBL614335
 IC50 6.26 6.26 550.0 1
A-431
CHEMBL614069
 IC50 6.22 6.22 600.0 1
CAL-27
CHEMBL1075408
 IC50 6.12 6.12 750.0 1
HCT-15
CHEMBL612263
 IC50 6.11 6.11 770.0 1
HeLa
CHEMBL399
 IC50 6.07 6.07 850.0 1
MDA-MB-231
CHEMBL400
 IC50 6.05 6.05 900.0 1
SK-OV-3
CHEMBL614925
 IC50 6.05 6.05 900.0 1
A549
CHEMBL392
 IC50 6.01 6.01 970.0 1
SAOS-2
CHEMBL614894
 IC50 6.0 6.0 1000.0 1
Histone deacetylase
CHEMBL2093865
 EC50 5.89 5.89 1300.0 1
MCF7
CHEMBL387
 IC50 5.72 5.72 1900.0 1
ASPC1
CHEMBL612588
 IC50 5.41 5.41 3900.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase 1 IC50 = 31.0 nM 7.51 Inhibition of recombinant HDAC1 in HeLa cells 17691763
Histone deacetylase 8 IC50 = 32.0 nM 7.5 Inhibition of recombinant HDAC8 17691763
Histone deacetylase IC50 = 39.0 nM 7.41 Inhibition of HDAC in HeLa cells 17691763
Histone deacetylase 3 IC50 = 50.0 nM 7.3 Inhibition of recombinant HDAC3 17691763
EOL1 IC50 = 73.0 nM 7.14 Cytotoxicity against human EOL1cells 17691763
K562 IC50 = 170.0 nM 6.77 Cytotoxicity against human K562 cells 17691763
CCRF-CEM IC50 = 200.0 nM 6.7 Cytotoxicity against human CCRF-CEM cells 17691763
PC-3 IC50 = 210.0 nM 6.68 Cytotoxicity against human PC3 cells 17691763
CCRF-CEM IC50 = 250.0 nM 6.6 Cytotoxicity against vincristine resistant human CCRF-CEM cells 17691763
NCI-H460 IC50 = 260.0 nM 6.58 Cytotoxicity against human NCI H460 cells 17691763
NON-PROTEIN TARGET IC50 = 310.0 nM 6.51 Cytotoxicity against human WM 266-4 cells 17691763
NCI IC50 = 330.0 nM 6.48 Cytotoxicity against human NCI H69 cells 17691763
A2780 IC50 = 340.0 nM 6.47 Cytotoxicity against human A2780 cells 17691763
HCT-116 IC50 = 360.0 nM 6.44 Cytotoxicity against human HCT116 cells 17691763
SK-BR-3 IC50 = 530.0 nM 6.28 Cytotoxicity against human SKBR3 cells 17691763
MDA-MB-468 IC50 = 550.0 nM 6.26 Cytotoxicity against human MDA-MB-468 cells 17691763
A-431 IC50 = 600.0 nM 6.22 Cytotoxicity against human A431 cells 17691763
NON-PROTEIN TARGET IC50 = 620.0 nM 6.21 Cytotoxicity against human Hec-1-A cells 17691763
CAL-27 IC50 = 750.0 nM 6.12 Cytotoxicity against human Cal27 cells 17691763
HCT-15 IC50 = 770.0 nM 6.11 Cytotoxicity against human HCT15 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 PC-3 1
17691763 10.1021/jm0703136 EOL1 1
17691763 10.1021/jm0703136 HeLa 1
17691763 10.1021/jm0703136 Histone deacetylase 1 1
17691763 10.1021/jm0703136 NCI-H460 1
17691763 10.1021/jm0703136 HCT-116 1
17691763 10.1021/jm0703136 NCI 1
17691763 10.1021/jm0703136 MCF7 1
17691763 10.1021/jm0703136 MDA-MB-468 1
17691763 10.1021/jm0703136 MDA-MB-231 1
17691763 10.1021/jm0703136 SK-BR-3 1
17691763 10.1021/jm0703136 SK-OV-3 1
17691763 10.1021/jm0703136 A2780 1
17691763 10.1021/jm0703136 HCT-15 1
17691763 10.1021/jm0703136 Histone deacetylase 3 1

Data from ChEMBL 36 via Core Engine