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Compound Detail

CHEMBL2312167

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Cc1ccc(C(=O)NOCCCCCC(=O)NO)cc1C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2312167
Phase Preclinical
Structure Type MOL
InChI Key XBQPEXDCROFSOE-UHFFFAOYSA-N
15
Targets
27
Activities
1
Assay Types
0
PK Parameters
16
Publications
0
Known Names

Molecular Properties

294.4
MW (Da)
2.03
ALogP
4
HBA
3
HBD
87.7
PSA (Ų)
0.39
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C15H22N2O4
MW 294.35
Aromatic Rings 1
Heavy Atoms 21
NP-Likeness -0.81

Activity Summary

IC50 27 meas. best 7.74

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase 6
CHEMBL1865
 IC50 7.74 7.74 18.1 1
Histone deacetylase 5
CHEMBL2563
 IC50 7.48 7.48 33.4 1
Histone deacetylase 4
CHEMBL3524
 IC50 7.08 7.08 82.6 1
Plasmodium falciparum
CHEMBL364
 IC50 6.92 6.76 120.0 2
Plasmodium berghei
CHEMBL612653
 IC50 6.51 6.51 310.0 1
Histone deacetylase 1
CHEMBL325
 IC50 6.5 6.5 320.0 1
Histone deacetylase 8
CHEMBL3192
 IC50 6.08 6.08 833.0 1
Histone deacetylase
CHEMBL2093865
 IC50 6.06 5.8675 880.0 8
Histone deacetylase 2
CHEMBL1937
 IC50 6.03 6.03 944.0 1
Histone deacetylase 11
CHEMBL3310
 IC50 6.0 6.0 997.0 1
A2780
CHEMBL614004
 IC50 5.81 5.78 1540.0 2
MDA-MB-231
CHEMBL400
 IC50 5.56 5.49 2770.0 2
CAL-27
CHEMBL1075408
 IC50 5.54 5.455 2900.0 2
HepG2
CHEMBL395
 IC50 5.49 5.49 3240.0 1
KYSE-510
CHEMBL613868
 IC50 5.02 5.01 9460.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase 6 IC50 = 18.1 nM 7.74 Inhibition of human HDAC6 by fluorescence assay 23252603
Histone deacetylase 5 IC50 = 33.4 nM 7.48 Inhibition of human HDAC5 by fluorescence assay 23252603
Histone deacetylase 4 IC50 = 82.6 nM 7.08 Inhibition of human HDAC4 by fluorescence assay 23252603
Plasmodium falciparum IC50 = 120.0 nM 6.92 Antimalarial activity against asexual blood stage of Plasmodium falciparum 3D7 i... 24904967
Plasmodium falciparum IC50 = 250.0 nM 6.6 Antimalarial activity against late stage gametocyte stage of Plasmodium falcipar... 24904967
Plasmodium berghei IC50 = 310.0 nM 6.51 Antimalarial activity against exo-erythrocytic form of Plasmodium berghei infect... 24904967
Histone deacetylase 1 IC50 = 320.0 nM 6.5 Inhibition of human HDAC1 by fluorescence assay 23252603
Histone deacetylase 8 IC50 = 833.0 nM 6.08 Inhibition of human HDAC8 by fluorescence assay 23252603
Histone deacetylase IC50 = 880.0 nM 6.06 Inhibition of HDAC in cisplatin resistant human A2780 cells after 18 hrs by fluo... 23252603
Histone deacetylase IC50 = 910.0 nM 6.04 Inhibition of HDAC in cisplatin resistant human CAL27 cells after 18 hrs by fluo... 23252603
Histone deacetylase 2 IC50 = 944.0 nM 6.03 Inhibition of human HDAC2 by fluorescence assay 23252603
Histone deacetylase 11 IC50 = 997.0 nM 6.0 Inhibition of human HDAC11 by fluorescence assay 23252603
Histone deacetylase IC50 = 1100.0 nM 5.96 Inhibition of HDAC in cisplatin sensitive human CAL27 cells after 18 hrs by fluo... 23252603
Histone deacetylase IC50 = 1100.0 nM 5.96 Inhibition of HDAC in cisplatin resistant human KYSE-510 cells after 18 hrs by f... 23252603
A2780 IC50 = 1540.0 nM 5.81 Cytotoxicity against human A2780 cells after 72 hrs by MTT assay 23252603
Histone deacetylase IC50 = 1570.0 nM 5.8 Inhibition of HDAC in cisplatin sensitive human MDA-MB-231 cells after 18 hrs by... 23252603
Histone deacetylase IC50 = 1610.0 nM 5.79 Inhibition of HDAC in human A2780 cells after 18 hrs by fluorescence assay 23252603
Histone deacetylase IC50 = 1660.0 nM 5.78 Inhibition of HDAC in cisplatin resistant human MDA-MB-231 cells after 18 hrs by... 23252603
A2780 IC50 = 1780.0 nM 5.75 Cytotoxicity against cisplatin resistant human A2780 cells after 72 hrs by MTT a... 23252603
MDA-MB-231 IC50 = 2770.0 nM 5.56 Cytotoxicity against cisplatin sensitive human MDA-MB-231 cells after 72 hrs by ... 23252603

Literature References

PubMed DOI Target Context # Activities
23252603 10.1021/jm301254q Histone deacetylase 8
24904967 10.1016/j.ejmech.2014.05.050 Unchecked 7
23252603 10.1021/jm301254q KYSE-510 2
23252603 10.1021/jm301254q CAL-27 2
23252603 10.1021/jm301254q MDA-MB-231 2
23252603 10.1021/jm301254q A2780 2
24904967 10.1016/j.ejmech.2014.05.050 Plasmodium falciparum 2
23252603 10.1021/jm301254q Histone deacetylase 11 1
23252603 10.1021/jm301254q Histone deacetylase 8 1
23252603 10.1021/jm301254q Histone deacetylase 6 1
23252603 10.1021/jm301254q Histone deacetylase 5 1
23252603 10.1021/jm301254q Histone deacetylase 4 1
23252603 10.1021/jm301254q Histone deacetylase 2 1
23252603 10.1021/jm301254q Histone deacetylase 1 1
24904967 10.1016/j.ejmech.2014.05.050 HepG2 1
24904967 10.1016/j.ejmech.2014.05.050 Plasmodium berghei 1

Data from ChEMBL 36 via Core Engine