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Compound Detail

CHEMBL2312164

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Cc1cccc(C(=O)NOCCCCCC(=O)NO)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2312164
Phase Preclinical
Structure Type MOL
InChI Key BAKKPDUWEXRTIN-UHFFFAOYSA-N
15
Targets
27
Activities
1
Assay Types
0
PK Parameters
17
Publications
0
Known Names

Molecular Properties

280.3
MW (Da)
1.72
ALogP
4
HBA
3
HBD
87.7
PSA (Ų)
0.38
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 C14H20N2O4
MW 280.32
Aromatic Rings 1
Heavy Atoms 20
NP-Likeness -0.85

Activity Summary

IC50 27 meas. best 8.64

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase 5
CHEMBL2563
 IC50 8.64 8.64 2.3 1
Histone deacetylase 4
CHEMBL3524
 IC50 7.79 7.79 16.3 1
Histone deacetylase 6
CHEMBL1865
 IC50 7.57 7.57 26.9 1
Plasmodium falciparum
CHEMBL364
 IC50 6.72 6.545 190.0 2
Histone deacetylase 1
CHEMBL325
 IC50 6.47 6.47 341.0 1
Plasmodium berghei
CHEMBL612653
 IC50 6.18 6.18 660.0 1
Histone deacetylase
CHEMBL2093865
 IC50 6.06 5.8975 880.0 8
Histone deacetylase 8
CHEMBL3192
 IC50 5.98 5.98 1043.0 1
Histone deacetylase 2
CHEMBL1937
 IC50 5.86 5.86 1392.0 1
A2780
CHEMBL614004
 IC50 5.68 5.665 2100.0 2
Histone deacetylase 11
CHEMBL3310
 IC50 5.67 5.67 2135.0 1
MDA-MB-231
CHEMBL400
 IC50 5.55 5.485 2790.0 2
CAL-27
CHEMBL1075408
 IC50 5.53 5.48 2970.0 2
HepG2
CHEMBL395
 IC50 5.33 5.33 4690.0 1
KYSE-510
CHEMBL613868
 IC50 5.09 5.09 8190.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase 5 IC50 = 2.31 nM 8.64 Inhibition of human HDAC5 by fluorescence assay 23252603
Histone deacetylase 4 IC50 = 16.3 nM 7.79 Inhibition of human HDAC4 by fluorescence assay 23252603
Histone deacetylase 6 IC50 = 26.9 nM 7.57 Inhibition of human HDAC6 by fluorescence assay 23252603
Plasmodium falciparum IC50 = 190.0 nM 6.72 Antimalarial activity against asexual blood stage of Plasmodium falciparum 3D7 i... 24904967
Histone deacetylase 1 IC50 = 341.0 nM 6.47 Inhibition of human HDAC1 by fluorescence assay 23252603
Plasmodium falciparum IC50 = 430.0 nM 6.37 Antimalarial activity against late stage gametocyte stage of Plasmodium falcipar... 24904967
Plasmodium berghei IC50 = 660.0 nM 6.18 Antimalarial activity against exo-erythrocytic form of Plasmodium berghei infect... 24904967
Histone deacetylase IC50 = 880.0 nM 6.06 Inhibition of HDAC in cisplatin resistant human CAL27 cells after 18 hrs by fluo... 23252603
Histone deacetylase IC50 = 900.0 nM 6.05 Inhibition of HDAC in cisplatin resistant human A2780 cells after 18 hrs by fluo... 23252603
Histone deacetylase IC50 = 1000.0 nM 6.0 Inhibition of HDAC in cisplatin sensitive human CAL27 cells after 18 hrs by fluo... 23252603
Histone deacetylase 8 IC50 = 1043.0 nM 5.98 Inhibition of human HDAC8 by fluorescence assay 23252603
Histone deacetylase IC50 = 1130.0 nM 5.95 Inhibition of HDAC in cisplatin resistant human KYSE-510 cells after 18 hrs by f... 23252603
Histone deacetylase IC50 = 1280.0 nM 5.89 Inhibition of HDAC in cisplatin resistant human MDA-MB-231 cells after 18 hrs by... 23252603
Histone deacetylase 2 IC50 = 1392.0 nM 5.86 Inhibition of human HDAC2 by fluorescence assay 23252603
Histone deacetylase IC50 = 1410.0 nM 5.85 Inhibition of HDAC in cisplatin sensitive human MDA-MB-231 cells after 18 hrs by... 23252603
Histone deacetylase IC50 = 1580.0 nM 5.8 Inhibition of HDAC in human A2780 cells after 18 hrs by fluorescence assay 23252603
A2780 IC50 = 2100.0 nM 5.68 Cytotoxicity against human A2780 cells after 72 hrs by MTT assay 23252603
Histone deacetylase 11 IC50 = 2135.0 nM 5.67 Inhibition of human HDAC11 by fluorescence assay 23252603
A2780 IC50 = 2250.0 nM 5.65 Cytotoxicity against cisplatin resistant human A2780 cells after 72 hrs by MTT a... 23252603
Histone deacetylase IC50 = 2620.0 nM 5.58 Inhibition of HDAC in cisplatin sensitive human KYSE-510 cells after 18 hrs by f... 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
24904967 10.1016/j.ejmech.2014.05.050 Plasmodium falciparum 2
23252603 10.1021/jm301254q A2780 2
23252603 10.1021/jm301254q MDA-MB-231 2
23252603 10.1021/jm301254q CAL-27 2
23252603 10.1021/jm301254q KYSE-510 2
24904967 10.1016/j.ejmech.2014.05.050 Plasmodium berghei 1
23252603 10.1021/jm301254q Unchecked 1
24904967 10.1016/j.ejmech.2014.05.050 HepG2 1
23252603 10.1021/jm301254q Histone deacetylase 1 1
23252603 10.1021/jm301254q Histone deacetylase 2 1
23252603 10.1021/jm301254q Histone deacetylase 4 1
23252603 10.1021/jm301254q Histone deacetylase 5 1
23252603 10.1021/jm301254q Histone deacetylase 6 1
23252603 10.1021/jm301254q Histone deacetylase 8 1
23252603 10.1021/jm301254q Histone deacetylase 11 1

Data from ChEMBL 36 via Core Engine