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Compound Detail

CHEMBL2312168

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Cc1cc(C)cc(C(=O)NOCCCCCC(=O)NO)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2312168
Phase Preclinical
Structure Type MOL
InChI Key VRYZCEONIWEUAV-UHFFFAOYSA-N
15
Targets
36
Activities
2
Assay Types
0
PK Parameters
20
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 -0.61

Activity Summary

IC50 33 meas. best 8.38
Ki 3 meas. best 7.3

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase 5
CHEMBL2563
 IC50 8.38 8.38 4.2 1
Histone deacetylase 6
CHEMBL1865
 IC50 7.92 7.585 12.0 2
Histone deacetylase 4
CHEMBL3524
 IC50 7.92 7.92 11.9 1
Histone deacetylase 6
CHEMBL1865
 Ki 7.3 7.3 50.0 1
Histone deacetylase 1
CHEMBL325
 IC50 7.24 6.87 58.0 2
Histone deacetylase 2
CHEMBL1937
 Ki 7.1 7.1 80.0 1
Plasmodium falciparum
CHEMBL364
 IC50 7.0 6.74 100.0 2
Plasmodium berghei
CHEMBL612653
 IC50 6.8 6.8 160.0 1
Histone deacetylase
CHEMBL2093865
 IC50 6.77 6.379 170.0 10
A2780
CHEMBL614004
 IC50 6.5 6.2733 320.0 3
CAL-27
CHEMBL1075408
 IC50 6.12 5.95 760.0 3
Histone deacetylase 11
CHEMBL3310
 IC50 6.07 6.07 852.0 1
Histone deacetylase 2
CHEMBL1937
 IC50 6.05 6.05 881.0 1
HepG2
CHEMBL395
 IC50 5.9 5.9 1260.0 1
Histone deacetylase 8
CHEMBL3192
 IC50 5.89 5.89 1278.0 1
MDA-MB-231
CHEMBL400
 IC50 5.86 5.82 1370.0 2
KYSE-510
CHEMBL613868
 IC50 5.61 5.57 2480.0 2
Histone deacetylase 8
CHEMBL3192
 Ki 5.32 5.32 4810.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase 5 IC50 = 4.22 nM 8.38 Inhibition of human HDAC5 by fluorescence assay 23252603
Histone deacetylase 4 IC50 = 11.9 nM 7.92 Inhibition of human HDAC4 by fluorescence assay 23252603
Histone deacetylase 6 IC50 = 12.0 nM 7.92 Inhibition of HDAC6 (unknown origin) using Boc-Lys(Ac)-pNA as substrate preincub... 32551649
Histone deacetylase 6 Ki = 50.0 nM 7.3 Inhibition of recombinant human HDAC6 31787463
Histone deacetylase 6 IC50 = 55.7 nM 7.25 Inhibition of human HDAC6 by fluorescence assay 23252603
Histone deacetylase 1 IC50 = 58.0 nM 7.24 Inhibition of HDAC1 (unknown origin) using Boc-Lys(Ac)-pNA as substrate preincub... 32551649
Histone deacetylase 2 Ki = 80.0 nM 7.1 Inhibition of recombinant human HDAC2 31787463
Plasmodium falciparum IC50 = 100.0 nM 7.0 Antimalarial activity against asexual blood stage of Plasmodium falciparum 3D7 i... 24904967
Plasmodium berghei IC50 = 160.0 nM 6.8 Antimalarial activity against exo-erythrocytic form of Plasmodium berghei infect... 24904967
Histone deacetylase IC50 = 170.0 nM 6.77 Inhibition of HDAC in human A2780 cells 31787463
Histone deacetylase 1 IC50 = 320.0 nM 6.5 Inhibition of human HDAC1 by fluorescence assay 23252603
Histone deacetylase IC50 = 320.0 nM 6.5 Inhibition of HDAC in cisplatin resistant human A2780 cells after 18 hrs by fluo... 23252603
A2780 IC50 = 320.0 nM 6.5 Cytotoxicity against cisplatin resistant human A2780 cells after 72 hrs by MTT a... 23252603
Plasmodium falciparum IC50 = 330.0 nM 6.48 Antimalarial activity against late stage gametocyte stage of Plasmodium falcipar... 24904967
Histone deacetylase IC50 = 350.0 nM 6.46 Inhibition of HDAC in cisplatin resistant human KYSE-510 cells after 18 hrs by f... 23252603
Histone deacetylase IC50 = 360.0 nM 6.44 Inhibition of HDAC in cisplatin sensitive human CAL27 cells after 18 hrs by fluo... 23252603
Histone deacetylase IC50 = 360.0 nM 6.44 Inhibition of HDAC in cisplatin resistant human CAL27 cells after 18 hrs by fluo... 23252603
Histone deacetylase IC50 = 410.0 nM 6.39 Inhibition of HDAC in cisplatin resistant human MDA-MB-231 cells after 18 hrs by... 23252603
Histone deacetylase IC50 = 460.0 nM 6.34 Inhibition of HDAC in cisplatin sensitive human MDA-MB-231 cells after 18 hrs by... 23252603
A2780 IC50 = 490.0 nM 6.31 Cytotoxicity against human A2780 cells after 72 hrs by MTT assay 23252603

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL5724801 HEK-293T 320
- 10.6019/CHEMBL5724801 Fibroblast 320
- 10.6019/CHEMBL5724801 U2OS 320
23252603 10.1021/jm301254q KYSE-510 46
23252603 10.1021/jm301254q CAL-27 46
23252603 10.1021/jm301254q MDA-MB-231 46
23252603 10.1021/jm301254q A2780 46
- 10.6019/CHEMBL5674860 Colon cancer organoid 12
- 10.6019/CHEMBL5724558 Colon cancer organoid 12
- 10.6019/CHEMBL5058564 U2OS 10
23252603 10.1021/jm301254q Histone deacetylase 8
- 10.6019/CHEMBL5303304 Fibroblast 8
- 10.6019/CHEMBL5058564 HEK-293T 7
- 10.6019/CHEMBL5303304 U2OS 7
24904967 10.1016/j.ejmech.2014.05.050 Unchecked 7
- 10.6019/CHEMBL5303304 HEK-293T 7
- 10.6019/CHEMBL5608141 Colon cancer organoid 6
- 10.1158/2159-8290.CD-23-0050 Colon cancer organoid 5
- 10.6019/CHEMBL5058564 Fibroblast 4
31787463 10.1016/j.bmc.2019.115108 CAL-27 4

Data from ChEMBL 36 via Core Engine