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Compound Detail

CHEMBL4574697

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O=C(/C=C/c1ccc(C(=O)NC(Cc2c[nH]c3ccccc23)C(=O)Nc2ccc(Cl)cc2)cc1)NO
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4574697
Phase Preclinical
Structure Type MOL
InChI Key MQWJSZLCUHDPRW-VGOFMYFVSA-N
12
Targets
12
Activities
1
Assay Types
0
PK Parameters
12
Publications
0
Known Names

Molecular Properties

503.0
MW (Da)
4.32
ALogP
4
HBA
5
HBD
123.3
PSA (Ų)
0.14
QED
1
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C27H23ClN4O4
MW 502.96
Aromatic Rings 4
Heavy Atoms 36
NP-Likeness -0.66

Activity Summary

IC50 12 meas. best 8.23

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase 1
CHEMBL325
 IC50 8.23 8.23 5.9 1
Histone deacetylase
CHEMBL2093865
 IC50 7.46 7.46 35.0 1
Histone deacetylase 8
CHEMBL3192
 IC50 6.61 6.61 243.1 1
Histone deacetylase 11
CHEMBL3310
 IC50 5.87 5.87 1365.0 1
PC-3
CHEMBL390
 IC50 5.71 5.71 1960.0 1
U-937
CHEMBL612794
 IC50 5.68 5.68 2110.0 1
Histone deacetylase 6
CHEMBL1865
 IC50 5.54 5.54 2863.0 1
HeLa
CHEMBL399
 IC50 5.48 5.48 3280.0 1
HT-29
CHEMBL384
 IC50 5.47 5.47 3400.0 1
HEL
CHEMBL613888
 IC50 5.47 5.47 3350.0 1
K562
CHEMBL385
 IC50 5.36 5.36 4350.0 1
Unchecked
CHEMBL612545
 IC50 5.27 5.27 5390.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase 1 IC50 = 5.929 nM 8.23 Inhibition of HDAC1 (unknown origin) using Ac-Leu-GlyLys(Ac)-AMC as substrate pr... 30879863
Histone deacetylase IC50 = 35.0 nM 7.46 Inhibition of HDAC in human HeLa nuclear extract using Boc-Lys(Ac)-AMC as substr... 30879863
Histone deacetylase 8 IC50 = 243.1 nM 6.61 Inhibition of HDAC8 (unknown origin) using Ac-Leu-GlyLys(Ac)-AMC as substrate pr... 30879863
Histone deacetylase 11 IC50 = 1365.0 nM 5.87 Inhibition of HDAC11 (unknown origin) using Ac-Leu-GlyLys(Ac)-AMC as substrate p... 30879863
PC-3 IC50 = 1960.0 nM 5.71 Antiproliferative activity against human PC3 cells after 48 hrs by MTT assay 30879863
U-937 IC50 = 2110.0 nM 5.68 Antiproliferative activity against human U937 cells after 48 hrs by MTT assay 30879863
Histone deacetylase 6 IC50 = 2863.0 nM 5.54 Inhibition of HDAC6 (unknown origin) using Ac-Leu-GlyLys(Ac)-AMC as substrate pr... 30879863
HeLa IC50 = 3280.0 nM 5.48 Antiproliferative activity against human HeLa cells after 48 hrs by MTT assay 30879863
HT-29 IC50 = 3400.0 nM 5.47 Antiproliferative activity against human HT-29 cells after 48 hrs by MTT assay 30879863
HEL IC50 = 3350.0 nM 5.47 Antiproliferative activity against human HEL cells after 48 hrs by MTT assay 30879863
K562 IC50 = 4350.0 nM 5.36 Antiproliferative activity against human K562 cells after 48 hrs by MTT assay 30879863
Unchecked IC50 = 5390.0 nM 5.27 Antiproliferative activity against human SK-N-BE(2) cells after 48 hrs by MTT as... 30879863

Literature References

PubMed DOI Target Context # Activities
30879863 10.1016/j.bmc.2019.03.008 HeLa 1
30879863 10.1016/j.bmc.2019.03.008 Histone deacetylase 1
30879863 10.1016/j.bmc.2019.03.008 Unchecked 1
30879863 10.1016/j.bmc.2019.03.008 PC-3 1
30879863 10.1016/j.bmc.2019.03.008 HT-29 1
30879863 10.1016/j.bmc.2019.03.008 K562 1
30879863 10.1016/j.bmc.2019.03.008 HEL 1
30879863 10.1016/j.bmc.2019.03.008 U-937 1
30879863 10.1016/j.bmc.2019.03.008 Histone deacetylase 1 1
30879863 10.1016/j.bmc.2019.03.008 Histone deacetylase 6 1
30879863 10.1016/j.bmc.2019.03.008 Histone deacetylase 8 1
30879863 10.1016/j.bmc.2019.03.008 Histone deacetylase 11 1

Data from ChEMBL 36 via Core Engine