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Compound Detail

CHEMBL4248676

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O=C(CCc1ccc(Nc2c3ccccc3nc3ccccc23)cc1)NO
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4248676
Phase Preclinical
Structure Type MOL
InChI Key AGYUQCCMUDLPIU-UHFFFAOYSA-N
10
Targets
11
Activities
1
Assay Types
0
PK Parameters
13
Publications
0
Known Names

Molecular Properties

357.4
MW (Da)
4.57
ALogP
4
HBA
3
HBD
74.2
PSA (Ų)
0.28
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C22H19N3O2
MW 357.41
Aromatic Rings 4
Heavy Atoms 27
NP-Likeness -0.52

Activity Summary

IC50 11 meas. best 7.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase 6
CHEMBL1865
 IC50 7.0 6.925 99.3 2
Class 1 histone deacetylase
CHEMBL4523988
 IC50 7.0 7.0 100.0 1
Histone deacetylase 1
CHEMBL325
 IC50 6.87 6.87 133.8 1
U-937
CHEMBL612794
 IC50 6.12 6.12 750.0 1
HCT-116
CHEMBL394
 IC50 5.73 5.73 1880.0 1
Histone deacetylase 5
CHEMBL2563
 IC50 5.59 5.59 2580.0 1
Histone deacetylase 4
CHEMBL3524
 IC50 5.15 5.15 7060.0 1
MDA-MB-231
CHEMBL400
 IC50 4.54 4.54 29080.0 1
Histone deacetylase 9
CHEMBL4145
 IC50 4.54 4.54 28960.0 1
Histone deacetylase 7
CHEMBL2716
 IC50 4.5 4.5 31530.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase 6 IC50 = 99.3 nM 7.0 Inhibition of HDAC6 (unknown origin) using Ac-peptide as substrate pretreated fo... 29954683
Class 1 histone deacetylase IC50 = 100.0 nM 7.0 Inhibition of class 1 HDAC in human HeLa cell nuclear extract using Boc-Lys(Ac)-... 32151835
Histone deacetylase 1 IC50 = 133.8 nM 6.87 Inhibition of HDAC1 (unknown origin) using Ac-peptide as substrate pretreated fo... 29954683
Histone deacetylase 6 IC50 = 140.0 nM 6.85 Inhibition of recombinant human full-length N-terminal GST-tagged HDAC6 expresse... 32151835
U-937 IC50 = 750.0 nM 6.12 Antiproliferative activity against human U937 cells after 48 hrs by MTT assay 29954683
HCT-116 IC50 = 1880.0 nM 5.73 Antiproliferative activity against human HCT116 cells after 48 hrs by MTT assay 29954683
Histone deacetylase 5 IC50 = 2580.0 nM 5.59 Inhibition of recombinant human C-terminal His-tagged HDAC5 (656 to 1122 residue... 32151835
Histone deacetylase 4 IC50 = 7060.0 nM 5.15 Inhibition of recombinant human N-terminal GST-tagged/C-terminal His-tagged HDAC... 32151835
MDA-MB-231 IC50 = 29080.0 nM 4.54 Antiproliferative activity against human MDA-MB-231 cells after 48 hrs by MTT as... 29954683
Histone deacetylase 9 IC50 = 28960.0 nM 4.54 Inhibition of recombinant human C-terminal His-tagged HDAC9 (604 to 1066 residue... 32151835
Histone deacetylase 7 IC50 = 31530.0 nM 4.5 Inhibition of recombinant human N-terminal GST-tagged HDAC7 (518 to end residues... 32151835

Literature References

PubMed DOI Target Context # Activities
29954683 10.1016/j.bmc.2018.06.016 HCT-116 1
29954683 10.1016/j.bmc.2018.06.016 MDA-MB-231 1
29954683 10.1016/j.bmc.2018.06.016 U-937 1
29954683 10.1016/j.bmc.2018.06.016 DNA topoisomerase 2-alpha 1
29954683 10.1016/j.bmc.2018.06.016 DNA topoisomerase 1 1
29954683 10.1016/j.bmc.2018.06.016 Histone deacetylase 6 1
29954683 10.1016/j.bmc.2018.06.016 Histone deacetylase 1 1
32151835 10.1016/j.ejmech.2020.112193 Class 1 histone deacetylase 1
32151835 10.1016/j.ejmech.2020.112193 Histone deacetylase 7 1
32151835 10.1016/j.ejmech.2020.112193 Histone deacetylase 4 1
32151835 10.1016/j.ejmech.2020.112193 Histone deacetylase 5 1
32151835 10.1016/j.ejmech.2020.112193 Histone deacetylase 9 1
32151835 10.1016/j.ejmech.2020.112193 Histone deacetylase 6 1

Data from ChEMBL 36 via Core Engine