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Compound Detail

CHEMBL5191350

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C#CCN(C)CCCOc1cc(NCc2ccc(/C=C/C(=O)NO)cc2)ccc1Cl
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL5191350
Phase Preclinical
Structure Type MOL
InChI Key JWIRZQYHZOIRPQ-FMIVXFBMSA-N
8
Targets
9
Activities
2
Assay Types
0
PK Parameters
9
Publications
0
Known Names

Molecular Properties

427.9
MW (Da)
3.80
ALogP
5
HBA
3
HBD
73.8
PSA (Ų)
0.17
QED
0
Ro5 Violations
11
Rot. Bonds

Drug Information

Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C23H26ClN3O3
MW 427.93
Aromatic Rings 2
Heavy Atoms 30
NP-Likeness -1.11

Activity Summary

IC50 8 meas. best 8.4
EC50 1 meas. best 5.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Amine oxidase [flavin-containing] A
CHEMBL1951
 IC50 8.4 8.4 4.0 1
Histone deacetylase 8
CHEMBL3192
 IC50 7.1 7.1 80.0 1
Histone deacetylase 6
CHEMBL1865
 IC50 7.0 7.0 100.0 1
Unchecked
CHEMBL612545
 IC50 6.92 6.92 120.0 1
Histone deacetylase 1
CHEMBL325
 IC50 6.29 6.29 510.0 1
U-251
CHEMBL615022
 IC50 6.0 5.745 990.0 2
Histone deacetylase 2
CHEMBL1937
 IC50 5.94 5.94 1160.0 1
Lysine-specific histone demethylase 1A
CHEMBL6136
 EC50 5.0 5.0 10000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Amine oxidase [flavin-containing] A IC50 = 4.0 nM 8.4 Inhibition of MAO-A (unknown origin) expressed in mouse GL26 cells using 14C 5-h... 35005974
Histone deacetylase 8 IC50 = 80.0 nM 7.1 Inhibition of human HDAC8 (379 to 382 residues) using RHKKAcKAc-AMC fluorogenic ... 35005974
Histone deacetylase 6 IC50 = 100.0 nM 7.0 Inhibition of human HDAC6 (379 to 382 residues) using RHKKAc fluorogenic peptide... 35005974
Unchecked IC50 = 120.0 nM 6.92 Cytotoxicity against mouse GL26 cells assessed as inhibition of cell growth incu... 35005974
Histone deacetylase 1 IC50 = 510.0 nM 6.29 Inhibition of human HDAC1 (379 to 382 residues) using RHKKAc-AMC fluorogenic pep... 35005974
U-251 IC50 = 990.0 nM 6.0 Cytotoxicity against human TMZ-resistant U251 cells assessed as inhibition of ce... 35005974
Histone deacetylase 2 IC50 = 1160.0 nM 5.94 Inhibition of human HDAC2 (379 to 382 residues) using RHKKAc-AMC fluorogenic pep... 35005974
U-251 IC50 = 3240.0 nM 5.49 Cytotoxicity against human TMZ-sensitive U251 cells assessed as inhibition of ce... 35005974
Lysine-specific histone demethylase 1A EC50 = 10000.0 nM 5.0 Inhibition of human LSD1 assessed as demethylase activity of LSD1 using Histone ... 35005974

Literature References

PubMed DOI Target Context # Activities
35005974 10.1021/acs.jmedchem.1c01726 Unchecked 7
35005974 10.1021/acs.jmedchem.1c01726 ADMET 6
35005974 10.1021/acs.jmedchem.1c01726 U-251 3
35005974 10.1021/acs.jmedchem.1c01726 Amine oxidase [flavin-containing] A 1
35005974 10.1021/acs.jmedchem.1c01726 Histone deacetylase 1 1
35005974 10.1021/acs.jmedchem.1c01726 Histone deacetylase 2 1
35005974 10.1021/acs.jmedchem.1c01726 Histone deacetylase 6 1
35005974 10.1021/acs.jmedchem.1c01726 Histone deacetylase 8 1
35005974 10.1021/acs.jmedchem.1c01726 Lysine-specific histone demethylase 1A 1

Data from ChEMBL 36 via Core Engine