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Compound Detail

CHEMBL1830424

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CCCCCCc1nc2cc(/C=C/C(=O)NO)ccc2n1CCN(C)C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1830424
Phase Preclinical
Structure Type MOL
InChI Key PUFPSZILMLJFEU-ZRDIBKRKSA-N
19
Targets
20
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

358.5
MW (Da)
3.24
ALogP
5
HBA
2
HBD
70.4
PSA (Ų)
0.30
QED
0
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C20H30N4O2
MW 358.49
Aromatic Rings 2
Heavy Atoms 26
NP-Likeness -0.97

Activity Summary

Ki 11 meas. best 8.28
IC50 9 meas. best 7.55

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase 4
CHEMBL3524
 Ki 8.28 8.28 5.3 1
Histone deacetylase 5
CHEMBL2563
 Ki 8.04 8.04 9.2 1
Histone deacetylase 11
CHEMBL3310
 Ki 7.96 7.96 11.0 1
Histone deacetylase 9
CHEMBL4145
 Ki 7.96 7.96 11.0 1
Polyamine deacetylase HDAC10
CHEMBL5103
 Ki 7.89 7.89 13.0 1
Histone deacetylase 1
CHEMBL325
 Ki 7.72 7.72 19.0 1
Histone deacetylase 3
CHEMBL1829
 Ki 7.7 7.7 20.0 1
Histone deacetylase 2
CHEMBL1937
 Ki 7.68 7.68 21.0 1
Histone deacetylase 1
CHEMBL325
 IC50 7.55 7.55 28.0 1
Histone deacetylase 7
CHEMBL2716
 Ki 7.16 7.16 70.0 1
Histone deacetylase 8
CHEMBL3192
 Ki 6.87 6.87 136.0 1
A2780
CHEMBL614004
 IC50 6.64 6.64 230.0 1
PC-3
CHEMBL390
 IC50 6.6 6.6 250.0 1
Histone deacetylase 6
CHEMBL1865
 Ki 6.52 6.52 300.0 1
COLO 205
CHEMBL614561
 IC50 6.48 6.48 330.0 1
HCT-116
CHEMBL394
 IC50 6.48 6.48 330.0 1
Cytochrome P450 3A4
CHEMBL340
 IC50 6.48 6.48 330.0 1
Cytochrome P450 2D6
CHEMBL289
 IC50 5.5 5.5 3170.0 1
Cytochrome P450 2C19
CHEMBL3622
 IC50 4.99 4.99 10300.0 1
Cytochrome P450 2C9
CHEMBL3397
 IC50 4.98 4.98 10400.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase 4 Ki = 5.3 nM 8.28 Competitive inhibition of HDAC4 using KI-104 as substrate by fluorescence assay 21634430
Histone deacetylase 5 Ki = 9.2 nM 8.04 Competitive inhibition of HDAC5 using KI-104 as substrate by fluorescence assay 21634430
Histone deacetylase 11 Ki = 11.0 nM 7.96 Competitive inhibition of HDAC11 using KI-104 as substrate by fluorescence assay 21634430
Histone deacetylase 9 Ki = 11.0 nM 7.96 Competitive inhibition of HDAC9 using KI-104 as substrate by fluorescence assay 21634430
Polyamine deacetylase HDAC10 Ki = 13.0 nM 7.89 Competitive inhibition of HDAC10 using KI-104 as substrate by fluorescence assay 21634430
Histone deacetylase 1 Ki = 19.0 nM 7.72 Competitive inhibition of HDAC1 using KI-104 as substrate by fluorescence assay 21634430
Histone deacetylase 3 Ki = 20.0 nM 7.7 Competitive inhibition of HDAC3 using KI-104 as substrate by fluorescence assay 21634430
Histone deacetylase 2 Ki = 21.0 nM 7.68 Competitive inhibition of HDAC2 using KI-104 as substrate by fluorescence assay 21634430
Histone deacetylase 1 IC50 = 28.0 nM 7.55 Inhibition of full length recombinant HDAC1 using Fluor de Lys as substrate by f... 21634430
Histone deacetylase 7 Ki = 70.0 nM 7.16 Competitive inhibition of HDAC7 using KI-104 as substrate by fluorescence assay 21634430
Histone deacetylase 8 Ki = 136.0 nM 6.87 Competitive inhibition of HDAC8 using KI-104 as substrate by fluorescence assay 21634430
A2780 IC50 = 230.0 nM 6.64 Antiproliferative activity against human A2780 cells after 96 hrs by celltiter 9... 21634430
PC-3 IC50 = 250.0 nM 6.6 Antiproliferative activity against human PC3 cells after 96 hrs by celltiter 96 ... 21634430
Histone deacetylase 6 Ki = 300.0 nM 6.52 Competitive inhibition of HDAC6 using KI-104 as substrate by fluorescence assay 21634430
Cytochrome P450 3A4 IC50 = 330.0 nM 6.48 Inhibition of recombinant CYP3A4 after 30 mins by fluorescence assay 21634430
HCT-116 IC50 = 330.0 nM 6.48 Antiproliferative activity against human HCT116 cells after 96 hrs by celltiter ... 21634430
COLO 205 IC50 = 330.0 nM 6.48 Antiproliferative activity against human COLO205 cells after 96 hrs by celltiter... 21634430
Cytochrome P450 2D6 IC50 = 3170.0 nM 5.5 Inhibition of recombinant CYP2D6 after 30 mins by fluorescence assay 21634430
Cytochrome P450 2C19 IC50 = 10300.0 nM 4.99 Inhibition of CYP2C19 in human liver microsomes by fluorescence assay 21634430
Cytochrome P450 2C9 IC50 = 10400.0 nM 4.98 Inhibition of CYP2C9 in human liver microsomes by fluorescence assay 21634430

Literature References

PubMed DOI Target Context # Activities
21634430 10.1021/jm2003552 Mus musculus 3
21634430 10.1021/jm2003552 Cytochrome P450 2D6 2
21634430 10.1021/jm2003552 Cytochrome P450 3A4 2
21634430 10.1021/jm2003552 Histone deacetylase 1 2
21634430 10.1021/jm2003552 Histone deacetylase 7 1
21634430 10.1021/jm2003552 Cytochrome P450 2C19 1
21634430 10.1021/jm2003552 Cytochrome P450 2C9 1
21634430 10.1021/jm2003552 Cytochrome P450 1A 1
21634430 10.1021/jm2003552 Histone deacetylase 11 1
21634430 10.1021/jm2003552 Polyamine deacetylase HDAC10 1
21634430 10.1021/jm2003552 Histone deacetylase 9 1
21634430 10.1021/jm2003552 Histone deacetylase 8 1
21634430 10.1021/jm2003552 Histone deacetylase 6 1
21634430 10.1021/jm2003552 Histone deacetylase 5 1
21634430 10.1021/jm2003552 Histone deacetylase 4 1
21634430 10.1021/jm2003552 Histone deacetylase 3 1
21634430 10.1021/jm2003552 Histone deacetylase 2 1
21634430 10.1021/jm2003552 PC-3 1
21634430 10.1021/jm2003552 HCT-116 1
21634430 10.1021/jm2003552 A2780 1

Data from ChEMBL 36 via Core Engine