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Compound Detail

CHEMBL1830420

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CCCCCCc1nc2cc(/C=C/C(=O)NO)ccc2n1CCNCC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1830420
Phase Preclinical
Structure Type MOL
InChI Key QEULZLVHLYBHJN-ZRDIBKRKSA-N
15
Targets
16
Activities
2
Assay Types
1
PK Parameters
18
Publications
0
Known Names

Molecular Properties

358.5
MW (Da)
3.29
ALogP
5
HBA
3
HBD
79.2
PSA (Ų)
0.25
QED
0
Ro5 Violations
11
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 -0.82

Activity Summary

Ki 11 meas. best 8.21
IC50 5 meas. best 7.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase 4
CHEMBL3524
 Ki 8.21 8.21 6.2 1
Histone deacetylase 5
CHEMBL2563
 Ki 8.17 8.17 6.8 1
Histone deacetylase 1
CHEMBL325
 Ki 7.96 7.96 11.0 1
Histone deacetylase 3
CHEMBL1829
 Ki 7.89 7.89 13.0 1
Histone deacetylase 11
CHEMBL3310
 Ki 7.89 7.89 13.0 1
Histone deacetylase 9
CHEMBL4145
 Ki 7.85 7.85 14.0 1
Histone deacetylase 2
CHEMBL1937
 Ki 7.75 7.75 18.0 1
Histone deacetylase 1
CHEMBL325
 IC50 7.7 7.7 20.0 1
Polyamine deacetylase HDAC10
CHEMBL5103
 Ki 7.55 7.55 28.0 1
Histone deacetylase 7
CHEMBL2716
 Ki 7.46 7.46 35.0 1
Histone deacetylase 8
CHEMBL3192
 Ki 7.27 7.27 54.0 1
COLO 205
CHEMBL614561
 IC50 6.72 6.72 190.0 1
PC-3
CHEMBL390
 IC50 6.68 6.68 210.0 1
HCT-116
CHEMBL394
 IC50 6.64 6.64 230.0 1
A2780
CHEMBL614004
 IC50 6.62 6.62 240.0 1
Histone deacetylase 6
CHEMBL1865
 Ki 6.55 6.55 282.0 1

Pharmacokinetic Data

Parameter Value Units Species
F 1.4 % Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase 4 Ki = 6.2 nM 8.21 Competitive inhibition of HDAC4 using KI-104 as substrate by fluorescence assay 21634430
Histone deacetylase 5 Ki = 6.8 nM 8.17 Competitive inhibition of HDAC5 using KI-104 as substrate by fluorescence assay 21634430
Histone deacetylase 1 Ki = 11.0 nM 7.96 Competitive inhibition of HDAC1 using KI-104 as substrate by fluorescence assay 21634430
Histone deacetylase 3 Ki = 13.0 nM 7.89 Competitive inhibition of HDAC3 using KI-104 as substrate by fluorescence assay 21634430
Histone deacetylase 11 Ki = 13.0 nM 7.89 Competitive inhibition of HDAC11 using KI-104 as substrate by fluorescence assay 21634430
Histone deacetylase 9 Ki = 14.0 nM 7.85 Competitive inhibition of HDAC9 using KI-104 as substrate by fluorescence assay 21634430
Histone deacetylase 2 Ki = 18.0 nM 7.75 Competitive inhibition of HDAC2 using KI-104 as substrate by fluorescence assay 21634430
Histone deacetylase 1 IC50 = 20.0 nM 7.7 Inhibition of full length recombinant HDAC1 using Fluor de Lys as substrate by f... 21634430
Polyamine deacetylase HDAC10 Ki = 28.0 nM 7.55 Competitive inhibition of HDAC10 using KI-104 as substrate by fluorescence assay 21634430
Histone deacetylase 7 Ki = 35.0 nM 7.46 Competitive inhibition of HDAC7 using KI-104 as substrate by fluorescence assay 21634430
Histone deacetylase 8 Ki = 54.0 nM 7.27 Competitive inhibition of HDAC8 using KI-104 as substrate by fluorescence assay 21634430
COLO 205 IC50 = 190.0 nM 6.72 Antiproliferative activity against human COLO205 cells after 96 hrs by celltiter... 21634430
PC-3 IC50 = 210.0 nM 6.68 Antiproliferative activity against human PC3 cells after 96 hrs by celltiter 96 ... 21634430
HCT-116 IC50 = 230.0 nM 6.64 Antiproliferative activity against human HCT116 cells after 96 hrs by celltiter ... 21634430
A2780 IC50 = 240.0 nM 6.62 Antiproliferative activity against human A2780 cells after 96 hrs by celltiter 9... 21634430
Histone deacetylase 6 Ki = 282.0 nM 6.55 Competitive inhibition of HDAC6 using KI-104 as substrate by fluorescence assay 21634430

Literature References

PubMed DOI Target Context # Activities
21634430 10.1021/jm2003552 Histone deacetylase 1 2
21634430 10.1021/jm2003552 Histone deacetylase 6 1
21634430 10.1021/jm2003552 Mus musculus 1
21634430 10.1021/jm2003552 Rattus norvegicus 1
21634430 10.1021/jm2003552 Caco-2 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 7 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
21634430 10.1021/jm2003552 COLO 205 1

Data from ChEMBL 36 via Core Engine