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Compound Detail

CHEMBL3215861

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CCCCc1nc2cc(/C=C/C(=O)NO)ccc2n1CCN(CC)CC.Cl.Cl
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3215861
Phase Preclinical
Structure Type MOL
InChI Key CHLPUMOYKYJFFH-PFNYCKIMSA-N
Parent Compound CHEMBL1851943
Active Moiety CHEMBL1851943
19
Targets
21
Activities
2
Assay Types
25
PK Parameters
20
Publications
0
Known Names

Molecular Properties

358.5
MW (Da)
3.24
ALogP
5
HBA
2
HBD
70.4
PSA (Ų)
0.39
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 C20H32Cl2N4O2
MW 431.41
Aromatic Rings 2
Heavy Atoms 26
NP-Likeness -1.26

Activity Summary

Ki 11 meas. best 7.8
IC50 10 meas. best 7.11

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase 4
CHEMBL3524
 Ki 7.8 7.8 16.0 1
Histone deacetylase 3
CHEMBL1829
 Ki 7.72 7.72 19.0 1
Histone deacetylase 5
CHEMBL2563
 Ki 7.68 7.68 21.0 1
Polyamine deacetylase HDAC10
CHEMBL5103
 Ki 7.64 7.64 23.0 1
Histone deacetylase 11
CHEMBL3310
 Ki 7.62 7.62 24.0 1
Histone deacetylase 9
CHEMBL4145
 Ki 7.62 7.62 24.0 1
Histone deacetylase 2
CHEMBL1937
 Ki 7.57 7.57 27.0 1
Histone deacetylase 1
CHEMBL325
 Ki 7.55 7.55 28.0 1
Histone deacetylase 8
CHEMBL3192
 Ki 7.32 7.32 48.0 1
Histone deacetylase 1
CHEMBL325
 IC50 7.11 7.11 77.0 1
MV4-11
CHEMBL613835
 IC50 7.0 7.0 100.0 1
Histone deacetylase 7
CHEMBL2716
 Ki 6.98 6.98 104.0 1
Ramos
CHEMBL614629
 IC50 6.85 6.85 140.0 1
Histone deacetylase 6
CHEMBL1865
 Ki 6.61 6.61 247.0 1
PC-3
CHEMBL390
 IC50 6.47 6.47 340.0 2
HCT-116
CHEMBL394
 IC50 6.32 6.32 480.0 1
A2780
CHEMBL614004
 IC50 6.32 6.32 480.0 1
COLO 205
CHEMBL614561
 IC50 6.25 6.25 560.0 1
Cytochrome P450 3A4
CHEMBL340
 IC50 5.56 5.56 2730.0 1
Cytochrome P450 2C19
CHEMBL3622
 IC50 5.24 5.24 5780.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 903.39 ng.hr.mL-1 Mus musculus
AUC 1530.75 ng.hr.mL-1 Mus musculus
AUC 412.26 ng.hr.mL-1 Rattus norvegicus
AUC 64.89 ng.hr.mL-1 Rattus norvegicus
AUC 1154.34 ng.hr.mL-1 Canis lupus familiaris
AUC 3760.56 ng.hr.mL-1 Canis lupus familiaris
Cmax 6100.0 nM Mus musculus
Cmax 139.0 nM Rattus norvegicus
Cmax 3560.0 nM Canis lupus familiaris
F 3.1 % Rattus norvegicus
F 34.0 % Mus musculus
F 65.0 % Canis lupus familiaris
T1/2 1.0 hr Homo sapiens
T1/2 0.45 hr Mus musculus
T1/2 0.13 hr Rattus norvegicus
T1/2 1.0 hr Canis lupus familiaris
T1/2 2.26 hr Mus musculus
T1/2 2.44 hr Mus musculus
T1/2 0.89 hr Rattus norvegicus
T1/2 2.02 hr Rattus norvegicus
T1/2 3.9 hr Canis lupus familiaris
T1/2 4.12 hr Canis lupus familiaris
Tmax 0.17 hr Mus musculus
Tmax 0.24 hr Rattus norvegicus
Tmax 0.75 hr Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase 4 Ki = 16.0 nM 7.8 Competitive inhibition of HDAC4 using KI-104 as substrate by fluorescence assay 21634430
Histone deacetylase 3 Ki = 19.0 nM 7.72 Competitive inhibition of HDAC3 using KI-104 as substrate by fluorescence assay 21634430
Histone deacetylase 5 Ki = 21.0 nM 7.68 Competitive inhibition of HDAC5 using KI-104 as substrate by fluorescence assay 21634430
Polyamine deacetylase HDAC10 Ki = 23.0 nM 7.64 Competitive inhibition of HDAC10 using KI-104 as substrate by fluorescence assay 21634430
Histone deacetylase 11 Ki = 24.0 nM 7.62 Competitive inhibition of HDAC11 using KI-104 as substrate by fluorescence assay 21634430
Histone deacetylase 9 Ki = 24.0 nM 7.62 Competitive inhibition of HDAC9 using KI-104 as substrate by fluorescence assay 21634430
Histone deacetylase 2 Ki = 27.0 nM 7.57 Competitive inhibition of HDAC2 using KI-104 as substrate by fluorescence assay 21634430
Histone deacetylase 1 Ki = 28.0 nM 7.55 Competitive inhibition of HDAC1 using KI-104 as substrate by fluorescence assay 21634430
Histone deacetylase 8 Ki = 48.0 nM 7.32 Competitive inhibition of HDAC8 using KI-104 as substrate by fluorescence assay 21634430
Histone deacetylase 1 IC50 = 77.0 nM 7.11 Inhibition of full length recombinant HDAC1 using Fluor de Lys as substrate by f... 21634430
MV4-11 IC50 = 100.0 nM 7.0 Antiproliferative activity against human MV4-11 cells 21634430
Histone deacetylase 7 Ki = 104.0 nM 6.98 Competitive inhibition of HDAC7 using KI-104 as substrate by fluorescence assay 21634430
Ramos IC50 = 140.0 nM 6.85 Antiproliferative activity against human Ramos cells 21634430
Histone deacetylase 6 Ki = 247.0 nM 6.61 Competitive inhibition of HDAC6 using KI-104 as substrate by fluorescence assay 21634430
PC-3 IC50 = 340.0 nM 6.47 Antiproliferative activity against human PC3 cells 21634430
PC-3 IC50 = 340.0 nM 6.47 Antiproliferative activity against human PC3 cells after 96 hrs by celltiter 96 ... 21634430
HCT-116 IC50 = 480.0 nM 6.32 Antiproliferative activity against human HCT116 cells after 96 hrs by celltiter ... 21634430
A2780 IC50 = 480.0 nM 6.32 Antiproliferative activity against human A2780 cells after 96 hrs by celltiter 9... 21634430
COLO 205 IC50 = 560.0 nM 6.25 Antiproliferative activity against human COLO205 cells after 96 hrs by celltiter... 21634430
Cytochrome P450 3A4 IC50 = 2730.0 nM 5.56 Inhibition of recombinant CYP3A4 after 30 mins by fluorescence assay 21634430

Literature References

PubMed DOI Target Context # Activities
21634430 10.1021/jm2003552 Mus musculus 31
21634430 10.1021/jm2003552 Rattus norvegicus 10
21634430 10.1021/jm2003552 Canis familiaris 10
21634430 10.1021/jm2003552 No relevant target 6
21634430 10.1021/jm2003552 ADMET 6
21634430 10.1021/jm2003552 HCT-116 5
21634430 10.1021/jm2003552 Plasma 4
21634430 10.1021/jm2003552 MV4-11 3
21634430 10.1021/jm2003552 PC-3 3
21634430 10.1021/jm2003552 A2780 3
21634430 10.1021/jm2003552 Ramos 2
21634430 10.1021/jm2003552 Cytochrome P450 3A4 2
21634430 10.1021/jm2003552 Histone deacetylase 1 2
21634430 10.1021/jm2003552 Cytochrome P450 2D6 2
21634430 10.1021/jm2003552 Liver microsomes 2
21634430 10.1021/jm2003552 Liver 2
21634430 10.1021/jm2003552 Caco-2 2
21634430 10.1021/jm2003552 Histone deacetylase 8 1
21634430 10.1021/jm2003552 Histone deacetylase 9 1
21634430 10.1021/jm2003552 Matrix metalloproteinase-9 1

Data from ChEMBL 36 via Core Engine