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Compound Detail

CHEMBL489332

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O=C(/C=C/c1ccc2c(c1)nc(CCc1ccccc1)n2CCN1CCCCC1)NO
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL489332
Phase Preclinical
Structure Type MOL
InChI Key XZWCFUZJOAZGAI-SDNWHVSQSA-N
15
Targets
22
Activities
3
Assay Types
2
PK Parameters
20
Publications
0
Known Names

Molecular Properties

418.5
MW (Da)
3.83
ALogP
5
HBA
2
HBD
70.4
PSA (Ų)
0.33
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C25H30N4O2
MW 418.54
Aromatic Rings 3
Heavy Atoms 31
NP-Likeness -1.03

Activity Summary

IC50 12 meas. best 7.64
Ki 9 meas. best 8.06
EC50 1 meas. best 6.3

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase 4
CHEMBL3524
 Ki 8.06 8.06 8.7 1
Histone deacetylase 3
CHEMBL1829
 Ki 7.96 7.96 11.0 1
Histone deacetylase 1
CHEMBL325
 Ki 7.92 7.92 12.0 1
Histone deacetylase 11
CHEMBL3310
 Ki 7.85 7.85 14.0 1
Histone deacetylase 5
CHEMBL2563
 Ki 7.75 7.75 18.0 1
Histone deacetylase 1
CHEMBL325
 IC50 7.64 7.49 23.0 5
Polyamine deacetylase HDAC10
CHEMBL5103
 Ki 7.64 7.64 23.0 1
Histone deacetylase 9
CHEMBL4145
 Ki 7.62 7.62 24.0 1
Histone deacetylase 6
CHEMBL1865
 Ki 7.57 7.57 27.0 1
A2780
CHEMBL614004
 IC50 7.51 7.51 31.0 1
Histone deacetylase 2
CHEMBL1937
 Ki 7.41 7.41 39.0 1
COLO 205
CHEMBL614561
 IC50 7.06 7.055 87.0 2
HCT-116
CHEMBL394
 IC50 7.0 7.0 100.0 1
PC-3
CHEMBL390
 IC50 6.92 6.92 120.0 1
Histone deacetylase 8
CHEMBL3192
 IC50 6.59 6.59 254.0 2
Unchecked
CHEMBL612545
 EC50 6.3 6.3 500.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 1.5 hr Homo sapiens
T1/2 0.5833 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase 4 Ki = 8.7 nM 8.06 Competitive inhibition of HDAC4 using KI-104 as substrate by fluorescence assay 21634430
Histone deacetylase 3 Ki = 11.0 nM 7.96 Competitive inhibition of HDAC3 using KI-104 as substrate by fluorescence assay 21634430
Histone deacetylase 1 Ki = 12.0 nM 7.92 Competitive inhibition of HDAC1 using KI-104 as substrate by fluorescence assay 21634430
Histone deacetylase 11 Ki = 14.0 nM 7.85 Competitive inhibition of HDAC11 using KI-104 as substrate by fluorescence assay 21634430
Histone deacetylase 5 Ki = 18.0 nM 7.75 Competitive inhibition of HDAC5 using KI-104 as substrate by fluorescence assay 21634430
Histone deacetylase 1 IC50 = 23.0 nM 7.64 Inhibition of full length recombinant HDAC1 using Fluor de Lys as substrate by f... 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 9 Ki = 24.0 nM 7.62 Competitive inhibition of HDAC9 using KI-104 as substrate by fluorescence assay 21634430
Histone deacetylase 1 IC50 = 26.0 nM 7.58 Inhibition of recombinant HDAC1 by fluorimetric assay 19181524
Histone deacetylase 6 Ki = 27.0 nM 7.57 Competitive inhibition of HDAC6 using KI-104 as substrate by fluorescence assay 21634430
A2780 IC50 = 31.0 nM 7.51 Antiproliferative activity against human A2780 cells after 96 hrs by celltiter 9... 21634430
Histone deacetylase 2 Ki = 39.0 nM 7.41 Competitive inhibition of HDAC2 using KI-104 as substrate by fluorescence assay 21634430
Histone deacetylase 1 IC50 = 39.0 nM 7.41 Enzyme Assay: The assay has been carried out in 96 well format and the BIOMOL fl... -
Histone deacetylase 1 IC50 = 39.0 nM 7.41 In Vitro HDAC Assay: The assay has been carried out in 96 well format and the BI... -
Histone deacetylase 1 IC50 = 39.0 nM 7.41 Enzyme Assay: The assay have been carried out in a 96 well format and the BIOMOL... -
COLO 205 IC50 = 87.0 nM 7.06 Antiproliferative activity against human COLO205 cells after 96 hrs by celltiter... 21634430
COLO 205 IC50 = 90.0 nM 7.05 Antiproliferative activity against human COLO205 cells after 96 hrs by celltiter... 19181524
HCT-116 IC50 = 100.0 nM 7.0 Antiproliferative activity against human HCT116 cells after 96 hrs by celltiter ... 21634430
PC-3 IC50 = 120.0 nM 6.92 Antiproliferative activity against human PC3 cells after 96 hrs by celltiter 96 ... 21634430
Histone deacetylase 8 IC50 = 254.0 nM 6.59 Histone H3 Acetylation Assay: To determine EC50 where acetylated histone 3 was i... -

Literature References

PubMed DOI Target Context # Activities
21634430 10.1021/jm2003552 Histone deacetylase 1 2
21634430 10.1021/jm2003552 Histone deacetylase 3 1
21634430 10.1021/jm2003552 Liver 1
21634430 10.1021/jm2003552 Liver microsomes 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 6 1
21634430 10.1021/jm2003552 Histone deacetylase 5 1
21634430 10.1021/jm2003552 Histone deacetylase 4 1
19181524 10.1016/j.bmcl.2009.01.041 Histone deacetylase 1 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
19181524 10.1016/j.bmcl.2009.01.041 HCT-116 1
19181524 10.1016/j.bmcl.2009.01.041 Mus musculus 1

Data from ChEMBL 36 via Core Engine