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Compound Detail

CHEMBL491316

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O=C(/C=C/c1ccc2c(c1)nc(CCc1ccccc1)n2CCN1CCCC1)NO
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL491316
Phase Preclinical
Structure Type MOL
InChI Key RCDIZKAYZBEALO-JLHYYAGUSA-N
14
Targets
29
Activities
2
Assay Types
7
PK Parameters
20
Publications
0
Known Names

Molecular Properties

404.5
MW (Da)
3.44
ALogP
5
HBA
2
HBD
70.4
PSA (Ų)
0.34
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 C24H28N4O2
MW 404.51
Aromatic Rings 3
Heavy Atoms 30
NP-Likeness -1.05

Activity Summary

Ki 19 meas. best 8.07
IC50 10 meas. best 7.54

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase 4
CHEMBL3524
 Ki 8.07 8.045 8.5 2
Histone deacetylase 1
CHEMBL325
 Ki 7.96 7.96 11.0 1
Histone deacetylase 3
CHEMBL1829
 Ki 7.92 7.91 12.0 2
Histone deacetylase 11
CHEMBL3310
 Ki 7.89 7.89 12.8 2
Histone deacetylase 5
CHEMBL2563
 Ki 7.77 7.765 17.0 2
Histone deacetylase 9
CHEMBL4145
 Ki 7.72 7.72 19.0 2
Polyamine deacetylase HDAC10
CHEMBL5103
 Ki 7.72 7.72 18.9 2
Histone deacetylase 6
CHEMBL1865
 Ki 7.7 7.695 20.0 2
Histone deacetylase 1
CHEMBL325
 IC50 7.54 7.368 29.0 5
Histone deacetylase 2
CHEMBL1937
 Ki 7.44 7.44 36.0 2
Histone deacetylase 8
CHEMBL3192
 Ki 7.09 7.055 82.0 2
COLO 205
CHEMBL614561
 IC50 6.89 6.87 130.0 2
PC-3
CHEMBL390
 IC50 6.82 6.82 150.0 1
HCT-116
CHEMBL394
 IC50 6.72 6.72 190.0 1
A2780
CHEMBL614004
 IC50 6.72 6.72 190.0 1

Pharmacokinetic Data

Parameter Value Units Species
Cmax 920.0 nM Mus musculus
F 13.0 % Mus musculus
T1/2 0.05 hr Mus musculus
T1/2 0.5 hr Homo sapiens
T1/2 0.08333 hr Mus musculus
T1/2 0.07167 hr Rattus norvegicus
T1/2 0.3 hr Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase 4 Ki = 8.5 nM 8.07 Competitive inhibition of HDAC4 using KI-104 as substrate by fluorescence assay 21634430
Histone deacetylase 4 Ki = 9.6 nM 8.02 Inhibition of recombinant HDAC4 by fluorimetric assay 19181524
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 = 12.0 nM 7.92 Competitive inhibition of HDAC3 using KI-104 as substrate by fluorescence assay 21634430
Histone deacetylase 3 Ki = 12.5 nM 7.9 Inhibition of recombinant HDAC3 by fluorimetric assay 19181524
Histone deacetylase 11 Ki = 13.0 nM 7.89 Competitive inhibition of HDAC11 using KI-104 as substrate by fluorescence assay 21634430
Histone deacetylase 11 Ki = 12.8 nM 7.89 Inhibition of recombinant HDAC11 by fluorimetric assay 19181524
Histone deacetylase 5 Ki = 17.0 nM 7.77 Competitive inhibition of HDAC5 using KI-104 as substrate by fluorescence assay 21634430
Histone deacetylase 5 Ki = 17.2 nM 7.76 Inhibition of recombinant HDAC5 by fluorimetric assay 19181524
Histone deacetylase 9 Ki = 19.2 nM 7.72 Inhibition of recombinant HDAC9 by fluorimetric assay 19181524
Polyamine deacetylase HDAC10 Ki = 18.9 nM 7.72 Inhibition of recombinant HDAC10 by fluorimetric assay 19181524
Histone deacetylase 9 Ki = 19.0 nM 7.72 Competitive inhibition of HDAC9 using KI-104 as substrate by fluorescence assay 21634430
Polyamine deacetylase HDAC10 Ki = 19.0 nM 7.72 Competitive inhibition of HDAC10 using KI-104 as substrate by fluorescence assay 21634430
Histone deacetylase 6 Ki = 20.0 nM 7.7 Competitive inhibition of HDAC6 using KI-104 as substrate by fluorescence assay 21634430
Histone deacetylase 6 Ki = 20.6 nM 7.69 Inhibition of recombinant HDAC6 by fluorimetric assay 19181524
Histone deacetylase 1 IC50 = 29.0 nM 7.54 Inhibition of full length recombinant HDAC1 using Fluor de Lys as substrate by f... 21634430
Histone deacetylase 1 IC50 = 35.0 nM 7.46 Inhibition of recombinant HDAC1 by fluorimetric assay 19181524
Histone deacetylase 2 Ki = 36.2 nM 7.44 Inhibition of recombinant HDAC2 by fluorimetric assay 19181524
Histone deacetylase 2 Ki = 36.0 nM 7.44 Competitive inhibition of HDAC2 using KI-104 as substrate by fluorescence assay 21634430
Histone deacetylase 1 IC50 = 52.0 nM 7.28 Enzyme Assay: The assay has been carried out in 96 well format and the BIOMOL fl... -

Literature References

PubMed DOI Target Context # Activities
19181524 10.1016/j.bmcl.2009.01.041 Mus musculus 8
19181524 10.1016/j.bmcl.2009.01.041 HCT-116 5
21634430 10.1021/jm2003552 Caco-2 3
21634430 10.1021/jm2003552 Liver microsomes 2
21634430 10.1021/jm2003552 Liver 2
21634430 10.1021/jm2003552 Histone deacetylase 1 2
21634430 10.1021/jm2003552 No relevant target 2
19181524 10.1016/j.bmcl.2009.01.041 Histone deacetylase 11 1
21634430 10.1021/jm2003552 PC-3 1
21634430 10.1021/jm2003552 HCT-116 1
21634430 10.1021/jm2003552 COLO 205 1
20017493 10.1021/jm901502p ADMET 1
19181524 10.1016/j.bmcl.2009.01.041 Histone deacetylase 1 1
19181524 10.1016/j.bmcl.2009.01.041 Histone deacetylase 9 1
19181524 10.1016/j.bmcl.2009.01.041 Histone deacetylase 8 1
19181524 10.1016/j.bmcl.2009.01.041 Histone deacetylase 6 1
19181524 10.1016/j.bmcl.2009.01.041 Histone deacetylase 5 1
19181524 10.1016/j.bmcl.2009.01.041 Histone deacetylase 4 1
19181524 10.1016/j.bmcl.2009.01.041 Histone deacetylase 3 1
19181524 10.1016/j.bmcl.2009.01.041 Histone deacetylase 2 1

Data from ChEMBL 36 via Core Engine