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Compound Detail

CHEMBL2448576

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CCC(=O)CCCCC[C@H](NC(=O)C1CN(C)C1)c1ncc(-c2cc3ccccc3nc2OC)[nH]1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2448576
Phase Preclinical
Structure Type MOL
InChI Key AWTXQEUYEIEIGL-QHCPKHFHSA-N
8
Targets
20
Activities
2
Assay Types
11
PK Parameters
20
Publications
0
Known Names

Molecular Properties

477.6
MW (Da)
4.28
ALogP
6
HBA
2
HBD
100.2
PSA (Ų)
0.38
QED
0
Ro5 Violations
12
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C27H35N5O3
MW 477.61
Aromatic Rings 3
Heavy Atoms 35
NP-Likeness -0.36

Activity Summary

IC50 16 meas. best 9.22
EC50 4 meas. best 6.96

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase 3
CHEMBL1829
 IC50 9.22 8.3533 0.6 3
Histone deacetylase 1
CHEMBL325
 IC50 8.7 8.16 2.0 3
Histone deacetylase 2
CHEMBL1937
 IC50 8.15 7.8833 7.0 3
Human immunodeficiency virus
CHEMBL613758
 EC50 6.96 6.64 110.0 4
Class 1 histone deacetylase
CHEMBL4523988
 IC50 6.7 6.2833 200.0 3
Histone deacetylase 6
CHEMBL1865
 IC50 6.17 6.17 680.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 5.52 5.52 3000.0 1
Cytochrome P450 2C9
CHEMBL3397
 IC50 5.26 5.26 5500.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 429.85 ng.hr.mL-1 Mus musculus
CL 29.0 mL.min-1.g-1 Rattus norvegicus
CL 29.0 mL.min-1.g-1 Canis lupus familiaris
CL 31.0 mL.min-1.g-1 Homo sapiens
CL 19.0 mL.min-1.kg-1 Rattus norvegicus
CL 4.0 mL.min-1.kg-1 Canis lupus familiaris
F 73.0 % Rattus norvegicus
F 31.0 % Canis lupus familiaris
Fu 0.0574 - Rattus norvegicus
T1/2 7.0 hr Rattus norvegicus
T1/2 14.0 hr Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase 3 IC50 = 0.6 nM 9.22 Inhibition of recombinant human FLAG-tagged HDAC3 expressed in human HEK293F cel... 33854701
Histone deacetylase 1 IC50 = 2.0 nM 8.7 Inhibition of recombinant human C-terminal FLAG-tagged HDAC1 expressed in human ... 33854701
Histone deacetylase 2 IC50 = 7.0 nM 8.15 Inhibition of recombinant human C-terminal FLAG-tagged HDAC2 expressed in human ... 33854701
Histone deacetylase 3 IC50 = 12.0 nM 7.92 Inhibition of human C-terminal FLAG-tagged HDAC3 in HEK293 cells 19441846
Histone deacetylase 3 IC50 = 12.0 nM 7.92 Inhibition of HDAC3 (unknown origin) 34091041
Histone deacetylase 1 IC50 = 13.0 nM 7.89 Inhibition of HDAC1 (unknown origin) 34091041
Histone deacetylase 1 IC50 = 13.0 nM 7.89 Inhibition of human C-terminal FLAG-tagged HDAC1 in HEK293 cells 19441846
Histone deacetylase 2 IC50 = 18.0 nM 7.75 Inhibition of HDAC2 (unknown origin) 34091041
Histone deacetylase 2 IC50 = 18.0 nM 7.75 Inhibition of human C-terminal FLAG-tagged HDAC2 in HEK293 cells 19441846
Human immunodeficiency virus EC50 = 110.0 nM 6.96 Reactivation of HIV latency infected in human 2C4 cells in presence of 0.1 % NHS... 34091041
Human immunodeficiency virus EC50 = 110.0 nM 6.96 Reactivation of HIV latency infected in human 2C4 cells in presence of 0.1 % NHS... 32331932
Class 1 histone deacetylase IC50 = 200.0 nM 6.7 Inhibition of class 1 HDAC in human Jurkat 2C4 model of HIV latency assessed as ... 33854701
Human immunodeficiency virus EC50 = 477.0 nM 6.32 Reactivation of HIV latency infected in human 2C4 cells in presence of 5 % NHS b... 34091041
Human immunodeficiency virus EC50 = 477.0 nM 6.32 Reactivation of HIV latency infected in human 2C4 cells in presence of 5 % NHS b... 32331932
Histone deacetylase 6 IC50 = 680.0 nM 6.17 Inhibition of HDAC6 (unknown origin) 34091041
Class 1 histone deacetylase IC50 = 710.0 nM 6.15 Inhibition of class 1 HDAC in quiescent human primary T-cell model of VSV-G pseu... 33854701
Class 1 histone deacetylase IC50 = 1000.0 nM 6.0 Inhibition of class 1 HDAC in human Jurkat 2C4 model of HIV latency assessed as ... 33854701
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 3000.0 nM 5.52 Inhibition of hERG potassium channel incubated for 4 hrs by fluorescence polariz... 30996783
Cytochrome P450 2C9 IC50 = 5500.0 nM 5.26 Inhibition of CYP2C9 19441846

Literature References

PubMed DOI Target Context # Activities
19441846 10.1021/jm9004303 Canis familiaris 7
19441846 10.1021/jm9004303 Rattus norvegicus 5
19441846 10.1021/jm9004303 Mus musculus 3
19441846 10.1021/jm9004303 Unchecked 3
33854701 10.1021/acsmedchemlett.1c00074 Class 1 histone deacetylase 3
19441846 10.1021/jm9004303 HCT-116 3
19441846 10.1021/jm9004303 Liver microsomes 2
19441846 10.1021/jm9004303 Cytochrome P450 3A4 2
32331932 10.1016/j.bmcl.2020.127197 Human immunodeficiency virus 2
34091041 10.1016/j.bmcl.2021.128168 Human immunodeficiency virus 2
32676157 10.1021/acsmedchemlett.0c00302 Histone deacetylase 3/NCoR1 2
19441846 10.1021/jm9004303 Histone deacetylase 7 1
19441846 10.1021/jm9004303 MCF7 1
19441846 10.1021/jm9004303 G-401 1
19441846 10.1021/jm9004303 A549 1
19441846 10.1021/jm9004303 Histone deacetylase 8 1
19441846 10.1021/jm9004303 Histone deacetylase 5 1
19441846 10.1021/jm9004303 Histone deacetylase 3 1
30996783 10.1021/acsmedchemlett.8b00517 ADMET 1
19441846 10.1021/jm9004303 ADMET 1

Data from ChEMBL 36 via Core Engine