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Compound Detail

CHEMBL235842

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CC(=O)Nc1ccc(C(=O)Nc2cc(-c3cccs3)ccc2N)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL235842
Phase Preclinical
Structure Type MOL
InChI Key ABZSPJVXTTUFAA-UHFFFAOYSA-N
7
Targets
32
Activities
4
Assay Types
13
PK Parameters
20
Publications
0
Known Names

Molecular Properties

351.4
MW (Da)
4.21
ALogP
4
HBA
3
HBD
84.2
PSA (Ų)
0.62
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C19H17N3O2S
MW 351.43
Aromatic Rings 3
Heavy Atoms 25
NP-Likeness -1.65

Activity Summary

IC50 24 meas. best 9.0
Ki 5 meas. best 8.82
Kd 2 meas. best 7.42
EC50 1 meas. best 6.03

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase 1
CHEMBL325
 IC50 9.0 7.86 1.0 10
Histone deacetylase 2
CHEMBL1937
 Ki 8.82 8.6367 1.5 3
Histone deacetylase 2
CHEMBL1937
 IC50 8.1 7.445 8.0 8
Histone deacetylase 2
CHEMBL1937
 Kd 7.42 7.42 38.0 1
Histone deacetylase 1
CHEMBL325
 Kd 7.26 7.26 55.0 1
Histone deacetylase 3
CHEMBL1829
 Ki 6.57 6.435 270.0 2
Histone deacetylase
CHEMBL2093865
 IC50 6.52 6.52 300.0 1
Histone deacetylase 3
CHEMBL1829
 IC50 6.4 5.9133 398.0 3
HCT-116
CHEMBL394
 IC50 6.3 6.3 500.0 1
Human immunodeficiency virus 1
CHEMBL378
 EC50 6.03 6.03 930.0 1
KB
CHEMBL398
 IC50 5.28 5.28 5270.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 2.8 microM.hr/mg/kg Rattus norvegicus
CL 12.0 mL.min-1.kg-1 Rattus norvegicus
Cmax 1400.0 nM Rattus norvegicus
F 64.0 % Rattus norvegicus
ka 0.8 /uM/min Homo sapiens
T1/2 9.7 hr Rattus norvegicus
T1/2 40.0 hr Homo sapiens
T1/2 80.0 hr Homo sapiens
T1/2 20.0 hr Homo sapiens
T1/2 40.0 hr Homo sapiens
T1/2 80.0 hr Homo sapiens
T1/2 20.0 hr Homo sapiens
T1/2 6.44 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase 1 IC50 = 1.0 nM 9.0 Inhibition of C-terminal His-tagged and C-terminal FLAG-tagged full length human... 27377864
Histone deacetylase 1 IC50 = 1.0 nM 9.0 Inhibition of recombinant human HDAC1 37651268
Histone deacetylase 1 IC50 = 1.0 nM 9.0 Inhibition of HDAC1 (unknown origin) 36399875
Histone deacetylase 2 Ki = 1.5 nM 8.82 Inhibition full length human recombinant HDAC2 expressed in baculovirus coexpres... 27377864
Histone deacetylase 2 Ki = 1.5 nM 8.82 Binding affinity to recombinant human HDAC2 assessed as inhibition constant 37651268
Histone deacetylase 2 Ki = 5.4 nM 8.27 Inhibition of full-length recombinant human C-terminal GST tagged HDAC2 expresse... 37847303
Histone deacetylase 1 IC50 = 7.0 nM 8.15 Inhibition of HDAC1 18182289
Histone deacetylase 2 IC50 = 8.0 nM 8.1 Inhibition of recombinant human HDAC2 37651268
Histone deacetylase 2 IC50 = 8.0 nM 8.1 Inhibition of HDAC2 (unknown origin) 36399875
Histone deacetylase 2 IC50 = 13.0 nM 7.89 Inhibition full length human recombinant HDAC2 expressed in baculovirus coexpres... 27377864
Histone deacetylase 2 Kd = 38.0 nM 7.42 Binding affinity to C-terminal His-tagged human HDAC2 (2 to 488 residues) in tra... 37651268
Histone deacetylase 1 IC50 = 40.0 nM 7.4 Inhibition of wild-type FLAG-tagged HDAC1 (unknown origin) expressed in Jurkat c... 24405391
Histone deacetylase 1 IC50 = 40.0 nM 7.4 Inhibition of recombinant HDAC1 20223566
Histone deacetylase 1 IC50 = 40.0 nM 7.4 Inhibition of HDAC1 18247554
Histone deacetylase 1 IC50 = 40.0 nM 7.4 Inhibition of human recombinant HDAC1 17941625
Histone deacetylase 2 IC50 = 49.0 nM 7.31 Inhibition of HDAC2 18182289
Histone deacetylase 1 Kd = 55.0 nM 7.26 Binding affinity to human HDAC1 assessed as dissociation constant 37651268
Histone deacetylase 1 IC50 = 70.0 nM 7.16 Inhibition of full length human recombinant C-terminal FLAG/His-tagged HDAC1 exp... 29541372
Histone deacetylase 2 IC50 = 70.0 nM 7.16 Inhibition of full length human recombinant C-terminal His-tagged HDAC2 expresse... 29541372
Histone deacetylase 2 IC50 = 100.0 nM 7.0 Inhibition of HDAC2 18247554

Literature References

PubMed DOI Target Context # Activities
37651268 10.1021/acs.jmedchem.3c01160 Histone deacetylase 1 7
37651268 10.1021/acs.jmedchem.3c01160 Histone deacetylase 2 7
18182289 10.1016/j.bmcl.2007.12.031 Rattus norvegicus 6
24405391 10.1021/jm401837e Unchecked 6
27377864 10.1016/j.bmc.2016.06.040 Histone deacetylase 2 5
27377864 10.1016/j.bmc.2016.06.040 Histone deacetylase 1 5
18182289 10.1016/j.bmcl.2007.12.031 HCT-116 4
27377864 10.1016/j.bmc.2016.06.040 Histone deacetylase 3 4
29541372 10.1021/acsmedchemlett.8b00012 Unchecked 4
37847303 10.1021/acs.jmedchem.3c01095 Histone deacetylase 2 4
37651268 10.1021/acs.jmedchem.3c01160 Histone deacetylase 3 3
29541372 10.1021/acsmedchemlett.8b00012 Human immunodeficiency virus 1 3
17941625 10.1021/jm701079h Histone deacetylase 1 2
- 10.6019/CHEMBL5096127 Schistosoma mansoni 2
37651268 10.1021/acs.jmedchem.3c01160 Unchecked 2
24405391 10.1021/jm401837e Histone deacetylase 1 2
17941625 10.1021/jm701079h Histone deacetylase 2
17941625 10.1021/jm701079h Histone deacetylase 8 2
17941625 10.1021/jm701079h Histone deacetylase 3 2
17941625 10.1021/jm701079h Histone deacetylase 2 2

Data from ChEMBL 36 via Core Engine