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Compound Detail

CHEMBL3593247

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CC(C)[C@@H]1NC(=O)[C@]2(C)CSC(=N2)c2csc(n2)CNC(=O)C[C@@H](/C=C/CCS)OC1=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3593247
Phase Preclinical
Structure Type MOL
InChI Key VEDPEVJAYWVUSJ-BNVDZZMOSA-N
8
Targets
25
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

496.7
MW (Da)
2.34
ALogP
9
HBA
3
HBD
109.8
PSA (Ų)
0.34
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 C21H28N4O4S3
MW 496.68
Aromatic Rings 1
Heavy Atoms 32
NP-Likeness 1.76

Activity Summary

IC50 25 meas. best 9.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase 1
CHEMBL325
 IC50 9.4 9.025 0.4 4
Polyamine deacetylase HDAC10
CHEMBL5103
 IC50 9.3 9.3 0.5 1
Histone deacetylase 3
CHEMBL1829
 IC50 9.15 8.855 0.7 2
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2)
CHEMBL2111363
 IC50 9.15 8.495 0.7 2
Histone deacetylase 2
CHEMBL1937
 IC50 9.05 8.625 0.9 4
Histone deacetylase 8
CHEMBL3192
 IC50 8.42 7.206 3.8 5
Histone deacetylase 6
CHEMBL1865
 IC50 7.55 7.2833 28.1 3
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 7.1 7.05 80.0 4

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase 1 IC50 = 0.4 nM 9.4 Inhibition of human HDAC1 30108795
Histone deacetylase 1 IC50 = 0.4 nM 9.4 Inhibition of recombinant full length C-terminal His/FLAG-tagged human HDAC1 exp... 28416100
Polyamine deacetylase HDAC10 IC50 = 0.5 nM 9.3 Inhibition of N-terminal GST-tagged/C-terminal His-tagged human HDAC10 (1 to 481... 28416100
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2) IC50 = 0.7 nM 9.15 Inhibition of full length human C-terminal His-tagged HDAC3/N-terminal GST-tagge... 28416100
Histone deacetylase 3 IC50 = 0.7 nM 9.15 Inhibition of human HDAC3 30108795
Histone deacetylase 2 IC50 = 0.9 nM 9.05 Inhibition of full length C-terminal FLAG-tagged human HDAC2 expressed in baculo... 28416100
Histone deacetylase 2 IC50 = 0.9 nM 9.05 Inhibition of human HDAC2 30108795
Histone deacetylase 1 IC50 = 2.0 nM 8.7 Inhibition of recombinant full length C-terminal FLAG/His-tagged human HDAC1 exp... 31505452
Histone deacetylase 1 IC50 = 2.51 nM 8.6 Inhibition of recombinant full-length HDAC1 (unknown origin) using MAZ1600/MAZ16... 26054247
Histone deacetylase 3 IC50 = 2.78 nM 8.56 Inhibition of recombinant full-length HDAC3 (unknown origin) using MAZ1600/MAZ16... 26054247
Histone deacetylase 8 IC50 = 3.8 nM 8.42 Inhibition of full length C-terminal His-tagged human HDAC8 expressed in baculov... 31505452
Histone deacetylase 2 IC50 = 4.19 nM 8.38 Inhibition of recombinant full-length HDAC2 (unknown origin) using MAZ1600/MAZ16... 26054247
Histone deacetylase 2 IC50 = 9.5 nM 8.02 Inhibition of recombinant full length human HDAC2 expressed in baculovirus infec... 31505452
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2) IC50 = 14.5 nM 7.84 Inhibition of human recombinant full length C-terminal His-tagged HDAC3 (1 to 42... 31505452
Histone deacetylase 6 IC50 = 28.11 nM 7.55 Inhibition of recombinant full-length HDAC6 (unknown origin) using MAZ1600/MAZ16... 26054247
Histone deacetylase 6 IC50 = 42.0 nM 7.38 Inhibition of full length N-terminal GST-tagged human HDAC6 expressed in baculov... 28416100
NON-PROTEIN TARGET IC50 = 80.0 nM 7.1 Cytotoxicity against human NMC-10326 cells assessed as cell viability after 48 h... 26054247
NON-PROTEIN TARGET IC50 = 82.6 nM 7.08 Cytotoxicity against human NMC-10326 cells assessed as cell viability after 48 h... 26054247
NON-PROTEIN TARGET IC50 = 96.38 nM 7.02 Cytotoxicity against human NMC-797 cells assessed as cell viability after 48 hrs... 26054247
NON-PROTEIN TARGET IC50 = 100.0 nM 7.0 Cytotoxicity against human NMC-797 cells assessed as cell viability after 48 hrs... 26054247

Literature References

PubMed DOI Target Context # Activities
26054247 10.1016/j.bmc.2015.03.063 NON-PROTEIN TARGET 4
31505452 10.1016/j.ejmech.2019.111672 Histone deacetylase 8 3
31505452 10.1016/j.ejmech.2019.111672 Histone deacetylase 6 2
31505452 10.1016/j.ejmech.2019.111672 Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2) 2
31505452 10.1016/j.ejmech.2019.111672 Histone deacetylase 2 2
31505452 10.1016/j.ejmech.2019.111672 Histone deacetylase 1 2
26054247 10.1016/j.bmc.2015.03.063 Histone deacetylase 1 2
28416100 10.1016/j.bmc.2017.03.071 Histone deacetylase 6 1
31505452 10.1016/j.ejmech.2019.111672 Unchecked 1
30108795 10.1039/C6MD00633G Histone deacetylase 3 1
30108795 10.1039/C6MD00633G Histone deacetylase 8 1
28416100 10.1016/j.bmc.2017.03.071 Polyamine deacetylase HDAC10 1
28416100 10.1016/j.bmc.2017.03.071 Histone deacetylase 8 1
28416100 10.1016/j.bmc.2017.03.071 Histone deacetylase 5 1
28416100 10.1016/j.bmc.2017.03.071 Histone deacetylase 1 1
28416100 10.1016/j.bmc.2017.03.071 Histone deacetylase 2 1
28416100 10.1016/j.bmc.2017.03.071 Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2) 1
26054247 10.1016/j.bmc.2015.03.063 Histone deacetylase 8 1
26054247 10.1016/j.bmc.2015.03.063 Histone deacetylase 6 1
26054247 10.1016/j.bmc.2015.03.063 Histone deacetylase 3 1

Data from ChEMBL 36 via Core Engine