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Compound Detail

CHEMBL1796689

LARGAZOLE THIOL
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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 CHEMBL1796689
Name LARGAZOLE THIOL
Phase Preclinical
Structure Type MOL
InChI Key VEDPEVJAYWVUSJ-FJNFOTEGSA-N
8
Targets
15
Activities
1
Assay Types
1
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 15 meas. best 9.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase 1
CHEMBL325
 IC50 9.4 9.24 0.4 3
Polyamine deacetylase HDAC10
CHEMBL5103
 IC50 9.3 9.3 0.5 1
Histone deacetylase 3
CHEMBL1829
 IC50 9.15 8.9233 0.7 3
Histone deacetylase 2
CHEMBL1937
 IC50 9.05 9.05 0.9 2
Histone deacetylase 11
CHEMBL3310
 IC50 8.52 8.52 3.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 8.23 8.23 5.9 1
Histone deacetylase 6
CHEMBL1865
 IC50 7.46 7.385 35.0 2
Histone deacetylase 8
CHEMBL3192
 IC50 6.99 6.99 102.0 2

Pharmacokinetic Data

Parameter Value Units Species
T1/2 0.85 hr Mus musculus

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 HDAC1 (unknown origin) incubated at 37 degC for 30 mins 25070421
Histone deacetylase 1 IC50 = 0.4 nM 9.4 Inhibition of HDAC1 (unknown origin) incubated for 30 mins in presence of BSA an... 25147612
Polyamine deacetylase HDAC10 IC50 = 0.5 nM 9.3 Inhibition of HDAC10 (unknown origin) incubated for 30 mins in presence of BSA a... 25147612
Histone deacetylase 3 IC50 = 0.7 nM 9.15 Inhibition of HDAC3 (unknown origin) incubated at 37 degC for 30 mins 25070421
Histone deacetylase 3 IC50 = 0.7 nM 9.15 Inhibition of HDAC3 (unknown origin) incubated for 30 mins in presence of BSA an... 25147612
Histone deacetylase 2 IC50 = 0.9 nM 9.05 Inhibition of HDAC2 (unknown origin) incubated at 37 degC for 30 mins 25070421
Histone deacetylase 2 IC50 = 0.9 nM 9.05 Inhibition of HDAC2 (unknown origin) incubated for 30 mins in presence of BSA an... 25147612
Histone deacetylase 1 IC50 = 1.2 nM 8.92 Inhibition of recombinant human HDAC1 using Ac-Lys-Tyr-Lys(epsilon-acetyl)-AMC a... 24944733
Histone deacetylase 11 IC50 = 3.0 nM 8.52 Inhibition of HDAC11 (unknown origin) incubated for 3 hrs in presence of BSA and... 25147612
Histone deacetylase 3 IC50 = 3.4 nM 8.47 Inhibition of recombinant human HDAC3 using Ac-Lys-Tyr-Lys(epsilon-acetyl)-AMC a... 24944733
NON-PROTEIN TARGET IC50 = 5.9 nM 8.23 Antiproliferative activity against human HCT116 cells after 48 hrs in absence of... 25147612
Histone deacetylase 6 IC50 = 35.0 nM 7.46 Inhibition of HDAC6 (unknown origin) incubated for 30 mins in presence of BSA an... 25147612
Histone deacetylase 6 IC50 = 49.0 nM 7.31 Inhibition of recombinant human HDAC6 using Boc-Lys(epsilon-acetyl)-AMC as subst... 24944733
Histone deacetylase 8 IC50 = 102.0 nM 6.99 Inhibition of HDAC8 (unknown origin) incubated at 37 degC for 30 mins 25070421
Histone deacetylase 8 IC50 = 102.0 nM 6.99 Inhibition of HDAC8 (unknown origin) incubated for 30 mins in presence of BSA an... 25147612

Literature References

PubMed DOI Target Context # Activities
25147612 10.1021/ml500170r ADMET 4
21420302 10.1016/j.bmc.2011.02.024 Histone deacetylase 4
25070421 10.1016/j.bmcl.2014.07.006 Unchecked 2
25147612 10.1021/ml500170r Histone deacetylase 9 2
25147612 10.1021/ml500170r Histone deacetylase 7 2
25147612 10.1021/ml500170r Histone deacetylase 5 2
25147612 10.1021/ml500170r Histone deacetylase 4 2
25070421 10.1016/j.bmcl.2014.07.006 Histone deacetylase 1 1
25070421 10.1016/j.bmcl.2014.07.006 Histone deacetylase 3 1
25070421 10.1016/j.bmcl.2014.07.006 Histone deacetylase 8 1
25070421 10.1016/j.bmcl.2014.07.006 Histone deacetylase 2 1
25147612 10.1021/ml500170r Histone deacetylase 1 1
25147612 10.1021/ml500170r Histone deacetylase 2 1
25147612 10.1021/ml500170r Histone deacetylase 3 1
24944733 10.1021/ml400470s Histone deacetylase 6 1
24944733 10.1021/ml400470s Histone deacetylase 3 1
25147612 10.1021/ml500170r Histone deacetylase 6 1
24944733 10.1021/ml400470s Histone deacetylase 1 1
25147612 10.1021/ml500170r Serum 1
21420302 10.1016/j.bmc.2011.02.024 Liver 1

Data from ChEMBL 36 via Core Engine