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Compound Detail

CHEMBL1173445

LARGAZOLE
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CCCCCCCC(=O)SCC/C=C/[C@@H]1CC(=O)NCc2nc(cs2)C2=N[C@@](C)(CS2)C(=O)N[C@@H](C(C)C)C(=O)O1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1173445
Name LARGAZOLE
Phase Preclinical
Structure Type MOL
InChI Key AXESYCSCGBQJBL-SZPBEECKSA-N
21
Targets
69
Activities
2
Assay Types
3
PK Parameters
20
Publications
0
Known Names

Molecular Properties

622.9
MW (Da)
5.03
ALogP
10
HBA
2
HBD
126.8
PSA (Ų)
0.20
QED
2
Ro5 Violations
11
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C29H42N4O5S3
MW 622.88
Aromatic Rings 1
Heavy Atoms 41
NP-Likeness 1.33

Activity Summary

IC50 61 meas. best 8.8
EC50 8 meas. best 7.91

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
MDA-MB-231
CHEMBL400
 IC50 8.8 7.06 1.6 2
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 8.43 7.2742 3.7 12
Histone deacetylase 3
CHEMBL1829
 IC50 8.04 6.6114 9.1 7
Histone deacetylase 1
CHEMBL325
 IC50 8.0 7.186 10.1 10
IMR-32
CHEMBL614585
 EC50 7.91 7.63 12.3 3
Caco-2
CHEMBL614058
 EC50 7.84 6.98 14.4 2
Histone deacetylase 2
CHEMBL1937
 IC50 7.73 6.425 18.6 6
HCT-116
CHEMBL394
 IC50 7.7 7.1567 20.0 3
A549
CHEMBL392
 IC50 7.11 6.725 77.0 2
NCI-H1975
CHEMBL614348
 IC50 7.08 7.08 83.0 1
Histone deacetylase 8
CHEMBL3192
 IC50 6.92 6.445 120.0 2
NCI-H460
CHEMBL396
 IC50 6.92 6.92 120.0 1
Histone deacetylase 6
CHEMBL1865
 IC50 6.78 5.8 165.6 6
SK-OV-3
CHEMBL614925
 IC50 6.6 6.6 250.0 1
U2OS
CHEMBL615023
 EC50 6.48 5.8667 331.1 3
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2)
CHEMBL2111363
 IC50 5.7 5.7 2002.0 1
Polyamine deacetylase HDAC10
CHEMBL5103
 IC50 5.66 5.66 2210.0 1
Histone deacetylase 4
CHEMBL3524
 IC50 5.52 5.52 3000.0 2
Histone deacetylase 9
CHEMBL4145
 IC50 5.08 5.08 8330.0 1
Ubiquitin-like modifier-activating enzyme 1
CHEMBL5924
 IC50 4.54 4.54 29000.0 1
Unchecked
CHEMBL612545
 IC50 4.54 4.54 29000.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 0.08333 hr Mus musculus
Tmax 4.0 hr Homo sapiens
Tmax 4.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
MDA-MB-231 IC50 = 1.6 nM 8.8 Cytotoxicity against human MDA-MB-231 cells assessed as reduction in cell viabil... 28416100
NON-PROTEIN TARGET IC50 = 3.7 nM 8.43 Cytotoxicity against oncogenic KRAS knockout human HCT116 cells expressing wild ... 27380142
NON-PROTEIN TARGET IC50 = 6.41 nM 8.19 Cytotoxicity against human HCT116 cells assessed as reduction in cell viability ... 27380142
Histone deacetylase 3 IC50 = 9.09 nM 8.04 Inhibition of recombinant full-length HDAC3 (unknown origin) using MAZ1600/MAZ16... 26054247
Histone deacetylase 1 IC50 = 10.09 nM 8.0 Inhibition of recombinant full-length HDAC1 (unknown origin) using MAZ1600/MAZ16... 26054247
Histone deacetylase 1 IC50 = 11.4 nM 7.94 Inhibition of HDAC1 (unknown origin) 34826681
Histone deacetylase 1 IC50 = 11.4 nM 7.94 Inhibition of human recombinant HDAC1 after 15 mins by fluorimetric assay 20491440
IMR-32 EC50 = 12.3 nM 7.91 Antiproliferative activity against human IMR32 cells assessed as reduction in ce... 32435394
Histone deacetylase 1 IC50 = 13.7 nM 7.86 Inhibition of recombinant human HDAC1 using Ac-Lys-Tyr-Lys(epsilon-acetyl)-AMC a... 24944733
Caco-2 EC50 = 14.45 nM 7.84 Antiproliferative activity against human Caco2 cells assessed as reduction in ce... 32435394
NON-PROTEIN TARGET IC50 = 18.0 nM 7.75 Cytotoxicity against human HIF1alpha and HIF2alpha deficit HCT116 cells assessed... 27380142
Histone deacetylase 2 IC50 = 18.65 nM 7.73 Inhibition of recombinant full-length HDAC2 (unknown origin) using MAZ1600/MAZ16... 26054247
HCT-116 IC50 = 20.0 nM 7.7 Cytotoxicity against human HCT116 cells assessed as reduction in cell viability ... 28416100
NON-PROTEIN TARGET IC50 = 23.93 nM 7.62 Cytotoxicity against human NMC-797 cells assessed as cell viability after 48 hrs... 26054247
NON-PROTEIN TARGET IC50 = 24.0 nM 7.62 Cytotoxicity against human NMC-797 cells assessed as cell viability after 48 hrs... 26054247
NON-PROTEIN TARGET IC50 = 24.77 nM 7.61 Cytotoxicity against human NMC-10326 cells assessed as cell viability after 48 h... 26054247
NON-PROTEIN TARGET IC50 = 25.0 nM 7.6 Cytotoxicity against human NMC-10326 cells assessed as cell viability after 48 h... 26054247
IMR-32 EC50 = 30.2 nM 7.52 Antiproliferative activity against human IMR32 cells assessed as reduction in ce... 32435394
IMR-32 EC50 = 34.67 nM 7.46 Antiproliferative activity against human IMR32 cells assessed as reduction in ce... 32435394
HCT-116 IC50 = 44.0 nM 7.36 Antiproliferative activity against human HCT116 cells assessed as reduction in c... 31505452

Literature References

PubMed DOI Target Context # Activities
24900585 10.1021/ml400093y A549 29
28109947 10.1016/j.ejmech.2016.12.032 Unchecked 12
24900585 10.1021/ml400093y Transcription factor E2F1 11
21666868 10.1021/ml1002794 C2C12 10
24900585 10.1021/ml400093y NCI-H460 9
24900585 10.1021/ml400093y Histone deacetylase 1 8
20491440 10.1021/jm100244y NB-4 5
24900585 10.1021/ml400093y NON-PROTEIN TARGET 5
27380142 10.1021/acs.jnatprod.6b00203 NON-PROTEIN TARGET 5
21420302 10.1016/j.bmc.2011.02.024 Histone deacetylase 4
26054247 10.1016/j.bmc.2015.03.063 NON-PROTEIN TARGET 4
21936551 10.1021/jm200432a Histone deacetylase 1 4
25147612 10.1021/ml500170r HCT-116 4
25147612 10.1021/ml500170r ADMET 4
26331334 10.1021/acs.jmedchem.5b01044 ADMET 3
24900585 10.1021/ml400093y Retinoblastoma-associated protein 3
25203782 10.1016/j.ejmech.2014.09.009 Histone deacetylase 6 3
21936551 10.1021/jm200432a Histone deacetylase 6 3
21666868 10.1021/ml1002794 Unchecked 3
25203782 10.1016/j.ejmech.2014.09.009 Histone deacetylase 1 3

Data from ChEMBL 36 via Core Engine