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Compound Detail

CHEMBL511749

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CC(C)(C)OC(=O)Nc1ccc(-c2cc(C(=O)NCCCCCCC(=O)NO)no2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL511749
Phase Preclinical
Structure Type MOL
InChI Key WWGBHDIHIVGYLZ-UHFFFAOYSA-N
18
Targets
39
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

446.5
MW (Da)
3.87
ALogP
7
HBA
4
HBD
142.8
PSA (Ų)
0.25
QED
0
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C22H30N4O6
MW 446.50
Aromatic Rings 2
Heavy Atoms 32
NP-Likeness -1.22

Activity Summary

IC50 39 meas. best 9.49

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase 6
CHEMBL1865
 IC50 9.49 8.014 0.3 5
Histone deacetylase 3
CHEMBL1829
 IC50 9.38 7.4067 0.4 3
Histone deacetylase 1
CHEMBL325
 IC50 8.49 6.9443 3.2 7
Histone deacetylase
CHEMBL2093865
 IC50 7.3 7.3 50.0 1
Polyamine deacetylase HDAC10
CHEMBL5103
 IC50 7.04 6.5467 90.7 3
Histone deacetylase 2
CHEMBL1937
 IC50 7.03 6.815 93.0 2
MIA PaCa-2
CHEMBL614725
 IC50 7.0 7.0 100.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 7.0 6.61 100.0 2
Unchecked
CHEMBL612545
 IC50 6.96 5.85 109.0 3
HuP-T3
CHEMBL1075477
 IC50 6.52 6.52 300.0 1
ADMET
CHEMBL612558
 IC50 6.3 6.3 500.0 1
HL-60
CHEMBL383
 IC50 6.23 6.23 594.0 1
Jurkat
CHEMBL397
 IC50 6.21 6.21 610.0 1
BXPC-3
CHEMBL614530
 IC50 6.0 6.0 1000.0 1
HCT-116
CHEMBL394
 IC50 5.83 5.83 1470.0 1
MCF7
CHEMBL387
 IC50 5.55 5.55 2820.0 1
Histone deacetylase 8
CHEMBL3192
 IC50 5.21 5.185 6210.0 2
B16-F10
CHEMBL612656
 IC50 5.03 5.03 9410.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase 6 IC50 = 0.326 nM 9.49 Inhibition of HDAC6 (unknown origin) using carboxyfluorescein (FAM)-labeled acet... 23627282
Histone deacetylase 3 IC50 = 0.42 nM 9.38 Inhibition of HDAC3 after 17 hrs 18642892
Histone deacetylase 1 IC50 = 3.2 nM 8.49 Inhibition of recombinant full length C-terminal His/FLAG tagged human HDAC1 (1 ... 31414801
Histone deacetylase 1 IC50 = 12.7 nM 7.9 Inhibition of HDAC1 (unknown origin) using carboxyfluorescein (FAM)-labeled acet... 23627282
Histone deacetylase 6 IC50 = 13.8 nM 7.86 Inhibition of recombinant N-terminal GST-tagged human HDAC6 (1 to 1215 residues)... 31414801
Histone deacetylase 6 IC50 = 18.0 nM 7.75 Inhibition of recombinant human N-terminal GST tagged HDAC6 expressed in baculov... 35043615
Histone deacetylase 6 IC50 = 27.0 nM 7.57 Inhibition of recombinant human HDAC6 using Ac-RHKK(Ac)-ACC as substrate by fluo... 20947351
Histone deacetylase 6 IC50 = 40.0 nM 7.4 Inhibition of recombinant human HDAC6 using Boc-Lys(Ac)-AMC as substrate by fluo... 20947351
Histone deacetylase IC50 = 50.0 nM 7.3 Inhibition of HDAC in human HeLa nuclear extracts using fluorometric substrate i... 35043615
Histone deacetylase 1 IC50 = 71.0 nM 7.15 Inhibition of recombinant human HDAC1 using fluorogenic RHKKAc peptide as substr... 20614936
Polyamine deacetylase HDAC10 IC50 = 90.7 nM 7.04 Inhibition of HDAC10 after 17 hrs 18642892
Histone deacetylase 2 IC50 = 93.0 nM 7.03 Inhibition of HDAC2 (unknown origin) using carboxyfluorescein (FAM)-labeled acet... 23627282
MIA PaCa-2 IC50 = 100.0 nM 7.0 Antiproliferative activity against human MiaPaca2 cells after 72 hrs by MTT assa... 18642892
NON-PROTEIN TARGET IC50 = 100.0 nM 7.0 Antiproliferative activity against human Panc04.03 cells after 72 hrs by MTT ass... 18642892
Unchecked IC50 = 109.0 nM 6.96 Inhibition of Class 1/2b HDAC in human HL-60 cells by HDAC-Glo assay 33360560
Histone deacetylase 3 IC50 = 190.0 nM 6.72 Inhibition of HDAC3 (unknown origin) using carboxyfluorescein (FAM)-labeled acet... 23627282
Histone deacetylase 2 IC50 = 252.0 nM 6.6 Inhibition of HDAC2 after 17 hrs 18642892
Histone deacetylase 1 IC50 = 260.0 nM 6.58 Inhibition of recombinant human HDAC1 expressed in baculovirus expression system... 35043615
Histone deacetylase 1 IC50 = 271.0 nM 6.57 Inhibition of HDAC1 after 17 hrs 18642892
HuP-T3 IC50 = 300.0 nM 6.52 Antiproliferative activity against human HupT3 cells after 72 hrs by MTT assay 18642892

Literature References

PubMed DOI Target Context # Activities
35043615 10.1021/acs.jmedchem.1c01863 Unchecked 3
35043615 10.1021/acs.jmedchem.1c01863 B16-F10 3
30964290 10.1021/acs.jmedchem.8b01936 Polyamine deacetylase HDAC10 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.6019/CHEMBL5724709 Fibroblast 2
- 10.6019/CHEMBL5724709 HEK-293T 2
35043615 10.1021/acs.jmedchem.1c01863 Histone deacetylase 2
18642892 10.1021/jm8002894 NON-PROTEIN TARGET 2
- 10.6019/CHEMBL5724709 U2OS 2
20947351 10.1016/j.bmcl.2010.09.100 Histone deacetylase 1 2
20947351 10.1016/j.bmcl.2010.09.100 Histone deacetylase 6 2
20947351 10.1016/j.bmcl.2010.09.100 Unchecked 2
18642892 10.1021/jm8002894 HMEC 1
23627282 10.1021/jm4001659 Histone deacetylase 1 1
23627282 10.1021/jm4001659 Histone deacetylase 2 1
- 10.6019/CHEMBL5724796 Bromodomain-containing protein 4 1
18642892 10.1021/jm8002894 HuP-T3 1
18642892 10.1021/jm8002894 Polyamine deacetylase HDAC10 1
18642892 10.1021/jm8002894 Histone deacetylase 6 1
18642892 10.1021/jm8002894 Histone deacetylase 3 1

Data from ChEMBL 36 via Core Engine