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Compound Detail

CHEMBL5077168

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CCc1c(C(=O)Nc2cc(/C=C/C(=O)NO)ccc2OC)[nH]c(C)c1C(C)=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL5077168
Phase Preclinical
Structure Type MOL
InChI Key IMAQUYGNXCKZFP-VQHVLOKHSA-N
12
Targets
14
Activities
2
Assay Types
0
PK Parameters
16
Publications
0
Known Names

Molecular Properties

385.4
MW (Da)
2.87
ALogP
5
HBA
4
HBD
120.5
PSA (Ų)
0.25
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C20H23N3O5
MW 385.42
Aromatic Rings 2
Heavy Atoms 28
NP-Likeness -0.67

Activity Summary

IC50 8 meas. best 7.38
Kd 6 meas. best 5.53

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase 6
CHEMBL1865
 IC50 7.38 7.38 42.0 1
Histone deacetylase 3
CHEMBL1829
 IC50 6.92 6.92 119.0 1
Histone deacetylase 1
CHEMBL325
 IC50 6.75 6.75 179.0 1
Histone deacetylase 2
CHEMBL1937
 IC50 6.45 6.45 359.0 1
TALL-1
CHEMBL2366254
 IC50 5.54 5.54 2880.0 1
Bromodomain-containing protein 4
CHEMBL1163125
 Kd 5.53 5.53 2980.0 1
Bromodomain-containing protein 2
CHEMBL1293289
 Kd 5.48 5.305 3300.0 2
K562
CHEMBL385
 IC50 5.47 5.47 3400.0 1
Bromodomain-containing protein 3
CHEMBL1795186
 Kd 5.25 5.185 5650.0 2
HPBALL
CHEMBL4296435
 IC50 5.17 5.17 6790.0 1
HL-60
CHEMBL383
 IC50 5.11 5.11 7820.0 1
Bromodomain-containing protein 7
CHEMBL3085622
 Kd 5.07 5.07 8500.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase 6 IC50 = 42.0 nM 7.38 Inhibition of human recombinant HDAC6 assessed as fluorescence using fluorogenic... 34582215
Histone deacetylase 3 IC50 = 119.0 nM 6.92 Inhibition of human HDAC3 assessed as target activity using fluorogenic substrat... 34582215
Histone deacetylase 1 IC50 = 179.0 nM 6.75 Inhibition of human recombinant HDAC1 assessed as fluorescence using fluorogenic... 34582215
Histone deacetylase 2 IC50 = 359.0 nM 6.45 Inhibition of human HDAC2 assessed as target activity using fluorogenic substrat... 34582215
TALL-1 IC50 = 2880.0 nM 5.54 Anticancer activity against human TALL-1 cells assessed as cell growth inhibitio... 34582215
Bromodomain-containing protein 4 Kd = 2980.0 nM 5.53 Binding affinity to human BRD4 domain 1 (unknown origin) assessed as dissociatio... 34582215
Bromodomain-containing protein 2 Kd = 3300.0 nM 5.48 Binding affinity to human BRD2 domain 2 assessed as dissociation constant by iso... 34582215
K562 IC50 = 3400.0 nM 5.47 Anticancer activity against human K562 cells assessed as cell growth inhibition ... 34582215
Bromodomain-containing protein 3 Kd = 5650.0 nM 5.25 Binding affinity to human BRD3 domain 1 assessed as dissociation constant by iso... 34582215
HPBALL IC50 = 6790.0 nM 5.17 Anticancer activity against human HPBALL cells assessed as cell growth inhibitio... 34582215
Bromodomain-containing protein 2 Kd = 7400.0 nM 5.13 Binding affinity to human BRD2 domain 1 assessed as dissociation constant by iso... 34582215
Bromodomain-containing protein 3 Kd = 7550.0 nM 5.12 Binding affinity to human BRD3 domain 2 assessed as dissociation constant by iso... 34582215
HL-60 IC50 = 7820.0 nM 5.11 Anticancer activity against human HL-60 cells assessed as cell growth inhibition... 34582215
Bromodomain-containing protein 7 Kd = 8500.0 nM 5.07 Binding affinity to human BRD7 assessed as dissociation constant by isothermal t... 34582215

Literature References

PubMed DOI Target Context # Activities
34582215 10.1021/acs.jmedchem.1c01119 HPBALL 7
34582215 10.1021/acs.jmedchem.1c01119 Histone deacetylase 3
34582215 10.1021/acs.jmedchem.1c01119 Bromodomain-containing protein 3 2
34582215 10.1021/acs.jmedchem.1c01119 Bromodomain-containing protein 2 2
34582215 10.1021/acs.jmedchem.1c01119 HL-60 2
34582215 10.1021/acs.jmedchem.1c01119 TALL-1 2
34582215 10.1021/acs.jmedchem.1c01119 K562 2
34582215 10.1021/acs.jmedchem.1c01119 MOLT-4 1
34582215 10.1021/acs.jmedchem.1c01119 Bromodomain-containing protein 4 1
34582215 10.1021/acs.jmedchem.1c01119 Histone deacetylase 6 1
34582215 10.1021/acs.jmedchem.1c01119 Histone deacetylase 1 1
34582215 10.1021/acs.jmedchem.1c01119 Bromodomain-containing protein 7 1
34582215 10.1021/acs.jmedchem.1c01119 Histone deacetylase 2 1
34582215 10.1021/acs.jmedchem.1c01119 Histone deacetylase 3 1
34582215 10.1021/acs.jmedchem.1c01119 HAL-01 1
34582215 10.1021/acs.jmedchem.1c01119 REH 1

Data from ChEMBL 36 via Core Engine