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Compound Detail

CHEMBL4550522

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O=C(/C=C/c1ccc(NC(=O)Cc2cccc3ccccc23)cn1)NO
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4550522
Phase Preclinical
Structure Type MOL
InChI Key DTNVLAIWDVXDJR-ZHACJKMWSA-N
24
Targets
30
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

347.4
MW (Da)
2.93
ALogP
4
HBA
3
HBD
91.3
PSA (Ų)
0.38
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C20H17N3O3
MW 347.37
Aromatic Rings 3
Heavy Atoms 26
NP-Likeness -1.22

Activity Summary

IC50 30 meas. best 7.99

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
 IC50 7.99 7.8933 10.2 3
Histone deacetylase 6
CHEMBL1865
 IC50 7.82 7.82 15.0 2
Histone deacetylase 3
CHEMBL1829
 IC50 7.41 7.41 39.0 1
Histone deacetylase 8
CHEMBL3192
 IC50 7.33 7.33 47.0 1
K562
CHEMBL385
 IC50 7.3 7.3 50.0 1
MV4-11
CHEMBL613835
 IC50 7.23 7.23 59.0 1
Kasumi 1
CHEMBL613988
 IC50 7.18 7.18 66.0 1
HCT-116
CHEMBL394
 IC50 7.16 7.16 70.0 1
Polyamine deacetylase HDAC10
CHEMBL5103
 IC50 7.15 7.15 71.0 1
NB-4
CHEMBL614188
 IC50 7.08 7.08 84.0 1
Histone deacetylase 1
CHEMBL325
 IC50 7.01 7.005 98.0 2
Unchecked
CHEMBL612545
 IC50 6.92 6.81 120.0 2
Histone deacetylase 2
CHEMBL1937
 IC50 6.81 6.81 156.0 1
U-937
CHEMBL612794
 IC50 6.59 6.59 258.0 1
HL-60
CHEMBL383
 IC50 6.56 6.56 276.0 1
A549
CHEMBL392
 IC50 6.5 6.5 320.0 1
OCI-AML2
CHEMBL2366220
 IC50 6.42 6.42 379.0 1
KARPAS-299
CHEMBL2366156
 IC50 6.4 6.4 400.0 1
OCI-AML-3
CHEMBL4296479
 IC50 6.28 6.28 529.0 1
Histone deacetylase 5
CHEMBL2563
 IC50 5.87 5.87 1350.0 1
Histone deacetylase 7
CHEMBL2716
 IC50 5.69 5.69 2060.0 1
Histone deacetylase 4
CHEMBL3524
 IC50 5.57 5.565 2700.0 2
Histone deacetylase 9
CHEMBL4145
 IC50 5.55 5.55 2790.0 1
Histone deacetylase 11
CHEMBL3310
 IC50 5.4 5.4 3980.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum IC50 = 10.2 nM 7.99 Antiplasmodial activity against asynchronous form of Plasmodium falciparum 3D7 i... 30366254
Plasmodium falciparum IC50 = 13.5 nM 7.87 Antiplasmodial activity against Plasmodium falciparum Dd2 infected in human eryt... 30366254
Histone deacetylase 6 IC50 = 15.0 nM 7.82 Inhibition of recombinant human HDAC6 using RHK-K(Ac) as substrate by homogeneou... 30366254
Plasmodium falciparum IC50 = 15.3 nM 7.82 Antiplasmodial activity against asynchronous form of Plasmodium falciparum W2 in... 30366254
Histone deacetylase 6 IC50 = 15.0 nM 7.82 Inhibition of human recombinant HDAC6 using fluorogenic p53 (379-382 residues) (... 36549114
Histone deacetylase 3 IC50 = 39.0 nM 7.41 Inhibition of human recombinant HDAC3 using fluorogenic p53 (379-382 residues) (... 36549114
Histone deacetylase 8 IC50 = 47.0 nM 7.33 Inhibition of human recombinant HDAC8 using fluorogenic diacetylated p53 (379-38... 36549114
K562 IC50 = 50.0 nM 7.3 Antiproliferative activity against human K562 cells incubated for 72 hrs by Cell... 36549114
MV4-11 IC50 = 59.0 nM 7.23 Antiproliferative activity against human MV4-11 cells incubated for 48 hrs 36549114
Kasumi 1 IC50 = 66.0 nM 7.18 Antiproliferative activity against human Kasumi 1 cells incubated for 48 hrs 36549114
HCT-116 IC50 = 70.0 nM 7.16 Antiproliferative activity against human HCT-116 cells incubated for 72 hrs by C... 36549114
Polyamine deacetylase HDAC10 IC50 = 71.0 nM 7.15 Inhibition of human recombinant HDAC10 using fluorogenic p53 (379-382 residues) ... 36549114
NB-4 IC50 = 84.0 nM 7.08 Antiproliferative activity against human NB4 cells incubated for 48 hrs 36549114
Histone deacetylase 1 IC50 = 98.0 nM 7.01 Inhibition of human recombinant HDAC1 using fluorogenic p53 (379-382 residues) (... 36549114
Histone deacetylase 1 IC50 = 100.0 nM 7.0 Inhibition of recombinant human HDAC1 using RHK-K(Ac) as substrate by homogeneou... 30366254
Unchecked IC50 = 120.0 nM 6.92 Cytotoxicity against mouse spleen cells 30366254
Histone deacetylase 2 IC50 = 156.0 nM 6.81 Inhibition of human recombinant HDAC2 using fluorogenic p53 (379-382 residues) (... 36549114
Unchecked IC50 = 198.0 nM 6.7 Antiproliferative activity against human IMS-M2 cells incubated for 48 hrs 36549114
U-937 IC50 = 258.0 nM 6.59 Antiproliferative activity against human U-937 cells incubated for 48 hrs 36549114
HL-60 IC50 = 276.0 nM 6.56 Antiproliferative activity against human HL-60 cells incubated for 48 hrs 36549114

Literature References

PubMed DOI Target Context # Activities
36549114 10.1016/j.ejmech.2022.115022 Unchecked 21
36549114 10.1016/j.ejmech.2022.115022 U-937 5
30366254 10.1016/j.ejmech.2018.10.041 Plasmodium falciparum 4
30366254 10.1016/j.ejmech.2018.10.041 Unchecked 3
36549114 10.1016/j.ejmech.2022.115022 K562 2
36549114 10.1016/j.ejmech.2022.115022 Histone deacetylase 8 1
36549114 10.1016/j.ejmech.2022.115022 NB-4 1
36549114 10.1016/j.ejmech.2022.115022 Histone deacetylase 11 1
36549114 10.1016/j.ejmech.2022.115022 Polyamine deacetylase HDAC10 1
36549114 10.1016/j.ejmech.2022.115022 Histone deacetylase 9 1
36549114 10.1016/j.ejmech.2022.115022 Histone deacetylase 7 1
36549114 10.1016/j.ejmech.2022.115022 Histone deacetylase 5 1
36549114 10.1016/j.ejmech.2022.115022 Histone deacetylase 2 1
30366254 10.1016/j.ejmech.2018.10.041 Histone deacetylase 1 1
36549114 10.1016/j.ejmech.2022.115022 Histone deacetylase 6 1
36549114 10.1016/j.ejmech.2022.115022 Histone deacetylase 4 1
36549114 10.1016/j.ejmech.2022.115022 Histone deacetylase 3 1
36549114 10.1016/j.ejmech.2022.115022 Histone deacetylase 1 1
30366254 10.1016/j.ejmech.2018.10.041 HFF 1
30366254 10.1016/j.ejmech.2018.10.041 Histone deacetylase 6 1

Data from ChEMBL 36 via Core Engine