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Compound Detail

CHEMBL3098604

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Cc1cccc(NC(=O)[C@H](CCCCCC(=O)NO)NC(=O)[C@H]2CCC(=O)N2)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3098604
Phase Preclinical
Structure Type MOL
InChI Key DAGWCJGDWGPDPA-JKSUJKDBSA-N
15
Targets
21
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

404.5
MW (Da)
1.15
ALogP
5
HBA
5
HBD
136.6
PSA (Ų)
0.23
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 C20H28N4O5
MW 404.47
Aromatic Rings 1
Heavy Atoms 29
NP-Likeness -0.57

Activity Summary

IC50 21 meas. best 8.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase 6
CHEMBL1865
 IC50 8.52 8.52 3.0 2
Plasmodium falciparum
CHEMBL364
 IC50 8.22 8.22 6.0 1
Histone deacetylase 1
CHEMBL325
 IC50 8.15 8.15 7.0 2
Histone deacetylase 3
CHEMBL1829
 IC50 7.96 7.96 11.0 1
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2)
CHEMBL2111363
 IC50 7.96 7.96 11.0 1
Histone deacetylase 11
CHEMBL3310
 IC50 7.82 7.815 15.0 2
Histone deacetylase 2
CHEMBL1937
 IC50 7.57 7.57 27.0 2
Polyamine deacetylase HDAC10
CHEMBL5103
 IC50 7.52 7.52 30.0 2
Histone deacetylase 8
CHEMBL3192
 IC50 7.28 7.28 52.0 2
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 6.3 6.3 500.0 1
NCI-H460
CHEMBL396
 IC50 6.3 6.3 500.0 1
Trypanosoma cruzi
CHEMBL368
 IC50 6.07 6.07 849.0 1
L6
CHEMBL614793
 IC50 5.91 5.91 1232.0 1
Giardia intestinalis
CHEMBL612652
 IC50 5.33 5.33 4640.0 1
Trypanosoma brucei rhodesiense
CHEMBL612348
 IC50 5.26 5.26 5515.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase 6 IC50 = 3.0 nM 8.52 Inhibition of human HDAC6 using RHKK(Ac) as substrate by fluorimetric analysis 25563890
Histone deacetylase 6 IC50 = 3.0 nM 8.52 Inhibition of human HDAC6 using RHKK(Ac) as substrate by fluorimetric analysis 24345446
Plasmodium falciparum IC50 = 6.0 nM 8.22 Antiprotozoan activity against Plasmodium falciparum NF54 IEF forms 25563890
Histone deacetylase 1 IC50 = 7.0 nM 8.15 Inhibition of human HDAC1 using RHKK(Ac) as substrate by fluorimetric analysis 24345446
Histone deacetylase 1 IC50 = 7.0 nM 8.15 Inhibition of human HDAC1 using RHKK(Ac) as substrate by fluorimetric analysis 25563890
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2) IC50 = 11.0 nM 7.96 Inhibition of human HDAC3/NCOR2 using RHKK(Ac) as substrate by fluorimetric anal... 24345446
Histone deacetylase 3 IC50 = 11.0 nM 7.96 Inhibition of human HDAC3 using RHKK(Ac) as substrate by fluorimetric analysis 25563890
Histone deacetylase 11 IC50 = 15.0 nM 7.82 Inhibition of human HDAC11 using RHKK(Ac) as substrate by fluorimetric analysis 25563890
Histone deacetylase 11 IC50 = 15.5 nM 7.81 Inhibition of human HDAC11 using RHKK(Ac) as substrate by fluorimetric analysis 24345446
Histone deacetylase 2 IC50 = 27.0 nM 7.57 Inhibition of human HDAC2 using RHKK(Ac) as substrate by fluorimetric analysis 25563890
Histone deacetylase 2 IC50 = 27.0 nM 7.57 Inhibition of human HDAC2 using RHKK(Ac) as substrate by fluorimetric analysis 24345446
Polyamine deacetylase HDAC10 IC50 = 30.3 nM 7.52 Inhibition of human HDAC10 using RHKK(Ac) as substrate by fluorimetric analysis 24345446
Polyamine deacetylase HDAC10 IC50 = 30.0 nM 7.52 Inhibition of human HDAC10 using RHKK(Ac) as substrate by fluorimetric analysis 25563890
Histone deacetylase 8 IC50 = 52.0 nM 7.28 Inhibition of human HDAC8 using RHK(Ac)K(Ac) as substrate by fluorimetric analys... 24345446
Histone deacetylase 8 IC50 = 52.0 nM 7.28 Inhibition of human HDAC8 using RHK(Ac)K(Ac) as substrate by fluorimetric analys... 25563890
NON-PROTEIN TARGET IC50 = 500.0 nM 6.3 Cytotoxicity against human H460 cells 24345446
NCI-H460 IC50 = 500.0 nM 6.3 Cytotoxicity against human NCI-H460 cells 25563890
Trypanosoma cruzi IC50 = 849.0 nM 6.07 Antiprotozoan activity against Trypanosoma cruzi Tulahuen C4 amastigotes 25563890
L6 IC50 = 1232.0 nM 5.91 Cytotoxicity against rat L6 cells 25563890
Giardia intestinalis IC50 = 4640.0 nM 5.33 Antiprotozoan activity against Giardia lamblia G1 25563890

Literature References

PubMed DOI Target Context # Activities
25563890 10.1016/j.bmcl.2014.12.051 Plasmodium falciparum 2
25563890 10.1016/j.bmcl.2014.12.051 Histone deacetylase 3 1
25563890 10.1016/j.bmcl.2014.12.051 L6 1
25563890 10.1016/j.bmcl.2014.12.051 Leishmania donovani 1
25563890 10.1016/j.bmcl.2014.12.051 Trypanosoma cruzi 1
25563890 10.1016/j.bmcl.2014.12.051 Trypanosoma brucei rhodesiense 1
25563890 10.1016/j.bmcl.2014.12.051 NCI-H460 1
25563890 10.1016/j.bmcl.2014.12.051 Histone deacetylase 11 1
25563890 10.1016/j.bmcl.2014.12.051 Polyamine deacetylase HDAC10 1
25563890 10.1016/j.bmcl.2014.12.051 Histone deacetylase 8 1
25563890 10.1016/j.bmcl.2014.12.051 Histone deacetylase 6 1
24345446 10.1016/j.bmcl.2013.11.072 NON-PROTEIN TARGET 1
25563890 10.1016/j.bmcl.2014.12.051 Histone deacetylase 2 1
25563890 10.1016/j.bmcl.2014.12.051 Histone deacetylase 1 1
24345446 10.1016/j.bmcl.2013.11.072 Histone deacetylase 1 1
24345446 10.1016/j.bmcl.2013.11.072 Histone deacetylase 2 1
24345446 10.1016/j.bmcl.2013.11.072 Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2) 1
24345446 10.1016/j.bmcl.2013.11.072 Histone deacetylase 6 1
24345446 10.1016/j.bmcl.2013.11.072 Histone deacetylase 8 1
24345446 10.1016/j.bmcl.2013.11.072 Polyamine deacetylase HDAC10 1

Data from ChEMBL 36 via Core Engine