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Compound Detail

CHEMBL3098602

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O=C(CCCCC[C@H](NC(=O)[C@H]1CCC(=O)N1)C(=O)Nc1cccc(C(F)(F)F)c1)NO
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3098602
Phase Preclinical
Structure Type MOL
InChI Key XVGBJXUAVWXLJX-LSDHHAIUSA-N
15
Targets
21
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

458.4
MW (Da)
1.86
ALogP
5
HBA
5
HBD
136.6
PSA (Ų)
0.21
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 C20H25F3N4O5
MW 458.44
Aromatic Rings 1
Heavy Atoms 32
NP-Likeness -0.71

Activity Summary

IC50 21 meas. best 8.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase 3
CHEMBL1829
 IC50 8.7 8.7 2.0 1
Histone deacetylase 6
CHEMBL1865
 IC50 8.7 8.7 2.0 2
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2)
CHEMBL2111363
 IC50 8.7 8.7 2.0 1
Histone deacetylase 1
CHEMBL325
 IC50 8.7 8.7 2.0 2
Plasmodium falciparum
CHEMBL364
 IC50 8.52 8.52 3.0 1
Histone deacetylase 2
CHEMBL1937
 IC50 8.1 8.1 8.0 2
Polyamine deacetylase HDAC10
CHEMBL5103
 IC50 7.97 7.965 10.6 2
Histone deacetylase 8
CHEMBL3192
 IC50 7.48 7.48 32.9 2
Histone deacetylase 11
CHEMBL3310
 IC50 7.26 7.26 55.0 2
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 6.3 6.3 500.0 1
NCI-H460
CHEMBL396
 IC50 6.3 6.3 500.0 1
L6
CHEMBL614793
 IC50 6.2 6.2 638.0 1
Trypanosoma cruzi
CHEMBL368
 IC50 6.01 6.01 972.0 1
Trypanosoma brucei rhodesiense
CHEMBL612348
 IC50 5.38 5.38 4155.0 1
Giardia intestinalis
CHEMBL612652
 IC50 5.37 5.37 4270.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2) IC50 = 2.0 nM 8.7 Inhibition of human HDAC3/NCOR2 using RHKK(Ac) as substrate by fluorimetric anal... 24345446
Histone deacetylase 1 IC50 = 2.0 nM 8.7 Inhibition of human HDAC1 using RHKK(Ac) as substrate by fluorimetric analysis 24345446
Histone deacetylase 1 IC50 = 2.0 nM 8.7 Inhibition of human HDAC1 using RHKK(Ac) as substrate by fluorimetric analysis 25563890
Histone deacetylase 3 IC50 = 2.0 nM 8.7 Inhibition of human HDAC3 using RHKK(Ac) as substrate by fluorimetric analysis 25563890
Histone deacetylase 6 IC50 = 2.0 nM 8.7 Inhibition of human HDAC6 using RHKK(Ac) as substrate by fluorimetric analysis 25563890
Histone deacetylase 6 IC50 = 2.0 nM 8.7 Inhibition of human HDAC6 using RHKK(Ac) as substrate by fluorimetric analysis 24345446
Plasmodium falciparum IC50 = 3.0 nM 8.52 Antiprotozoan activity against Plasmodium falciparum NF54 IEF forms 25563890
Histone deacetylase 2 IC50 = 8.0 nM 8.1 Inhibition of human HDAC2 using RHKK(Ac) as substrate by fluorimetric analysis 24345446
Histone deacetylase 2 IC50 = 8.0 nM 8.1 Inhibition of human HDAC2 using RHKK(Ac) as substrate by fluorimetric analysis 25563890
Polyamine deacetylase HDAC10 IC50 = 10.6 nM 7.97 Inhibition of human HDAC10 using RHKK(Ac) as substrate by fluorimetric analysis 24345446
Polyamine deacetylase HDAC10 IC50 = 11.0 nM 7.96 Inhibition of human HDAC10 using RHKK(Ac) as substrate by fluorimetric analysis 25563890
Histone deacetylase 8 IC50 = 32.9 nM 7.48 Inhibition of human HDAC8 using RHK(Ac)K(Ac) as substrate by fluorimetric analys... 24345446
Histone deacetylase 8 IC50 = 33.0 nM 7.48 Inhibition of human HDAC8 using RHK(Ac)K(Ac) as substrate by fluorimetric analys... 25563890
Histone deacetylase 11 IC50 = 55.5 nM 7.26 Inhibition of human HDAC11 using RHKK(Ac) as substrate by fluorimetric analysis 24345446
Histone deacetylase 11 IC50 = 55.0 nM 7.26 Inhibition of human HDAC11 using RHKK(Ac) as substrate by fluorimetric analysis 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
L6 IC50 = 638.0 nM 6.2 Cytotoxicity against rat L6 cells 25563890
Trypanosoma cruzi IC50 = 972.0 nM 6.01 Antiprotozoan activity against Trypanosoma cruzi Tulahuen C4 amastigotes 25563890
Trypanosoma brucei rhodesiense IC50 = 4155.0 nM 5.38 Antiprotozoan activity against Trypanosoma brucei rhodesiense STIB 900 trypomast... 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