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Compound Detail

CHEMBL3353927

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O=C1CC[C@H](C(=O)N[C@@H](CCCCCS)C(=O)Nc2cccc(C(F)(F)F)c2)N1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3353927
Phase Preclinical
Structure Type MOL
InChI Key CXRLQBYGPWEWJP-LSDHHAIUSA-N
12
Targets
19
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

431.5
MW (Da)
2.90
ALogP
4
HBA
4
HBD
87.3
PSA (Ų)
0.36
QED
0
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C19H24F3N3O3S
MW 431.48
Aromatic Rings 1
Heavy Atoms 29
NP-Likeness -0.79

Activity Summary

IC50 19 meas. best 8.3

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase 6
CHEMBL1865
 IC50 8.3 8.3 5.0 2
Histone deacetylase 1
CHEMBL325
 IC50 8.3 8.3 5.0 2
Polyamine deacetylase HDAC10
CHEMBL5103
 IC50 8.15 8.15 7.0 2
Histone deacetylase 3
CHEMBL1829
 IC50 7.96 7.96 11.0 2
Histone deacetylase 2
CHEMBL1937
 IC50 7.92 7.92 12.0 2
Histone deacetylase 11
CHEMBL3310
 IC50 7.36 7.36 44.0 2
Histone deacetylase 8
CHEMBL3192
 IC50 6.5 6.5 316.0 2
L6
CHEMBL614793
 IC50 5.57 5.57 2670.0 1
Plasmodium falciparum
CHEMBL364
 IC50 5.49 5.49 3260.0 1
Trypanosoma brucei rhodesiense
CHEMBL612348
 IC50 5.32 5.32 4750.0 1
Trypanosoma cruzi
CHEMBL368
 IC50 4.72 4.72 19100.0 1
Giardia intestinalis
CHEMBL612652
 IC50 4.19 4.19 64800.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase 6 IC50 = 5.0 nM 8.3 Inhibition of human HDAC6 using RHKK(Ac) as substrate by fluorimetric analysis 25563890
Histone deacetylase 1 IC50 = 5.0 nM 8.3 Inhibition of HDAC1 (unknown origin) using fluorogenic tetrapeptide RHKK(Ac) sub... 25233084
Histone deacetylase 6 IC50 = 5.0 nM 8.3 Inhibition of HDAC6 (unknown origin) using fluorogenic tetrapeptide RHKK(Ac) sub... 25233084
Histone deacetylase 1 IC50 = 5.0 nM 8.3 Inhibition of human HDAC1 using RHKK(Ac) as substrate by fluorimetric analysis 25563890
Polyamine deacetylase HDAC10 IC50 = 7.0 nM 8.15 Inhibition of human HDAC10 using RHKK(Ac) as substrate by fluorimetric analysis 25563890
Polyamine deacetylase HDAC10 IC50 = 7.0 nM 8.15 Inhibition of HDAC10 (unknown origin) using fluorogenic tetrapeptide RHKK(Ac) su... 25233084
Histone deacetylase 3 IC50 = 11.0 nM 7.96 Inhibition of human HDAC3 using RHKK(Ac) as substrate by fluorimetric analysis 25563890
Histone deacetylase 3 IC50 = 11.0 nM 7.96 Inhibition of HDAC3 (unknown origin) using fluorogenic tetrapeptide RHKK(Ac) sub... 25233084
Histone deacetylase 2 IC50 = 12.0 nM 7.92 Inhibition of HDAC2 (unknown origin) using fluorogenic tetrapeptide RHKK(Ac) sub... 25233084
Histone deacetylase 2 IC50 = 12.0 nM 7.92 Inhibition of human HDAC2 using RHKK(Ac) as substrate by fluorimetric analysis 25563890
Histone deacetylase 11 IC50 = 44.0 nM 7.36 Inhibition of human HDAC11 using RHKK(Ac) as substrate by fluorimetric analysis 25563890
Histone deacetylase 11 IC50 = 44.0 nM 7.36 Inhibition of HDAC11 (unknown origin) using fluorogenic tetrapeptide RHKK(Ac) su... 25233084
Histone deacetylase 8 IC50 = 316.0 nM 6.5 Inhibition of human HDAC8 using RHK(Ac)K(Ac) as substrate by fluorimetric analys... 25563890
Histone deacetylase 8 IC50 = 316.0 nM 6.5 Inhibition of HDAC8 (unknown origin) using fluorogenic tetrapeptide RHK(Ac)K(Ac)... 25233084
L6 IC50 = 2670.0 nM 5.57 Cytotoxicity against rat L6 cells 25563890
Plasmodium falciparum IC50 = 3260.0 nM 5.49 Antiprotozoan activity against Plasmodium falciparum NF54 IEF forms 25563890
Trypanosoma brucei rhodesiense IC50 = 4750.0 nM 5.32 Antiprotozoan activity against Trypanosoma brucei rhodesiense STIB 900 trypomast... 25563890
Trypanosoma cruzi IC50 = 19100.0 nM 4.72 Antiprotozoan activity against Trypanosoma cruzi Tulahuen C4 amastigotes 25563890
Giardia intestinalis IC50 = 64800.0 nM 4.19 Antiprotozoan activity against Giardia lamblia G1 25563890

Literature References

PubMed DOI Target Context # Activities
25563890 10.1016/j.bmcl.2014.12.051 Plasmodium falciparum 1
25233084 10.1021/jm5008209 Histone deacetylase 8 1
25233084 10.1021/jm5008209 Histone deacetylase 6 1
25233084 10.1021/jm5008209 Histone deacetylase 3 1
25233084 10.1021/jm5008209 Histone deacetylase 1 1
25233084 10.1021/jm5008209 Histone deacetylase 2 1
25233084 10.1021/jm5008209 Histone deacetylase 11 1
25233084 10.1021/jm5008209 Polyamine deacetylase HDAC10 1
25563890 10.1016/j.bmcl.2014.12.051 L6 1
25563890 10.1016/j.bmcl.2014.12.051 Giardia intestinalis 1
25563890 10.1016/j.bmcl.2014.12.051 Histone deacetylase 1 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 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
25563890 10.1016/j.bmcl.2014.12.051 Histone deacetylase 3 1
25563890 10.1016/j.bmcl.2014.12.051 Histone deacetylase 2 1

Data from ChEMBL 36 via Core Engine