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Compound Detail

CHEMBL53153

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CCCN(CCC)c1c([N+](=O)[O-])cc(S(=O)(=O)Nc2ccccc2)cc1[N+](=O)[O-]

Basic Information

ChEMBL ID CHEMBL53153
Phase Preclinical
Structure Type MOL
InChI Key RMNVGONASFTVGC-UHFFFAOYSA-N
6
Targets
23
Activities
1
Assay Types
0
PK Parameters
15
Publications
0
Known Names

Molecular Properties

422.5
MW (Da)
3.93
ALogP
7
HBA
1
HBD
135.7
PSA (Ų)
0.45
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 C18H22N4O6S
MW 422.46
Aromatic Rings 2
Heavy Atoms 29
NP-Likeness -1.43

Activity Summary

IC50 23 meas. best 6.39

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Trypanosoma brucei
CHEMBL612849
IC50 6.39 6.39 410.0 1
Toxoplasma gondii
CHEMBL612888
IC50 5.33 4.9338 4700.0 13
Leishmania donovani
CHEMBL367
IC50 5.3 5.2 5000.0 5
Unchecked
CHEMBL612545
IC50 5.17 5.17 6700.0 1
J774
CHEMBL614123
IC50 4.55 4.55 28000.0 1
PC-3
CHEMBL390
IC50 4.51 4.51 31000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Trypanosoma brucei IC50 = 410.0 nM 6.39 Inhibitory concentration against brucei variant 221 was determined in vitro 15027874
Toxoplasma gondii IC50 = 4700.0 nM 5.33 Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin I2... 20145086
Leishmania donovani IC50 = 5000.0 nM 5.3 Inhibitory concentration against Leishmania donovani axenic amastigotes was dete... 15027874
Leishmania donovani IC50 = 5000.0 nM 5.3 Antimicrobial activity against Leishmania donovani 20185316
Leishmania donovani IC50 = 5000.35 nM 5.3 Antileishmanial activity against Leishmania donovani 20728249
Leishmania donovani IC50 = 5410.0 nM 5.27 Inhibitory activity against Leishmania donovani amastigotes 12161141
Unchecked IC50 = 6700.0 nM 5.17 Inhibition of Leishmanial tubulin assembly 15027874
Toxoplasma gondii IC50 = 6700.0 nM 5.17 Antimicrobial activity against Toxoplasma gondii infected in HFF after 8 days by... 20675138
Toxoplasma gondii IC50 = 6700.0 nM 5.17 Antimicrobial activity against Toxoplasma gondii RH infected in HFF cells by pla... 20145086
Toxoplasma gondii IC50 = 7700.0 nM 5.11 Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin I2... 20145086
Toxoplasma gondii IC50 = 9700.0 nM 5.01 Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin L1... 20145086
Toxoplasma gondii IC50 = 12400.0 nM 4.91 Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin S6... 20145086
Toxoplasma gondii IC50 = 12400.0 nM 4.91 Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin H2... 20145086
Toxoplasma gondii IC50 = 13300.0 nM 4.88 Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin R2... 20145086
Leishmania donovani IC50 = 14700.0 nM 4.83 Inhibitory activity against Leishmania donovani promastigotes 12161141
Toxoplasma gondii IC50 = 16900.0 nM 4.77 Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin I2... 20145086
Toxoplasma gondii IC50 = 17100.0 nM 4.77 Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin T2... 20145086
Toxoplasma gondii IC50 = 17000.0 nM 4.77 Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin R2... 20145086
Toxoplasma gondii IC50 = 17200.0 nM 4.76 Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin F2... 20145086
Toxoplasma gondii IC50 = 26200.0 nM 4.58 Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin V4... 20145086

Literature References

PubMed DOI Target Context # Activities
20145086 10.1128/aac.01150-09 Toxoplasma gondii 12
15027874 10.1021/jm0304461 Unchecked 2
15027874 10.1021/jm0304461 Mus musculus 2
12161141 10.1016/s0960-894x(02)00465-1 Leishmania donovani 2
15027874 10.1021/jm0304461 Leishmania donovani 1
15027874 10.1021/jm0304461 Trypanosoma brucei 1
15027874 10.1021/jm0304461 J774 1
15027874 10.1021/jm0304461 PC-3 1
15027874 10.1021/jm0304461 Tubulin 1
15027874 10.1021/jm0304461 ADMET 1
12161141 10.1016/s0960-894x(02)00465-1 Leishmania sp. 1
20185316 10.1016/j.bmc.2010.01.068 Leishmania donovani 1
20185316 10.1016/j.bmc.2010.01.068 Trypanosoma brucei brucei 1
20675138 10.1016/j.bmcl.2010.07.003 Toxoplasma gondii 1
20728249 10.1016/j.ejmech.2010.07.060 Leishmania donovani 1

Data from ChEMBL 36 via Core Engine