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Compound Detail

CHEMBL512244

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O=[N+]([O-])c1cn2c(n1)OC[C@H](OCc1ccc(OC(F)(F)F)cc1)C2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL512244
Phase Preclinical
Structure Type MOL
InChI Key ZLHZLMOSPGACSZ-LLVKDONJSA-N
6
Targets
10
Activities
2
Assay Types
0
PK Parameters
16
Publications
0
Known Names

Molecular Properties

359.3
MW (Da)
2.67
ALogP
7
HBA
0
HBD
88.7
PSA (Ų)
0.60
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C14H12F3N3O5
MW 359.26
Aromatic Rings 2
Heavy Atoms 25
NP-Likeness -0.63

Activity Summary

IC50 8 meas. best 6.8
EC50 2 meas. best 6.8

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Mycobacterium tuberculosis
CHEMBL360
 IC50 6.8 6.8 160.0 1
Leishmania donovani
CHEMBL367
 EC50 6.8 6.415 160.0 2
Trypanosoma cruzi
CHEMBL368
 IC50 6.4 6.4 400.0 1
Leishmania donovani
CHEMBL367
 IC50 6.27 6.27 540.0 1
Giardia intestinalis
CHEMBL612652
 IC50 5.5 5.5 3162.3 2
Leishmania infantum
CHEMBL612848
 IC50 5.33 5.33 4700.0 1
Entamoeba histolytica
CHEMBL612853
 IC50 5.3 5.29 5011.9 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Leishmania donovani EC50 = 160.0 nM 6.8 Antileishmanial activity against Leishmania donovani LV9 promastigotes after 72 ... 28463485
Mycobacterium tuberculosis IC50 = 160.0 nM 6.8 Anti-tubercular activity against Mycobacterium tuberculosis 26199118
Trypanosoma cruzi IC50 = 400.0 nM 6.4 Antitrypanosomal activity against Trypanosoma cruzi infected in human MRC5 cells... 29461823
Leishmania donovani IC50 = 540.0 nM 6.27 Antileishmanial activity against Leishmania donovani amastigotes after 72 hrs by... 29461823
Leishmania donovani EC50 = 930.0 nM 6.03 Antileishmanial activity against Leishmania donovani LV9 amastigotes infected in... 28463485
Giardia intestinalis IC50 = 3200.0 nM 5.5 Antiparasitic activity against Giardia lamblia WB trophozoites after 24 to 48 hr... 30468386
Giardia intestinalis IC50 = 3162.28 nM 5.5 Antiparasitic activity against Giardia lamblia WB trophozoites after 24 to 48 hr... 30468386
Leishmania infantum IC50 = 4700.0 nM 5.33 Antileishmanial activity against Leishmania infantum amastigotes infected in mou... 29461823
Entamoeba histolytica IC50 = 5011.87 nM 5.3 Antiparasitic activity against Entamoeba histolytica HM-1:IMSS trophozoites afte... 30468386
Entamoeba histolytica IC50 = 5300.0 nM 5.28 Antiparasitic activity against Entamoeba histolytica HM-1:IMSS trophozoites afte... 30468386

Literature References

PubMed DOI Target Context # Activities
19039139 10.1126/science.1164571 Mycobacterium tuberculosis 2
26199118 10.1016/j.bmcl.2015.06.060 Mycobacterium tuberculosis 2
29461823 10.1021/acs.jmedchem.7b01581 Leishmania donovani 2
29461823 10.1021/acs.jmedchem.7b01581 Liver 2
28463485 10.1021/acs.jmedchem.7b00143 Leishmania donovani 2
30468386 10.1021/acs.jmedchem.8b01578 Giardia intestinalis 2
30468386 10.1021/acs.jmedchem.8b01578 Entamoeba histolytica 2
19039139 10.1126/science.1164571 Deazaflavin-dependent nitroreductase 1
29461823 10.1021/acs.jmedchem.7b01581 Trypanosoma brucei 1
29461823 10.1021/acs.jmedchem.7b01581 MRC5 1
29461823 10.1021/acs.jmedchem.7b01581 Leishmania infantum 1
29461823 10.1021/acs.jmedchem.7b01581 Trypanosoma cruzi 1
29461823 10.1021/acs.jmedchem.7b01581 No relevant target 1
29461823 10.1021/acs.jmedchem.7b01581 ADMET 1
28463485 10.1021/acs.jmedchem.7b00143 Mycobacterium tuberculosis 1
30468386 10.1021/acs.jmedchem.8b01578 Clostridioides difficile 1

Data from ChEMBL 36 via Core Engine