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Compound Detail

CHEMBL218974

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C[C@]1(COc2ccc(OC(F)(F)F)cc2)Cn2cc([N+](=O)[O-])nc2O1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL218974
Phase Preclinical
Structure Type MOL
InChI Key GPWIINYCHXCGQH-CYBMUJFWSA-N
5
Targets
6
Activities
1
Assay Types
7
PK Parameters
20
Publications
0
Known Names

Molecular Properties

359.3
MW (Da)
2.92
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 -0.51

Activity Summary

IC50 6 meas. best 7.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Leishmania donovani
CHEMBL367
 IC50 7.52 7.52 30.0 1
Leishmania infantum
CHEMBL612848
 IC50 6.77 6.77 170.0 1
Trypanosoma cruzi
CHEMBL368
 IC50 5.58 5.58 2600.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 4.98 4.98 10500.0 2
Trypanosoma brucei
CHEMBL612849
 IC50 4.28 4.28 53000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 1390.0 ng.hr.mL-1 Mus musculus
AUC 15800.0 ng.hr.mL-1 Mus musculus
CL 11.0 mL.min-1.kg-1 Mus musculus
Cmax 3618.55 nM Mus musculus
F 91.0 % Mus musculus
T1/2 2.7 hr Mus musculus
Tmax 2.0 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Leishmania donovani IC50 = 30.0 nM 7.52 Antileishmanial activity against amastigote stage of Leishmania donovani infecte... 26901446
Leishmania infantum IC50 = 170.0 nM 6.77 Antileishmanial activity against amastigote stage of Leishmania infantum infecte... 26901446
Trypanosoma cruzi IC50 = 2600.0 nM 5.58 Antitrypanosomal activity against Trypanosoma cruzi infected in human MRC5 cells... 26901446
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 10500.0 nM 4.98 Inhibition of human ERG expressed in CHOK1 cells by patch clamp method 28459575
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 10500.0 nM 4.98 Inhibition of human ERG expressed in CHO cells by patch clamp method 33268145
Trypanosoma brucei IC50 = 53000.0 nM 4.28 Antitrypanosomal activity against trypomastigote stage of Trypanosoma brucei inc... 26901446

Literature References

PubMed DOI Target Context # Activities
26901446 10.1021/acs.jmedchem.5b01699 Leishmania infantum 10
26901446 10.1021/acs.jmedchem.5b01699 Mus musculus 9
26901446 10.1021/acs.jmedchem.5b01699 Leishmania donovani 8
17181168 10.1021/jm060957y Mycobacterium tuberculosis 6
28459575 10.1021/acs.jmedchem.7b00034 Salmonella typhimurium 4
29461823 10.1021/acs.jmedchem.7b01581 ADMET 3
33268145 10.1016/j.ejmech.2020.112914 ADMET 3
33268145 10.1016/j.ejmech.2020.112914 Leishmania donovani 3
29461823 10.1021/acs.jmedchem.7b01581 Plasma 3
26901446 10.1021/acs.jmedchem.5b01699 ADMET 3
26901446 10.1021/acs.jmedchem.5b01699 Mycobacterium tuberculosis 3
29461823 10.1021/acs.jmedchem.7b01581 Mycobacterium tuberculosis 2
28459575 10.1021/acs.jmedchem.7b00034 No relevant target 2
28459575 10.1021/acs.jmedchem.7b00034 ADMET 2
26901446 10.1021/acs.jmedchem.5b01699 Liver microsome 1
26901446 10.1021/acs.jmedchem.5b01699 Trypanosoma cruzi 1
26901446 10.1021/acs.jmedchem.5b01699 No relevant target 1
28463485 10.1021/acs.jmedchem.7b00143 Leishmania donovani 1
28459575 10.1021/acs.jmedchem.7b00034 Voltage-gated inwardly rectifying potassium channel KCNH2 1
26901446 10.1021/acs.jmedchem.5b01699 MRC5 1

Data from ChEMBL 36 via Core Engine