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Compound Detail

CHEMBL4202551

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O=C(CCn1cnc([N+](=O)[O-])n1)Nc1cccc(OCc2ccccc2)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4202551
Phase Preclinical
Structure Type MOL
InChI Key WSFYJUZUNNZGLH-UHFFFAOYSA-N
6
Targets
16
Activities
1
Assay Types
5
PK Parameters
13
Publications
0
Known Names

Molecular Properties

367.4
MW (Da)
2.79
ALogP
7
HBA
1
HBD
112.2
PSA (Ų)
0.48
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C18H17N5O4
MW 367.37
Aromatic Rings 3
Heavy Atoms 27
NP-Likeness -1.98

Activity Summary

IC50 16 meas. best 7.34

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Trypanosoma cruzi
CHEMBL368
 IC50 7.34 7.34 46.0 1
Trypanosoma brucei rhodesiense
CHEMBL612348
 IC50 6.66 6.66 221.0 1
Trypanosoma brucei brucei
CHEMBL612851
 IC50 6.44 5.7467 360.0 3
Leishmania donovani
CHEMBL367
 IC50 5.94 5.94 1139.0 1
Mycobacterium tuberculosis
CHEMBL360
 IC50 5.89 5.5088 1300.0 8
L6
CHEMBL614793
 IC50 4.4 4.4 40000.0 2

Pharmacokinetic Data

Parameter Value Units Species
CL 18.7 mL.min-1.g-1 Homo sapiens
CL 12.8 mL.min-1.g-1 Homo sapiens
Fu 0.042 - Homo sapiens
T1/2 2.067 hr Homo sapiens
T1/2 3.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Trypanosoma cruzi IC50 = 46.0 nM 7.34 Trypanocidal activity against Trypanosoma cruzi Tulahuen C4 amastigotes intra-pe... 27543881
Trypanosoma brucei rhodesiense IC50 = 221.0 nM 6.66 Antiprotozoal activity against Trypanosoma brucei rhodesiense STIB900 trypomasti... 27543881
Trypanosoma brucei brucei IC50 = 360.0 nM 6.44 Antiprotozoal activity against blood stream form of Trypanosoma brucei brucei as... 27543881
Leishmania donovani IC50 = 1139.0 nM 5.94 Antiprotozoal activity against Leishmania donovani MHOM/ET/67/L82 alamar blue st... 27543881
Mycobacterium tuberculosis IC50 = 1300.0 nM 5.89 Antitubercular activity against luxABCDE expressing Mycobacterium tuberculosis H... 28993106
Mycobacterium tuberculosis IC50 = 1700.0 nM 5.77 Antitubercular activity against Mycobacterium tuberculosis H37Rv ATCC 27294 afte... 28993106
Mycobacterium tuberculosis IC50 = 2200.0 nM 5.66 Antitubercular activity against rifampicin-resistant Mycobacterium tuberculosis ... 28993106
Mycobacterium tuberculosis IC50 = 3200.0 nM 5.5 Antitubercular activity against isoniazid-resistant Mycobacterium tuberculosis I... 28993106
Mycobacterium tuberculosis IC50 = 3400.0 nM 5.47 Antitubercular activity against fluoroquinolone-resistant Mycobacterium tubercul... 28993106
Trypanosoma brucei brucei IC50 = 3700.0 nM 5.43 Antiprotozoal activity against blood stream form of Trypanosoma brucei brucei as... 27543881
Mycobacterium tuberculosis IC50 = 4100.0 nM 5.39 Antitubercular activity against rifampicin-resistant Mycobacterium tuberculosis ... 28993106
Trypanosoma brucei brucei IC50 = 4250.0 nM 5.37 Antiprotozoal activity against wild type blood stream form of Trypanosoma brucei... 27543881
Mycobacterium tuberculosis IC50 = 4500.0 nM 5.35 Antitubercular activity against isoniazid-resistant Mycobacterium tuberculosis H... 28993106
Mycobacterium tuberculosis IC50 = 9200.0 nM 5.04 Antitubercular activity against Mycobacterium tuberculosis H37Rv ATCC 27294 afte... 28993106
L6 IC50 = 40000.0 nM 4.4 Cytotoxicity against rat L6 cells after 2 days by CellTiter-Glo luminescent cell... 28993106
L6 IC50 = 40200.0 nM 4.4 Cytotoxicity against rat L6 cells assessed as reduction in cell viability by ala... 27543881

Literature References

PubMed DOI Target Context # Activities
28993106 10.1016/j.bmc.2017.09.037 Mycobacterium tuberculosis 27
28993106 10.1016/j.bmc.2017.09.037 ADMET 12
27543881 10.1016/j.ejmech.2016.08.002 Unchecked 5
27543881 10.1016/j.ejmech.2016.08.002 Trypanosoma brucei brucei 3
27543881 10.1016/j.ejmech.2016.08.002 Trypanosoma cruzi 2
28993106 10.1016/j.bmc.2017.09.037 THP-1 1
28993106 10.1016/j.bmc.2017.09.037 L6 1
28993106 10.1016/j.bmc.2017.09.037 HepG2 1
28993106 10.1016/j.bmc.2017.09.037 Unchecked 1
27543881 10.1016/j.ejmech.2016.08.002 L6 1
27543881 10.1016/j.ejmech.2016.08.002 Leishmania donovani 1
27543881 10.1016/j.ejmech.2016.08.002 Trypanosoma brucei rhodesiense 1
27543881 10.1016/j.ejmech.2016.08.002 No relevant target 1

Data from ChEMBL 36 via Core Engine