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Compound Detail

CHEMBL4217594

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O=C(CCn1cnc([N+](=O)[O-])n1)Nc1ccc(Oc2ccc(Cl)cc2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4217594
Phase Preclinical
Structure Type MOL
InChI Key HWQAXYIDJKLSCZ-UHFFFAOYSA-N
7
Targets
17
Activities
1
Assay Types
0
PK Parameters
11
Publications
0
Known Names

Molecular Properties

387.8
MW (Da)
3.66
ALogP
7
HBA
1
HBD
112.2
PSA (Ų)
0.49
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C17H14ClN5O4
MW 387.78
Aromatic Rings 3
Heavy Atoms 27
NP-Likeness -1.90

Activity Summary

IC50 17 meas. best 8.3

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Trypanosoma cruzi
CHEMBL368
 IC50 8.3 8.3 5.0 1
Trypanosoma brucei rhodesiense
CHEMBL612348
 IC50 7.39 7.39 41.0 1
Trypanosoma brucei brucei
CHEMBL612851
 IC50 6.47 6.29 340.0 3
Leishmania donovani
CHEMBL367
 IC50 5.94 5.94 1154.0 1
Mycobacterium tuberculosis
CHEMBL360
 IC50 5.47 4.8063 3400.0 8
THP-1
CHEMBL614245
 IC50 4.85 4.85 14000.0 1
L6
CHEMBL614793
 IC50 4.77 4.765 17000.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Trypanosoma cruzi IC50 = 5.0 nM 8.3 Trypanocidal activity against Trypanosoma cruzi Tulahuen C4 amastigotes intra-pe... 27543881
Trypanosoma brucei rhodesiense IC50 = 41.0 nM 7.39 Antiprotozoal activity against Trypanosoma brucei rhodesiense STIB900 trypomasti... 27543881
Trypanosoma brucei brucei IC50 = 340.0 nM 6.47 Antiprotozoal activity against blood stream form of Trypanosoma brucei brucei as... 27543881
Trypanosoma brucei brucei IC50 = 620.0 nM 6.21 Antiprotozoal activity against blood stream form of Trypanosoma brucei brucei as... 27543881
Trypanosoma brucei brucei IC50 = 640.0 nM 6.19 Antiprotozoal activity against wild type blood stream form of Trypanosoma brucei... 27543881
Leishmania donovani IC50 = 1154.0 nM 5.94 Antiprotozoal activity against Leishmania donovani MHOM/ET/67/L82 alamar blue st... 27543881
Mycobacterium tuberculosis IC50 = 3400.0 nM 5.47 Antitubercular activity against luxABCDE expressing Mycobacterium tuberculosis H... 28993106
THP-1 IC50 = 14000.0 nM 4.85 Cytotoxicity against human THP1 cells after 3 days by luminescence assay 28993106
Mycobacterium tuberculosis IC50 = 15000.0 nM 4.82 Antitubercular activity against Mycobacterium tuberculosis H37Rv ATCC 27294 afte... 28993106
Mycobacterium tuberculosis IC50 = 15000.0 nM 4.82 Antitubercular activity against rifampicin-resistant Mycobacterium tuberculosis ... 28993106
L6 IC50 = 17000.0 nM 4.77 Cytotoxicity against rat L6 cells after 2 days by CellTiter-Glo luminescent cell... 28993106
Mycobacterium tuberculosis IC50 = 17000.0 nM 4.77 Antitubercular activity against rifampicin-resistant Mycobacterium tuberculosis ... 28993106
L6 IC50 = 17300.0 nM 4.76 Cytotoxicity against rat L6 cells assessed as reduction in cell viability by ala... 27543881
Mycobacterium tuberculosis IC50 = 18000.0 nM 4.75 Antitubercular activity against isoniazid-resistant Mycobacterium tuberculosis I... 28993106
Mycobacterium tuberculosis IC50 = 24000.0 nM 4.62 Antitubercular activity against fluoroquinolone-resistant Mycobacterium tubercul... 28993106
Mycobacterium tuberculosis IC50 = 25000.0 nM 4.6 Antitubercular activity against Mycobacterium tuberculosis H37Rv ATCC 27294 afte... 28993106
Mycobacterium tuberculosis IC50 = 25000.0 nM 4.6 Antitubercular activity against isoniazid-resistant Mycobacterium tuberculosis H... 28993106

Literature References

PubMed DOI Target Context # Activities
28993106 10.1016/j.bmc.2017.09.037 Mycobacterium tuberculosis 27
27543881 10.1016/j.ejmech.2016.08.002 Unchecked 5
27543881 10.1016/j.ejmech.2016.08.002 Trypanosoma cruzi 4
27543881 10.1016/j.ejmech.2016.08.002 Trypanosoma brucei brucei 3
27543881 10.1016/j.ejmech.2016.08.002 ADMET 2
28993106 10.1016/j.bmc.2017.09.037 THP-1 1
28993106 10.1016/j.bmc.2017.09.037 L6 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