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Compound Detail

CHEMBL4209908

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

Basic Information

ChEMBL ID CHEMBL4209908
Phase Preclinical
Structure Type MOL
InChI Key BWAIMPAYVAKCTJ-UHFFFAOYSA-N
7
Targets
17
Activities
1
Assay Types
0
PK Parameters
11
Publications
0
Known Names

Molecular Properties

371.3
MW (Da)
3.15
ALogP
7
HBA
1
HBD
112.2
PSA (Ų)
0.50
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 C17H14FN5O4
MW 371.33
Aromatic Rings 3
Heavy Atoms 27
NP-Likeness -1.98

Activity Summary

IC50 17 meas. best 7.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Trypanosoma cruzi
CHEMBL368
 IC50 7.4 7.4 40.0 1
Trypanosoma brucei rhodesiense
CHEMBL612348
 IC50 6.78 6.78 167.0 1
Trypanosoma brucei brucei
CHEMBL612851
 IC50 6.48 6.2967 330.0 3
Leishmania donovani
CHEMBL367
 IC50 5.93 5.93 1175.0 1
Mycobacterium tuberculosis
CHEMBL360
 IC50 5.42 4.75 3800.0 8
THP-1
CHEMBL614245
 IC50 4.68 4.68 21000.0 1
L6
CHEMBL614793
 IC50 4.64 4.635 23000.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Trypanosoma cruzi IC50 = 40.0 nM 7.4 Trypanocidal activity against Trypanosoma cruzi Tulahuen C4 amastigotes intra-pe... 27543881
Trypanosoma brucei rhodesiense IC50 = 167.0 nM 6.78 Antiprotozoal activity against Trypanosoma brucei rhodesiense STIB900 trypomasti... 27543881
Trypanosoma brucei brucei IC50 = 330.0 nM 6.48 Antiprotozoal activity against blood stream form of Trypanosoma brucei brucei as... 27543881
Trypanosoma brucei brucei IC50 = 570.0 nM 6.24 Antiprotozoal activity against wild type blood stream form of Trypanosoma brucei... 27543881
Trypanosoma brucei brucei IC50 = 680.0 nM 6.17 Antiprotozoal activity against blood stream form of Trypanosoma brucei brucei as... 27543881
Leishmania donovani IC50 = 1175.0 nM 5.93 Antiprotozoal activity against Leishmania donovani MHOM/ET/67/L82 alamar blue st... 27543881
Mycobacterium tuberculosis IC50 = 3800.0 nM 5.42 Antitubercular activity against luxABCDE expressing Mycobacterium tuberculosis H... 28993106
Mycobacterium tuberculosis IC50 = 16000.0 nM 4.8 Antitubercular activity against rifampicin-resistant Mycobacterium tuberculosis ... 28993106
Mycobacterium tuberculosis IC50 = 19000.0 nM 4.72 Antitubercular activity against isoniazid-resistant Mycobacterium tuberculosis I... 28993106
THP-1 IC50 = 21000.0 nM 4.68 Cytotoxicity against human THP1 cells after 3 days by luminescence assay 28993106
Mycobacterium tuberculosis IC50 = 21000.0 nM 4.68 Antitubercular activity against rifampicin-resistant Mycobacterium tuberculosis ... 28993106
Mycobacterium tuberculosis IC50 = 22000.0 nM 4.66 Antitubercular activity against Mycobacterium tuberculosis H37Rv ATCC 27294 afte... 28993106
L6 IC50 = 23000.0 nM 4.64 Cytotoxicity against rat L6 cells after 2 days by CellTiter-Glo luminescent cell... 28993106
L6 IC50 = 23400.0 nM 4.63 Cytotoxicity against rat L6 cells assessed as reduction in cell viability by ala... 27543881
Mycobacterium tuberculosis IC50 = 25000.0 nM 4.6 Antitubercular activity against Mycobacterium tuberculosis H37Rv ATCC 27294 afte... 28993106
Mycobacterium tuberculosis IC50 = 26000.0 nM 4.58 Antitubercular activity against fluoroquinolone-resistant Mycobacterium tubercul... 28993106
Mycobacterium tuberculosis IC50 = 29000.0 nM 4.54 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
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
27543881 10.1016/j.ejmech.2016.08.002 ADMET 1

Data from ChEMBL 36 via Core Engine