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Compound Detail

CHEMBL479432

FEBRIFUGINE
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O=C(C[C@@H]1NCCC[C@H]1O)Cn1cnc2ccccc2c1=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL479432
Name FEBRIFUGINE
Phase Preclinical
Structure Type MOL
InChI Key FWVHWDSCPKXMDB-LSDHHAIUSA-N
4
Targets
20
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

301.4
MW (Da)
0.47
ALogP
6
HBA
2
HBD
84.2
PSA (Ų)
0.86
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C16H19N3O3
MW 301.35
Aromatic Rings 2
Heavy Atoms 22
NP-Likeness 0.17

Activity Summary

EC50 10 meas. best 10.12
IC50 10 meas. best 8.8

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
 EC50 10.12 8.865 0.1 6
Plasmodium falciparum
CHEMBL364
 IC50 8.8 8.62 1.6 9
Hepatocyte
CHEMBL613289
 IC50 6.77 6.77 169.0 1
FM3A
CHEMBL614297
 EC50 6.77 6.77 170.0 3
Unchecked
CHEMBL612545
 EC50 6.16 6.16 700.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum EC50 = 0.076 nM 10.12 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum FCR-3 ... 24650700
Plasmodium falciparum EC50 = 0.7 nM 9.15 In vitro antimalarial activity against Plasmodium falciparum FCR3 13678413
Plasmodium falciparum EC50 = 0.7 nM 9.15 In vitro antimalarial activity against chloroquine-sensitive Plasmodium falcipar... 10447961
Plasmodium falciparum EC50 = 0.7 nM 9.15 Antimalarial activity against Plasmodium falciparum assessed as growth inhibitio... 24650700
Plasmodium falciparum EC50 = 1.2 nM 8.92 In vitro antimalarial activity against chloroquine-resistant Plasmodium falcipar... 10447961
Plasmodium falciparum IC50 = 1.6 nM 8.8 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum D6 16434194
Plasmodium falciparum IC50 = 1.6 nM 8.8 Antimalarial activity against Plasmodium falciparum PH3 infected in human A posi... 22182577
Plasmodium falciparum IC50 = 1.9 nM 8.72 Antimalarial activity against chloroquine-resistant Plasmodium falciparum W2 16434194
Plasmodium falciparum IC50 = 1.9 nM 8.72 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum 3D7 in... 22182577
Plasmodium falciparum IC50 = 2.0 nM 8.7 Antimalarial activity against chloroquine-resistant Plasmodium falciparum K1 inf... 22182577
Plasmodium falciparum IC50 = 2.1 nM 8.68 Antimalarial activity against Plasmodium falciparum Dd2 infected in human A posi... 22182577
Plasmodium falciparum IC50 = 3.1 nM 8.51 Antimalarial activity against chloroquine-resistant Plasmodium falciparum TM6 in... 22182577
Plasmodium falciparum IC50 = 4.2 nM 8.38 Antimalarial activity against chloroquine-resistant Plasmodium falciparum VS/1 i... 22182577
Plasmodium falciparum IC50 = 5.4 nM 8.27 Antimalarial activity against Plasmodium falciparum TM4 infected in human A posi... 22182577
FM3A EC50 = 170.0 nM 6.77 Compound was tested for cytotoxicity against FM3A mouse mammary cells. 10447961
FM3A EC50 = 170.0 nM 6.77 Cytotoxicity against FM3A mouse mammary cells 13678413
FM3A EC50 = 170.0 nM 6.77 In vitro cytotoxicity against mouse mammary FM3A cells 12036365
Hepatocyte IC50 = 169.0 nM 6.77 Cytotoxicity against rat hepatocytes 16434194
Plasmodium falciparum EC50 = 200.0 nM 6.7 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum FCR-3 ... 24650700
Unchecked EC50 = 700.0 nM 6.16 In vitro antimalarial activity against the Plasmodium falciparum FCR3 12036365

Literature References

PubMed DOI Target Context # Activities
22182577 10.1016/j.bmc.2011.11.053 Plasmodium falciparum 7
9644055 10.1021/np970433o Molecular identity unknown 4
9644055 10.1021/np970433o Macrophage 3
24650700 10.1016/j.bmc.2014.02.040 Plasmodium falciparum 3
10447961 10.1021/jm990131e Mus musculus 2
9644055 10.1021/np970433o Mus musculus 2
16854076 10.1021/jm0601809 Plasmodium falciparum 2
16854076 10.1021/jm0601809 L929 2
9644055 10.1021/np970433o ADMET 2
16434194 10.1016/j.bmcl.2006.01.009 Plasmodium falciparum 2
10447961 10.1021/jm990131e NON-PROTEIN TARGET 2
10447961 10.1021/jm990131e Plasmodium falciparum 2
13678413 10.1021/jm0302086 Plasmodium berghei 2
19467876 10.1016/j.bmc.2009.05.011 Plasmodium berghei 2
22182577 10.1016/j.bmc.2011.11.053 Plasmodium berghei 2
12036365 10.1021/jm010448q Plasmodium berghei 2
12036365 10.1021/jm010448q FM3A 2
10447961 10.1021/jm990131e FM3A 1
16434194 10.1016/j.bmcl.2006.01.009 Hepatocyte 1
24650700 10.1016/j.bmc.2014.02.040 Plasmodium berghei 1

Data from ChEMBL 36 via Core Engine