halofuginone   

GtoPdb Ligand ID: 10153

Compound class: Synthetic organic
Comment: Halofuginone is a synthetic derivative of febrifugine, a quinazolinone alkaloid first isolated from the roots of the blue evergreen hydrangea (D. febrifuga) and used as an antimalarial remedy in traditional Chinese medicine. The INN record for halofuginone indicates that it is a racemic mixture. We show the chemical structure without stereochemistry to represent the mixture.

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 4
Topological polar surface area 84.22
Molecular weight 413.01
XLogP 2.81
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES O=C(Cn1cnc2c(c1=O)cc(c(c2)Br)Cl)CC1NCCCC1O
Isomeric SMILES O=C(Cn1cnc2c(c1=O)cc(c(c2)Br)Cl)CC1NCCCC1O
InChI InChI=1S/C16H17BrClN3O3/c17-11-6-13-10(5-12(11)18)16(24)21(8-20-13)7-9(22)4-14-15(23)2-1-3-19-14/h5-6,8,14-15,19,23H,1-4,7H2
InChI Key LVASCWIMLIKXLA-UHFFFAOYSA-N
Whole organism assay data
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MOA/likely target Sp. Assay description Type Action Value Parameter Concentration range (M) Reference
Plasmodium falciparum proline--tRNA ligase PfDd2 Parasite growth inhibition assay - - 9.1 pEC50 - 1
pEC50 9.1 (EC50 8.1x10-10 M) SYBR Green assay [1]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Plasmodium falciparum proline--tRNA ligase Pf3D7 Parasite growth inhibition assay - - 9.1 pEC50 - 1
pEC50 9.1 (EC50 8.6x10-10 M) SYBR Green assay [1]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)