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
Classification
Compound class Synthetic organic
Ligand families/groups Antimalarial ligands
IUPAC Name
7-bromo-6-chloro-3-[3-(3-hydroxypiperidin-2-yl)-2-oxopropyl]quinazolin-4-one
International Nonproprietary Names
INN number INN
3676 halofuginone
Database Links
CAS Registry No. 55837-20-2 (source: Scifinder)
ChEMBL Ligand CHEMBL1197091
GtoPdb PubChem SID 381118863
PubChem CID 62894
RCSB PDB Ligand HFG
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SynPHARM 85927 (in complex with Plasmodium falciparum proline--tRNA ligase)