E209   Click here for help

GtoPdb Ligand ID: 10465

Antimalarial Ligand
Compound class: Synthetic organic
Comment: E209 is a fully synthetic tetraoxane analogue with potent antimalarial activity [1].

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
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Hydrogen bond acceptors 5
Hydrogen bond donors 0
Rotatable bonds 5
Topological polar surface area 49.39
Molecular weight 501.29
XLogP 6.88
No. Lipinski's rules broken 1
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Canonical SMILES FC1CCN(CC1)CCOc1ccc(cc1)C1CCC2(CC1)OOC1(OO2)C2CC3CC1CC(C2)C3
Isomeric SMILES FC1CCN(CC1)CCOc1ccc(cc1)C1CCC2(CC1)OOC1(OO2)C2CC3CC1CC(C2)C3
InChI InChI=1S/C29H40FNO5/c30-26-7-11-31(12-8-26)13-14-32-27-3-1-22(2-4-27)23-5-9-28(10-6-23)33-35-29(36-34-28)24-16-20-15-21(18-24)19-25(29)17-20/h1-4,20-21,23-26H,5-19H2
1. O'Neill PM, Amewu RK, Charman SA, Sabbani S, Gnädig NF, Straimer J, Fidock DA, Shore ER, Roberts NL, Wong MH et al.. (2017)
A tetraoxane-based antimalarial drug candidate that overcomes PfK13-C580Y dependent artemisinin resistance.
Nat Commun, 8: 15159. [PMID:28537265]