artemisinin   Click here for help

GtoPdb Ligand ID: 9954

Synonyms: qinghaosu
Antimalarial Ligand
Comment: Artemisinin is a sesquiterpene lactone with an unusual endoperoxide bridge, believed to be responsible for the antimalarial activity of the compound. It is a natural product, isolated from the qinghao or sweet wormwood plant (Artemisia annua) and used in Chinese traditional medicine to treat fever.
Artemisinin is a prodrug that is converted to the active metabolite artenimol (dihydroartemisinin).
We show one representation of artemisinin here. As with other natural products, there are alternative chemical structures due to the complex stereochemistry.

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 0
Rotatable bonds 0
Topological polar surface area 53.99
Molecular weight 282.15
XLogP 3.04
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES O=C1OC2OC3(C)CCC4C2(C(C1C)CCC4C)OO3
Isomeric SMILES O=C1O[C@@H]2O[C@@]3(C)CC[C@@H]4[C@]2([C@H]([C@H]1C)CC[C@H]4C)OO3
InChI InChI=1S/C15H22O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-11,13H,4-7H2,1-3H3/t8-,9-,10+,11+,13-,14-,15-/m1/s1
InChI Key BLUAFEHZUWYNDE-NNWCWBAJSA-N
References
1. Delves M, Plouffe D, Scheurer C, Meister S, Wittlin S, Winzeler EA, Sinden RE, Leroy D. (2012)
The activities of current antimalarial drugs on the life cycle stages of Plasmodium: a comparative study with human and rodent parasites.
PLoS Med, 9 (2): e1001169. [PMID:22363211]
2. Duc DD, de Vries PJ, Nguyen XK, Le Nguyen B, Kager PA, van Boxtel CJ. (1994)
The pharmacokinetics of a single dose of artemisinin in healthy Vietnamese subjects.
Am J Trop Med Hyg, 51 (6): 785-90. [PMID:7810812]
3. Lynes EM, Bui M, Yap MC, Benson MD, Schneider B, Ellgaard L, Berthiaume LG, Simmen T. (2012)
Palmitoylated TMX and calnexin target to the mitochondria-associated membrane.
EMBO J, 31 (2): 457-70. [PMID:22045338]
4. Qiu N, Abegg D, Guidi M, Gilmore K, Seeberger PH, Adibekian A. (2021)
Artemisinin inhibits NRas palmitoylation by targeting the protein acyltransferase ZDHHC6.
Cell Chem Biol, [Epub ahead of print]. DOI: 10.1016/j.chembiol.2021.07.012 [PMID:34358442]
5. Tu Y. (2016)
Artemisinin-A Gift from Traditional Chinese Medicine to the World (Nobel Lecture).
Angew Chem Int Ed Engl, 55 (35): 10210-26. [PMID:27488942]
6. (2015)
Treatment of uncomplicated Plasmodium falciparum malaria.  In  Guidelines for the Treatment of Malaria. Third edition. (World Health Organization) . [PMID:26020088] [ISBN:9789241549127]