artemisinin   Click here for help

GtoPdb Ligand ID: 9954

Synonyms: qinghaosu
Antimalarial Ligand
Compound class: Natural product or derivative
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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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. Geng Y, Li W, Wong NK, Xue F, Li Q, Zhang Y, Xu J, Deng Z, Zhou Y. (2024)
Discovery of Artemisinins as Microsomal Prostaglandins Synthase-2 Inhibitors for the Treatment of Colorectal Cancer via Chemoproteomics.
J Med Chem, 67 (3): 2083-2094. [PMID:38287228]
4. Li W, Zhou Y, Tang G, Xiao Y. (2016)
Characterization of the Artemisinin Binding Site for Translationally Controlled Tumor Protein (TCTP) by Bioorthogonal Click Chemistry.
Bioconjug Chem, 27 (12): 2828-2833. [PMID:27998071]
5. 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]
6. Qiu N, Abegg D, Guidi M, Gilmore K, Seeberger PH, Adibekian A. (2022)
Artemisinin inhibits NRas palmitoylation by targeting the protein acyltransferase ZDHHC6.
Cell Chem Biol, 29 (3): 530-537.e7. [PMID:34358442]
7. Takusagawa F. (2013)
Microsomal prostaglandin E synthase type 2 (mPGES2) is a glutathione-dependent heme protein, and dithiothreitol dissociates the bound heme to produce active prostaglandin E2 synthase in vitro.
J Biol Chem, 288 (14): 10166-10175. [PMID:23426368]
8. 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]
9. Yamada T, Komoto J, Watanabe K, Ohmiya Y, Takusagawa F. (2005)
Crystal structure and possible catalytic mechanism of microsomal prostaglandin E synthase type 2 (mPGES-2).
J Mol Biol, 348 (5): 1163-76. [PMID:15854652]
10. Yamada T, Takusagawa F. (2007)
PGH2 degradation pathway catalyzed by GSH-heme complex bound microsomal prostaglandin E2 synthase type 2: the first example of a dual-function enzyme.
Biochemistry, 46 (28): 8414-24. [PMID:17585783]
11. (2015)
Treatment of uncomplicated Plasmodium falciparum malaria.  In  Guidelines for the Treatment of Malaria. Third edition. (World Health Organization) . [PMID:26020088] [ISBN:9789241549127]