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
Classification Click here for help
Compound class Natural product or derivative
Ligand families/groups Antimalarial ligands
International Nonproprietary Names Click here for help
INN number INN
5954 artemisinin
Synonyms Click here for help
qinghaosu
Database Links Click here for help
CAS Registry No. 63968-64-9 (source: Scifinder)
ChEBI CHEBI:223316
ChEMBL Ligand CHEMBL269671
DrugCentral Ligand 3871
GtoPdb PubChem SID 374883841
PubChem CID 68827
Search Google for chemical match using the InChIKey BLUAFEHZUWYNDE-NNWCWBAJSA-N
Search Google for chemicals with the same backbone BLUAFEHZUWYNDE
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Search UniChem for chemical match using the InChIKey BLUAFEHZUWYNDE-NNWCWBAJSA-N
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Wikipedia Artemisinin

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Tocris
Artemisinin
Cat. No. 2668