artemisinin   Click here for help

GtoPdb Ligand ID: 9954

Synonyms: qinghaosu
Antimalarial Ligand
Compound class: Natural product
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.
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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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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Natural product
Ligand families/groups Antimalarial ligands
IUPAC Name Click here for help
(1R,4S,5R,8S,9R,12S,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-one
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
LIPID MAPS LMPR0103190003
PubChem CID 68827
Search Google for chemical match using the InChIKey BLUAFEHZUWYNDE-NNWCWBAJSA-N
Search Google for chemicals with the same backbone BLUAFEHZUWYNDE
Search PubMed clinical trials artemisinin
Search PubMed titles artemisinin
Search PubMed titles/abstracts artemisinin
UniChem Compound Search for chemical match using the InChIKey BLUAFEHZUWYNDE-NNWCWBAJSA-N
UniChem Connectivity Search for chemical match using the InChIKey BLUAFEHZUWYNDE-NNWCWBAJSA-N
Wikipedia Artemisinin