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CHEBI:223316 - (+)-artemisinin

Default Structure
ChEBI IDCHEBI:223316
ChEBI Name(+)-artemisinin
Stars
DefinitionA sesquiterpene lactone obtained from sweet wormwood, Artemisia annua, which is used as an antimalarial for the treatment of multi-drug resistant strains of falciparum malaria.
Secondary ChEBI IDCHEBI:8718
Last Modified22 February 2017
DownloadsMolfile
FormulaC15H22O5
Net Charge0
Average Mass282.336
Monoisotopic Mass282.14672
SMILES[H][C@]12OC(=O)[C@H](C)[C@]3([H])CC[C@@H](C)[C@]4([H])CC[C@@](C)(OO[C@]143)O2
InChIInChI=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
InChIKeyBLUAFEHZUWYNDE-NNWCWBAJSA-N
Wikipedia
Roles Classification
Chemical Role:
oxidising agent  A substance that removes electrons from another reactant in a redox reaction.
Biological Roles:
antiviral agent  A substance that destroys or inhibits replication of viruses.
antimalarial  A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Applications:
antipsychotic agent  Antipsychotic drugs are agents that control agitated psychotic behaviour, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect.
antimalarial  A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
ChEBI Ontology
Outgoing Relation(s)
(+)-artemisinin (CHEBI:223316) has role antimalarial (CHEBI:38068)
(+)-artemisinin (CHEBI:223316) has role antipsychotic agent (CHEBI:35476)
(+)-artemisinin (CHEBI:223316) has role antiviral agent (CHEBI:22587)
(+)-artemisinin (CHEBI:223316) has role plant metabolite (CHEBI:76924)
(+)-artemisinin (CHEBI:223316) is a organic peroxide (CHEBI:25702)
(+)-artemisinin (CHEBI:223316) is a sesquiterpene lactone (CHEBI:37667)
Incoming Relation(s)
artemisinin derivative (CHEBI:63920) has functional parent (+)-artemisinin (CHEBI:223316)
IUPAC Name 
(3R,5aS,6R,8aS,9R,12S,12aR)-3,6,9-trimethyloctahydro-3,12-epoxypyrano[4,3-j][1,2]benzodioxepin-10(3H)-one
INNs  Source
artemisininChemIDplus
artemisininumChemIDplus
Synonyms  Source
1,5,9-trimethyl-(1R,4S,5R,9R,12S,13R)-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-oneChEMBL
arteannuinChemIDplus
artemisininChEMBL
artemisininaChemIDplus
artemisinineChemIDplus
GNF-PF-5341ChEMBL
Manual XrefsDatabases
3871DrugCentral
ArtemisininWikipedia
C00003359KNApSAcK
C09538KEGG COMPOUND
CPD-7561MetaCyc
D02481KEGG DRUG
LMPR0103190003LIPID MAPS
LSM-6546LINCS
Registry NumbersSources
Gmelin:1755493Gmelin
Reaxys:4194670Reaxys
CAS:63968-64-9KEGG DRUG
CAS:63968-64-9NIST Chemistry WebBook
CAS:63968-64-9ChemIDplus
CAS:63968-64-9KEGG COMPOUND
Citations