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(+)-artemisinin (CHEBI:223316)

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ChEBI Name (+)-artemisinin
ChEBI ID CHEBI:223316
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:8718
Supplier Information
See structure as:  Image  Applet
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Formula Source
C15H22O5 ChEBI
Net Charge 0
Average Mass 282.33220
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
InChIKey
BLUAFEHZUWYNDE-NNWCWBAJSA-N
SMILES
C[C@@H]1CC[C@H]2[C@@H](C)C(=O)O[C@@H]3O[C@@]4(C)CC[C@@H]1[C@@]23OO4
Roles Classification
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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.
Application(s): 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.
View more on the ChEBI Ontology
ChEBI Ontology
Outgoing (+)-artemisinin (CHEBI:223316) has role antimalarial (CHEBI:38068)
(+)-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 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 Sources
artemisinin ChemIDplus
artemisininum ChemIDplus
Synonyms Sources
1,5,9-trimethyl-(1R,4S,5R,9R,12S,13R)-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-one ChEMBL
arteannuin ChemIDplus
artemisinina ChemIDplus
artemisinine ChemIDplus
huanghuahaosu ChEBI
Octahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano(4,3-j)-1,2-benzodioxepin-10(3H)-one ChemIDplus
QHS ChEBI
Qing Hau Sau KEGG DRUG
Qinghaosu ChEBI
Qinghaosu ChemIDplus
Quing Hau Sau KEGG COMPOUND
Database Links Databases
Artemisinin Wikipedia
C00003359 KNApSAcK
C09538 KEGG COMPOUND
CPD-7561 MetaCyc
D02481 KEGG DRUG
LMPR0103190003 LIPID MAPS
View more database links
Registry Numbers Types Sources
1755493 Gmelin Registry Number Gmelin
4194670 Reaxys Registry Number Reaxys
4194670 Beilstein Registry Number Beilstein
63968-64-9 CAS Registry Number NIST Chemistry WebBook
63968-64-9 CAS Registry Number ChemIDplus
63968-64-9 CAS Registry Number KEGG DRUG
Citations Waiting for Citations Types Sources
15330155 PubMed citation CiteXplore
18008167 PubMed citation CiteXplore
19090980 PubMed citation CiteXplore
22174561 PubMed citation CiteXplore
7877142 PubMed citation ChEMBL
8544181 PubMed citation ChEMBL
Last Modified
28 julio 2014

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