CHEBI:223316 - (+)-artemisinin

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
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 No supplier information found for this compound.
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Wikipedia License
Creatine ( or ) is an organic compound with the nominal formula (H2N)(HN)CN(CH3)CH2CO2H. It exists in various tautomers in solutions (among which are neutral form and various zwitterionic forms). Creatine is found in vertebrates, where it facilitates recycling of adenosine triphosphate (ATP), primarily in muscle and brain tissue. Recycling is achieved by converting adenosine diphosphate (ADP) back to ATP via donation of phosphate groups. Creatine also acts as a buffer.
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Formula C15H22O5
Net Charge 0
Average Mass 282.33220
Monoisotopic Mass 282.14672
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
Chemical Role(s): oxidising agent
A substance that removes electrons from another reactant in a redox reaction.
(via peroxides )
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.
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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 ChemIDplus
Qinghaosu ChEBI
Quing Hau Sau KEGG COMPOUND
Manual Xrefs Databases
3871 DrugCentral
Artemisinin Wikipedia
C00003359 KNApSAcK
C09538 KEGG COMPOUND
CPD-7561 MetaCyc
D02481 KEGG DRUG
LMPR0103190003 LIPID MAPS
LSM-6546 LINCS
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Registry Numbers Types Sources
1755493 Gmelin Registry Number Gmelin
4194670 Reaxys Registry Number Reaxys
63968-64-9 CAS Registry Number KEGG COMPOUND
63968-64-9 CAS Registry Number KEGG DRUG
63968-64-9 CAS Registry Number NIST Chemistry WebBook
63968-64-9 CAS Registry Number ChemIDplus
Citations Types Sources
15330155 PubMed citation Europe PMC
18008167 PubMed citation Europe PMC
19090980 PubMed citation Europe PMC
22174561 PubMed citation Europe PMC
7877142 PubMed citation ChEMBL
8544181 PubMed citation ChEMBL
Last Modified
22 February 2017