CHEBI:63918 - artesunate

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ChEBI Name artesunate
ChEBI ID CHEBI:63918
Definition An artemisinin derivative that is the hemisuccinate ester of the lactol resulting from the reduction of the lactone carbonyl group of artemisinin. It is used, generally as the sodium salt, for the treatment of malaria.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C19H28O8
Net Charge 0
Average Mass 384.42080
Monoisotopic Mass 384.178
InChI InChI=1S/C19H28O8/c1-10-4-5-13-11(2)16(23-15(22)7-6-14(20)21)24-17-19(13)12(10)8-9-18(3,25-17)26-27-19/h10-13,16-17H,4-9H2,1-3H3,(H,20,21)/t10-,11-,12+,13+,16-,17-,18-,19-/m1/s1
InChIKey FIHJKUPKCHIPAT-AHIGJZGOSA-N
SMILES [H][C@@]12CC[C@@]3(C)OO[C@@]11[C@@]([H])(CC[C@H]2C)[C@@H](C)[C@H](OC(=O)CCC(O)=O)O[C@]1([H])O3
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(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.
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 artesunate (CHEBI:63918) has role antimalarial (CHEBI:38068)
artesunate (CHEBI:63918) is a artemisinin derivative (CHEBI:63920)
artesunate (CHEBI:63918) is a cyclic acetal (CHEBI:59770)
artesunate (CHEBI:63918) is a dicarboxylic acid monoester (CHEBI:36244)
artesunate (CHEBI:63918) is a hemisuccinate (CHEBI:138979)
artesunate (CHEBI:63918) is a semisynthetic derivative (CHEBI:72588)
artesunate (CHEBI:63918) is a sesquiterpenoid (CHEBI:26658)
IUPAC Name
4-oxo-4-{[(3R,5aS,6R,8aS,9R,10S,12R,12aR)-3,6,9-trimethyldecahydro-3,12-epoxypyrano[4,3-j][1,2]benzodioxepin-10-yl]oxy}butanoic acid
INNs Sources
artesunate ChemIDplus
artesunato ChemIDplus
artesunatum ChemIDplus
Synonyms Sources
artesunic acid ChemIDplus
AS ChEBI
butanedioic acid, 1-[(3R,5aS,6R,8aS,9R,10S,12R,12aR)-decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10-yl] ester NIST Chemistry WebBook
dihydroqinghasu hemsuccinate ChemIDplus
Manual Xrefs Databases
247 DrugCentral
Artesunate Wikipedia
D02482 KEGG DRUG
View more database links
Registry Numbers Types Sources
182824-33-5 CAS Registry Number ChemIDplus
6003212 Reaxys Registry Number Reaxys
88495-63-0 CAS Registry Number KEGG DRUG
88495-63-0 CAS Registry Number NIST Chemistry WebBook
88495-63-0 CAS Registry Number ChemIDplus
Last Modified
09 November 2017