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CHEBI:63918 - artesunate

Default Structure
ChEBI IDCHEBI:63918
ChEBI Nameartesunate
Stars
DefinitionAn 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.
Last Modified7 June 2021
SubmitterGareth Owen
DownloadsMolfile
FormulaC19H28O8
Net Charge0
Average Mass384.425
Monoisotopic Mass384.17842
SMILES[H][C@]12O[C@@H](OC(=O)CCC(=O)O)[C@H](C)[C@]3([H])CC[C@@H](C)[C@]4([H])CC[C@@](C)(OO[C@]143)O2
InChIInChI=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
InChIKeyFIHJKUPKCHIPAT-AHIGJZGOSA-N
Wikipedia
Roles Classification
Chemical Roles:
oxidising agent  A substance that removes electrons from another reactant in a redox reaction.
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
ferroptosis inducer  Any substance that induces or promotes ferroptosis (a type of programmed cell death dependent on iron and characterized by the accumulation of lipid peroxides) in organisms.
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.
Applications:
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.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
artesunate (CHEBI:63918) has role antimalarial (CHEBI:38068)
artesunate (CHEBI:63918) has role antineoplastic agent (CHEBI:35610)
artesunate (CHEBI:63918) has role ferroptosis inducer (CHEBI:173085)
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  Source
artesunateChemIDplus
artesunatoChemIDplus
artesunatumChemIDplus
Synonyms  Source
artesunic acidChemIDplus
ASChEBI
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] esterNIST Chemistry WebBook
dihydroqinghasu hemsuccinateChemIDplus
Manual XrefsDatabases
247DrugCentral
5293084ChemSpider
ArtesunateWikipedia
D02482KEGG DRUG
D95PDBeChem
DB09274DrugBank
HMDB0240267HMDB
Registry NumbersSources
Reaxys:6003212Reaxys
CAS:182824-33-5ChemIDplus
CAS:88495-63-0KEGG DRUG
CAS:88495-63-0ChemIDplus
CAS:88495-63-0NIST Chemistry WebBook
Citations