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CHEBI:65989 - gutolactone

ChEBI IDCHEBI:65989
ChEBI Namegutolactone
Stars
DefinitionA quassinoid isolated from Simaba guianensis and has been shown to exhibit antimalarial activity.
Last Modified6 February 2018
DownloadsMolfile
FormulaC25H32O9
Net Charge0
Average Mass476.522
Monoisotopic Mass476.20463
SMILES[H][C@]12[C@@H](O)[C@H](O)[C@@]3(C)OC[C@]14[C@@]3([H])[C@@H](OC(=O)C=C(C)C)C(=O)O[C@]4([H])C[C@@]1([H])C(C)=CC(=O)[C@@H](O)[C@]21C
InChIInChI=1S/C25H32O9/c1-10(2)6-15(27)34-17-19-24(5)21(30)16(28)18-23(4)12(11(3)7-13(26)20(23)29)8-14(33-22(17)31)25(18,19)9-32-24/h6-7,12,14,16-21,28-30H,8-9H2,1-5H3/t12-,14+,16+,17+,18+,19-,20+,21-,23-,24-,25+/m0/s1
InChIKeyWSUNNCJENRRPLS-DQVMPRLHSA-N
Species of MetaboliteComponentSourceComments
Simaba guianensis (ncbitaxon:459152) bark (BTO:0001301) PubMed (8289064)
Roles Classification
Biological Roles:
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.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
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)
gutolactone (CHEBI:65989) has functional parent 3-methylbut-2-enoic acid (CHEBI:37127)
gutolactone (CHEBI:65989) has role antimalarial (CHEBI:38068)
gutolactone (CHEBI:65989) has role metabolite (CHEBI:25212)
gutolactone (CHEBI:65989) is a cyclic ether (CHEBI:37407)
gutolactone (CHEBI:65989) is a enoate ester (CHEBI:51702)
gutolactone (CHEBI:65989) is a enone (CHEBI:51689)
gutolactone (CHEBI:65989) is a organic heteropentacyclic compound (CHEBI:38164)
gutolactone (CHEBI:65989) is a quassinoid (CHEBI:72485)
gutolactone (CHEBI:65989) is a secondary α-hydroxy ketone (CHEBI:2468)
gutolactone (CHEBI:65989) is a triol (CHEBI:27136)
gutolactone (CHEBI:65989) is a δ-lactone (CHEBI:18946)
IUPAC Name 
(1β,11β,12α,13β,15β)-1,11,12-trihydroxy-2,16-dioxo-13,20-epoxypicras-3-en-15-yl 3-methylbut-2-enoate
Registry NumbersSources
CAS:152369-48-7ChemIDplus
Citations