CHEBI:65989 - gutolactone

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ChEBI Name gutolactone
ChEBI ID CHEBI:65989
Definition A quassinoid isolated from Simaba guianensis and has been shown to exhibit antimalarial activity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C25H32O9
Net Charge 0
Average Mass 476.51620
Monoisotopic Mass 476.20463
InChI InChI=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
InChIKey WSUNNCJENRRPLS-DQVMPRLHSA-N
SMILES [H][C@@]12C[C@@]3([H])C(C)=CC(=O)[C@@H](O)[C@]3(C)[C@@]3([H])[C@@H](O)[C@H](O)[C@@]4(C)OC[C@@]13[C@@]4([H])[C@@H](OC(=O)C=C(C)C)C(=O)O2
Metabolite of Species Details
Simaba guianensis (NCBI:txid459152) Found in bark (BTO:0001301). See: PubMed
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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 via ChEBI Ontology
ChEBI Ontology
Outgoing 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 δ-lactone (CHEBI:18946)
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)
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 Number Type Source
152369-48-7 CAS Registry Number ChemIDplus
Citation Waiting for Citations Type Source
8289064 PubMed citation Europe PMC
Last Modified
06 February 2018