CHEBI:65529 - bruceolide

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ChEBI Name bruceolide
ChEBI ID CHEBI:65529
Definition A quassinoid isolated from Brucea javanica and Brucea sumatrana 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 C21H26O10
Net Charge 0
Average Mass 438.42510
Monoisotopic Mass 438.15260
InChI InChI=1S/C21H26O10/c1-7-8-4-10-20-6-30-21(18(28)29-3,15(20)13(25)17(27)31-10)16(26)12(24)14(20)19(8,2)5-9(22)11(7)23/h8,10,12-16,23-26H,4-6H2,1-3H3/t8-,10+,12+,13+,14+,15+,16-,19-,20+,21-/m0/s1
InChIKey YLWQKYSDNGHLAO-PWRINDRCSA-N
SMILES COC(=O)[C@]12OC[C@@]34[C@H]1[C@@H](O)C(=O)O[C@@H]3C[C@H]1C(C)=C(O)C(=O)C[C@]1(C)[C@H]4[C@@H](O)[C@@H]2O
Metabolite of Species Details
Brucea sumatrana (IPNI:813620-1) See: DUOC HOC, 1979,4,15
Brucea javanica (NCBI:txid210348) Found in fruit (BTO:0000486). See: DOI
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.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing bruceolide (CHEBI:65529) has role antimalarial (CHEBI:38068)
bruceolide (CHEBI:65529) has role antineoplastic agent (CHEBI:35610)
bruceolide (CHEBI:65529) has role metabolite (CHEBI:25212)
bruceolide (CHEBI:65529) is a δ-lactone (CHEBI:18946)
bruceolide (CHEBI:65529) is a cyclic ether (CHEBI:37407)
bruceolide (CHEBI:65529) is a enol (CHEBI:33823)
bruceolide (CHEBI:65529) is a enone (CHEBI:51689)
bruceolide (CHEBI:65529) is a methyl ester (CHEBI:25248)
bruceolide (CHEBI:65529) is a organic heteropentacyclic compound (CHEBI:38164)
bruceolide (CHEBI:65529) is a quassinoid (CHEBI:72485)
bruceolide (CHEBI:65529) is a tetrol (CHEBI:33573)
Incoming 15-O-acetylbruceolide (CHEBI:65530) has functional parent bruceolide (CHEBI:65529)
15-O-propionylbruceolide (CHEBI:65531) has functional parent bruceolide (CHEBI:65529)
3,15-di-O-acetylbruceolide (CHEBI:65532) has functional parent bruceolide (CHEBI:65529)
3,15-di-O-propionylbruceolide (CHEBI:65533) has functional parent bruceolide (CHEBI:65529)
IUPAC Name
methyl (11β,12α,15β)-3,11,12,15-tetrahydroxy-2,16-dioxo-13,20-epoxypicras-3-en-21-oate
Synonym Source
Picras-3-en-21-oic acid, 13,20-epoxy-3,11,12,15-tetrahydroxy-2,16-dioxo-, methyl ester,(11beta,12alpha,15beta)- ChemIDplus
Registry Numbers Types Sources
25514-28-7 CAS Registry Number ChemIDplus
4601028 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11227768 PubMed citation Europe PMC
2062960 PubMed citation Europe PMC
3325613 PubMed citation Europe PMC
9313855 PubMed citation Europe PMC
9871598 PubMed citation Europe PMC
Last Modified
27 May 2015
General Comment
2012-07-27 DUOC HOC, 1979,4,15