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CHEBI:65529 - bruceolide

ChEBI IDCHEBI:65529
ChEBI Namebruceolide
Stars
DefinitionA quassinoid isolated from Brucea javanica and Brucea sumatrana and has been shown to exhibit antimalarial activity.
Last Modified27 May 2015
DownloadsMolfile
FormulaC21H26O10
Net Charge0
Average Mass438.429
Monoisotopic Mass438.15260
SMILES[H][C@]12[C@@H](O)[C@H](O)[C@@]3(C(=O)OC)OC[C@]14[C@@]3([H])[C@@H](O)C(=O)O[C@]4([H])C[C@@]1([H])C(C)=C(O)C(=O)C[C@]21C
InChIInChI=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
InChIKeyYLWQKYSDNGHLAO-PWRINDRCSA-N
Species of MetaboliteComponentSourceComments
Brucea javanica (ncbitaxon:210348) fruit (BTO:0000486) DOI (10.1016/S1383-5769(99)00023-9)
Brucea sumatrana (IPNI:813620-1) - Article (DUOC HOC, 1979,4,15)
Roles Classification
Biological Roles:
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.
Applications:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
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)
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 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)
bruceolide (CHEBI:65529) is a δ-lactone (CHEBI:18946)
Incoming Relation(s)
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 NumbersSources
Reaxys:4601028Reaxys
CAS:25514-28-7ChemIDplus
Citations