CHEBI:65526 - bruceanol D

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ChEBI Name bruceanol D
ChEBI ID CHEBI:65526
Definition A quassinoid natural product found in Brucea antidysenterica consisting of a heteropentacyclic skeleton containing a δ-lactone moiety which is substituted at the α-carbon by a (2E)-3,4-dimethylpent-2-enoyloxy group. It shows significant in vitro cytotoxicity towards several human tumour cell lines.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C28H36O11
Net Charge 0
Average Mass 548.57880
Monoisotopic Mass 548.226
InChI InChI=1S/C28H36O11/c1-11(2)12(3)8-17(30)39-19-21-27-10-37-28(21,25(35)36-6)23(33)18(31)20(27)26(5)14(9-16(27)38-24(19)34)13(4)7-15(29)22(26)32/h7-8,11,14,16,18-23,31-33H,9-10H2,1-6H3/b12-8+/t14-,16+,18+,19+,20+,21+,22+,23-,26-,27+,28-/m0/s1
InChIKey BOUBPFYATGCWDW-UENHEUQBSA-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(OC[C@@]13[C@@]4([H])[C@@H](OC(=O)\C=C(/C)C(C)C)C(=O)O2)C(=O)OC
Metabolite of Species Details
Brucea antidysenterica (NCBI:459111) Found in xylem (BTO:0001468). Previous component: ground wood; 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.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing bruceanol D (CHEBI:65526) has role antineoplastic agent (CHEBI:35610)
bruceanol D (CHEBI:65526) has role metabolite (CHEBI:25212)
bruceanol D (CHEBI:65526) is a δ-lactone (CHEBI:18946)
bruceanol D (CHEBI:65526) is a cyclic ether (CHEBI:37407)
bruceanol D (CHEBI:65526) is a enoate ester (CHEBI:51702)
bruceanol D (CHEBI:65526) is a enone (CHEBI:51689)
bruceanol D (CHEBI:65526) is a methyl ester (CHEBI:25248)
bruceanol D (CHEBI:65526) is a organic heteropentacyclic compound (CHEBI:38164)
bruceanol D (CHEBI:65526) is a pentacyclic triterpenoid (CHEBI:25872)
bruceanol D (CHEBI:65526) is a quassinoid (CHEBI:72485)
bruceanol D (CHEBI:65526) is a secondary α-hydroxy ketone (CHEBI:2468)
bruceanol D (CHEBI:65526) is a triol (CHEBI:27136)
IUPAC Name
methyl (1β,11β,12α,15β)-15-{[(2E)-3,4-dimethylpent-2-enoyl]oxy}-1,11,12-trihydroxy-2,16-dioxo-13,20-epoxypicras-3-en-21-oate
Synonym Source
Picras-3-en-21-oic acid, 15-((3,4-dimethyl-1-oxo-2-pentenyl)oxy)-13,20-epoxy-1,11,12-trihydroxy-2,16-dioxo-,methyl ester, (1beta,11beta,12alpha,15beta(E))- ChemIDplus
Registry Number Type Source
152645-84-6 CAS Registry Number ChemIDplus
Citation Waiting for Citations Type Source
8133299 PubMed citation Europe PMC
Last Modified
06 February 2018