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CHEBI:65526 - bruceanol D

ChEBI IDCHEBI:65526
ChEBI Namebruceanol D
Stars
DefinitionA 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.
Last Modified6 February 2018
DownloadsMolfile
FormulaC28H36O11
Net Charge0
Average Mass548.585
Monoisotopic Mass548.22576
SMILES[H][C@]12[C@@H](O)[C@H](O)[C@@]3(C(=O)OC)OC[C@]14[C@@]3([H])[C@@H](OC(=O)/C=C(\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/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
InChIKeyBOUBPFYATGCWDW-UENHEUQBSA-N
Species of MetaboliteComponentSourceComments
Brucea antidysenterica (ncbitaxon:459111) xylem (BTO:0001468) PubMed (8133299) Previous component: ground wood;
Roles Classification
Biological Role:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
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 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)
bruceanol D (CHEBI:65526) is a δ-lactone (CHEBI:18946)
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 NumbersSources
CAS:152645-84-6ChemIDplus
Citations