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CHEBI:65527 - bruceanol E

ChEBI IDCHEBI:65527
ChEBI Namebruceanol E
Stars
DefinitionA quassinoid that is the dihydro derivative of bruceanol D. Isolated from Brucea antidysenterica, it exhibits in vitro cytotoxicity towards several human tumour cell lines.
Last Modified6 February 2018
DownloadsMolfile
FormulaC28H38O11
Net Charge0
Average Mass550.601
Monoisotopic Mass550.24141
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@H](C)CC(=O)[C@@H](O)[C@]21C
InChIInChI=1S/C28H38O11/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/h8,11,13-14,16,18-23,31-33H,7,9-10H2,1-6H3/b12-8+/t13-,14+,16-,18-,19-,20-,21-,22-,23+,26+,27-,28+/m1/s1
InChIKeySXRILXHNZYONKW-XZXXSJTKSA-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 E (CHEBI:65527) has role antineoplastic agent (CHEBI:35610)
bruceanol E (CHEBI:65527) has role metabolite (CHEBI:25212)
bruceanol E (CHEBI:65527) is a cyclic ether (CHEBI:37407)
bruceanol E (CHEBI:65527) is a enoate ester (CHEBI:51702)
bruceanol E (CHEBI:65527) is a methyl ester (CHEBI:25248)
bruceanol E (CHEBI:65527) is a organic heteropentacyclic compound (CHEBI:38164)
bruceanol E (CHEBI:65527) is a pentacyclic triterpenoid (CHEBI:25872)
bruceanol E (CHEBI:65527) is a quassinoid (CHEBI:72485)
bruceanol E (CHEBI:65527) is a secondary α-hydroxy ketone (CHEBI:2468)
bruceanol E (CHEBI:65527) is a triol (CHEBI:27136)
bruceanol E (CHEBI:65527) 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-epoxypicrasan-21-oate
Registry NumbersSources
CAS:152645-85-7ChemIDplus
Citations