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CHEBI:68931 - bruceine D

Default Structure
ChEBI IDCHEBI:68931
ChEBI Namebruceine D
Stars
DefinitionA quassinoid that is 13,20-epoxypicras-3-ene substituted by hydroxy groups at positions 1, 11, 12, 14 and 15 and oxo groups at positions 2 and 16. Isolated from the ethanol extract of the stem of Brucea mollis, it exhibits cytotoxic activity.
Secondary ChEBI IDCHEBI:3191
Last Modified6 February 2018
DownloadsMolfile
FormulaC20H26O9
Net Charge0
Average Mass410.419
Monoisotopic Mass410.15768
SMILES[H][C@]12[C@@H](O)[C@H](O)[C@@]3(C)OC[C@]14[C@@]3(O)[C@@H](O)C(=O)O[C@]4([H])C[C@@]1([H])C(C)=CC(=O)[C@@H](O)[C@]21C
InChIInChI=1S/C20H26O9/c1-7-4-9(21)13(23)17(2)8(7)5-10-19-6-28-18(3,14(24)11(22)12(17)19)20(19,27)15(25)16(26)29-10/h4,8,10-15,22-25,27H,5-6H2,1-3H3/t8-,10+,11+,12+,13+,14-,15-,17-,18+,19+,20+/m0/s1
InChIKeyJBDMZGKDLMGOFR-KQSRGDCESA-N
Species of MetaboliteComponentSourceComments
Brucea mollis (ncbitaxon:43723) stem (BTO:0001300) PubMed (22070654) Ethanolic extract of air-dried and powdered stems
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.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
bruceine D (CHEBI:68931) has parent hydride picrasane (CHEBI:36506)
bruceine D (CHEBI:68931) has role antineoplastic agent (CHEBI:35610)
bruceine D (CHEBI:68931) has role metabolite (CHEBI:25212)
bruceine D (CHEBI:68931) has role plant metabolite (CHEBI:76924)
bruceine D (CHEBI:68931) is a organic heteropentacyclic compound (CHEBI:38164)
bruceine D (CHEBI:68931) is a pentol (CHEBI:37205)
bruceine D (CHEBI:68931) is a quassinoid (CHEBI:72485)
bruceine D (CHEBI:68931) is a secondary α-hydroxy ketone (CHEBI:2468)
bruceine D (CHEBI:68931) is a δ-lactone (CHEBI:18946)
IUPAC Name 
(1β,11β,12α,15β)-1,11,12,14,15-pentahydroxy-13,20-epoxypicras-3-ene-2,16-dione
Manual XrefsDatabases
C00003702KNApSAcK
C08752KEGG COMPOUND
Registry NumbersSources
Reaxys:9674394Reaxys
CAS:21499-66-1KEGG COMPOUND
CAS:21499-66-1ChemIDplus
Citations