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CHEBI:68931 - bruceine D

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:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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)
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
C08752KEGG COMPOUND
C00003702KNApSAcK
Registry NumbersSources
Reaxys:9674394Reaxys
CAS:21499-66-1KEGG COMPOUND
CAS:21499-66-1ChemIDplus
Citations