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CHEBI:68932 - yadanziolide B

ChEBI IDCHEBI:68932
ChEBI Nameyadanziolide B
Stars
DefinitionA quassinoid that is 13,20-epoxypicras-3-ene substituted by hydroxy groups at positions 1, 6, 11, 12, 14, 15 and 21 and oxo groups at positions 2 and 16. Isolated from the ethanol extract of the stem of Brucea mollis, it exhibits cytotoxic activity.
Last Modified6 February 2018
DownloadsMolfile
FormulaC20H26O11
Net Charge0
Average Mass442.417
Monoisotopic Mass442.14751
SMILES[H][C@]12[C@@H](O)[C@H](O)[C@@]3(CO)OC[C@]14[C@@]3(O)[C@@H](O)C(=O)O[C@]4([H])[C@H](O)[C@@]1([H])C(C)=CC(=O)[C@@H](O)[C@]21C
InChIInChI=1S/C20H26O11/c1-6-3-7(22)12(25)17(2)8(6)9(23)15-18-5-30-19(4-21,13(26)10(24)11(17)18)20(18,29)14(27)16(28)31-15/h3,8-15,21,23-27,29H,4-5H2,1-2H3/t8-,9-,10-,11-,12-,13+,14+,15-,17+,18+,19-,20+/m1/s1
InChIKeyQPBBQXZJTIVCTO-VWXLKGNHSA-N
Species of MetaboliteComponentSourceComments
Brucea mollis (ncbitaxon:43723) stem (BTO:0001300) PubMed (22070654) Ethanolic extract of air-dried and powdered stems
Roles Classification
Biological Role:
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)
yadanziolide B (CHEBI:68932) has parent hydride picrasane (CHEBI:36506)
yadanziolide B (CHEBI:68932) has role antineoplastic agent (CHEBI:35610)
yadanziolide B (CHEBI:68932) has role plant metabolite (CHEBI:76924)
yadanziolide B (CHEBI:68932) is a enone (CHEBI:51689)
yadanziolide B (CHEBI:68932) is a heptol (CHEBI:62610)
yadanziolide B (CHEBI:68932) is a organic heteropentacyclic compound (CHEBI:38164)
yadanziolide B (CHEBI:68932) is a quassinoid (CHEBI:72485)
yadanziolide B (CHEBI:68932) is a secondary α-hydroxy ketone (CHEBI:2468)
yadanziolide B (CHEBI:68932) is a δ-lactone (CHEBI:18946)
IUPAC Name 
(1β,6α,11β,12α,15β)-1,6,11,12,14,15,21-heptahydroxy-13,20-epoxypicras-3-ene-2,16-dione
Registry NumbersSources
Reaxys:5664336Reaxys
Citations