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CHEBI:67472 - 15-epi-lupulin B

ChEBI IDCHEBI:67472
ChEBI Name15-epi-lupulin B
Stars
ASCII Name15-epi-lupulin B
DefinitionA diterpenoid isolated from the aerial parts of Ajuga bracteosa and has been shown to exhibit antifeedant activity.
Last Modified24 August 2016
DownloadsMolfile
FormulaC30H46O11
Net Charge0
Average Mass582.687
Monoisotopic Mass582.30401
SMILES[H][C@]12C[C@@H](OC)O[C@@]1([H])O[C@]([H])([C@@]1(C)[C@H](C)C[C@H](OC(C)=O)[C@]3(COC(C)=O)[C@]1([H])C[C@@H](O)[C@H](OC(=O)C(C)CC)[C@]31CO1)C2
InChIInChI=1S/C30H46O11/c1-8-15(2)26(34)41-25-20(33)12-21-28(6,22-10-19-11-24(35-7)40-27(19)39-22)16(3)9-23(38-18(5)32)29(21,13-36-17(4)31)30(25)14-37-30/h15-16,19-25,27,33H,8-14H2,1-7H3/t15?,16-,19+,20-,21-,22+,23+,24+,25+,27-,28+,29+,30-/m1/s1
InChIKeyUEZOFWAZJUOMCN-NTWWNSDMSA-N
Species of MetaboliteComponentSourceComments
Ajuga bracteosa (IPNI:444535-1) aerial part (BTO:0001658) PubMed (21539300) Crude dichloromethane extract of dried and powdered aerial parts
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:
antifeedant  A substance that prevents pests from feeding.
ChEBI Ontology
Outgoing Relation(s)
15-epi-lupulin B (CHEBI:67472) has role antifeedant (CHEBI:22583)
15-epi-lupulin B (CHEBI:67472) has role plant metabolite (CHEBI:76924)
15-epi-lupulin B (CHEBI:67472) is a acetate ester (CHEBI:47622)
15-epi-lupulin B (CHEBI:67472) is a cyclic acetal (CHEBI:59770)
15-epi-lupulin B (CHEBI:67472) is a diterpenoid (CHEBI:23849)
15-epi-lupulin B (CHEBI:67472) is a furofuran (CHEBI:47790)
15-epi-lupulin B (CHEBI:67472) is a spiro-epoxide (CHEBI:133131)
IUPAC Name 
(1R,2S,3R,4aR,5S,6R,8S,8aR)-8-(acetyloxy)-8a-[(acetyloxy)methyl]-3-hydroxy-5-[(2S,3aS,5S,6aR)-5-methoxyhexahydrofuro[2,3-b]furan-2-yl]-5,6-dimethyloctahydro-2H-spiro[naphthalene-1,2'-oxiran]-2-yl 2-methylbutanoate
Registry NumbersSources
Reaxys:10136512Reaxys
Citations