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CHEBI:67465 - 3-epi-14,15-dihydrocaryoptin

ChEBI IDCHEBI:67465
ChEBI Name3-epi-14,15-dihydrocaryoptin
Stars
ASCII Name3-epi-14,15-dihydrocaryoptin
DefinitionA diterpenoid isolated from the aerial parts of Ajuga bracteosa and has been shown to exhibit antifeedant activity.
Last Modified24 August 2016
DownloadsMolfile
FormulaC26H38O9
Net Charge0
Average Mass494.581
Monoisotopic Mass494.25158
SMILES[H][C@]12CCO[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])CC[C@H](OC(C)=O)[C@]31CO1)C2
InChIInChI=1S/C26H38O9/c1-14-10-22(34-17(4)29)25(12-31-15(2)27)19(6-7-20(33-16(3)28)26(25)13-32-26)24(14,5)21-11-18-8-9-30-23(18)35-21/h14,18-23H,6-13H2,1-5H3/t14-,18-,19-,20+,21+,22+,23+,24+,25+,26-/m1/s1
InChIKeyBUBXHOXEGBNWPX-WBTQUOTHSA-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)
3-epi-14,15-dihydrocaryoptin (CHEBI:67465) has role antifeedant (CHEBI:22583)
3-epi-14,15-dihydrocaryoptin (CHEBI:67465) has role plant metabolite (CHEBI:76924)
3-epi-14,15-dihydrocaryoptin (CHEBI:67465) is a acetate ester (CHEBI:47622)
3-epi-14,15-dihydrocaryoptin (CHEBI:67465) is a cyclic acetal (CHEBI:59770)
3-epi-14,15-dihydrocaryoptin (CHEBI:67465) is a diterpenoid (CHEBI:23849)
3-epi-14,15-dihydrocaryoptin (CHEBI:67465) is a furofuran (CHEBI:47790)
3-epi-14,15-dihydrocaryoptin (CHEBI:67465) is a spiro-epoxide (CHEBI:133131)
IUPAC Name 
(1R,2S,4aR,5S,6R,8S,8aR)-8a-[(acetyloxy)methyl]-5-[(2S,3aR,6aS)-hexahydrofuro[2,3-b]furan-2-yl]-5,6-dimethyloctahydro-2H-spiro[naphthalene-1,2'-oxirane]-2,8-diyl diacetate
Registry NumbersSources
Reaxys:4728548Reaxys
Citations