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CHEBI:67467 - 14,15-dihydroajugapitin

ChEBI IDCHEBI:67467
ChEBI Name14,15-dihydroajugapitin
Stars
DefinitionA diterpenoid isolated from the aerial parts of Ajuga bracteosa.
Last Modified23 August 2016
DownloadsMolfile
FormulaC29H44O10
Net Charge0
Average Mass552.661
Monoisotopic Mass552.29345
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])C[C@@H](O)[C@H](OC(=O)C(C)CC)[C@]31CO1)C2
InChIInChI=1S/C29H44O10/c1-7-15(2)25(33)39-24-20(32)12-21-27(6,22-11-19-8-9-34-26(19)38-22)16(3)10-23(37-18(5)31)28(21,13-35-17(4)30)29(24)14-36-29/h15-16,19-24,26,32H,7-14H2,1-6H3/t15?,16-,19-,20-,21-,22+,23+,24+,26+,27+,28+,29-/m1/s1
InChIKeyXMVULWKEVGKECE-DBNYLVSFSA-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)
14,15-dihydroajugapitin (CHEBI:67467) has role antifeedant (CHEBI:22583)
14,15-dihydroajugapitin (CHEBI:67467) has role plant metabolite (CHEBI:76924)
14,15-dihydroajugapitin (CHEBI:67467) is a acetate ester (CHEBI:47622)
14,15-dihydroajugapitin (CHEBI:67467) is a cyclic acetal (CHEBI:59770)
14,15-dihydroajugapitin (CHEBI:67467) is a diterpenoid (CHEBI:23849)
14,15-dihydroajugapitin (CHEBI:67467) is a furofuran (CHEBI:47790)
14,15-dihydroajugapitin (CHEBI:67467) is a spiro-epoxide (CHEBI:133131)
IUPAC Name 
(1R,2S,3R,4aR,5S,6R,8S,8aR)-8-(acetyloxy)-8a-[(acetyloxy)methyl]-5-[(2S,3aR,6aS)-hexahydrofuro[2,3-b]furan-2-yl]-3-hydroxy-5,6-dimethyloctahydro-2H-spiro[naphthalene-1,2'-oxiran]-2-yl 2-methylbutanoate
Registry NumbersSources
Reaxys:6759279Reaxys
Citations