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CHEBI:67470 - 14-hydro-15-hydroxyajugachin A

ChEBI IDCHEBI:67470
ChEBI Name14-hydro-15-hydroxyajugachin A
Stars
DefinitionA diterpenoid isolated from Ajuga bracteosa and has been shown to exhibit antifeedant activity.
Last Modified24 August 2016
DownloadsMolfile
FormulaC28H42O10
Net Charge0
Average Mass538.634
Monoisotopic Mass538.27780
SMILES[H][C@]12CC(O)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])CC[C@H](OC(=O)C(C)C)[C@]31CO1)C2
InChIInChI=1S/C28H42O10/c1-14(2)24(32)36-20-8-7-19-26(6,21-10-18-11-23(31)38-25(18)37-21)15(3)9-22(35-17(5)30)27(19,12-33-16(4)29)28(20)13-34-28/h14-15,18-23,25,31H,7-13H2,1-6H3/t15-,18+,19-,20+,21+,22+,23?,25-,26+,27+,28-/m1/s1
InChIKeySGUPXQYJFIEPOK-ZJADYXILSA-N
Species of MetaboliteComponentSourceComments
Ajuga bracteosa (IPNI:444535-1) aerial part (BTO:0001658) PubMed (21539300) Crude dichloromethane extract of dried and powdered aerial parts, C-15 epimeric mixture
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-hydro-15-hydroxyajugachin A (CHEBI:67470) has role antifeedant (CHEBI:22583)
14-hydro-15-hydroxyajugachin A (CHEBI:67470) has role plant metabolite (CHEBI:76924)
14-hydro-15-hydroxyajugachin A (CHEBI:67470) is a acetate ester (CHEBI:47622)
14-hydro-15-hydroxyajugachin A (CHEBI:67470) is a cyclic acetal (CHEBI:59770)
14-hydro-15-hydroxyajugachin A (CHEBI:67470) is a diterpenoid (CHEBI:23849)
14-hydro-15-hydroxyajugachin A (CHEBI:67470) is a furofuran (CHEBI:47790)
14-hydro-15-hydroxyajugachin A (CHEBI:67470) is a spiro-epoxide (CHEBI:133131)
IUPAC Name 
(1R,2S,4aR,5S,6R,8S,8aR)-8-(acetyloxy)-8a-[(acetyloxy)methyl]-5-[(2S,3aS,6aR)-5-hydroxyhexahydrofuro[2,3-b]furan-2-yl]-5,6-dimethyloctahydro-2H-spiro[naphthalene-1,2'-oxiran]-2-yl 2-methylpropanoate
Citations