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CHEBI:67463 - ajugapitin

ChEBI IDCHEBI:67463
ChEBI Nameajugapitin
Stars
DefinitionA diterpenoid isolated from the aerial parts of Ajuga bracteosa and has been shown to exhibit antifeedant activity against Spodoptera littoralis.
Last Modified24 August 2016
DownloadsMolfile
FormulaC29H42O10
Net Charge0
Average Mass550.645
Monoisotopic Mass550.27780
SMILES[H][C@@]12OC=C[C@]1([H])C[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)O2
InChIInChI=1S/C29H42O10/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/h8-9,15-16,19-24,26,32H,7,10-14H2,1-6H3/t15?,16-,19-,20-,21-,22+,23+,24+,26+,27+,28+,29-/m1/s1
InChIKeyLHFSTOLZQVESJD-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)
ajugapitin (CHEBI:67463) has role antifeedant (CHEBI:22583)
ajugapitin (CHEBI:67463) has role plant metabolite (CHEBI:76924)
ajugapitin (CHEBI:67463) is a acetate ester (CHEBI:47622)
ajugapitin (CHEBI:67463) is a cyclic acetal (CHEBI:59770)
ajugapitin (CHEBI:67463) is a diterpenoid (CHEBI:23849)
ajugapitin (CHEBI:67463) is a furofuran (CHEBI:47790)
ajugapitin (CHEBI:67463) is a spiro-epoxide (CHEBI:133131)
IUPAC Name 
(1R,2S,3R,4aR,5S,6R,8S,8aR)-8-(acetyloxy)-8a-[(acetyloxy)methyl]-3-hydroxy-5,6-dimethyl-5-[(2S,3aS,6aS)-2,3,3a,6a-tetrahydrofuro[2,3-b]furan-2-yl]octahydro-2H-spiro[naphthalene-1,2'-oxiran]-2-yl 2-methylbutanoate
Registry NumbersSources
Reaxys:6759959Reaxys
Citations