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CHEBI:67471 - 14-hydro-15-hydroxyajugapitin

ChEBI IDCHEBI:67471
ChEBI Name14-hydro-15-hydroxyajugapitin
Stars
DefinitionA diterpenoid isolated from the aerial parts of Ajuga bracteosa and has been shown to exhibit antifeedant activity.
Last Modified24 August 2016
DownloadsMolfile
FormulaC29H44O11
Net Charge0
Average Mass568.660
Monoisotopic Mass568.28836
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])C[C@@H](O)[C@H](OC(=O)C(C)CC)[C@]31CO1)C2
InChIInChI=1S/C29H44O11/c1-7-14(2)25(34)40-24-19(32)11-20-27(6,21-9-18-10-23(33)39-26(18)38-21)15(3)8-22(37-17(5)31)28(20,12-35-16(4)30)29(24)13-36-29/h14-15,18-24,26,32-33H,7-13H2,1-6H3/t14?,15-,18+,19-,20-,21+,22+,23?,24+,26-,27+,28+,29-/m1/s1
InChIKeySAENNVULKVVZSO-ZDEAQARGSA-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-hydroxyajugapitin (CHEBI:67471) has role antifeedant (CHEBI:22583)
14-hydro-15-hydroxyajugapitin (CHEBI:67471) has role plant metabolite (CHEBI:76924)
14-hydro-15-hydroxyajugapitin (CHEBI:67471) is a acetate ester (CHEBI:47622)
14-hydro-15-hydroxyajugapitin (CHEBI:67471) is a cyclic acetal (CHEBI:59770)
14-hydro-15-hydroxyajugapitin (CHEBI:67471) is a diterpenoid (CHEBI:23849)
14-hydro-15-hydroxyajugapitin (CHEBI:67471) is a furofuran (CHEBI:47790)
14-hydro-15-hydroxyajugapitin (CHEBI:67471) 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,6aR)-5-hydroxyhexahydrofuro[2,3-b]furan-2-yl]-5,6-dimethyloctahydro-2H-spiro[naphthalene-1,2'-oxiran]-2-yl 2-methylbutanoate
Synonym  Source
14-hydro-2,15-dihydroxy-3β-isobutyryloxyclerodinChEBI
Registry NumbersSources
Reaxys:6552581Reaxys
Citations