CHEBI:67463 - ajugapitin

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ChEBI Name ajugapitin
ChEBI ID CHEBI:67463
Definition A diterpenoid isolated from the aerial parts of Ajuga bracteosa and has been shown to exhibit antifeedant activity against Spodoptera littoralis.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C29H42O10
Net Charge 0
Average Mass 550.63780
Monoisotopic Mass 550.27780
InChI InChI=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
InChIKey LHFSTOLZQVESJD-DBNYLVSFSA-N
SMILES CCC(C)C(=O)O[C@H]1[C@H](O)C[C@@H]2[C@@](C)([C@@H]3C[C@H]4C=CO[C@H]4O3)[C@H](C)C[C@H](OC(C)=O)[C@@]2(COC(C)=O)[C@@]11CO1
Metabolite of Species Details
Ajuga bracteosa (IPNI:444535-1) Found in aerial part (BTO:0001658). Crude dichloromethane extract of dried and powdered aerial parts See: PubMed
Roles Classification
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application(s): antifeedant
A substance that prevents pests from feeding.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Number Type Source
6759959 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
21539300 PubMed citation Europe PMC
Last Modified
24 August 2016