CHEBI:67471 - 14-hydro-15-hydroxyajugapitin

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ChEBI Name 14-hydro-15-hydroxyajugapitin
ChEBI ID CHEBI:67471
Definition A diterpenoid isolated from the aerial parts of Ajuga bracteosa and has been shown to exhibit antifeedant activity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C29H44O11
Net Charge 0
Average Mass 568.65310
Monoisotopic Mass 568.28836
InChI InChI=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
InChIKey SAENNVULKVVZSO-ZDEAQARGSA-N
SMILES CCC(C)C(=O)O[C@H]1[C@H](O)C[C@@H]2[C@@](C)([C@@H]3C[C@H]4CC(O)O[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, C-15 epimeric mixture 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 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-isobutyryloxyclerodin ChEBI
Registry Number Type Source
6552581 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
21539300 PubMed citation Europe PMC
Last Modified
24 August 2016