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CHEBI:69879 - ajuganipponin A

ChEBI IDCHEBI:69879
ChEBI Nameajuganipponin A
Stars
DefinitionA diterpene lactone isolated from the whole plants of Ajuga ciliata.
Last Modified24 August 2016
DownloadsMolfile
FormulaC31H42O11
Net Charge0
Average Mass590.666
Monoisotopic Mass590.27271
SMILES[H][C@]12[C@H](OC(C)=O)CC[C@]3(CO3)[C@]1(COC(C)=O)[C@@H](OC(C)=O)C[C@@H](C)[C@]2(C)C[C@H](OC(=O)/C(C)=C/C)C1=CC(=O)OC1
InChIInChI=1S/C31H42O11/c1-8-17(2)28(36)42-24(22-12-26(35)37-14-22)13-29(7)18(3)11-25(41-21(6)34)31(16-38-19(4)32)27(29)23(40-20(5)33)9-10-30(31)15-39-30/h8,12,18,23-25,27H,9-11,13-16H2,1-7H3/b17-8+/t18-,23-,24+,25+,27-,29+,30+,31-/m1/s1
InChIKeySJNMHXILDVKBPL-BEEMTZEWSA-N
Species of MetaboliteComponentSourceComments
Ajuga ciliata (ncbitaxon:199542) whole plant (BTO:0001461) PubMed (21682262) Methanol extract of air-dried whole plant
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.
ChEBI Ontology
Outgoing Relation(s)
ajuganipponin A (CHEBI:69879) has role plant metabolite (CHEBI:76924)
ajuganipponin A (CHEBI:69879) is a acetate ester (CHEBI:47622)
ajuganipponin A (CHEBI:69879) is a butenolide (CHEBI:50523)
ajuganipponin A (CHEBI:69879) is a diterpene lactone (CHEBI:49193)
ajuganipponin A (CHEBI:69879) is a enoate ester (CHEBI:51702)
ajuganipponin A (CHEBI:69879) is a spiro-epoxide (CHEBI:133131)
IUPAC Name 
(1S)-2-{(1R,4R,4aR,5S,6R,8S,8aR)-4,8-bis(acetyloxy)-8a-[(acetyloxy)methyl]-5,6-dimethyloctahydro-2H-spiro[naphthalene-1,2'-oxiran]-5-yl}-1-(5-oxo-2,5-dihydrofuran-3-yl)ethyl (2E)-2-methylbut-2-enoate
Registry NumbersSources
Reaxys:21728543Reaxys
Citations