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CHEBI:69883 - ajuganipponin B

ChEBI IDCHEBI:69883
ChEBI Nameajuganipponin B
Stars
DefinitionA diterpene lactone isolated from the whole plants of Ajuga ciliata.
Last Modified24 August 2016
DownloadsMolfile
FormulaC29H40O9
Net Charge0
Average Mass532.630
Monoisotopic Mass532.26723
SMILES[H][C@]12CCC[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/C29H40O9/c1-7-17(2)26(33)38-22(21-12-25(32)34-14-21)13-27(6)18(3)11-24(37-20(5)31)29(16-35-19(4)30)23(27)9-8-10-28(29)15-36-28/h7,12,18,22-24H,8-11,13-16H2,1-6H3/b17-7+/t18-,22+,23-,24+,27+,28+,29+/m1/s1
InChIKeyCHIBTOSDROCERR-OEGSVNHNSA-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 B (CHEBI:69883) has role plant metabolite (CHEBI:76924)
ajuganipponin B (CHEBI:69883) is a acetate ester (CHEBI:47622)
ajuganipponin B (CHEBI:69883) is a butenolide (CHEBI:50523)
ajuganipponin B (CHEBI:69883) is a diterpene lactone (CHEBI:49193)
ajuganipponin B (CHEBI:69883) is a enoate ester (CHEBI:51702)
ajuganipponin B (CHEBI:69883) is a spiro-epoxide (CHEBI:133131)
IUPAC Name 
(1S)-2-{(1R,4aR,5S,6R,8S,8aR)-8-(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:21728542Reaxys
Citations