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CHEBI:69885 - ajugapantin A

ChEBI IDCHEBI:69885
ChEBI Nameajugapantin A
Stars
DefinitionA diterpene lactone isolated from the whole plants of Ajuga ciliata.
Last Modified24 August 2016
DownloadsMolfile
FormulaC28H38O11
Net Charge0
Average Mass550.601
Monoisotopic Mass550.24141
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(C)=O)C1=CC(=O)OC1
InChIInChI=1S/C28H38O11/c1-15-9-23(39-19(5)32)28(14-35-16(2)29)25(21(37-17(3)30)7-8-27(28)13-36-27)26(15,6)11-22(38-18(4)31)20-10-24(33)34-12-20/h10,15,21-23,25H,7-9,11-14H2,1-6H3/t15-,21-,22+,23+,25-,26+,27+,28-/m1/s1
InChIKeyKBIJVGBQDPMKKO-BAOLRMIKSA-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)
ajugapantin A (CHEBI:69885) has role plant metabolite (CHEBI:76924)
ajugapantin A (CHEBI:69885) is a acetate ester (CHEBI:47622)
ajugapantin A (CHEBI:69885) is a butenolide (CHEBI:50523)
ajugapantin A (CHEBI:69885) is a diterpene lactone (CHEBI:49193)
ajugapantin A (CHEBI:69885) is a spiro-epoxide (CHEBI:133131)
IUPAC Name 
(1R,4R,4aR,5S,6R,8S,8aR)-8a-[(acetyloxy)methyl]-5-[(2S)-2-(acetyloxy)-2-(5-oxo-2,5-dihydrofuran-3-yl)ethyl]-5,6-dimethyloctahydro-2H-spiro[naphthalene-1,2'-oxirane]-4,8-diyl diacetate
Registry NumbersSources
Reaxys:5686507Reaxys
Citations