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CHEBI:69874 - ajugatakasin B

ChEBI IDCHEBI:69874
ChEBI Nameajugatakasin B
Stars
DefinitionA diterpene lactone isolated from the whole plants of Ajuga ciliata that is ajugatakasin A in which both of the 2-methylbutenoate ester goups have been hydrogenated to the corresponding 2-methylbutanoates.
Last Modified24 August 2016
DownloadsMolfile
FormulaC34H50O11
Net Charge0
Average Mass634.763
Monoisotopic Mass634.33531
SMILES[H][C@]12[C@H](OC(=O)[C@@H](C)CC)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@@H](C)CC)C1=CC(=O)OC1
InChIInChI=1S/C34H50O11/c1-9-19(3)30(38)44-25-11-12-33(17-42-33)34(18-41-22(6)35)27(43-23(7)36)13-21(5)32(8,29(25)34)15-26(24-14-28(37)40-16-24)45-31(39)20(4)10-2/h14,19-21,25-27,29H,9-13,15-18H2,1-8H3/t19-,20-,21+,25+,26-,27-,29+,32-,33-,34+/m0/s1
InChIKeyFFIQZYRUFYKEBN-NVVYUONASA-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)
ajugatakasin B (CHEBI:69874) has role plant metabolite (CHEBI:76924)
ajugatakasin B (CHEBI:69874) is a acetate ester (CHEBI:47622)
ajugatakasin B (CHEBI:69874) is a butenolide (CHEBI:50523)
ajugatakasin B (CHEBI:69874) is a diterpene lactone (CHEBI:49193)
ajugatakasin B (CHEBI:69874) is a spiro-epoxide (CHEBI:133131)
IUPAC Name 
(1S)-2-[(1R,4R,4aR,5S,6R,8S,8aR)-8-(acetyloxy)-8a-[(acetyloxy)methyl]-5,6-dimethyl-4-{[(2S)-2-methylbutanoyl]oxy}octahydro-2H-spiro[naphthalene-1,2'-oxiran]-5-yl]-1-(5-oxo-2,5-dihydrofuran-3-yl)ethyl (2S)-2-methylbutanoate
Registry NumbersSources
Reaxys:21728546Reaxys
Citations