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CHEBI:142257 - dihydrofukinolide

ChEBI IDCHEBI:142257
ChEBI Namedihydrofukinolide
Stars
DefinitionA sesquiterpene lactone that is (3R,3a'R)-decahydrospiro[furan-3,2'-indene] carrying an oxo, methylene, acetoxy, [(2S)-2-methylbutanoyl]oxy, methyl and methyl groups at positions 2, 4, 3', 4', 7' and 7a', respectively.
Last Modified27 September 2018
Submittermwilliams
DownloadsMolfile
FormulaC22H32O6
Net Charge0
Average Mass392.492
Monoisotopic Mass392.21989
SMILES[H][C@]12[C@@H](OC(=O)[C@@H](C)CC)CC[C@H](C)[C@@]1(C)C[C@@]1(C(=C)COC1=O)[C@@H]2OC(C)=O
InChIInChI=1S/C22H32O6/c1-7-12(2)19(24)28-16-9-8-13(3)21(6)11-22(14(4)10-26-20(22)25)18(17(16)21)27-15(5)23/h12-13,16-18H,4,7-11H2,1-3,5-6H3/t12-,13-,16-,17+,18+,21+,22+/m0/s1
InChIKeyRLFYIIYBXGSPOM-OATMBDEBSA-N
Species of MetaboliteComponentSourceComments
Petasites japonicus (ncbitaxon:186965) flower stalk (BTO:0002244) Article (Naya, K., Hayashi, M., Takagi, I., Nakamura, S. and Kobayashi, M. (1972) The structural elucidation of sesquiterpene lactones from Petasites japonicus Maxim. Bull. Chem. Soc. Jpn., 45(12), 3673-3685.)
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)
dihydrofukinolide (CHEBI:142257) has role plant metabolite (CHEBI:76924)
dihydrofukinolide (CHEBI:142257) is a acetate ester (CHEBI:47622)
dihydrofukinolide (CHEBI:142257) is a oxaspiro compound (CHEBI:37948)
dihydrofukinolide (CHEBI:142257) is a sesquiterpene lactone (CHEBI:37667)
dihydrofukinolide (CHEBI:142257) is a γ-lactone (CHEBI:37581)
IUPAC Name 
(3R,3'R,3a'R,4'S,7'S,7a'R)-3'-acetoxy-7',7a'-dimethyl-4-methylene-2-oxodecahydrospiro[furan-3,2'-inden]-4'-yl (2S)-2-methylbutanoate
Manual XrefsDatabases
HMDB0034662HMDB
FDB013186FooDB
C00021356KNApSAcK
Registry NumbersSources
Reaxys:1271946Reaxys
CAS:41059-95-4FooDB
CAS:41059-95-4KNApSAcK