CHEBI:142257 - dihydrofukinolide

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ChEBI Name dihydrofukinolide
ChEBI ID CHEBI:142257
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Mark Williams
Supplier Information
Download Molfile XML SDF
Formula C22H32O6
Net Charge 0
Average Mass 392.487
Monoisotopic Mass 392.21989
InChI InChI=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
InChIKey RLFYIIYBXGSPOM-OATMBDEBSA-N
SMILES C[C@H]1CC[C@@H]([C@@]2([C@H]([C@]3(C[C@]12C)C(=O)OCC3=C)OC(C)=O)[H])OC(=O)[C@@H](C)CC
Metabolite of Species Details
Petasites japonicus (NCBI:txid186965) Found in flower stalk (BTO:0002244). See: 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(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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ChEBI Ontology
Outgoing dihydrofukinolide (CHEBI:142257) has role plant metabolite (CHEBI:76924)
dihydrofukinolide (CHEBI:142257) is a γ-lactone (CHEBI:37581)
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)
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 Xrefs Databases
C00021356 KNApSAcK
FDB013186 FooDB
HMDB0034662 HMDB
View more database links
Registry Numbers Types Sources
1271946 Reaxys Registry Number Reaxys
41059-95-4 CAS Registry Number KNApSAcK
41059-95-4 CAS Registry Number FooDB
Last Modified
27 September 2018