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CHEBI:65938 - futokadsurin C

ChEBI IDCHEBI:65938
ChEBI Namefutokadsurin C
Stars
DefinitionA lignan that is tetrahydrofuran substituted by methyl groups at positions 3 and 4, a 3,4-dimethoxyphenyl group at position 5 and a 1,3-benzodioxol-5-yl moiety at position 2 (the 2R,3R,4S,5S stereoisomer). Isolated from the aerial parts of Piper futokadsura, it exhibits inhibitory activity against production of nitric oxide (NO).
Last Modified29 January 2013
DownloadsMolfile
FormulaC21H24O5
Net Charge0
Average Mass356.418
Monoisotopic Mass356.16237
SMILESCOc1ccc([C@H]2O[C@@H](c3ccc4c(c3)OCO4)[C@H](C)[C@@H]2C)cc1OC
InChIInChI=1S/C21H24O5/c1-12-13(2)21(15-6-8-17-19(10-15)25-11-24-17)26-20(12)14-5-7-16(22-3)18(9-14)23-4/h5-10,12-13,20-21H,11H2,1-4H3/t12-,13+,20-,21+/m0/s1
InChIKeyHSMDOSKNXLVXIP-WVGOSAFVSA-N
Species of MetaboliteComponentSourceComments
Piper futokadsura (IPNI:681476-1) aerial part (BTO:0001658) PubMed (15635246)
Roles Classification
Biological Roles:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
EC 1.14.13.39 (nitric oxide synthase) inhibitor  An EC 1.14.13.* (oxidoreductase acting on paired donors, incorporating 1 atom of oxygen, with NADH or NADPH as one donor) inhibitor that interferes with the action of nitric oxide synthase (EC 1.14.13.39).
ChEBI Ontology
Outgoing Relation(s)
futokadsurin C (CHEBI:65938) has role EC 1.14.13.39 (nitric oxide synthase) inhibitor (CHEBI:61908)
futokadsurin C (CHEBI:65938) has role metabolite (CHEBI:25212)
futokadsurin C (CHEBI:65938) is a benzodioxoles (CHEBI:38298)
futokadsurin C (CHEBI:65938) is a dimethoxybenzene (CHEBI:51681)
futokadsurin C (CHEBI:65938) is a lignan (CHEBI:25036)
futokadsurin C (CHEBI:65938) is a oxolanes (CHEBI:26912)
IUPAC Name 
5-[(2R,3R,4S,5S)-5-(3,4-dimethoxyphenyl)-3,4-dimethyltetrahydrofuran-2-yl]-1,3-benzodioxole
Synonym  Source
(7R,8R,7'S,8'S)-3',4'-dimethoxy-3,4-methylenedioxy-7,7'-epoxylignanChEBI
Registry NumbersSources
Reaxys:10102564Reaxys
Citations