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CHEBI:65936 - futokadsurin A

ChEBI IDCHEBI:65936
ChEBI Namefutokadsurin A
Stars
DefinitionA lignan that is tetrahydrofuran substituted by methyl groups at positions 3 and 4 (relatively trans configuration), a 3,4-dimethoxyphenyl moiety at position 5 (relatively trans to the methyl group at position 4) and a 4-hydroxy-3-methoxyphenyl group at position 2 (relatively cis to the methyl group at position 3). Isolated from the aerial parts of Piper futokadsura, it exhibits inhibitory activity against production of nitric oxide (NO).
Last Modified29 January 2013
DownloadsMolfile
FormulaC21H26O5
Net Charge0
Average Mass358.434
Monoisotopic Mass358.17802
SMILESCOc1cc([C@@H]2O[C@H](c3ccc(OC)c(OC)c3)[C@@H](C)[C@@H]2C)ccc1O
InChIInChI=1S/C21H26O5/c1-12-13(2)21(15-7-9-17(23-3)19(11-15)25-5)26-20(12)14-6-8-16(22)18(10-14)24-4/h6-13,20-22H,1-5H3/t12-,13-,20+,21-/m0/s1
InChIKeyYPQNDHHCUQGPFN-IRTBSJMASA-N
Species of MetaboliteComponentSourceComments
Piper futokadsura (IPNI:681476-1) aerial part (BTO:0001658) PubMed (15635246)
Roles Classification
Biological Roles:
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).
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
futokadsurin A (CHEBI:65936) has role EC 1.14.13.39 (nitric oxide synthase) inhibitor (CHEBI:61908)
futokadsurin A (CHEBI:65936) has role metabolite (CHEBI:25212)
futokadsurin A (CHEBI:65936) is a lignan (CHEBI:25036)
futokadsurin A (CHEBI:65936) is a methoxybenzenes (CHEBI:51683)
futokadsurin A (CHEBI:65936) is a oxolanes (CHEBI:26912)
futokadsurin A (CHEBI:65936) is a phenols (CHEBI:33853)
IUPAC Name 
4-[rel-(2R,3S,4S,5S)-5-(3,4-dimethoxyphenyl)-3,4-dimethyltetrahydrofuran-2-yl]-2-methoxyphenol
Synonym  Source
rel-(7S,8S,7'R,8'S)-3,4,3'-trimethoxy-4'-hydroxy-7,7'-epoxylignanChEBI
Registry NumbersSources
Reaxys:10123916Reaxys
Citations