CHEBI:65937 - futokadsurin B

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ChEBI Name futokadsurin B
Definition A 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 2S,3R,4R,5R stereoisomer). Isolated from the aerial parts of Piper futokadsura, it exhibits inhibitory activity against production of nitric oxide (NO).
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C21H24O5
Net Charge 0
Average Mass 356.41230
Monoisotopic Mass 356.16237
InChI InChI=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+/m1/s1
SMILES COc1ccc(cc1OC)[C@@H]1O[C@@H]([C@H](C)[C@H]1C)c1ccc2OCOc2c1
Metabolite of Species Details
Piper futokadsura (IPNI:681476-1) Found in aerial part (BTO:0001658). See: PubMed
Roles Classification
Biological Role(s): EC (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
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing futokadsurin B (CHEBI:65937) has role EC (nitric oxide synthase) inhibitor (CHEBI:61908)
futokadsurin B (CHEBI:65937) has role metabolite (CHEBI:25212)
futokadsurin B (CHEBI:65937) is a benzodioxoles (CHEBI:38298)
futokadsurin B (CHEBI:65937) is a dimethoxybenzene (CHEBI:51681)
futokadsurin B (CHEBI:65937) is a lignan (CHEBI:25036)
futokadsurin B (CHEBI:65937) is a oxolanes (CHEBI:26912)
Synonym Source
(7R,8R,7'S,8'R)-3',4'-methylenedioxy-3,4-dimethoxy-7,7'-epoxylignan ChEBI
Registry Number Type Source
10102561 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
15635246 PubMed citation Europe PMC
Last Modified
29 January 2013