CHEBI:65936 - futokadsurin A

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ChEBI Name futokadsurin A
Definition A 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).
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C21H26O5
Net Charge 0
Average Mass 358.42810
Monoisotopic Mass 358.17802
InChI InChI=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
SMILES COc1cc(ccc1O)[C@@H]1O[C@@H]([C@@H](C)[C@@H]1C)c1ccc(OC)c(OC)c1
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 A (CHEBI:65936) has role EC (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)
Synonym Source
rel-(7S,8S,7'R,8'S)-3,4,3'-trimethoxy-4'-hydroxy-7,7'-epoxylignan ChEBI
Registry Number Type Source
10123916 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
15635246 PubMed citation Europe PMC
17764190 PubMed citation Europe PMC
Last Modified
29 January 2013