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futokadsurin A
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).


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03. Biological Effects of Specific Chemicals: biochemical uses [CHEBI:52206] > enzyme inhibitor [CHEBI:23924] > nitric oxide synthase inhibitor [CHEBI:61908] > futokadsurin A [CHEBI:65936]
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03. Biological Effects of Specific Chemicals 
03. Biological Effects of Specific Chemicals
 biochemical uses [CHEBI:52206] (3306) 
 enzyme inhibitor [CHEBI:23924] (825) 
 nitric oxide synthase inhibitor [CHEBI:61908] (36) 
 futokadsurin A [CHEBI:65936] (1)
 metabolite [CHEBI:25212] (2692) 
 secondary metabolite [CHEBI:26619] (2225) 
 futokadsurin A [CHEBI:65936] (1)
06. Name of Biological Source of Chemical 
06. Name of Biological Source of Chemical
 Plantae (1926) 
 Magnoliophyta (1872) 
 Magnoliopsida (1649) 
 Piperales (63) 
 Piperaceae (62) 
 Piper (62) 
 Piper futokadsura (3)
08. Chemical Category 
08. Chemical Category
 main group molecular entity [CHEBI:33579] (25650) 
 s-block molecular entity [CHEBI:33674] (7287) 
 hydrogen molecular entity [CHEBI:33608] (6932) 
 hydroxides [CHEBI:24651] (5641) 
 organic hydroxy compound [CHEBI:33822] (3050) 
 phenols [CHEBI:33853] (868) 
 futokadsurin A [CHEBI:65936] (1)
 p-block molecular entity [CHEBI:33675] (25343) 
 chalcogen molecular entity [CHEBI:33304] (15225) 
 oxygen molecular entity [CHEBI:25806] (14414) 
 hydroxides [CHEBI:24651] (5641) 
 organic hydroxy compound [CHEBI:33822] (3050) 
 phenols [CHEBI:33853] (868) 
 futokadsurin A [CHEBI:65936] (1)
 organooxygen compound [CHEBI:36963] (11352) 
 ether [CHEBI:25698] (876) 
 aromatic ether [CHEBI:35618] (353) 
 methoxybenzene [CHEBI:51683] (61) 
 futokadsurin A [CHEBI:65936] (1)
 oxacycle [CHEBI:38104] (2002) 
 oxolanes [CHEBI:26912] (352) 
 futokadsurin A [CHEBI:65936] (1)
 organochalcogen compound [CHEBI:36962] (11874) 
 organooxygen compound [CHEBI:36963] (11352) 
 ether [CHEBI:25698] (876) 
 aromatic ether [CHEBI:35618] (353) 
 methoxybenzene [CHEBI:51683] (61) 
 futokadsurin A [CHEBI:65936] (1)
 oxacycle [CHEBI:38104] (2002) 
 oxolanes [CHEBI:26912] (352) 
 futokadsurin A [CHEBI:65936] (1)
 carbon group molecular entity [CHEBI:33582] (23847) 
 organic molecular entity [CHEBI:50860] (23769) 
 heteroorganic entity [CHEBI:33285] (15197) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 organic heteromonocyclic compound [CHEBI:25693] (2004) 
 oxolanes [CHEBI:26912] (352) 
 futokadsurin A [CHEBI:65936] (1)
 oxacycle [CHEBI:38104] (2002) 
 oxolanes [CHEBI:26912] (352) 
 futokadsurin A [CHEBI:65936] (1)
 organochalcogen compound [CHEBI:36962] (11874) 
 organooxygen compound [CHEBI:36963] (11352) 
 ether [CHEBI:25698] (876) 
 aromatic ether [CHEBI:35618] (353) 
 methoxybenzene [CHEBI:51683] (61) 
 futokadsurin A [CHEBI:65936] (1)
 oxacycle [CHEBI:38104] (2002) 
 oxolanes [CHEBI:26912] (352) 
 futokadsurin A [CHEBI:65936] (1)
 organic hydroxy compound [CHEBI:33822] (3050) 
 phenols [CHEBI:33853] (868) 
 futokadsurin A [CHEBI:65936] (1)
 organic molecule [CHEBI:72695] (11399) 
 organic cyclic compound [CHEBI:33832] (7633) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 organic heteromonocyclic compound [CHEBI:25693] (2004) 
 oxolanes [CHEBI:26912] (352) 
 futokadsurin A [CHEBI:65936] (1)
 oxacycle [CHEBI:38104] (2002) 
 oxolanes [CHEBI:26912] (352) 
 futokadsurin A [CHEBI:65936] (1)
 organic aromatic compound [CHEBI:33659] (3593) 
 phenylpropanoid [CHEBI:26004] (374) 
 lignan [CHEBI:25036] (34) 
 futokadsurin A [CHEBI:65936] (1)
 phenols [CHEBI:33853] (868) 
 futokadsurin A [CHEBI:65936] (1)
 aromatic ether [CHEBI:35618] (353) 
 methoxybenzene [CHEBI:51683] (61) 
 futokadsurin A [CHEBI:65936] (1)
 polyatomic entity [CHEBI:36357] (18777) 
 molecule [CHEBI:25367] (11520) 
 cyclic compound [CHEBI:33595] (7817) 
 aromatic compound [CHEBI:33655] (3799) 
 organic aromatic compound [CHEBI:33659] (3593) 
 phenylpropanoid [CHEBI:26004] (374) 
 lignan [CHEBI:25036] (34) 
 futokadsurin A [CHEBI:65936] (1)
 phenols [CHEBI:33853] (868) 
 futokadsurin A [CHEBI:65936] (1)
 aromatic ether [CHEBI:35618] (353) 
 methoxybenzene [CHEBI:51683] (61) 
 futokadsurin A [CHEBI:65936] (1)
 monocyclic compound [CHEBI:33661] (2007) 
 heteromonocyclic compound [CHEBI:33670] (2004) 
 organic heteromonocyclic compound [CHEBI:25693] (2004) 
 oxolanes [CHEBI:26912] (352) 
 futokadsurin A [CHEBI:65936] (1)
 organic cyclic compound [CHEBI:33832] (7633) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 organic heteromonocyclic compound [CHEBI:25693] (2004) 
 oxolanes [CHEBI:26912] (352) 
 futokadsurin A [CHEBI:65936] (1)
 oxacycle [CHEBI:38104] (2002) 
 oxolanes [CHEBI:26912] (352) 
 futokadsurin A [CHEBI:65936] (1)
 organic aromatic compound [CHEBI:33659] (3593) 
 phenylpropanoid [CHEBI:26004] (374) 
 lignan [CHEBI:25036] (34) 
 futokadsurin A [CHEBI:65936] (1)
 phenols [CHEBI:33853] (868) 
 futokadsurin A [CHEBI:65936] (1)
 aromatic ether [CHEBI:35618] (353) 
 methoxybenzene [CHEBI:51683] (61) 
 futokadsurin A [CHEBI:65936] (1)
 heterocyclic compound [CHEBI:5686] (5275) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 organic heteromonocyclic compound [CHEBI:25693] (2004) 
 oxolanes [CHEBI:26912] (352) 
 futokadsurin A [CHEBI:65936] (1)
 oxacycle [CHEBI:38104] (2002) 
 oxolanes [CHEBI:26912] (352) 
 futokadsurin A [CHEBI:65936] (1)
 heteromonocyclic compound [CHEBI:33670] (2004) 
 organic heteromonocyclic compound [CHEBI:25693] (2004) 
 oxolanes [CHEBI:26912] (352) 
 futokadsurin A [CHEBI:65936] (1)
 organic molecule [CHEBI:72695] (11399) 
 organic cyclic compound [CHEBI:33832] (7633) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 organic heteromonocyclic compound [CHEBI:25693] (2004) 
 oxolanes [CHEBI:26912] (352) 
 futokadsurin A [CHEBI:65936] (1)
 oxacycle [CHEBI:38104] (2002) 
 oxolanes [CHEBI:26912] (352) 
 futokadsurin A [CHEBI:65936] (1)
 organic aromatic compound [CHEBI:33659] (3593) 
 phenylpropanoid [CHEBI:26004] (374) 
 lignan [CHEBI:25036] (34) 
 futokadsurin A [CHEBI:65936] (1)
 phenols [CHEBI:33853] (868) 
 futokadsurin A [CHEBI:65936] (1)
 aromatic ether [CHEBI:35618] (353) 
 methoxybenzene [CHEBI:51683] (61) 
 futokadsurin A [CHEBI:65936] (1)
 heteroatomic molecular entity [CHEBI:37577] (13672) 
 hydroxides [CHEBI:24651] (5641) 
 organic hydroxy compound [CHEBI:33822] (3050) 
 phenols [CHEBI:33853] (868) 
 futokadsurin A [CHEBI:65936] (1)
ChEBI Compound Accession Identifier  [CHEBI:65936]
ChEBI Compound Description  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).
ChEBI Compound Identification Number  65936
ChEBI InChI Value  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
ChEBI InChIKey Value  YPQNDHHCUQGPFN-IRTBSJMASA-N
ChEBI Compound Name  futokadsurin A
ChEBI SMILES Value  COc1cc(ccc1O)[C@@H]1O[C@@H]([C@@H](C)[C@@H]1C)c1ccc(OC)c(OC)c1
ChEBI Substance ID  160710243
ChEBI URL  ChEBI:65936
ChemSpider ID  NS
Ontomatica Chemical Accession Key (OnChAKey)  YPQNDHHCUQGPFN_IRTBSJMASA_N_000_000000
PubChem Compound ID  9548904