Molecule ID: 9548904

IUPAC Name: 4-[(2R,3S,4S,5S)-5-(3,4-dimethoxyphenyl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol

Description: The molecule is 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). It has a role as a metabolite and an EC 1.14.13.39 (nitric oxide synthase) inhibitor. It is a lignan, a member of methoxybenzenes, a member of oxolanes and a member of phenols.

SMILES: COc1cc([C@@H]2O[C@H](c3ccc(OC)c(OC)c3)[C@@H](C)[C@@H]2C)ccc1O

SELFIES: [C][O][C][=C][C][Branch2][Ring1][=C][C@@H1][O][C@H1][Branch1][P][C][=C][C][=C][Branch1][Ring1][O][C][C][Branch1][Ring1][O][C][=C][Ring1][#Branch2][C@@H1][Branch1][C][C][C@@H1][Ring1][S][C][=C][C][=C][Ring2][Ring1][#Branch1][O]

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

Molecular Properties:
- Polar Surface Area: 57.2 Ų
- LogP: 4.1