Molecule ID: 10366595

IUPAC Name: 5-[(E)-2-[(2R,3R)-3-(4-hydroxy-3,5-dimethoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]ethenyl]benzene-1,3-diol

Description: The molecule is a lignan that is (2R)-2,3-dihydro-1,4-benzodioxin-2-ylmethanol which is substituted by a 2-(3,5-dihydroxyphenyl)ethenyl group at position 6 and a 4-hydroxy-3,5-dimethoxyphenyl group at position 3. It is a stilbenolignan isolated from the seeds of Aiphanes aculeata and exhibits potent inhibitory efficacy against cyclooxygenase-1 and -2 (COX-1 and COX-2). It has a role as an EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor. It is a stilbenoid, a lignan, an aromatic ether and a benzodioxine.

SMILES: COc1cc([C@H]2Oc3cc(/C=C/c4cc(O)cc(O)c4)ccc3O[C@@H]2CO)cc(OC)c1O

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

InChI: InChI=1S/C25H24O8/c1-30-21-10-16(11-22(31-2)24(21)29)25-23(13-26)32-19-6-5-14(9-20(19)33-25)3-4-15-7-17(27)12-18(28)8-15/h3-12,23,25-29H,13H2,1-2H3/b4-3+/t23-,25-/m1/s1

Molecular Properties:
- Polar Surface Area: 118.0 Ų
- LogP: 3.7