Molecule ID: 9548907

IUPAC Name: [(3S,3aS,4S,6S,6aS)-3,6a-dihydroxy-4-(3-oxoprop-1-en-2-yl)-1,3,3a,4,5,6-hexahydrocyclopenta[c]furan-6-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate

Description: The molecule is an iridoid monoterpenoid that is hexahydro-1H-cyclopenta[c]furan substituted by hydroxy groups at positions 1 and 3a, a 3-oxopropen-2yl group at position 6 and a trans-4-coumaroyloxy moiety at position 4 (the 1S,3aS,4S,6S,6aS stereoisomer). Isolated from the leaves of Viburnum luzonicum, it exhibits antineoplastic activity. It has a role as a metabolite and an antineoplastic agent. It is a cinnamate ester, an aldehyde, a cyclic ether, a secondary alcohol, a member of phenols, an iridoid monoterpenoid, a tertiary alcohol and an organic heterobicyclic compound. It derives from a trans-4-coumaric acid.

SMILES: C=C(C=O)[C@H]1C[C@H](OC(=O)/C=C/c2ccc(O)cc2)[C@@]2(O)CO[C@H](O)[C@@H]12

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

InChI: InChI=1S/C19H20O7/c1-11(9-20)14-8-15(19(24)10-25-18(23)17(14)19)26-16(22)7-4-12-2-5-13(21)6-3-12/h2-7,9,14-15,17-18,21,23-24H,1,8,10H2/b7-4+/t14-,15+,17-,18+,19+/m1/s1

Molecular Properties:
- Polar Surface Area: 113.0 Ų
- LogP: 0.8