Molecule ID: 21581040

IUPAC Name: [(1S,2R,5S,6S,7S,9R,12R)-5-acetyloxy-12-(furan-3-carbonyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.01,6]dodecan-7-yl] furan-3-carboxylate

Description: The molecule is a dihydroagarofuran sesquiterpenoid that consists of dihydro-beta-agarofuran substituted by acetoxy group at position 1 and furoyloxy groups at positions 6 and 9 (the 1beta,6alpha,9alpha stereoisomer). Isolated from Celastrus orbiculatus, it exhibits inhibition of both NF-kappaB activation and nitric oxide production. It has a role as a metabolite and a NF-kappaB inhibitor. It is an acetate ester, a bridged compound, a cyclic ether, a dihydroagarofuran sesquiterpenoid and an organic heterotricyclic compound. It derives from a 3-furoic acid.

SMILES: CC(=O)O[C@H]1CC[C@@H](C)[C@]23OC(C)(C)[C@H](C[C@H](OC(=O)c4ccoc4)[C@]12C)[C@H]3OC(=O)c1ccoc1

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

InChI: InChI=1S/C27H32O9/c1-15-6-7-20(33-16(2)28)26(5)21(34-23(29)17-8-10-31-13-17)12-19-22(27(15,26)36-25(19,3)4)35-24(30)18-9-11-32-14-18/h8-11,13-15,19-22H,6-7,12H2,1-5H3/t15-,19-,20+,21+,22-,26+,27-/m1/s1

Molecular Properties:
- Polar Surface Area: 114.0 Ų
- LogP: 4.0