Molecule ID: 442266

IUPAC Name: (3aR,4S,9aS,9bR)-4-hydroxy-9-(hydroxymethyl)-6-methyl-3-methylidene-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-2,7-dione

Description: The molecule is an azulenofuran that is 3-methylidene-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2,7-dione carrying additional hydroxy, methyl and hydroxymethyl substituents at positions 4, 6 and 9 respectively (the 3aR,4S,9aS,9bR-diastereomer). Found in chicory. It has a role as an antimalarial, a sedative and a plant metabolite. It is a sesquiterpene lactone, an azulenofuran, a cyclic terpene ketone, an enone, a primary alcohol and a secondary alcohol.

SMILES: C=C1C(=O)O[C@@H]2[C@H]3C(CO)=CC(=O)C3=C(C)C[C@H](O)[C@@H]12

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

InChI: InChI=1S/C15H16O5/c1-6-3-9(17)12-7(2)15(19)20-14(12)13-8(5-16)4-10(18)11(6)13/h4,9,12-14,16-17H,2-3,5H2,1H3/t9-,12+,13-,14-/m0/s1

Molecular Properties:
- Polar Surface Area: 83.8 Ų
- LogP: -0.7