Molecule ID: 132282049

IUPAC Name: (1R,4S,6R,7R,17R)-4,7-dihydroxy-4-[(1R)-1-hydroxyethyl]-6,7-dimethyl-14-oxido-2,9-dioxa-14-azoniatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione

Description: The molecule is a pyrrolizine alkaloid that is jacoline in which the tertiary amino function has been oxidised to the corresponding N-oxide. It has a role as a Jacobaea metabolite. It is a macrocyclic lactone, an organic heterotricyclic compound, a pyrrolizine alkaloid, a triol and a tertiary amine oxide. It derives from a jacoline.

SMILES: C[C@@H]1C[C@](O)([C@@H](C)O)C(=O)O[C@@H]2CC[N+]3([O-])CC=C(COC(=O)[C@]1(C)O)[C@H]23

SELFIES: [C][C@@H1][C][C@][Branch1][C][O][Branch1][=Branch1][C@@H1][Branch1][C][C][O][C][=Branch1][C][=O][O][C@@H1][C][C][N+1][Branch1][C][O-1][C][C][=C][Branch1][#C][C][O][C][=Branch1][C][=O][C@][Ring2][Ring1][#Branch1][Branch1][C][C][O][C@H1][Ring1][S][Ring1][=N]

InChI: InChI=1S/C18H27NO8/c1-10-8-18(24,11(2)20)16(22)27-13-5-7-19(25)6-4-12(14(13)19)9-26-15(21)17(10,3)23/h4,10-11,13-14,20,23-24H,5-9H2,1-3H3/t10-,11-,13-,14-,17-,18+,19?/m1/s1

Molecular Properties:
- Polar Surface Area: 131.0 Ų
- LogP: -0.7