Molecule ID: 102144112

IUPAC Name: [(1R,4Z,7R,17R)-4-ethylidene-7-methyl-6-methylidene-14-oxido-3,8-dioxo-2,9-dioxa-14-azoniatricyclo[9.5.1.014,17]heptadec-11-en-7-yl] acetate

Description: The molecule is a pyrrolizine alkaloid that is seneciphylline in which the hydroxy hydrogen has been replaced by an acetyl group and the tertiary amino function has been oxidised to the corresponding N-oxide. It has a role as a Jacobaea metabolite. It is an acetate ester, a macrocyclic lactone, an olefinic compound, an organic heterotricyclic compound, a pyrrolizine alkaloid and a tertiary amine oxide. It derives from a seneciphylline.

SMILES: C=C1C/C(=C/C)C(=O)O[C@@H]2CC[N+]3([O-])CC=C(COC(=O)[C@]1(C)OC(C)=O)[C@H]23

SELFIES: [C][=C][C][/C][=Branch1][Ring1][=C][/C][C][=Branch1][C][=O][O][C@@H1][C][C][N+1][Branch1][C][O-1][C][C][=C][Branch2][Ring1][Ring2][C][O][C][=Branch1][C][=O][C@][Ring2][Ring1][Branch1][Branch1][C][C][O][C][Branch1][C][C][=O][C@H1][Ring2][Ring1][Ring1][Ring1][S]

InChI: InChI=1S/C20H25NO7/c1-5-14-10-12(2)20(4,28-13(3)22)19(24)26-11-15-6-8-21(25)9-7-16(17(15)21)27-18(14)23/h5-6,16-17H,2,7-11H2,1,3-4H3/b14-5-/t16-,17-,20-,21?/m1/s1

Molecular Properties:
- Polar Surface Area: 97.0 Ų
- LogP: 0.7