Molecule ID: 56833962

IUPAC Name: (1R,2S,3S,7S,9R,12R,13S,14S,15R,16R,17S)-3,12,15,16-tetrahydroxy-14-(hydroxymethyl)-2,6,17-trimethyl-10-oxatetracyclo[7.7.1.02,7.013,17]heptadec-5-ene-4,11-dione

Description: The molecule is a quassinoid that is picras-3-ene substituted by hydroxy groups at positions 1, 11, 12, 15 and 21 and oxo groups at positions 2 and 16. Isolated from the ethanol extract of the stem of Brucea mollis, it exhibits cytotoxic activity. It has a role as a plant metabolite and an antineoplastic agent. It is a delta-lactone, an enone, a pentol, an organic heterotetracyclic compound, a quassinoid and a secondary alpha-hydroxy ketone. It derives from a hydride of a picrasane.

SMILES: CC1=CC(=O)[C@@H](O)[C@]2(C)[C@H]3[C@@H](O)[C@H](O)[C@H](CO)[C@@H]4[C@@H](O)C(=O)O[C@H](C[C@@H]12)[C@@]43C

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

InChI: InChI=1S/C20H28O8/c1-7-4-10(22)17(26)19(2)9(7)5-11-20(3)12(14(24)18(27)28-11)8(6-21)13(23)15(25)16(19)20/h4,8-9,11-17,21,23-26H,5-6H2,1-3H3/t8-,9+,11-,12-,13-,14-,15+,16-,17-,19+,20+/m1/s1

Molecular Properties:
- Polar Surface Area: 145.0 Ų
- LogP: -0.6