Molecule ID: 441788

IUPAC Name: (1R,2R,3R,6R,8S,12S,13S,14R,15R,16S,17R)-2,3,12,15,16-pentahydroxy-9,13,17-trimethyl-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-4,11-dione

Description: The molecule is a quassinoid that is 13,20-epoxypicras-3-ene substituted by hydroxy groups at positions 1, 11, 12, 14 and 15 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 metabolite, an antineoplastic agent and a plant metabolite. It is a delta-lactone, a pentol, a quassinoid, an organic heteropentacyclic compound 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@@]4(C)OC[C@@]35[C@@H](C[C@@H]12)OC(=O)[C@H](O)[C@]54O

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

InChI: InChI=1S/C20H26O9/c1-7-4-9(21)13(23)17(2)8(7)5-10-19-6-28-18(3,14(24)11(22)12(17)19)20(19,27)15(25)16(26)29-10/h4,8,10-15,22-25,27H,5-6H2,1-3H3/t8-,10+,11+,12+,13+,14-,15-,17-,18+,19+,20+/m0/s1

Molecular Properties:
- Polar Surface Area: 154.0 Ų
- LogP: -2.4