Molecule ID: 70697724

IUPAC Name: methyl (1R,2S,3R,6R,8S,12S,13S,14R,15R,16S,17S)-3-[(E)-3,4-dimethylpent-2-enoyl]oxy-12,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylate

Description: The molecule is a quassinoid natural product found in Brucea antidysenterica consisting of a heteropentacyclic skeleton containing a delta-lactone moiety which is substituted at the alpha-carbon by a (2E)-3,4-dimethylpent-2-enoyloxy group. It shows significant in vitro cytotoxicity towards several human tumour cell lines. It has a role as a metabolite and an antineoplastic agent. It is a pentacyclic triterpenoid, an organic heteropentacyclic compound, an enone, an enoate ester, a delta-lactone, a triol, a cyclic ether, a quassinoid, a methyl ester and a secondary alpha-hydroxy ketone.

SMILES: COC(=O)[C@@]12OC[C@]34[C@H]([C@@H](O)[C@@H]1O)[C@@]1(C)[C@H](O)C(=O)C=C(C)[C@@H]1C[C@H]3OC(=O)[C@H](OC(=O)/C=C(\C)C(C)C)[C@@H]24

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

InChI: InChI=1S/C28H36O11/c1-11(2)12(3)8-17(30)39-19-21-27-10-37-28(21,25(35)36-6)23(33)18(31)20(27)26(5)14(9-16(27)38-24(19)34)13(4)7-15(29)22(26)32/h7-8,11,14,16,18-23,31-33H,9-10H2,1-6H3/b12-8+/t14-,16+,18+,19+,20+,21+,22+,23-,26-,27+,28-/m0/s1

Molecular Properties:
- Polar Surface Area: 166.0 Ų
- LogP: 1.3