Molecule ID: 11786580

IUPAC Name: (1R,2S)-1-[(3R)-3-carboxy-3-hydroxy-3-[(3R,5R)-2-oxo-5-[(1E,5Z,8Z)-tetradeca-1,5,8-trienyl]oxolan-3-yl]propanoyl]oxypropane-1,2,3-tricarboxylic acid

Description: The molecule is a carboxylic ester obtained by the formal condensation of the 4-carboxy group of (2R)-2-hydroxy-2-{(3R,5R)-2-oxo-5-[(1E,5Z,8Z)-tetradeca-1,5,8-trien-1-yl]tetrahydrofuran-3-yl}butanedioic acid with the hydroxy group of 3-carboxy-2,3-dideoxy-L-threo-pentaric acid. It is a fungal metabolite that acts as an inhibitor of geranylgeranyltransferase type I(GGTase I) of pathogenic fungal species. It has a role as a metabolite, an antifungal agent and an EC 2.5.1.59 (protein geranylgeranyltransferase type I) inhibitor. It is a tetracarboxylic acid, a carboxylic ester and a butan-4-olide. It derives from a pentaric acid.

SMILES: CCCCC/C=C\C/C=C\CC/C=C/[C@H]1C[C@H]([C@](O)(CC(=O)O[C@@H](C(=O)O)[C@H](CC(=O)O)C(=O)O)C(=O)O)C(=O)O1

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

InChI: InChI=1S/C28H38O13/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-18-15-20(26(36)40-18)28(39,27(37)38)17-22(31)41-23(25(34)35)19(24(32)33)16-21(29)30/h6-7,9-10,13-14,18-20,23,39H,2-5,8,11-12,15-17H2,1H3,(H,29,30)(H,32,33)(H,34,35)(H,37,38)/b7-6-,10-9-,14-13+/t18-,19-,20-,23+,28+/m0/s1

Molecular Properties:
- Polar Surface Area: 222.0 Ų
- LogP: 3.2