Molecule ID: 86289890

IUPAC Name: (3R,11R)-3-hydroxy-11-[(2R,3R,5R,6S)-3-hydroxy-5-(1H-indole-3-carbonyloxy)-6-methyloxan-2-yl]oxydodecanoic acid

Description: The molecule is a 4-O-(1H-indol-3-ylcarbonyl)ascaroside that is icas#20 in which the pro-R hydrogen beta to the carboxy group is replaced by a hydroxy group. It is a metabolite of the nematode Caenorhabditis elegans. It has a role as a Caenorhabditis elegans metabolite. It is an (omega-1)-hydroxy fatty acid ascaroside, a 3-hydroxy carboxylic acid, a 4-O-(1H-indol-3-ylcarbonyl)ascaroside and a monocarboxylic acid. It derives from a bhas#20, an icas#20 and a (3R,11R)-3,11-dihydroxylauric acid.

SMILES: C[C@H](CCCCCCC[C@@H](O)CC(=O)O)O[C@@H]1O[C@@H](C)[C@H](OC(=O)c2c[nH]c3ccccc23)C[C@H]1O

SELFIES: [C][C@H1][Branch2][Ring1][C][C][C][C][C][C][C][C][C@@H1][Branch1][C][O][C][C][=Branch1][C][=O][O][O][C@@H1][O][C@@H1][Branch1][C][C][C@H1][Branch2][Ring1][Ring1][O][C][=Branch1][C][=O][C][=C][NH1][C][=C][C][=C][C][=C][Ring1][=Branch2][Ring1][=Branch1][C][C@H1][Ring2][Ring1][Ring1][O]

InChI: InChI=1S/C27H39NO8/c1-17(10-6-4-3-5-7-11-19(29)14-25(31)32)34-27-23(30)15-24(18(2)35-27)36-26(33)21-16-28-22-13-9-8-12-20(21)22/h8-9,12-13,16-19,23-24,27-30H,3-7,10-11,14-15H2,1-2H3,(H,31,32)/t17-,18+,19-,23-,24-,27-/m1/s1

Molecular Properties:
- Polar Surface Area: 138.0 Ų
- LogP: 4.1