Molecule ID: 16066476

IUPAC Name: (E,8R)-8-[(2R,3R,5R,6S)-3,5-dihydroxy-6-methyloxan-2-yl]oxynon-2-enoic acid

Description: The molecule is an (omega-1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (2E,8R)-8-hydroxynon-2-enoic acid with ascarylopyranose (the alpha anomer). It is a major component of the dauer pheromone, used by the nematode Caenorhabditis elegans as a population-density signal to promote entry into an alternate larval stage, the nonfeeding and highly persistent dauer diapause, and also synergises with ascr#2, ascr#4, and ascr#8 in male attraction. It has a role as a Caenorhabditis elegans metabolite and a pheromone. It is an alpha,beta-unsaturated monocarboxylic acid and an (omega-1)-hydroxy fatty acid ascaroside. It derives from a (2E,8R)-8-hydroxynon-2-enoic acid. It is a conjugate acid of an ascr#3(1-).

SMILES: C[C@H](CCCC/C=C/C(=O)O)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O

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

InChI: InChI=1S/C15H26O6/c1-10(7-5-3-4-6-8-14(18)19)20-15-13(17)9-12(16)11(2)21-15/h6,8,10-13,15-17H,3-5,7,9H2,1-2H3,(H,18,19)/b8-6+/t10-,11+,12-,13-,15-/m1/s1

Molecular Properties:
- Polar Surface Area: 96.2 Ų
- LogP: 1.4