Molecule ID: 11471380

IUPAC Name: (6R)-6-[(2R,3R,5R,6S)-3,5-dihydroxy-6-methyloxan-2-yl]oxyheptanoic acid

Description: The molecule is an (omega-1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (6R)-6-hydroxyheptanoic 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. It has also been found in Pristionchus pacificus and the sour paste nematode Panagrellus redivivus. It has a role as a Caenorhabditis elegans metabolite and a pheromone. It is a monocarboxylic acid and an (omega-1)-hydroxy fatty acid ascaroside. It derives from a (6R)-6-hydroxyheptanoic acid. It is a conjugate acid of an ascr#1(1-).

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

SELFIES: [C][C@H1][Branch1][#Branch2][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/C13H24O6/c1-8(5-3-4-6-12(16)17)18-13-11(15)7-10(14)9(2)19-13/h8-11,13-15H,3-7H2,1-2H3,(H,16,17)/t8-,9+,10-,11-,13-/m1/s1

Molecular Properties:
- Polar Surface Area: 96.2 Ų
- LogP: 0.4