Molecule ID: 16066475

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

Description: The molecule is a hydroxy ketone ascaroside obtained by formal condensation of the hydroxy group of (5R)-5-hydroxyhexan-2-one 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#3, ascr#4, and ascr#8 in male attraction. It has a role as a Caenorhabditis elegans metabolite and a pheromone. It is a methyl ketone and a hydroxy ketone ascaroside. It derives from a (5R)-5-hydroxyhexan-2-one.

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

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

InChI: InChI=1S/C12H22O5/c1-7(13)4-5-8(2)16-12-11(15)6-10(14)9(3)17-12/h8-12,14-15H,4-6H2,1-3H3/t8-,9+,10-,11-,12-/m1/s1

Molecular Properties:
- Polar Surface Area: 76.0 Ų
- LogP: -0.1