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CHEBI:78829 - ascr#5

ChEBI IDCHEBI:78829
ChEBI Nameascr#5
Stars
DefinitionAn ω-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of 3-hydroxypropanoic acid with ascarylopyranose (the α anomer). A major component of the dauer pheromone of the nematode Caenorhabditis elegans, it synergises with ascr#2 and ascr#3 as a population-density signal to promote entry into an alternate larval stage, the nonfeeding and highly persistent dauer diapause.
Last Modified25 July 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC9H16O6
Net Charge0
Average Mass220.221
Monoisotopic Mass220.09469
SMILESC[C@@H]1O[C@@H](OCCC(=O)O)[C@H](O)C[C@H]1O
InChIInChI=1S/C9H16O6/c1-5-6(10)4-7(11)9(15-5)14-3-2-8(12)13/h5-7,9-11H,2-4H2,1H3,(H,12,13)/t5-,6+,7+,9+/m0/s1
InChIKeyRYYMJVGKZLQYPG-YYWONIAYSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (18791072)
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
Caenorhabditis elegans metabolite  A nematode metabolite produced by Caenorhabditis elegans.
pheromone  A semiochemical used in olfactory communication between organisms of the same species eliciting a change in sexual or social behaviour.
semiochemical  A molecular messenger released by an organism that affects the behaviour within or between species.
ChEBI Ontology
Outgoing Relation(s)
ascr#5 (CHEBI:78829) has functional parent 3-hydroxypropionic acid (CHEBI:33404)
ascr#5 (CHEBI:78829) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ascr#5 (CHEBI:78829) has role pheromone (CHEBI:26013)
ascr#5 (CHEBI:78829) is a monocarboxylic acid (CHEBI:25384)
ascr#5 (CHEBI:78829) is a ω-hydroxy fatty acid ascaroside (CHEBI:79204)
ascr#5 (CHEBI:78829) is conjugate acid of ascr#5(1-) (CHEBI:139707)
Incoming Relation(s)
ascr#5(1-) (CHEBI:139707) is conjugate base of ascr#5 (CHEBI:78829)
IUPAC Name 
3-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]propanoic acid
Synonyms  Source
(−)-3-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-propanoic acidSMID
3-hydroxypropanoic acid 3-O-α-ascarylopyranosideChEBI
ascaroside C3ChEBI
Manual XrefsDatabases
ascr%235%0DSMID
Registry NumbersSources
Reaxys:22233379Reaxys
CAS:1086696-26-5SMID
Citations