ascr#5 (CHEBI:78829)

ChEBI > Main

Main

ChEBI Ontology

Automatic Xrefs

Reactions

Pathways

Models

ChEBI Name	ascr#5

ChEBI ID	CHEBI:78829

Definition	An 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.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

Download	Molfile XML SDF

Formula

C9H16O6

Net Charge

Average Mass

220.21970

Monoisotopic Mass

220.09469

InChI

InChI=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

InChIKey

RYYMJVGKZLQYPG-YYWONIAYSA-N

SMILES

C[C@@H]1O[C@@H](OCCC(O)=O)[C@H](O)C[C@H]1O

Metabolite of Species	Details
Caenorhabditis elegans (NCBI:txid6239)	See: PubMed

Roles Classification
Chemical Role(s):	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	pheromone A semiochemical used in olfactory communication between organisms of the same species eliciting a change in sexual or social behaviour. Caenorhabditis elegans metabolite A nematode metabolite produced by Caenorhabditis elegans. semiochemical A molecular messenger released by an organism that affects the behaviour within or between species. (via hydroxy fatty acid ascaroside )

ChEBI Ontology
Outgoing	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 ω-hydroxy fatty acid ascaroside (CHEBI:79204) ascr#5 (CHEBI:78829) is a monocarboxylic acid (CHEBI:25384) ascr#5 (CHEBI:78829) is conjugate acid of ascr#5(1-) (CHEBI:139707)

Incoming	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	Sources
(−)-3-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-propanoic acid	SMID
3-hydroxypropanoic acid 3-O-α-ascarylopyranoside	ChEBI
ascaroside C3	ChEBI

Last Modified

25 July 2014