ascr#1 (CHEBI:78786)

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ChEBI Name	ascr#1

ChEBI ID	CHEBI:78786

Definition	An (ω−1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (6R)-6-hydroxyheptanoic acid with ascarylopyranose (the α 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.

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

Supplier Information

Download	Molfile XML SDF

Formula

C13H24O6

Net Charge

Average Mass

276.32610

Monoisotopic Mass

276.15729

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

InChIKey

KBTQMAFDKPKMEJ-UYNYGYNWSA-N

SMILES

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

Metabolite of Species	Details
Pristionchus pacificus (NCBI:txid54126)	See: PubMed
Panagrellus redivivus (NCBI:txid6233)	Produced by female See: PubMed
Caenorhabditis elegans (NCBI:txid6239)	dauer inducing 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#1 (CHEBI:78786) has functional parent (6R)-6-hydroxyheptanoic acid (CHEBI:78775) ascr#1 (CHEBI:78786) has role Caenorhabditis elegans metabolite (CHEBI:78804) ascr#1 (CHEBI:78786) has role pheromone (CHEBI:26013) ascr#1 (CHEBI:78786) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205) ascr#1 (CHEBI:78786) is a monocarboxylic acid (CHEBI:25384) ascr#1 (CHEBI:78786) is conjugate acid of ascr#1(1−) (CHEBI:139614)

Incoming	ascr#1-CoA (CHEBI:139645) has functional parent ascr#1 (CHEBI:78786) glas#1 (CHEBI:79197) has functional parent ascr#1 (CHEBI:78786) icas#1 (CHEBI:79051) has functional parent ascr#1 (CHEBI:78786) ascr#1(1−) (CHEBI:139614) is conjugate base of ascr#1 (CHEBI:78786)

IUPAC Name

(6R)-6-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]heptanoic acid

Synonyms	Sources
(−)-6R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)heptanoic acid	SMID
(−)-6R-(3'R,5'R-dihydroxy-6'S-methyltetrahydro-pyran-2'-R-yloxy)heptanoic acid	ChEBI
(−)-daumone	ChEBI
asc-C7	ChEBI
ascaroside C7	ChEBI
daumone	ChEBI
daumone-1	SMID

Last Modified

24 January 2024