CHEBI:78786 - ascr#1

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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 0
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 )
View more via ChEBI Ontology
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 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
ascaroside C7 ChEBI
daumone ChEBI
daumone-1 SMID
Manual Xrefs Databases
ascr%231%0D SMID
WO2005075491 Patent
View more database links
Registry Numbers Types Sources
10093613 Reaxys Registry Number Reaxys
690991-47-0 CAS Registry Number SMID
Citations Waiting for Citations Types Sources
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Last Modified
24 July 2014