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CHEBI:78786 - ascr#1

ChEBI IDCHEBI:78786
ChEBI Nameascr#1
Stars
DefinitionAn (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.
Last Modified24 January 2024
SubmitterGareth Owen
DownloadsMolfile
FormulaC13H24O6
Net Charge0
Average Mass276.329
Monoisotopic Mass276.15729
SMILESC[C@H](CCCCC(=O)O)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O
InChIInChI=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
InChIKeyKBTQMAFDKPKMEJ-UYNYGYNWSA-N
Species of MetaboliteComponentSourceComments
Panagrellus redivivus (ncbitaxon:6233) - PubMed (23213209) Produced by female
Pristionchus pacificus (ncbitaxon:54126) - PubMed (23161728)
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (15690045) dauer inducing
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
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.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
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  Source
(−)-daumoneChEBI
daumoneChEBI
(−)-6R-(3'R,5'R-dihydroxy-6'S-methyltetrahydro-pyran-2'-R-yloxy)heptanoic acidChEBI
daumone-1SMID
(−)-6R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)heptanoic acidSMID
ascaroside C7ChEBI
Manual XrefsDatabases
ascr%231%0DSMID
WO2005075491Patent
LMFA13040002LIPID MAPS
Registry NumbersSources
Reaxys:10093613Reaxys
CAS:690991-47-0SMID
Citations