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CHEBI:78821 - ascr#3

ChEBI IDCHEBI:78821
ChEBI Nameascr#3
Stars
DefinitionAn (ω−1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (2E,8R)-8-hydroxynon-2-enoic 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, and also synergises with ascr#2, ascr#4, and ascr#8 in male attraction.
Last Modified5 January 2021
SubmitterGareth Owen
DownloadsMolfile
FormulaC15H26O6
Net Charge0
Average Mass302.367
Monoisotopic Mass302.17294
SMILESC[C@H](CCCC/C=C/C(=O)O)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O
InChIInChI=1S/C15H26O6/c1-10(7-5-3-4-6-8-14(18)19)20-15-13(17)9-12(16)11(2)21-15/h6,8,10-13,15-17H,3-5,7,9H2,1-2H3,(H,18,19)/b8-6+/t10-,11+,12-,13-,15-/m1/s1
InChIKeyMWGRRKDIJLJLMO-OSYKULTDSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (18650807)
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#3 (CHEBI:78821) has functional parent (2E,8R)-8-hydroxynon-2-enoic acid (CHEBI:78819)
ascr#3 (CHEBI:78821) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ascr#3 (CHEBI:78821) has role pheromone (CHEBI:26013)
ascr#3 (CHEBI:78821) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ascr#3 (CHEBI:78821) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
ascr#3 (CHEBI:78821) is conjugate acid of ascr#3(1-) (CHEBI:139677)
Incoming Relation(s)
ascr#3-CoA (CHEBI:139705) has functional parent ascr#3 (CHEBI:78821)
glas#3 (CHEBI:79300) has functional parent ascr#3 (CHEBI:78821)
hbas#3 (CHEBI:79321) has functional parent ascr#3 (CHEBI:78821)
icas#3 (CHEBI:79052) has functional parent ascr#3 (CHEBI:78821)
mbas#3 (CHEBI:79128) has functional parent ascr#3 (CHEBI:78821)
ascr#3(1-) (CHEBI:139677) is conjugate base of ascr#3 (CHEBI:78821)
IUPAC Name 
(2E,8R)-8-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]non-2-enoic acid
Synonyms  Source
daumone-3SMID
(−)-8R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-nonenoic acidSMID
ascaroside C9ChEBI
Manual XrefsDatabases
ascr%233SMID
17226059ChemSpider
LMFA13040004LIPID MAPS
Registry NumbersSources
Reaxys:22233393Reaxys
CAS:946524-26-1SMID
Citations