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CHEBI:79136 - oscr#14

ChEBI IDCHEBI:79136
ChEBI Nameoscr#14
Stars
DefinitionAn ω-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of 8-hydroxyoctanoic acid with ascarylopyranose (the α anomer). It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified2 March 2018
SubmitterGareth Owen
DownloadsMolfile
FormulaC14H26O6
Net Charge0
Average Mass290.356
Monoisotopic Mass290.17294
SMILESC[C@@H]1O[C@@H](OCCCCCCCC(=O)O)[C@H](O)C[C@H]1O
InChIInChI=1S/C14H26O6/c1-10-11(15)9-12(16)14(20-10)19-8-6-4-2-3-5-7-13(17)18/h10-12,14-16H,2-9H2,1H3,(H,17,18)/t10-,11+,12+,14+/m0/s1
InChIKeyDJYKCDSAKUJQRP-FMCLSXCISA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Detected in dhs-28(hj8) and maoc-1(hj13) and is a major ascaroside in acox-1(ok2257) mutant worms.
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.
semiochemical  A molecular messenger released by an organism that affects the behaviour within or between species.
ChEBI Ontology
Outgoing Relation(s)
oscr#14 (CHEBI:79136) has functional parent 8-hydroxyoctanoic acid (CHEBI:79162)
oscr#14 (CHEBI:79136) has role Caenorhabditis elegans metabolite (CHEBI:78804)
oscr#14 (CHEBI:79136) is a monocarboxylic acid (CHEBI:25384)
oscr#14 (CHEBI:79136) is a ω-hydroxy fatty acid ascaroside (CHEBI:79204)
oscr#14 (CHEBI:79136) is conjugate acid of oscr#14(1−) (CHEBI:139975)
Incoming Relation(s)
oscr#14-CoA (CHEBI:139976) has functional parent oscr#14 (CHEBI:79136)
oscr#14(1−) (CHEBI:139975) is conjugate base of oscr#14 (CHEBI:79136)
IUPAC Name 
8-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]octanoic acid
Synonym  Source
8-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-octanoic acidSMID
Manual XrefsDatabases
oscr%2314SMID
Registry NumbersSources
Reaxys:22233392Reaxys
CAS:1355681-99-0SMID
Citations