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CHEBI:79146 - oscr#24

ChEBI IDCHEBI:79146
ChEBI Nameoscr#24
Stars
DefinitionAn ω-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of 14-hydroxytetradecanoic acid (14-hydroxymyristic acid) with ascarylopyranose (the α anomer). It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified23 February 2018
SubmitterGareth Owen
DownloadsMolfile
FormulaC20H38O6
Net Charge0
Average Mass374.518
Monoisotopic Mass374.26684
SMILESC[C@@H]1O[C@@H](OCCCCCCCCCCCCCC(=O)O)[C@H](O)C[C@H]1O
InChIInChI=1S/C20H38O6/c1-16-17(21)15-18(22)20(26-16)25-14-12-10-8-6-4-2-3-5-7-9-11-13-19(23)24/h16-18,20-22H,2-15H2,1H3,(H,23,24)/t16-,17+,18+,20+/m0/s1
InChIKeyODXIHYQVXXYLQK-JRBPQWBISA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Detected in acox-1(ok2257), maoc-1(hj13), daf-22(ok693), and dhs-28(hj8) 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#24 (CHEBI:79146) has functional parent 14-hydroxymyristic acid (CHEBI:77168)
oscr#24 (CHEBI:79146) has role Caenorhabditis elegans metabolite (CHEBI:78804)
oscr#24 (CHEBI:79146) is a monocarboxylic acid (CHEBI:25384)
oscr#24 (CHEBI:79146) is a ω-hydroxy fatty acid ascaroside (CHEBI:79204)
oscr#24 (CHEBI:79146) is conjugate acid of oscr#24(1−) (CHEBI:140007)
Incoming Relation(s)
bhos#24 (CHEBI:79262) has functional parent oscr#24 (CHEBI:79146)
oscr#24-CoA (CHEBI:140008) has functional parent oscr#24 (CHEBI:79146)
oscr#24(1−) (CHEBI:140007) is conjugate base of oscr#24 (CHEBI:79146)
IUPAC Name 
14-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]tetradecanoic acid
Synonym  Source
14-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-tetradecanoic acidSMID
Manual XrefsDatabases
oscr%2324SMID
Registry NumbersSources
Reaxys:22233435Reaxys
CAS:1355682-20-0SMID
Citations