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CHEBI:79145 - oscr#23

ChEBI IDCHEBI:79145
ChEBI Nameoscr#23
Stars
DefinitionAn ω-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (2E)-14-hydroxytetradec-2-enoic acid with ascarylopyranose (the α anomer). It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified23 February 2018
SubmitterGareth Owen
DownloadsMolfile
FormulaC20H36O6
Net Charge0
Average Mass372.502
Monoisotopic Mass372.25119
SMILESC[C@@H]1O[C@@H](OCCCCCCCCCCC/C=C/C(=O)O)[C@H](O)C[C@H]1O
InChIInChI=1S/C20H36O6/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/h11,13,16-18,20-22H,2-10,12,14-15H2,1H3,(H,23,24)/b13-11+/t16-,17+,18+,20+/m0/s1
InChIKeyDIYWZICECWKTIT-XKCSVMQCSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Detected in maoc-1(hj13) 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#23 (CHEBI:79145) has functional parent (2E)-14-hydroxytetradec-2-enoic acid (CHEBI:79167)
oscr#23 (CHEBI:79145) has role Caenorhabditis elegans metabolite (CHEBI:78804)
oscr#23 (CHEBI:79145) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
oscr#23 (CHEBI:79145) is a ω-hydroxy fatty acid ascaroside (CHEBI:79204)
oscr#23 (CHEBI:79145) is conjugate acid of oscr#23(1−) (CHEBI:140004)
Incoming Relation(s)
oscr#23-CoA (CHEBI:140005) has functional parent oscr#23 (CHEBI:79145)
oscr#23(1−) (CHEBI:140004) is conjugate base of oscr#23 (CHEBI:79145)
IUPAC Name 
(2E)-14-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]tetradec-2-enoic acid
Synonym  Source
14-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-tetradecenoic acidSMID
Manual XrefsDatabases
oscr%2323SMID
Registry NumbersSources
Reaxys:22233434Reaxys
CAS:1355682-20-0SMID
Citations