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CHEBI:79157 - oscr#35

ChEBI IDCHEBI:79157
ChEBI Nameoscr#35
Stars
DefinitionAn ω-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (2E)-20-hydroxyicos-2-enoic acid with ascarylopyranose (the α anomer). It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified20 February 2018
SubmitterGareth Owen
DownloadsMolfile
FormulaC26H48O6
Net Charge0
Average Mass456.664
Monoisotopic Mass456.34509
SMILESC[C@@H]1O[C@@H](OCCCCCCCCCCCCCCCCC/C=C/C(=O)O)[C@H](O)C[C@H]1O
InChIInChI=1S/C26H48O6/c1-22-23(27)21-24(28)26(32-22)31-20-18-16-14-12-10-8-6-4-2-3-5-7-9-11-13-15-17-19-25(29)30/h17,19,22-24,26-28H,2-16,18,20-21H2,1H3,(H,29,30)/b19-17+/t22-,23+,24+,26+/m0/s1
InChIKeyAIUNLQUMHTUTNR-YHGVQZPQSA-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#35 (CHEBI:79157) has functional parent (2E)-20-hydroxyicos-2-enoic acid (CHEBI:79184)
oscr#35 (CHEBI:79157) has role Caenorhabditis elegans metabolite (CHEBI:78804)
oscr#35 (CHEBI:79157) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
oscr#35 (CHEBI:79157) is a ω-hydroxy fatty acid ascaroside (CHEBI:79204)
oscr#35 (CHEBI:79157) is conjugate acid of oscr#35(1−) (CHEBI:140041)
Incoming Relation(s)
oscr#35-CoA (CHEBI:140042) has functional parent oscr#35 (CHEBI:79157)
oscr#35(1−) (CHEBI:140041) is conjugate base of oscr#35 (CHEBI:79157)
IUPAC Name 
(2E)-20-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]icos-2-enoic acid
Synonym  Source
20-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-icosenoic acidSMID
Manual XrefsDatabases
oscr%2335SMID
Registry NumbersSources
Reaxys:22233497Reaxys
CAS:1355682-41-5SMID
Citations