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CHEBI:79155 - oscr#33

ChEBI IDCHEBI:79155
ChEBI Nameoscr#33
Stars
DefinitionAn ω-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (2E)-19-hydroxynonadec-2-enoic acid with ascarylopyranose (the α anomer). It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified20 February 2018
SubmitterGareth Owen
DownloadsMolfile
FormulaC25H46O6
Net Charge0
Average Mass442.637
Monoisotopic Mass442.32944
SMILESC[C@@H]1O[C@@H](OCCCCCCCCCCCCCCCC/C=C/C(=O)O)[C@H](O)C[C@H]1O
InChIInChI=1S/C25H46O6/c1-21-22(26)20-23(27)25(31-21)30-19-17-15-13-11-9-7-5-3-2-4-6-8-10-12-14-16-18-24(28)29/h16,18,21-23,25-27H,2-15,17,19-20H2,1H3,(H,28,29)/b18-16+/t21-,22+,23+,25+/m0/s1
InChIKeyJXUDLBNWOUZIRD-KBTOCMJJSA-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#33 (CHEBI:79155) has functional parent (2E)-19-hydroxynonadec-2-enoic acid (CHEBI:79180)
oscr#33 (CHEBI:79155) has role Caenorhabditis elegans metabolite (CHEBI:78804)
oscr#33 (CHEBI:79155) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
oscr#33 (CHEBI:79155) is a ω-hydroxy fatty acid ascaroside (CHEBI:79204)
oscr#33 (CHEBI:79155) is conjugate acid of oscr#33(1−) (CHEBI:140035)
Incoming Relation(s)
oscr#33-CoA (CHEBI:140036) has functional parent oscr#33 (CHEBI:79155)
oscr#33(1−) (CHEBI:140035) is conjugate base of oscr#33 (CHEBI:79155)
IUPAC Name 
(2E)-19-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]nonadec-2-enoic acid
Synonym  Source
19-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-nonadecenoic acidSMID
Manual XrefsDatabases
oscr%2333SMID
Registry NumbersSources
Reaxys:22233488Reaxys
CAS:1355682-37-9SMID
Citations