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CHEBI:79151 - oscr#29

ChEBI IDCHEBI:79151
ChEBI Nameoscr#29
Stars
DefinitionAn ω-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (2E)-17-hydroxyheptadec-2-enoic acid with ascarylopyranose (the α anomer). It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified20 February 2018
SubmitterGareth Owen
DownloadsMolfile
FormulaC23H42O6
Net Charge0
Average Mass414.583
Monoisotopic Mass414.29814
SMILESC[C@@H]1O[C@@H](OCCCCCCCCCCCCCC/C=C/C(=O)O)[C@H](O)C[C@H]1O
InChIInChI=1S/C23H42O6/c1-19-20(24)18-21(25)23(29-19)28-17-15-13-11-9-7-5-3-2-4-6-8-10-12-14-16-22(26)27/h14,16,19-21,23-25H,2-13,15,17-18H2,1H3,(H,26,27)/b16-14+/t19-,20+,21+,23+/m0/s1
InChIKeyHJPCXYKWUOGDSW-KRSIWRBNSA-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#29 (CHEBI:79151) has functional parent (2E)-17-hydroxyheptadec-2-enoic acid (CHEBI:79175)
oscr#29 (CHEBI:79151) has role Caenorhabditis elegans metabolite (CHEBI:78804)
oscr#29 (CHEBI:79151) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
oscr#29 (CHEBI:79151) is a ω-hydroxy fatty acid ascaroside (CHEBI:79204)
oscr#29 (CHEBI:79151) is conjugate acid of oscr#29(1−) (CHEBI:140022)
Incoming Relation(s)
oscr#29-CoA (CHEBI:140023) has functional parent oscr#29 (CHEBI:79151)
oscr#29(1−) (CHEBI:140022) is conjugate base of oscr#29 (CHEBI:79151)
IUPAC Name 
(2E)-17-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]heptadec-2-enoic acid
Synonym  Source
17-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-heptadecenoic acidSMID
Manual XrefsDatabases
oscr%2329SMID
Registry NumbersSources
Reaxys:22233459Reaxys
CAS:1355682-31-3SMID
Citations