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CHEBI:79147 - oscr#25

ChEBI IDCHEBI:79147
ChEBI Nameoscr#25
Stars
DefinitionAn ω-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (2E)-15-hydroxypentadec-2-enoic acid with ascarylopyranose (the α anomer). It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified23 February 2018
SubmitterGareth Owen
DownloadsMolfile
FormulaC21H38O6
Net Charge0
Average Mass386.529
Monoisotopic Mass386.26684
SMILESC[C@@H]1O[C@@H](OCCCCCCCCCCCC/C=C/C(=O)O)[C@H](O)C[C@H]1O
InChIInChI=1S/C21H38O6/c1-17-18(22)16-19(23)21(27-17)26-15-13-11-9-7-5-3-2-4-6-8-10-12-14-20(24)25/h12,14,17-19,21-23H,2-11,13,15-16H2,1H3,(H,24,25)/b14-12+/t17-,18+,19+,21+/m0/s1
InChIKeyFOEYOFVRRORADU-KMIVUYPQSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Detected in acox-1(ok2257), 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#25 (CHEBI:79147) has functional parent (2E)-15-hydroxypentadec-2-enoic acid (CHEBI:79168)
oscr#25 (CHEBI:79147) has role Caenorhabditis elegans metabolite (CHEBI:78804)
oscr#25 (CHEBI:79147) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
oscr#25 (CHEBI:79147) is a ω-hydroxy fatty acid ascaroside (CHEBI:79204)
oscr#25 (CHEBI:79147) is conjugate acid of oscr#25(1−) (CHEBI:140010)
Incoming Relation(s)
oscr#25-CoA (CHEBI:140011) has functional parent oscr#25 (CHEBI:79147)
oscr#25(1−) (CHEBI:140010) is conjugate base of oscr#25 (CHEBI:79147)
IUPAC Name 
(2E)-15-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]pentadec-2-enoic acid
Synonym  Source
15-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-pentadecenoic acidSMID
Manual XrefsDatabases
oscr%2325SMID
Registry NumbersSources
Reaxys:22233444Reaxys
CAS:1355682-23-3SMID
Citations