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CHEBI:79148 - oscr#26

ChEBI IDCHEBI:79148
ChEBI Nameoscr#26
Stars
DefinitionAn ω-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of 15-hydroxypentadecanoic acid with ascarylopyranose (the α anomer). It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified23 February 2018
SubmitterGareth Owen
DownloadsMolfile
FormulaC21H40O6
Net Charge0
Average Mass388.545
Monoisotopic Mass388.28249
SMILESC[C@@H]1O[C@@H](OCCCCCCCCCCCCCCC(=O)O)[C@H](O)C[C@H]1O
InChIInChI=1S/C21H40O6/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/h17-19,21-23H,2-16H2,1H3,(H,24,25)/t17-,18+,19+,21+/m0/s1
InChIKeyPWLVZSHZFIGCNL-QEUVDIPISA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Detected in wild type (N2) worms and also in acox-1(ok2257), maoc-1(hj13), daf-22(ok693), 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#26 (CHEBI:79148) has functional parent 15-hydroxypentadecanoic acid (CHEBI:79169)
oscr#26 (CHEBI:79148) has role Caenorhabditis elegans metabolite (CHEBI:78804)
oscr#26 (CHEBI:79148) is a monocarboxylic acid (CHEBI:25384)
oscr#26 (CHEBI:79148) is a ω-hydroxy fatty acid ascaroside (CHEBI:79204)
oscr#26 (CHEBI:79148) is conjugate acid of oscr#26(1−) (CHEBI:140013)
Incoming Relation(s)
bhos#26 (CHEBI:79263) has functional parent oscr#26 (CHEBI:79148)
oscr#26-CoA (CHEBI:140014) has functional parent oscr#26 (CHEBI:79148)
oscr#26(1−) (CHEBI:140013) is conjugate base of oscr#26 (CHEBI:79148)
IUPAC Name 
15-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]pentadecanoic acid
Synonym  Source
15-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-pentadecanoic acidSMID
Manual XrefsDatabases
oscr%2326SMID
Registry NumbersSources
Reaxys:22233449Reaxys
CAS:1355682-25-5SMID
Citations