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CHEBI:79158 - oscr#36

ChEBI IDCHEBI:79158
ChEBI Nameoscr#36
Stars
DefinitionAn ω-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of 20-hydroxyicosanoic acid (20-hydroxyarachidic acid) with ascarylopyranose (the α anomer). It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified19 February 2018
SubmitterGareth Owen
DownloadsMolfile
FormulaC26H50O6
Net Charge0
Average Mass458.680
Monoisotopic Mass458.36074
SMILESC[C@@H]1O[C@@H](OCCCCCCCCCCCCCCCCCCCC(=O)O)[C@H](O)C[C@H]1O
InChIInChI=1S/C26H50O6/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/h22-24,26-28H,2-21H2,1H3,(H,29,30)/t22-,23+,24+,26+/m0/s1
InChIKeyNALXHMIWEUPQCH-POMLREGLSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Detected in 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#36 (CHEBI:79158) has functional parent 20-hydroxyicosanoic acid (CHEBI:79190)
oscr#36 (CHEBI:79158) has role Caenorhabditis elegans metabolite (CHEBI:78804)
oscr#36 (CHEBI:79158) is a monocarboxylic acid (CHEBI:25384)
oscr#36 (CHEBI:79158) is a ω-hydroxy fatty acid ascaroside (CHEBI:79204)
oscr#36 (CHEBI:79158) is conjugate acid of oscr#36(1−) (CHEBI:140044)
Incoming Relation(s)
bhos#36 (CHEBI:79268) has functional parent oscr#36 (CHEBI:79158)
oscr#36-CoA (CHEBI:140045) has functional parent oscr#36 (CHEBI:79158)
oscr#36(1−) (CHEBI:140044) is conjugate base of oscr#36 (CHEBI:79158)
IUPAC Name 
20-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]icosanoic acid
Synonyms  Source
20-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-icosanoic acidSMID
20-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]eicosanoic acidChEBI
Manual XrefsDatabases
oscr%2336SMID
Registry NumbersSources
Reaxys:22233507Reaxys
CAS:1355682-43-7SMID
Citations