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CHEBI:79144 - oscr#22

ChEBI IDCHEBI:79144
ChEBI Nameoscr#22
Stars
DefinitionAn ω-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of 13-hydroxytridecanoic acid with ascarylopyranose (the α anomer). It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified23 February 2018
SubmitterGareth Owen
DownloadsMolfile
FormulaC19H36O6
Net Charge0
Average Mass360.491
Monoisotopic Mass360.25119
SMILESC[C@@H]1O[C@@H](OCCCCCCCCCCCCC(=O)O)[C@H](O)C[C@H]1O
InChIInChI=1S/C19H36O6/c1-15-16(20)14-17(21)19(25-15)24-13-11-9-7-5-3-2-4-6-8-10-12-18(22)23/h15-17,19-21H,2-14H2,1H3,(H,22,23)/t15-,16+,17+,19+/m0/s1
InChIKeyBMAOWSPJJLOKGM-DODZYUBVSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Detected in wild type (N2) and 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#22 (CHEBI:79144) has functional parent 13-hydroxytridecanoic acid (CHEBI:79166)
oscr#22 (CHEBI:79144) has role Caenorhabditis elegans metabolite (CHEBI:78804)
oscr#22 (CHEBI:79144) is a monocarboxylic acid (CHEBI:25384)
oscr#22 (CHEBI:79144) is a ω-hydroxy fatty acid ascaroside (CHEBI:79204)
oscr#22 (CHEBI:79144) is conjugate acid of oscr#22(1−) (CHEBI:140001)
Incoming Relation(s)
bhos#22 (CHEBI:79261) has functional parent oscr#22 (CHEBI:79144)
oscr#22-CoA (CHEBI:140002) has functional parent oscr#22 (CHEBI:79144)
oscr#22(1−) (CHEBI:140001) is conjugate base of oscr#22 (CHEBI:79144)
IUPAC Name 
13-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]tridecanoic acid
Synonym  Source
13-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-tridecanoic acidSMID
Manual XrefsDatabases
oscr%2322%0DSMID
Registry NumbersSources
Reaxys:22233426Reaxys
CAS:1355682-18-6SMID
Citations