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CHEBI:79140 - oscr#18

ChEBI IDCHEBI:79140
ChEBI Nameoscr#18
Stars
DefinitionAn ω-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of 11-hydroxyundecanoic acid with ascarylopyranose (the α anomer). It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified1 March 2018
SubmitterGareth Owen
DownloadsMolfile
FormulaC17H32O6
Net Charge0
Average Mass332.437
Monoisotopic Mass332.21989
SMILESC[C@@H]1O[C@@H](OCCCCCCCCCCC(=O)O)[C@H](O)C[C@H]1O
InChIInChI=1S/C17H32O6/c1-13-14(18)12-15(19)17(23-13)22-11-9-7-5-3-2-4-6-8-10-16(20)21/h13-15,17-19H,2-12H2,1H3,(H,20,21)/t13-,14+,15+,17+/m0/s1
InChIKeyGEMAYWCAMMUVTD-KLZNWCGWSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Detected in wild type (N2) worms. It is a major ascaroside in acox-1(ok2257) mutant worms, and has also been 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#18 (CHEBI:79140) has functional parent 11-hydroxyundecanoic acid (CHEBI:79126)
oscr#18 (CHEBI:79140) has role Caenorhabditis elegans metabolite (CHEBI:78804)
oscr#18 (CHEBI:79140) is a monocarboxylic acid (CHEBI:25384)
oscr#18 (CHEBI:79140) is a ω-hydroxy fatty acid ascaroside (CHEBI:79204)
oscr#18 (CHEBI:79140) is conjugate acid of oscr#18(1−) (CHEBI:139987)
Incoming Relation(s)
bhos#18 (CHEBI:79259) has functional parent oscr#18 (CHEBI:79140)
icos#18 (CHEBI:79124) has functional parent oscr#18 (CHEBI:79140)
oscr#18-CoA (CHEBI:139988) has functional parent oscr#18 (CHEBI:79140)
oscr#18(1−) (CHEBI:139987) is conjugate base of oscr#18 (CHEBI:79140)
IUPAC Name 
11-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]undecanoic acid
Synonym  Source
11-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-undecanoic acidSMID
Manual XrefsDatabases
oscr%2318SMID
Registry NumbersSources
Reaxys:22233409Reaxys
CAS:1355682-09-5SMID
Citations