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CHEBI:79142 - oscr#20

ChEBI IDCHEBI:79142
ChEBI Nameoscr#20
Stars
DefinitionAn ω-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of 12-hydroxydodecanoic acid with ascarylopyranose (the α anomer). It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified1 March 2018
SubmitterGareth Owen
DownloadsMolfile
FormulaC18H34O6
Net Charge0
Average Mass346.464
Monoisotopic Mass346.23554
SMILESC[C@@H]1O[C@@H](OCCCCCCCCCCCC(=O)O)[C@H](O)C[C@H]1O
InChIInChI=1S/C18H34O6/c1-14-15(19)13-16(20)18(24-14)23-12-10-8-6-4-2-3-5-7-9-11-17(21)22/h14-16,18-20H,2-13H2,1H3,(H,21,22)/t14-,15+,16+,18+/m0/s1
InChIKeyHTPFVTWQRWJPNG-BVIKNXMNSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Detected 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#20 (CHEBI:79142) has functional parent 12-hydroxylauric acid (CHEBI:39567)
oscr#20 (CHEBI:79142) has role Caenorhabditis elegans metabolite (CHEBI:78804)
oscr#20 (CHEBI:79142) is a monocarboxylic acid (CHEBI:25384)
oscr#20 (CHEBI:79142) is a ω-hydroxy fatty acid ascaroside (CHEBI:79204)
oscr#20 (CHEBI:79142) is conjugate acid of oscr#20(1−) (CHEBI:139995)
Incoming Relation(s)
bhos#20 (CHEBI:79260) has functional parent oscr#20 (CHEBI:79142)
oscr#20-CoA (CHEBI:139996) has functional parent oscr#20 (CHEBI:79142)
oscr#20(1−) (CHEBI:139995) is conjugate base of oscr#20 (CHEBI:79142)
IUPAC Name 
12-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]dodecanoic acid
Synonyms  Source
12-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-dodecanoic acidSMID
12-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]lauric acidChEBI
Manual XrefsDatabases
oscr%2320SMID
Registry NumbersSources
Reaxys:22233416Reaxys
CAS:1355682-13-1SMID
Citations