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CHEBI:79303 - glas#18

ChEBI IDCHEBI:79303
ChEBI Nameglas#18
Stars
DefinitionAn ascarosyloxycarboxylic acid β-D-glucopyranosyl ester resulting from the formal esterification of the carboxy group of ascr#18 with the anomeric hydroxy group of β-D-glucopyranose. It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified25 July 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC23H42O11
Net Charge0
Average Mass494.578
Monoisotopic Mass494.27271
SMILESC[C@H](CCCCCCCCC(=O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O
InChIInChI=1S/C23H42O11/c1-13(31-22-16(26)11-15(25)14(2)32-22)9-7-5-3-4-6-8-10-18(27)34-23-21(30)20(29)19(28)17(12-24)33-23/h13-17,19-26,28-30H,3-12H2,1-2H3/t13-,14+,15-,16-,17-,19-,20+,21-,22-,23+/m1/s1
InChIKeyQBDRWZBYGHVNSP-BZNPLBMASA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Detected in acox-1(ok2257) mutant worms.
Roles Classification
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)
glas#18 (CHEBI:79303) has functional parent ascr#18 (CHEBI:78955)
glas#18 (CHEBI:79303) has role Caenorhabditis elegans metabolite (CHEBI:78804)
glas#18 (CHEBI:79303) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
glas#18 (CHEBI:79303) is a ascarosyloxycarboxylic acid β-D-glucopyranosyl ester (CHEBI:79198)
IUPAC Name 
1-O-{(10R)-10-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]undecanoyl}-β-D-glucopyranose
Synonym  Source
β-D-glucos-1''-yl-10R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-undecanoateSMID
Manual XrefsDatabases
glas%2318SMID
Registry NumbersSources
Reaxys:22233522Reaxys
CAS:1355683-57-6SMID
Citations