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CHEBI:79304 - glas#20

ChEBI IDCHEBI:79304
ChEBI Nameglas#20
Stars
DefinitionAn ascarosyloxycarboxylic acid β-D-glucopyranosyl ester resulting from the formal esterification of the carboxy group of ascr#20 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
FormulaC24H44O11
Net Charge0
Average Mass508.605
Monoisotopic Mass508.28836
SMILESC[C@H](CCCCCCCCCC(=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/C24H44O11/c1-14(32-23-17(27)12-16(26)15(2)33-23)10-8-6-4-3-5-7-9-11-19(28)35-24-22(31)21(30)20(29)18(13-25)34-24/h14-18,20-27,29-31H,3-13H2,1-2H3/t14-,15+,16-,17-,18-,20-,21+,22-,23-,24+/m1/s1
InChIKeyVJWJXLJAPFOFKF-QENFJQAJSA-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#20 (CHEBI:79304) has functional parent ascr#20 (CHEBI:78958)
glas#20 (CHEBI:79304) has role Caenorhabditis elegans metabolite (CHEBI:78804)
glas#20 (CHEBI:79304) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
glas#20 (CHEBI:79304) is a ascarosyloxycarboxylic acid β-D-glucopyranosyl ester (CHEBI:79198)
IUPAC Name 
1-O-{(11R)-11-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]dodecanoyl}-β-D-glucopyranose
Synonym  Source
β-D-glucos-1''-yl-11R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-dodecanoateSMID
Manual XrefsDatabases
glas%2320SMID
Registry NumbersSources
Reaxys:22233525Reaxys
CAS:1355683-59-8SMID
Citations