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CHEBI:79302 - glas#16

ChEBI IDCHEBI:79302
ChEBI Nameglas#16
Stars
DefinitionAn ascarosyloxycarboxylic acid β-D-glucopyranosyl ester resulting from the formal esterification of the carboxy group of ascr#16 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
FormulaC22H40O11
Net Charge0
Average Mass480.551
Monoisotopic Mass480.25706
SMILESC[C@H](CCCCCCCC(=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/C22H40O11/c1-12(30-21-15(25)10-14(24)13(2)31-21)8-6-4-3-5-7-9-17(26)33-22-20(29)19(28)18(27)16(11-23)32-22/h12-16,18-25,27-29H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,18-,19+,20-,21-,22+/m1/s1
InChIKeyYGECYZAESCGRDN-XXPWOUKKSA-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#16 (CHEBI:79302) has functional parent ascr#16 (CHEBI:78950)
glas#16 (CHEBI:79302) has role Caenorhabditis elegans metabolite (CHEBI:78804)
glas#16 (CHEBI:79302) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
glas#16 (CHEBI:79302) is a ascarosyloxycarboxylic acid β-D-glucopyranosyl ester (CHEBI:79198)
IUPAC Name 
1-O-{(9R)-9-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]decanoyl}-β-D-glucopyranose
Synonym  Source
β-D-glucos-1''-yl-9R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-decanoateSMID
Manual XrefsDatabases
glas%2316SMID
Registry NumbersSources
Reaxys:22233515Reaxys
CAS:1355683-55-4SMID
Citations