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CHEBI:79307 - glas#26

ChEBI IDCHEBI:79307
ChEBI Nameglas#26
Stars
DefinitionAn ascarosyloxycarboxylic acid β-D-glucopyranosyl ester resulting from the formal esterification of the carboxy group of ascr#26 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
FormulaC27H50O11
Net Charge0
Average Mass550.686
Monoisotopic Mass550.33531
SMILESC[C@H](CCCCCCCCCCCCC(=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/C27H50O11/c1-17(35-26-20(30)15-19(29)18(2)36-26)13-11-9-7-5-3-4-6-8-10-12-14-22(31)38-27-25(34)24(33)23(32)21(16-28)37-27/h17-21,23-30,32-34H,3-16H2,1-2H3/t17-,18+,19-,20-,21-,23-,24+,25-,26-,27+/m1/s1
InChIKeyGSRDQXYUFNVAAO-SEYCSDJLSA-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#26 (CHEBI:79307) has functional parent ascr#26 (CHEBI:78964)
glas#26 (CHEBI:79307) has role Caenorhabditis elegans metabolite (CHEBI:78804)
glas#26 (CHEBI:79307) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
glas#26 (CHEBI:79307) is a ascarosyloxycarboxylic acid β-D-glucopyranosyl ester (CHEBI:79198)
IUPAC Name 
1-O-{(14R)-14-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]pentadecanoyl}-β-D-glucopyranose
Synonym  Source
β-D-glucos-1''-yl-14R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-pentadecanoateSMID
Manual XrefsDatabases
glas%2326SMID
Registry NumbersSources
Reaxys:22233536Reaxys
CAS:1355683-65-6SMID
Citations