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CHEBI:79305 - glas#22

ChEBI IDCHEBI:79305
ChEBI Nameglas#22
Stars
DefinitionAn ascarosyloxycarboxylic acid β-D-glucopyranosyl ester resulting from the formal esterification of the carboxy group of ascr#22 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
FormulaC25H46O11
Net Charge0
Average Mass522.632
Monoisotopic Mass522.30401
SMILESC[C@H](CCCCCCCCCCC(=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/C25H46O11/c1-15(33-24-18(28)13-17(27)16(2)34-24)11-9-7-5-3-4-6-8-10-12-20(29)36-25-23(32)22(31)21(30)19(14-26)35-25/h15-19,21-28,30-32H,3-14H2,1-2H3/t15-,16+,17-,18-,19-,21-,22+,23-,24-,25+/m1/s1
InChIKeyGPSYFHFACFTZSX-NGGGFPBGSA-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#22 (CHEBI:79305) has functional parent ascr#22 (CHEBI:78960)
glas#22 (CHEBI:79305) has role Caenorhabditis elegans metabolite (CHEBI:78804)
glas#22 (CHEBI:79305) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
glas#22 (CHEBI:79305) is a ascarosyloxycarboxylic acid β-D-glucopyranosyl ester (CHEBI:79198)
IUPAC Name 
1-O-{(12R)-12-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]tridecanoyl}-β-D-glucopyranose
Synonym  Source
β-D-glucos-1''-yl-12R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-tridecanoateSMID
Manual XrefsDatabases
glas%2322SMID
Registry NumbersSources
Reaxys:22233531Reaxys
CAS:1355683-61-2SMID
Citations