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CHEBI:79300 - glas#3

ChEBI IDCHEBI:79300
ChEBI Nameglas#3
Stars
DefinitionAn ascarosyloxycarboxylic acid β-D-glucopyranosyl ester resulting from the formal esterification of the carboxy group of ascr#3 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
FormulaC21H36O11
Net Charge0
Average Mass464.508
Monoisotopic Mass464.22576
SMILESC[C@H](CCCC/C=C/C(=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/C21H36O11/c1-11(29-20-14(24)9-13(23)12(2)30-20)7-5-3-4-6-8-16(25)32-21-19(28)18(27)17(26)15(10-22)31-21/h6,8,11-15,17-24,26-28H,3-5,7,9-10H2,1-2H3/b8-6+/t11-,12+,13-,14-,15-,17-,18+,19-,20-,21+/m1/s1
InChIKeyUSHOVWZTBFBUPQ-AHQKKNCYSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Detected in acox-1 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#3 (CHEBI:79300) has functional parent ascr#3 (CHEBI:78821)
glas#3 (CHEBI:79300) has role Caenorhabditis elegans metabolite (CHEBI:78804)
glas#3 (CHEBI:79300) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
glas#3 (CHEBI:79300) is a ascarosyloxycarboxylic acid β-D-glucopyranosyl ester (CHEBI:79198)
glas#3 (CHEBI:79300) is a α,β-unsaturated carboxylic ester (CHEBI:51737)
IUPAC Name 
1-O-{(2E,8R)-8-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]non-2-enoyl}-β-D-glucopyranose
Synonym  Source
β-D-glucos-1''-yl-8R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-nonenoateSMID
Manual XrefsDatabases
glas%233SMID
Registry NumbersSources
Reaxys:22233503Reaxys
CAS:1355683-53-2SMID
Citations