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CHEBI:131181 - (2R)-23-oxotetracosan-2-yl α-L-ascaroside

ChEBI IDCHEBI:131181
ChEBI Name(2R)-23-oxotetracosan-2-yl α-L-ascaroside
Stars
ASCII Name(2R)-23-oxotetracosan-2-yl alpha-L-ascaroside
DefinitionA hydroxy ketone ascaroside obtained by obtained by formal condensation of the 23-hydroxy group of (23R)-23-hydroxytetracosan-2-one with ascarylopyranose (the α-anomer). It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified21 July 2016
SubmitterGareth Owen
DownloadsMolfile
FormulaC30H58O5
Net Charge0
Average Mass498.789
Monoisotopic Mass498.42842
SMILESCC(=O)CCCCCCCCCCCCCCCCCCCC[C@@H](C)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O
InChIInChI=1S/C30H58O5/c1-25(31)22-20-18-16-14-12-10-8-6-4-5-7-9-11-13-15-17-19-21-23-26(2)34-30-29(33)24-28(32)27(3)35-30/h26-30,32-33H,4-24H2,1-3H3/t26-,27+,28-,29-,30-/m1/s1
InChIKeyHLVUFIHMCJNYEA-ONBQWJCTSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (23163760)
Roles Classification
Biological Role:
Caenorhabditis elegans metabolite  A nematode metabolite produced by Caenorhabditis elegans.
ChEBI Ontology
Outgoing Relation(s)
(2R)-23-oxotetracosan-2-yl α-L-ascaroside (CHEBI:131181) has role Caenorhabditis elegans metabolite (CHEBI:78804)
(2R)-23-oxotetracosan-2-yl α-L-ascaroside (CHEBI:131181) is a hydroxy ketone ascaroside (CHEBI:79201)
(2R)-23-oxotetracosan-2-yl α-L-ascaroside (CHEBI:131181) is a methyl ketone (CHEBI:51867)
IUPAC Name 
(2R)-23-oxotetracosan-2-yl 3,6-dideoxy-α-L-arabino-hexopyranoside
Synonym  Source
(23R)-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-tetracosan-2-oneChEBI