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CHEBI:139222 - N-[(2S,3S,4R)-1-(α-D-galactosyloxy)-3,4-dihydroxy-13-phenyltridecan-2-yl]hexacosanamide

ChEBI IDCHEBI:139222
ChEBI NameN-[(2S,3S,4R)-1-(α-D-galactosyloxy)-3,4-dihydroxy-13-phenyltridecan-2-yl]hexacosanamide
Stars
ASCII NameN-[(2S,3S,4R)-1-(alpha-D-galactosyloxy)-3,4-dihydroxy-13-phenyltridecan-2-yl]hexacosanamide
DefinitionAn α-galactosylceramide in which the nitrogen carries a hexacosanamido group and C-4 carries in addition to a hydroxy function a 9-phenylnonyl group. Essentially a phytosphingosine analogue with a truncated lipid chain terminating in a benzene ring, it has been used in investigations on the binding affinity of glycolipids to CD1d molecules.
Last Modified4 December 2017
SubmitterMarcus Ennis
DownloadsMolfile
FormulaC51H93NO9
Net Charge0
Average Mass864.303
Monoisotopic Mass863.68503
SMILESCCCCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO[C@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)[C@H](O)[C@H](O)CCCCCCCCCc1ccccc1
InChIInChI=1S/C51H93NO9/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-25-28-34-39-46(55)52-43(41-60-51-50(59)49(58)48(57)45(40-53)61-51)47(56)44(54)38-33-27-24-22-23-26-30-35-42-36-31-29-32-37-42/h29,31-32,36-37,43-45,47-51,53-54,56-59H,2-28,30,33-35,38-41H2,1H3,(H,52,55)/t43-,44+,45+,47-,48-,49-,50+,51-/m0/s1
InChIKeyCJEIKPQXBKGOLL-SVYZMDQNSA-N
ChEBI Ontology
Outgoing Relation(s)
N-[(2S,3S,4R)-1-(α-D-galactosyloxy)-3,4-dihydroxy-13-phenyltridecan-2-yl]hexacosanamide (CHEBI:139222) has functional parent α-D-galactose (CHEBI:28061)
N-[(2S,3S,4R)-1-(α-D-galactosyloxy)-3,4-dihydroxy-13-phenyltridecan-2-yl]hexacosanamide (CHEBI:139222) is a α-galactosylceramide (CHEBI:132148)
IUPAC Name 
N-[(2S,3S,4R)-1-(α-D-galactopyranosyloxy)-3,4-dihydroxy-13-phenyltridecan-2-yl]hexacosanamide
Synonym  Source
N-[(1S,2S,3R)-1-[(α-D-galactopyranosyloxy)methyl]-2,3-dihydroxy-9-phenylnonyl]hexacosanamideIUPAC
Registry NumbersSources
Reaxys:21036960Reaxys
Citations