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CHEBI:139219 - N-[(2S,3S,4R)-1-(α-D-galactosyloxy)-3,4-dihydroxy-6-phenylhexan-2-yl]hexacosanamide

ChEBI IDCHEBI:139219
ChEBI NameN-[(2S,3S,4R)-1-(α-D-galactosyloxy)-3,4-dihydroxy-6-phenylhexan-2-yl]hexacosanamide
Stars
ASCII NameN-[(2S,3S,4R)-1-(alpha-D-galactosyloxy)-3,4-dihydroxy-6-phenylhexan-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 2-phenylethyl 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
FormulaC44H79NO9
Net Charge0
Average Mass766.114
Monoisotopic Mass765.57548
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)CCc1ccccc1
InChIInChI=1S/C44H79NO9/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-27-30-39(48)45-36(40(49)37(47)32-31-35-28-25-24-26-29-35)34-53-44-43(52)42(51)41(50)38(33-46)54-44/h24-26,28-29,36-38,40-44,46-47,49-52H,2-23,27,30-34H2,1H3,(H,45,48)/t36-,37+,38+,40-,41-,42-,43+,44-/m0/s1
InChIKeyXMIBGPITGPVDLO-UHTOCBDZSA-N
ChEBI Ontology
Outgoing Relation(s)
N-[(2S,3S,4R)-1-(α-D-galactosyloxy)-3,4-dihydroxy-6-phenylhexan-2-yl]hexacosanamide (CHEBI:139219) has functional parent α-D-galactose (CHEBI:28061)
N-[(2S,3S,4R)-1-(α-D-galactosyloxy)-3,4-dihydroxy-6-phenylhexan-2-yl]hexacosanamide (CHEBI:139219) is a α-galactosylceramide (CHEBI:132148)
IUPAC Name 
2,5,6-trideoxy-1-O-α-D-galactopyranosyl-2-(hexacosanoylamino)-6-phenyl-D-ribo-hexitol
Synonym  Source
N-[(2S,3S,4R)-1-(α-D-galactopyranosyloxy)-3,4-dihydroxy-6-phenylhexan-2-yl]hexacosanamideIUPAC
Manual XrefsDatabases
CA2683681Patent
Registry NumbersSources
Reaxys:18641314Reaxys
Citations