1.02011-09-21 00:04:51 UTC2017-03-11 23:00:17 UTCFDB021900GlucosylceramideA glycosphingolipid (ceramide and oligosaccharide)or oligoglycosylceramide with one or more sialic acids (i.e. n-acetylneuraminic acid) linked on the sugar chain. It is a component the cell plasma membrane which modulates cell signal transduction events. Gangliosides have been found to be highly important in immunology. Ganglioside GL1a carries a net-negative charge at pH 7.0 and is acidic. Gangliosides can amount to 6% of the weight of lipids from brain, but they are found at low levels in all animal tissues.
Cerebrosides are glycosphingolipids. There are four types of glycosphingolipids, the cerebrosides, sulfatides, globosides and gangliosides. Cerebrosides have a single sugar group linked to ceramide. The most common are galactocerebrosides (containing galactose), the least common are glucocerebrosides (containing glucose). Galactocerebrosides are found predominantly in neuronal cell membranes. In contrast glucocerebrosides are not normally found in membranes. Instead, they are typically intermediates in the synthesis or degradation of more complex glycosphingolipids. Galactocerebrosides are synthesized from ceramide and UDP-galactose. Excess lysosomal accumulation of glucocerebrosides is found in Gaucher disease. [HMDB]1-O-b-D-Glucopyranosyl-ceramide1-O-beta-delta-Glucopyranosyl-ceramideGanglioside gl1aGaucher cerebrosideGlc-beta1->1'cerGlcCeramideGlucocerebrosideC48H93NO8812.2539811.690118957N-[(2S,3R,4E)-3-hydroxy-1-{[(2R,3R,4S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octadec-4-en-2-yl]tetracosanamideN-[(2S,3R,4E)-3-hydroxy-1-{[(2R,3R,4S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octadec-4-en-2-yl]tetracosanamide85305-87-9CCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO[C@@H]1O[C@H](CO)C(O)[C@H](O)[C@H]1O)[C@H](O)\C=C\CCCCCCCCCCCCCInChI=1S/C48H93NO8/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-26-28-30-32-34-36-38-44(52)49-41(40-56-48-47(55)46(54)45(53)43(39-50)57-48)42(51)37-35-33-31-29-27-25-16-14-12-10-8-6-4-2/h35,37,41-43,45-48,50-51,53-55H,3-34,36,38-40H2,1-2H3,(H,49,52)/b37-35+/t41-,42+,43+,45?,46-,47+,48+/m0/s1POQRWMRXUOPCLD-XNWFPASESA-N belongs to the class of organic compounds known as glycosyl-n-acylsphingosines. Glycosyl-N-acylsphingosines are compounds containing a sphingosine linked to a simple glucosyl moiety.Glycosyl-N-acylsphingosinesOrganic compoundsLipids and lipid-like moleculesSphingolipidsGlycosphingolipidsAliphatic heteromonocyclic compoundsAcetalsAlkyl glycosidesCarbonyl compoundsFatty acyl glycosides of mono- and disaccharidesHexosesHydrocarbon derivativesN-acyl aminesO-glycosyl compoundsOrganic oxidesOrganonitrogen compoundsOrganopnictogen compoundsOxacyclic compoundsOxanesPolyolsPrimary alcoholsSecondary alcoholsSecondary carboxylic acid amidesAcetalAlcoholAliphatic heteromonocyclic compoundAlkyl glycosideCarbonyl groupCarboxamide groupCarboxylic acid derivativeFatty acylFatty acyl glycosideFatty acyl glycoside of mono- or disaccharideFatty amideGlycosyl compoundGlycosyl-n-acylsphingosineHexose monosaccharideHydrocarbon derivativeMonosaccharideN-acyl-amineO-glycosyl compoundOrganic nitrogen compoundOrganic oxideOrganic oxygen compoundOrganoheterocyclic compoundOrganonitrogen compoundOrganooxygen compoundOrganopnictogen compoundOxacycleOxanePolyolPrimary alcoholSecondary alcoholSecondary carboxylic acid amideSolidlogp9.15logs-6.64solubility1.86e-04 g/llogp12.65pka_strongest_acidic12.18pka_strongest_basic0.019iupacN-[(2S,3R,4E)-3-hydroxy-1-{[(2R,3R,4S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octadec-4-en-2-yl]tetracosanamideaverage_mass812.2539mono_mass811.690118957smilesCCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO[C@@H]1O[C@H](CO)C(O)[C@H](O)[C@H]1O)[C@H](O)\C=C\CCCCCCCCCCCCCformulaC48H93NO8inchiInChI=1S/C48H93NO8/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-26-28-30-32-34-36-38-44(52)49-41(40-56-48-47(55)46(54)45(53)43(39-50)57-48)42(51)37-35-33-31-29-27-25-16-14-12-10-8-6-4-2/h35,37,41-43,45-48,50-51,53-55H,3-34,36,38-40H2,1-2H3,(H,49,52)/b37-35+/t41-,42+,43+,45?,46-,47+,48+/m0/s1inchikeyPOQRWMRXUOPCLD-XNWFPASESA-Npolar_surface_area148.71refractivity235polarizability105.5rotatable_bond_count41acceptor_count8donor_count6physiological_charge0formal_charge0Sphingolipid MetabolismSMP00034map00500Specdb::MsMs54198Specdb::MsMs54199Specdb::MsMs54200Specdb::MsMs129315Specdb::MsMs129316Specdb::MsMs129317HMDB00140Acid ceramidaseQ13510ASAH1Alkaline ceramidase 1Q8TDN7ACER1Alkaline ceramidase 2Q5QJU3ACER2Antigen-presenting glycoprotein CD1dP15813CD1DBeta-1,3-galactosyltransferase 5Q9Y2C3B3GALT5Beta-galactosidaseP16278GLB1Ceramide glucosyltransferaseQ16739UGCGCeramide synthase 1P27544CERS1Collagen type IV alpha-3-binding proteinQ9Y5P4COL4A3BPEpididymal secretory protein E1P61916NPC2GalactocerebrosidaseP54803GALCGanglioside GM2 activatorP17900GM2AGlucosylceramidaseP04062GBAGPI ethanolamine phosphate transferase 1O95427PIGNGPI ethanolamine phosphate transferase 2Q5H8A4PIGGGPI ethanolamine phosphate transferase 3Q8TEQ8PIGOGPI mannosyltransferase 1Q9H3S5PIGMGPI mannosyltransferase 2Q9NUD9PIGVGPI mannosyltransferase 3Q92521PIGBGPI mannosyltransferase 4Q86VD9PIGZGPI transamidase component PIG-SQ96S52PIGSGPI transamidase component PIG-TQ969N2PIGTGPI-anchor transamidaseQ92643PIGKLactase-phlorizin hydrolaseP09848LCTLactosylceramide 1,3-N-acetyl-beta-D-glucosaminyltransferaseQ9BYG0B3GNT5N-acetylglucosaminyl-phosphatidylinositol de-N-acetylaseQ9Y2B2PIGLNeutral ceramidaseQ9NR71ASAH2Non-lysosomal glucosylceramidaseQ9HCG7GBA2Phosphatidylinositol glycan anchor biosynthesis class U proteinQ9H490PIGUPhosphatidylinositol N-acetylglucosaminyltransferase subunit AP37287PIGAPhosphatidylinositol N-acetylglucosaminyltransferase subunit CQ92535PIGCPhosphatidylinositol N-acetylglucosaminyltransferase subunit HQ14442PIGHPhosphatidylinositol N-acetylglucosaminyltransferase subunit PP57054PIGPPhosphatidylinositol N-acetylglucosaminyltransferase subunit QQ9BRB3PIGQPhosphatidylinositol N-acetylglucosaminyltransferase subunit YQ3MUY2PIGYPhosphatidylinositol-glycan biosynthesis class F proteinQ07326PIGFPhosphatidylinositol-glycan biosynthesis class W proteinQ7Z7B1PIGWPhosphatidylinositol-glycan biosynthesis class X proteinQ8TBF5PIGXPutative neutral ceramidase CP0C7U2ASAH2CSphingomyelin phosphodiesteraseP17405SMPD1T-cell surface glycoprotein CD1e, membrane-associatedP15812CD1E