1.02011-09-21 00:04:24 UTC2015-07-21 06:56:49 UTCFDB0218783-O-Sulfogalactosylceramide (d18:1/24:0)3-O-Sulfogalactosylceramide is an acidic, sulfated glycosphingolipid, often known as sulfatide. This lipid occurs in membranes of various cell types, but is found in particularly high concentrations in myelin where it constitutes 3-4% of total membrane lipids. This lipid is synthesized primarily in the oligodendrocytes in the central nervous system. Accumulation of this lipid in the lysosomes is a characteristic of metachromatic leukodystrophy, a lysosomal storage disease caused by the deficiency of arylsulfatase A. Alterations in sulfatide metabolism, trafficking, and homeostasis are present in the earliest clinically recognizable stages of Alzheimer's disease.
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.
Sulfatides are glycosphingolipids. There are four types of glycosphingolipids, the cerebrosides, sulfatides, globosides and gangliosides. Sulfatides are the sulfuric acid esters of galactocerebrosides. They are synthesized from galactocerebrosides and activated sulfate, 3'-phosphoadenosine 5'-phosphosulfate (PAPS). [HMDB][R-[R*,S*-(E)]]-N-[2-hydroxy-1-[[(3-O-sulfo-b-D-galactopyranosyl)oxy]methyl]-3-heptadecenyl]-Tetracosanamide[R-[R*,S*-(E)]]-N-[2-hydroxy-1-[[(3-O-sulfo-beta-delta-galactopyranosyl)oxy]methyl]-3-heptadecenyl]-Tetracosanamide3-O-SulfO-beta-D-galactosylceramide3-O-SulfO-beta-delta-galactosylceramide3-O-Sulfogalactosylceramide3-O-Sulphogalactosylceramide3'-O-Sulphogalactosylceramide3'-Sulfogalactosylceramide3'-SulphogalactosylceramideCerebroside 3-sulfateCerebroside 3-sulphateGalactosylceramide-sulfateGalactosylceramide-sulphateGalactosylceramidesulfateGalactosylceramidesulphateN-[(1S,2R,3E)-2-hydroxy-1-[[(3-O-sulfo-b-D-galactopyranosyl)oxy]methyl]-3-heptadecen-1-yl]-TetracosanamideN-[(1S,2R,3E)-2-hydroxy-1-[[(3-O-sulfo-b-D-galactopyranosyl)oxy]methyl]-3-heptadecenyl]-TetracosanamideN-[(1S,2R,3E)-2-hydroxy-1-[[(3-O-sulfo-beta-delta-galactopyranosyl)oxy]methyl]-3-heptadecen-1-yl]-TetracosanamideN-[(1S,2R,3E)-2-hydroxy-1-[[(3-O-sulfo-beta-delta-galactopyranosyl)oxy]methyl]-3-heptadecenyl]-TetracosanamideSulfatideSulfatide (d18:1/24:0)Tetracosanoyl sulfatideTetracosanoyl sulphatideC48H93NO11S892.317891.646933513[(2R,3R,4S,5S,6R)-3,5-dihydroxy-2-{[(2S,3R,4E)-3-hydroxy-2-tetracosanamidooctadec-4-en-1-yl]oxy}-6-(hydroxymethyl)oxan-4-yl]oxidanesulfonic acid3'-sulfogalactosylceramide151122-71-3CCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO[C@@H]1O[C@H](CO)[C@H](O)[C@H](OS(O)(=O)=O)[C@H]1O)[C@H](O)\C=C\CCCCCCCCCCCCCInChI=1S/C48H93NO11S/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(42(51)37-35-33-31-29-27-25-16-14-12-10-8-6-4-2)40-58-48-46(54)47(60-61(55,56)57)45(53)43(39-50)59-48/h35,37,41-43,45-48,50-51,53-54H,3-34,36,38-40H2,1-2H3,(H,49,52)(H,55,56,57)/b37-35+/t41-,42+,43+,45-,46+,47-,48+/m0/s1MEAZTWJVOWHKJM-CIAPRIGGSA-N belongs to the class of organic compounds known as glycosphingolipids. These are sphingolipids containing a saccharide moiety glycosidically attached to the sphingoid base. Although saccharide moieties are mostly O-glycosidically linked to the ceramide moiety, other sphingolipids with glycosidic bonds of other types (e.g. S-,C-, or N-type) has been reported.GlycosphingolipidsOrganic compoundsLipids and lipid-like moleculesSphingolipidsGlycosphingolipidsAliphatic heteromonocyclic compoundsAcetalsAlkyl glycosidesAlkyl sulfatesCarboximidic acidsFatty acyl glycosides of mono- and disaccharidesHexosesHydrocarbon derivativesO-glycosyl compoundsOrganic oxidesOrganonitrogen compoundsOrganopnictogen compoundsOxacyclic compoundsOxanesPrimary alcoholsPropargyl-type 1,3-dipolar organic compoundsSecondary alcoholsSulfuric acid monoestersAcetalAlcoholAliphatic heteromonocyclic compoundAlkyl glycosideAlkyl sulfateCarboximidic acidCarboximidic acid derivativeFatty acylFatty acyl glycosideFatty acyl glycoside of mono- or disaccharideGlycosphingolipidGlycosyl compoundHexose monosaccharideHydrocarbon derivativeMonosaccharideO-glycosyl compoundOrganic 1,3-dipolar compoundOrganic nitrogen compoundOrganic oxideOrganic oxygen compoundOrganic sulfuric acid or derivativesOrganoheterocyclic compoundOrganonitrogen compoundOrganooxygen compoundOrganopnictogen compoundOxacycleOxanePrimary alcoholPropargyl-type 1,3-dipolar organic compoundSecondary alcoholSulfate-esterSulfuric acid esterSulfuric acid monoesterN-acyl-beta-D-galactosylsphingosinegalactosylceramide sulfateSolidlogp6.01logs-6.63solubility2.09e-04 g/llogp10.65pka_strongest_acidic-1.9pka_strongest_basic0.025iupac[(2R,3R,4S,5S,6R)-3,5-dihydroxy-2-{[(2S,3R,4E)-3-hydroxy-2-tetracosanamidooctadec-4-en-1-yl]oxy}-6-(hydroxymethyl)oxan-4-yl]oxidanesulfonic acidaverage_mass892.317mono_mass891.646933513smilesCCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO[C@@H]1O[C@H](CO)[C@H](O)[C@H](OS(O)(=O)=O)[C@H]1O)[C@H](O)\C=C\CCCCCCCCCCCCCformulaC48H93NO11SinchiInChI=1S/C48H93NO11S/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(42(51)37-35-33-31-29-27-25-16-14-12-10-8-6-4-2)40-58-48-46(54)47(60-61(55,56)57)45(53)43(39-50)59-48/h35,37,41-43,45-48,50-51,53-54H,3-34,36,38-40H2,1-2H3,(H,49,52)(H,55,56,57)/b37-35+/t41-,42+,43+,45-,46+,47-,48+/m0/s1inchikeyMEAZTWJVOWHKJM-CIAPRIGGSA-Npolar_surface_area192.08refractivity244.99polarizability111.22rotatable_bond_count43acceptor_count10donor_count6physiological_charge-1formal_charge0Sphingolipid MetabolismSMP00034map00500Specdb::NmrOneD311811Specdb::NmrOneD311812Specdb::NmrOneD311813Specdb::NmrOneD311814Specdb::NmrOneD311815Specdb::NmrOneD311816Specdb::NmrOneD311817Specdb::NmrOneD311818Specdb::NmrOneD311819Specdb::NmrOneD311820Specdb::NmrOneD311821Specdb::NmrOneD311822Specdb::NmrOneD311823Specdb::NmrOneD311824Specdb::NmrOneD311825Specdb::NmrOneD311826Specdb::NmrOneD311827Specdb::NmrOneD311828Specdb::NmrOneD311829Specdb::NmrOneD311830Specdb::MsMs41828Specdb::MsMs41829Specdb::MsMs41830Specdb::MsMs42536Specdb::MsMs42537Specdb::MsMs42538HMDB00024#<Reference:0x00005556760e3bf8>#<Reference:0x00005556760e38d8>#<Reference:0x00005556760e3658>#<Reference:0x00005556760e3428>#<Reference:0x00005556760e31f8>#<Reference:0x00005556760e2d20>#<Reference:0x00005556760e2b40>#<Reference:0x00005556760e2910>#<Reference:0x00005556760e2708>#<Reference:0x00005556760e2488>#<Reference:0x00005556760e2208>#<Reference:0x00005556760e2000>#<Reference:0x00005556760e1c68>#<Reference:0x00005556760e1ab0>#<Reference:0x00005556760e18f8>AnatidaeType 1specificAnatidae8830BeefaloType 1specificBos taurus X Bison bison297284BisonType 1specificBison bison9901BuffaloType 1specificBubalus bubalis89462Cattle (Beef, Veal)Type 1specificBos taurus9913ChickenType 1specificGallus gallus9031Columbidae (Dove, Pigeon)Type 1specificColumbidae8930DeerType 1specificCervidae9850Domestic goatType 1specificCapra aegagrus hircus9925Domestic pigType 1specificSus scrofa domestica9825ElkType 1specificCervus canadensis1574408EmuType 1specificDromaius novaehollandiae8790European rabbitType 1specificOryctolagus9984Greylag gooseType 1specificAnser anser8843Guinea henType 1specificNumida meleagris8996HorseType 1specificEquus caballus9796Mallard duckType 1specificAnas platyrhynchos8839Mountain hareType 1specificLepus timidus62621Mule deerType 1specificOdocoileus9871OstrichType 1specificStruthio camelus8801PheasantType 1specificPhasianus colchicus9054QuailType 1specificPhasianidae9005RabbitType 1specificLeporidae9979Rock ptarmiganType 1specificLagopus muta64668Sheep (Mutton, Lamb)Type 1specificOvis aries9940SquabType 1specificColumba8931TurkeyType 1specificMeleagris gallopavo9103Velvet duckType 1specificMelanitta fusca371864Wild boarType 1specificSus scrofa9823Acid ceramidaseQ13510ASAH1ADAMTS-like protein 1Q8N6G6ADAMTSL1Alkaline ceramidase 1Q8TDN7ACER1Alkaline ceramidase 2Q5QJU3ACER2Antigen-presenting glycoprotein CD1dP15813CD1DBeta-1,3-galactosyltransferase 5Q9Y2C3B3GALT5Ceramide glucosyltransferaseQ16739UGCGCeramide synthase 1P27544CERS1Collagen type IV alpha-3-binding proteinQ9Y5P4COL4A3BPEpididymal secretory protein E1P61916NPC2GalactocerebrosidaseP54803GALCGalactosylceramide sulfotransferaseQ99999GAL3ST1Ganglioside 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 transamidaseQ92643PIGKL-selectinP14151SELLLactosylceramide 1,3-N-acetyl-beta-D-glucosaminyltransferaseQ9BYG0B3GNT5Lactosylceramide 4-alpha-galactosyltransferaseQ9NPC4A4GALTMyelin basic proteinP02686MBPN-acetylglucosaminyl-phosphatidylinositol de-N-acetylaseQ9Y2B2PIGLNeutral ceramidaseQ9NR71ASAH2Non-lysosomal glucosylceramidaseQ9HCG7GBA2P-selectinP16109SELPPhosphatidylinositol 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 proteinQ8TBF5PIGXProactivator polypeptideP07602PSAPPutative neutral ceramidase CP0C7U2ASAH2CSphingomyelin phosphodiesteraseP17405SMPD1T-cell surface glycoprotein CD1e, membrane-associatedP15812CD1E