1.0 2011-09-21 00:04:24 UTC 2015-07-21 06:56:49 UTC FDB021878 3-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]-Tetracosanamide 3-O-SulfO-beta-D-galactosylceramide 3-O-SulfO-beta-delta-galactosylceramide 3-O-Sulfogalactosylceramide 3-O-Sulphogalactosylceramide 3'-O-Sulphogalactosylceramide 3'-Sulfogalactosylceramide 3'-Sulphogalactosylceramide Cerebroside 3-sulfate Cerebroside 3-sulphate Galactosylceramide-sulfate Galactosylceramide-sulphate Galactosylceramidesulfate Galactosylceramidesulphate N-[(1S,2R,3E)-2-hydroxy-1-[[(3-O-sulfo-b-D-galactopyranosyl)oxy]methyl]-3-heptadecen-1-yl]-Tetracosanamide N-[(1S,2R,3E)-2-hydroxy-1-[[(3-O-sulfo-b-D-galactopyranosyl)oxy]methyl]-3-heptadecenyl]-Tetracosanamide N-[(1S,2R,3E)-2-hydroxy-1-[[(3-O-sulfo-beta-delta-galactopyranosyl)oxy]methyl]-3-heptadecen-1-yl]-Tetracosanamide N-[(1S,2R,3E)-2-hydroxy-1-[[(3-O-sulfo-beta-delta-galactopyranosyl)oxy]methyl]-3-heptadecenyl]-Tetracosanamide Sulfatide Sulfatide (d18:1/24:0) Tetracosanoyl sulfatide Tetracosanoyl sulphatide C48H93NO11S 892.317 891.646933513 [(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 acid 3'-sulfogalactosylceramide 151122-71-3 CCCCCCCCCCCCCCCCCCCCCCCC(=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\CCCCCCCCCCCCC InChI=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/s1 MEAZTWJVOWHKJM-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. Glycosphingolipids Organic compounds Lipids and lipid-like molecules Sphingolipids Glycosphingolipids Aliphatic heteromonocyclic compounds Acetals Alkyl glycosides Alkyl sulfates Carboximidic acids Fatty acyl glycosides of mono- and disaccharides Hexoses Hydrocarbon derivatives O-glycosyl compounds Organic oxides Organonitrogen compounds Organopnictogen compounds Oxacyclic compounds Oxanes Primary alcohols Propargyl-type 1,3-dipolar organic compounds Secondary alcohols Sulfuric acid monoesters Acetal Alcohol Aliphatic heteromonocyclic compound Alkyl glycoside Alkyl sulfate Carboximidic acid Carboximidic acid derivative Fatty acyl Fatty acyl glycoside Fatty acyl glycoside of mono- or disaccharide Glycosphingolipid Glycosyl compound Hexose monosaccharide Hydrocarbon derivative Monosaccharide O-glycosyl compound Organic 1,3-dipolar compound Organic nitrogen compound Organic oxide Organic oxygen compound Organic sulfuric acid or derivatives Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Oxacycle Oxane Primary alcohol Propargyl-type 1,3-dipolar organic compound Secondary alcohol Sulfate-ester Sulfuric acid ester Sulfuric acid monoester N-acyl-beta-D-galactosylsphingosine galactosylceramide sulfate Solid logp 6.01 ALOGPS logs -6.63 ALOGPS solubility 2.09e-04 g/l ALOGPS logp 10.65 ChemAxon pka_strongest_acidic -1.9 ChemAxon pka_strongest_basic 0.025 ChemAxon iupac [(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 acid ChemAxon average_mass 892.317 ChemAxon mono_mass 891.646933513 ChemAxon smiles CCCCCCCCCCCCCCCCCCCCCCCC(=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\CCCCCCCCCCCCC ChemAxon formula C48H93NO11S ChemAxon inchi InChI=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/s1 ChemAxon inchikey MEAZTWJVOWHKJM-CIAPRIGGSA-N ChemAxon polar_surface_area 192.08 ChemAxon refractivity 244.99 ChemAxon polarizability 111.22 ChemAxon rotatable_bond_count 43 ChemAxon acceptor_count 10 ChemAxon donor_count 6 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Sphingolipid Metabolism SMP00034 map00500 Specdb::NmrOneD 311811 Specdb::NmrOneD 311812 Specdb::NmrOneD 311813 Specdb::NmrOneD 311814 Specdb::NmrOneD 311815 Specdb::NmrOneD 311816 Specdb::NmrOneD 311817 Specdb::NmrOneD 311818 Specdb::NmrOneD 311819 Specdb::NmrOneD 311820 Specdb::NmrOneD 311821 Specdb::NmrOneD 311822 Specdb::NmrOneD 311823 Specdb::NmrOneD 311824 Specdb::NmrOneD 311825 Specdb::NmrOneD 311826 Specdb::NmrOneD 311827 Specdb::NmrOneD 311828 Specdb::NmrOneD 311829 Specdb::NmrOneD 311830 Specdb::MsMs 41828 Specdb::MsMs 41829 Specdb::MsMs 41830 Specdb::MsMs 42536 Specdb::MsMs 42537 Specdb::MsMs 42538 HMDB00024 #<Reference:0x000055ce32030ba0> #<Reference:0x000055ce320309e8> #<Reference:0x000055ce32030830> #<Reference:0x000055ce32030678> #<Reference:0x000055ce320304c0> #<Reference:0x000055ce32030308> #<Reference:0x000055ce32030150> #<Reference:0x000055ce3202bf60> #<Reference:0x000055ce3202bda8> #<Reference:0x000055ce3202bbf0> #<Reference:0x000055ce3202ba38> #<Reference:0x000055ce3202b880> #<Reference:0x000055ce3202b6c8> #<Reference:0x000055ce3202b510> #<Reference:0x000055ce3202b358> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823 Acid ceramidase Q13510 ASAH1 ADAMTS-like protein 1 Q8N6G6 ADAMTSL1 Alkaline ceramidase 1 Q8TDN7 ACER1 Alkaline ceramidase 2 Q5QJU3 ACER2 Antigen-presenting glycoprotein CD1d P15813 CD1D Beta-1,3-galactosyltransferase 5 Q9Y2C3 B3GALT5 Ceramide glucosyltransferase Q16739 UGCG Ceramide synthase 1 P27544 CERS1 Collagen type IV alpha-3-binding protein Q9Y5P4 COL4A3BP Epididymal secretory protein E1 P61916 NPC2 Galactocerebrosidase P54803 GALC Galactosylceramide sulfotransferase Q99999 GAL3ST1 Ganglioside GM2 activator P17900 GM2A Glucosylceramidase P04062 GBA GPI ethanolamine phosphate transferase 1 O95427 PIGN GPI ethanolamine phosphate transferase 2 Q5H8A4 PIGG GPI ethanolamine phosphate transferase 3 Q8TEQ8 PIGO GPI mannosyltransferase 1 Q9H3S5 PIGM GPI mannosyltransferase 2 Q9NUD9 PIGV GPI mannosyltransferase 3 Q92521 PIGB GPI mannosyltransferase 4 Q86VD9 PIGZ GPI transamidase component PIG-S Q96S52 PIGS GPI transamidase component PIG-T Q969N2 PIGT GPI-anchor transamidase Q92643 PIGK L-selectin P14151 SELL Lactosylceramide 1,3-N-acetyl-beta-D-glucosaminyltransferase Q9BYG0 B3GNT5 Lactosylceramide 4-alpha-galactosyltransferase Q9NPC4 A4GALT Myelin basic protein P02686 MBP N-acetylglucosaminyl-phosphatidylinositol de-N-acetylase Q9Y2B2 PIGL Neutral ceramidase Q9NR71 ASAH2 Non-lysosomal glucosylceramidase Q9HCG7 GBA2 P-selectin P16109 SELP Phosphatidylinositol glycan anchor biosynthesis class U protein Q9H490 PIGU Phosphatidylinositol N-acetylglucosaminyltransferase subunit A P37287 PIGA Phosphatidylinositol N-acetylglucosaminyltransferase subunit C Q92535 PIGC Phosphatidylinositol N-acetylglucosaminyltransferase subunit H Q14442 PIGH Phosphatidylinositol N-acetylglucosaminyltransferase subunit P P57054 PIGP Phosphatidylinositol N-acetylglucosaminyltransferase subunit Q Q9BRB3 PIGQ Phosphatidylinositol N-acetylglucosaminyltransferase subunit Y Q3MUY2 PIGY Phosphatidylinositol-glycan biosynthesis class F protein Q07326 PIGF Phosphatidylinositol-glycan biosynthesis class W protein Q7Z7B1 PIGW Phosphatidylinositol-glycan biosynthesis class X protein Q8TBF5 PIGX Proactivator polypeptide P07602 PSAP Putative neutral ceramidase C P0C7U2 ASAH2C Sphingomyelin phosphodiesterase P17405 SMPD1 T-cell surface glycoprotein CD1e, membrane-associated P15812 CD1E