1.02011-09-21 01:41:48 UTC2015-07-21 06:59:28 UTCFDB028575Ganglioside GM2 (d18:0/25:0)Ganglioside GM2 (d18:0/25:0) is a ganglioside. Ganglioside is a compound composed of a glycosphingolipid (ceramide and oligosaccharide) with one or more sialic acids (AKA n-acetylneuraminic acid, NANA) linked on the sugar chain. The 60+ known gangliosides differ mainly in the position and number of NANA residues.
It is a component of the cell plasma membrane that modulates cell signal transduction events. It appears that they concentrate in lipid rafts.
They have recently been found to be highly important in immunology. Natural and semisynthetic gangliosides are considered possible therapeutics for neurodegenerative disorders.[1]
Gangliosides are more complex glycosphingolipids in which oligosaccharide chains containing N-acetylneuraminic acid (NeuNAc) are attached to a ceramide. NeuNAc, an acetylated derivative of the carbohydrate sialic acid, makes the head groups of Gangliosides anionic. NB: the M in GM2 stands for monosialo, i.e., one NeuNAc residue. GM2 is the second monosialo ganglioside characterized, thus the subscript 2. Their structural diversity results from variation in the composition and sequence of the sugar residues. In all Gangliosides, the ceramide is linked through its C-1 to a beta-glucosyl residue, which, in turn, is bound to a beta-galactosyl residue. [Wikipedia]
Particularly, Ganglioside GM2 (d18:0/25:0) is a GM2 ganglioside. A 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 GM2 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. G(M2) Ganglioside accumulates due to a deficiency of hexosaminidase A or B (beta-N-acetylhexosaminidase), or GM2 activator protein, resulting in Gangliosidoses. Gangliosidoses include heredity metabolic disorders that include Tay-Sachs disease and Sandhoff disease. Gangliosides GM2 is especially common in the nervous tissue of the brain. In the United States, about 1 in 27 to 1 in 30 Ashkenazi Jews is a recessive carrier. French Canadians and the Cajun community of Louisiana have an occurrence similar to the Ashkenazi Jews.
Gangliosides are glycosphingolipids. There are four types of glycosphingolipids, the cerebrosides, sulfatides, globosides and gangliosides. Gangliosides are very similar to globosides except that they also contain N-acetyl neuraminic acid (NANA) in varying amounts. The specific names for the gangliosides provide information about their structure. The letter G refers to ganglioside, and the subscripts M, D, T and Q indicate that the molecule contains mono-, di-, tri and quatra-sialic acid. The numbered subscripts 1, 2 and 3 refer to the carbohydrate sequence that is attached to the ceramide. In particular, 1 stands for GalGalNAcGalGlc-ceramide, 2 stands for GalNAcGalGlc-ceramide and 3 stands for GalGlc-ceramide. Deficiencies in lysosomal enzymes that degrade the carbohydrate portions of various gangliosides are responsible for a number of lysosomal storage diseases such as Tay-Sachs disease, Sandhoff disease, and GM1 gangliosidosis. The carbohydrate portion of the ganglioside GM1 is the site of attachment of cholera toxin, the protein secreted by Vibrio cholerae. [HMDB]C75H138N2O261483.8961482.953782598(2S,4S,5R)-2-{[(2R,3S,4R,5R,6S)-3-{[(2S,3R,4R,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(2-oxopropyl)oxan-2-yl]oxy}-6-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2S,3R)-3-hydroxy-2-pentacosanamidooctadecyl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-5-hydroxy-2-(hydroxymethyl)oxan-4-yl]oxy}-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid(2S,4S,5R)-2-{[(2R,3S,4R,5R,6S)-3-{[(2S,3R,4R,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(2-oxopropyl)oxan-2-yl]oxy}-6-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2S,3R)-3-hydroxy-2-pentacosanamidooctadecyl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-5-hydroxy-2-(hydroxymethyl)oxan-4-yl]oxy}-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acidCCCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O[C@@H]3O[C@H](CO)[C@H](O)[C@H](O)[C@H]3CC(C)=O)[C@H](O[C@@]3(C[C@H](O)[C@@H](NC(C)=O)C(O3)[C@H](O)[C@H](O)CO)C(O)=O)[C@H]2O)[C@H](O)[C@H]1O)[C@H](O)CCCCCCCCCCCCCCCInChI=1S/C75H138N2O26/c1-5-7-9-11-13-15-17-19-20-21-22-23-24-25-26-27-29-31-33-35-37-39-41-59(87)77-52(53(84)40-38-36-34-32-30-28-18-16-14-12-10-8-6-2)48-96-72-65(92)64(91)67(57(46-80)98-72)100-73-66(93)70(68(58(47-81)99-73)101-71-51(42-49(3)82)61(88)63(90)56(45-79)97-71)103-75(74(94)95)43-54(85)60(76-50(4)83)69(102-75)62(89)55(86)44-78/h51-58,60-73,78-81,84-86,88-93H,5-48H2,1-4H3,(H,76,83)(H,77,87)(H,94,95)/t51-,52+,53-,54+,55-,56-,57-,58-,60-,61-,62-,63+,64-,65-,66-,67-,68+,69?,70-,71+,72-,73+,75+/m1/s1MQUXYIIALDERRJ-ZAQASFACSA-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 compoundsAcetamidesAlkyl glycosidesC-glucuronidesC-glycosyl compoundsCarboxylic acidsHydrocarbon derivativesKetalsKetonesMonocarboxylic acids and derivativesN-acyl aminesN-acylneuraminic acidsNeuraminic acidsO-glycosyl compoundsOligosaccharidesOrganic oxidesOrganonitrogen compoundsOrganopnictogen compoundsOxacyclic compoundsOxanesPolyolsPrimary alcoholsPyransSecondary alcoholsSecondary carboxylic acid amidesAcetalAcetamideAlcoholAliphatic heteromonocyclic compoundAlkyl glycosideC-glucuronideC-glycosyl compoundCarbonyl groupCarboxamide groupCarboxylic acidCarboxylic acid derivativeFatty acylFatty acyl glycosideFatty amideGlycosphingolipidGlycosyl compoundHydrocarbon derivativeKetalKetoneMonocarboxylic acid or derivativesN-acyl-amineN-acylneuraminic acidN-acylneuraminic acid or derivativesNeuraminic acidO-glycosyl compoundOligosaccharideOrganic nitrogen compoundOrganic oxideOrganic oxygen compoundOrganoheterocyclic compoundOrganonitrogen compoundOrganooxygen compoundOrganopnictogen compoundOxacycleOxanePolyolPrimary alcoholPyranSecondary alcoholSecondary carboxylic acid amideSolidlogp4.32logs-4.75solubility2.62e-02 g/llogp8.09pka_strongest_acidic2.82pka_strongest_basic-3.5iupac(2S,4S,5R)-2-{[(2R,3S,4R,5R,6S)-3-{[(2S,3R,4R,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(2-oxopropyl)oxan-2-yl]oxy}-6-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2S,3R)-3-hydroxy-2-pentacosanamidooctadecyl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-5-hydroxy-2-(hydroxymethyl)oxan-4-yl]oxy}-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acidaverage_mass1483.896mono_mass1482.953782598smilesCCCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O[C@@H]3O[C@H](CO)[C@H](O)[C@H](O)[C@H]3CC(C)=O)[C@H](O[C@@]3(C[C@H](O)[C@@H](NC(C)=O)C(O3)[C@H](O)[C@H](O)CO)C(O)=O)[C@H]2O)[C@H](O)[C@H]1O)[C@H](O)CCCCCCCCCCCCCCCformulaC75H138N2O26inchiInChI=1S/C75H138N2O26/c1-5-7-9-11-13-15-17-19-20-21-22-23-24-25-26-27-29-31-33-35-37-39-41-59(87)77-52(53(84)40-38-36-34-32-30-28-18-16-14-12-10-8-6-2)48-96-72-65(92)64(91)67(57(46-80)98-72)100-73-66(93)70(68(58(47-81)99-73)101-71-51(42-49(3)82)61(88)63(90)56(45-79)97-71)103-75(74(94)95)43-54(85)60(76-50(4)83)69(102-75)62(89)55(86)44-78/h51-58,60-73,78-81,84-86,88-93H,5-48H2,1-4H3,(H,76,83)(H,77,87)(H,94,95)/t51-,52+,53-,54+,55-,56-,57-,58-,60-,61-,62-,63+,64-,65-,66-,67-,68+,69?,70-,71+,72-,73+,75+/m1/s1inchikeyMQUXYIIALDERRJ-ZAQASFACSA-Npolar_surface_area449.4refractivity376.66polarizability171.64rotatable_bond_count58acceptor_count26donor_count16physiological_charge-1formal_charge0Specdb::MsMs2281933Specdb::MsMs2281934Specdb::MsMs2281935Specdb::MsMs3084253Specdb::MsMs3084254Specdb::MsMs3084255HMDB11906AnatidaeType 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 scrofa9823Alpha-N-acetylneuraminide alpha-2,8-sialyltransferaseQ92185ST8SIA1Antigen-presenting glycoprotein CD1dP15813CD1DBeta-1,3-galactosyltransferase 4O96024B3GALT4Beta-1,3-galactosyltransferase 5Q9Y2C3B3GALT5Beta-1,4 N-acetylgalactosaminyltransferase 1Q00973B4GALNT1Epididymal secretory protein E1P61916NPC2Ganglioside GM2 activatorP17900GM2AGPI 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 transamidaseQ92643PIGKLactosylceramide 1,3-N-acetyl-beta-D-glucosaminyltransferaseQ9BYG0B3GNT5Lactosylceramide alpha-2,3-sialyltransferaseQ9UNP4ST3GAL5N-acetylglucosaminyl-phosphatidylinositol de-N-acetylaseQ9Y2B2PIGLNon-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 proteinQ8TBF5PIGXSialidase-3Q9UQ49NEU3T-cell surface glycoprotein CD1e, membrane-associatedP15812CD1E