1.02011-09-21 00:30:40 UTC2015-07-21 06:57:44 UTCFDB023493Ganglioside GA1 (d18:1/16:0)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 GA1 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.
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]C60H110N2O231227.5151226.749937836N-[(2S,3R)-1-{[(2R,4R,5S,6R)-5-{[(2S,3R,4R,5R,6R)-3,4-dihydroxy-5-{[(2S,3R,4R,5R,6R)-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-hydroxyoctadec-4-en-2-yl]hexadecanimidic acidN-[(2S,3R)-1-{[(2R,4R,5S,6R)-5-{[(2S,3R,4R,5R,6R)-3,4-dihydroxy-5-{[(2S,3R,4R,5R,6R)-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-hydroxyoctadec-4-en-2-yl]hexadecanimidic acid[H][C@@](CO[C@]1([H])O[C@]([H])(CO)[C@@]([H])(O[C@]2([H])O[C@]([H])(CO)[C@]([H])(O[C@]3([H])O[C@]([H])(CO)[C@]([H])(O)[C@]([H])(O[C@]4([H])O[C@]([H])(CO)[C@]([H])(O)[C@]([H])(O)[C@@]4([H])O)[C@@]3([H])NC(C)=O)[C@]([H])(O)[C@@]2([H])O)[C@]([H])(O)C1O)(NC(=O)CCCCCCCCCCCCCCC)[C@]([H])(O)C=CCCCCCCCCCCCCCInChI=1S/C60H110N2O23/c1-4-6-8-10-12-14-16-18-20-22-24-26-28-30-39(68)38(62-44(69)31-29-27-25-23-21-19-17-15-13-11-9-7-5-2)36-78-58-52(76)49(73)55(42(34-65)81-58)84-60-53(77)50(74)54(43(35-66)82-60)83-57-45(61-37(3)67)56(47(71)41(33-64)79-57)85-59-51(75)48(72)46(70)40(32-63)80-59/h28,30,38-43,45-60,63-66,68,70-77H,4-27,29,31-36H2,1-3H3,(H,61,67)(H,62,69)/t38-,39+,40+,41+,42+,43+,45+,46-,47-,48-,49+,50+,51+,52?,53+,54-,55+,56+,57-,58+,59-,60-/m0/s1OJVSVTBGNHQDJH-ZEUNAGBASA-N belongs to the class of organic compounds known as acyl coas. These are organic compounds containing a coenzyme A substructure linked to an acyl chain.Acyl CoAsOrganic compoundsLipids and lipid-like moleculesFatty AcylsFatty acyl thioestersAromatic heteropolycyclic compounds6-aminopurinesAmino acidsAminopyrimidines and derivativesAzacyclic compoundsBenzene and substituted derivativesBeta amino acids and derivativesCarbonyl compoundsCarbothioic S-estersCarboxylic acidsCoenzyme A and derivativesGlycosylaminesHeteroaromatic compoundsHydrocarbon derivativesHydroxy fatty acidsImidolactamsMonoalkyl phosphatesMonocarboxylic acids and derivativesMonosaccharide phosphatesN-acyl aminesN-substituted imidazolesOrganic oxidesOrganic pyrophosphatesOrganopnictogen compoundsOxacyclic compoundsPentose phosphatesPhenylpropanoic acidsPrimary aminesPurine ribonucleoside diphosphatesRibonucleoside 3'-phosphatesSecondary alcoholsSecondary carboxylic acid amidesSulfenyl compoundsTetrahydrofuransThia fatty acidsThioesters3-phenylpropanoic-acid6-aminopurineAlcoholAlkyl phosphateAmineAmino acidAmino acid or derivativesAminopyrimidineAromatic heteropolycyclic compoundAzacycleAzoleBenzenoidBeta amino acid or derivativesCarbonyl groupCarbothioic s-esterCarboxamide groupCarboxylic acidCarboxylic acid derivativeCoenzyme a or derivativesFatty amideGlycosyl compoundHeteroaromatic compoundHydrocarbon derivativeHydroxy fatty acidImidazoleImidazopyrimidineImidolactamMonoalkyl phosphateMonocarboxylic acid or derivativesMonocyclic benzene moietyMonosaccharideMonosaccharide phosphateN-acyl-amineN-glycosyl compoundN-substituted imidazoleOrganic nitrogen compoundOrganic oxideOrganic oxygen compoundOrganic phosphoric acid derivativeOrganic pyrophosphateOrganoheterocyclic compoundOrganonitrogen compoundOrganooxygen compoundOrganopnictogen compoundOrganosulfur compoundOxacyclePentose monosaccharidePentose phosphatePentose-5-phosphatePhosphoric acid esterPrimary aminePurinePurine ribonucleoside 3',5'-bisphosphatePurine ribonucleoside bisphosphatePurine ribonucleoside diphosphatePyrimidineRibonucleoside 3'-phosphateSecondary alcoholSecondary carboxylic acid amideSulfenyl compoundTetrahydrofuranThia fatty acidThiocarboxylic acid esterThiocarboxylic acid or derivativesSolidlogp3.69logs-4.43solubility4.57e-02 g/llogp5.13pka_strongest_acidic5.34pka_strongest_basic2.6iupacN-[(2S,3R)-1-{[(2R,4R,5S,6R)-5-{[(2S,3R,4R,5R,6R)-3,4-dihydroxy-5-{[(2S,3R,4R,5R,6R)-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-hydroxyoctadec-4-en-2-yl]hexadecanimidic acidaverage_mass1227.515mono_mass1226.749937836smiles[H][C@@](CO[C@]1([H])O[C@]([H])(CO)[C@@]([H])(O[C@]2([H])O[C@]([H])(CO)[C@]([H])(O[C@]3([H])O[C@]([H])(CO)[C@]([H])(O)[C@]([H])(O[C@]4([H])O[C@]([H])(CO)[C@]([H])(O)[C@]([H])(O)[C@@]4([H])O)[C@@]3([H])NC(C)=O)[C@]([H])(O)[C@@]2([H])O)[C@]([H])(O)C1O)(NC(=O)CCCCCCCCCCCCCCC)[C@]([H])(O)C=CCCCCCCCCCCCCCformulaC60H110N2O23inchiInChI=1S/C60H110N2O23/c1-4-6-8-10-12-14-16-18-20-22-24-26-28-30-39(68)38(62-44(69)31-29-27-25-23-21-19-17-15-13-11-9-7-5-2)36-78-58-52(76)49(73)55(42(34-65)81-58)84-60-53(77)50(74)54(43(35-66)82-60)83-57-45(61-37(3)67)56(47(71)41(33-64)79-57)85-59-51(75)48(72)46(70)40(32-63)80-59/h28,30,38-43,45-60,63-66,68,70-77H,4-27,29,31-36H2,1-3H3,(H,61,67)(H,62,69)/t38-,39+,40+,41+,42+,43+,45+,46-,47-,48-,49+,50+,51+,52?,53+,54-,55+,56+,57-,58+,59-,60-/m0/s1inchikeyOJVSVTBGNHQDJH-ZEUNAGBASA-Npolar_surface_area402.01refractivity307.57polarizability137.76rotatable_bond_count43acceptor_count25donor_count15physiological_charge0formal_charge0HMDB04902#<Reference:0x00005556741df798>#<Reference:0x00005556741df5e0>#<Reference:0x00005556741df428>#<Reference:0x00005556741df1f8>#<Reference:0x00005556741deff0>#<Reference:0x00005556741dee38>#<Reference:0x00005556741dec30>#<Reference:0x00005556741dea78>#<Reference:0x00005556741de8c0>#<Reference:0x00005556741de708>#<Reference:0x00005556741de500>#<Reference:0x00005556741de2f8>#<Reference:0x00005556741de050>#<Reference:0x00005556741ddd80>#<Reference:0x00005556741ddb00>#<Reference:0x00005556741dd8a8>#<Reference:0x00005556741dd5b0>#<Reference:0x00005556741dd3a8>#<Reference:0x00005556741dd1f0>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 scrofa9823Beta-galactosidaseP16278GLB1Lactase-phlorizin hydrolaseP09848LCTLactosylceramide alpha-2,3-sialyltransferaseQ9UNP4ST3GAL5