1.0 2011-09-21 00:30:42 UTC 2015-07-21 06:57:44 UTC FDB023495 Ganglioside GA1 (d18:1/20:0) 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] C64H118N2O23 1283.6213 1282.812538092 N-[(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]icosanimidic acid N-[(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]icosanimidic 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)CCCCCCCCCCCCCCCCCCC)[C@]([H])(O)C=CCCCCCCCCCCCCC InChI=1S/C64H118N2O23/c1-4-6-8-10-12-14-16-18-19-20-21-23-25-27-29-31-33-35-48(73)66-42(43(72)34-32-30-28-26-24-22-17-15-13-11-9-7-5-2)40-82-62-56(80)53(77)59(46(38-69)85-62)88-64-57(81)54(78)58(47(39-70)86-64)87-61-49(65-41(3)71)60(51(75)45(37-68)83-61)89-63-55(79)52(76)50(74)44(36-67)84-63/h32,34,42-47,49-64,67-70,72,74-81H,4-31,33,35-40H2,1-3H3,(H,65,71)(H,66,73)/t42-,43+,44+,45+,46+,47+,49+,50-,51-,52-,53+,54+,55+,56?,57+,58-,59+,60+,61-,62+,63-,64-/m0/s1 PARSTZCBJLHNFB-MUFXJHLXSA-N belongs to the class of organic compounds known as 1,2-diacylglycerols. These are diacylglycerols containing a glycerol acylated at positions 1 and 2. 1,2-diacylglycerols Organic compounds Lipids and lipid-like molecules Glycerolipids Diradylglycerols Aliphatic acyclic compounds Carbonyl compounds Carboxylic acid esters Dicarboxylic acids and derivatives Fatty acid esters Hydrocarbon derivatives Organic oxides Primary alcohols 1,2-acyl-sn-glycerol Alcohol Aliphatic acyclic compound Carbonyl group Carboxylic acid derivative Carboxylic acid ester Dicarboxylic acid or derivatives Fatty acid ester Fatty acyl Hydrocarbon derivative Organic oxide Organic oxygen compound Organooxygen compound Primary alcohol Solid logp 4.54 ALOGPS logs -4.65 ALOGPS solubility 2.88e-02 g/l ALOGPS logp 6.91 ChemAxon pka_strongest_acidic 5.34 ChemAxon pka_strongest_basic 2.6 ChemAxon iupac N-[(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]icosanimidic acid ChemAxon average_mass 1283.6213 ChemAxon mono_mass 1282.812538092 ChemAxon smiles [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)CCCCCCCCCCCCCCCCCCC)[C@]([H])(O)C=CCCCCCCCCCCCCC ChemAxon formula C64H118N2O23 ChemAxon inchi InChI=1S/C64H118N2O23/c1-4-6-8-10-12-14-16-18-19-20-21-23-25-27-29-31-33-35-48(73)66-42(43(72)34-32-30-28-26-24-22-17-15-13-11-9-7-5-2)40-82-62-56(80)53(77)59(46(38-69)85-62)88-64-57(81)54(78)58(47(39-70)86-64)87-61-49(65-41(3)71)60(51(75)45(37-68)83-61)89-63-55(79)52(76)50(74)44(36-67)84-63/h32,34,42-47,49-64,67-70,72,74-81H,4-31,33,35-40H2,1-3H3,(H,65,71)(H,66,73)/t42-,43+,44+,45+,46+,47+,49+,50-,51-,52-,53+,54+,55+,56?,57+,58-,59+,60+,61-,62+,63-,64-/m0/s1 ChemAxon inchikey PARSTZCBJLHNFB-MUFXJHLXSA-N ChemAxon polar_surface_area 402.01 ChemAxon refractivity 325.98 ChemAxon polarizability 146.47 ChemAxon rotatable_bond_count 47 ChemAxon acceptor_count 25 ChemAxon donor_count 15 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon HMDB04904 #<Reference:0x000055ce324c6480> #<Reference:0x000055ce324c62a0> #<Reference:0x000055ce324c60e8> #<Reference:0x000055ce324c5ee0> #<Reference:0x000055ce324c5d00> #<Reference:0x000055ce324c5af8> #<Reference:0x000055ce324c5940> #<Reference:0x000055ce324c5760> #<Reference:0x000055ce324c5558> #<Reference:0x000055ce324c53a0> #<Reference:0x000055ce324c51c0> #<Reference:0x000055ce324c4fb8> #<Reference:0x000055ce324c4e00> #<Reference:0x000055ce324c4c20> #<Reference:0x000055ce324c4a18> #<Reference:0x000055ce324c4860> #<Reference:0x000055ce324c4680> #<Reference:0x000055ce324c4478> #<Reference:0x000055ce324c42c0> 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 Beta-galactosidase P16278 GLB1 Lactase-phlorizin hydrolase P09848 LCT Lactosylceramide alpha-2,3-sialyltransferase Q9UNP4 ST3GAL5