1.0 2011-09-21 00:30:49 UTC 2015-07-21 06:57:44 UTC FDB023506 Ganglioside GD3 (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 GD3 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] C72H129N3O29 1500.7974 1499.871175181 (2S,4S,5R)-2-{[(1S,2R)-1-[(3R,4S,6S)-6-carboxy-6-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,6R)-4,5-dihydroxy-6-{[(2S,3R)-3-hydroxy-2-[(1-hydroxyicosylidene)amino]octadec-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]-1,3-dihydroxypropan-2-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid (2S,4S,5R)-2-{[(1S,2R)-1-[(3R,4S,6S)-6-carboxy-6-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,6R)-4,5-dihydroxy-6-{[(2S,3R)-3-hydroxy-2-[(1-hydroxyicosylidene)amino]octadec-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]-1,3-dihydroxypropan-2-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid [H][C@@](O)(CO)[C@@]([H])(O)C1O[C@@](C[C@]([H])(O)[C@@]1([H])NC(C)=O)(O[C@]([H])(CO)[C@@]([H])(O)C1O[C@@](C[C@]([H])(O)[C@@]1([H])NC(C)=O)(O[C@@]1([H])[C@@]([H])(O)[C@@]([H])(CO)O[C@@]([H])(O[C@@]2([H])[C@]([H])(O)C(O)[C@]([H])(OC[C@]([H])(NC(=O)CCCCCCCCCCCCCCCCCCC)[C@]([H])(O)C=CCCCCCCCCCCCCC)O[C@]2([H])CO)[C@]1([H])O)C(O)=O)C(O)=O InChI=1S/C72H129N3O29/c1-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-36-54(86)75-46(47(82)35-33-31-29-27-25-23-18-16-14-12-10-8-6-2)43-97-67-61(91)60(90)63(53(42-79)99-67)100-68-62(92)66(58(88)51(40-77)98-68)104-72(70(95)96)38-49(84)56(74-45(4)81)65(103-72)59(89)52(41-78)101-71(69(93)94)37-48(83)55(73-44(3)80)64(102-71)57(87)50(85)39-76/h33,35,46-53,55-68,76-79,82-85,87-92H,5-32,34,36-43H2,1-4H3,(H,73,80)(H,74,81)(H,75,86)(H,93,94)(H,95,96)/t46-,47+,48-,49-,50+,51+,52+,53+,55+,56+,57+,58-,59+,60+,61?,62+,63+,64?,65?,66-,67+,68-,71+,72-/m0/s1 YAUKCYAJCXBWAS-YPZXMGNHSA-N belongs to the class of organic compounds known as nicotinamides. These are heterocyclic aromatic compounds containing a pyridine ring substituted at position 3 by a carboxamide group. Nicotinamides Organic compounds Organoheterocyclic compounds Pyridines and derivatives Pyridinecarboxylic acids and derivatives Aromatic heteromonocyclic compounds Azacyclic compounds Cyclic ketones Dihydropyridines Heteroaromatic compounds Hydrocarbon derivatives Organic oxides Organonitrogen compounds Organopnictogen compounds Primary carboxylic acid amides Vinylogous amides Aromatic heteromonocyclic compound Azacycle Carboxamide group Carboxylic acid derivative Cyclic ketone Dihydropyridine Heteroaromatic compound Hydrocarbon derivative Hydropyridine Nicotinamide Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary carboxylic acid amide Vinylogous amide methylpyridines pyridinecarboxamide pyridone Solid logp 3.01 ALOGPS logs -4.73 ALOGPS solubility 2.82e-02 g/l ALOGPS logp 5.91 ChemAxon pka_strongest_acidic 2.7 ChemAxon pka_strongest_basic 2.2 ChemAxon iupac (2S,4S,5R)-2-{[(1S,2R)-1-[(3R,4S,6S)-6-carboxy-6-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,6R)-4,5-dihydroxy-6-{[(2S,3R)-3-hydroxy-2-[(1-hydroxyicosylidene)amino]octadec-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]-1,3-dihydroxypropan-2-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid ChemAxon average_mass 1500.7974 ChemAxon mono_mass 1499.871175181 ChemAxon smiles [H][C@@](O)(CO)[C@@]([H])(O)C1O[C@@](C[C@]([H])(O)[C@@]1([H])NC(C)=O)(O[C@]([H])(CO)[C@@]([H])(O)C1O[C@@](C[C@]([H])(O)[C@@]1([H])NC(C)=O)(O[C@@]1([H])[C@@]([H])(O)[C@@]([H])(CO)O[C@@]([H])(O[C@@]2([H])[C@]([H])(O)C(O)[C@]([H])(OC[C@]([H])(NC(=O)CCCCCCCCCCCCCCCCCCC)[C@]([H])(O)C=CCCCCCCCCCCCCC)O[C@]2([H])CO)[C@]1([H])O)C(O)=O)C(O)=O ChemAxon formula C72H129N3O29 ChemAxon inchi InChI=1S/C72H129N3O29/c1-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-36-54(86)75-46(47(82)35-33-31-29-27-25-23-18-16-14-12-10-8-6-2)43-97-67-61(91)60(90)63(53(42-79)99-67)100-68-62(92)66(58(88)51(40-77)98-68)104-72(70(95)96)38-49(84)56(74-45(4)81)65(103-72)59(89)52(41-78)101-71(69(93)94)37-48(83)55(73-44(3)80)64(102-71)57(87)50(85)39-76/h33,35,46-53,55-68,76-79,82-85,87-92H,5-32,34,36-43H2,1-4H3,(H,73,80)(H,74,81)(H,75,86)(H,93,94)(H,95,96)/t46-,47+,48-,49-,50+,51+,52+,53+,55+,56+,57+,58-,59+,60+,61?,62+,63+,64?,65?,66-,67+,68-,71+,72-/m0/s1 ChemAxon inchikey YAUKCYAJCXBWAS-YPZXMGNHSA-N ChemAxon polar_surface_area 529.43 ChemAxon refractivity 371.11 ChemAxon polarizability 167.31 ChemAxon rotatable_bond_count 54 ChemAxon acceptor_count 32 ChemAxon donor_count 19 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon HMDB04915 #<Reference:0x00007f093c196e68> #<Reference:0x00007f093c196cb0> #<Reference:0x00007f093c196aa8> #<Reference:0x00007f093c1968a0> #<Reference:0x00007f093c1966e8> #<Reference:0x00007f093c1964e0> #<Reference:0x00007f093c1962d8> 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 Alpha-N-acetylneuraminide alpha-2,8-sialyltransferase Q92185 ST8SIA1 Antigen-presenting glycoprotein CD1d P15813 CD1D Beta-1,3-galactosyltransferase 5 Q9Y2C3 B3GALT5 Beta-1,4 N-acetylgalactosaminyltransferase 1 Q00973 B4GALNT1 Epididymal secretory protein E1 P61916 NPC2 Ganglioside GM2 activator P17900 GM2A 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 Lactosylceramide 1,3-N-acetyl-beta-D-glucosaminyltransferase Q9BYG0 B3GNT5 N-acetylglucosaminyl-phosphatidylinositol de-N-acetylase Q9Y2B2 PIGL Non-lysosomal glucosylceramidase Q9HCG7 GBA2 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 T-cell surface glycoprotein CD1e, membrane-associated P15812 CD1E