1.0 2011-09-21 00:05:27 UTC 2015-07-21 06:56:53 UTC FDB021933 Uridine diphosphate-N-acetylgalactosamine Uridine diphosphate-N-acetylgalactosamine (UDP-GalNAc) is a sugar donor metabolite, transferring N-acetylgalactosamine (GalNAc, an O-glycan) from UDP-GalNAc to serine and threonine residues, forming an alpha anomeric linkage in a reaction catalyzed by enzymes known as UDP-N-acetylgalactosamine: polypeptide N-acetylgalactosaminyltransferases; addition of GalNAc to serine or threonine represents the first committed step in mucin biosynthesis. O-glycans impart unique structural features to mucin glycoproteins and numerous membrane receptors, and resistance to thermal change and proteolytic attack in a number of diverse proteins. O-linked carbohydrate side chains function as ligands for receptors; lymphocyte and leukocyte homing and as signals for protein sorting. (PMID: 12634319) Animal studies suggest that overactivity of the hexosamine pathway, resulting in increased UDP-hexosamines [i.e.: UDP-N-acetylgalactosamine (UDP-GalNAc)] is an important mechanism by which hyperglycemia causes insulin resistance. However, to date, human studies concerning the role of the hexosamine pathway in hyperglycemia-induced insulin resistance are scarce and restricted to measurements of glutamine fructose-6-phosphate amidotransferase (GFAT) enzyme activity. Both positive and negative correlations between GFAT activity in human muscle tissue from patients with type 2 DM and glucose disposal rate have been reported. (PMID: 12414889) [HMDB] UDP-N-acetyl-D-galactosamine UDP-N-acetyl-delta-galactosamine UDP-N-acetylgalactosamine Uridine 5'-dio-N-acetylgalactosamine Uridine 5'-diphospho-N-acetylgalactosamine Uridine diate-N-acetyl-D-galactosamine Uridine diate-N-acetyl-delta-galactosamine Uridine dio-2-acetamido-2-deoxy-D-galactose Uridine dio-2-acetamido-2-deoxy-delta-galactose Uridine dio-N-acetylgalactosamine Uridine dioacetylgalactosamine Uridine diphosphate-N-acetyl-D-galactosamine Uridine diphosphate-N-acetyl-delta-galactosamine Uridine diphospho-2-acetamido-2-deoxy-D-galactose Uridine diphospho-2-acetamido-2-deoxy-delta-galactose Uridine diphospho-N-acetylgalactosamine Uridine diphosphoacetylgalactosamine Uridine pyroate 2-acetamido-2-deoxy-a-D-galactopyranosyl ester Uridine pyroate 2-acetamido-2-deoxy-alpha-D-galactopyranosyl ester Uridine pyroate 2-acetamido-2-deoxy-alpha-delta-galactopyranosyl ester Uridine pyroate N-acetyl-a-D-chondrosamine ester Uridine pyroate N-acetyl-alpha-D-chondrosamine ester Uridine pyroate N-acetyl-alpha-delta-chondrosamine ester Uridine pyrooacetylgalactosamine Uridine pyrophosphate 2-acetamido-2-deoxy-a-D-galactopyranosyl ester Uridine pyrophosphate 2-acetamido-2-deoxy-alpha-D-galactopyranosyl ester Uridine pyrophosphate 2-acetamido-2-deoxy-alpha-delta-galactopyranosyl ester Uridine pyrophosphate N-acetyl-a-D-chondrosamine ester Uridine pyrophosphate N-acetyl-alpha-D-chondrosamine ester Uridine pyrophosphate N-acetyl-alpha-delta-chondrosamine ester Uridine pyrophosphoacetylgalactosamine C17H27N3O17P2 607.3537 607.081569477 [({[5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid {[5-(2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid 7277-98-7 CC(=O)NC1C(O)C(O)C(CO)OC1OP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1O)N1C=CC(=O)NC1=O InChI=1S/C17H27N3O17P2/c1-6(22)18-10-13(26)11(24)7(4-21)35-16(10)36-39(31,32)37-38(29,30)33-5-8-12(25)14(27)15(34-8)20-3-2-9(23)19-17(20)28/h2-3,7-8,10-16,21,24-27H,4-5H2,1H3,(H,18,22)(H,29,30)(H,31,32)(H,19,23,28) LFTYTUAZOPRMMI-UHFFFAOYSA-N belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. Pyrimidine nucleotide sugars Organic compounds Nucleosides, nucleotides, and analogues Pyrimidine nucleotides Pyrimidine nucleotide sugars Aromatic heteromonocyclic compounds Acetamides Azacyclic compounds Carbonyl compounds Glycosylamines Heteroaromatic compounds Hydrocarbon derivatives Hydropyrimidines Lactams Monoalkyl phosphates Monosaccharide phosphates N-acyl-alpha-hexosamines Organic oxides Organic pyrophosphates Organonitrogen compounds Organopnictogen compounds Oxacyclic compounds Oxanes Pentose phosphates Primary alcohols Pyrimidine ribonucleoside diphosphates Pyrimidones Secondary alcohols Secondary carboxylic acid amides Tetrahydrofurans Ureas Vinylogous amides Acetamide Alcohol Alkyl phosphate Aromatic heteromonocyclic compound Azacycle Carbonyl group Carboxamide group Carboxylic acid derivative Glycosyl compound Heteroaromatic compound Hydrocarbon derivative Hydropyrimidine Lactam Monoalkyl phosphate Monosaccharide Monosaccharide phosphate N-acyl-alpha-hexosamine N-glycosyl compound Organic nitrogen compound Organic oxide Organic oxygen compound Organic phosphoric acid derivative Organic pyrophosphate Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Oxacycle Oxane Pentose phosphate Pentose-5-phosphate Phosphoric acid ester Primary alcohol Pyrimidine Pyrimidine nucleotide sugar Pyrimidine ribonucleoside diphosphate Pyrimidone Secondary alcohol Secondary carboxylic acid amide Tetrahydrofuran Urea Vinylogous amide Solid logp -1.70 ALOGPS logs -1.67 ALOGPS solubility 1.30e+01 g/l ALOGPS logp -5.3 ChemAxon pka_strongest_acidic 1.74 ChemAxon pka_strongest_basic -3.5 ChemAxon iupac [({[5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid ChemAxon average_mass 607.3537 ChemAxon mono_mass 607.081569477 ChemAxon smiles CC(=O)NC1C(O)C(O)C(CO)OC1OP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1O)N1C=CC(=O)NC1=O ChemAxon formula C17H27N3O17P2 ChemAxon inchi InChI=1S/C17H27N3O17P2/c1-6(22)18-10-13(26)11(24)7(4-21)35-16(10)36-39(31,32)37-38(29,30)33-5-8-12(25)14(27)15(34-8)20-3-2-9(23)19-17(20)28/h2-3,7-8,10-16,21,24-27H,4-5H2,1H3,(H,18,22)(H,29,30)(H,31,32)(H,19,23,28) ChemAxon inchikey LFTYTUAZOPRMMI-UHFFFAOYSA-N ChemAxon polar_surface_area 300.41 ChemAxon refractivity 117.56 ChemAxon polarizability 51.59 ChemAxon rotatable_bond_count 10 ChemAxon acceptor_count 14 ChemAxon donor_count 9 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 21272 Specdb::CMs 37413 Specdb::MsMs 8759 Specdb::MsMs 8760 Specdb::MsMs 8761 Specdb::MsMs 15431 Specdb::MsMs 15432 Specdb::MsMs 15433 Specdb::MsMs 440097 Specdb::MsMs 451926 Specdb::MsMs 2236102 Specdb::MsMs 2238270 Specdb::MsMs 2239329 Specdb::MsMs 2723076 Specdb::MsMs 2723077 Specdb::MsMs 2723078 Specdb::MsMs 2955513 Specdb::MsMs 2955514 Specdb::MsMs 2955515 Specdb::NmrOneD 143450 Specdb::NmrOneD 143451 Specdb::NmrOneD 143452 Specdb::NmrOneD 143453 Specdb::NmrOneD 143454 Specdb::NmrOneD 143455 Specdb::NmrOneD 143456 Specdb::NmrOneD 143457 Specdb::NmrOneD 143458 Specdb::NmrOneD 143459 Specdb::NmrOneD 143460 Specdb::NmrOneD 143461 Specdb::NmrOneD 143462 Specdb::NmrOneD 143463 Specdb::NmrOneD 143464 Specdb::NmrOneD 143465 Specdb::NmrOneD 143466 Specdb::NmrOneD 143467 Specdb::NmrOneD 143468 Specdb::NmrOneD 143469 HMDB00304 #<Reference:0x000055ce31682ae0> #<Reference:0x000055ce31682860> #<Reference:0x000055ce316826a8> 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-1,4 N-acetylgalactosaminyltransferase 1 Q00973 B4GALNT1 Beta-1,4-N-acetylgalactosaminyltransferase 3 Q6L9W6 B4GALNT3 Chondroitin sulfate N-acetylgalactosaminyltransferase 1 Q8TDX6 CSGALNACT1 Chondroitin sulfate N-acetylgalactosaminyltransferase 2 Q8N6G5 CSGALNACT2 N-acetyl-beta-glucosaminyl-glycoprotein 4-beta-N-acetylgalactosaminyltransferase 1 Q76KP1 B4GALNT4 Polypeptide N-acetylgalactosaminyltransferase 13 Q68VI8 GALNT13 Pp-GalNAc-transferase 20 Q2L4S5 GALNT20 UDP-N-acetylglucosamine--peptide N-acetylglucosaminyltransferase 110 kDa subunit O15294 OGT