1.0 2011-09-21 00:05:24 UTC 2015-10-09 22:29:27 UTC FDB021930 Uridine diphosphate-N-acetylglucosamine Uridine 5'-diphosphate-GlcNAc (UDP-Glc-NAc )respond to nutrient excess to activate O-GlcNAcylation (addition of O-linked N-acetylglucosamine) in the hexosamine signaling pathway (HSP). O-GlcNAc addition (and removal) is key to histone remodeling, transcription, proliferation, apoptosis, and proteasomal degradation. This nutrient-responsive signaling pathway also modulates important cellular pathways, including the insulin signaling cascade in. Alterations in O-GlcNAc metabolism are associated with various human diseases including diabetes mellitus and neurodegeneration. (PMID: 16317114) The incidence of type 2 diabetes (non-insulin-dependent diabetes mellitus) has increased to epidemic proportions, being described as a disease of 'chronic overnutrition'. Due to the chemical makeup of UDP-GlcNAc,it is well positioned to serve as a glucose sensor in that it is a high-energy compound that requires and/or responds to glucose, amino acid, fatty acid and nucleotide metabolism for synthesis. UDP-Glc-NAc is the donor substrate for modification of nucleocytoplasmic proteins at serine and threonine residues with N-acetylglucosamine. Elevated levels of O-GlcNAc have an effect on insulin-stimulated glucose uptake. (PMID: 12678487) [HMDB] (2R,3R,4R,5S,6R)-3-(acetylamino)-4,5-Dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl [(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl dihydrogen diate (non-preferred name) (2R,3R,4R,5S,6R)-3-(acetylamino)-4,5-Dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl [(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl dihydrogen diic acid (non-preferred name) [[3-acetylamino-4,5-Dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxy-oryl]oxy-[[5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy]inate [[3-acetylamino-4,5-Dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxy-oryl]oxy-[[5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy]inic acid [[3-acetylamino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxy-phosphoryl]oxy-[[5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy]phosphinate [[3-acetylamino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxy-phosphoryl]oxy-[[5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy]phosphinic acid N-[2-[[[5-[(2,4-dioxo-1H-Pyrimidin-1-yl)]-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-inoyl]oxy-hydroxy-inoyl]oxy-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-3-yl]acetamide N-[2-[[[5-[(2,4-dioxo-1H-pyrimidin-1-yl)]-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphinoyl]oxy-hydroxy-phosphinoyl]oxy-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-3-yl]acetamide UDP-a-D-N-acetylglucosamine UDP-acetyl-D-glucosamine UDP-acetyl-delta-glucosamine UDP-acetylglucosamine UDP-alpha-D-N-acetylglucosamine UDP-alpha-delta-N-acetylglucosamine UDP-GlcNAc UDP-N-acetyl-D-glucosamine UDP-N-acetyl-delta-glucosamine UDP-N-acetyl-glucosamine UDP-N-acetylglucosamine UPPAG Uridine 5'-dio-N-acetlyglucosamine Uridine 5'-dio-N-acetylglucosamine Uridine 5'-Diphospho-N-Acetlyglucosamine Uridine 5'-diphospho-N-acetylglucosamine Uridine diate N-acetyl-D-glucosamine Uridine diate N-acetyl-delta-glucosamine Uridine diate N-acetylglucosamine Uridine dio-2-acetamido-2-deoxy-D-glucose Uridine dio-2-acetamido-2-deoxy-delta-glucose Uridine dio-N-acetyl-D-glucosamine Uridine dio-N-acetyl-delta-glucosamine Uridine dio-N-acetylglucosamine Uridine dioacetylglucosamine Uridine diphosphate N-acetyl-D-glucosamine Uridine diphosphate N-acetyl-delta-glucosamine Uridine diphosphate N-acetylglucosamine Uridine diphospho-2-acetamido-2-deoxy-D-glucose Uridine diphospho-2-acetamido-2-deoxy-delta-glucose Uridine diphospho-N-acetyl-D-glucosamine Uridine diphospho-N-acetyl-delta-glucosamine Uridine diphospho-N-acetylglucosamine uridine diphosphoacetylglucosamine Uridine pyroate 2-acetamido-2-deoxy-a-D-glucopyranosyl ester Uridine pyroate 2-acetamido-2-deoxy-alpha-D-glucopyranosyl ester Uridine pyroate 2-acetamido-2-deoxy-alpha-delta-glucopyranosyl ester Uridine pyrooacetylglucosamine Uridine pyrophosphate 2-acetamido-2-deoxy-a-D-glucopyranosyl ester Uridine pyrophosphate 2-acetamido-2-deoxy-alpha-D-glucopyranosyl ester Uridine pyrophosphate 2-acetamido-2-deoxy-alpha-delta-glucopyranosyl ester Uridine pyrophosphoacetylglucosamine URIDINE-diATE-N-acetylglucosamine URIDINE-diic acid-N-acetylglucosamine C17H27N3O17P2 607.3537 607.081569477 [({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid udp-N-acetyl-α-D-glucosamine 528-04-1 CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)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)/t7-,8-,10-,11-,12-,13-,14-,15-,16-/m1/s1 LFTYTUAZOPRMMI-CFRASDGPSA-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 UDP-amino sugar Solid logp -1.41 ALOGPS logs -1.72 ALOGPS solubility 1.14e+01 g/l ALOGPS logp -5.3 ChemAxon pka_strongest_acidic 1.74 ChemAxon pka_strongest_basic -3.5 ChemAxon iupac [({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3R,4R,5S,6R)-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)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)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)/t7-,8-,10-,11-,12-,13-,14-,15-,16-/m1/s1 ChemAxon inchikey LFTYTUAZOPRMMI-CFRASDGPSA-N ChemAxon polar_surface_area 300.41 ChemAxon refractivity 117.56 ChemAxon polarizability 50.39 ChemAxon rotatable_bond_count 10 ChemAxon acceptor_count 14 ChemAxon donor_count 9 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Amino Sugar Metabolism SMP00045 map00520 Specdb::NmrTwoD 1013 Specdb::NmrTwoD 1257 Specdb::NmrOneD 1314 Specdb::NmrOneD 143330 Specdb::NmrOneD 143331 Specdb::NmrOneD 143332 Specdb::NmrOneD 143333 Specdb::NmrOneD 143334 Specdb::NmrOneD 143335 Specdb::NmrOneD 143336 Specdb::NmrOneD 143337 Specdb::NmrOneD 143338 Specdb::NmrOneD 143339 Specdb::NmrOneD 143340 Specdb::NmrOneD 143341 Specdb::NmrOneD 143342 Specdb::NmrOneD 143343 Specdb::NmrOneD 143344 Specdb::NmrOneD 143345 Specdb::NmrOneD 143346 Specdb::NmrOneD 143347 Specdb::NmrOneD 143348 Specdb::NmrOneD 143349 Specdb::CMs 864 Specdb::CMs 18397 Specdb::CMs 30938 Specdb::CMs 37405 Specdb::CMs 480484 Specdb::CMs 480485 Specdb::CMs 480486 Specdb::CMs 480487 Specdb::CMs 480488 Specdb::CMs 480489 Specdb::CMs 480490 Specdb::CMs 480491 Specdb::CMs 480492 Specdb::CMs 480493 Specdb::CMs 480494 Specdb::CMs 480495 Specdb::CMs 480496 Specdb::CMs 480497 Specdb::CMs 480498 Specdb::CMs 480499 Specdb::CMs 480500 Specdb::CMs 480501 Specdb::CMs 480502 Specdb::CMs 480503 Specdb::CMs 480504 Specdb::MsMs 6243 Specdb::MsMs 6244 Specdb::MsMs 178665 Specdb::MsMs 178666 Specdb::MsMs 178667 Specdb::MsMs 180984 Specdb::MsMs 180985 Specdb::MsMs 180986 Specdb::MsMs 439118 Specdb::MsMs 439119 Specdb::MsMs 2244737 Specdb::MsMs 2245358 Specdb::MsMs 2246880 Specdb::MsMs 2247428 Specdb::MsMs 2248852 Specdb::MsMs 2249518 Specdb::MsMs 2250855 Specdb::MsMs 2251569 Specdb::MsMs 2429329 Specdb::MsMs 2429330 Specdb::MsMs 2429331 Specdb::MsMs 2505533 Specdb::MsMs 2505534 Specdb::MsMs 2505535 HMDB00290 16264 UD1 #<Reference:0x000055ac405f6198> #<Reference:0x000055ac405f5fe0> #<Reference:0x000055ac405f5e28> #<Reference:0x000055ac405f5c70> #<Reference:0x000055ac405f5ab8> 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-1,3-mannosyl-glycoprotein 4-beta-N-acetylglucosaminyltransferase A Q9UM21 MGAT4A Alpha-1,3-mannosyl-glycoprotein 4-beta-N-acetylglucosaminyltransferase B Q9UQ53 MGAT4B Alpha-1,6-mannosyl-glycoprotein 2-beta-N-acetylglucosaminyltransferase Q10469 MGAT2 Alpha-1,6-mannosylglycoprotein 6-beta-N-acetylglucosaminyltransferase A Q09328 MGAT5 Beta-1,3-N-acetylglucosaminyltransferase bGnT-2 Q9NY97 bGnT-2 Beta-1,4-mannosyl-glycoprotein 4-beta-N-acetylglucosaminyltransferase Q09327 MGAT3 Bifunctional UDP-N-acetylglucosamine 2-epimerase/N-acetylmannosamine kinase Q9Y223 GNE Exostosin-1 Q16394 EXT1 Exostosin-2 Q93063 EXT2 Exostosin-like 1 Q92935 EXTL1 Exostosin-like 2 Q9UBQ6 EXTL2 Exostosin-like 3 O43909 EXTL3 Lactosylceramide 1,3-N-acetyl-beta-D-glucosaminyltransferase Q9BYG0 B3GNT5 N-acetylglucosamine-1-phosphotransferase subunits alpha/beta Q3T906 GNPTAB N-acetyllactosaminide beta-1,3-N-acetylglucosaminyltransferase O43505 B3GNT1 N-acetyllactosaminide beta-1,6-N-acetylglucosaminyl-transferase, isoform B Q06430 GCNT2 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 UDP-N-acetylglucosamine transferase subunit ALG13 homolog Q9NP73 ALG13 UDP-N-acetylglucosamine transporter Q9Y2D2 SLC35A3 UDP-N-acetylglucosamine--dolichyl-phosphate N-acetylglucosaminephosphotransferase Q9H3H5 DPAGT1 UDP-N-acetylglucosamine--peptide N-acetylglucosaminyltransferase 110 kDa subunit O15294 OGT UDP-N-acetylhexosamine pyrophosphorylase Q16222 UAP1