1.0 2011-09-21 00:10:55 UTC 2020-04-21 18:02:10 UTC FDB022253 beta-N-Acetylglucosamine All animals and plants dynamically attach and remove beta-N-acetylglucosamine at serine and threonine residues on myriad nuclear and cytoplasmic proteins. b-N-Acetylglucosamine cycling, which is tightly regulated by the concerted actions of two highly conserved enzymes, serves as a nutrient and stress sensor. On some proteins, b-N-Acetylglucosamine competes directly with phosphate for serine/threonine residues. b-N-Acetylglucosamine's subcellular localization in hepatocytes established that it is highly concentrated at the nuclear envelope, particularly at the nuclear pore complex, but is also abundant and widespread within chromatin. However, several cytosolic and cytoskeletal proteins are also found to be glycosylated with b-N-Acetylglucosamine. b-N-Acetylglucosamination is in many ways distinct from 'classical' protein glycosylation. First, it is found mostly within the cytoplasm or nucleoplasm. Second, unlike the extraordinarily complex array of glycans found on extracellular glycoproteins, b-N-Acetylglucosamine is not elongated or further modified. Third, b-N-Acetylglucosamine cycles by means of mechanisms and on a timescale similar to those of phosphorylation and quite different from the cycling of complex extracellular glycans. b-N-Acetylglucosamination is one of the most common post-translational modifications. In terms of high-energy compounds, the intracellular concentration of the direct donor for b-N-Acetylglucosamination, UDP-GlcNAc, is second only to that of ATP, with 2-5% of all glucose being used to generate this sugar nucleotide. b-N-Acetylglucosaminated proteins can be found in almost every intracellular compartment, and there are proteins in almost every functional class that are subject to b-N-Acetylglucosamination. (PMID: 17460662) [HMDB] 2-Acetamido-2-deoxy-b-D-glucose 2-Acetamido-2-deoxy-beta-D-glucose 2-Acetamido-2-deoxy-beta-delta-glucose b-N-Acetyl-D-glucosamine b-N-Acetylglucosamine beta-N-Acetyl-D-glucosamine beta-N-Acetyl-delta-glucosamine beta-N-Acetylglucosamine BetaGlcNAc GlcNAc-b GlcNAc-beta GlcNAc-β N-Acetyl-b-D-glucosamine N-Acetyl-beta-D-glucosamine N-Acetyl-β-D-glucosamine C8H15NO6 221.2078 221.089937217 N-[(2R,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide N-acetyl-D-glucosamine 14131-68-1 CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O InChI=1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5-,6-,7-,8-/m1/s1 OVRNDRQMDRJTHS-FMDGEEDCSA-N belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group. Acylaminosugars Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic heteromonocyclic compounds Acetamides Carbonyl compounds Hemiacetals Hexoses Hydrocarbon derivatives N-acyl-alpha-hexosamines Organic oxides Organonitrogen compounds Organopnictogen compounds Oxacyclic compounds Oxanes Polyols Primary alcohols Secondary alcohols Secondary carboxylic acid amides Acetamide Acylaminosugar Alcohol Aliphatic heteromonocyclic compound Carbonyl group Carboxamide group Carboxylic acid derivative Hemiacetal Hexose monosaccharide Hydrocarbon derivative Monosaccharide N-acyl-alpha-hexosamine Organic nitrogen compound Organic oxide Organoheterocyclic compound Organonitrogen compound Organopnictogen compound Oxacycle Oxane Polyol Primary alcohol Secondary alcohol Secondary carboxylic acid amide N-acetyl-D-glucosamine Solid logp -2.60 ALOGPS logs 0.06 ALOGPS solubility 2.54e+02 g/l ALOGPS logp -3.2 ChemAxon pka_strongest_acidic 11.6 ChemAxon pka_strongest_basic -1.6 ChemAxon iupac N-[(2R,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide ChemAxon average_mass 221.2078 ChemAxon mono_mass 221.089937217 ChemAxon smiles CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O ChemAxon formula C8H15NO6 ChemAxon inchi InChI=1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5-,6-,7-,8-/m1/s1 ChemAxon inchikey OVRNDRQMDRJTHS-FMDGEEDCSA-N ChemAxon polar_surface_area 119.25 ChemAxon refractivity 47.02 ChemAxon polarizability 21.08 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 6 ChemAxon donor_count 5 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::NmrTwoD 1491 Specdb::MsMs 1144 Specdb::MsMs 1145 Specdb::MsMs 1146 Specdb::MsMs 295129 Specdb::MsMs 295130 Specdb::MsMs 295131 Specdb::MsMs 336061 Specdb::MsMs 336062 Specdb::MsMs 336063 Specdb::MsMs 2815966 Specdb::MsMs 2815967 Specdb::MsMs 2815968 Specdb::MsMs 2892368 Specdb::MsMs 2892369 Specdb::MsMs 2892370 Specdb::NmrOneD 1547 Specdb::NmrOneD 20842 Specdb::NmrOneD 20843 Specdb::NmrOneD 20844 Specdb::NmrOneD 20845 Specdb::NmrOneD 20846 Specdb::NmrOneD 20847 Specdb::NmrOneD 20848 Specdb::NmrOneD 20849 Specdb::NmrOneD 20850 Specdb::NmrOneD 20851 Specdb::NmrOneD 20852 Specdb::NmrOneD 20853 Specdb::NmrOneD 20854 Specdb::NmrOneD 20855 Specdb::NmrOneD 20856 Specdb::NmrOneD 20857 Specdb::NmrOneD 20858 Specdb::NmrOneD 20859 Specdb::NmrOneD 20860 Specdb::NmrOneD 20861 Specdb::CMs 13251 Specdb::CMs 37774 Specdb::CMs 130400 Specdb::CMs 138134 Specdb::CMs 1077296 Specdb::CMs 1077298 Specdb::CMs 1077300 Specdb::CMs 1077302 Specdb::CMs 1077303 Specdb::CMs 1077305 Specdb::CMs 1077307 Specdb::CMs 1077308 Specdb::CMs 1077310 Specdb::CMs 1077312 Specdb::CMs 1077314 Specdb::CMs 1077316 Specdb::CMs 1077318 Specdb::CMs 1077320 Specdb::CMs 1077322 Specdb::CMs 1077324 Specdb::CMs 1077326 Specdb::CMs 1077328 Specdb::CMs 1077329 Specdb::CMs 1077331 Specdb::CMs 1077333 HMDB00803 NAG #<Reference:0x000055ce315b5068> #<Reference:0x000055ce315b4eb0> #<Reference:0x000055ce315b4cf8> 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