1.0 2011-09-21 00:35:01 UTC 2015-10-09 22:33:39 UTC FDB023808 N-Acetylglutamine N-Acetylglutamine (GIcNAc) is a modified amino acid (an acetylated analogue of glutamine), a metabolite present in normal human urine. The decomposition products of GIcNAc have been identified by NMR and HPLC-MS as N-acetyl-L-glutamic acid, N-(2,6-dioxo-3-piperidinyl) acetamide, pyroglutamic acid, glutamic acid, and glutamine. GIcNAc is used for parenteral nutrition as a source of glutamine, since glutamine is too unstable, but GIcNAc is very stable. In patients treated with aminoglycosides and/or glycopeptides, elevation GIcNAc in urine suggests renal tubular injury. High amounts of N-acetylated amino acids (i.e.: N-Acetylglutamine) were detected patient with aminoacylase I deficiency (EC 3.5.1.14, a homodimeric zinc-binding metalloenzyme located in the cytosol), a novel inborn error of metabolism. (PMID: 15331932, 11312773, 7952062, 2569664, 16274666) [HMDB] Aceglutamid Aceglutamide Acetylglutamine alpha-n-acetyl-l-glutamine L-2-Acetamidoglutaramic acid L-N2-acetyl-Glutamine N-acetyl-l-glutamine N2-Acetyl-L-glutamine N2-acetylglutamine C7H12N2O4 188.1812 188.079706882 4-carbamoyl-2-acetamidobutanoic acid N-acetyl-L-glutamine 2490-97-3 CC(=O)NC(CCC(N)=O)C(O)=O InChI=1S/C7H12N2O4/c1-4(10)9-5(7(12)13)2-3-6(8)11/h5H,2-3H2,1H3,(H2,8,11)(H,9,10)(H,12,13) KSMRODHGGIIXDV-UHFFFAOYSA-N belongs to the class of organic compounds known as glutamine and derivatives. Glutamine and derivatives are compounds containing glutamine or a derivative thereof resulting from reaction of glutamine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Glutamine and derivatives Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aliphatic acyclic compounds Acetamides Carbonyl compounds Carboxylic acids Fatty acids and conjugates Fatty amides Hydrocarbon derivatives Monocarboxylic acids and derivatives N-acyl-alpha amino acids Organic oxides Organonitrogen compounds Organopnictogen compounds Primary carboxylic acid amides Secondary carboxylic acid amides Acetamide Aliphatic acyclic compound Carbonyl group Carboxamide group Carboxylic acid Fatty acid Fatty acyl Fatty amide Glutamine or derivatives Hydrocarbon derivative Monocarboxylic acid or derivatives N-acyl-alpha amino acid or derivatives N-acyl-alpha-amino acid Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary carboxylic acid amide Secondary carboxylic acid amide N(2)-acylglutamine N-acetyl-amino acid Solid logp -2.17 ALOGPS logs -0.93 ALOGPS solubility 2.19e+01 g/l ALOGPS logp -1.9 ChemAxon pka_strongest_acidic 3.76 ChemAxon pka_strongest_basic -1.4 ChemAxon iupac 4-carbamoyl-2-acetamidobutanoic acid ChemAxon average_mass 188.1812 ChemAxon mono_mass 188.079706882 ChemAxon smiles CC(=O)NC(CCC(N)=O)C(O)=O ChemAxon formula C7H12N2O4 ChemAxon inchi InChI=1S/C7H12N2O4/c1-4(10)9-5(7(12)13)2-3-6(8)11/h5H,2-3H2,1H3,(H2,8,11)(H,9,10)(H,12,13) ChemAxon inchikey KSMRODHGGIIXDV-UHFFFAOYSA-N ChemAxon polar_surface_area 109.49 ChemAxon refractivity 42.55 ChemAxon polarizability 17.66 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 102111 Specdb::MsMs 102112 Specdb::MsMs 102113 Specdb::MsMs 167850 Specdb::MsMs 167851 Specdb::MsMs 167852 Specdb::NmrOneD 4467 Specdb::NmrOneD 4593 Specdb::CMs 3379 Specdb::CMs 38940 HMDB06029 #<Reference:0x000055ce326f83c0> #<Reference:0x000055ce326f8050> #<Reference:0x000055ce326f7bc8> #<Reference:0x000055ce326f7a10> #<Reference:0x000055ce326f7858> 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