1.0 2011-09-21 00:36:32 UTC 2024-11-29 22:25:05 UTC FDB023896 alpha-N-Phenylacetyl-L-glutamine Phenylacetylglutamine is a product formed by the conjugation of phenylacetate and glutamine. Technically it is the amino acid acetylation product of phenylacetate (or phenylbutyrate after beta-oxidation). Phenylacetylglutamine is a normal constituent of human urine, but other mammals including the dog, cat, rat, monkey, sheep and horse do not excrete this compound. Phenylacetyl CoA and glutamine react to form phenylacetyl glutamine and Coenzyme A. The enzyme (Glutamine N-acetyl transferase) that catalyzes this reaction has been purified from human liver mitochondria and shown to be a distinct polypeptide species from glycine-N-acyltransferase. Phenylacetylglutamine is a major nitrogenous metabolite that accumulates in uremia. (PMID: 2791363; PMID: 8972626). It has been shown that over 50% of urine phenylacetylglutamine may be derived from kidney conjugation of free plasma phenylacetic acid and/or from the kidney's preferential filtration of conjugated phenylacetic acid (PMID: 6420430) In enzymology, a glutamine N-phenylacetyltransferase (EC 2.3.1.14) is an enzyme that catalyzes the chemical reaction phenylacetyl-CoA + L-glutamine CoA + alpha-N-phenylacetyl-L-glutamine Thus, the two substrates of this enzyme are phenylacetyl-CoA and L-glutamine, whereas its two products are CoA and alpha-N-phenylacetyl-L-glutamine. [HMDB] a-N-Phenylacetyl-L-glutamine alpha-N-Phenylacetyl-L-glutamine L-N(sup2)-(Phenylacetyl)glutamine N(2)-(Phenylacetyl)-L-glutamine Phenylacetyl-L-glutamine Phenylacetylglutamine α-N-phenylacetyl-L-glutamine C13H16N2O4 264.2771 264.11100701 (2S)-4-carbamoyl-2-(2-phenylacetamido)butanoic acid phenylacetylglutamine 28047-15-6 NC(=O)CC[C@H](NC(=O)CC1=CC=CC=C1)C(O)=O InChI=1S/C13H16N2O4/c14-11(16)7-6-10(13(18)19)15-12(17)8-9-4-2-1-3-5-9/h1-5,10H,6-8H2,(H2,14,16)(H,15,17)(H,18,19)/t10-/m0/s1 JFLIEFSWGNOPJJ-JTQLQIEISA-N belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. N-acyl-alpha amino acids Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aromatic homomonocyclic compounds Benzene and substituted derivatives Carbonyl compounds Carboximidic acids Carboxylic acids Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Organonitrogen compounds Organopnictogen compounds Propargyl-type 1,3-dipolar organic compounds Aromatic homomonocyclic compound Benzenoid Carbonyl group Carboximidic acid Carboximidic acid derivative Carboxylic acid Hydrocarbon derivative Monocarboxylic acid or derivatives Monocyclic benzene moiety N-acyl-alpha-amino acid Organic 1,3-dipolar compound Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Propargyl-type 1,3-dipolar organic compound N(2)-phenylacetylglutamine Solid logp -0.35 ALOGPS logs -2.83 ALOGPS solubility 3.88e-01 g/l ALOGPS logp -0.086 ChemAxon pka_strongest_acidic 3.9 ChemAxon pka_strongest_basic -1.5 ChemAxon iupac (2S)-4-carbamoyl-2-(2-phenylacetamido)butanoic acid ChemAxon average_mass 264.2771 ChemAxon mono_mass 264.11100701 ChemAxon smiles NC(=O)CC[C@H](NC(=O)CC1=CC=CC=C1)C(O)=O ChemAxon formula C13H16N2O4 ChemAxon inchi InChI=1S/C13H16N2O4/c14-11(16)7-6-10(13(18)19)15-12(17)8-9-4-2-1-3-5-9/h1-5,10H,6-8H2,(H2,14,16)(H,15,17)(H,18,19)/t10-/m0/s1 ChemAxon inchikey JFLIEFSWGNOPJJ-JTQLQIEISA-N ChemAxon polar_surface_area 109.49 ChemAxon refractivity 67.28 ChemAxon polarizability 26.55 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Phenylacetate Metabolism SMP00126 map00360 Metabolism and Physiological Effects of Phenylacetylglutamine SMP0123208 Specdb::CMs 10064 Specdb::CMs 39005 Specdb::CMs 160456 Specdb::NmrOneD 68172 Specdb::NmrOneD 68173 Specdb::NmrOneD 68174 Specdb::NmrOneD 68175 Specdb::NmrOneD 68176 Specdb::NmrOneD 68177 Specdb::NmrOneD 68178 Specdb::NmrOneD 68179 Specdb::NmrOneD 68180 Specdb::NmrOneD 68181 Specdb::NmrOneD 68182 Specdb::NmrOneD 68183 Specdb::NmrOneD 68184 Specdb::NmrOneD 68185 Specdb::NmrOneD 68186 Specdb::NmrOneD 68187 Specdb::NmrOneD 68188 Specdb::NmrOneD 68189 Specdb::NmrOneD 68190 Specdb::NmrOneD 68191 Specdb::MsMs 94506 Specdb::MsMs 94507 Specdb::MsMs 94508 Specdb::MsMs 158538 Specdb::MsMs 158539 Specdb::MsMs 158540 Specdb::MsMs 439962 Specdb::MsMs 450249 Specdb::MsMs 450250 Specdb::MsMs 2236048 Specdb::MsMs 2237326 Specdb::MsMs 2238201 Specdb::MsMs 2239385 Specdb::MsMs 2240325 Specdb::MsMs 2241373 Specdb::MsMs 2242375 Specdb::MsMs 2243491 Specdb::MsMs 2246564 Specdb::MsMs 2247715 Specdb::MsMs 2253132 Specdb::MsMs 2253345 Specdb::MsMs 2255198 Specdb::MsMs 2255353 Specdb::MsMs 2257283 Specdb::MsMs 2257315 HMDB06344 #<Reference:0x000055ce309e3500> #<Reference:0x000055ce309e32d0> #<Reference:0x000055ce309e3078> 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