1.0 2016-09-30 23:21:41 UTC 2020-05-21 16:28:34 UTC BMDB0006344 BMDB06344 Alpha-N-Phenylacetyl-L-glutamine Phenylacetylglutamine 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. Phenylacetylglutamine is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Phenylacetylglutamine can be biosynthesized from L-glutamine through the action of the enzyme glycine N-acyltransferase. In cattle, phenylacetylglutamine is involved in the metabolic pathway called the phenylacetate metabolism pathway. alpha-N-Phenylacetyl-L-glutamine Phenylacetyl-L-glutamine N2-(2-Phenylacetyl)-L-glutamine a-N-Phenylacetyl-L-glutamine Α-N-phenylacetyl-L-glutamine Phenylacetylglutamine N(2)-(Phenylacetyl)-L-glutamine N(2)-(2-Phenylacetyl)-L-glutamine N-Phenylacetylglutamine N2-(Phenylacetyl)-L-glutamine α-N-Phenylacetylglutamine alpha-N-Phenylacetylglutamine 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. Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues N-acyl-alpha amino acids 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 Aromatic homomonocyclic compounds N(2)-phenylacetylglutamine Solid logp -0.35 ALOGPS logs -2.83 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 number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Phenylacetate Metabolism SMP0087208 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 Liver Metabolomics analysis was performed using GC-MS/LC-MS in multiparous Holstein dairy cows Shahzad K, Lopreiato V, Liang Y, Trevisi E, Osorio JS, Xu C, Loor JJ: Hepatic metabolomics and transcriptomics to study susceptibility to ketosis in response to prepartal nutritional management. J Anim Sci Biotechnol. 2019 Dec 18;10:96. doi: 10.1186/s40104-019-0404-z. eCollection 2019. 31867104 Placenta Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Urine Detected by NMR. Urine samples were from 32 Holstein cows that were fed crude protein. Bertram HC, Yde CC, Zhang X, Kristensen NB: Effect of dietary nitrogen content on the urine metabolite profile of dairy cows assessed by nuclear magnetic resonance (NMR)-based metabolomics. J Agric Food Chem. 2011 Dec 14;59(23):12499-505. doi: 10.1021/jf204201f. Epub 2011 Nov 17. 22059599 FDB023896 83292 92258 C04148 17884 C00052383 CPD-1097 43248 Phenylacetylglutamine Suyama, Tadashi; Toyoda, Takeshi; Kanao, Seizo. N-Phenylacetyl amino acids and their homologs. I. N-Acylamino acids. Yakugaku Zasshi (1965), 85(4), 279-83. CODEN: YKKZAJ ISSN:0031-6903. CAN 63:39385 AN 1965:439385 BMDBP00956 Glycine N-acyltransferase Q2KIR7 GLYAT Enzyme