1.0 2016-09-30 22:37:06 UTC 2020-06-04 20:16:15 UTC BMDB0000821 BMDB00821 Phenylacetylglycine N-Phenylacetylglycine, also known as phenaceturic acid or phenacetate, 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-Phenylacetylglycine is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). N-Phenylacetylglycine exists in all eukaryotes, ranging from yeast to humans. N-Phenacetylglycine N-Phenylacetylglycine Phenaceturic acid Phenacetylglycine Phenacetate Phenacetic acid ((Phenylacetyl)amino)acetic acid N-(Phenylacetyl)-glycine N-(Phenylacetyl)glycine PAA PAG Phenaceturate Phenylacetyl glycine [(Phenylacetyl)amino]acetate [(Phenylacetyl)amino]acetic acid Phenylacetylglycine C10H11NO3 193.1992 193.073893223 2-(2-phenylacetamido)acetic acid phenylacetylglycine 500-98-1 OC(=O)CNC(=O)CC1=CC=CC=C1 InChI=1S/C10H11NO3/c12-9(11-7-10(13)14)6-8-4-2-1-3-5-8/h1-5H,6-7H2,(H,11,12)(H,13,14) UTYVDVLMYQPLQB-UHFFFAOYSA-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-acylglycine monocarboxylic acid monocarboxylic acid amide Solid water_solubility 7.3 mg/mL at 11 °C logp 0.51 ALOGPS logs -2.46 ALOGPS logp 0.51 ChemAxon pka_strongest_acidic 3.99 ChemAxon pka_strongest_basic -2.9 ChemAxon iupac 2-(2-phenylacetamido)acetic acid ChemAxon average_mass 193.1992 ChemAxon mono_mass 193.073893223 ChemAxon smiles OC(=O)CNC(=O)CC1=CC=CC=C1 ChemAxon formula C10H11NO3 ChemAxon inchi InChI=1S/C10H11NO3/c12-9(11-7-10(13)14)6-8-4-2-1-3-5-8/h1-5H,6-7H2,(H,11,12)(H,13,14) ChemAxon inchikey UTYVDVLMYQPLQB-UHFFFAOYSA-N ChemAxon polar_surface_area 66.4 ChemAxon refractivity 50.17 ChemAxon polarizability 19.09 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 3 ChemAxon donor_count 2 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 Specdb::NmrTwoD 1499 Specdb::MsIr 887 Specdb::MsIr 888 Specdb::MsIr 889 Specdb::CMs 2851 Specdb::CMs 27216 Specdb::CMs 32194 Specdb::CMs 32195 Specdb::CMs 37786 Specdb::CMs 99612 Specdb::CMs 99613 Specdb::CMs 99614 Specdb::CMs 160084 Specdb::CMs 1077645 Specdb::CMs 1077647 Specdb::CMs 1077649 Specdb::NmrOneD 1275 Specdb::NmrOneD 1556 Specdb::NmrOneD 5059 Specdb::NmrOneD 5060 Specdb::NmrOneD 166504 Specdb::MsMs 1170 Specdb::MsMs 1171 Specdb::MsMs 1172 Specdb::MsMs 4701 Specdb::MsMs 178989 Specdb::MsMs 178990 Specdb::MsMs 178991 Specdb::MsMs 181314 Specdb::MsMs 181315 Specdb::MsMs 181316 Specdb::MsMs 2236513 Specdb::MsMs 2236885 Specdb::MsMs 2238645 Specdb::MsMs 2238911 Specdb::MsMs 2240643 Specdb::MsMs 2241072 Specdb::MsMs 2242677 Specdb::MsMs 2243144 Specdb::MsMs 2248538 Specdb::MsMs 2250507 Specdb::MsMs 2251081 Specdb::MsMs 2251345 Specdb::MsMs 2251869 Specdb::MsMs 2449555 Specdb::MsMs 2449556 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 Milk Detected but not quantified in conventional whole milk Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386 Milk Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386 doi: 10.1007/s11306-009-0160-8 Ruminal Fluid Detected by NMR in bovines in growth and fattening stages. Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub 2012 Jun 15. 22706048 Ruminal Fluid Detected by NMR in bovines in growth and fattening stages. Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub 2012 Jun 15. 22706048 Ruminal Fluid Detected by NMR in bovines in growth and fattening stages. Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub 2012 Jun 15. 22706048 C05598 FDB022266 61452 68144 27480 4237 CPD-11715 Ford, Jared H. Convenient synthesis of phenaceturic acid. Journal of the American Chemical Society (1949), 71 3842. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386 Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386 doi: 10.1007/s11306-009-0160-8