Np mrd loader

Record Information
Version1.0
Created at2022-04-29 04:35:21 UTC
Updated at2022-04-29 04:35:21 UTC
NP-MRD IDNP0083595
Secondary Accession NumbersNone
Natural Product Identification
Common NamePhenylacetylglutamine
DescriptionPhenylacetylglutamine 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 an extremely weak basic (essentially neutral) compound (based on its pKa). Phenylacetylglutamine can be biosynthesized from phenylacetyl-CoA and L-glutamine; which is catalyzed by the enzyme glycine N-acyltransferase. An a N(2)-phenylacetylglutamine having L-configuration. Phenylacetylglutamine is found in Homo sapiens (Urine). It was first documented in 1983 (PMID: 6420430). In humans, phenylacetylglutamine is involved in phenylacetate metabolism (PMID: 22770225) (PMID: 32033212) (PMID: 2791363) (PMID: 8972626) (PMID: 26241311) (PMID: 14709615).
Structure
Thumb
Synonyms
ValueSource
alpha-N-Phenylacetyl-L-glutamineChEBI
Phenylacetyl-L-glutamineChEBI
N2-(2-Phenylacetyl)-L-glutamineKegg
a-N-Phenylacetyl-L-glutamineGenerator
Α-N-phenylacetyl-L-glutamineGenerator
N(2)-(Phenylacetyl)-L-glutamineHMDB
N(2)-(2-Phenylacetyl)-L-glutamineHMDB
N-PhenylacetylglutamineHMDB
N2-(Phenylacetyl)-L-glutamineHMDB
Α-N-phenylacetylglutamineHMDB
alpha-N-PhenylacetylglutamineHMDB
PhenylacetylglutamineChEBI
Chemical FormulaC13H16N2O4
Average Mass264.2771 Da
Monoisotopic Mass264.11101 Da
IUPAC Name(2S)-4-carbamoyl-2-(2-phenylacetamido)butanoic acid
Traditional Namephenylacetylglutamine
CAS Registry NumberNot Available
SMILES
NC(=O)CC[C@H](NC(=O)CC1=CC=CC=C1)C(O)=O
InChI Identifier
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
InChI KeyJFLIEFSWGNOPJJ-JTQLQIEISA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Homo sapiens (Urine)Animalia
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-alpha amino acids
Alternative Parents
Substituents
  • N-acyl-alpha-amino acid
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.35ALOGPS
logP-0.086ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)3.9ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area109.49 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity67.28 m³·mol⁻¹ChemAxon
Polarizability26.55 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0006344
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023896
KNApSAcK IDNot Available
Chemspider ID83292
KEGG Compound IDC04148
BioCyc IDCPD-1097
BiGG ID43248
Wikipedia LinkPhenylacetylglutamine
METLIN IDNot Available
PubChem Compound92258
PDB IDNot Available
ChEBI ID17884
Good Scents IDNot Available
References
General References
  1. Roux A, Xu Y, Heilier JF, Olivier MF, Ezan E, Tabet JC, Junot C: Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer. Anal Chem. 2012 Aug 7;84(15):6429-37. doi: 10.1021/ac300829f. Epub 2012 Jul 17. [PubMed:22770225 ]
  2. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
  3. Zimmerman L, Egestad B, Jornvall H, Bergstrom J: Identification and determination of phenylacetylglutamine, a major nitrogenous metabolite in plasma of uremic patients. Clin Nephrol. 1989 Sep;32(3):124-8. [PubMed:2791363 ]
  4. Shockcor JP, Unger SE, Wilson ID, Foxall PJ, Nicholson JK, Lindon JC: Combined HPLC, NMR spectroscopy, and ion-trap mass spectrometry with application to the detection and characterization of xenobiotic and endogenous metabolites in human urine. Anal Chem. 1996 Dec 15;68(24):4431-5. doi: 10.1021/ac9606463. [PubMed:8972626 ]
  5. Karoum F, Chuang LW, Mosnaim AD, Staub RA, Wyatt RJ: Plasma and cerebrospinal fluid concentration of phenylacetic acid in humans and monkeys. J Chromatogr Sci. 1983 Dec;21(12):546-50. doi: 10.1093/chromsci/21.12.546. [PubMed:6420430 ]
  6. Barrios C, Beaumont M, Pallister T, Villar J, Goodrich JK, Clark A, Pascual J, Ley RE, Spector TD, Bell JT, Menni C: Gut-Microbiota-Metabolite Axis in Early Renal Function Decline. PLoS One. 2015 Aug 4;10(8):e0134311. doi: 10.1371/journal.pone.0134311. eCollection 2015. [PubMed:26241311 ]
  7. Kasumov T, Brunengraber LL, Comte B, Puchowicz MA, Jobbins K, Thomas K, David F, Kinman R, Wehrli S, Dahms W, Kerr D, Nissim I, Brunengraber H: New secondary metabolites of phenylbutyrate in humans and rats. Drug Metab Dispos. 2004 Jan;32(1):10-9. doi: 10.1124/dmd.32.1.10. [PubMed:14709615 ]