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Record Information
Version3.6
Creation Date2007-05-23 01:14:41 UTC
Update Date2016-02-11 01:07:29 UTC
HMDB IDHMDB06344
Secondary Accession NumbersNone
Metabolite Identification
Common NameAlpha-N-Phenylacetyl-L-glutamine
DescriptionPhenylacetylglutamine 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.(Wikipedia).
Structure
Thumb
Synonyms
ValueSource
alpha-N-Phenylacetyl-L-glutamineChEBI
Phenylacetyl-L-glutamineChEBI
PhenylacetylglutamineChEBI
a-N-Phenylacetyl-L-glutamineGenerator
α-N-phenylacetyl-L-glutamineGenerator
(2S)-5-amino-5-oxo-2-[(2-Phenylacetyl)amino]pentanoateGenerator
N(2)-(Phenylacetyl)-L-glutamineHMDB
Chemical FormulaC13H16N2O4
Average Molecular Weight264.2771
Monoisotopic Molecular Weight264.11100701
IUPAC Name(2S)-4-carbamoyl-2-(2-phenylacetamido)butanoic acid
Traditional Namephenylacetylglutamine
CAS Registry Number28047-15-6
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 KeyInChIKey=JFLIEFSWGNOPJJ-JTQLQIEISA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as n-acyl-aliphatic-alpha amino acids. These are alpha amino acids carrying a N-acylated aliphatic chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-aliphatic-alpha amino acids
Alternative Parents
Substituents
  • N-acyl-aliphatic-alpha amino acid
  • N-acyl-l-alpha-amino acid
  • Phenylacetamide
  • Amino fatty acid
  • Fatty acyl
  • Benzenoid
  • Fatty amide
  • Monocyclic benzene moiety
  • Secondary carboxylic acid amide
  • Primary carboxylic acid amide
  • Carboxamide group
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Microbial
Biofunction
  • Protein synthesis, amino acid biosynthesis
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Extracellular
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.39 mg/mLALOGPS
logP-0.35ALOGPS
logP-0.086ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)3.9ChemAxon
pKa (Strongest Basic)-0.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area109.49 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity67.28 m3·mol-1ChemAxon
Polarizability26.55 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Phenylacetate MetabolismSMP00126map00360
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
BloodDetected and Quantified3.34 +/- 0.31 uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified34.0 (4.5-70.0) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified13.731 +/- 2.994 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified47.03 (3.84 - 85.51) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified71.0 +/- 6.0 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothHemodialysis patients with colons details
BloodDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothHemodialysis patients without colons details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Hypertension (mild)
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Hypertension (mild)
details
UrineDetected and Quantified27.595 +/- 24.094 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023896
KNApSAcK IDNot Available
Chemspider ID83292
KEGG Compound IDC04148
BioCyc IDCPD-1097
BiGG ID43248
Wikipedia LinkPhenylacetylglutamine
NuGOwiki LinkHMDB06344
Metagene LinkHMDB06344
METLIN IDNot Available
PubChem Compound92258
PDB IDNot Available
ChEBI ID17884
References
Synthesis ReferenceSuyama, 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
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [6420430 ]
  2. 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. [2791363 ]
  3. 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. [8972626 ]