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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2007-05-23 01:14:41 UTC
Update Date2018-05-30 17:27:11 UTC
HMDB IDHMDB0006344
Secondary Accession Numbers
  • HMDB06344
Metabolite Identification
Common NamePhenylacetylglutamine
DescriptionPhenylacetylglutamine is a product formed from 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 such as the dog, cat, rat, monkey, sheep, and horse do not excrete this compound. Phenylacetyl-CoA and L-glutamine react to form phenylacetylglutamine 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 polypeptide species distinct from glycine-N-acyltransferase. Phenylacetylglutamine is a major nitrogenous metabolite that accumulates in uremia (PMID: 2791363 , 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 ).
Structure
Thumb
Synonyms
ValueSource
Phenylacetyl-L-glutamineChEBI
PhenylacetylglutamineChEBI
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-glutamineGenerator
N-PhenylacetylglutamineHMDB
N2-(Phenylacetyl)-L-glutamineHMDB
α-N-PhenylacetylglutamineHMDB
alpha-N-PhenylacetylglutamineGenerator
alpha-N-Phenylacetyl-L-glutamineGenerator
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 KeyJFLIEFSWGNOPJJ-JTQLQIEISA-N
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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkNot Available
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

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 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9520000000-5d0fcec2811fdda6e493View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006x-9210000000-b1470e0601bcb76fcddaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0002-0900000000-16da6849ac342b179bb0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-00di-0190000000-0e5d477fb2aa8bfecabaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001l-0090000000-b74aefa0573c8e2d497cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-1590000000-43b5b1154ff8c459a8e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-5950000000-d9a6090fc4170f3cbec0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9300000000-74c33c21f286a44eb712View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0290000000-c95723e9e5991b3a938fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02td-5980000000-c54142cded19fc0b1975View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9200000000-744617f4104fc833e5d6View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not Quantified Adult (>18 years old)BothNormal details
BloodDetected and Quantified3.34 +/- 0.31 uMAdult (>18 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
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 Quantified Adult (>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
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not Quantified Adult (>18 years old)BothHemodialysis patients with colons details
BloodDetected but not Quantified Adult (>18 years old)BothHemodialysis patients without colons details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
UrineDetected but not Quantified Adult (>18 years old)Both
Hypertension (mild)
details
UrineDetected but not Quantified Adult (>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 References
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Eosinophilic esophagitis
  1. (). Mordechai, Hien, and David S. Wishart. .
Associated OMIM IDs
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
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. [PubMed: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. [PubMed: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. [PubMed:8972626 ]