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Record Information
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:24 UTC
Secondary Accession NumbersNone
Metabolite Identification
Common NamePhenylacetylglycine
DescriptionPhenylacetylglycine is an acyl glycine. Acyl glycines are normally minor metabolites of fatty acids. However, the excretion of certain acyl glycines is increased in several inborn errors of metabolism. In certain cases the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. Acyl glycines are produced through the action of glycine N-acyltransferase (EC which is an enzyme that catalyzes the chemical reaction:. acyl-CoA + glycine < -- > CoA + N-acylglycine. Phenylacetylglycine or PAG is a glycine conjugate of phenylacetic acid. Phenylacetic acid may arise from exposure to styrene (plastic) or through the consumption of fruits and vegetables. Phenylacetic acid is used in some perfumes, possessing a honey-like odour in low concentrations, and is also used in penicillin G production. PAG is a putative biomarker of phospholipidosis. Urinary PAG is elevated in animals exhibiting abnormal phospholipid accumulation in many tissues and may thus be useful as a surrogate biomarker for phospholipidosis. (PMID: 15764292 ) The presence of phenylacetylglycine in urine has been confirmed for dogs, rats and mice. However, the presence of this compound in human urine is controversial. GC-MS studies have not found this compound (PMID: 7492634 ) while NMR studies claimed to have identified it (PMID: 21167146 ). It appears that phenylacetylglycine may sometimes be mistaken for phenylacetylglutamine via NMR.
Phenaceturic acidChEBI
Phenacetic acidGenerator
((Phenylacetyl)amino)acetic acidHMDB
Phenylacetyl glycineHMDB
[(Phenylacetyl)amino]acetic acidHMDB
Chemical FormulaC10H11NO3
Average Molecular Weight193.1992
Monoisotopic Molecular Weight193.073893223
IUPAC Name2-(2-phenylacetamido)acetic acid
Traditional Namephenylacetylglycine
CAS Registry Number500-98-1
InChI Identifier
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
  • N-acyl-aliphatic-alpha amino acid
  • Phenylacetamide
  • Benzenoid
  • Monocyclic benzene moiety
  • Secondary 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
StatusDetected and Quantified
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility7.3 mg/mL at 11 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.66 mg/mLALOGPS
pKa (Strongest Acidic)3.99ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity50.17 m3·mol-1ChemAxon
Polarizability19.09 Å3ChemAxon
Number of Rings1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004l-9100000000-134ddfbf19f2ee4e9260View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-9656d3b4670efd4db2e3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-9cf5ff47848cf5bf99b2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positivesplash10-0006-9000000000-f37d59edacbcf679b420View in MoNA
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
SalivaDetected and Quantified19.55 +/- 7.98 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
UrineDetected and Quantified65 +/- 15 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified74.841 +/- 30.788 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    • Mordechai, Hien, ...
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)MaleNormal details
Abnormal Concentrations
UrineDetected and Quantified100 +/- 60 umol/mmol creatinineAdult (>18 years old)BothHeart failure details
UrineDetected and Quantified61.775 +/- 51.294 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
Associated Disorders and Diseases
Disease References
Heart failure
  1. Kang SM, Park JC, Shin MJ, Lee H, Oh J, Ryu do H, Hwang GS, Chung JH: (1)H nuclear magnetic resonance based metabolic urinary profiling of patients with ischemic heart failure. Clin Biochem. 2011 Mar;44(4):293-9. Epub 2010 Dec 15. [21167146 ]
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite ID955
FoodDB IDFDB022266
KNApSAcK IDNot Available
Chemspider ID61452
KEGG Compound IDC05598
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00821
Metagene LinkHMDB00821
PubChem Compound68144
PDB IDNot Available
ChEBI ID27480
Synthesis ReferenceFord, Jared H. Convenient synthesis of phenaceturic acid. Journal of the American Chemical Society (1949), 71 3842.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Wang Y, Holmes E, Nicholson JK, Cloarec O, Chollet J, Tanner M, Singer BH, Utzinger J: Metabonomic investigations in mice infected with Schistosoma mansoni: an approach for biomarker identification. Proc Natl Acad Sci U S A. 2004 Aug 24;101(34):12676-81. Epub 2004 Aug 16. [15314235 ]
  2. Ito T, Kidouchi K, Sugiyama N, Kajita M, Chiba T, Niwa T, Wada Y: Liquid chromatographic-atmospheric pressure chemical ionization mass spectrometric analysis of glycine conjugates and urinary isovalerylglycine in isovaleric acidemia. J Chromatogr B Biomed Appl. 1995 Aug 18;670(2):317-22. [8548022 ]
  3. Matsumoto M, Zhang CH, Kosugi C, Matsumoto I: Gas chromatography-mass spectrometric studies of canine urinary metabolism. J Vet Med Sci. 1995 Apr;57(2):205-11. [7492634 ]
  4. Kang SM, Park JC, Shin MJ, Lee H, Oh J, Ryu do H, Hwang GS, Chung JH: (1)H nuclear magnetic resonance based metabolic urinary profiling of patients with ischemic heart failure. Clin Biochem. 2011 Mar;44(4):293-9. Epub 2010 Dec 15. [21167146 ]
  5. Delaney J, Neville WA, Swain A, Miles A, Leonard MS, Waterfield CJ: Phenylacetylglycine, a putative biomarker of phospholipidosis: its origins and relevance to phospholipid accumulation using amiodarone treated rats as a model. Biomarkers. 2004 May-Jun;9(3):271-90. [15764292 ]


General function:
Involved in glycine N-acyltransferase activity
Specific function:
Mitochondrial acyltransferase which transfers an acyl group to the N-terminus of glycine and glutamine, although much less efficiently. Can conjugate numerous substrates to form a variety of N-acylglycines, with a preference for benzoyl-CoA over phenylacetyl-CoA as acyl donors. Thereby detoxify xenobiotics, such as benzoic acid or salicylic acid, and endogenous organic acids, such as isovaleric acid.
Gene Name:
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Phenylacetyl-CoA + Glycine → Phenylacetylglycine + Coenzyme Adetails
General function:
Involved in glycine N-acyltransferase activity
Specific function:
Acyltransferase which transfers an acyl group to the N-terminus of glutamine. Can use phenylacetyl-CoA as an acyl donor.
Gene Name:
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General function:
Involved in glycine N-acyltransferase activity
Specific function:
Mitochondrial acyltransferase which transfers the acyl group to the N-terminus of glycine. Conjugates numerous substrates, such as arachidonoyl-CoA and saturated medium and long-chain acyl-CoAs ranging from chain-length C8:0-CoA to C18:0-CoA, to form a variety of N-acylglycines. Shows a preference for monounsaturated fatty acid oleoyl-CoA (C18:1-CoA) as an acyl donor. Does not exhibit any activity toward C22:6-CoA and chenodeoxycholoyl-CoA, nor toward serine or alanine.
Gene Name:
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General function:
Involved in glycine N-acyltransferase activity
Specific function:
Acyltransferase which transfers the acyl group to the N- terminus of glycine
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General function:
Involved in damaged DNA binding
Specific function:
Acetyltransferase required for the establishment of sister chromatid cohesion and couple the processes of cohesion and DNA replication to ensure that only sister chromatids become paired together. In contrast to the structural cohesins, the deposition and establishment factors are required only during S phase. Acts by mediating the acetylation of cohesin component SMC3
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