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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:24 UTC
HMDB IDHMDB00821
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 2.3.1.13) 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.
Structure
Thumb
Synonyms
ValueSource
N-PhenacetylglycineChEBI
N-PhenylacetylglycineChEBI
Phenaceturic acidChEBI
PhenacetylglycineChEBI
2-[(2-Phenylacetyl)amino]acetateGenerator
PhenacetateGenerator
Phenacetic acidGenerator
((Phenylacetyl)amino)acetic acidHMDB
N-(Phenylacetyl)-glycineHMDB
N-(Phenylacetyl)glycineHMDB
PAAHMDB
PAGHMDB
PhenaceturateHMDB
Phenylacetyl glycineHMDB
[(Phenylacetyl)amino]acetateHMDB
[(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
SMILES
OC(=O)CNC(=O)CC1=CC=CC=C1
InChI Identifier
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)
InChI KeyInChIKey=UTYVDVLMYQPLQB-UHFFFAOYSA-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
  • 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
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility7.3 mg/mL at 11 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.66 mg/mLALOGPS
logP0.51ALOGPS
logP0.51ChemAxon
logS-2.5ALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
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
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
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C 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
BiofluidStatusValueAgeSexConditionReferenceDetails
SalivaDetected and Quantified19.55 +/- 7.98 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
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
Normal
    • Mordechai, Hien, ...
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)MaleNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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, ...
details
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
METLIN ID4237
PubChem Compound68144
PDB IDNot Available
ChEBI ID27480
References
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 ]

Enzymes

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:
GLYAT
Uniprot ID:
Q6IB77
Molecular weight:
18506.33
Reactions
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:
GLYATL1
Uniprot ID:
Q969I3
Molecular weight:
35100.895
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:
GLYATL2
Uniprot ID:
Q8WU03
Molecular weight:
34277.055
General function:
Involved in glycine N-acyltransferase activity
Specific function:
Acyltransferase which transfers the acyl group to the N- terminus of glycine
Gene Name:
GLYATL3
Uniprot ID:
Q5SZD4
Molecular weight:
32703.3
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
Gene Name:
ESCO1
Uniprot ID:
Q5FWF5
Molecular weight:
94982.2