Back to Compounds

Showing Compound Phenylacetylglycine (FDB022266)

Record Information
Version1.0
Creation date2011-09-21 00:11:14 UTC
Update date2019-11-26 03:21:02 UTC
Primary IDFDB022266
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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) [HMDB]
CAS Number500-98-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
N-PhenacetylglycineChEBI
N-PhenylacetylglycineChEBI
Phenaceturic acidChEBI
PhenacetylglycineChEBI
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
PhenylacetylglycineMeSH
((phenylacetyl)amino)acetic acidhmdb
N-(phenylacetyl)-Glycinehmdb
phenylacetyl glycinehmdb
Predicted Properties
PropertyValueSource
Water Solubility0.66 g/LALOGPS
logP0.51ALOGPS
logP0.51ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)3.99ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity50.17 m³·mol⁻¹ChemAxon
Polarizability19.09 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H11NO3
IUPAC name2-(2-phenylacetamido)acetic acid
InChI IdentifierInChI=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 KeyUTYVDVLMYQPLQB-UHFFFAOYSA-N
Isomeric SMILESOC(=O)CNC(=O)CC1=CC=CC=C1
Average Molecular Weight193.1992
Monoisotopic Molecular Weight193.073893223
Classification
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
Ontology
Physiological effect

Health effect:

Disposition

Biological location:

Source:

Foods
  • Dairy products
  • Eggs
  • Meats

    • Grains:

    Nuts and legumes:

    Physico-Chemical Properties - Experimental
    Physico-Chemical Properties - Experimental
    PropertyValueReference
    Physical stateSolid
    Physical DescriptionNot Available
    Mass CompositionNot Available
    Melting PointNot Available
    Boiling PointNot Available
    Experimental Water SolubilityNot Available
    Experimental logPNot Available
    Experimental pKaNot Available
    Isoelectric pointNot Available
    ChargeNot Available
    Optical RotationNot Available
    Spectroscopic UV DataNot Available
    DensityNot Available
    Refractive IndexNot Available
    Spectra
    Spectra
    EI-MS/GC-MS
    TypeDescriptionSplash KeyView
    GC-MSPhenylacetylglycine, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-96f6d1819364e0910bebSpectrum
    GC-MSPhenylacetylglycine, non-derivatized, GC-MS Spectrumsplash10-0udl-5930000000-6e0622de46a05b80d685Spectrum
    GC-MSPhenylacetylglycine, non-derivatized, GC-MS Spectrumsplash10-0006-9610000000-b8948d031afc0e4b8f78Spectrum
    GC-MSPhenylacetylglycine, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-96f6d1819364e0910bebSpectrum
    GC-MSPhenylacetylglycine, non-derivatized, GC-MS Spectrumsplash10-0udl-5930000000-6e0622de46a05b80d685Spectrum
    GC-MSPhenylacetylglycine, non-derivatized, GC-MS Spectrumsplash10-0006-9610000000-b8948d031afc0e4b8f78Spectrum
    Predicted GC-MSPhenylacetylglycine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9500000000-50b56f103c1a79f65878Spectrum
    Predicted GC-MSPhenylacetylglycine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-006x-9200000000-5d39e42ac2b4d7b6f726Spectrum
    Predicted GC-MSPhenylacetylglycine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSPhenylacetylglycine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSPhenylacetylglycine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSPhenylacetylglycine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    MS/MS
    TypeDescriptionSplash KeyView
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004l-9100000000-134ddfbf19f2ee4e92602012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-9656d3b4670efd4db2e32012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-9cf5ff47848cf5bf99b22012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positivesplash10-0006-9000000000-f37d59edacbcf679b4202012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0006-9200000000-92c7f1e2376eb0e84b362021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-002f-9200000000-c48677787f705755d93f2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0006-9300000000-dd5f78904d0d0dacb6412021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0006-9300000000-1acb6b8d75e7381ccbde2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0596-9100000000-415a6a1ccc4a5a25ad4f2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-002f-9100000000-52063d451d15512ae6522021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0006-9000000000-b4cfc8b9dad7406c720f2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-002f-9000000000-88eadbe8bb1b30f341b02021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-abf76489fbf1b18e56aa2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-00di-9000000000-1168dca79ce76e8ff7442021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-709de7804cd48ddac3b52021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-00di-9000000000-668624127e5eb3cd947a2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-f0284ab582fc7a2b28c42021-09-20View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dl-9600000000-96499e21a08e5d1900402016-09-12View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00fr-9200000000-aeac60944271030f97512016-09-12View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00bc-9000000000-4caba04f2e229a8013b42016-09-12View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-899f25422883181dbe572016-09-12View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-4900000000-433c13250fe2463708f42016-09-12View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-9200000000-0b6ae74cd7a7ddce62d72016-09-12View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-e21745e55a3af36629b32021-09-22View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-078d0d5a533b721686812021-09-22View Spectrum
    NMR
    TypeDescriptionView
    1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Spectrum
    1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
    1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
    1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
    1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Spectrum
    2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
    ChemSpider ID61452
    ChEMBL IDCHEMBL458497
    KEGG Compound IDC05598
    Pubchem Compound ID68144
    Pubchem Substance IDNot Available
    ChEBI IDNot Available
    Phenol-Explorer ID955
    DrugBank IDNot Available
    HMDB IDHMDB00821
    CRC / DFC (Dictionary of Food Compounds) IDNot Available
    EAFUS IDNot Available
    Dr. Duke IDNot Available
    BIGG IDNot Available
    KNApSAcK IDNot Available
    HET IDNot Available
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDNot Available
    SuperScent IDNot Available
    Wikipedia IDNot Available
    Phenol-Explorer Metabolite ID955
    Duplicate IDSNot Available
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    FoodReference
    Biological Effects and Interactions
    Health Effects / BioactivitiesNot Available
    Enzymes
    NameGene NameUniProt ID
    Glycine N-acyltransferaseGLYATQ6IB77
    Glycine N-acyltransferase-like protein 1GLYATL1Q969I3
    Glycine N-acyltransferase-like protein 2GLYATL2Q8WU03
    Glycine N-acyltransferase-like protein 3GLYATL3Q5SZD4
    N-acetyltransferase ESCO1ESCO1Q5FWF5
    PathwaysNot Available
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    FlavoursNot Available
    Files
    MSDSshow
    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    Content Reference