Record Information
Version1.0
Creation date2011-09-21 00:36:32 UTC
Update date2018-05-29 01:53:09 UTC
Primary IDFDB023896
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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. [HMDB]
CAS Number28047-15-6
Structure
Thumb
Synonyms
SynonymSource
alpha-N-Phenylacetyl-L-glutamineChEBI
Phenylacetyl-L-glutamineChEBI
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-glutamineHMDB
N-PhenylacetylglutamineHMDB
N2-(Phenylacetyl)-L-glutamineHMDB
Α-N-phenylacetylglutamineHMDB
alpha-N-PhenylacetylglutamineHMDB
PhenylacetylglutamineChEBI
L-N(sup2)-(Phenylacetyl)glutaminehmdb
α-N-phenylacetyl-L-glutamineGenerator
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC13H16N2O4
IUPAC name(2S)-4-carbamoyl-2-(2-phenylacetamido)butanoic acid
InChI IdentifierInChI=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
Isomeric SMILESNC(=O)CC[C@H](NC(=O)CC1=CC=CC=C1)C(O)=O
Average Molecular Weight264.2771
Monoisotopic Molecular Weight264.11100701
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

Source:

Biological location:

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
    Predicted GC-MSalpha-N-Phenylacetyl-L-glutamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9520000000-5d0fcec2811fdda6e493Spectrum
    Predicted GC-MSalpha-N-Phenylacetyl-L-glutamine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-006x-9210000000-b1470e0601bcb76fcddaSpectrum
    MS/MS
    TypeDescriptionSplash KeyView
    MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0002-0900000000-16da6849ac342b179bb0Spectrum
    MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-00di-0190000000-0e5d477fb2aa8bfecabaSpectrum
    MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001l-0090000000-b74aefa0573c8e2d497cSpectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-1590000000-43b5b1154ff8c459a8e4Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-5950000000-d9a6090fc4170f3cbec0Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9300000000-74c33c21f286a44eb712Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0290000000-c95723e9e5991b3a938fSpectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02td-5980000000-c54142cded19fc0b1975Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9200000000-744617f4104fc833e5d6Spectrum
    NMRNot Available
    ChemSpider ID83292
    ChEMBL IDNot Available
    KEGG Compound IDC04148
    Pubchem Compound ID92258
    Pubchem Substance IDNot Available
    ChEBI IDNot Available
    Phenol-Explorer IDNot Available
    DrugBank IDNot Available
    HMDB IDHMDB06344
    CRC / DFC (Dictionary of Food Compounds) IDNot Available
    EAFUS IDNot Available
    Dr. Duke IDNot Available
    BIGG ID43248
    KNApSAcK IDNot Available
    HET IDNot Available
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDNot Available
    SuperScent IDNot Available
    Wikipedia IDPhenylacetylglutamine
    Phenol-Explorer Metabolite IDNot Available
    Duplicate IDSNot Available
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    FoodReference
    Biological Effects and Interactions
    Health Effects / BioactivitiesNot Available
    EnzymesNot Available
    Pathways
    NameSMPDB LinkKEGG Link
    Phenylacetate MetabolismSMP00126 map00360
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    FlavoursNot Available
    Files
    MSDSNot Available
    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    Content Reference