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Record Information
Version4.0
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-09-27 07:45:53 UTC
HMDB IDHMDB0000594
Secondary Accession Numbers
  • HMDB00594
Metabolite Identification
Common NameGlutamylphenylalanine
DescriptionGlutamylphenylalanine is a gamma-glutamyl derivative. It is probably formed by transpeptidation between glutathione and the corresponding amino acid, catalyzed by gamma-glutamyl transpeptidase (PMID 237763 ). It can be detected in urine of patients with phenylketonuria, which is a human genetic disorder due to the lack of phenylalanine hydroxylase to metabolize phenylalanine to tyrosine (Wikipedia).
Structure
Thumb
Synonyms
ValueSource
gamma-Glu-pheHMDB
gamma-GlutamylphenylalanineHMDB
H-gamma-Glu-phe-OHHMDB
H-Glu(phe-OH)-OHHMDB
L-gamma-Glutamyl-L-phenylalanineHMDB
N-(gamma-L-Glutamyl)phenylalanineHMDB
N-L-gamma-Glutamyl-3-phenyl-L-alanineHMDB
N-L-gamma-Glutamyl-L-phenylalanineHMDB
gamma-Glutamylphenylalanine, (D-phe-D-glu)-isomerMeSH
gamma-Glutamylphenylalanine, (L-phe-D-glu)-isomerMeSH
Chemical FormulaC14H18N2O5
Average Molecular Weight294.3031
Monoisotopic Molecular Weight294.121571696
IUPAC Name(2S)-2-amino-4-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}butanoic acid
Traditional Namegamma-glutamylphenylalanine
CAS Registry Number7432-24-8
SMILES
N[C@@H](CCC(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C14H18N2O5/c15-10(13(18)19)6-7-12(17)16-11(14(20)21)8-9-4-2-1-3-5-9/h1-5,10-11H,6-8,15H2,(H,16,17)(H,18,19)(H,20,21)/t10-,11-/m0/s1
InChI KeyXHHOHZPNYFQJKL-QWRGUYRKSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as phenylalanine and derivatives. These are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentPhenylalanine and derivatives
Alternative Parents
Substituents
  • Phenylalanine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • 3-phenylpropanoic-acid
  • Alpha-amino acid
  • Amphetamine or derivatives
  • L-alpha-amino acid
  • Monocyclic benzene moiety
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • Amino acid
  • Carboximidic acid
  • Carboximidic acid derivative
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboxylic acid
  • Organic nitrogen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organooxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect

Health effect:

  Health condition:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

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 Solubility0.61 g/LALOGPS
logP-2.1ALOGPS
logP-2.1ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)1.82ChemAxon
pKa (Strongest Basic)9.31ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area129.72 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity73.2 m³·mol⁻¹ChemAxon
Polarizability29.7 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, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-014i-0900000000-3c15b0ec8b0aa7b4f562View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-1490000000-8a194f7de818cb11e47bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03xs-2960000000-8471d66cf80c273476e9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9200000000-cee53e3b344fef2f519eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0290000000-f75848c2ae5c1246f8d8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0035-1790000000-fd452e6dee821306584bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02fx-9500000000-9ba84b5fd475503d8cd7View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Feces
  • Urine
Tissue Location
  • Kidney
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
Not Available
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
UrineDetected and Quantified43.00 (8.00-78.00) umol/mmol creatinineNewborn (0-30 days old)BothPhenylketonuria details
Associated Disorders and Diseases
Disease References
Phenylketonuria
  1. Peck H, Pollitt RJ: The occurrence of gamma-glutamylphenylalanine in the urine of newborn phenylketonurics. Clin Chim Acta. 1979 Jun 15;94(3):237-40. [PubMed:466810 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB003618
KNApSAcK IDNot Available
Chemspider ID99868
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5573
PubChem Compound111299
PDB IDNot Available
ChEBI ID89582
References
Synthesis ReferenceBodnaryk, Robert P. Preparative-scale enzymic synthesis of g-L-glutamyl-L-phenylalanine. Insect Biochemistry (1972), 2(1), 49-52.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Peck H, Pollitt RJ: The occurrence of gamma-glutamylphenylalanine in the urine of newborn phenylketonurics. Clin Chim Acta. 1979 Jun 15;94(3):237-40. [PubMed:466810 ]
  2. Bridges RJ, Meister A: gamma-Glutamyl amino acids. Transport and conversion to 5-oxoproline in the kidney. J Biol Chem. 1985 Jun 25;260(12):7304-8. [PubMed:3997870 ]
  3. Orlowski M, Wilk S: Intermediates of the gamma-glutamyl cycle in mouse tissues. Influence of administration of amino acids on pyrrolidone carboxylate and gamma-glutamyl amino acids. Eur J Biochem. 1975 May 6;53(2):581-90. [PubMed:237763 ]
  4. Kamerling JP, Aarsen GJ, Duran M, de Bree PK, van Sprang FJ, Wadman SK: Chromatographic determination and mass spectrometric identification of gamma-glutamylphenylalanine, a urinary constituent in phenylketonuria. Clin Chim Acta. 1980 Mar 28;102(2-3):137-45. [PubMed:7371187 ]
  5. Lawson LD, Gardner CD: Composition, stability, and bioavailability of garlic products used in a clinical trial. J Agric Food Chem. 2005 Aug 10;53(16):6254-61. [PubMed:16076102 ]
  6. Jandke J, Spiteller G: Dipeptide analysis in human urine. J Chromatogr. 1986 Oct 31;382:39-45. [PubMed:3782411 ]