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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:00 UTC
HMDB IDHMDB00594
Secondary Accession NumbersNone
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
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 KeyInChIKey=XHHOHZPNYFQJKL-QWRGUYRKSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as gamma-glutamyl amino acids. These are dipeptides consisting of any C-terminal amino acid having a gamma-glutamyl residue attached at the N alpha-position.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentGamma-glutamyl amino acids
Alternative Parents
Substituents
  • Gamma-glutamyl alpha-amino acid
  • N-acyl-aliphatic-alpha amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • 3-phenylpropanoic-acid
  • N-acyl-l-alpha-amino acid
  • L-alpha-amino acid
  • Amphetamine or derivatives
  • Alpha-amino acid or derivatives
  • N-substituted-alpha-amino acid
  • Alpha-amino acid
  • Amino fatty acid
  • Fatty acyl
  • Benzenoid
  • N-acyl-amine
  • Fatty amide
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity73.2 m3·mol-1ChemAxon
Polarizability29.7 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Urine
Tissue Location
  • Kidney
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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. [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
NuGOwiki LinkHMDB00594
Metagene LinkHMDB00594
METLIN ID5573
PubChem Compound111299
PDB IDNot Available
ChEBI IDNot Available
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. [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. [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. [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. [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. [16076102 ]
  6. Jandke J, Spiteller G: Dipeptide analysis in human urine. J Chromatogr. 1986 Oct 31;382:39-45. [3782411 ]