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Glutamyl-Phenylalanine

July 21, 2017
Common Name

Glutamyl-Phenylalanine Description

Glutamyl-Phenylalanine is a dipeptide composed of glutamate and phenylalanine. It is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an Expected metabolite. Structure

MOLSDFPDBSMILESInChI

Structure for HMDB28826 (Glutamyl-Phenylalanine)

Synonyms

Value Source e-F DipeptideHMDB EF dipeptideHMDB Glu-pheHMDB Glutamate phenylalanine dipeptideHMDB Glutamate-phenylalanine dipeptideHMDB GlutamylphenylalanineHMDB L-Glutamyl-L-phenylalanineHMDB

Chemical Formlia

C14H17N2O5 Average Molecliar Weight

293.2952 Monoisotopic Molecliar Weight

293.113746664 IUPAC Name

4-amino-4-[(1-carboxy-2-phenylethyl)carbamoyl]butanoate Traditional Name

4-amino-4-[(1-carboxy-2-phenylethyl)carbamoyl]butanoate CAS Registry Number

Not Available SMILES

NC(CCC([O-])=O)C(=O)NC(CC1=CC=CC=C1)C(O)=O

InChI Identifier

InChI=1S/C14H18N2O5/c15-10(6-7-12(17)18)13(19)16-11(14(20)21)8-9-4-2-1-3-5-9/h1-5,10-11H,6-8,15H2,(H,16,19)(H,17,18)(H,20,21)/p-1

InChI Key

XMBSYZWANAQXEV-UHFFFAOYSA-M Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Kingdom

Chemical entities Super Class

Organic compounds Class

Organic acids and derivatives Sub Class

Carboxylic acids and derivatives Direct Parent

Dipeptides Alternative Parents

  • Phenylalanine and derivatives
  • Glutamic acid and derivatives
  • N-acyl-alpha amino acids
  • Alpha amino acid amides
  • Phenylpropanoic acids
  • Amphetamines and derivatives
  • Amino fatty acids
  • N-acyl amines
  • Dicarboxylic acids and derivatives
  • Secondary carboxylic acid amides
  • Amino acids
  • Carboxylic acids
  • Organopnictogen compounds
  • Hydrocarbon derivatives
  • Carbonyl compounds
  • Monoalkylamines
  • Organic oxides
  • Organic anions

    • Substituents

  • Alpha-dipeptide
  • Phenylalanine or derivatives
  • Glutamic acid or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • 3-phenylpropanoic-acid
  • Alpha-amino acid or derivatives
  • Amphetamine or derivatives
  • Amino fatty acid
  • Fatty amide
  • N-acyl-amine
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Monocyclic benzene moiety
  • Benzenoid
  • Amino acid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Carboxylic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Primary aliphatic amine
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic anion
  • Aromatic homomonocyclic compound

    • Molecliar Framework

    Aromatic homomonocyclic compounds External Descriptors

    Not Available Ontology Status

    Expected but not Quantified Origin

  • Endogenous

    • Biofunction

    Not Available Application

    Not Available Cellliar locations

    Not Available Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogP-2.38Extrapolated

    Predicted Properties

    Property Value Source Water Solubility1.46 mg/mLALOGPS logP-1.7ALOGPS logP-2.4ChemAxon logS-2.3ALOGPS pKa (Strongest Acidic)3.33ChemAxon pKa (Strongest Basic)8.45ChemAxon Physiological Charge-1ChemAxon Hydrogen Acceptor Count6ChemAxon Hydrogen Donor Count3ChemAxon Polar Surface Area132.55 Å2ChemAxon Rotatable Bond Count8ChemAxon Refractivity84.04 m3·mol-1ChemAxon Polarizability29.17 Å3ChemAxon Number of Rings1ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Not Available Biological Properties Cellliar Locations

    Not Available Biofluid Locations

    Not Available Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations Not Available Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    Not Available DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    Not Available KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Not Available NuGOwiki Link

    HMDB28826 Metagene Link

    HMDB28826 METLIN ID

    Not Available PubChem Compound

    Not Available PDB ID

    Not Available ChEBI ID

    Not Available

    Product: ISCK03

    References Synthesis Reference Not Available 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. Sun R, Zhang J, Xiong M, Chen Y, Yin L, Pu Y: Metabonomics biomarkers for subacute toxicity screening for benzene exposure in mice. J Toxicol Environ Health A. 2012;75(18):1163-73. doi: 10.1080/15287394.2012.699858. [PubMed:22891888 ]
    6. Suzuki H, Kajimoto Y, Kumagai H: Improvement of the bitter taste of amino acids through the transpeptidation reaction of bacterial gamma-glutamyltranspeptidase. J Agric Food Chem. 2002 Jan 16;50(2):313-8. [PubMed:11782200 ]
    7. Vallverdu-Queralt A, Medina-Remon A, Casals-Ribes I, Amat M, Lamuela-Raventos RM: A metabolomic approach differentiates between conventional and organic ketchups. J Agric Food Chem. 2011 Nov 9;59(21):11703-10. doi: 10.1021/jf202822s. Epub 2011 Oct 11. [PubMed:21958116 ]

    PMID: 23505009

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