General Information of MET (ID: META00277)
Name Gamma-Glutamylphenylalanine
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(2S)-2-Amino-4-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}butanoate; (2S)-2-Amino-4-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}butanoic acid; H-gamma-Glu-Phe-OH; L-g-Glutamyl-L-phenylalanine; L-gamma-Glu-L-Phe; L-gamma-Glutamyl-L-phenylalanine; N-(gamma-L-Glutamyl)phenylalanine; N-L-g-Glutamyl-L-phenylalanine; N-L-gamma-Glutamylphenylalanine; N-gamma-Glutamylphenylalanine; N-gamma-L-Glutamyl-L-phenylalanine; g-Glu-Phe; g-Glutamylphenylalanine; gamma-Glu-Phe; gamma-Glutamylphenylalanine; gamma-L-Glu-L-Phe; gamma-L-Glutamyl-L-phenylalanine
Source Endogenous;Food;TCM Ingredients
Structure Type   Amino acids, peptides, and analogues  (Click to Show/Hide the Complete Structure Type Hierarchy)
Organic acids and derivatives
Carboxylic acids and derivatives
Amino acids, peptides, and analogues
PubChem CID
111299
HMDB ID
HMDB0000594
Formula
C14H18N2O5
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
ChEBI ID
89582
Physicochemical Properties Molecular Weight 294.3 Topological Polar Surface Area 130
XlogP -3 Complexity 380
Heavy Atom Count 21 Rotatable Bond Count 8
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 6
Function
gamma-Glutamylphenylalanine is a dipeptide composed of gamma-glutamate and phenylalanine, and is a proteolytic breakdown product of larger proteins. It is probably formed by transpeptidation between glutathione and the corresponding amino acid, catalyzed by gamma-glutamyl transpeptidase. gamma-Glutamylphenylalanine belongs to the family of N-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. gamma-Glutamylphenylalanine 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. It can be detected in the urine of patients with phenylketonuria, which is a human genetic disorder due to the lack of phenylalanine hydroxylase to metabolize phenylalanine to tyrosine. gamma-Glutamylphenylalanine is found in adzuki bean, onion (Allium cepa), garlic (Allium sativum), and soybean.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Hydrolases (EC 3)
            Sulfatase sulf-1 (SULF1) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Knockdown (shRNA) of SULF1
                      Induced Change Gamma-Glutamylphenylalanine concentration: increase (FC = 1.77 - 1.88)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Ovarian cancer [ICD-11: 2C73]
                      Details It is reported that knockdown of SULF1 leads to the increase of gamma-Glutamylphenylalanine levels compared with control group.
      Pore-forming PNC peptide (PNC)
            Cellular tumor antigen p53 (TP53) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [2]
                      Introduced Variation Knockout of TP53
                      Induced Change Gamma-Glutamylphenylalanine concentration: increase (Log2 FC=1.06)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Colon cancer [ICD-11: 2B90]
                      Details It is reported that knockout of TP53 leads to the increase of gamma-Glutamylphenylalanine levels compared with control group.
References
1 Erratum to: Loss of HSulf-1 promotes altered lipid metabolism in ovarian cancer. Cancer Metab. 2014 Nov 4;2:24.
2 Integrative omics analysis of p53-dependent regulation of metabolism. FEBS Lett. 2018 Feb;592(3):380-393.

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