Details of Metabolite

General Information of MET (ID: META00601)
Name Gamma-Glutamylvaline
Synonyms   Click to Show/Hide Synonyms of This Metabolite
L-gamma-Glu-L-Val; L-gamma-Glutamyl-L-valine; N-L-gamma-Glutamyl-L-valine; N-L-gamma-Glutamylvaline; N-gamma-Glutamylvaline; N-gamma-L-Glutamyl-L-valine; g-Glutamylvaline; gamma-Glu-Val; gamma-Glutamylvaline; gamma-L-Glu-L-Val; gamma-L-Glutamyl-L-valine
Source Aliphatic acyclic compounds
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
7015683
HMDB ID
HMDB0011172
Formula
C10H18N2O5
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
68848
ChemSpider ID
5378716
Physicochemical Properties Molecular Weight 246.26 Topological Polar Surface Area 130
XlogP -2.8 Complexity 303
Heavy Atom Count 17 Rotatable Bond Count 7
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 6
Function
gamma-Glutamylvaline is a dipeptide composed of gamma-glutamate and valine. 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. gamma-Glutamylvaline 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. It is found in urine.
Regulatory Network
Full List of Protein(s) Regulated by This Metabolite
      Basigin (BAS)
            Intercellular adhesion molecule 1 (ICAM1) 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 Gamma-Glutamylvaline addition (16 hours)
                      Induced Change ICAM1 protein expression levels: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Peritonitis [ICD-11: DC50]
                      Details It is reported that gamma-glutamylvaline addition causes the decrease of ICAM1 protein expression compared with control group.
      Chemokine (CK)
            Monocyte chemotactic and activating factor (CCL2) 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 Gamma-Glutamylvaline addition (2 hours)
                      Induced Change CCL2 protein expression levels: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Peritonitis [ICD-11: DC50]
                      Details It is reported that gamma-glutamylvaline addition causes the decrease of CCL2 protein expression compared with control group.
      Immunoglobulin (IMG)
            Vascular cell adhesion protein 1 (VCAM1) 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 Gamma-Glutamylvaline addition (2 hours)
                      Induced Change VCAM1 protein expression levels: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Peritonitis [ICD-11: DC50]
                      Details It is reported that gamma-glutamylvaline addition causes the decrease of VCAM1 protein expression compared with control group.
      Interleukin (IL)
            Interleukin-6 (IL6) 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 Gamma-Glutamylvaline addition (2 hours)
                      Induced Change IL6 protein expression levels: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Peritonitis [ICD-11: DC50]
                      Details It is reported that gamma-glutamylvaline addition causes the decrease of IL6 protein expression compared with control group.
            Interleukin-8 (IL8) 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 Gamma-Glutamylvaline addition (2 hours)
                      Induced Change CXCL8 protein expression levels: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Peritonitis [ICD-11: DC50]
                      Details It is reported that gamma-glutamylvaline addition causes the decrease of CXCL8 protein expression compared with control group.
      Selectin (SeT)
            E-selectin (SELE) 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 Gamma-Glutamylvaline addition (2 hours)
                      Induced Change SELE protein expression levels: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Peritonitis [ICD-11: DC50]
                      Details It is reported that gamma-glutamylvaline addition causes the decrease of SELE protein expression compared with control group.
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 [2]
                      Introduced Variation Knockdown (shRNA) of SULF1
                      Induced Change Gamma-Glutamylvaline concentration: decrease (FC = 0.52 / 0.64)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Ovarian cancer [ICD-11: 2C73]
                      Details It is reported that knockdown of SULF1 leads to the decrease of gamma-glutamylvaline 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 [3]
                      Introduced Variation Knockout of TP53
                      Induced Change Gamma-Glutamylvaline concentration: increase (Log2 FC=1.26)
                      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-glutamylvaline levels compared with control group.
References
1 Dietary -Glutamyl Valine Ameliorates TNF--Induced Vascular Inflammation via Endothelial Calcium-Sensing Receptors. J Agric Food Chem. 2020 Aug 26;68(34):9139-9149.
2 Erratum to: Loss of HSulf-1 promotes altered lipid metabolism in ovarian cancer. Cancer Metab. 2014 Nov 4;2:24.
3 Integrative omics analysis of p53-dependent regulation of metabolism. FEBS Lett. 2018 Feb;592(3):380-393.

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