Details of Metabolite

General Information of MET (ID: META00367)
Name S-Lactoylglutathione
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(R)-S-Lactoylglutathione; D-Lactoylglutathione; N-(N-L-gamma-Glutamyl-S-(2-hydroxy-1-oxopropyl)-L-cysteinyl)-glycine; S-D-Lactoyl-glutathione; S-D-Lactoylglutathione; S-Lactate glutathione; S-Lactateglutathione; S-Lactoyl-glutathione; S-Lactylglutathione; S-[(2R)-2-Hydroxypropanoyl]-gamma-L-glutamyl-L-cysteinylglycine; S-delta-Lactoyl-glutathione; S-delta-Lactoylglutathione; delta-Lactoylglutathione
Source Endogenous;Escherichia Coli Metabolite;Yeast Metabolite;Food;Microbial
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
440018
HMDB ID
HMDB0001066
Formula
C13H21N3O8S
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=440018"></iframe>
3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C03451
ChEBI ID
15694
FooDB ID
FDB022405
ChemSpider ID
389032
METLIN ID
5979
Physicochemical Properties Molecular Weight 379.39 Topological Polar Surface Area 221
XlogP -4.6 Complexity 527
Heavy Atom Count 25 Rotatable Bond Count 12
Hydrogen Bond Donor Count 6 Hydrogen Bond Acceptor Count 10
Function
S-Lactoylglutathione is a substrate of lactoylglutathione lyase [EC 4.4.1.5] in pyruvate metabolism (KEGG). Another enzyme, glyoxalase I, synthesizes this compound by converting methylglyoxal and reduced glutathione to S-lactoylglutathione. S-D-lactoylglutathione can be hydrolysed by thiolesterases to reduced glutathione and D-lactate but also converted to N-D-lactoylcysteinylglycine and N-D-lactoylcysteine by gamma-glutamyl transferase and dipeptidase. S-lactoylglutathione has also been shown to modulate microtubule assembly.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Hydrolases (EC 3)
            GTPase KRas (KRAS) 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 Overexpression of KRAS
                      Induced Change S-Lactoylglutathione concentration: decrease (FC = 0.26)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Lung cancer [ICD-11: 2C25]
                      Details It is reported that overexpression of KRAS leads to the decrease of s-lactoylglutathione levels compared with control group.
      Lyases (EC 4)
            Cystathionine gamma-lyase (CTH) 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 Cth
                      Induced Change S-Lactoylglutathione concentration: increase (FC = 3.89)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Organic acid disorderss [ICD-11: 5C50]
                      Details It is reported that knockout of Cth leads to the increase of s-lactoylglutathione 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 S-Lactoylglutathione concentration: increase (Log2 FC=1.55)
                      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 s-lactoylglutathione levels compared with control group.
References
1 Capturing the metabolomic diversity of KRAS mutants in non-small-cell lung cancer cells. Oncotarget. 2014 Jul 15;5(13):4722-31.
2 Hydrogen Sulfide Is a Regulator of Hemoglobin Oxygen-Carrying Capacity via Controlling 2,3-BPG Production in Erythrocytes. Oxid Med Cell Longev. 2021 Feb 13;2021:8877691.
3 Integrative omics analysis of p53-dependent regulation of metabolism. FEBS Lett. 2018 Feb;592(3):380-393.

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