You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:48 UTC
HMDB IDHMDB01066
Secondary Accession NumbersNone
Metabolite Identification
Common NameS-Lactoylglutathione
DescriptionS-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 (PMID: 8632674 ). S-lactoylglutathione has also been shown to modulate microtubule assembly (PMID: 690442 ).
Structure
Thumb
Synonyms
ValueSource
S-D-LactoylglutathioneChEBI
S-LactoylglutathioneChEBI
D-LactoylglutathioneHMDB
delta-LactoylglutathioneHMDB
N-(N-L-gamma-Glutamyl-S-(2-hydroxy-1-oxopropyl)-L-cysteinyl)-glycineHMDB
S-D-Lactoyl-glutathioneHMDB
S-delta-Lactoyl-glutathioneHMDB
S-delta-LactoylglutathioneHMDB
S-Lactate glutathioneHMDB
S-LactateglutathioneHMDB
S-Lactoyl-glutathioneHMDB
S-LactylglutathioneHMDB
S-[(2R)-2-Hydroxypropanoyl]-gamma-L-glutamyl-L-cysteinylglycineHMDB
Chemical FormulaC13H21N3O8S
Average Molecular Weight379.386
Monoisotopic Molecular Weight379.104935353
IUPAC Name(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-{[(2R)-2-hydroxypropanoyl]sulfanyl}ethyl]carbamoyl}butanoic acid
Traditional NameS-lactoylglutathione
CAS Registry Number25138-66-3
SMILES
C[C@@H](O)C(=O)SC[C@H](NC(=O)CC[C@H](N)C(O)=O)C(=O)NCC(O)=O
InChI Identifier
InChI=1S/C13H21N3O8S/c1-6(17)13(24)25-5-8(11(21)15-4-10(19)20)16-9(18)3-2-7(14)12(22)23/h6-8,17H,2-5,14H2,1H3,(H,15,21)(H,16,18)(H,19,20)(H,22,23)/t6-,7+,8+/m1/s1
InChI KeyInChIKey=VDYDCVUWILIYQF-CSMHCCOUSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as gamma-glutamyl peptides. These are oligo- and polypeptides consisting of any C-terminal alpha peptide 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 peptides
Alternative Parents
Substituents
  • Gamma-glutamyl alpha peptide
  • S-acylglutathione
  • Hydroxy fatty acid
  • N-acyl-aliphatic-alpha amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Alpha-amino acid amide
  • L-alpha-amino acid
  • Alpha-amino acid or derivatives
  • N-substituted-alpha-amino acid
  • Alpha-amino acid
  • Amino fatty acid
  • Fatty acyl
  • Fatty acid
  • N-acyl-amine
  • Fatty amide
  • Dicarboxylic acid or derivatives
  • Thiocarboxylic acid ester
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Sulfenyl compound
  • Thioether
  • Thiocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
Biofunction
  • Component of Pyruvate metabolism
ApplicationNot Available
Cellular locations
  • Mitochondria
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 Solubility7.55 mg/mLALOGPS
logP-2.9ALOGPS
logP-5.4ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)1.74ChemAxon
pKa (Strongest Basic)9.31ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area196.12 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity84.78 m3·mol-1ChemAxon
Polarizability36.01 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-1149000000-62e5724126eead68b1ccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-003r-6494000000-e3b7d776638d1bad4552View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fba-3970000000-ead14f990fca59e626edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a70-0059000000-93c2a2c66ec470d5e065View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-5398000000-b0a25646cfd9bdbb68e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9200000000-d10281b62f65d09c7238View in MoNA
Biological Properties
Cellular Locations
  • Mitochondria
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Leigh SyndromeSMP00196Not Available
Primary hyperoxaluria II, PH2SMP00558Not Available
Pyruvaldehyde DegradationSMP00459Not Available
Pyruvate Decarboxylase E1 Component Deficiency (PDHE1 Deficiency)SMP00334Not Available
Pyruvate Dehydrogenase Complex DeficiencySMP00212Not Available
Pyruvate kinase deficiencySMP00559Not Available
Pyruvate MetabolismSMP00060map00620
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022405
KNApSAcK IDNot Available
Chemspider ID389032
KEGG Compound IDC03451
BioCyc IDS-LACTOYL-GLUTATHIONE
BiGG ID41876
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01066
Metagene LinkHMDB01066
METLIN ID5979
PubChem Compound440018
PDB IDNot Available
ChEBI ID15694
References
Synthesis ReferenceLiu, Yan; Hama, Hideki; Fujita, Yasuya; Kondo, Akihiko; Inoue, Yoshiharu; Kimura, Akira; Fu Production of S-lactoylglutathione by high activity whole cell biocatalysts prepared by permeabilization of recombinant Saccharomyces cerevisiae with alcohols.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Edwards LG, Adesida A, Thornalley PJ: Inhibition of human leukaemia 60 cell growth by S-D-lactoylglutathione in vitro. Mediation by metabolism to N-D-lactoylcysteine and induction of apoptosis. Leuk Res. 1996 Jan;20(1):17-26. [8632674 ]
  2. Thornalley PJ: Advances in glyoxalase research. Glyoxalase expression in malignancy, anti-proliferative effects of methylglyoxal, glyoxalase I inhibitor diesters and S-D-lactoylglutathione, and methylglyoxal-modified protein binding and endocytosis by the advanced glycation endproduct receptor. Crit Rev Oncol Hematol. 1995 Aug;20(1-2):99-128. [7576201 ]
  3. Irsch T, Krauth-Siegel RL: Glyoxalase II of African trypanosomes is trypanothione-dependent. J Biol Chem. 2004 May 21;279(21):22209-17. Epub 2004 Feb 19. [14976196 ]
  4. Gillespie E: Concanavalin A increases glyoxalase enzyme activities in polymorphonuclear leukocytes and lymphocytes. J Immunol. 1978 Sep;121(3):923-5. [690442 ]

Enzymes

General function:
Involved in lactoylglutathione lyase activity
Specific function:
Catalyzes the conversion of hemimercaptal, formed from methylglyoxal and glutathione, to S-lactoylglutathione. Involved in the regulation of TNF-induced transcriptional activity of NF-kappa-B.
Gene Name:
GLO1
Uniprot ID:
Q04760
Molecular weight:
20777.515
Reactions
S-Lactoylglutathione → Glutathione + Pyruvaldehydedetails
General function:
Involved in hydrolase activity
Specific function:
Thiolesterase that catalyzes the hydrolysis of S-D-lactoyl-glutathione to form glutathione and D-lactic acid.
Gene Name:
HAGH
Uniprot ID:
Q16775
Molecular weight:
28859.855
Reactions
S-Lactoylglutathione + Water → Glutathione + D-Lactic aciddetails
General function:
Involved in hydrolase activity
Specific function:
Hydrolase acting on ester bonds (Potential).
Gene Name:
HAGHL
Uniprot ID:
Q6PII5
Molecular weight:
Not Available
Reactions
S-Lactoylglutathione + Water → Glutathione + D-Lactic aciddetails