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S-Lactoylglutathione (YMDB00246)

Identification
YMDB IDYMDB00246
NameS-Lactoylglutathione
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionS-Lactoylglutathione belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. S-Lactoylglutathione is a very strong basic compound (based on its pKa). S-Lactoylglutathione exists in all living species, ranging from bacteria to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (R)-S-lactoylglutathione
  • D-lactoylglutathione
  • delta-lactoylglutathione
  • n-(n-l-gamma-glutamyl-S-(2-hydroxy-1-oxopropyl)-l-cysteinyl)-glycine
  • S-[(2R)-2-hydroxypropanoyl]-gamma-L-glutamyl-L-cysteinylglycine
  • S-D-lactoyl-glutathione
  • S-D-lactoylglutathione
  • S-delta-lactoyl-glutathione
  • S-delta-lactoylglutathione
  • S-lactate glutathione
  • S-lactateglutathione
  • S-lactoyl-glutathione
  • S-lactylglutathione
CAS number25138-66-3
WeightAverage: 379.386
Monoisotopic: 379.104935353
InChI KeyVDYDCVUWILIYQF-CSMHCCOUSA-N
InChIInChI=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
IUPAC Name(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-{[(2R)-2-hydroxypropanoyl]sulfanyl}ethyl]carbamoyl}butanoic acid
Traditional IUPAC NameS-lactoylglutathione
Chemical FormulaC13H21N3O8S
SMILES[H]OC(=O)C([H])([H])N([H])C(=O)[C@@]([H])(N([H])C(=O)C([H])([H])C([H])([H])[C@]([H])(N([H])[H])C(=O)O[H])C([H])([H])SC(=O)[C@]([H])(O[H])C([H])([H])[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentOligopeptides
Alternative Parents
Substituents
  • Alpha-oligopeptide
  • Gamma-glutamyl alpha peptide
  • S-(2-hydroxyacyl)glutathione
  • S-acylglutathione
  • Glutamine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Alpha-amino acid amide
  • Cysteine or derivatives
  • Alpha-amino acid
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • N-acyl-amine
  • Fatty acyl
  • Fatty amide
  • Dicarboxylic acid or derivatives
  • Fatty acid
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Amino acid or derivatives
  • Thiocarboxylic acid ester
  • Amino acid
  • Carboxamide group
  • Carbothioic s-ester
  • Sulfenyl compound
  • Carboxylic acid
  • Thiocarboxylic acid or derivatives
  • Organosulfur compound
  • Primary amine
  • Organic nitrogen compound
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Amine
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary aliphatic amine
  • Organooxygen compound
  • Organonitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility7.55 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity84.78 m³·mol⁻¹ChemAxon
Polarizability36.01 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • mitochondrion
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Pyruvate metabolismPW002447 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Pyruvate metabolismec00620 Map00620
SMPDB Reactions
Glutathione + Pyruvaldehyde ↔ S-Lactoylglutathione
S-Lactoylglutathione + water ↔ Glutathione + D-Lactic acid
KEGG Reactions
S-Lactoylglutathione + water → Glutathione + hydron + D-Lactic acid
Pyruvaldehyde + Glutathione → S-Lactoylglutathione
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-022d-9025000000-e8442b76e42e68182070JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0f8c-6700390000-be9c9075535b7b68d56cJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0109000000-a34d20761c4d6bee6ff4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-05dj-0769000000-125dd04c3309557ca71dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-02f1-2930000000-bab00ec3c9a62c353d98JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004l-2900000000-ed3b919674c5534985e4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-005c-9800000000-c037ad2006918e401b23JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-1935000000-5775999bbe10e3b4c9dbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0019000000-99436ad12d519791de4eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001j-3693000000-a466eff4cff41d7086c7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0032-1930000000-18d451bef69e367a6364JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-003s-8900000000-15e831c7f610fbcdf31cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-003r-9300000000-c6405af72f8eaaf2cb11JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-001i-0290000000-ef71ecf2559bf8a8090dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-9873000000-760e0e4073de1137832eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-1149000000-62e5724126eead68b1ccJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-003r-6494000000-e3b7d776638d1bad4552JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fba-3970000000-ead14f990fca59e626edJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a70-0059000000-93c2a2c66ec470d5e065JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-5398000000-b0a25646cfd9bdbb68e1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9200000000-d10281b62f65d09c7238JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0019000000-738e521a28b7b76a5117JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08ml-0960000000-6303aeec8244b3481bcdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-4910000000-35e994483e5244ab5642JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0019000000-a681d82646af48a3b592JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000t-4965000000-c35d5adc9f5c770c3706JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03gi-1950000000-cb8ea7b94c227704fc5aJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Inoue, Y., Watanabe, K., Shimosaka, M., Saikusa, T., Fukuda, Y., Murata, K., Kimura, A. (1985). "Metabolism of 2-oxoaldehydes in yeasts. Purification and characterization of lactaldehyde dehydrogenase from Saccharomyces cerevisiae." Eur J Biochem 153:243-247.3908097
  • Penninckx, M. J., Jaspers, C. J., Legrain, M. J. (1983). "The glutathione-dependent glyoxalase pathway in the yeast Saccharomyces cerevisiae." J Biol Chem 258:6030-6036.6343368
Synthesis Reference:Liu, 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.
External Links:
ResourceLink
CHEBI ID15694
HMDB IDHMDB01066
Pubchem Compound ID119450
Kegg IDC03451
ChemSpider ID389032
FOODB IDFDB022405
Wikipedia IDNot Available
BioCyc IDS-LACTOYL-GLUTATHIONE

Enzymes

Protein Details
1. Hydroxyacylglutathione hydrolase, cytoplasmic isozyme
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:
GLO2
Uniprot ID:
Q05584
Molecular weight:
31326.30078
Reactions
S-(2-hydroxyacyl)glutathione + H(2)O → glutathione + a 2-hydroxy carboxylate.
Protein Details
2. Lactoylglutathione lyase
General function:
Involved in lactoylglutathione lyase activity
Specific function:
Catalyzes the conversion of hemimercaptal, formed from methylglyoxal and glutathione, to S-lactoylglutathione
Gene Name:
GLO1
Uniprot ID:
P50107
Molecular weight:
37208.69922
Reactions
(R)-S-lactoylglutathione → glutathione + methylglyoxal.
Protein Details
3. Hydroxyacylglutathione hydrolase, mitochondrial
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:
GLO4
Uniprot ID:
Q12320
Molecular weight:
32338.59961
Reactions
S-(2-hydroxyacyl)glutathione + H(2)O → glutathione + a 2-hydroxy carboxylate.