S-D-Lactoylglutathione (YMDB00880)

Identification
YMDB IDYMDB00880
NameS-D-Lactoylglutathione
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionS-Lactoylglutathione is the product of reacting methylglyoxal with glutathione by the enzyme Glyoxalase I. The enzyme Glyoxalase II converts S-Lactoylglutathione into d-latic acid and glutathione. Methylglyoxal a glycolysis product that is toxic due to its high reactivity and thus the the glyoxalase system, made up of Glyoxalase I and Glyoxalase II is important in metabolising it. [PMID: 21310260]
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (4-Carboxyphenyl)chloromercury
  • (R)-S-lactoylglutathione
  • 4-Carboxyphenylmercuric chloride
  • 4-Chloromercuribenzoic acid
  • Benzoic acid, p-(chloromercuri)
  • D-lactoylglutathione
  • delta-lactoylglutathione
  • Mercurate(1-), (4-carboxylatophenyl)chloro-, hydrogen
  • Mercury, (4-carboxyphenyl)chloro-
  • Mercury, (p-carboxyphenyl)chloro-
  • p-(Chloromercuri)benzoic acid
  • p-Carboxyphenylmercuric chloride
  • p-Chlormercuribenzoic acid
  • p-Chloromercuric benzoic acid
  • p-Chloromercurybenzoic acid
  • PCMB
  • S-D-lactoyl-glutathione
  • S-delta-lactoyl-glutathione
  • S-delta-lactoylglutathione
  • S-lactate glutathione
  • S-lactateglutathione
  • S-lactoyl-glutathione
  • S-lactylglutathione
  • Usaf d-3
  • S-D-Lactoylglutathione
  • 2-amino-3-({[(2R)-2-hydroxypropanoyl]sulfanyl}methyl)butanedioate
  • 2-amino-3-({[(2R)-2-hydroxypropanoyl]sulphanyl}methyl)butanedioate
  • 2-amino-3-({[(2R)-2-hydroxypropanoyl]sulphanyl}methyl)butanedioic acid
CAS number59-85-8
WeightAverage: 251.257
Monoisotopic: 251.046357843
InChI KeyDWPTUFGRYYIXHG-JYMNUSQCSA-N
InChIInChI=1S/C8H13NO6S/c1-3(10)8(15)16-2-4(6(11)12)5(9)7(13)14/h3-5,10H,2,9H2,1H3,(H,11,12)(H,13,14)/t3-,4?,5?/m1/s1
IUPAC Name2-amino-3-({[(2R)-2-hydroxypropanoyl]sulfanyl}methyl)butanedioic acid
Traditional IUPAC Name2-amino-3-({[(2R)-2-hydroxypropanoyl]sulfanyl}methyl)butanedioic acid
Chemical FormulaC8H13NO6S
SMILES[H][C@](C)(O)C(=O)SCC(C(N)C(O)=O)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Branched fatty acid
  • Hydroxy fatty acid
  • Thia fatty acid
  • Dicarboxylic acid or derivatives
  • Fatty acid
  • Fatty acyl
  • Amino acid
  • Carbothioic s-ester
  • Thiocarboxylic acid ester
  • Secondary alcohol
  • Sulfenyl compound
  • Thiocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organopnictogen compound
  • Alcohol
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility14.7 g/LALOGPS
logP-2.9ALOGPS
logP-3.4ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)1.63ChemAxon
pKa (Strongest Basic)9.64ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area137.92 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity54.57 m³·mol⁻¹ChemAxon
Polarizability23.32 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB Pathways
Pyruvate metabolismPW002447 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Pyruvate metabolismec00620 Map00620
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dm-9310000000-d9aec94e9f3538320b5dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pc0-0970000000-d2c2a69bd5d6f6a4ff5eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-7930000000-ae9d21e38c3e84bfac90JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-1900000000-cf37b4735e36252013c4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1930000000-896585d5b044aa8ee7e3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03l0-2920000000-0d461f8185f193493814JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9300000000-85e14c7d7cc91df2f5e6JSpectraViewer
References
References:
  • 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
  • Martins, A. M., Mendes, P., Cordeiro, C., Freire, A. P. (2001). "In situ kinetic analysis of glyoxalase I and glyoxalase II in Saccharomyces cerevisiae." Eur J Biochem 268:3930-3936.11453985
  • Inoue, Y., Maeta, K., Nomura, W. (2011). "Glyoxalase system in yeasts: structure, function, and physiology." Semin Cell Dev Biol 22:278-284.21310260
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID741887
HMDB IDHMDB01066
Pubchem Compound ID119450
Kegg IDC03451
ChemSpider ID25032060
FOODB IDNot Available
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. 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.