Record Information
Version1.0
Creation date2011-09-21 00:13:30 UTC
Update date2019-11-27 17:42:36 UTC
Primary IDFDB022405
Secondary Accession Numbers
  • FDB031155
Chemical Information
FooDB 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). [HMDB]. S-Lactoylglutathione is found in many foods, some of which are blackcurrant, oat, pomegranate, and brussel sprouts.
CAS Number25138-66-3
Structure
Thumb
Synonyms
SynonymSource
S-D-LactoylglutathioneChEBI
(R)-S-LactoylglutathioneHMDB
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
(R)-S-lactoylglutathionehmdb
D-lactoylglutathionehmdb
delta-lactoylglutathionehmdb
n-(n-l-gamma-glutamyl-S-(2-hydroxy-1-oxopropyl)-l-cysteinyl)-glycinehmdb
S-[(2R)-2-hydroxypropanoyl]-gamma-L-glutamyl-L-cysteinylglycinehmdb
S-D-lactoyl-glutathionehmdb
S-D-lactoylglutathionehmdb
S-delta-lactoyl-glutathionehmdb
S-delta-lactoylglutathionehmdb
S-lactate glutathionehmdb
S-lactateglutathionehmdb
S-lactoyl-glutathionehmdb
S-lactylglutathionehmdb
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
Chemical FormulaC13H21N3O8S
IUPAC name(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-{[(2R)-2-hydroxypropanoyl]sulfanyl}ethyl]carbamoyl}butanoic acid
InChI IdentifierInChI=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 KeyVDYDCVUWILIYQF-CSMHCCOUSA-N
Isomeric SMILESC[C@@H](O)C(=O)SC[C@H](NC(=O)CC[C@H](N)C(O)=O)C(=O)NCC(O)=O
Average Molecular Weight379.386
Monoisotopic Molecular Weight379.104935353
Classification
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
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-022d-9025000000-e8442b76e42e68182070View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0f8c-6700390000-be9c9075535b7b68d56cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0109000000-a34d20761c4d6bee6ff4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-05dj-0769000000-125dd04c3309557ca71dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-02f1-2930000000-bab00ec3c9a62c353d98View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004l-2900000000-ed3b919674c5534985e4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-005c-9800000000-c037ad2006918e401b23View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-1935000000-5775999bbe10e3b4c9dbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0019000000-99436ad12d519791de4eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001j-3693000000-a466eff4cff41d7086c7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0032-1930000000-18d451bef69e367a6364View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-003s-8900000000-15e831c7f610fbcdf31cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-003r-9300000000-c6405af72f8eaaf2cb11View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-001i-0290000000-ef71ecf2559bf8a8090dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-9873000000-760e0e4073de1137832eView in MoNA
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
ChemSpider ID389032
ChEMBL IDNot Available
KEGG Compound IDC03451
Pubchem Compound ID440018
Pubchem Substance IDNot Available
ChEBI ID15694
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01066
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID41876
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
Pathways
NameSMPDB LinkKEGG Link
Pyruvaldehyde DegradationSMP00459 Not Available
Pyruvate MetabolismSMP00060 map00620
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference