Showing Compound Card for S-Lactoylglutathione (CDB004880)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (3) Show 7 proteinsXML
Record Information
Version1.0
Created at2020-04-17 18:46:21 UTC
Updated at2020-11-18 16:38:55 UTC
CannabisDB IDCDB004880
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameS-Lactoylglutathione
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. Within humans, S-lactoylglutathione participates in a number of enzymatic reactions. In particular, S-lactoylglutathione can be converted into glutathione and D-lactic acid; which is mediated by the enzyme hydroxyacylglutathione hydrolase, mitochondrial. In addition, S-lactoylglutathione can be converted into glutathione and pyruvaldehyde through the action of the enzyme lactoylglutathione lyase. In humans, S-lactoylglutathione is involved in pyruvate metabolism. Outside of the human body, S-Lactoylglutathione has been detected, but not quantified in, several different foods, such as sweet potato, pistachio, guava, welsh onions, and german camomiles. This could make S-lactoylglutathione a potential biomarker for the consumption of these foods. The S- derivative of glutathione. S-Lactoylglutathione is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
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
Chemical FormulaC13H21N3O8S
Average Molecular Weight379.39
Monoisotopic Molecular Weight379.1049
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 KeyVDYDCVUWILIYQF-CSMHCCOUSA-N
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSS-Lactoylglutathione, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-022d-9025000000-e8442b76e42e68182070Spectrum
Predicted GC-MSS-Lactoylglutathione, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0f8c-6700390000-be9c9075535b7b68d56cSpectrum
Predicted GC-MSS-Lactoylglutathione, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0109000000-a34d20761c4d6bee6ff42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-05dj-0769000000-125dd04c3309557ca71d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-02f1-2930000000-bab00ec3c9a62c353d982017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004l-2900000000-ed3b919674c5534985e42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-005c-9800000000-c037ad2006918e401b232017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-1935000000-5775999bbe10e3b4c9db2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0019000000-99436ad12d519791de4e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001j-3693000000-a466eff4cff41d7086c72017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0032-1930000000-18d451bef69e367a63642017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-003s-8900000000-15e831c7f610fbcdf31c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-003r-9300000000-c6405af72f8eaaf2cb112017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-001i-0290000000-ef71ecf2559bf8a8090d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-9873000000-760e0e4073de1137832e2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-1149000000-62e5724126eead68b1cc2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-003r-6494000000-e3b7d776638d1bad45522015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fba-3970000000-ead14f990fca59e626ed2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a70-0059000000-93c2a2c66ec470d5e0652015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-5398000000-b0a25646cfd9bdbb68e12015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9200000000-d10281b62f65d09c72382015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0019000000-738e521a28b7b76a51172021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08ml-0960000000-6303aeec8244b3481bcd2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-4910000000-35e994483e5244ab56422021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0019000000-a681d82646af48a3b5922021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000t-4965000000-c35d5adc9f5c770c37062021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03gi-1950000000-cb8ea7b94c227704fc5a2021-09-24View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Lactoylglutathione lyaseGLO16p21.3-p21.1Q04760 details
Hydroxyacylglutathione hydrolase, mitochondrialHAGH16p13.3Q16775 details
Hydroxyacylglutathione hydrolase-like proteinHAGHLQ6PII5 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Lactoylglutathione lyaseGLO16p21.3-p21.1Q04760 details
Hydroxyacylglutathione hydrolase, mitochondrialHAGH16p13.3Q16775 details
Hydroxyacylglutathione hydrolase-like proteinHAGHLQ6PII5 details
ReceptorsNot Available
Transcriptional Factors
Protein NameGene NameLocusUniprot IDDetails
Lactoylglutathione lyaseGLO16p21.3-p21.1Q04760 details
Concentrations Data
Not Available
HMDB IDHMDB0001066
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022405
KNApSAcK IDC00019550
Chemspider ID389032
KEGG Compound IDC03451
BioCyc IDS-LACTOYL-GLUTATHIONE
BiGG ID41876
Wikipedia LinkNot Available
METLIN ID5979
PubChem Compound440018
PDB IDNot Available
ChEBI ID15694
References
General ReferencesNot Available

Enzymes

Enzyme Details
1. Lactoylglutathione lyase
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
Enzyme 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:
HAGH
Uniprot ID:
Q16775
Molecular weight:
28859.855
Enzyme Details
3. Hydroxyacylglutathione hydrolase-like protein
General function:
Involved in hydrolase activity
Specific function:
Hydrolase acting on ester bonds (Potential).
Gene Name:
HAGHL
Uniprot ID:
Q6PII5
Molecular weight:
Not Available