Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-17 23:31:38 UTC
Update Date2024-04-30 19:37:34 UTC
Metabolite IDMMDBc0029542
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
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
Molecular FormulaC13H21N3O8S
Average Mass379.386
Monoisotopic Mass379.104935353
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 KeyVDYDCVUWILIYQF-CSMHCCOUSA-N