Showing Metabocard for (R)-S-lactoylglutathione (BASm0002730)

Common Name(r)-s-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
Molecular FormulaC13H21N3O8S
Average Mass379.38600
Monoisotopic Mass379.10494
IUPAC Name(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-{[(2R)-2-hydroxypropanoyl]sulfanyl}ethyl]carbamoyl}butanoic acid
Traditional Name(2s)-2-amino-4-{[(1r)-1-(carboxymethylcarbamoyl)-2-{[(2r)-2-hydroxypropanoyl]sulfanyl}ethyl]carbamoyl}butanoic acid
CAS Registry Number25138-66-3
SMILESC[C@@H](O)C(=O)SC[C@H](NC(=O)CC[C@H]([NH3+])C(=O)[O-])C(=O)NCC(=O)[O-]
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
CHEBI IDCHEBI:57474
HMDB IDHMDB0001066
Pathways
NameSMPDB/PathBank
Pyruvate metabolism
Leigh Syndrome
Pyruvate Dehydrogenase Complex Deficiency
Pyruvate Decarboxylase E1 Component Deficiency (PDHE1 Deficiency)
Pyruvaldehyde Degradation
Primary hyperoxaluria II, PH2
Pyruvate kinase deficiency
StateSolid
Water Solubility7.55e+00 g/l
logP-2.88
logS-1.70
pKa (Strongest Acidic)1.74
pKa (Strongest Basic)9.31
Hydrogen Acceptor Count9
Hydrogen Donor Count6
Polar Surface Area196.12 Ų
Rotatable Bond Count12
Physiological Charge-1
Formal Charge0
Refractivity84.78 m³·mol⁻¹
Polarizability36.01

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