Human Metabolome Database: Showing metabocard for S-Lactoylglutathione (HMDB0001066)

You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.

Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3) Show 3 proteins XML

enzymes (3) Show 3 proteins

Record Information

Version

4.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2020-03-13 16:34:28 UTC

HMDB ID

HMDB0001066

Secondary Accession Numbers

HMDB01066

Metabolite Identification

Common Name

S-Lactoylglutathione

Description

S-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.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
S-D-Lactoylglutathione	ChEBI
(R)-S-Lactoylglutathione	HMDB
D-Lactoylglutathione	HMDB
delta-Lactoylglutathione	HMDB
N-(N-L-gamma-Glutamyl-S-(2-hydroxy-1-oxopropyl)-L-cysteinyl)-glycine	HMDB
S-D-Lactoyl-glutathione	HMDB
S-delta-Lactoyl-glutathione	HMDB
S-delta-Lactoylglutathione	HMDB
S-Lactate glutathione	HMDB
S-Lactateglutathione	HMDB
S-Lactoyl-glutathione	HMDB
S-Lactylglutathione	HMDB
S-[(2R)-2-Hydroxypropanoyl]-gamma-L-glutamyl-L-cysteinylglycine	HMDB

Chemical Formula

C₁₃H₂₁N₃O₈S

Average Molecular Weight

379.386

Monoisotopic Molecular Weight

379.104935353

IUPAC Name

(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-{[(2R)-2-hydroxypropanoyl]sulfanyl}ethyl]carbamoyl}butanoic acid

Traditional Name

S-lactoylglutathione

CAS Registry Number

25138-66-3

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 Key

VDYDCVUWILIYQF-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

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 Framework

Aliphatic acyclic compounds

External Descriptors

glutathione derivative (CHEBI:15694 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Animal

Biological location:

Subcellular:

Mitochondria

Process

Naturally occurring process:

Biological process:

Biochemical pathway:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	7.55 g/L	ALOGPS
logP	-2.9	ALOGPS
logP	-5.4	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	1.74	ChemAxon
pKa (Strongest Basic)	9.31	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	196.12 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	84.78 m³·mol⁻¹	ChemAxon
Polarizability	36.01 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-022d-9025000000-e8442b76e42e68182070	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0f8c-6700390000-be9c9075535b7b68d56c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-0109000000-a34d20761c4d6bee6ff4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-05dj-0769000000-125dd04c3309557ca71d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-02f1-2930000000-bab00ec3c9a62c353d98	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004l-2900000000-ed3b919674c5534985e4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-005c-9800000000-c037ad2006918e401b23	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-004i-1935000000-5775999bbe10e3b4c9db	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-0019000000-99436ad12d519791de4e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001j-3693000000-a466eff4cff41d7086c7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0032-1930000000-18d451bef69e367a6364	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-003s-8900000000-15e831c7f610fbcdf31c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-003r-9300000000-c6405af72f8eaaf2cb11	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-001i-0290000000-ef71ecf2559bf8a8090d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-001i-9873000000-760e0e4073de1137832e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01q9-1149000000-62e5724126eead68b1cc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-003r-6494000000-e3b7d776638d1bad4552	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fba-3970000000-ead14f990fca59e626ed	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a70-0059000000-93c2a2c66ec470d5e065	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-5398000000-b0a25646cfd9bdbb68e1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9200000000-d10281b62f65d09c7238	Spectrum

Biological Properties

Cellular Locations

Mitochondria

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/Pathwhiz	KEGG
Pyruvate Metabolism
Pyruvaldehyde Degradation		Not Available
Leigh Syndrome		Not Available
Pyruvate Decarboxylase E1 Component Deficiency (PDHE1 Deficiency)		Not Available
Pyruvate Dehydrogenase Complex Deficiency		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

S-LACTOYL-GLUTATHIONE

BiGG ID

41876

Wikipedia Link

Not Available

METLIN ID

5979

PubChem Compound

440018

PDB ID

Not Available

ChEBI ID

15694

Food Biomarker Ontology

Not Available

VMH ID

LGT_S

References

Synthesis Reference

Liu, Yan; Hama, Hideki; Fujita, Yasuya; Kondo, Akihiko; Inoue, Yoshiharu; Kimura, Akira; Fukuda H. Production of S-lactoylglutathione by high activity whole cell biocatalysts prepared by permeabilization of recombinant Saccharomyces cerevisiae with alcohols. Biotechnol Bioeng. 1999 Jul 5;64(1):54-60.

Material Safety Data Sheet (MSDS)

Not Available

General References

Edwards LG, Adesida A, Thornalley PJ: Inhibition of human leukaemia 60 cell growth by S-D-lactoylglutathione in vitro. Mediation by metabolism to N-D-lactoylcysteine and induction of apoptosis. Leuk Res. 1996 Jan;20(1):17-26. [PubMed:8632674 ]
Thornalley PJ: Advances in glyoxalase research. Glyoxalase expression in malignancy, anti-proliferative effects of methylglyoxal, glyoxalase I inhibitor diesters and S-D-lactoylglutathione, and methylglyoxal-modified protein binding and endocytosis by the advanced glycation endproduct receptor. Crit Rev Oncol Hematol. 1995 Aug;20(1-2):99-128. [PubMed:7576201 ]
Irsch T, Krauth-Siegel RL: Glyoxalase II of African trypanosomes is trypanothione-dependent. J Biol Chem. 2004 May 21;279(21):22209-17. Epub 2004 Feb 19. [PubMed:14976196 ]
Gillespie E: Concanavalin A increases glyoxalase enzyme activities in polymorphonuclear leukocytes and lymphocytes. J Immunol. 1978 Sep;121(3):923-5. [PubMed:690442 ]

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

Reactions

S-Lactoylglutathione → Glutathione + Pyruvaldehyde	details

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

Reactions

S-Lactoylglutathione + Water → Glutathione + D-Lactic acid	details

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

Reactions

S-Lactoylglutathione + Water → Glutathione + D-Lactic acid	details

Showing metabocard for S-Lactoylglutathione (HMDB0001066)

Structure for HMDB0001066 (S-Lactoylglutathione)

Enzymes

Reactions

Reactions

Reactions