MiMeDB: Showing metabocard for S-D-Lactoylglutathione (MMDBc0033173)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:37:41 UTC

Update Date

2024-04-20 06:12:53 UTC

Metabolite ID

MMDBc0033173

Metabolite Identification

Common Name

S-D-Lactoylglutathione

Description

S-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

MOL SDF PDB SMILES InChI


  Mrv0541 02241222392D          

 17 16  0  0  0  0            999 V2000
    4.5089   -5.2179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7956   -5.6308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2221   -5.6308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7956   -6.4567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2221   -3.1533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5089   -4.3837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2221   -3.9791    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.0782   -5.2179    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9353   -5.2179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5089   -6.8696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2221   -6.4567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0782   -6.8696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5089   -2.7403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9353   -2.7403    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9353   -1.9145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5234   -2.1522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6486   -3.1533    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  7  1  0  0  0  0
  6  1  1  0  0  0  0
  7  6  1  0  0  0  0
  8  2  1  0  0  0  0
  9  3  1  0  0  0  0
 10  4  1  0  0  0  0
 11  3  2  0  0  0  0
 12  4  2  0  0  0  0
 13  5  2  0  0  0  0
 14  5  1  0  0  0  0
 15 14  1  0  0  0  0
 14 16  1  6  0  0  0
 14 17  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033173

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@](C)(O)C(=O)SCC(C(N)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H13NO6S/c1-3(10)8(15)16-2-4(6(11)12)5(9)7(13)14/h3-5,10H,2,9H2,1H3,(H,11,12)(H,13,14)/t3-,4?,5?/m1/s1

> <INCHI_KEY>
DWPTUFGRYYIXHG-JYMNUSQCSA-N

> <FORMULA>
C8H13NO6S

> <MOLECULAR_WEIGHT>
251.257

> <EXACT_MASS>
251.046357843

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
23.32421489389216

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-3-({[(2R)-2-hydroxypropanoyl]sulfanyl}methyl)butanedioic acid

> <ALOGPS_LOGP>
-2.89

> <JCHEM_LOGP>
-3.3977314131665834

> <ALOGPS_LOGS>
-1.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.880967204059422

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.6307252297098263

> <JCHEM_PKA_STRONGEST_BASIC>
9.643209735683243

> <JCHEM_POLAR_SURFACE_AREA>
137.92

> <JCHEM_REFRACTIVITY>
54.574400000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.47e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-3-({[(2R)-2-hydroxypropanoyl]sulfanyl}methyl)butanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       8.417  -9.740   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.085 -10.511   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.748 -10.511   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.085 -12.053   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.748  -5.886   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.417  -8.183   0.000  0.00  0.00           C+0
HETATM    7  S   UNK     0       9.748  -7.428   0.000  0.00  0.00           S+0
HETATM    8  N   UNK     0       5.746  -9.740   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0      11.079  -9.740   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       8.417 -12.823   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       9.748 -12.053   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       5.746 -12.823   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       8.417  -5.115   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      11.079  -5.115   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      11.079  -3.574   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      12.177  -4.017   0.000  0.00  0.00           C+0
HETATM   17  H   UNK     0      12.411  -5.886   0.000  0.00  0.00           H+0
CONECT    1    2    3    6                                                  
CONECT    2    1    4    8                                                  
CONECT    3    1    9   11                                                  
CONECT    4    2   10   12                                                  
CONECT    5    7   13   14                                                  
CONECT    6    1    7                                                       
CONECT    7    5    6                                                       
CONECT    8    2                                                            
CONECT    9    3                                                            
CONECT   10    4                                                            
CONECT   11    3                                                            
CONECT   12    4                                                            
CONECT   13    5                                                            
CONECT   14    5   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

Synonyms

Value	Source
S-D-Lactoylglutathione	ChEMBL
2-amino-3-({[(2R)-2-hydroxypropanoyl]sulfanyl}methyl)butanedioate	Generator
2-amino-3-({[(2R)-2-hydroxypropanoyl]sulphanyl}methyl)butanedioate	Generator
2-amino-3-({[(2R)-2-hydroxypropanoyl]sulphanyl}methyl)butanedioic acid	Generator

Molecular Formula

C₈H₁₃NO₆S

Average Mass

251.257

Monoisotopic Mass

251.046357843

IUPAC Name

2-amino-3-({[(2R)-2-hydroxypropanoyl]sulfanyl}methyl)butanedioic acid

Traditional Name

2-amino-3-({[(2R)-2-hydroxypropanoyl]sulfanyl}methyl)butanedioic acid

CAS Registry Number

59-85-8

SMILES

[H][C@](C)(O)C(=O)SCC(C(N)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C8H13NO6S/c1-3(10)8(15)16-2-4(6(11)12)5(9)7(13)14/h3-5,10H,2,9H2,1H3,(H,11,12)(H,13,14)/t3-,4?,5?/m1/s1

InChI Key

DWPTUFGRYYIXHG-JYMNUSQCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids

Alternative Parents

Substituents

Alpha-amino acid
Branched fatty acid
Hydroxy fatty acid
Thia fatty acid
Dicarboxylic acid or derivatives
Fatty acid
Fatty acyl
Amino acid
Carbothioic s-ester
Thiocarboxylic acid ester
Secondary alcohol
Sulfenyl compound
Thiocarboxylic acid or derivatives
Carboxylic acid
Hydrocarbon derivative
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organopnictogen compound
Alcohol
Organic oxide
Carbonyl group
Organic oxygen compound
Amine
Organic nitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	14.7 g/L	ALOGPS
logP	-2.9	ALOGPS
logP	-3.4	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	1.63	ChemAxon
pKa (Strongest Basic)	9.64	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	137.92 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	54.57 m³·mol⁻¹	ChemAxon
Polarizability	23.32 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dm-9310000000-d9aec94e9f3538320b5d	2016-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0pc0-0970000000-d2c2a69bd5d6f6a4ff5e	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05fr-7930000000-ae9d21e38c3e84bfac90	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ue9-1900000000-cf37b4735e36252013c4	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-1930000000-896585d5b044aa8ee7e3	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03l0-2920000000-0d461f8185f193493814	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9300000000-85e14c7d7cc91df2f5e6	2016-09-12	View Spectrum

Biological Properties

Cellular Locations

Mitochondria

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44308724

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Gillespie E: Concanavalin A increases glyoxalase enzyme activities in polymorphonuclear leukocytes and lymphocytes. J Immunol. 1978 Sep;121(3):923-5. [PubMed:690442 ]
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. doi: 10.1016/1040-8428(94)00149-n. [PubMed:7576201 ]
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. doi: 10.1016/0145-2126(95)00095-x. [PubMed:8632674 ]
Irsch T, Krauth-Siegel RL: Glyoxalase II of African trypanosomes is trypanothione-dependent. J Biol Chem. 2004 May 21;279(21):22209-17. doi: 10.1074/jbc.M401240200. Epub 2004 Feb 19. [PubMed:14976196 ]

Showing metabocard for S-D-Lactoylglutathione (MMDBc0033173)

MOL for #<Metabolite:0x00007f46d8243620>

3D MOL for #<Metabolite:0x00007f46d8243620>

3D SDF for #<Metabolite:0x00007f46d8243620>

3D-SDF for #<Metabolite:0x00007f46d8243620>

PDB for #<Metabolite:0x00007f46d8243620>

3D PDB for #<Metabolite:0x00007f46d8243620>

SMILES for #<Metabolite:0x00007f46d8243620>

INCHI for #<Metabolite:0x00007f46d8243620>

Structure for #<Metabolite:0x00007f46d8243620>

3D Structure for #<Metabolite:0x00007f46d8243620>