MiMeDB: Showing metabocard for S-Lactoylglutathione (MMDBc0029542)

Plant

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:31:38 UTC

Update Date

2022-08-31 13:42:59 UTC

Metabolite ID

MMDBc0029542

Metabolite Identification

Common Name

S-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 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0001066
     RDKit          3D
S-Lactoylglutathione
 46 45  0  0  0  0  0  0  0  0999 V2000
   -5.1401   -2.7183   -0.9714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1777   -2.1398    0.4267 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7015   -3.0347    1.3452 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8264   -1.7031    0.8602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3826   -2.1568    1.8980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8508   -0.5565   -0.0731 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2839   -0.2753    0.7608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3642    0.6894    0.0550 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8388    0.7671    0.8876 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1002    0.3102    0.4212 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1788   -0.1736   -0.7409 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3105    0.3803    1.2390 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5498   -0.1557    0.6302 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5097   -1.6190    0.2558 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2602   -2.4588    1.4097 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559   -1.9471   -0.2680 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5310   -2.8287    0.3099 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3651   -1.3019   -1.3676 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9334    2.0174   -0.1791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4191    3.0518    0.3797 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0387    2.2368   -1.0027 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6164    3.5495   -1.2418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5638    4.4227   -1.8605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4195    3.9829   -2.0841 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8382    5.7400   -2.1984 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9179   -3.8065   -0.9090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1058   -2.5426   -1.4782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3535   -2.2164   -1.5605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8650   -1.2604    0.3837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9931   -2.5040    2.1340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2420    0.8290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4930    0.0303    1.8071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0708    0.2451   -0.9030 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7984    1.1617    1.8476 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1373   -0.0796    2.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5052    1.4628    1.4615 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3622   -0.0629    1.3974 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8847    0.4725   -0.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7406   -1.8658   -0.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9047   -3.2846    1.4486 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4360   -1.9339    2.3167 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2298   -1.6778   -2.3069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4934    1.4400   -1.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9720    4.0305   -0.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4446    3.4849   -1.9718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5190    6.0701   -3.0909 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 16 18  1  0
  8 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  6
  3 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  6
  9 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  6
 15 40  1  0
 15 41  1  0
 18 42  1  0
 21 43  1  0
 22 44  1  0
 22 45  1  0
 25 46  1  0
M  END

ChEBI
  Mrv1652309042000172D          

 25 24  0  0  1  0            999 V2000
   14.6394  -28.8899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9249  -28.4774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9249  -27.6524    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.2104  -27.2399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2104  -26.4149    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.9249  -26.0024    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6394  -26.4149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6394  -27.2399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3539  -26.0024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0684  -26.4149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7828  -26.0024    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.4973  -26.4149    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7828  -25.1774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4973  -24.7649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0684  -24.7649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4959  -26.0024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4959  -25.1774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7815  -26.4149    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0670  -26.0024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3524  -26.4149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6381  -26.0024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3524  -27.2399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2104  -28.8899    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.4959  -28.4774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2104  -29.7149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2 23  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5 16  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029542

> <DATABASE_NAME>
MIME

> <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

> <FORMULA>
C13H21N3O8S

> <MOLECULAR_WEIGHT>
379.386

> <EXACT_MASS>
379.104935353

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
36.011916776462776

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-2.88

> <JCHEM_LOGP>
-5.369701498472575

> <ALOGPS_LOGS>
-1.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.343963632400796

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7414579722275407

> <JCHEM_PKA_STRONGEST_BASIC>
9.311036181503438

> <JCHEM_POLAR_SURFACE_AREA>
196.12

> <JCHEM_REFRACTIVITY>
84.7788

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.55e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
S-lactoylglutathione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001066
     RDKit          3D
S-Lactoylglutathione
 46 45  0  0  0  0  0  0  0  0999 V2000
   -5.1401   -2.7183   -0.9714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1777   -2.1398    0.4267 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7015   -3.0347    1.3452 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8264   -1.7031    0.8602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3826   -2.1568    1.8980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8508   -0.5565   -0.0731 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2839   -0.2753    0.7608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3642    0.6894    0.0550 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8388    0.7671    0.8876 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1002    0.3102    0.4212 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1788   -0.1736   -0.7409 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3105    0.3803    1.2390 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5498   -0.1557    0.6302 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5097   -1.6190    0.2558 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2602   -2.4588    1.4097 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559   -1.9471   -0.2680 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5310   -2.8287    0.3099 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3651   -1.3019   -1.3676 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9334    2.0174   -0.1791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4191    3.0518    0.3797 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0387    2.2368   -1.0027 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6164    3.5495   -1.2418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5638    4.4227   -1.8605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4195    3.9829   -2.0841 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8382    5.7400   -2.1984 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9179   -3.8065   -0.9090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1058   -2.5426   -1.4782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3535   -2.2164   -1.5605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8650   -1.2604    0.3837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9931   -2.5040    2.1340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2420    0.8290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4930    0.0303    1.8071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0708    0.2451   -0.9030 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7984    1.1617    1.8476 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1373   -0.0796    2.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5052    1.4628    1.4615 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3622   -0.0629    1.3974 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8847    0.4725   -0.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7406   -1.8658   -0.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9047   -3.2846    1.4486 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4360   -1.9339    2.3167 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2298   -1.6778   -2.3069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4934    1.4400   -1.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9720    4.0305   -0.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4446    3.4849   -1.9718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5190    6.0701   -3.0909 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 16 18  1  0
  8 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  6
  3 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  6
  9 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  6
 15 40  1  0
 15 41  1  0
 18 42  1  0
 21 43  1  0
 22 44  1  0
 22 45  1  0
 25 46  1  0
M  END

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: ChEBI                                             
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  O   UNK     0      27.327 -53.928   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      25.993 -53.158   0.000  0.00  0.00           C+0
HETATM    3  S   UNK     0      25.993 -51.618   0.000  0.00  0.00           S+0
HETATM    4  C   UNK     0      24.659 -50.848   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      24.659 -49.308   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      25.993 -48.538   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      27.327 -49.308   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      27.327 -50.848   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      28.661 -48.538   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      29.994 -49.308   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      31.328 -48.538   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      32.662 -49.308   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      31.328 -46.998   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      32.662 -46.228   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      29.994 -46.228   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      23.326 -48.538   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      23.326 -46.998   0.000  0.00  0.00           O+0
HETATM   18  N   UNK     0      21.992 -49.308   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      20.658 -48.538   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      19.324 -49.308   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      17.991 -48.538   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      19.324 -50.848   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      24.659 -53.928   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      23.326 -53.158   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      24.659 -55.468   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   23                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   16                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    5   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23    2   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   48    0
END

COMPND    HMDB0001066
HETATM    1  C1  UNL     1      -5.140  -2.718  -0.971  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.178  -2.140   0.427  1.00  0.00           C  
HETATM    3  O1  UNL     1      -5.702  -3.035   1.345  1.00  0.00           O  
HETATM    4  C3  UNL     1      -3.826  -1.703   0.860  1.00  0.00           C  
HETATM    5  O2  UNL     1      -3.383  -2.157   1.898  1.00  0.00           O  
HETATM    6  S1  UNL     1      -2.851  -0.556  -0.073  1.00  0.00           S  
HETATM    7  C4  UNL     1      -1.284  -0.275   0.761  1.00  0.00           C  
HETATM    8  C5  UNL     1      -0.364   0.689   0.055  1.00  0.00           C  
HETATM    9  N1  UNL     1       0.839   0.767   0.888  1.00  0.00           N  
HETATM   10  C6  UNL     1       2.100   0.310   0.421  1.00  0.00           C  
HETATM   11  O3  UNL     1       2.179  -0.174  -0.741  1.00  0.00           O  
HETATM   12  C7  UNL     1       3.311   0.380   1.239  1.00  0.00           C  
HETATM   13  C8  UNL     1       4.550  -0.156   0.630  1.00  0.00           C  
HETATM   14  C9  UNL     1       4.510  -1.619   0.256  1.00  0.00           C  
HETATM   15  N2  UNL     1       4.260  -2.459   1.410  1.00  0.00           N  
HETATM   16  C10 UNL     1       5.856  -1.947  -0.268  1.00  0.00           C  
HETATM   17  O4  UNL     1       6.531  -2.829   0.310  1.00  0.00           O  
HETATM   18  O5  UNL     1       6.365  -1.302  -1.368  1.00  0.00           O  
HETATM   19  C11 UNL     1      -0.933   2.017  -0.179  1.00  0.00           C  
HETATM   20  O6  UNL     1      -0.419   3.052   0.380  1.00  0.00           O  
HETATM   21  N3  UNL     1      -2.039   2.237  -1.003  1.00  0.00           N  
HETATM   22  C12 UNL     1      -2.616   3.549  -1.242  1.00  0.00           C  
HETATM   23  C13 UNL     1      -1.564   4.423  -1.860  1.00  0.00           C  
HETATM   24  O7  UNL     1      -0.420   3.983  -2.084  1.00  0.00           O  
HETATM   25  O8  UNL     1      -1.838   5.740  -2.198  1.00  0.00           O  
HETATM   26  H1  UNL     1      -4.918  -3.806  -0.909  1.00  0.00           H  
HETATM   27  H2  UNL     1      -6.106  -2.543  -1.478  1.00  0.00           H  
HETATM   28  H3  UNL     1      -4.353  -2.216  -1.560  1.00  0.00           H  
HETATM   29  H4  UNL     1      -5.865  -1.260   0.384  1.00  0.00           H  
HETATM   30  H5  UNL     1      -5.993  -2.504   2.134  1.00  0.00           H  
HETATM   31  H6  UNL     1      -0.714  -1.242   0.829  1.00  0.00           H  
HETATM   32  H7  UNL     1      -1.493   0.030   1.807  1.00  0.00           H  
HETATM   33  H8  UNL     1      -0.071   0.245  -0.903  1.00  0.00           H  
HETATM   34  H9  UNL     1       0.798   1.162   1.848  1.00  0.00           H  
HETATM   35  H10 UNL     1       3.137  -0.080   2.244  1.00  0.00           H  
HETATM   36  H11 UNL     1       3.505   1.463   1.462  1.00  0.00           H  
HETATM   37  H12 UNL     1       5.362  -0.063   1.397  1.00  0.00           H  
HETATM   38  H13 UNL     1       4.885   0.472  -0.219  1.00  0.00           H  
HETATM   39  H14 UNL     1       3.741  -1.866  -0.503  1.00  0.00           H  
HETATM   40  H15 UNL     1       4.905  -3.285   1.449  1.00  0.00           H  
HETATM   41  H16 UNL     1       4.436  -1.934   2.317  1.00  0.00           H  
HETATM   42  H17 UNL     1       6.230  -1.678  -2.307  1.00  0.00           H  
HETATM   43  H18 UNL     1      -2.493   1.440  -1.495  1.00  0.00           H  
HETATM   44  H19 UNL     1      -2.972   4.031  -0.324  1.00  0.00           H  
HETATM   45  H20 UNL     1      -3.445   3.485  -1.972  1.00  0.00           H  
HETATM   46  H21 UNL     1      -1.519   6.070  -3.091  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3    4   29
CONECT    3   30
CONECT    4    5    5    6
CONECT    6    7
CONECT    7    8   31   32
CONECT    8    9   19   33
CONECT    9   10   34
CONECT   10   11   11   12
CONECT   12   13   35   36
CONECT   13   14   37   38
CONECT   14   15   16   39
CONECT   15   40   41
CONECT   16   17   17   18
CONECT   18   42
CONECT   19   20   20   21
CONECT   21   22   43
CONECT   22   23   44   45
CONECT   23   24   24   25
CONECT   25   46
END

HMDB0001066
     RDKit          3D
S-Lactoylglutathione
 46 45  0  0  0  0  0  0  0  0999 V2000
   -5.1401   -2.7183   -0.9714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1777   -2.1398    0.4267 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7015   -3.0347    1.3452 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8264   -1.7031    0.8602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3826   -2.1568    1.8980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8508   -0.5565   -0.0731 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2839   -0.2753    0.7608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3642    0.6894    0.0550 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8388    0.7671    0.8876 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1002    0.3102    0.4212 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1788   -0.1736   -0.7409 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3105    0.3803    1.2390 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5498   -0.1557    0.6302 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5097   -1.6190    0.2558 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2602   -2.4588    1.4097 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559   -1.9471   -0.2680 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5310   -2.8287    0.3099 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3651   -1.3019   -1.3676 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9334    2.0174   -0.1791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4191    3.0518    0.3797 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0387    2.2368   -1.0027 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6164    3.5495   -1.2418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5638    4.4227   -1.8605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4195    3.9829   -2.0841 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8382    5.7400   -2.1984 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9179   -3.8065   -0.9090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1058   -2.5426   -1.4782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3535   -2.2164   -1.5605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8650   -1.2604    0.3837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9931   -2.5040    2.1340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2420    0.8290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4930    0.0303    1.8071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0708    0.2451   -0.9030 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7984    1.1617    1.8476 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1373   -0.0796    2.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5052    1.4628    1.4615 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3622   -0.0629    1.3974 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8847    0.4725   -0.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7406   -1.8658   -0.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9047   -3.2846    1.4486 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4360   -1.9339    2.3167 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2298   -1.6778   -2.3069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4934    1.4400   -1.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9720    4.0305   -0.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4446    3.4849   -1.9718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5190    6.0701   -3.0909 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 16 18  1  0
  8 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  6
  3 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  6
  9 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  6
 15 40  1  0
 15 41  1  0
 18 42  1  0
 21 43  1  0
 22 44  1  0
 22 45  1  0
 25 46  1  0
M  END

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

Molecular Formula

C₁₃H₂₁N₃O₈S

Average Mass

379.386

Monoisotopic Mass

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 )

Functional Ontology

Not Available

Physical Properties

State

Solid

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

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Biological Properties

Cellular Locations

Mitochondria

Biospecimen Locations

Feces

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
MMDBp0192059	Lactoylglutathione lyase	Unknown	Q04760	Homo_sapiens
MMDBp0192432	Hydroxyacylglutathione hydrolase, mitochondrial	Unknown	Q16775	Homo_sapiens
MMDBp0194023	Hydroxyacylglutathione hydrolase-like protein	Unknown	Q6PII5	Homo_sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

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
Bacteria	Proteobacteria	185	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human feces; pleural fluid plaque; bal	Unknown; Metabolic reconstruction
Bacteria	Firmicutes	299	Human feces; Human pleural fluid plaque; Pig ; Human ; Cattle	Metabolic reconstruction
Bacteria	Actinobacteria	77	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human	Metabolic reconstruction
Bacteria	Bacteroidetes	104	Human feces; Human appendix biopsy; Human	Metabolic reconstruction
Bacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1	Human feces	Metabolic reconstruction
Bacteria	Fusobacteria	20	Human feces; Human	Metabolic reconstruction
Bacteria	Synergistetes	2	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	3	Human feces	Metabolic reconstruction
Bacteria	Candidatus Melainabacteria	1	Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	3	Human feces	Unknown
Bacteria	nah	1

Exposure Sources

Food Exposures

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0001066

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

CMMC Knowledgebase

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-Lactoylglutathione (MMDBc0029542)

MOL for #<Metabolite:0x0000560be2651f50>

3D MOL for #<Metabolite:0x0000560be2651f50>

3D SDF for #<Metabolite:0x0000560be2651f50>

3D-SDF for #<Metabolite:0x0000560be2651f50>

PDB for #<Metabolite:0x0000560be2651f50>

3D PDB for #<Metabolite:0x0000560be2651f50>

SMILES for #<Metabolite:0x0000560be2651f50>

INCHI for #<Metabolite:0x0000560be2651f50>

Structure for #<Metabolite:0x0000560be2651f50>

3D Structure for #<Metabolite:0x0000560be2651f50>