Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:47:01 UTC

Update Date

2022-03-07 02:53:12 UTC

HMDB ID

HMDB0031985

Secondary Accession Numbers

HMDB31985

Metabolite Identification

Common Name

gamma-Glutamyl-S-methylcysteine

Description

gamma-Glutamyl-S-methylcysteine belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. gamma-Glutamyl-S-methylcysteine has been detected, but not quantified in, a few different foods, such as garden onions (Allium cepa), lima beans (Phaseolus lunatus), and soft-necked garlics (Allium sativum L. var. sativum). This could make gamma-glutamyl-S-methylcysteine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on gamma-Glutamyl-S-methylcysteine.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0031985
     RDKit          3D
gamma-Glutamyl-S-methylcysteine
 33 32  0  0  0  0  0  0  0  0999 V2000
    5.8074   -1.0193   -0.3583 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5449   -1.3725    0.8493 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.8755   -1.4314    0.3098 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2175   -0.1319   -0.0507 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8295   -0.4391   -0.4654 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2463    0.0942    0.2679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0121    0.8172    1.2559 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6515   -0.1821   -0.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6130    0.5224    0.8279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0342    0.2051    0.3997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2754    0.6532   -0.9597 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0135    0.8166    1.3455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9767    0.5553    2.5742 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0066    1.6968    0.9266 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8081    0.5693   -1.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1991    0.6940   -2.3236 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0582    1.1657   -1.1879 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6788   -1.7354   -0.2804 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2259   -0.0001   -0.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4424   -1.0979   -1.3849 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2619   -1.9108    1.1318 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7658   -2.1788   -0.5435 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1797    0.5070    0.8668 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7446   -1.0480   -1.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8188   -1.2939   -0.0148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8720    0.0949   -1.1512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4901    0.1298    1.8611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4228    1.6092    0.8500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1634   -0.8956    0.4608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2140   -0.1837   -1.6076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5062    1.3467   -1.2010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5001    1.4676    0.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1771    1.9754   -0.5804 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 12 14  1  0
  4 15  1  0
 15 16  2  0
 15 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 14 32  1  0
 17 33  1  0
M  END


  Mrv0541 02241209352D          

 17 16  0  0  0  0            999 V2000
   -3.5733   -0.4126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8581   -0.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8581    0.8252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7152   -0.4126    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290   -0.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1442   -0.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8595   -0.0014    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7152    1.2378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290    0.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1442    1.2378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1442   -1.2378    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1442   -0.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4290   -0.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7138   -0.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0013   -0.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0013    0.8252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5733   -0.4154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2 12  1  0  0  0  0
  4  5  1  0  0  0  0
  4 15  1  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  6  7  1  0  0  0  0
  7 17  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031985

> <DATABASE_NAME>
hmdb

> <SMILES>
CSCC(NC(=O)CCC(N)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H16N2O5S/c1-17-4-6(9(15)16)11-7(12)3-2-5(10)8(13)14/h5-6H,2-4,10H2,1H3,(H,11,12)(H,13,14)(H,15,16)

> <INCHI_KEY>
UPCDLBPYWXOCOK-UHFFFAOYSA-N

> <FORMULA>
C9H16N2O5S

> <MOLECULAR_WEIGHT>
264.299

> <EXACT_MASS>
264.077992322

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
25.735420861014678

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-4-{[1-carboxy-2-(methylsulfanyl)ethyl]carbamoyl}butanoic acid

> <ALOGPS_LOGP>
-3.00

> <JCHEM_LOGP>
-3.3720079644846814

> <ALOGPS_LOGS>
-1.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.838270905966113

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7830848632610339

> <JCHEM_PKA_STRONGEST_BASIC>
9.31204722192069

> <JCHEM_POLAR_SURFACE_AREA>
129.72

> <JCHEM_REFRACTIVITY>
60.96240000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.86e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-4-{[1-carboxy-2-(methylsulfanyl)ethyl]carbamoyl}butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0031985
     RDKit          3D
gamma-Glutamyl-S-methylcysteine
 33 32  0  0  0  0  0  0  0  0999 V2000
    5.8074   -1.0193   -0.3583 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5449   -1.3725    0.8493 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.8755   -1.4314    0.3098 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2175   -0.1319   -0.0507 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8295   -0.4391   -0.4654 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2463    0.0942    0.2679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0121    0.8172    1.2559 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6515   -0.1821   -0.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6130    0.5224    0.8279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0342    0.2051    0.3997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2754    0.6532   -0.9597 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0135    0.8166    1.3455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9767    0.5553    2.5742 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0066    1.6968    0.9266 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8081    0.5693   -1.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1991    0.6940   -2.3236 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0582    1.1657   -1.1879 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6788   -1.7354   -0.2804 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2259   -0.0001   -0.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4424   -1.0979   -1.3849 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2619   -1.9108    1.1318 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7658   -2.1788   -0.5435 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1797    0.5070    0.8668 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7446   -1.0480   -1.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8188   -1.2939   -0.0148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8720    0.0949   -1.1512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4901    0.1298    1.8611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4228    1.6092    0.8500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1634   -0.8956    0.4608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2140   -0.1837   -1.6076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5062    1.3467   -1.2010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5001    1.4676    0.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1771    1.9754   -0.5804 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 12 14  1  0
  4 15  1  0
 15 16  2  0
 15 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 14 32  1  0
 17 33  1  0
M  END

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  O   UNK     0      -6.670  -0.770   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -5.335  -0.003   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -5.335   1.540   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       1.335  -0.770   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       2.667  -0.003   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.003  -0.770   0.000  0.00  0.00           C+0
HETATM    7  S   UNK     0       5.338  -0.003   0.000  0.00  0.00           S+0
HETATM    8  O   UNK     0       1.335   2.311   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.003   2.311   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0      -4.003  -2.311   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      -4.003  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667  -0.003   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.332  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.002  -0.003   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.002   1.540   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.670  -0.775   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2                                                            
CONECT    4    5   15                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6   17                                                       
CONECT    8    9                                                            
CONECT    9    5    8   10                                                  
CONECT   10    9                                                            
CONECT   11   12                                                            
CONECT   12    2   11   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15    4   14   16                                                  
CONECT   16   15                                                            
CONECT   17    7                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

COMPND    HMDB0031985
HETATM    1  C1  UNL     1       5.807  -1.019  -0.358  1.00  0.00           C  
HETATM    2  S1  UNL     1       4.545  -1.372   0.849  1.00  0.00           S  
HETATM    3  C2  UNL     1       2.876  -1.431   0.310  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.218  -0.132  -0.051  1.00  0.00           C  
HETATM    5  N1  UNL     1       0.829  -0.439  -0.465  1.00  0.00           N  
HETATM    6  C4  UNL     1      -0.246   0.094   0.268  1.00  0.00           C  
HETATM    7  O1  UNL     1      -0.012   0.817   1.256  1.00  0.00           O  
HETATM    8  C5  UNL     1      -1.651  -0.182  -0.105  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.613   0.522   0.828  1.00  0.00           C  
HETATM   10  C7  UNL     1      -4.034   0.205   0.400  1.00  0.00           C  
HETATM   11  N2  UNL     1      -4.275   0.653  -0.960  1.00  0.00           N  
HETATM   12  C8  UNL     1      -5.013   0.817   1.345  1.00  0.00           C  
HETATM   13  O2  UNL     1      -4.977   0.555   2.574  1.00  0.00           O  
HETATM   14  O3  UNL     1      -6.007   1.697   0.927  1.00  0.00           O  
HETATM   15  C9  UNL     1       2.808   0.569  -1.197  1.00  0.00           C  
HETATM   16  O4  UNL     1       2.199   0.694  -2.324  1.00  0.00           O  
HETATM   17  O5  UNL     1       4.058   1.166  -1.188  1.00  0.00           O  
HETATM   18  H1  UNL     1       6.679  -1.735  -0.280  1.00  0.00           H  
HETATM   19  H2  UNL     1       6.226  -0.000  -0.156  1.00  0.00           H  
HETATM   20  H3  UNL     1       5.442  -1.098  -1.385  1.00  0.00           H  
HETATM   21  H4  UNL     1       2.262  -1.911   1.132  1.00  0.00           H  
HETATM   22  H5  UNL     1       2.766  -2.179  -0.543  1.00  0.00           H  
HETATM   23  H6  UNL     1       2.180   0.507   0.867  1.00  0.00           H  
HETATM   24  H7  UNL     1       0.745  -1.048  -1.299  1.00  0.00           H  
HETATM   25  H8  UNL     1      -1.819  -1.294  -0.015  1.00  0.00           H  
HETATM   26  H9  UNL     1      -1.872   0.095  -1.151  1.00  0.00           H  
HETATM   27  H10 UNL     1      -2.490   0.130   1.861  1.00  0.00           H  
HETATM   28  H11 UNL     1      -2.423   1.609   0.850  1.00  0.00           H  
HETATM   29  H12 UNL     1      -4.163  -0.896   0.461  1.00  0.00           H  
HETATM   30  H13 UNL     1      -4.214  -0.184  -1.608  1.00  0.00           H  
HETATM   31  H14 UNL     1      -3.506   1.347  -1.201  1.00  0.00           H  
HETATM   32  H15 UNL     1      -6.500   1.468   0.074  1.00  0.00           H  
HETATM   33  H16 UNL     1       4.177   1.975  -0.580  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3
CONECT    3    4   21   22
CONECT    4    5   15   23
CONECT    5    6   24
CONECT    6    7    7    8
CONECT    8    9   25   26
CONECT    9   10   27   28
CONECT   10   11   12   29
CONECT   11   30   31
CONECT   12   13   13   14
CONECT   14   32
CONECT   15   16   16   17
CONECT   17   33
END

HMDB0031985
     RDKit          3D
gamma-Glutamyl-S-methylcysteine
 33 32  0  0  0  0  0  0  0  0999 V2000
    5.8074   -1.0193   -0.3583 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5449   -1.3725    0.8493 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.8755   -1.4314    0.3098 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2175   -0.1319   -0.0507 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8295   -0.4391   -0.4654 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2463    0.0942    0.2679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0121    0.8172    1.2559 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6515   -0.1821   -0.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6130    0.5224    0.8279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0342    0.2051    0.3997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2754    0.6532   -0.9597 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0135    0.8166    1.3455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9767    0.5553    2.5742 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0066    1.6968    0.9266 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8081    0.5693   -1.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1991    0.6940   -2.3236 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0582    1.1657   -1.1879 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6788   -1.7354   -0.2804 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2259   -0.0001   -0.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4424   -1.0979   -1.3849 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2619   -1.9108    1.1318 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7658   -2.1788   -0.5435 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1797    0.5070    0.8668 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7446   -1.0480   -1.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8188   -1.2939   -0.0148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8720    0.0949   -1.1512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4901    0.1298    1.8611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4228    1.6092    0.8500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1634   -0.8956    0.4608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2140   -0.1837   -1.6076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5062    1.3467   -1.2010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5001    1.4676    0.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1771    1.9754   -0.5804 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 12 14  1  0
  4 15  1  0
 15 16  2  0
 15 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 14 32  1  0
 17 33  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
g-Glutamyl-S-methylcysteine	Generator
Γ-glutamyl-S-methylcysteine	Generator
gamma-Glu-S-methyl-cys	MeSH, HMDB
2-Amino-4-{[1-carboxy-2-(methylsulfanyl)ethyl]-C-hydroxycarbonimidoyl}butanoate	Generator
2-Amino-4-{[1-carboxy-2-(methylsulphanyl)ethyl]-C-hydroxycarbonimidoyl}butanoate	Generator
2-Amino-4-{[1-carboxy-2-(methylsulphanyl)ethyl]-C-hydroxycarbonimidoyl}butanoic acid	Generator
gamma-Glutamyl-S-methylcysteine	MeSH

Chemical Formula

C₉H₁₆N₂O₅S

Average Molecular Weight

264.299

Monoisotopic Molecular Weight

264.077992322

IUPAC Name

2-amino-4-{[1-carboxy-2-(methylsulfanyl)ethyl]carbamoyl}butanoic acid

Traditional Name

2-amino-4-{[1-carboxy-2-(methylsulfanyl)ethyl]carbamoyl}butanoic acid

CAS Registry Number

Not Available

SMILES

CSCC(NC(=O)CCC(N)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C9H16N2O5S/c1-17-4-6(9(15)16)11-7(12)3-2-5(10)8(13)14/h5-6H,2-4,10H2,1H3,(H,11,12)(H,13,14)(H,15,16)

InChI Key

UPCDLBPYWXOCOK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
Gamma-glutamyl alpha-amino acid
Glutamine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Cysteine or derivatives
Alpha-amino acid
Alpha-amino acid or derivatives
N-acyl-amine
Fatty amide
Dicarboxylic acid or derivatives
Fatty acid
Fatty acyl
Secondary carboxylic acid amide
Amino acid or derivatives
Amino acid
Carboxamide group
Thioether
Sulfenyl compound
Dialkylthioether
Carboxylic acid
Organic nitrogen compound
Organonitrogen compound
Primary aliphatic amine
Organooxygen compound
Organosulfur compound
Primary amine
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Amine
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0031985)
Cytoplasm (HMDB: HMDB0031985)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031985)

Source

Endogenous

Endogenous (HMDB: HMDB0031985)

Plant

Plant (HMDB: HMDB0031985)
Fabaceae (HMDB: HMDB0031985)

Exogenous

Food

Food (HMDB: HMDB0031985)

Pulse

Bean

Lima bean (FooDB: FOOD00133)

Vegetable

Onion-family vegetable

Garden onion (FooDB: FOOD00006)

Herb and spice

Herb

Soft-necked garlic (FooDB: FOOD00850)

Exogenous (HMDB: HMDB0031985)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	107 - 109 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	4.86 g/L	ALOGPS
logP	-3	ALOGPS
logP	-3.4	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	1.78	ChemAxon
pKa (Strongest Basic)	9.31	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	129.72 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	60.96 m³·mol⁻¹	ChemAxon
Polarizability	25.74 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	161.443	31661259
DarkChem	[M-H]-	156.305	31661259
DeepCCS	[M+H]+	153.378	30932474
DeepCCS	[M-H]-	150.839	30932474
DeepCCS	[M-2H]-	185.6	30932474
DeepCCS	[M+Na]+	161.586	30932474
AllCCS	[M+H]+	157.8	32859911
AllCCS	[M+H-H2O]+	154.8	32859911
AllCCS	[M+NH4]+	160.6	32859911
AllCCS	[M+Na]+	161.4	32859911
AllCCS	[M-H]-	156.8	32859911
AllCCS	[M+Na-2H]-	157.5	32859911
AllCCS	[M+HCOO]-	158.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.7 minutes	32390414
Predicted by Siyang on May 30, 2022	10.2756 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	9.1 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	412.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	613.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	245.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	49.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	158.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	53.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	278.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	264.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	861.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	627.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	58.2 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	805.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	176.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	174.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	567.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	500.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	368.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
gamma-Glutamyl-S-methylcysteine	CSCC(NC(=O)CCC(N)C(O)=O)C(O)=O	3397.4	Standard polar	33892256
gamma-Glutamyl-S-methylcysteine	CSCC(NC(=O)CCC(N)C(O)=O)C(O)=O	2058.3	Standard non polar	33892256
gamma-Glutamyl-S-methylcysteine	CSCC(NC(=O)CCC(N)C(O)=O)C(O)=O	2563.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
gamma-Glutamyl-S-methylcysteine,1TMS,isomer #1	CSCC(NC(=O)CCC(N)C(=O)O[Si](C)(C)C)C(=O)O	2312.8	Semi standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,1TMS,isomer #2	CSCC(NC(=O)CCC(N)C(=O)O)C(=O)O[Si](C)(C)C	2307.6	Semi standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,1TMS,isomer #3	CSCC(NC(=O)CCC(N[Si](C)(C)C)C(=O)O)C(=O)O	2388.2	Semi standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,1TMS,isomer #4	CSCC(C(=O)O)N(C(=O)CCC(N)C(=O)O)[Si](C)(C)C	2340.3	Semi standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,2TMS,isomer #1	CSCC(NC(=O)CCC(N)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2320.1	Semi standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,2TMS,isomer #2	CSCC(NC(=O)CCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O	2382.2	Semi standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,2TMS,isomer #3	CSCC(C(=O)O)N(C(=O)CCC(N)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2341.7	Semi standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,2TMS,isomer #4	CSCC(NC(=O)CCC(N[Si](C)(C)C)C(=O)O)C(=O)O[Si](C)(C)C	2382.7	Semi standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,2TMS,isomer #5	CSCC(C(=O)O[Si](C)(C)C)N(C(=O)CCC(N)C(=O)O)[Si](C)(C)C	2335.2	Semi standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,2TMS,isomer #6	CSCC(C(=O)O)N(C(=O)CCC(N[Si](C)(C)C)C(=O)O)[Si](C)(C)C	2398.7	Semi standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,2TMS,isomer #7	CSCC(NC(=O)CCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	2528.8	Semi standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,3TMS,isomer #1	CSCC(NC(=O)CCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2371.3	Semi standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,3TMS,isomer #1	CSCC(NC(=O)CCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2317.7	Standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,3TMS,isomer #2	CSCC(C(=O)O[Si](C)(C)C)N(C(=O)CCC(N)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2315.2	Semi standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,3TMS,isomer #2	CSCC(C(=O)O[Si](C)(C)C)N(C(=O)CCC(N)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2344.7	Standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,3TMS,isomer #3	CSCC(C(=O)O)N(C(=O)CCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2386.4	Semi standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,3TMS,isomer #3	CSCC(C(=O)O)N(C(=O)CCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2375.7	Standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,3TMS,isomer #4	CSCC(NC(=O)CCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	2514.4	Semi standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,3TMS,isomer #4	CSCC(NC(=O)CCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	2368.9	Standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,3TMS,isomer #5	CSCC(C(=O)O[Si](C)(C)C)N(C(=O)CCC(N[Si](C)(C)C)C(=O)O)[Si](C)(C)C	2389.1	Semi standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,3TMS,isomer #5	CSCC(C(=O)O[Si](C)(C)C)N(C(=O)CCC(N[Si](C)(C)C)C(=O)O)[Si](C)(C)C	2347.8	Standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,3TMS,isomer #6	CSCC(NC(=O)CCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2527.2	Semi standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,3TMS,isomer #6	CSCC(NC(=O)CCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2394.7	Standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,3TMS,isomer #7	CSCC(C(=O)O)N(C(=O)CCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2520.7	Semi standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,3TMS,isomer #7	CSCC(C(=O)O)N(C(=O)CCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2469.5	Standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,4TMS,isomer #1	CSCC(C(=O)O[Si](C)(C)C)N(C(=O)CCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2351.3	Semi standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,4TMS,isomer #1	CSCC(C(=O)O[Si](C)(C)C)N(C(=O)CCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2407.1	Standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,4TMS,isomer #2	CSCC(NC(=O)CCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2489.0	Semi standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,4TMS,isomer #2	CSCC(NC(=O)CCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2414.3	Standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,4TMS,isomer #3	CSCC(C(=O)O)N(C(=O)CCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2511.6	Semi standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,4TMS,isomer #3	CSCC(C(=O)O)N(C(=O)CCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2494.1	Standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,4TMS,isomer #4	CSCC(C(=O)O[Si](C)(C)C)N(C(=O)CCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2517.0	Semi standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,4TMS,isomer #4	CSCC(C(=O)O[Si](C)(C)C)N(C(=O)CCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2496.1	Standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,5TMS,isomer #1	CSCC(C(=O)O[Si](C)(C)C)N(C(=O)CCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2510.5	Semi standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,5TMS,isomer #1	CSCC(C(=O)O[Si](C)(C)C)N(C(=O)CCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2521.8	Standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,1TBDMS,isomer #1	CSCC(NC(=O)CCC(N)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	2561.5	Semi standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,1TBDMS,isomer #2	CSCC(NC(=O)CCC(N)C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	2560.6	Semi standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,1TBDMS,isomer #3	CSCC(NC(=O)CCC(N[Si](C)(C)C(C)(C)C)C(=O)O)C(=O)O	2625.3	Semi standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,1TBDMS,isomer #4	CSCC(C(=O)O)N(C(=O)CCC(N)C(=O)O)[Si](C)(C)C(C)(C)C	2588.1	Semi standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,2TBDMS,isomer #1	CSCC(NC(=O)CCC(N)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2778.4	Semi standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,2TBDMS,isomer #2	CSCC(NC(=O)CCC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	2841.2	Semi standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,2TBDMS,isomer #3	CSCC(C(=O)O)N(C(=O)CCC(N)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2806.9	Semi standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,2TBDMS,isomer #4	CSCC(NC(=O)CCC(N[Si](C)(C)C(C)(C)C)C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	2841.5	Semi standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,2TBDMS,isomer #5	CSCC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CCC(N)C(=O)O)[Si](C)(C)C(C)(C)C	2799.9	Semi standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,2TBDMS,isomer #6	CSCC(C(=O)O)N(C(=O)CCC(N[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	2860.4	Semi standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,2TBDMS,isomer #7	CSCC(NC(=O)CCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	2955.1	Semi standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,3TBDMS,isomer #1	CSCC(NC(=O)CCC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3016.8	Semi standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,3TBDMS,isomer #1	CSCC(NC(=O)CCC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2872.4	Standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,3TBDMS,isomer #2	CSCC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CCC(N)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2998.9	Semi standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,3TBDMS,isomer #2	CSCC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CCC(N)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2912.0	Standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,3TBDMS,isomer #3	CSCC(C(=O)O)N(C(=O)CCC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3059.9	Semi standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,3TBDMS,isomer #3	CSCC(C(=O)O)N(C(=O)CCC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2891.9	Standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,3TBDMS,isomer #4	CSCC(NC(=O)CCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	3197.5	Semi standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,3TBDMS,isomer #4	CSCC(NC(=O)CCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	2924.0	Standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,3TBDMS,isomer #5	CSCC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CCC(N[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	3069.7	Semi standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,3TBDMS,isomer #5	CSCC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CCC(N[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	2894.0	Standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,3TBDMS,isomer #6	CSCC(NC(=O)CCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3184.7	Semi standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,3TBDMS,isomer #6	CSCC(NC(=O)CCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2909.3	Standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,3TBDMS,isomer #7	CSCC(C(=O)O)N(C(=O)CCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3202.9	Semi standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,3TBDMS,isomer #7	CSCC(C(=O)O)N(C(=O)CCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2950.8	Standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,4TBDMS,isomer #1	CSCC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CCC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3232.9	Semi standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,4TBDMS,isomer #1	CSCC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CCC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3086.5	Standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,4TBDMS,isomer #2	CSCC(NC(=O)CCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3377.6	Semi standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,4TBDMS,isomer #2	CSCC(NC(=O)CCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3108.6	Standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,4TBDMS,isomer #3	CSCC(C(=O)O)N(C(=O)CCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3419.5	Semi standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,4TBDMS,isomer #3	CSCC(C(=O)O)N(C(=O)CCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3140.9	Standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,4TBDMS,isomer #4	CSCC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3419.8	Semi standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,4TBDMS,isomer #4	CSCC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3140.2	Standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,5TBDMS,isomer #1	CSCC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3595.4	Semi standard non polar	33892256
gamma-Glutamyl-S-methylcysteine,5TBDMS,isomer #1	CSCC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3318.0	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Glutamyl-S-methylcysteine GC-MS (Non-derivatized) - 70eV, Positive	splash10-008c-9840000000-63661eee2cd57c6d84ea	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Glutamyl-S-methylcysteine GC-MS (2 TMS) - 70eV, Positive	splash10-00xu-9543000000-dc89de80dfa438164d7b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Glutamyl-S-methylcysteine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - gamma-Glutamyl-S-methylcysteine 6V, Negative-QTOF	splash10-002f-0900000000-a0aadd9e05447cb27476	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - gamma-Glutamyl-S-methylcysteine 6V, Positive-QTOF	splash10-000i-0900000000-3b1b7a8f6721a86df410	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamyl-S-methylcysteine 10V, Positive-QTOF	splash10-0159-1590000000-94dc4bf8f2501b75ce05	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamyl-S-methylcysteine 20V, Positive-QTOF	splash10-00m0-5940000000-ad2bcb09390488282e77	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamyl-S-methylcysteine 40V, Positive-QTOF	splash10-06z0-9400000000-9bfaed33a75c2e474cd9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamyl-S-methylcysteine 10V, Negative-QTOF	splash10-0002-9260000000-700d3081290163f97f29	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamyl-S-methylcysteine 20V, Negative-QTOF	splash10-0002-9430000000-d37cc2260a1aaab234ee	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamyl-S-methylcysteine 40V, Negative-QTOF	splash10-0002-9100000000-ce2818cea6645b10ef27	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamyl-S-methylcysteine 10V, Positive-QTOF	splash10-00lr-3940000000-0fdab3665efb54e96f6e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamyl-S-methylcysteine 20V, Positive-QTOF	splash10-001i-8910000000-a865ac3eaa17c6efbc55	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamyl-S-methylcysteine 40V, Positive-QTOF	splash10-001i-9300000000-b8343d364fe36726b4fd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamyl-S-methylcysteine 10V, Negative-QTOF	splash10-00kb-0950000000-b8aea818961ec6178917	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamyl-S-methylcysteine 20V, Negative-QTOF	splash10-0002-9510000000-93491448fcfeb4720651	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamyl-S-methylcysteine 40V, Negative-QTOF	splash10-0007-9000000000-acc26468f11024bcedc1	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

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

FooDB ID

FDB008678

KNApSAcK ID

Not Available

Chemspider ID

13512618

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13894650

PDB ID

Not Available

ChEBI ID

168622

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for gamma-Glutamyl-S-methylcysteine (HMDB0031985)

MOL for HMDB0031985 (gamma-Glutamyl-S-methylcysteine)

3D MOL for HMDB0031985 (gamma-Glutamyl-S-methylcysteine)

3D SDF for HMDB0031985 (gamma-Glutamyl-S-methylcysteine)

3D-SDF for HMDB0031985 (gamma-Glutamyl-S-methylcysteine)

PDB for HMDB0031985 (gamma-Glutamyl-S-methylcysteine)

3D PDB for HMDB0031985 (gamma-Glutamyl-S-methylcysteine)

SMILES for HMDB0031985 (gamma-Glutamyl-S-methylcysteine)

INCHI for HMDB0031985 (gamma-Glutamyl-S-methylcysteine)

Structure for HMDB0031985 (gamma-Glutamyl-S-methylcysteine)

3D Structure for HMDB0031985 (gamma-Glutamyl-S-methylcysteine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra