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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4) Show 4 proteins XML

enzymes (4) Show 4 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 15:41:40 UTC

HMDB ID

HMDB0001049

Secondary Accession Numbers

HMDB0029146
HMDB01049
HMDB29146

Metabolite Identification

Common Name

gamma-Glutamylcysteine

Description

gamma-Glutamylcysteine is a dipeptide composed of gamma-glutamate and cysteine, and is a proteolytic breakdown product of larger proteins. It belongs to the family of N-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. gamma-Glutamylcysteine is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. gamma-Glutamylcysteine is a product of enzyme glutamate-cysteine ligase [EC 6.3.2.2] and a substrate of enzyme glutathione synthase [EC 6.3.2.3] in the glutamate metabolism pathway (KEGG).

Structure

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

HMDB0001049
     RDKit          3D
gamma-Glutamylcysteine
 30 29  0  0  0  0  0  0  0  0999 V2000
    3.4175   -0.8773    1.1524 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1856   -0.8558   -0.2752 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0145    0.0917   -0.5115 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8416   -0.4624    0.2391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3769    0.3490    0.1079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3200    1.3974   -0.5993 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5677   -0.0498    0.7621 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8066    0.6750    0.6946 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8873   -0.1533    0.0284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3213   -0.5498   -1.6519 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2386    1.2069    2.0021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6053    1.0538    3.0731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4229    1.9233    2.0493 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3978   -0.4436   -0.9735 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4334   -0.1727   -0.3089 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5104   -0.3209   -2.3507 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8995   -1.6319    1.6277 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2167    0.0633    1.5425 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8379   -1.8635   -0.5866 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3256    1.0698   -0.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8285    0.2650   -1.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6127   -1.4681   -0.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1415   -0.6151    1.2848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5500   -0.9215    1.3286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6148    1.5747    0.0406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0185   -1.0744    0.6361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8313    0.4027   -0.0042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5074   -1.9166   -1.9309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5509    2.7720    1.4854 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9562    0.5321   -2.7134 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  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  2  0
 11 13  1  0
  2 14  1  0
 14 15  2  0
 14 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  6
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  7 24  1  0
  8 25  1  6
  9 26  1  0
  9 27  1  0
 10 28  1  0
 13 29  1  0
 16 30  1  0
M  END


  Mrv1652309042000172D          

 16 15  0  0  0  0            999 V2000
    0.7985   -0.4610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5129   -0.0485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9419    0.7765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9419   -0.0485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6564   -0.4610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2275   -0.4610    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2275   -1.2860    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0840   -0.0485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0840    0.7765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6304   -1.2860    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3449   -1.6985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3449   -2.5235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0593   -1.2860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7986   -1.2860    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.0840   -1.6985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6304   -0.4610    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 16  8  1  0  0  0  0
  8  1  1  0  0  0  0
  1  2  1  0  0  0  0
  2  6  1  0  0  0  0
  6  4  1  0  0  0  0
  4  3  2  0  0  0  0
  4  5  1  0  0  0  0
  6  7  1  1  0  0  0
  8  9  2  0  0  0  0
 10 16  1  1  0  0  0
 10 11  1  0  0  0  0
 10 15  1  0  0  0  0
 11 13  1  0  0  0  0
 11 12  2  0  0  0  0
 15 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001049

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H14N2O5S/c9-4(7(12)13)1-2-6(11)10-5(3-16)8(14)15/h4-5,16H,1-3,9H2,(H,10,11)(H,12,13)(H,14,15)/t4-,5-/m0/s1

> <INCHI_KEY>
RITKHVBHSGLULN-WHFBIAKZSA-N

> <FORMULA>
C8H14N2O5S

> <MOLECULAR_WEIGHT>
250.272

> <EXACT_MASS>
250.062342258

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
23.361346952294173

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-4-{[(1R)-1-carboxy-2-sulfanylethyl]carbamoyl}butanoic acid

> <ALOGPS_LOGP>
-2.53

> <JCHEM_LOGP>
-3.772310175782215

> <ALOGPS_LOGS>
-1.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.7783691650062323

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.9096914223488342

> <JCHEM_PKA_STRONGEST_BASIC>
9.239048816239574

> <JCHEM_POLAR_SURFACE_AREA>
129.72

> <JCHEM_REFRACTIVITY>
56.311400000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.62e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gamma-glutamylcysteine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001049
     RDKit          3D
gamma-Glutamylcysteine
 30 29  0  0  0  0  0  0  0  0999 V2000
    3.4175   -0.8773    1.1524 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1856   -0.8558   -0.2752 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0145    0.0917   -0.5115 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8416   -0.4624    0.2391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3769    0.3490    0.1079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3200    1.3974   -0.5993 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5677   -0.0498    0.7621 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8066    0.6750    0.6946 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8873   -0.1533    0.0284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3213   -0.5498   -1.6519 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2386    1.2069    2.0021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6053    1.0538    3.0731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4229    1.9233    2.0493 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3978   -0.4436   -0.9735 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4334   -0.1727   -0.3089 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5104   -0.3209   -2.3507 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8995   -1.6319    1.6277 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2167    0.0633    1.5425 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8379   -1.8635   -0.5866 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3256    1.0698   -0.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8285    0.2650   -1.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6127   -1.4681   -0.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1415   -0.6151    1.2848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5500   -0.9215    1.3286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6148    1.5747    0.0406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0185   -1.0744    0.6361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8313    0.4027   -0.0042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5074   -1.9166   -1.9309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5509    2.7720    1.4854 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9562    0.5321   -2.7134 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  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  2  0
 11 13  1  0
  2 14  1  0
 14 15  2  0
 14 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  6
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  7 24  1  0
  8 25  1  6
  9 26  1  0
  9 27  1  0
 10 28  1  0
 13 29  1  0
 16 30  1  0
M  END

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0       1.491  -0.861   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.824  -0.091   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.492   1.449   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       5.492  -0.091   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       6.825  -0.861   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.158  -0.861   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       4.158  -2.401   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       0.157  -0.091   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.157   1.449   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.177  -2.401   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.510  -3.171   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.510  -4.711   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -3.844  -2.401   0.000  0.00  0.00           O+0
HETATM   14  S   UNK     0       1.491  -2.401   0.000  0.00  0.00           S+0
HETATM   15  C   UNK     0       0.157  -3.171   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      -1.177  -0.861   0.000  0.00  0.00           N+0
CONECT    1    8    2                                                       
CONECT    2    1    6                                                       
CONECT    3    4                                                            
CONECT    4    6    3    5                                                  
CONECT    5    4                                                            
CONECT    6    2    4    7                                                  
CONECT    7    6                                                            
CONECT    8   16    1    9                                                  
CONECT    9    8                                                            
CONECT   10   16   11   15                                                  
CONECT   11   10   13   12                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   15                                                            
CONECT   15   10   14                                                       
CONECT   16    8   10                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

COMPND    HMDB0001049
HETATM    1  N1  UNL     1       3.417  -0.877   1.152  1.00  0.00           N  
HETATM    2  C1  UNL     1       3.186  -0.856  -0.275  1.00  0.00           C  
HETATM    3  C2  UNL     1       2.015   0.092  -0.512  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.842  -0.462   0.239  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.377   0.349   0.108  1.00  0.00           C  
HETATM    6  O1  UNL     1      -0.320   1.397  -0.599  1.00  0.00           O  
HETATM    7  N2  UNL     1      -1.568  -0.050   0.762  1.00  0.00           N  
HETATM    8  C5  UNL     1      -2.807   0.675   0.695  1.00  0.00           C  
HETATM    9  C6  UNL     1      -3.887  -0.153   0.028  1.00  0.00           C  
HETATM   10  S1  UNL     1      -3.321  -0.550  -1.652  1.00  0.00           S  
HETATM   11  C7  UNL     1      -3.239   1.207   2.002  1.00  0.00           C  
HETATM   12  O2  UNL     1      -2.605   1.054   3.073  1.00  0.00           O  
HETATM   13  O3  UNL     1      -4.423   1.923   2.049  1.00  0.00           O  
HETATM   14  C8  UNL     1       4.398  -0.444  -0.974  1.00  0.00           C  
HETATM   15  O4  UNL     1       5.433  -0.173  -0.309  1.00  0.00           O  
HETATM   16  O5  UNL     1       4.510  -0.321  -2.351  1.00  0.00           O  
HETATM   17  H1  UNL     1       2.900  -1.632   1.628  1.00  0.00           H  
HETATM   18  H2  UNL     1       3.217   0.063   1.543  1.00  0.00           H  
HETATM   19  H3  UNL     1       2.838  -1.863  -0.587  1.00  0.00           H  
HETATM   20  H4  UNL     1       2.326   1.070  -0.056  1.00  0.00           H  
HETATM   21  H5  UNL     1       1.828   0.265  -1.575  1.00  0.00           H  
HETATM   22  H6  UNL     1       0.613  -1.468  -0.217  1.00  0.00           H  
HETATM   23  H7  UNL     1       1.141  -0.615   1.285  1.00  0.00           H  
HETATM   24  H8  UNL     1      -1.550  -0.921   1.329  1.00  0.00           H  
HETATM   25  H9  UNL     1      -2.615   1.575   0.041  1.00  0.00           H  
HETATM   26  H10 UNL     1      -4.019  -1.074   0.636  1.00  0.00           H  
HETATM   27  H11 UNL     1      -4.831   0.403  -0.004  1.00  0.00           H  
HETATM   28  H12 UNL     1      -3.507  -1.917  -1.931  1.00  0.00           H  
HETATM   29  H13 UNL     1      -4.551   2.772   1.485  1.00  0.00           H  
HETATM   30  H14 UNL     1       4.956   0.532  -2.713  1.00  0.00           H  
CONECT    1    2   17   18
CONECT    2    3   14   19
CONECT    3    4   20   21
CONECT    4    5   22   23
CONECT    5    6    6    7
CONECT    7    8   24
CONECT    8    9   11   25
CONECT    9   10   26   27
CONECT   10   28
CONECT   11   12   12   13
CONECT   13   29
CONECT   14   15   15   16
CONECT   16   30
END

HMDB0001049
     RDKit          3D
gamma-Glutamylcysteine
 30 29  0  0  0  0  0  0  0  0999 V2000
    3.4175   -0.8773    1.1524 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1856   -0.8558   -0.2752 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0145    0.0917   -0.5115 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8416   -0.4624    0.2391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3769    0.3490    0.1079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3200    1.3974   -0.5993 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5677   -0.0498    0.7621 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8066    0.6750    0.6946 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8873   -0.1533    0.0284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3213   -0.5498   -1.6519 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2386    1.2069    2.0021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6053    1.0538    3.0731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4229    1.9233    2.0493 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3978   -0.4436   -0.9735 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4334   -0.1727   -0.3089 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5104   -0.3209   -2.3507 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8995   -1.6319    1.6277 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2167    0.0633    1.5425 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8379   -1.8635   -0.5866 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3256    1.0698   -0.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8285    0.2650   -1.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6127   -1.4681   -0.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1415   -0.6151    1.2848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5500   -0.9215    1.3286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6148    1.5747    0.0406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0185   -1.0744    0.6361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8313    0.4027   -0.0042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5074   -1.9166   -1.9309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5509    2.7720    1.4854 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9562    0.5321   -2.7134 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  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  2  0
 11 13  1  0
  2 14  1  0
 14 15  2  0
 14 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  6
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  7 24  1  0
  8 25  1  6
  9 26  1  0
  9 27  1  0
 10 28  1  0
 13 29  1  0
 16 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5-L-Glutamyl-L-cysteine	ChEBI
gamma-Glu-cys	ChEBI
gamma-L-Glutamyl-L-cysteine	ChEBI
L-gamma-Glutamylcysteine	ChEBI
g-Glu-cys	Generator
Γ-glu-cys	Generator
g-L-Glutamyl-L-cysteine	Generator
Γ-L-glutamyl-L-cysteine	Generator
L-g-Glutamylcysteine	Generator
L-Γ-glutamylcysteine	Generator
g-Glutamylcysteine	Generator
Γ-glutamylcysteine	Generator
Γ-L-glu-L-cys	HMDB
L-Γ-glutamyl-L-cysteine	HMDB
N-Γ-glutamylcysteine	HMDB
N-L-Γ-glutamylcysteine	HMDB
N-L-Γ-glutamyl-L-cysteine	HMDB
gamma-L-Glu-L-cys	HMDB
L-gamma-Glutamyl-L-cysteine	HMDB
N-gamma-Glutamylcysteine	HMDB
N-L-gamma-Glutamylcysteine	HMDB
N-L-gamma-Glutamyl-L-cysteine	HMDB
5-L-Glutamylcysteine	HMDB
H-gamma-Glu-cys-OH	HMDB
L-g-Glutamyl-L-cysteine	HMDB
N-Γ-L-glutamyl-L-cysteine	HMDB
gamma-Glutamylcysteine	HMDB

Chemical Formula

C₈H₁₄N₂O₅S

Average Molecular Weight

250.272

Monoisotopic Molecular Weight

250.062342258

IUPAC Name

(2S)-2-amino-4-{[(1R)-1-carboxy-2-sulfanylethyl]carbamoyl}butanoic acid

Traditional Name

gamma-glutamylcysteine

CAS Registry Number

636-58-8

SMILES

N[C@@H](CCC(=O)N[C@@H](CS)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C8H14N2O5S/c9-4(7(12)13)1-2-6(11)10-5(3-16)8(14)15/h4-5,16H,1-3,9H2,(H,10,11)(H,12,13)(H,14,15)/t4-,5-/m0/s1

InChI Key

RITKHVBHSGLULN-WHFBIAKZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids

Alternative Parents

Substituents

N-acyl-alpha-amino acid
Cysteine or derivatives
Alpha-amino acid
L-alpha-amino acid
Fatty acid
Dicarboxylic acid or derivatives
Amino acid
Alkylthiol
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organosulfur compound
Primary aliphatic amine
Primary amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Amine
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

gamma-glutamylcysteine (CHEBI:17515 )

Ontology

Physiological effect

Adverse health effect

Psychiatric disorder

Schizophrenia - Reduced in human blood (PMID: 25004141 ).

Genetic disorder

Inborn errors of metabolism

5-oxoprolinuria

Organic acidemia

Succinic semialdehyde dehydrogenase deficiency

Cystinosis

Cellular substructure

Macromolecular complex

Blood

Cytoplasm

Ingestion

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Spectral Properties

Experimental Collision Cross Sections

Predictor	Adduct Type	Data Source	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	MetCCS_train_pos	157.658	30932474
AllCCS	[M+H]+	Not Available	157.906	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000494

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.62 g/L	ALOGPS
logP	10^(-2.5) g/L	ALOGPS
logP	10^(-3.8) g/L	ChemAxon
logS	10^(-2) g/L	ALOGPS
pKa (Strongest Acidic)	1.91	ChemAxon
pKa (Strongest Basic)	9.24	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	129.72 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	56.31 m³·mol⁻¹	ChemAxon
Polarizability	23.36 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 Spectral Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	156.674	31661259
DarkChem	[M-H]-	152.995	31661259
AllCCS	[M+H]+	154.077	32859911
AllCCS	[M-H]-	151.726	32859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
gamma-Glutamylcysteine,1TMS,#1	C[Si](C)(C)OC(=O)[C@H](CS)NC(=O)CC[C@H](N)C(=O)O	2293.9	Semi standard non polar	https://arxiv.org/abs/1905.12712
gamma-Glutamylcysteine,1TMS,#2	C[Si](C)(C)OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)O	2282.8	Semi standard non polar	https://arxiv.org/abs/1905.12712
gamma-Glutamylcysteine,1TMS,#3	C[Si](C)(C)SC[C@H](NC(=O)CC[C@H](N)C(=O)O)C(=O)O	2400.8	Semi standard non polar	https://arxiv.org/abs/1905.12712
gamma-Glutamylcysteine,1TMS,#4	C[Si](C)(C)N[C@@H](CCC(=O)N[C@@H](CS)C(=O)O)C(=O)O	2359.6	Semi standard non polar	https://arxiv.org/abs/1905.12712
gamma-Glutamylcysteine,1TMS,#5	C[Si](C)(C)N(C(=O)CC[C@H](N)C(=O)O)[C@@H](CS)C(=O)O	2298.4	Semi standard non polar	https://arxiv.org/abs/1905.12712
gamma-Glutamylcysteine,2TMS,#1	C[Si](C)(C)OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)O[Si](C)(C)C	2276.7	Semi standard non polar	https://arxiv.org/abs/1905.12712
gamma-Glutamylcysteine,2TMS,#2	C[Si](C)(C)OC(=O)[C@H](CS[Si](C)(C)C)NC(=O)CC[C@H](N)C(=O)O	2373.3	Semi standard non polar	https://arxiv.org/abs/1905.12712
gamma-Glutamylcysteine,2TMS,#3	C[Si](C)(C)N[C@@H](CCC(=O)N[C@@H](CS)C(=O)O[Si](C)(C)C)C(=O)O	2355.2	Semi standard non polar	https://arxiv.org/abs/1905.12712
gamma-Glutamylcysteine,2TMS,#4	C[Si](C)(C)OC(=O)[C@H](CS)N(C(=O)CC[C@H](N)C(=O)O)[Si](C)(C)C	2281.2	Semi standard non polar	https://arxiv.org/abs/1905.12712
gamma-Glutamylcysteine,2TMS,#5	C[Si](C)(C)OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS[Si](C)(C)C)C(=O)O	2367.6	Semi standard non polar	https://arxiv.org/abs/1905.12712
gamma-Glutamylcysteine,2TMS,#6	C[Si](C)(C)N[C@@H](CCC(=O)N[C@@H](CS)C(=O)O)C(=O)O[Si](C)(C)C	2346.8	Semi standard non polar	https://arxiv.org/abs/1905.12712
gamma-Glutamylcysteine,2TMS,#7	C[Si](C)(C)OC(=O)[C@@H](N)CCC(=O)N([C@@H](CS)C(=O)O)[Si](C)(C)C	2271.5	Semi standard non polar	https://arxiv.org/abs/1905.12712
gamma-Glutamylcysteine,2TMS,#8	C[Si](C)(C)N[C@@H](CCC(=O)N[C@@H](CS[Si](C)(C)C)C(=O)O)C(=O)O	2452.9	Semi standard non polar	https://arxiv.org/abs/1905.12712
gamma-Glutamylcysteine,2TMS,#9	C[Si](C)(C)SC[C@@H](C(=O)O)N(C(=O)CC[C@H](N)C(=O)O)[Si](C)(C)C	2390.6	Semi standard non polar	https://arxiv.org/abs/1905.12712
gamma-Glutamylcysteine,2TMS,#10	C[Si](C)(C)N([C@@H](CCC(=O)N[C@@H](CS)C(=O)O)C(=O)O)[Si](C)(C)C	2469.3	Semi standard non polar	https://arxiv.org/abs/1905.12712
gamma-Glutamylcysteine,2TMS,#11	C[Si](C)(C)N[C@@H](CCC(=O)N([C@@H](CS)C(=O)O)[Si](C)(C)C)C(=O)O	2359.5	Semi standard non polar	https://arxiv.org/abs/1905.12712
gamma-Glutamylcysteine,1TBDMS,#1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CS)NC(=O)CC[C@H](N)C(=O)O	2558.5	Semi standard non polar	https://arxiv.org/abs/1905.12712
gamma-Glutamylcysteine,1TBDMS,#2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)O	2559.8	Semi standard non polar	https://arxiv.org/abs/1905.12712
gamma-Glutamylcysteine,1TBDMS,#3	CC(C)(C)[Si](C)(C)SC[C@H](NC(=O)CC[C@H](N)C(=O)O)C(=O)O	2659.7	Semi standard non polar	https://arxiv.org/abs/1905.12712
gamma-Glutamylcysteine,1TBDMS,#4	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)N[C@@H](CS)C(=O)O)C(=O)O	2631.5	Semi standard non polar	https://arxiv.org/abs/1905.12712
gamma-Glutamylcysteine,1TBDMS,#5	CC(C)(C)[Si](C)(C)N(C(=O)CC[C@H](N)C(=O)O)[C@@H](CS)C(=O)O	2571.2	Semi standard non polar	https://arxiv.org/abs/1905.12712
gamma-Glutamylcysteine,2TBDMS,#1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)O[Si](C)(C)C(C)(C)C	2766.0	Semi standard non polar	https://arxiv.org/abs/1905.12712
gamma-Glutamylcysteine,2TBDMS,#2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CS[Si](C)(C)C(C)(C)C)NC(=O)CC[C@H](N)C(=O)O	2857.2	Semi standard non polar	https://arxiv.org/abs/1905.12712
gamma-Glutamylcysteine,2TBDMS,#3	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)N[C@@H](CS)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	2838.0	Semi standard non polar	https://arxiv.org/abs/1905.12712
gamma-Glutamylcysteine,2TBDMS,#4	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CS)N(C(=O)CC[C@H](N)C(=O)O)[Si](C)(C)C(C)(C)C	2774.1	Semi standard non polar	https://arxiv.org/abs/1905.12712
gamma-Glutamylcysteine,2TBDMS,#5	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS[Si](C)(C)C(C)(C)C)C(=O)O	2844.5	Semi standard non polar	https://arxiv.org/abs/1905.12712
gamma-Glutamylcysteine,2TBDMS,#6	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)N[C@@H](CS)C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	2836.1	Semi standard non polar	https://arxiv.org/abs/1905.12712
gamma-Glutamylcysteine,2TBDMS,#7	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCC(=O)N([C@@H](CS)C(=O)O)[Si](C)(C)C(C)(C)C	2763.7	Semi standard non polar	https://arxiv.org/abs/1905.12712
gamma-Glutamylcysteine,2TBDMS,#8	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)N[C@@H](CS[Si](C)(C)C(C)(C)C)C(=O)O)C(=O)O	2928.0	Semi standard non polar	https://arxiv.org/abs/1905.12712
gamma-Glutamylcysteine,2TBDMS,#9	CC(C)(C)[Si](C)(C)SC[C@@H](C(=O)O)N(C(=O)CC[C@H](N)C(=O)O)[Si](C)(C)C(C)(C)C	2872.5	Semi standard non polar	https://arxiv.org/abs/1905.12712
gamma-Glutamylcysteine,2TBDMS,#10	CC(C)(C)[Si](C)(C)N([C@@H](CCC(=O)N[C@@H](CS)C(=O)O)C(=O)O)[Si](C)(C)C(C)(C)C	2935.1	Semi standard non polar	https://arxiv.org/abs/1905.12712
gamma-Glutamylcysteine,2TBDMS,#11	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)N([C@@H](CS)C(=O)O)[Si](C)(C)C(C)(C)C)C(=O)O	2834.9	Semi standard non polar	https://arxiv.org/abs/1905.12712

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - gamma-Glutamylcysteine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-054t-1920100000-5ce9a082971db6d9e2e9	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - gamma-Glutamylcysteine GC-EI-TOF (Non-derivatized)	splash10-054t-1920100000-5ce9a082971db6d9e2e9	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Glutamylcysteine GC-MS (Non-derivatized) - 70eV, Positive	splash10-053u-9630000000-344be03dbe2132b00c88	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Glutamylcysteine GC-MS (2 TMS) - 70eV, Positive	splash10-00b9-8494000000-88b1eea1e1badaee084b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Glutamylcysteine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Fibroblasts
Neuron
Placenta
Prostate

Pathways

Name	SMPDB/PathBank	KEGG
Cysteine Metabolism
Glutamate Metabolism
Glutathione metabolism	Not Available
Glutathione Synthetase Deficiency		Not Available
5-Oxoprolinuria		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	3.05 +/- 0.11 uM	Adult (>18 years old)	Both	Normal	25004141	details
Blood	Detected and Quantified	25.0 +/- 8.0 uM	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	1.9 +/- 0.5 uM	Adult (>18 years old)	Male	Normal	8353942	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Normal	27609529	details
Urine	Detected and Quantified	0.46+/-0.14 umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	12707912	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	2.07 +/- 0.12 uM	Adult (>18 years old)	Both	Schizophrenia	25004141	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Both	Crohns disease	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Both	Ulcerative colitis	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Crohns disease	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Ulcerative colitis	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Unclassified IBD	27609529	details

Associated Disorders and Diseases

Disease References

Schizophrenia
Fukushima T, Iizuka H, Yokota A, Suzuki T, Ohno C, Kono Y, Nishikiori M, Seki A, Ichiba H, Watanabe Y, Hongo S, Utsunomiya M, Nakatani M, Sadamoto K, Yoshio T: Quantitative analyses of schizophrenia-associated metabolites in serum: serum D-lactate levels are negatively correlated with gamma-glutamylcysteine in medicated schizophrenia patients. PLoS One. 2014 Jul 8;9(7):e101652. doi: 10.1371/journal.pone.0101652. eCollection 2014. [PubMed:25004141 ]
Crohn's disease
Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Ulcerative colitis
Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]

Associated OMIM IDs

181500 (Schizophrenia)
266600 (Crohn's disease)

External Links

DrugBank ID

DB03408

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

L-GAMMA-GLUTAMYLCYSTEINE

BiGG ID

35655

Wikipedia Link

Gamma-Glutamylcysteine

METLIN ID

5966

PubChem Compound

123938

PDB ID

Not Available

ChEBI ID

17515

Food Biomarker Ontology

Not Available

VMH ID

GLUCYS

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Bridge, Wallace John; Zarka, Martin Hani. Enzymic production of g-glutamylcysteine. PCT Int. Appl. (2006), 76pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Efferth T, Volm M: Glutathione-related enzymes contribute to resistance of tumor cells and low toxicity in normal organs to artesunate. In Vivo. 2005 Jan-Feb;19(1):225-32. [PubMed:15796179 ]
Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Andersson A, Isaksson A, Brattstrom L, Hultberg B: Homocysteine and other thiols determined in plasma by HPLC and thiol-specific postcolumn derivatization. Clin Chem. 1993 Aug;39(8):1590-7. [PubMed:8353942 ]
Iida M, Yasuhara T, Mochizuki H, Takakura H, Yanagisawa T, Kubo H: Two Japanese brothers with hereditary gamma-glutamyl transpeptidase deficiency. J Inherit Metab Dis. 2005;28(1):49-55. [PubMed:15702405 ]
Lochman P, Adam T, Friedecky D, Hlidkova E, Skopkova Z: High-throughput capillary electrophoretic method for determination of total aminothiols in plasma and urine. Electrophoresis. 2003 Apr;24(7-8):1200-7. [PubMed:12707912 ]
Atamna H, Ginsburg H: The malaria parasite supplies glutathione to its host cell--investigation of glutathione transport and metabolism in human erythrocytes infected with Plasmodium falciparum. Eur J Biochem. 1997 Dec 15;250(3):670-9. [PubMed:9461289 ]
Martensson J: Method for determination of free and total glutathione and gamma-glutamylcysteine concentrations in human leukocytes and plasma. J Chromatogr. 1987 Sep 4;420(1):152-7. [PubMed:3667817 ]
Andersson A, Isaksson A, Hultberg B: Homocysteine export from erythrocytes and its implication for plasma sampling. Clin Chem. 1992 Jul;38(7):1311-5. [PubMed:1623596 ]
Kaarteenaho-Wiik R, Kinnula VL: Distribution of antioxidant enzymes in developing human lung, respiratory distress syndrome, and bronchopulmonary dysplasia. J Histochem Cytochem. 2004 Sep;52(9):1231-40. [PubMed:15314090 ]
Diaz-Hernandez JI, Almeida A, Delgado-Esteban M, Fernandez E, Bolanos JP: Knockdown of glutamate-cysteine ligase by small hairpin RNA reveals that both catalytic and modulatory subunits are essential for the survival of primary neurons. J Biol Chem. 2005 Nov 25;280(47):38992-9001. Epub 2005 Sep 23. [PubMed:16183645 ]
Levonen AL, Lapatto R, Saksela M, Raivio KO: Expression of gamma-glutamylcysteine synthetase during development. Pediatr Res. 2000 Feb;47(2):266-70. [PubMed:10674357 ]
Martensson J, Kagedal B, Larsson A: Sulphur amino-acid degradation in subjects with hereditary glutathione synthetase deficiency (5-oxoprolinuria). Eur J Clin Invest. 1985 Dec;15(6):371-4. [PubMed:3938407 ]
Zinellu A, Sotgia S, Posadino AM, Pasciu V, Perino MG, Tadolini B, Deiana L, Carru C: Highly sensitive simultaneous detection of cultured cellular thiols by laser induced fluorescence-capillary electrophoresis. Electrophoresis. 2005 Mar;26(6):1063-70. [PubMed:15706569 ]
Njalsson R, Ristoff E, Carlsson K, Winkler A, Larsson A, Norgren S: Genotype, enzyme activity, glutathione level, and clinical phenotype in patients with glutathione synthetase deficiency. Hum Genet. 2005 Apr;116(5):384-9. Epub 2005 Feb 17. [PubMed:15717202 ]
Lou MF, Dickerson JE Jr, Tung WH, Wolfe JK, Chylack LT Jr: Correlation of nuclear color and opalescence with protein S-thiolation in human lenses. Exp Eye Res. 1999 May;68(5):547-52. [PubMed:10328968 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

Enzyme Details

1. Glutamate--cysteine ligase catalytic subunit

General function:: Involved in glutamate-cysteine ligase activity
Specific function:: Not Available
Gene Name:: GCLC
Uniprot ID:: P48506
Molecular weight:: 68629.42

Reactions

Adenosine triphosphate + L-Glutamic acid + L-Cysteine → ADP + Phosphate + gamma-Glutamylcysteine	details

Enzyme Details

2. Glutaminyl-peptide cyclotransferase

General function:: Involved in peptidase activity
Specific function:: Responsible for the biosynthesis of pyroglutamyl peptides. Has a bias against acidic and tryptophan residues adjacent to the N-terminal glutaminyl residue and a lack of importance of chain length after the second residue. Also catalyzes N-terminal pyroglutamate formation. In vitro, catalyzes pyroglutamate formation of N-terminally truncated form of APP amyloid-beta peptides [Glu-3]-beta-amyloid. May be involved in the N-terminal pyroglutamate formation of several amyloid-related plaque-forming peptides.
Gene Name:: QPCT
Uniprot ID:: Q16769
Molecular weight:: 40876.14

Enzyme Details

3. Glutathione synthetase

General function:: Involved in catalytic activity
Specific function:: Not Available
Gene Name:: GSS
Uniprot ID:: P48637
Molecular weight:: 52384.325

Reactions

Adenosine triphosphate + gamma-Glutamylcysteine + Glycine → ADP + Phosphate + Glutathione	details

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Enzyme Details

4. Gamma-glutamylcyclotransferase

General function:: Involved in acyltransferase activity
Specific function:: Catalyzes the formation of 5-oxoproline from gamma-glutamyl dipeptides and may play a significant role in glutathione homeostasis. Induces release of cytochrome c from mitochondria with resultant induction of apoptosis.
Gene Name:: GGCT
Uniprot ID:: O75223
Molecular weight:: 19091.635

Reactions

gamma-Glutamylcysteine → Pyroglutamic acid + L-Cysteine	details

Showing metabocard for gamma-Glutamylcysteine (HMDB0001049)

MOL for HMDB0001049 (gamma-Glutamylcysteine)

3D MOL for HMDB0001049 (gamma-Glutamylcysteine)

3D SDF for HMDB0001049 (gamma-Glutamylcysteine)

3D-SDF for HMDB0001049 (gamma-Glutamylcysteine)

PDB for HMDB0001049 (gamma-Glutamylcysteine)

3D PDB for HMDB0001049 (gamma-Glutamylcysteine)

SMILES for HMDB0001049 (gamma-Glutamylcysteine)

INCHI for HMDB0001049 (gamma-Glutamylcysteine)

Structure for HMDB0001049 (gamma-Glutamylcysteine)

3D Structure for HMDB0001049 (gamma-Glutamylcysteine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions

References

Reactions