MiMeDB: Showing metabocard for gamma-Glutamylcysteine (MMDBc0029535)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:31:23 UTC

Update Date

2024-10-13 08:41:30 UTC

Metabolite ID

MMDBc0029535

Metabolite Identification

Common Name

gamma-Glutamylcysteine

Description

G-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 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>
MMDBc0029535

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₈H₁₄N₂O₅S

Average Mass

250.272

Monoisotopic Mass

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 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	2.62 g/L	ALOGPS
logP	-2.5	ALOGPS
logP	-3.8	ChemAxon
logS	-2	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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-054t-1920100000-5ce9a082971db6d9e2e9	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-054t-1920100000-5ce9a082971db6d9e2e9	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-053u-9630000000-344be03dbe2132b00c88	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00b9-8494000000-88b1eea1e1badaee084b	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0udi-0090000000-50bd1555ededc1afde80	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0udi-0290000000-385ca433f03af7530f47	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0ue9-5490000000-95d45a9cd2bb6249d3a2	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-001i-9510000000-5f29ca903abe05256c83	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-001i-9510000000-5f29ca903abe05256c83	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0002-1490000000-bfce673369358b8079e9	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0690000000-c49357f0d28683125b6d	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-002b-2490000000-41c54aabf6acd4d3b53e	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-014j-9050000000-1137fb3c62232376669c	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05fr-1790000000-2aaa1344429a2297cc6b	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-4920000000-4ad42780853d5599c05b	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05fr-9400000000-b67fd0eaf646aa8f47b3	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000t-1390000000-e723899e4ca71bda7600	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00sj-3960000000-9a2f96ad7d24e7546315	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00e9-9300000000-e14b428bbb5b63d3ae06	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00b9-0910000000-302a05e4e453b27bad64	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004j-3900000000-da869ba294aa1d1e7c49	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000x-9100000000-4bc7ff3637ea175068f0	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0zmi-0960000000-675f718188f5caad73ab	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9600000000-13ddc5ab8de093dd11ab	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9100000000-8b8a5550fa1112649784	2021-09-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Feces
Fibroblasts
Neuron
Placenta
Prostate
Urine

Tissue Locations

Fibroblasts
Neuron
Placenta
Prostate

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192166	Glutamate--cysteine ligase catalytic subunit	Enzyme	P48506	Homo sapiens
MMDBp0192331	Glutaminyl-peptide cyclotransferase	Unknown	Q16769	Homo sapiens
MMDBp0192411	Glutathione synthetase	Enzyme	P48637	Homo sapiens
MMDBp0196046	Gamma-glutamylcyclotransferase	Enzyme	O75223	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0001335	L-Cysteine	gamma-Glutamylcysteine	Not Available	VMH; KEGG	30371894
MMDBr0001389	gamma-Glutamylcysteine	Glutathione	Not Available	VMH; KEGG	30371894
MMDBr0002603	gamma-Glutamylcysteine	Pyroglutamic acid	gamma-glutamylcyclotransferase	VMH; KEGG	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Schizophrenia	Decreased	Association	Human Blood	HMDB	25004141

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	307	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal; Chicken ; Turkey	Unknown; Metabolic reconstruction
Bacteria	Firmicutes	138	Human feces; Human ; Human sputum; Human saliva; Human urine; Human supragingival plaque; Cattle	Metabolic reconstruction
Bacteria	Actinobacteria	41	Human feces; Human ; Cattle	Metabolic reconstruction
Bacteria	Bacteroidetes	2	Human feces	Metabolic reconstruction
Bacteria	Fusobacteria	3	Human feces	Metabolic reconstruction
Bacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	2		Metabolic reconstruction
Bacteria	Cyanobacteria	9
Eukaryota/Fungi	Ascomycota	5	Human feces; Human saliva; Human supragingival plaque	Unknown
Bacteria	nah	1
Bacteria	Chloroflexi	6
Archaea/Archaea	Euryarchaeota	7		Metabolic reconstruction
Bacteria	Planctomycetes	1
Bacteria	Acidobacteria	1
Bacteria	Spirochaetes	2

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Animal		Laminaria	FooDB	31437929
Animal		Haliotis	FooDB	31437929
Animal		Strombidae	FooDB	31437929
Animal		Clupea harengus harengus	FooDB	31437929
Animal		Undaria pinnatifida	FooDB	31437929
Animal		Peprilus triacanthus	FooDB	31437929
Animal		Rhodophyta	FooDB	31437929
Animal		Myoxocephalus	FooDB	31437929
Animal		Eucheuma	FooDB	31437929
Animal		Saccharina japonica	FooDB	31437929
Animal		Spirulina	FooDB	31437929
Animal		Lota lota	FooDB	31437929
Animal		Porphyra umbilicalis	FooDB	31437929
Animal		Chondrus crispus	FooDB	31437929
Plant		Manilkara zapota	FooDB	31437929
Plant		Cucurbita pepo var. clypeata	FooDB	31437929
Plant		Helianthus annuus	FooDB	31437929
Plant		Mentha spicata	FooDB	31437929
Plant		Corylus	FooDB	31437929
Plant		Malus	FooDB	31437929
Plant		Pisum sativum	FooDB	31437929
Plant		Sambucus nigra	FooDB	31437929
Plant		Allium cepa	FooDB	31437929
Plant		Juglans	FooDB	31437929
Plant		Mangifera indica	FooDB	31437929
Plant		Petroselinum crispum	FooDB	31437929
Plant		Ribes nigrum	FooDB	31437929
Plant		Zingiber officinale	FooDB	31437929
Plant		Chamaemelum nobile	FooDB	31437929
Plant		Illicium verum	FooDB	31437929
Plant			FooDB	31437929
Plant		Laurus nobilis	FooDB	31437929
Plant		Auricularia auricula-judae	FooDB	31437929
Plant		Attalea speciosa	FooDB	31437929
Plant		Juglans ailanthifolia	FooDB	31437929
Plant		Melissa officinalis	FooDB	31437929
Plant		Hippophae rhamnoides	FooDB	31437929
Plant		Polygonum alpinum	FooDB	31437929
Plant		Brassica juncea	FooDB	31437929
Plant		Pediomelum esculentum	FooDB	31437929
Plant		Spinacia oleracea	FooDB	31437929
Plant		Auricularia polytricha	FooDB	31437929
Plant		Camellia oleifera	FooDB	31437929
Plant		Vaccinium corymbosum	FooDB	31437929
Plant		Chrysanthemum coronarium	FooDB	31437929
Plant		Eleocharis dulcis	FooDB	31437929
Plant		Thymus vulgaris	FooDB	31437929
Plant		Actinidia chinensis	FooDB	31437929
Plant		Carica papaya	FooDB	31437929
Plant		Pimenta dioica	FooDB	31437929
Plant		Medicago sativa	FooDB	31437929
Plant		Vigna mungo	FooDB	31437929
Plant		Rubus arcticus	FooDB	31437929
Plant		Agaricus bisporus	FooDB	31437929
Plant		Cajanus cajan	FooDB	31437929
Plant		Rumex articus	FooDB	31437929
Plant		Origanum majorana	FooDB	31437929
Plant		Armoracia rusticana	FooDB	31437929
Plant		Hibiscus sabdariffa	FooDB	31437929
Plant		Benincasa hispida	FooDB	31437929
Plant		Prunus persica	FooDB	31437929
Plant		Canarium ovatum	FooDB	31437929
Plant		Ribes aureum var. villosum	FooDB	31437929
Plant		Cucurbita pepo var. cylindrica	FooDB	31437929
Plant		Brassica oleracea var. gemmifera	FooDB	31437929
Plant		Foeniculum vulgare	FooDB	31437929
Plant		Phoenix dactylifera	FooDB	31437929
Plant		Vaccinium macrocarpon	FooDB	31437929
Plant		Arctium lappa	FooDB	31437929
Plant		Brassica oleracea var. gongylodes	FooDB	31437929
Plant			FooDB	31437929
Plant		Juglans cinerea	FooDB	31437929
Plant		Prunus cerasus	FooDB	31437929
Plant		Eruca vesicaria ssp. sativa	FooDB	31437929
Plant		Rosmarinus officinalis	FooDB	31437929
Plant		Artocarpus altilis	FooDB	31437929
Plant		Citrus x paradisi	FooDB	31437929
Plant		Vigna unguiculata	FooDB	31437929
Plant		Cynara scolymus	FooDB	31437929
Plant		Cyathea	FooDB	31437929
Plant		Metroxylon sagu	FooDB	31437929
Plant		Vitis rotundifolia	FooDB	31437929
Plant		Brosimum alicastrum	FooDB	31437929
Plant		Ficus carica	FooDB	31437929
Plant		Lentinus edodes	FooDB	31437929
Plant		Psidium cattleianum	FooDB	31437929
Plant		Beta vulgaris var. rubra	FooDB	31437929
Plant		Castanea mollissima	FooDB	31437929
Plant		Lepidium sativum	FooDB	31437929
Plant		Morus	FooDB	31437929
Plant		Allium sativum	FooDB	31437929
Plant		Helianthus tuberosus	FooDB	31437929
Plant		Phytolacca americana	FooDB	31437929
Plant		Grifola frondosa	FooDB	31437929
Plant		Vitis labrusca	FooDB	31437929
Plant		Tetragonia tetragonioides	FooDB	31437929
Plant		Artemisia vulgaris	FooDB	31437929
Plant		Cucumis metuliferus	FooDB	31437929
Plant		Nephelium lappaceum	FooDB	31437929
Plant		Myrica	FooDB	31437929
Plant		Castanea crenata	FooDB	31437929
Plant			FooDB	31437929
Plant		Corylus avellana	FooDB	31437929
Plant		Litchi chinensis	FooDB	31437929
Plant		Juglans regia	FooDB	31437929
Plant		Quercus	FooDB	31437929
Plant		Trigonella foenum-graecum	FooDB	31437929
Plant		Vaccinium angustifolium	FooDB	31437929
Plant		Malpighia emarginata	FooDB	31437929
Plant		Physalis	FooDB	31437929
Plant		Brassica oleracea var. sabauda	FooDB	31437929
Plant		Thelesperma	FooDB	31437929
Plant		Brassica napus	FooDB	31437929
Plant		Asparagus officinalis	FooDB	31437929
Plant		Chamerion angustifolium	FooDB	31437929
Plant		Levisticum officinale	FooDB	31437929
Plant		Pimpinella anisum	FooDB	31437929
Plant		Vaccinium elliottii	FooDB	31437929
Plant		Artemisia dracunculus	FooDB	31437929
Plant		Matricaria recutita	FooDB	31437929
Plant		Citrus aurantiifolia	FooDB	31437929
Plant		Ziziphus zizyphus	FooDB	31437929
Plant		Lactuca sativa	FooDB	31437929
Plant		Dimocarpus longan	FooDB	31437929
Plant		Eragrostis tef	FooDB	31437929
Plant		Salvia hispanica	FooDB	31437929
Plant		Pistacia vera	FooDB	31437929
Plant		Cynara cardunculus	FooDB	31437929
Plant		Vitellaria paradoxa	FooDB	31437929
Plant		Pangium edule	FooDB	31437929
Plant		Malus pumila	FooDB	31437929
Plant		Allium	FooDB	31437929
Plant		Brassica oleracea var. viridis	FooDB	31437929
Plant		Punica granatum	FooDB	31437929
Plant		Agave	FooDB	31437929
Plant		Hedysarum alpinum	FooDB	31437929
Plant		Diospyros	FooDB	31437929
Plant		Vigna aconitifolia	FooDB	31437929
Plant		Amaranthus	FooDB	31437929
Plant		Gossypium	FooDB	31437929
Plant			FooDB	31437929
Plant		Beta vulgaris	FooDB	31437929
Plant		Mammea americana	FooDB	31437929
Plant	Bulb	Allium sativum l. var. sativum	FooDB	31437929
Plant		Brassica alboglabra	FooDB	31437929
Plant		Annona squamosa	FooDB	31437929
Plant		Apium graveolens var. dulce	FooDB	31437929
Plant		Vitis	FooDB	31437929
Plant		Xanthosoma sagittifolium	FooDB	31437929
Plant		Basella alba	FooDB	31437929
Plant		Cucumis sativus	FooDB	31437929
Plant		Citrus latifolia	FooDB	31437929
Plant		Carya illinoinensis	FooDB	31437929
Plant		Capsicum baccatum var. baccatum	FooDB	31437929
Plant		Byrsonima crassifolia	FooDB	31437929
Plant		Capsicum pubescens	FooDB	31437929
Plant		Cinnamomum aromaticum	FooDB	31437929
Plant		Ribes rubrum	FooDB	31437929
Plant		Crateva religiosa	FooDB	31437929
Plant			FooDB	31437929
Plant		Vitis aestivalis	FooDB	31437929
Plant		Brassica rapa var. chinensis	FooDB	31437929
Plant		Eugenia javanica	FooDB	31437929
Plant		Portulaca oleracea	FooDB	31437929
Plant		Ipomoea batatas	FooDB	31437929
Plant		Mentha arvensis	FooDB	31437929
Plant		Pastinaca sativa	FooDB	31437929
Plant		Cucurbita maxima	FooDB	31437929
Plant		Vaccinium stamineum	FooDB	31437929
Plant		Solanum lycopersicum var. cerasiforme	FooDB	31437929
Plant		Chenopodium album	FooDB	31437929
Plant		Psophocarpus tetragonolobus	FooDB	31437929
Plant		Allium ampeloprasum	FooDB	31437929
Plant		Brassica oleracea	FooDB	31437929
Plant		Sechium edule	FooDB	31437929
Plant		Lactuca sativa l. var. longifolia	FooDB	31437929
Plant		Grataegosorbus mitschurinii	FooDB	31437929
Plant		Diospyros virginiana	FooDB	31437929
Plant		Origanum x majoricum	FooDB	31437929
Plant		Rubus x loganobaccus	FooDB	31437929
Plant		Tragopogon porrifolius	FooDB	31437929
Plant		Taraxacum officinale	FooDB	31437929
Plant		Rumex	FooDB	31437929
Plant		Allium ascalonicum	FooDB	31437929
Plant		Curcuma longa	FooDB	31437929
Plant		Rubus chamaemorus	FooDB	31437929
Plant		Elettaria cardamomum	FooDB	31437929
Plant		Citrullus lanatus var. fistulosus	FooDB	31437929
Plant		Ananas comosus	FooDB	31437929
Plant		Persea americana	FooDB	31437929
Plant		Amelanchier alnifolia	FooDB	31437929
Plant		Eugenia uniflora	FooDB	31437929
Plant		Annona reticulata	FooDB	31437929
Plant		Cichorium intybus	FooDB	31437929
Plant		Sesbania bispinosa	FooDB	31437929
Plant		Chenopodium quinoa	FooDB	31437929
Plant		Brassica oleracea var. botrytis	FooDB	31437929
Plant		Ribes x nidigrolaria	FooDB	31437929
Plant		Garcinia mangostana	FooDB	31437929
Plant		Cucumis melo	FooDB	31437929
Plant		Dioscorea pentaphylla	FooDB	31437929
Plant		Corchorus olitorius	FooDB	31437929
Plant		Juglans nigra	FooDB	31437929
Plant		Lathyrus sativus	FooDB	31437929
Plant		Allium tuberosum	FooDB	31437929
Plant		Cinnamomum verum	FooDB	31437929
Plant		Glycine max	FooDB	31437929
Plant		Gaylussacia baccata	FooDB	31437929
Plant		Petasites japonicus	FooDB	31437929
Plant		Prunus tomentosa	FooDB	31437929
Plant		Ocimum basilicum	FooDB	31437929
Plant		Mentha x piperita	FooDB	31437929
Plant		Maranta arundinacea	FooDB	31437929
Plant		Matteuccia struthiopteris	FooDB	31437929
Plant		Cucurbita moschata	FooDB	31437929
Plant		Macadamia	FooDB	31437929
Plant		Tilia	FooDB	31437929
Plant		Citrus limon	FooDB	31437929
Plant		Vaccinium myrtilloides	FooDB	31437929
Plant		Capsicum annuum var. annuum	FooDB	31437929
Plant		Apium graveolens var. rapaceum	FooDB	31437929
Plant		Papaver	FooDB	31437929
Plant		Rosa	FooDB	31437929
Plant		Nelumbo	FooDB	31437929
Plant		Brassica oleracea var. conica	FooDB	31437929
Plant		Sesamum orientale	FooDB	31437929
Plant		Annona cherimola	FooDB	31437929
Plant		Brassica rapa var. pekinensis	FooDB	31437929
Plant		Brassica rapa	FooDB	31437929
Plant		Lippia graveolens	FooDB	31437929
Plant		Prunus	FooDB	31437929
Plant		Capparis spinosa	FooDB	31437929
Plant		Citrus sinensis	FooDB	31437929
Plant		Lens culinaris	FooDB	31437929
Plant		Vaccinium deliciosum	FooDB	31437929
Plant		Phaseolus lunatus	FooDB	31437929
Plant		Artocarpus heterophyllus	FooDB	31437929
Plant		Prunus virginiana	FooDB	31437929
Plant		Musa acuminata	FooDB	31437929
Plant		Citrullus lanatus	FooDB	31437929
Plant		Linum usitatissimum	FooDB	31437929
Plant		Vigna unguiculata ssp. unguiculata	FooDB	31437929
Plant		Macadamia tetraphylla	FooDB	31437929
Plant		Phyllostachys edulis	FooDB	31437929
Plant		Lagenaria siceraria	FooDB	31437929
Plant		Prunus domestica	FooDB	31437929
Plant		Prunus armeniaca	FooDB	31437929
Plant		Carum carvi	FooDB	31437929
Plant		Allium schoenoprasum	FooDB	31437929
Plant		Carissa macrocarpa	FooDB	31437929
Plant		Citrus reticulata	FooDB	31437929
Plant		Satureja hortensis	FooDB	31437929
Plant		Averrhoa carambola	FooDB	31437929
Plant		Brassica rapa var. rapa	FooDB	31437929
Plant		Sorbus aucuparia	FooDB	31437929
Plant		Anethum graveolens	FooDB	31437929
Plant		Nelumbo nucifera	FooDB	31437929
Plant		Coriandrum sativum	FooDB	31437929
Plant		Bertholletia excelsa	FooDB	31437929
Plant		Brassica oleracea var. costata	FooDB	31437929
Plant		Panax	FooDB	31437929
Plant		Ceratonia siliqua	FooDB	31437929
Plant		Cymbopogon citratus	FooDB	31437929
Plant		Luffa aegyptiaca	FooDB	31437929
Plant		Anacardium occidentale	FooDB	31437929
Plant		Carthamus tinctorius	FooDB	31437929
Plant		Rubus occidentalis	FooDB	31437929
Plant		Vigna umbellata	FooDB	31437929
Plant		Cicer arietinum	FooDB	31437929
Plant		Allium fistulosum	FooDB	31437929
Plant		Capsicum	FooDB	31437929
Plant		Vaccinium alaskaense	FooDB	31437929
Plant		Lupinus	FooDB	31437929
Plant		Tilia cordata	FooDB	31437929
Plant		Prunus persica var. nucipersica	FooDB	31437929
Plant		Camellia sinensis	FooDB	31437929
Plant		Durio zibethinus	FooDB	31437929
Plant		Eriobotrya japonica	FooDB	31437929
Plant		Solanum lycopersicum var. lycopersicum	FooDB	31437929
Plant		Brassica napus var. pabularia	FooDB	31437929
Plant		Oenothera biennis	FooDB	31437929
Plant		Diospyros kaki	FooDB	31437929
Plant		Ribes glandulosum	FooDB	31437929
Plant		Virola surinamensis	FooDB	31437929
Plant		Verbena officinalis	FooDB	31437929
Plant		Phaseolus vulgaris	FooDB	31437929
Plant		Theobroma cacao	FooDB	31437929
Plant		Daucus carota ssp. sativus	FooDB	31437929
Plant		Vaccinium oxycoccos	FooDB	31437929
Plant		Rumex acetosa	FooDB	31437929
Plant		Syzygium aromaticum	FooDB	31437929
Plant		Pyrus pyrifolia	FooDB	31437929
Plant		Vaccinium myrtillus	FooDB	31437929
Plant		Vaccinium parvifolium	FooDB	31437929
Plant		Aloysia triphylla	FooDB	31437929
Plant		Brassica oleracea var. capitata	FooDB	31437929
Plant		Capsicum chinense	FooDB	31437929
Plant		Vicia faba	FooDB	31437929
Plant		Vaccinium reticulatum	FooDB	31437929
Plant		Solanum quitoense	FooDB	31437929
Plant		Ginkgo biloba	FooDB	31437929
Plant		Theobroma grandiflorum	FooDB	31437929
Plant		Vigna unguiculata ssp. cylindrica	FooDB	31437929
Plant		Flammulina velutipes	FooDB	31437929
Plant		Satureja montana	FooDB	31437929
Plant			FooDB	31437929
Plant		Vitis vinifera	FooDB	31437929
Plant		Citrus japonica	FooDB	31437929
Plant		Prunus avium	FooDB	31437929
Plant		Perideridia oregana	FooDB	31437929
Plant		Vaccinium arboreum	FooDB	31437929
Plant		Pouteria sapota	FooDB	31437929
Plant		Wasabia japonica	FooDB	31437929
Plant		Piper nigrum	FooDB	31437929
Plant		Origanum onites	FooDB	31437929
Plant		Capsicum annuum	FooDB	31437929
Plant		Origanum vulgare	FooDB	31437929
Plant		Viburnum edule	FooDB	31437929
Plant		Dioscorea	FooDB	31437929
Plant		Brassica oleracea var. italica	FooDB	31437929
Plant		Momordica charantia	FooDB	31437929
Plant		Vaccinium uliginosum	FooDB	31437929
Plant		Castanea	FooDB	31437929
Plant		Rubus ursinus x idaeus	FooDB	31437929
Plant		Pleurotus ostreatus	FooDB	31437929
Plant		Cirsium	FooDB	31437929
Plant		Solanum melongena	FooDB	31437929
Plant		Opuntia	FooDB	31437929
Plant		Raphanus sativus var. sativus	FooDB	31437929
Plant		Colocasia esculenta	FooDB	31437929
Plant		Prunus persica var. persica	FooDB	31437929
Plant		Anthriscus cerefolium	FooDB	31437929
Plant		Nuphar lutea	FooDB	31437929
Plant		Myristica fragrans	FooDB	31437929
Plant		Pachyrhizus erosus	FooDB	31437929
Plant		Lupinus albus	FooDB	31437929
Plant		Cichorium endivia	FooDB	31437929
Plant		Apium graveolens	FooDB	31437929
Plant		Elaeis	FooDB	31437929
Plant		Cinnamomum	FooDB	31437929
Plant		Ribes uva-crispa	FooDB	31437929
Plant		Feijoa sellowiana	FooDB	31437929
Plant		Dysphania ambrosioides	FooDB	31437929
Plant		Raphanus sativus var. niger	FooDB	31437929
Plant		Photinia melanocarpa	FooDB	31437929
Plant		Salvia officinalis	FooDB	31437929
Plant		Rheum rhabarbarum	FooDB	31437929
Plant		Vaccinium	FooDB	31437929
Plant		Lablab purpureus	FooDB	31437929
Plant		Crocus sativus	FooDB	31437929
Plant		Citrus maxima	FooDB	31437929
Plant		Syzygium jambos	FooDB	31437929
Plant		Salix pulchra	FooDB	31437929
Plant		Castanea sativa	FooDB	31437929
Plant		Cydonia oblonga	FooDB	31437929
Plant		Annona muricata	FooDB	31437929
Plant		Fagus	FooDB	31437929
Plant		Cucurbita	FooDB	31437929
Plant		Opuntia cochenillifera	FooDB	31437929
Plant		Vaccinium ovatum	FooDB	31437929
Plant		Cocos nucifera	FooDB	31437929
Plant		Phaseolus coccineus	FooDB	31437929
Plant		Thymus pulegioides	FooDB	31437929
Plant		Tamarindus indica	FooDB	31437929
Plant		Mespilus germanica	FooDB	31437929
Plant		Brassica rapa var. perviridis	FooDB	31437929
Plant		Cucurbita pepo var. cylindrica	FooDB	31437929
Plant		Mentha aquatica	FooDB	31437929
Plant		Salvia elegans	FooDB	31437929
Plant		Mentha	FooDB	31437929
Plant		Sagittaria latifolia	FooDB	31437929
Plant		Solanum tuberosum	FooDB	31437929
Plant		Olea europaea	FooDB	31437929
Plant		Sambucus	FooDB	31437929
Plant		Pinus	FooDB	31437929
Plant		Psidium guajava	FooDB	31437929
Plant		Syzygium cumini	FooDB	31437929
Plant		Tilia tomentosa	FooDB	31437929
Plant		Typha angustifolia	FooDB	31437929
Plant		Daucus carota	FooDB	31437929
Plant		Empetrum nigrum	FooDB	31437929
Plant		Valerianella locusta	FooDB	31437929
Plant		Myrica rubra	FooDB	31437929
Plant		Vaccinium vitis-idaea	FooDB	31437929
Plant		Vaccinium angustifolium x vaccinium corymbosum	FooDB	31437929
Plant		Sisymbrium	FooDB	31437929
Plant		Vanilla	FooDB	31437929
Plant		Carya	FooDB	31437929
Plant		Brassica oleracea l. var. capitata l. f. alba dc.	FooDB	31437929
Plant		Physalis philadelphica var. immaculata	FooDB	31437929
Plant		Vigna radiata	FooDB	31437929
Plant		Borago officinalis	FooDB	31437929
Plant		Raphanus sativus	FooDB	31437929
Plant		Prunus dulcis	FooDB	31437929
Plant		Hyssopus officinalis	FooDB	31437929
Plant		Manihot esculenta	FooDB	31437929
Plant		Beta vulgaris ssp. cicla	FooDB	31437929
Plant		Scorzonera hispanica	FooDB	31437929
Plant		Vigna unguiculata ssp. sesquipedalis	FooDB	31437929
Plant		Angelica keiskei	FooDB	31437929
Plant		Ipomoea aquatica	FooDB	31437929
Plant		Musa x paradisiaca	FooDB	31437929
Plant		Cuminum cyminum	FooDB	31437929
Plant		Rubus spectabilis	FooDB	31437929
Plant		Allium sativum	FooDB	31437929
Plant		Arachis hypogaea	FooDB	31437929
Plant		Rubus idaeus	FooDB	31437929
Plant		Cantharellus cibarius	FooDB	31437929
Plant		Sinapis alba	FooDB	31437929
Plant		Fragaria x ananassa	FooDB	31437929
Plant		Pyrus communis	FooDB	31437929
Plant		Brassica ruvo	FooDB	31437929
Plant		Apium graveolens var. secalinum	FooDB	31437929
Plant		Morus nigra	FooDB	31437929
Plant		Solanum lycopersicum	FooDB	31437929
Plant		Abelmoschus esculentus	FooDB	31437929
Plant		Moringa oleifera	FooDB	31437929
Plant		Pinus edulis	FooDB	31437929
Plant		Passiflora edulis	FooDB	31437929
Plant		Opuntia macrorhiza	FooDB	31437929
Plant		Vigna angularis	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified							HMDB
Human Blood	Detected and Quantified	2.07	0.12	uM	Adult (>18 years old)	Both	Schizophrenia	HMDB	25004141
Human Urine	Detected and Quantified	0.46	0.14	umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	HMDB	12707912
Human Blood	Detected and Quantified	1.9	0.5	uM	Adult (>18 years old)	Male	Normal	HMDB	8353942
Human Blood	Detected and Quantified	3.05	0.11	uM	Adult (>18 years old)	Both	Normal	HMDB	25004141
Human Blood	Detected and Quantified	25.0	8.0	uM	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Fibroblasts	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Neuron	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified				Children (6 - 18 years old)	Not Specified	Normal	HMDB	27609529

External Links

HMDB ID

HMDB0001049

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

References

Synthesis Reference

Not Available

General References

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 ]
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. doi: 10.1016/0378-4347(87)80166-4. [PubMed:3667817 ]
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. doi: 10.1111/j.1365-2362.1985.tb00287.x. [PubMed:3938407 ]
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 ]
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. doi: 10.1111/j.1432-1033.1997.00670.x. [PubMed:9461289 ]
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. doi: 10.1006/exer.1998.0638. [PubMed:10328968 ]
Levonen AL, Lapatto R, Saksela M, Raivio KO: Expression of gamma-glutamylcysteine synthetase during development. Pediatr Res. 2000 Feb;47(2):266-70. doi: 10.1203/00006450-200002000-00019. [PubMed:10674357 ]
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. doi: 10.1002/elps.200390154. [PubMed:12707912 ]
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. doi: 10.1369/jhc.4A6291.2004. [PubMed:15314090 ]
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. doi: 10.1007/s10545-005-4417-8. [PubMed:15702405 ]
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. doi: 10.1002/elps.200406191. [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. doi: 10.1007/s00439-005-1255-6. Epub 2005 Feb 17. [PubMed:15717202 ]
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 ]
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. doi: 10.1074/jbc.M507065200. Epub 2005 Sep 23. [PubMed:16183645 ]
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 ]
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 ]

Showing metabocard for gamma-Glutamylcysteine (MMDBc0029535)

MOL for #<Metabolite:0x00007f4705b810e8>

3D MOL for #<Metabolite:0x00007f4705b810e8>

3D SDF for #<Metabolite:0x00007f4705b810e8>

3D-SDF for #<Metabolite:0x00007f4705b810e8>

PDB for #<Metabolite:0x00007f4705b810e8>

3D PDB for #<Metabolite:0x00007f4705b810e8>

SMILES for #<Metabolite:0x00007f4705b810e8>

INCHI for #<Metabolite:0x00007f4705b810e8>

Structure for #<Metabolite:0x00007f4705b810e8>

3D Structure for #<Metabolite:0x00007f4705b810e8>