NP-MRD: Showing NP-Card for gamma-Glutamylcysteine (NP0000885)

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Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2020-11-24 22:19:07 UTC

NP-MRD ID

NP0000885

Secondary Accession Numbers

None

Natural Product 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>
NP0000885

> <DATABASE_NAME>
NP-MRD

> <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

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 Mass

250.2720 Da

Monoisotopic Mass

250.06234 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Arabidopsis thaliana	KNApSAcK Database	22123792
Cannabis sativa	CannabisDB	Not Available
Mus musculus	LOTUS Database	35616633
Trypanosoma brucei	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Escherichia coli	KNApSAcK Database	22123792

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 )

Physical Properties

State

Solid

Experimental 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

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

External Links

HMDB ID

HMDB0001049

DrugBank ID

DB03408

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

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 ]

Showing NP-Card for gamma-Glutamylcysteine (NP0000885)

MOL for NP0000885 (gamma-Glutamylcysteine)

3D MOL for NP0000885 (gamma-Glutamylcysteine)

3D SDF for NP0000885 (gamma-Glutamylcysteine)

3D-SDF for NP0000885 (gamma-Glutamylcysteine)

PDB for NP0000885 (gamma-Glutamylcysteine)

3D PDB for NP0000885 (gamma-Glutamylcysteine)

SMILES for NP0000885 (gamma-Glutamylcysteine)

INCHI for NP0000885 (gamma-Glutamylcysteine)

Structure for NP0000885 (gamma-Glutamylcysteine)

3D Structure for NP0000885 (gamma-Glutamylcysteine)