MiMeDB: Showing metabocard for gamma-Glutamylalanine (MMDBc0000441)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:37:49 UTC

Update Date

2024-04-30 19:32:25 UTC

Metabolite ID

MMDBc0000441

Metabolite Identification

Common Name

gamma-Glutamylalanine

Description

gamma-Glutamylalanine is a dipeptide composed of gamma-glutamate and alanine, 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-Glutamylalanine is a natural substrate of the enzyme (5-L-glutamyl)-L-amino acid 5-glutamyltransferase (cyclizing) (g-glutamylcyclotransferase, EC 2.3.2.2) in the glutathione metabolism pathway, which cleaves gamma-glutamylalanine to produce L-5-oxoproline. gamma-Glutamylcyclotransferase is widely distributed in both human and animal tissues where it catalyzes the scission of the y-peptide bonds of many different gamma-glutamyl-amino acids and gamma-glutamyl-gamma-glutamyl-amino acids. The latter are 'better' substrates of the enzyme than the corresponding gamma-glutamyl-amino acids (PMID: 2570694 , 2893631 ).

Structure

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

HMDB0006248
     RDKit          3D
gamma-Glutamylalanine
 29 28  0  0  0  0  0  0  0  0999 V2000
   -3.7285    0.7705   -0.9520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9502    0.0783    0.1670 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6130   -0.2211   -0.2452 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4945    0.3678    0.3806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6491    1.1806    1.3280 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8714    0.0384   -0.0675 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230    0.7616    0.7171 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2864    0.3660    0.1925 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4831    0.6781   -1.1791 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5255   -1.0839    0.4025 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4048   -1.5818    1.5608 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8836   -1.9426   -0.6324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6953   -1.1376    0.5207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1059   -2.2540    0.4271 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0142   -1.0907    0.9497 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3711    1.8164   -1.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5924    0.2200   -1.9003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8014    0.7187   -0.6886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9136    0.8083    1.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4865   -0.8971   -1.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0595   -1.0494   -0.0360 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9898    0.3448   -1.1458 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7457    1.8490    0.6081 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8473    0.4540    1.7778 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0640    0.9206    0.7907 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1019    0.0329   -1.6956 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6303    1.6815   -1.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8793   -2.1755   -0.6978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2799   -0.6866    1.8417 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
  2 13  1  0
 13 14  2  0
 13 15  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  1
  3 20  1  0
  6 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  1
  9 26  1  0
  9 27  1  0
 12 28  1  0
 15 29  1  0
M  END

      
  Mrv1652312091700132D          

 15 14  0  0  0  0            999 V2000
 2498.9276 2500.2058    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6425 2499.7940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3574 2500.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.0723 2499.7940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.7875 2500.2058    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2502.5023 2499.7940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.2172 2500.2058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.5023 2498.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.7875 2501.0315    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6425 2498.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2498.2123 2499.7940    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2497.4975 2500.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2496.7826 2499.7940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2497.4975 2501.0315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2498.2123 2498.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 11  1  0  0  0  0
  2  3  1  0  0  0  0
  2 10  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  6  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
 11 12  1  0  0  0  0
 11 15  1  1  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000441

> <DATABASE_NAME>
MIME

> <SMILES>
C[C@H](NC(=O)CC[C@H](N)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H14N2O5/c1-4(7(12)13)10-6(11)3-2-5(9)8(14)15/h4-5H,2-3,9H2,1H3,(H,10,11)(H,12,13)(H,14,15)/t4-,5-/m0/s1

> <INCHI_KEY>
WQXXXVRAFAKQJM-WHFBIAKZSA-N

> <FORMULA>
C8H14N2O5

> <MOLECULAR_WEIGHT>
218.2072

> <EXACT_MASS>
218.090271568

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
20.935963393730972

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-3.36

> <JCHEM_LOGP>
-3.8159177947397183

> <ALOGPS_LOGS>
-1.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.825455393275773

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.9295800715632931

> <JCHEM_PKA_STRONGEST_BASIC>
9.312086881878784

> <JCHEM_POLAR_SURFACE_AREA>
129.71999999999997

> <JCHEM_REFRACTIVITY>
48.58510000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.29e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
g-glu-ala

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0006248
     RDKit          3D
gamma-Glutamylalanine
 29 28  0  0  0  0  0  0  0  0999 V2000
   -3.7285    0.7705   -0.9520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9502    0.0783    0.1670 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6130   -0.2211   -0.2452 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4945    0.3678    0.3806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6491    1.1806    1.3280 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8714    0.0384   -0.0675 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230    0.7616    0.7171 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2864    0.3660    0.1925 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4831    0.6781   -1.1791 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5255   -1.0839    0.4025 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4048   -1.5818    1.5608 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8836   -1.9426   -0.6324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6953   -1.1376    0.5207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1059   -2.2540    0.4271 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0142   -1.0907    0.9497 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3711    1.8164   -1.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5924    0.2200   -1.9003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8014    0.7187   -0.6886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9136    0.8083    1.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4865   -0.8971   -1.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0595   -1.0494   -0.0360 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9898    0.3448   -1.1458 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7457    1.8490    0.6081 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8473    0.4540    1.7778 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0640    0.9206    0.7907 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1019    0.0329   -1.6956 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6303    1.6815   -1.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8793   -2.1755   -0.6978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2799   -0.6866    1.8417 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
  2 13  1  0
 13 14  2  0
 13 15  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  1
  3 20  1  0
  6 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  1
  9 26  1  0
  9 27  1  0
 12 28  1  0
 15 29  1  0
M  END

HEADER    PROTEIN                                 09-DEC-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-DEC-17         0                                  
HETATM    1  N   UNK     0    4664.6654667.051   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0    4665.9994666.282   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    4667.3344667.051   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    4668.6684666.282   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    4670.0034667.051   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    4671.3384666.282   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    4672.6724667.051   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    4671.3384664.741   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0    4670.0034668.592   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0    4665.9994664.741   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0    4663.3304666.282   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    4661.9954667.051   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0    4660.6614666.282   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0    4661.9954668.592   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0    4663.3304664.741   0.000  0.00  0.00           C+0
CONECT    1    2   11                                                       
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    5                                                            
CONECT   10    2                                                            
CONECT   11    1   12   15                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   11                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

COMPND    HMDB0006248
HETATM    1  C1  UNL     1      -3.729   0.770  -0.952  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.950   0.078   0.167  1.00  0.00           C  
HETATM    3  N1  UNL     1      -1.613  -0.221  -0.245  1.00  0.00           N  
HETATM    4  C3  UNL     1      -0.495   0.368   0.381  1.00  0.00           C  
HETATM    5  O1  UNL     1      -0.649   1.181   1.328  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.871   0.038  -0.068  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.923   0.762   0.717  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.286   0.366   0.193  1.00  0.00           C  
HETATM    9  N2  UNL     1       3.483   0.678  -1.179  1.00  0.00           N  
HETATM   10  C7  UNL     1       3.525  -1.084   0.403  1.00  0.00           C  
HETATM   11  O2  UNL     1       3.405  -1.582   1.561  1.00  0.00           O  
HETATM   12  O3  UNL     1       3.884  -1.943  -0.632  1.00  0.00           O  
HETATM   13  C8  UNL     1      -3.695  -1.138   0.521  1.00  0.00           C  
HETATM   14  O4  UNL     1      -3.106  -2.254   0.427  1.00  0.00           O  
HETATM   15  O5  UNL     1      -5.014  -1.091   0.950  1.00  0.00           O  
HETATM   16  H1  UNL     1      -3.371   1.816  -1.008  1.00  0.00           H  
HETATM   17  H2  UNL     1      -3.592   0.220  -1.900  1.00  0.00           H  
HETATM   18  H3  UNL     1      -4.801   0.719  -0.689  1.00  0.00           H  
HETATM   19  H4  UNL     1      -2.914   0.808   1.009  1.00  0.00           H  
HETATM   20  H5  UNL     1      -1.486  -0.897  -1.033  1.00  0.00           H  
HETATM   21  H6  UNL     1       1.060  -1.049  -0.036  1.00  0.00           H  
HETATM   22  H7  UNL     1       0.990   0.345  -1.146  1.00  0.00           H  
HETATM   23  H8  UNL     1       1.746   1.849   0.608  1.00  0.00           H  
HETATM   24  H9  UNL     1       1.847   0.454   1.778  1.00  0.00           H  
HETATM   25  H10 UNL     1       4.064   0.921   0.791  1.00  0.00           H  
HETATM   26  H11 UNL     1       4.102   0.033  -1.696  1.00  0.00           H  
HETATM   27  H12 UNL     1       3.630   1.682  -1.392  1.00  0.00           H  
HETATM   28  H13 UNL     1       4.879  -2.175  -0.698  1.00  0.00           H  
HETATM   29  H14 UNL     1      -5.280  -0.687   1.842  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3   13   19
CONECT    3    4   20
CONECT    4    5    5    6
CONECT    6    7   21   22
CONECT    7    8   23   24
CONECT    8    9   10   25
CONECT    9   26   27
CONECT   10   11   11   12
CONECT   12   28
CONECT   13   14   14   15
CONECT   15   29
END

HMDB0006248
     RDKit          3D
gamma-Glutamylalanine
 29 28  0  0  0  0  0  0  0  0999 V2000
   -3.7285    0.7705   -0.9520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9502    0.0783    0.1670 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6130   -0.2211   -0.2452 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4945    0.3678    0.3806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6491    1.1806    1.3280 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8714    0.0384   -0.0675 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230    0.7616    0.7171 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2864    0.3660    0.1925 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4831    0.6781   -1.1791 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5255   -1.0839    0.4025 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4048   -1.5818    1.5608 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8836   -1.9426   -0.6324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6953   -1.1376    0.5207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1059   -2.2540    0.4271 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0142   -1.0907    0.9497 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3711    1.8164   -1.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5924    0.2200   -1.9003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8014    0.7187   -0.6886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9136    0.8083    1.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4865   -0.8971   -1.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0595   -1.0494   -0.0360 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9898    0.3448   -1.1458 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7457    1.8490    0.6081 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8473    0.4540    1.7778 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0640    0.9206    0.7907 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1019    0.0329   -1.6956 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6303    1.6815   -1.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8793   -2.1755   -0.6978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2799   -0.6866    1.8417 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
  2 13  1  0
 13 14  2  0
 13 15  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  1
  3 20  1  0
  6 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  1
  9 26  1  0
  9 27  1  0
 12 28  1  0
 15 29  1  0
M  END

Synonyms

Value	Source
5-L-Glutamyl-L-alanine	ChEBI
gamma-L-Glutamyl-L-alanine	ChEBI
L-gamma-Glu-L-ala	ChEBI
N-L-gamma-Glutamyl-L-alanine	ChEBI
g-L-Glutamyl-L-alanine	Generator
Γ-L-glutamyl-L-alanine	Generator
L-g-Glu-L-ala	Generator
L-Γ-glu-L-ala	Generator
N-L-g-Glutamyl-L-alanine	Generator
N-L-Γ-glutamyl-L-alanine	Generator
g-Glutamylalanine	Generator
Γ-glutamylalanine	Generator
γ-Glu-Ala	HMDB
γ-L-Glu-L-Ala	HMDB
L-γ-Glutamyl-L-alanine	HMDB
N-γ-Glutamylalanine	HMDB
N-L-γ-Glutamylalanine	HMDB
gamma-Glu-Ala	HMDB
gamma-L-Glu-L-Ala	HMDB
L-gamma-Glutamyl-L-alanine	HMDB
N-gamma-Glutamylalanine	HMDB
N-L-gamma-Glutamylalanine	HMDB
gamma-Glutamylalanine	HMDB, ChEBI
5-L-Glutamylalanine	HMDB
g-Glu-Ala	HMDB
N-γ-L-Glutamyl-L-alanine	HMDB
N-gamma-L-Glutamyl-L-alanine	HMDB

Molecular Formula

C₈H₁₄N₂O₅

Average Mass

218.2072

Monoisotopic Mass

218.090271568

IUPAC Name

(2S)-2-amino-4-{[(1S)-1-carboxyethyl]carbamoyl}butanoic acid

Traditional Name

g-glu-ala

CAS Registry Number

Not Available

SMILES

C[C@H](NC(=O)CC[C@H](N)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C8H14N2O5/c1-4(7(12)13)10-6(11)3-2-5(9)8(14)15/h4-5H,2-3,9H2,1H3,(H,10,11)(H,12,13)(H,14,15)/t4-,5-/m0/s1

InChI Key

WQXXXVRAFAKQJM-WHFBIAKZSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

gamma-glutamylalanine (CHEBI:50619 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	12.9 g/L	ALOGPS
logP	-3.4	ALOGPS
logP	-3.8	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	1.93	ChemAxon
pKa (Strongest Basic)	9.31	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	129.72 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	48.59 m³·mol⁻¹	ChemAxon
Polarizability	20.94 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
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00al-9710000000-e2845b73a5e7cd81881f	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00dj-9332000000-f7980440d2535885b7ab	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
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00xr-2940000000-948d6e9385d802328937	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05br-6900000000-5f1480e854581ee71678	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4r-9200000000-58a633696455e707016d	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0690000000-92c8a111979eb46fa59f	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-06dj-2930000000-1156c919eda2b8e49fae	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0076-9200000000-737e76bca1d968721a2a	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000x-9330000000-8674f1f30751437e8bf9	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9300000000-a9c7516230cc6b7166c1	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-053u-9100000000-bb369086fe31b624af6c	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-056r-1900000000-491b535e4d4e3214438c	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9100000000-51f9fd3eeccf33a98c1c	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000f-9000000000-d6a5f92f606e802c70be	2021-09-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Feces
Placenta

Tissue Locations

Placenta

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0001300	gamma-Glutamylalanine	Pyroglutamic acid	gamma-glutamylcyclotransferase	VMH	2570694
MMDBr0001390	L-Alanine	Cysteinylglycine	gamma-glutamyltransferase 1	VMH	15469854
MMDBr0003984	L-Alanine	gamma-Glutamylalanine	Not Available	VMH	7892271

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	6	Human stool; Human ; Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Bacteroidetes	1	Human feces; Human stool	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Actinobacteria	1	Human ; Human feces; Human sputum; Human saliva; Human supragingival plaque; Human subgingival plaque	Indirect association between microbiota composition and metabolites measured in host biospecimen
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified				HMDB
Human Placenta	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0006248

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

1446127

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440103

PDB ID

Not Available

ChEBI ID

50619

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

York MJ, Crossley MJ, Hyslop SJ, Fisher ML, Kuchel PW: gamma-Glutamylcyclotransferase: inhibition by D-beta-aminoglutaryl-L-alanine and analysis of the solvent kinetic isotope effect. Eur J Biochem. 1989 Sep 1;184(1):97-101. doi: 10.1111/j.1432-1033.1989.tb14994.x. [PubMed:2570694 ]
Takahashi T, Kondo T, Ohno H, Minato S, Ohshima T, Mikuni S, Soda K, Taniguchi N: A spectrophotometric method for the determination of gamma-glutamyl cyclotransferase with alanine dehydrogenase in the presence of anthglutin. Biochem Med Metab Biol. 1987 Dec;38(3):311-6. doi: 10.1016/0885-4505(87)90095-8. [PubMed:2893631 ]
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-Glutamylalanine (MMDBc0000441)

MOL for #<Metabolite:0x00007fdb708afa40>

3D MOL for #<Metabolite:0x00007fdb708afa40>

3D SDF for #<Metabolite:0x00007fdb708afa40>

3D-SDF for #<Metabolite:0x00007fdb708afa40>

PDB for #<Metabolite:0x00007fdb708afa40>

3D PDB for #<Metabolite:0x00007fdb708afa40>

SMILES for #<Metabolite:0x00007fdb708afa40>

INCHI for #<Metabolite:0x00007fdb708afa40>

Structure for #<Metabolite:0x00007fdb708afa40>

3D Structure for #<Metabolite:0x00007fdb708afa40>