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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-08-13 04:30:33 UTC

Update Date

2021-09-14 15:41:22 UTC

HMDB ID

HMDB0003764

Secondary Accession Numbers

HMDB0028812
HMDB03764
HMDB28812

Metabolite Identification

Common Name

Glutamylalanine

Description

Glutamylalanine is a naturally occurring dipeptide, composed of glutamate and alanine. Glutamylalanine is essential in the supply of glutamate to human erythrocytes. Human erythrocytes are essentially impermeable to glutamate and yet there is a continual requirement for the amino acid for glutathione synthesis. In addition, the intracellular glutamate concentration is approximately five times that of plasma. Glutamylalanine enters the human erythrocyte through saturable membrane-transport systems describable by Michaelis-Menten kinetics. The cytosolic red cell peptidases have a vast capacity to hydrolyse the dipeptide in a process also describable by simple Michaelis-Menten kinetics. The transport process is the rate-determining step in the pathway leading to the production of intracellular glutamate from extracellular glutamylalanine. Glutamylalanine is transported by the human oligopeptide transporter, hPepT1, situated in the small intestine, which is involved in the absorption of nutrient oligopeptides and transports numerous di- and tripeptides. This active transport is being tested for use as a strategy to increase the permeability across the intestine for larger biologically active molecules with low intestinal permeability, in a therapeutic attempt to transport dipeptide-coupled active drug substances via hPepT1 (PMID: 2860897 , 11557350 ).

Structure

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

HMDB0003764
     RDKit          3D
Glutamylalanine
 29 28  0  0  0  0  0  0  0  0999 V2000
   -3.4724   -0.4435    0.2720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5657    0.7135   -0.0728 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2130    0.4374    0.4126 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1228    0.3564   -0.4693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3018    0.5234   -1.7049 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2702    0.0787   -0.0320 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2865   -0.0851    1.4179 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7022   -1.1787   -0.7063 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0911   -1.6177   -0.3832 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1421   -0.6713   -0.7423 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3398   -0.9374   -0.4882 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8486    0.5266   -1.3637 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1206    1.9214    0.6091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4139    2.5112    1.4503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3866    2.4042    0.3390 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1807   -0.1803    1.0914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0686   -0.6857   -0.6275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8351   -1.2923    0.5964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5731    0.8332   -1.1710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0430    0.2960    1.4294 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8620    0.9665   -0.2450 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7069   -0.9030    1.6773 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0194    0.7934    1.8856 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9797   -1.9925   -0.4099 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6061   -1.1255   -1.8116 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3322   -2.5869   -0.8977 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1426   -1.8734    0.7112 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1334    1.4110   -0.9145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1656    1.8003    0.1480 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
  6  8  1  0
  8  9  1  0
  9 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  6
  3 20  1  0
  6 21  1  1
  7 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
 12 28  1  0
 15 29  1  0
M  END


  Mrv1652312081723442D          

 15 14  0  0  0  0            999 V2000
 2499.6425 2499.7941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3574 2500.2058    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2501.0723 2499.7941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.7875 2500.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.5024 2499.7941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.2173 2500.2058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.5024 2498.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3574 2501.0315    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2498.9276 2500.2058    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2498.2124 2499.7941    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 2499.7941    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
 2498.2124 2498.9684    0.0000 C   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
  1  2  1  0  0  0  0
  1  9  1  0  0  0  0
  1 15  2  0  0  0  0
  2  3  1  0  0  0  0
  2  8  1  1  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  7  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 14  1  1  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0003764

> <DATABASE_NAME>
hmdb

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

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

> <INCHI_KEY>
JZDHUJAFXGNDSB-WHFBIAKZSA-N

> <FORMULA>
C8H14N2O5

> <MOLECULAR_WEIGHT>
218.209

> <EXACT_MASS>
218.090271559

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
20.63967157955418

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-3.36

> <JCHEM_LOGP>
-4.015328021361182

> <ALOGPS_LOGS>
-1.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.095796465151948

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.270408791507248

> <JCHEM_PKA_STRONGEST_BASIC>
8.449782306713761

> <JCHEM_POLAR_SURFACE_AREA>
129.72

> <JCHEM_REFRACTIVITY>
48.585100000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.28e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
glutamylalanine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0003764
     RDKit          3D
Glutamylalanine
 29 28  0  0  0  0  0  0  0  0999 V2000
   -3.4724   -0.4435    0.2720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5657    0.7135   -0.0728 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2130    0.4374    0.4126 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1228    0.3564   -0.4693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3018    0.5234   -1.7049 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2702    0.0787   -0.0320 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2865   -0.0851    1.4179 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7022   -1.1787   -0.7063 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0911   -1.6177   -0.3832 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1421   -0.6713   -0.7423 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3398   -0.9374   -0.4882 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8486    0.5266   -1.3637 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1206    1.9214    0.6091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4139    2.5112    1.4503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3866    2.4042    0.3390 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1807   -0.1803    1.0914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0686   -0.6857   -0.6275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8351   -1.2923    0.5964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5731    0.8332   -1.1710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0430    0.2960    1.4294 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8620    0.9665   -0.2450 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7069   -0.9030    1.6773 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0194    0.7934    1.8856 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9797   -1.9925   -0.4099 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6061   -1.1255   -1.8116 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3322   -2.5869   -0.8977 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1426   -1.8734    0.7112 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1334    1.4110   -0.9145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1656    1.8003    0.1480 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
  6  8  1  0
  8  9  1  0
  9 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  6
  3 20  1  0
  6 21  1  1
  7 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
 12 28  1  0
 15 29  1  0
M  END

HEADER    PROTEIN                                 08-DEC-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-DEC-17         0                                  
HETATM    1  C   UNK     0    4665.9994666.282   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    4667.3344667.051   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    4668.6684666.282   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    4670.0034667.051   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    4671.3384666.282   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0    4672.6724667.051   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    4671.3384664.741   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0    4667.3344668.592   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0    4664.6654667.051   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0    4663.3304666.282   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    4661.9954667.051   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0    4660.6614666.282   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    4661.9954668.592   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0    4663.3304664.741   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0    4665.9994664.741   0.000  0.00  0.00           O+0
CONECT    1    2    9   15                                                  
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    2                                                            
CONECT    9    1   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   10                                                            
CONECT   15    1                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

COMPND    HMDB0003764
HETATM    1  C1  UNL     1      -3.472  -0.443   0.272  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.566   0.713  -0.073  1.00  0.00           C  
HETATM    3  N1  UNL     1      -1.213   0.437   0.413  1.00  0.00           N  
HETATM    4  C3  UNL     1      -0.123   0.356  -0.469  1.00  0.00           C  
HETATM    5  O1  UNL     1      -0.302   0.523  -1.705  1.00  0.00           O  
HETATM    6  C4  UNL     1       1.270   0.079  -0.032  1.00  0.00           C  
HETATM    7  N2  UNL     1       1.286  -0.085   1.418  1.00  0.00           N  
HETATM    8  C5  UNL     1       1.702  -1.179  -0.706  1.00  0.00           C  
HETATM    9  C6  UNL     1       3.091  -1.618  -0.383  1.00  0.00           C  
HETATM   10  C7  UNL     1       4.142  -0.671  -0.742  1.00  0.00           C  
HETATM   11  O2  UNL     1       5.340  -0.937  -0.488  1.00  0.00           O  
HETATM   12  O3  UNL     1       3.849   0.527  -1.364  1.00  0.00           O  
HETATM   13  C8  UNL     1      -3.121   1.921   0.609  1.00  0.00           C  
HETATM   14  O4  UNL     1      -2.414   2.511   1.450  1.00  0.00           O  
HETATM   15  O5  UNL     1      -4.387   2.404   0.339  1.00  0.00           O  
HETATM   16  H1  UNL     1      -4.181  -0.180   1.091  1.00  0.00           H  
HETATM   17  H2  UNL     1      -4.069  -0.686  -0.628  1.00  0.00           H  
HETATM   18  H3  UNL     1      -2.835  -1.292   0.596  1.00  0.00           H  
HETATM   19  H4  UNL     1      -2.573   0.833  -1.171  1.00  0.00           H  
HETATM   20  H5  UNL     1      -1.043   0.296   1.429  1.00  0.00           H  
HETATM   21  H6  UNL     1       1.862   0.966  -0.245  1.00  0.00           H  
HETATM   22  H7  UNL     1       0.707  -0.903   1.677  1.00  0.00           H  
HETATM   23  H8  UNL     1       1.019   0.793   1.886  1.00  0.00           H  
HETATM   24  H9  UNL     1       0.980  -1.993  -0.410  1.00  0.00           H  
HETATM   25  H10 UNL     1       1.606  -1.125  -1.812  1.00  0.00           H  
HETATM   26  H11 UNL     1       3.332  -2.587  -0.898  1.00  0.00           H  
HETATM   27  H12 UNL     1       3.143  -1.873   0.711  1.00  0.00           H  
HETATM   28  H13 UNL     1       4.133   1.411  -0.915  1.00  0.00           H  
HETATM   29  H14 UNL     1      -5.166   1.800   0.148  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    8   21
CONECT    7   22   23
CONECT    8    9   24   25
CONECT    9   10   26   27
CONECT   10   11   11   12
CONECT   12   28
CONECT   13   14   14   15
CONECT   15   29
END

HMDB0003764
     RDKit          3D
Glutamylalanine
 29 28  0  0  0  0  0  0  0  0999 V2000
   -3.4724   -0.4435    0.2720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5657    0.7135   -0.0728 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2130    0.4374    0.4126 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1228    0.3564   -0.4693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3018    0.5234   -1.7049 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2702    0.0787   -0.0320 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2865   -0.0851    1.4179 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7022   -1.1787   -0.7063 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0911   -1.6177   -0.3832 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1421   -0.6713   -0.7423 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3398   -0.9374   -0.4882 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8486    0.5266   -1.3637 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1206    1.9214    0.6091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4139    2.5112    1.4503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3866    2.4042    0.3390 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1807   -0.1803    1.0914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0686   -0.6857   -0.6275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8351   -1.2923    0.5964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5731    0.8332   -1.1710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0430    0.2960    1.4294 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8620    0.9665   -0.2450 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7069   -0.9030    1.6773 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0194    0.7934    1.8856 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9797   -1.9925   -0.4099 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6061   -1.1255   -1.8116 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3322   -2.5869   -0.8977 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1426   -1.8734    0.7112 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1334    1.4110   -0.9145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1656    1.8003    0.1480 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
  6  8  1  0
  8  9  1  0
  9 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  6
  3 20  1  0
  6 21  1  1
  7 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
 12 28  1  0
 15 29  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
alpha-Glu-ala	ChEBI
alpha-Glutamylalanine	ChEBI
EA	ChEBI
L-alpha-Glu-L-ala	ChEBI
L-Glu-L-ala	ChEBI
N-L-alpha-Glutamyl-L-alanine	ChEBI
a-Glu-ala	Generator
Α-glu-ala	Generator
a-Glutamylalanine	Generator
Α-glutamylalanine	Generator
L-a-Glu-L-ala	Generator
L-Α-glu-L-ala	Generator
N-L-a-Glutamyl-L-alanine	Generator
N-L-Α-glutamyl-L-alanine	Generator
a-L-Glutamyl-L-alanine	HMDB
alpha-L-Glutamyl-L-alanine	HMDB
Glu-ala	HMDB
L-alpha-Glutamyl-L-amino acid	HMDB
L-Glutamyl-L-alanine	HMDB
Α-L-glu-L-ala	HMDB
Α-L-glutamyl-L-alanine	HMDB
L-Α-glutamyl-L-alanine	HMDB
N-Α-glutamylalanine	HMDB
N-Α-L-glutamyl-L-alanine	HMDB
N-L-Α-glutamylalanine	HMDB
alpha-L-Glu-L-ala	HMDB
L-alpha-Glutamyl-L-alanine	HMDB
N-alpha-Glutamylalanine	HMDB
N-alpha-L-Glutamyl-L-alanine	HMDB
N-L-alpha-Glutamylalanine	HMDB
4-Amino-N-(1-carboxyethyl)-glutaramic acid	HMDB
NSC 334200	HMDB
N-Glutamylalanine	HMDB
N-L-Glutamyl-L-alanine	HMDB
Glutamyl-alanine	HMDB
Glutamic acid alanine dipeptide	HMDB
Glutamate alanine dipeptide	HMDB
Glutamic acid-alanine dipeptide	HMDB
Glutamate-alanine dipeptide	HMDB
e-a Dipeptide	HMDB
EA dipeptide	HMDB
Glutamylalanine	HMDB, ChEBI

Chemical Formula

C₈H₁₄N₂O₅

Average Molecular Weight

218.209

Monoisotopic Molecular Weight

218.090271559

IUPAC Name

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

Traditional Name

glutamylalanine

CAS Registry Number

21064-18-6

SMILES

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

InChI Identifier

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

InChI Key

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

dipeptide (CHEBI:73849 )

Ontology

Not Available

Endogenous (HMDB: HMDB0003764)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	12.8 g/L	ALOGPS
logP	-3.4	ALOGPS
logP	-4	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	3.27	ChemAxon
pKa (Strongest Basic)	8.45	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	20.64 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	151.495	30932474
DeepCCS	[M-H]-	149.137	30932474
DeepCCS	[M-2H]-	182.054	30932474
DeepCCS	[M+Na]+	157.589	30932474
AllCCS	[M+H]+	148.3	32859911
AllCCS	[M+H-H2O]+	144.8	32859911
AllCCS	[M+NH4]+	151.5	32859911
AllCCS	[M+Na]+	152.4	32859911
AllCCS	[M-H]-	146.0	32859911
AllCCS	[M+Na-2H]-	146.8	32859911
AllCCS	[M+HCOO]-	147.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.12 minutes	32390414
Predicted by Siyang on May 30, 2022	9.8104 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	9.01 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	362.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	578.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	258.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	51.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	162.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	50.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	270.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	235.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	776.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	582.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	51.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	727.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	174.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	210.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	576.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	479.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	438.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Glutamylalanine	C[C@H](NC(=O)[C@@H](N)CCC(O)=O)C(O)=O	3037.3	Standard polar	33892256
Glutamylalanine	C[C@H](NC(=O)[C@@H](N)CCC(O)=O)C(O)=O	1773.2	Standard non polar	33892256
Glutamylalanine	C[C@H](NC(=O)[C@@H](N)CCC(O)=O)C(O)=O	2102.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Glutamylalanine,1TMS,isomer #1	C[C@H](NC(=O)[C@@H](N)CCC(=O)O[Si](C)(C)C)C(=O)O	1974.2	Semi standard non polar	33892256
Glutamylalanine,1TMS,isomer #2	C[C@H](NC(=O)[C@@H](N)CCC(=O)O)C(=O)O[Si](C)(C)C	1967.6	Semi standard non polar	33892256
Glutamylalanine,1TMS,isomer #3	C[C@H](NC(=O)[C@H](CCC(=O)O)N[Si](C)(C)C)C(=O)O	1999.6	Semi standard non polar	33892256
Glutamylalanine,1TMS,isomer #4	C[C@@H](C(=O)O)N(C(=O)[C@@H](N)CCC(=O)O)[Si](C)(C)C	1997.5	Semi standard non polar	33892256
Glutamylalanine,2TMS,isomer #1	C[C@H](NC(=O)[C@@H](N)CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2018.3	Semi standard non polar	33892256
Glutamylalanine,2TMS,isomer #2	C[C@H](NC(=O)[C@H](CCC(=O)O[Si](C)(C)C)N[Si](C)(C)C)C(=O)O	2047.9	Semi standard non polar	33892256
Glutamylalanine,2TMS,isomer #3	C[C@@H](C(=O)O)N(C(=O)[C@@H](N)CCC(=O)O[Si](C)(C)C)[Si](C)(C)C	1990.5	Semi standard non polar	33892256
Glutamylalanine,2TMS,isomer #4	C[C@H](NC(=O)[C@H](CCC(=O)O)N[Si](C)(C)C)C(=O)O[Si](C)(C)C	2059.8	Semi standard non polar	33892256
Glutamylalanine,2TMS,isomer #5	C[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@@H](N)CCC(=O)O)[Si](C)(C)C	1998.5	Semi standard non polar	33892256
Glutamylalanine,2TMS,isomer #6	C[C@@H](C(=O)O)N(C(=O)[C@H](CCC(=O)O)N[Si](C)(C)C)[Si](C)(C)C	2068.5	Semi standard non polar	33892256
Glutamylalanine,2TMS,isomer #7	C[C@H](NC(=O)[C@H](CCC(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	2147.2	Semi standard non polar	33892256
Glutamylalanine,3TMS,isomer #1	C[C@H](NC(=O)[C@H](CCC(=O)O[Si](C)(C)C)N[Si](C)(C)C)C(=O)O[Si](C)(C)C	2090.0	Semi standard non polar	33892256
Glutamylalanine,3TMS,isomer #1	C[C@H](NC(=O)[C@H](CCC(=O)O[Si](C)(C)C)N[Si](C)(C)C)C(=O)O[Si](C)(C)C	2071.1	Standard non polar	33892256
Glutamylalanine,3TMS,isomer #1	C[C@H](NC(=O)[C@H](CCC(=O)O[Si](C)(C)C)N[Si](C)(C)C)C(=O)O[Si](C)(C)C	2664.7	Standard polar	33892256
Glutamylalanine,3TMS,isomer #2	C[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@@H](N)CCC(=O)O[Si](C)(C)C)[Si](C)(C)C	2011.0	Semi standard non polar	33892256
Glutamylalanine,3TMS,isomer #2	C[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@@H](N)CCC(=O)O[Si](C)(C)C)[Si](C)(C)C	2086.8	Standard non polar	33892256
Glutamylalanine,3TMS,isomer #2	C[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@@H](N)CCC(=O)O[Si](C)(C)C)[Si](C)(C)C	2999.1	Standard polar	33892256
Glutamylalanine,3TMS,isomer #3	C[C@@H](C(=O)O)N(C(=O)[C@H](CCC(=O)O[Si](C)(C)C)N[Si](C)(C)C)[Si](C)(C)C	2062.4	Semi standard non polar	33892256
Glutamylalanine,3TMS,isomer #3	C[C@@H](C(=O)O)N(C(=O)[C@H](CCC(=O)O[Si](C)(C)C)N[Si](C)(C)C)[Si](C)(C)C	2120.5	Standard non polar	33892256
Glutamylalanine,3TMS,isomer #3	C[C@@H](C(=O)O)N(C(=O)[C@H](CCC(=O)O[Si](C)(C)C)N[Si](C)(C)C)[Si](C)(C)C	2686.1	Standard polar	33892256
Glutamylalanine,3TMS,isomer #4	C[C@H](NC(=O)[C@H](CCC(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	2190.3	Semi standard non polar	33892256
Glutamylalanine,3TMS,isomer #4	C[C@H](NC(=O)[C@H](CCC(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	2138.6	Standard non polar	33892256
Glutamylalanine,3TMS,isomer #4	C[C@H](NC(=O)[C@H](CCC(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	2878.9	Standard polar	33892256
Glutamylalanine,3TMS,isomer #5	C[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@H](CCC(=O)O)N[Si](C)(C)C)[Si](C)(C)C	2070.4	Semi standard non polar	33892256
Glutamylalanine,3TMS,isomer #5	C[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@H](CCC(=O)O)N[Si](C)(C)C)[Si](C)(C)C	2106.9	Standard non polar	33892256
Glutamylalanine,3TMS,isomer #5	C[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@H](CCC(=O)O)N[Si](C)(C)C)[Si](C)(C)C	2588.9	Standard polar	33892256
Glutamylalanine,3TMS,isomer #6	C[C@H](NC(=O)[C@H](CCC(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2184.8	Semi standard non polar	33892256
Glutamylalanine,3TMS,isomer #6	C[C@H](NC(=O)[C@H](CCC(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2137.2	Standard non polar	33892256
Glutamylalanine,3TMS,isomer #6	C[C@H](NC(=O)[C@H](CCC(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2726.3	Standard polar	33892256
Glutamylalanine,3TMS,isomer #7	C[C@@H](C(=O)O)N(C(=O)[C@H](CCC(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2192.2	Semi standard non polar	33892256
Glutamylalanine,3TMS,isomer #7	C[C@@H](C(=O)O)N(C(=O)[C@H](CCC(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2153.6	Standard non polar	33892256
Glutamylalanine,3TMS,isomer #7	C[C@@H](C(=O)O)N(C(=O)[C@H](CCC(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2784.3	Standard polar	33892256
Glutamylalanine,4TMS,isomer #1	C[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@H](CCC(=O)O[Si](C)(C)C)N[Si](C)(C)C)[Si](C)(C)C	2084.8	Semi standard non polar	33892256
Glutamylalanine,4TMS,isomer #1	C[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@H](CCC(=O)O[Si](C)(C)C)N[Si](C)(C)C)[Si](C)(C)C	2151.8	Standard non polar	33892256
Glutamylalanine,4TMS,isomer #1	C[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@H](CCC(=O)O[Si](C)(C)C)N[Si](C)(C)C)[Si](C)(C)C	2312.1	Standard polar	33892256
Glutamylalanine,4TMS,isomer #2	C[C@H](NC(=O)[C@H](CCC(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2204.0	Semi standard non polar	33892256
Glutamylalanine,4TMS,isomer #2	C[C@H](NC(=O)[C@H](CCC(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2197.5	Standard non polar	33892256
Glutamylalanine,4TMS,isomer #2	C[C@H](NC(=O)[C@H](CCC(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2461.1	Standard polar	33892256
Glutamylalanine,4TMS,isomer #3	C[C@@H](C(=O)O)N(C(=O)[C@H](CCC(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2218.3	Semi standard non polar	33892256
Glutamylalanine,4TMS,isomer #3	C[C@@H](C(=O)O)N(C(=O)[C@H](CCC(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2239.2	Standard non polar	33892256
Glutamylalanine,4TMS,isomer #3	C[C@@H](C(=O)O)N(C(=O)[C@H](CCC(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2546.4	Standard polar	33892256
Glutamylalanine,4TMS,isomer #4	C[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@H](CCC(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2238.5	Semi standard non polar	33892256
Glutamylalanine,4TMS,isomer #4	C[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@H](CCC(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2221.8	Standard non polar	33892256
Glutamylalanine,4TMS,isomer #4	C[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@H](CCC(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2426.0	Standard polar	33892256
Glutamylalanine,5TMS,isomer #1	C[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@H](CCC(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2269.9	Semi standard non polar	33892256
Glutamylalanine,5TMS,isomer #1	C[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@H](CCC(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2265.7	Standard non polar	33892256
Glutamylalanine,5TMS,isomer #1	C[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@H](CCC(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2234.8	Standard polar	33892256
Glutamylalanine,1TBDMS,isomer #1	C[C@H](NC(=O)[C@@H](N)CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	2240.3	Semi standard non polar	33892256
Glutamylalanine,1TBDMS,isomer #2	C[C@H](NC(=O)[C@@H](N)CCC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	2226.3	Semi standard non polar	33892256
Glutamylalanine,1TBDMS,isomer #3	C[C@H](NC(=O)[C@H](CCC(=O)O)N[Si](C)(C)C(C)(C)C)C(=O)O	2254.9	Semi standard non polar	33892256
Glutamylalanine,1TBDMS,isomer #4	C[C@@H](C(=O)O)N(C(=O)[C@@H](N)CCC(=O)O)[Si](C)(C)C(C)(C)C	2232.5	Semi standard non polar	33892256
Glutamylalanine,2TBDMS,isomer #1	C[C@H](NC(=O)[C@@H](N)CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2479.5	Semi standard non polar	33892256
Glutamylalanine,2TBDMS,isomer #2	C[C@H](NC(=O)[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)C(=O)O	2517.4	Semi standard non polar	33892256
Glutamylalanine,2TBDMS,isomer #3	C[C@@H](C(=O)O)N(C(=O)[C@@H](N)CCC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2480.4	Semi standard non polar	33892256
Glutamylalanine,2TBDMS,isomer #4	C[C@H](NC(=O)[C@H](CCC(=O)O)N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2499.6	Semi standard non polar	33892256
Glutamylalanine,2TBDMS,isomer #5	C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@@H](N)CCC(=O)O)[Si](C)(C)C(C)(C)C	2462.8	Semi standard non polar	33892256
Glutamylalanine,2TBDMS,isomer #6	C[C@@H](C(=O)O)N(C(=O)[C@H](CCC(=O)O)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2518.2	Semi standard non polar	33892256
Glutamylalanine,2TBDMS,isomer #7	C[C@H](NC(=O)[C@H](CCC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	2602.1	Semi standard non polar	33892256
Glutamylalanine,3TBDMS,isomer #1	C[C@H](NC(=O)[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2737.0	Semi standard non polar	33892256
Glutamylalanine,3TBDMS,isomer #1	C[C@H](NC(=O)[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2641.2	Standard non polar	33892256
Glutamylalanine,3TBDMS,isomer #1	C[C@H](NC(=O)[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2863.5	Standard polar	33892256
Glutamylalanine,3TBDMS,isomer #2	C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@@H](N)CCC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2688.2	Semi standard non polar	33892256
Glutamylalanine,3TBDMS,isomer #2	C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@@H](N)CCC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2668.7	Standard non polar	33892256
Glutamylalanine,3TBDMS,isomer #2	C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@@H](N)CCC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3096.9	Standard polar	33892256
Glutamylalanine,3TBDMS,isomer #3	C[C@@H](C(=O)O)N(C(=O)[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2765.9	Semi standard non polar	33892256
Glutamylalanine,3TBDMS,isomer #3	C[C@@H](C(=O)O)N(C(=O)[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2654.6	Standard non polar	33892256
Glutamylalanine,3TBDMS,isomer #3	C[C@@H](C(=O)O)N(C(=O)[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2893.5	Standard polar	33892256
Glutamylalanine,3TBDMS,isomer #4	C[C@H](NC(=O)[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	2888.8	Semi standard non polar	33892256
Glutamylalanine,3TBDMS,isomer #4	C[C@H](NC(=O)[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	2687.9	Standard non polar	33892256
Glutamylalanine,3TBDMS,isomer #4	C[C@H](NC(=O)[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	2975.0	Standard polar	33892256
Glutamylalanine,3TBDMS,isomer #5	C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@H](CCC(=O)O)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2744.9	Semi standard non polar	33892256
Glutamylalanine,3TBDMS,isomer #5	C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@H](CCC(=O)O)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2639.2	Standard non polar	33892256
Glutamylalanine,3TBDMS,isomer #5	C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@H](CCC(=O)O)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2836.7	Standard polar	33892256
Glutamylalanine,3TBDMS,isomer #6	C[C@H](NC(=O)[C@H](CCC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2857.9	Semi standard non polar	33892256
Glutamylalanine,3TBDMS,isomer #6	C[C@H](NC(=O)[C@H](CCC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2666.1	Standard non polar	33892256
Glutamylalanine,3TBDMS,isomer #6	C[C@H](NC(=O)[C@H](CCC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2888.9	Standard polar	33892256
Glutamylalanine,3TBDMS,isomer #7	C[C@@H](C(=O)O)N(C(=O)[C@H](CCC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2849.1	Semi standard non polar	33892256
Glutamylalanine,3TBDMS,isomer #7	C[C@@H](C(=O)O)N(C(=O)[C@H](CCC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2683.0	Standard non polar	33892256
Glutamylalanine,3TBDMS,isomer #7	C[C@@H](C(=O)O)N(C(=O)[C@H](CCC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2948.3	Standard polar	33892256
Glutamylalanine,4TBDMS,isomer #1	C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2954.3	Semi standard non polar	33892256
Glutamylalanine,4TBDMS,isomer #1	C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2853.4	Standard non polar	33892256
Glutamylalanine,4TBDMS,isomer #1	C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2773.8	Standard polar	33892256
Glutamylalanine,4TBDMS,isomer #2	C[C@H](NC(=O)[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3105.4	Semi standard non polar	33892256
Glutamylalanine,4TBDMS,isomer #2	C[C@H](NC(=O)[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2888.7	Standard non polar	33892256
Glutamylalanine,4TBDMS,isomer #2	C[C@H](NC(=O)[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2803.8	Standard polar	33892256
Glutamylalanine,4TBDMS,isomer #3	C[C@@H](C(=O)O)N(C(=O)[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3109.6	Semi standard non polar	33892256
Glutamylalanine,4TBDMS,isomer #3	C[C@@H](C(=O)O)N(C(=O)[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2919.3	Standard non polar	33892256
Glutamylalanine,4TBDMS,isomer #3	C[C@@H](C(=O)O)N(C(=O)[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2867.1	Standard polar	33892256
Glutamylalanine,4TBDMS,isomer #4	C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@H](CCC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3091.1	Semi standard non polar	33892256
Glutamylalanine,4TBDMS,isomer #4	C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@H](CCC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2901.6	Standard non polar	33892256
Glutamylalanine,4TBDMS,isomer #4	C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@H](CCC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2801.8	Standard polar	33892256
Glutamylalanine,5TBDMS,isomer #1	C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3333.8	Semi standard non polar	33892256
Glutamylalanine,5TBDMS,isomer #1	C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3102.6	Standard non polar	33892256
Glutamylalanine,5TBDMS,isomer #1	C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2777.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Glutamylalanine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamylalanine 10V, Positive-QTOF	splash10-0ue9-2890000000-c4ee77e01b7d1e1d3383	2018-11-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamylalanine 20V, Positive-QTOF	splash10-0f6x-9710000000-fed83af06726ad8e0fc9	2018-11-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamylalanine 40V, Positive-QTOF	splash10-0a4l-9000000000-f57412a046d4f71bc28e	2018-11-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamylalanine 10V, Negative-QTOF	splash10-014i-1790000000-2d05f958e7b0df336b72	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamylalanine 20V, Negative-QTOF	splash10-000i-9800000000-5337ff8f303b11c163a1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamylalanine 40V, Negative-QTOF	splash10-000f-9100000000-bec827e77d19d9072030	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamylalanine 10V, Positive-QTOF	splash10-0006-9310000000-5568c656cbd88eec1e21	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamylalanine 20V, Positive-QTOF	splash10-0f8i-9200000000-179a8f0ba0ceefc9c920	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamylalanine 40V, Positive-QTOF	splash10-0a4i-9100000000-578dc95b4dcb61269358	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB018687

KNApSAcK ID

Not Available

Chemspider ID

5360636

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6992506

PDB ID

Not Available

ChEBI ID

73849

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Sachs, Howard; Brand, Erwin. Optical rotation of peptides. VIII. Glutamic acid tripeptides. Journal of the American Chemical Society (1954), 76 1811-14.

Material Safety Data Sheet (MSDS)

Not Available

General References

King GF, Kuchel PW: Assimilation of alpha-glutamyl-peptides by human erythrocytes. A possible means of glutamate supply for glutathione synthesis. Biochem J. 1985 May 1;227(3):833-42. [PubMed:2860897 ]
Friedrichsen GM, Jakobsen P, Taub M, Begtrup M: Application of enzymatically stable dipeptides for enhancement of intestinal permeability. Synthesis and in vitro evaluation of dipeptide-coupled compounds. Bioorg Med Chem. 2001 Oct;9(10):2625-32. [PubMed:11557350 ]
Kanazawa A, Kakimoto Y, Nakajima T, Sano I: Identification of gamma-glutamylserine, gamma-glutamylalanine, gamma-glutamylvaline and S-methylglutathione of bovine brain. Biochim Biophys Acta. 1965 Nov 15;111(1):90-5. [PubMed:5867340 ]
Conway de Macario E, Macario AJ, Magarinos MC, Konig H, Kandler O: Dissecting the antigenic mosaic of the Archaebacterium Methanobacterium thermoautotrophicum by monoclonal antibodies of defined molecular specificity. Proc Natl Acad Sci U S A. 1983 Oct;80(20):6346-50. [PubMed:6194530 ]
Kondo H, Hashimoto M, Nagata K, Tomita K, Tsubota H: Assay of gamma-glutamyltransferase with amino acid dehydrogenases from Bacillus stearothermophilus as auxiliary enzymes. Clin Chim Acta. 1992 Apr 30;207(1-2):1-9. [PubMed:1350523 ]
Konig H, Kandler O, Jensen M, Rietschel ET: The primary structure of the glycan moiety of pseudomurein from Methanobacterium thermoautotrophicum. Hoppe Seylers Z Physiol Chem. 1983 Jun;364(6):627-36. [PubMed:6884989 ]
Fukuda M, Ogawa T, Sasaoka K: Optical configuration of -glutamylalanine in pea seedlings. Biochim Biophys Acta. 1973 Apr 28;304(2):363-6. [PubMed:4710763 ]

Showing metabocard for Glutamylalanine (HMDB0003764)

MOL for HMDB0003764 (Glutamylalanine)

3D MOL for HMDB0003764 (Glutamylalanine)

3D SDF for HMDB0003764 (Glutamylalanine)

3D-SDF for HMDB0003764 (Glutamylalanine)

PDB for HMDB0003764 (Glutamylalanine)

3D PDB for HMDB0003764 (Glutamylalanine)

SMILES for HMDB0003764 (Glutamylalanine)

INCHI for HMDB0003764 (Glutamylalanine)

Structure for HMDB0003764 (Glutamylalanine)

3D Structure for HMDB0003764 (Glutamylalanine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra