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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 21:03:55 UTC

Update Date

2021-09-14 15:36:53 UTC

HMDB ID

HMDB0029157

Secondary Accession Numbers

HMDB29157

Metabolite Identification

Common Name

gamma-Glutamylproline

Description

gamma-Glutamylproline is a dipeptide composed of gamma-glutamate and proline, 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-Glutamylproline 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-Glutamylproline is a biomarker for the consumption of beer.

Structure

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

HMDB0029157
     RDKit          3D
gamma-Glutamylproline
 33 33  0  0  0  0  0  0  0  0999 V2000
    3.2026   -2.1075   -0.5869 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5053   -0.6883   -0.7412 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2921    0.0304   -1.2944 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1025   -0.1048   -0.3800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0792    0.6010   -0.9290 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0478    1.1936   -2.0289 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3107    0.6038   -0.2309 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5228    1.2626   -0.6807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2868    1.6074    0.5714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4072    1.1107    1.7244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6494   -0.0150    1.0350 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5003   -1.2103    0.8297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8943   -1.8779    1.8187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8885   -1.6324   -0.4345 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8347   -0.1023    0.5815 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1276    1.1019    0.6954 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8183   -0.8961    1.7039 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6407   -2.1992    0.2763 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6183   -2.3892   -1.3964 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3447   -0.6079   -1.4541 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0451   -0.3668   -2.3108 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5640    1.0971   -1.4580 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3879    0.2986    0.6131 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8955   -1.1855   -0.2562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2979    2.1946   -1.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0855    0.5327   -1.2922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2768    1.0983    0.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4366    2.7028    0.6703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6836    1.8881    2.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0282    0.7413    2.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7431   -0.2498    1.6345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8413   -1.9653   -0.5296 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5048   -0.4664    2.5836 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
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
  2 15  1  0
 15 16  2  0
 15 17  1  0
 11  7  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  6
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  1
 14 32  1  0
 17 33  1  0
M  END


  Mrv1652304062014292D          

 17 17  0  0  0  0            999 V2000
 2500.7498 2500.5175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.0358 2500.9308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.3156 2500.5299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.6016 2500.9411    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2497.8814 2500.5421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.1674 2500.9533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2497.8814 2499.7176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2498.6016 2501.7656    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2501.4639 2500.9308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.1185 2499.4189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.8325 2499.0056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.1185 2500.2434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2500.7326 2499.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2500.0652 2499.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3201 2498.2304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.1451 2498.2304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.4000 2499.0150    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  9  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  8  1  1  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 13 14  1  0  0  0  0
 13 17  1  0  0  0  0
 17 10  1  6  0  0  0
  1 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029157

> <DATABASE_NAME>
hmdb

> <SMILES>
N[C@@H](CCC(=O)N1CCC[C@H]1C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H16N2O5/c11-6(9(14)15)3-4-8(13)12-5-1-2-7(12)10(16)17/h6-7H,1-5,11H2,(H,14,15)(H,16,17)/t6-,7-/m0/s1

> <INCHI_KEY>
VBCZKAGVUKCANO-BQBZGAKWSA-N

> <FORMULA>
C10H16N2O5

> <MOLECULAR_WEIGHT>
244.247

> <EXACT_MASS>
244.105921623

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
23.840227917590557

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-1-[(4S)-4-amino-4-carboxybutanoyl]pyrrolidine-2-carboxylic acid

> <ALOGPS_LOGP>
-3.17

> <JCHEM_LOGP>
-3.5438198413012794

> <ALOGPS_LOGS>
-0.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.834254589775786

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.9585787897976825

> <JCHEM_PKA_STRONGEST_BASIC>
9.312083570200985

> <JCHEM_POLAR_SURFACE_AREA>
120.92999999999999

> <JCHEM_REFRACTIVITY>
56.274200000000015

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.88e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-1-[(4S)-4-amino-4-carboxybutanoyl]pyrrolidine-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029157
     RDKit          3D
gamma-Glutamylproline
 33 33  0  0  0  0  0  0  0  0999 V2000
    3.2026   -2.1075   -0.5869 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5053   -0.6883   -0.7412 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2921    0.0304   -1.2944 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1025   -0.1048   -0.3800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0792    0.6010   -0.9290 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0478    1.1936   -2.0289 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3107    0.6038   -0.2309 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5228    1.2626   -0.6807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2868    1.6074    0.5714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4072    1.1107    1.7244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6494   -0.0150    1.0350 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5003   -1.2103    0.8297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8943   -1.8779    1.8187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8885   -1.6324   -0.4345 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8347   -0.1023    0.5815 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1276    1.1019    0.6954 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8183   -0.8961    1.7039 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6407   -2.1992    0.2763 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6183   -2.3892   -1.3964 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3447   -0.6079   -1.4541 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0451   -0.3668   -2.3108 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5640    1.0971   -1.4580 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3879    0.2986    0.6131 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8955   -1.1855   -0.2562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2979    2.1946   -1.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0855    0.5327   -1.2922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2768    1.0983    0.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4366    2.7028    0.6703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6836    1.8881    2.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0282    0.7413    2.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7431   -0.2498    1.6345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8413   -1.9653   -0.5296 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5048   -0.4664    2.5836 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
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
  2 15  1  0
 15 16  2  0
 15 17  1  0
 11  7  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  6
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  1
 14 32  1  0
 17 33  1  0
M  END

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  C   UNK     0    4668.0664667.633   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    4666.7334668.404   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    4665.3894667.656   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    4664.0564668.423   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    4662.7124667.679   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0    4661.3794668.446   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    4662.7124666.140   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0    4664.0564669.962   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0    4669.3994668.404   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0    4670.6214665.582   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    4671.9544664.810   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0    4670.6214667.121   0.000  0.00  0.00           O+0
HETATM   13  N   UNK     0    4668.0344665.733   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0    4666.7884664.828   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    4667.2644663.363   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    4668.8044663.363   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    4669.2804664.828   0.000  0.00  0.00           C+0
CONECT    1    2    9   13                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    4                                                            
CONECT    9    1                                                            
CONECT   10   11   12   17                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   14   17    1                                                  
CONECT   14   15   13                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   13   10                                                  
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0029157
HETATM    1  N1  UNL     1       3.203  -2.107  -0.587  1.00  0.00           N  
HETATM    2  C1  UNL     1       3.505  -0.688  -0.741  1.00  0.00           C  
HETATM    3  C2  UNL     1       2.292   0.030  -1.294  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.103  -0.105  -0.380  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.079   0.601  -0.929  1.00  0.00           C  
HETATM    6  O1  UNL     1       0.048   1.194  -2.029  1.00  0.00           O  
HETATM    7  N2  UNL     1      -1.311   0.604  -0.231  1.00  0.00           N  
HETATM    8  C5  UNL     1      -2.523   1.263  -0.681  1.00  0.00           C  
HETATM    9  C6  UNL     1      -3.287   1.607   0.571  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.407   1.111   1.724  1.00  0.00           C  
HETATM   11  C8  UNL     1      -1.649  -0.015   1.035  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.500  -1.210   0.830  1.00  0.00           C  
HETATM   13  O2  UNL     1      -2.894  -1.878   1.819  1.00  0.00           O  
HETATM   14  O3  UNL     1      -2.888  -1.632  -0.434  1.00  0.00           O  
HETATM   15  C10 UNL     1       3.835  -0.102   0.582  1.00  0.00           C  
HETATM   16  O4  UNL     1       4.128   1.102   0.695  1.00  0.00           O  
HETATM   17  O5  UNL     1       3.818  -0.896   1.704  1.00  0.00           O  
HETATM   18  H1  UNL     1       2.641  -2.199   0.276  1.00  0.00           H  
HETATM   19  H2  UNL     1       2.618  -2.389  -1.396  1.00  0.00           H  
HETATM   20  H3  UNL     1       4.345  -0.608  -1.454  1.00  0.00           H  
HETATM   21  H4  UNL     1       2.045  -0.367  -2.311  1.00  0.00           H  
HETATM   22  H5  UNL     1       2.564   1.097  -1.458  1.00  0.00           H  
HETATM   23  H6  UNL     1       1.388   0.299   0.613  1.00  0.00           H  
HETATM   24  H7  UNL     1       0.895  -1.186  -0.256  1.00  0.00           H  
HETATM   25  H8  UNL     1      -2.298   2.195  -1.238  1.00  0.00           H  
HETATM   26  H9  UNL     1      -3.085   0.533  -1.292  1.00  0.00           H  
HETATM   27  H10 UNL     1      -4.277   1.098   0.597  1.00  0.00           H  
HETATM   28  H11 UNL     1      -3.437   2.703   0.670  1.00  0.00           H  
HETATM   29  H12 UNL     1      -1.684   1.888   2.005  1.00  0.00           H  
HETATM   30  H13 UNL     1      -3.028   0.741   2.554  1.00  0.00           H  
HETATM   31  H14 UNL     1      -0.743  -0.250   1.635  1.00  0.00           H  
HETATM   32  H15 UNL     1      -3.841  -1.965  -0.530  1.00  0.00           H  
HETATM   33  H16 UNL     1       3.505  -0.466   2.584  1.00  0.00           H  
CONECT    1    2   18   19
CONECT    2    3   15   20
CONECT    3    4   21   22
CONECT    4    5   23   24
CONECT    5    6    6    7
CONECT    7    8   11
CONECT    8    9   25   26
CONECT    9   10   27   28
CONECT   10   11   29   30
CONECT   11   12   31
CONECT   12   13   13   14
CONECT   14   32
CONECT   15   16   16   17
CONECT   17   33
END

HMDB0029157
     RDKit          3D
gamma-Glutamylproline
 33 33  0  0  0  0  0  0  0  0999 V2000
    3.2026   -2.1075   -0.5869 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5053   -0.6883   -0.7412 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2921    0.0304   -1.2944 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1025   -0.1048   -0.3800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0792    0.6010   -0.9290 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0478    1.1936   -2.0289 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3107    0.6038   -0.2309 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5228    1.2626   -0.6807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2868    1.6074    0.5714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4072    1.1107    1.7244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6494   -0.0150    1.0350 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5003   -1.2103    0.8297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8943   -1.8779    1.8187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8885   -1.6324   -0.4345 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8347   -0.1023    0.5815 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1276    1.1019    0.6954 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8183   -0.8961    1.7039 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6407   -2.1992    0.2763 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6183   -2.3892   -1.3964 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3447   -0.6079   -1.4541 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0451   -0.3668   -2.3108 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5640    1.0971   -1.4580 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3879    0.2986    0.6131 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8955   -1.1855   -0.2562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2979    2.1946   -1.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0855    0.5327   -1.2922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2768    1.0983    0.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4366    2.7028    0.6703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6836    1.8881    2.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0282    0.7413    2.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7431   -0.2498    1.6345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8413   -1.9653   -0.5296 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5048   -0.4664    2.5836 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
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
  2 15  1  0
 15 16  2  0
 15 17  1  0
 11  7  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  6
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  1
 14 32  1  0
 17 33  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
g-Glutamylproline	Generator
Γ-glutamylproline	Generator
gamma-Glutamate proline dipeptide	HMDB
gamma-Glutamate-proline dipeptide	HMDB
GE-p dipeptide	HMDB
GEP dipeptide	HMDB
GGlu-pro	HMDB
L-gamma-Glutamyl-L-proline	HMDB
Γ-glu-pro	HMDB
Γ-L-glu-L-pro	HMDB
Γ-L-glutamyl-L-proline	HMDB
L-Γ-glutamyl-L-proline	HMDB
gamma-Glu-pro	HMDB
gamma-L-Glu-L-pro	HMDB
gamma-L-Glutamyl-L-proline	HMDB
(2S)-1-[(4S)-4-Amino-4-carboxybutanoyl]pyrrolidine-2-carboxylate	HMDB
gamma-Glutamylproline	HMDB

Chemical Formula

C₁₀H₁₆N₂O₅

Average Molecular Weight

244.247

Monoisotopic Molecular Weight

244.105921623

IUPAC Name

(2S)-1-[(4S)-4-amino-4-carboxybutanoyl]pyrrolidine-2-carboxylic acid

Traditional Name

(2S)-1-[(4S)-4-amino-4-carboxybutanoyl]pyrrolidine-2-carboxylic acid

CAS Registry Number

53411-63-5

SMILES

N[C@@H](CCC(=O)N1CCC[C@H]1C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C10H16N2O5/c11-6(9(14)15)3-4-8(13)12-5-1-2-7(12)10(16)17/h6-7H,1-5,11H2,(H,14,15)(H,16,17)/t6-,7-/m0/s1

InChI Key

VBCZKAGVUKCANO-BQBZGAKWSA-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-alpha-amino acid
N-acyl-alpha amino acid or derivatives
N-acyl-l-alpha-amino acid
Proline or derivatives
Alpha-amino acid or derivatives
L-alpha-amino acid
Alpha-amino acid
N-acylpyrrolidine
Pyrrolidine carboxylic acid
Pyrrolidine carboxylic acid or derivatives
Heterocyclic fatty acid
Dicarboxylic acid or derivatives
Fatty acyl
Fatty acid
Tertiary carboxylic acid amide
Pyrrolidine
Amino acid
Amino acid or derivatives
Carboxamide group
Organoheterocyclic compound
Carboxylic acid
Azacycle
Amine
Primary aliphatic amine
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Primary amine
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

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	-4.4	Extrapolated

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	21.9 g/L	ALOGPS
logP	-3.2	ALOGPS
logP	-3.5	ChemAxon
logS	-0.93	ALOGPS
pKa (Strongest Acidic)	1.96	ChemAxon
pKa (Strongest Basic)	9.31	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	120.93 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	56.27 m³·mol⁻¹	ChemAxon
Polarizability	23.84 Å³	ChemAxon
Number of Rings	1	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]+	154.987	30932474
DeepCCS	[M-H]-	152.629	30932474
DeepCCS	[M-2H]-	185.571	30932474
DeepCCS	[M+Na]+	161.08	30932474
AllCCS	[M+H]+	152.8	32859911
AllCCS	[M+H-H2O]+	149.4	32859911
AllCCS	[M+NH4]+	156.0	32859911
AllCCS	[M+Na]+	156.9	32859911
AllCCS	[M-H]-	153.7	32859911
AllCCS	[M+Na-2H]-	153.9	32859911
AllCCS	[M+HCOO]-	154.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
gamma-Glutamylproline	N[C@@H](CCC(=O)N1CCC[C@H]1C(O)=O)C(O)=O	3204.6	Standard polar	33892256
gamma-Glutamylproline	N[C@@H](CCC(=O)N1CCC[C@H]1C(O)=O)C(O)=O	2194.3	Standard non polar	33892256
gamma-Glutamylproline	N[C@@H](CCC(=O)N1CCC[C@H]1C(O)=O)C(O)=O	2480.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
gamma-Glutamylproline,1TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)CC[C@H](N)C(=O)O	2232.7	Semi standard non polar	33892256
gamma-Glutamylproline,1TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H](N)CCC(=O)N1CCC[C@H]1C(=O)O	2204.9	Semi standard non polar	33892256
gamma-Glutamylproline,1TMS,isomer #3	C[Si](C)(C)N[C@@H](CCC(=O)N1CCC[C@H]1C(=O)O)C(=O)O	2245.8	Semi standard non polar	33892256
gamma-Glutamylproline,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](N)CCC(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	2243.2	Semi standard non polar	33892256
gamma-Glutamylproline,2TMS,isomer #2	C[Si](C)(C)N[C@@H](CCC(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C)C(=O)O	2265.1	Semi standard non polar	33892256
gamma-Glutamylproline,2TMS,isomer #3	C[Si](C)(C)N[C@@H](CCC(=O)N1CCC[C@H]1C(=O)O)C(=O)O[Si](C)(C)C	2241.6	Semi standard non polar	33892256
gamma-Glutamylproline,2TMS,isomer #4	C[Si](C)(C)N([C@@H](CCC(=O)N1CCC[C@H]1C(=O)O)C(=O)O)[Si](C)(C)C	2317.2	Semi standard non polar	33892256
gamma-Glutamylproline,3TMS,isomer #1	C[Si](C)(C)N[C@@H](CCC(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2272.4	Semi standard non polar	33892256
gamma-Glutamylproline,3TMS,isomer #1	C[Si](C)(C)N[C@@H](CCC(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2326.9	Standard non polar	33892256
gamma-Glutamylproline,3TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2385.5	Semi standard non polar	33892256
gamma-Glutamylproline,3TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2386.9	Standard non polar	33892256
gamma-Glutamylproline,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](CCC(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2370.9	Semi standard non polar	33892256
gamma-Glutamylproline,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](CCC(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2374.5	Standard non polar	33892256
gamma-Glutamylproline,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)CC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2447.5	Semi standard non polar	33892256
gamma-Glutamylproline,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)CC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2418.5	Standard non polar	33892256
gamma-Glutamylproline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)CC[C@H](N)C(=O)O	2474.4	Semi standard non polar	33892256
gamma-Glutamylproline,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCC(=O)N1CCC[C@H]1C(=O)O	2455.7	Semi standard non polar	33892256
gamma-Glutamylproline,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)N1CCC[C@H]1C(=O)O)C(=O)O	2486.1	Semi standard non polar	33892256
gamma-Glutamylproline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCC(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	2693.6	Semi standard non polar	33892256
gamma-Glutamylproline,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	2729.9	Semi standard non polar	33892256
gamma-Glutamylproline,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)N1CCC[C@H]1C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	2704.6	Semi standard non polar	33892256
gamma-Glutamylproline,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N([C@@H](CCC(=O)N1CCC[C@H]1C(=O)O)C(=O)O)[Si](C)(C)C(C)(C)C	2802.6	Semi standard non polar	33892256
gamma-Glutamylproline,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2959.9	Semi standard non polar	33892256
gamma-Glutamylproline,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2901.6	Standard non polar	33892256
gamma-Glutamylproline,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3060.2	Semi standard non polar	33892256
gamma-Glutamylproline,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2966.7	Standard non polar	33892256
gamma-Glutamylproline,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCC(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3055.6	Semi standard non polar	33892256
gamma-Glutamylproline,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCC(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2974.4	Standard non polar	33892256
gamma-Glutamylproline,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)CC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3316.9	Semi standard non polar	33892256
gamma-Glutamylproline,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)CC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3156.2	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Glutamylproline 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 - gamma-Glutamylproline 10V, Positive-QTOF	splash10-002b-0980000000-8a1cd401fdb5e05dd9c8	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamylproline 20V, Positive-QTOF	splash10-000t-2910000000-b827663230992302012d	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamylproline 40V, Positive-QTOF	splash10-066r-9400000000-fbe9d16e1bcb25bc2314	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamylproline 10V, Negative-QTOF	splash10-0007-0690000000-4f6df51ff93ddee6f5c7	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamylproline 20V, Negative-QTOF	splash10-0032-2930000000-e0c1993d7d7ea2720576	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamylproline 40V, Negative-QTOF	splash10-02ml-9400000000-20d089c4dc42b36eee9e	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamylproline 10V, Negative-QTOF	splash10-01t9-0790000000-b918b6e73b394134ef36	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamylproline 20V, Negative-QTOF	splash10-03di-2910000000-b6e1f2141ad7e0653126	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamylproline 40V, Negative-QTOF	splash10-03dm-9500000000-3f3c6b45a991e5971112	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamylproline 10V, Positive-QTOF	splash10-00kb-4980000000-a28aaafe8c838eb13225	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamylproline 20V, Positive-QTOF	splash10-00sj-9800000000-07e1a802fb693b887835	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamylproline 40V, Positive-QTOF	splash10-05gi-9200000000-cb00f3642cff0cc1c1c5	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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

FDB112149

KNApSAcK ID

Not Available

Chemspider ID

8031942

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9856242

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for gamma-Glutamylproline (HMDB0029157)

MOL for HMDB0029157 (gamma-Glutamylproline)

3D MOL for HMDB0029157 (gamma-Glutamylproline)

3D SDF for HMDB0029157 (gamma-Glutamylproline)

3D-SDF for HMDB0029157 (gamma-Glutamylproline)

PDB for HMDB0029157 (gamma-Glutamylproline)

3D PDB for HMDB0029157 (gamma-Glutamylproline)

SMILES for HMDB0029157 (gamma-Glutamylproline)

INCHI for HMDB0029157 (gamma-Glutamylproline)

Structure for HMDB0029157 (gamma-Glutamylproline)

3D Structure for HMDB0029157 (gamma-Glutamylproline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra