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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 21:02:39 UTC

Update Date

2021-09-14 15:37:04 UTC

HMDB ID

HMDB0028827

Secondary Accession Numbers

HMDB28827

Metabolite Identification

Common Name

Glutamylproline

Description

Glutamylproline is a dipeptide composed of 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. 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.

Structure

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

HMDB0028827
     RDKit          3D
Glutamylproline
 33 33  0  0  0  0  0  0  0  0999 V2000
    2.2762   -0.1173   -1.9664 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2470   -0.7284   -1.1711 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7725   -1.1338    0.1509 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3206   -0.0923    1.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4899    0.6563    0.6226 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1805    0.4774   -0.4018 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8879    1.7130    1.4808 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0579    0.1617   -1.1074 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1599    1.3041   -1.6325 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1746   -0.1868   -0.5014 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4188   -1.4694    0.1327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9595   -1.5874    0.0722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2935   -0.1479    0.4549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3487    0.6270   -0.4193 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0838    1.9887    0.1081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0781    2.7595    0.2009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8627    2.4665    0.4959 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0111    0.8671   -2.2673 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4876   -0.6326   -2.8532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9601   -1.6737   -1.7166 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0718   -1.7798    0.7373 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6411   -1.8433   -0.0713 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5437    0.6318    1.4046 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6179   -0.6315    2.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2732    2.5401    1.0584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2061   -1.4165    1.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9758   -2.3249   -0.3645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3350   -2.3083    0.7994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2920   -1.7381   -0.9631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0377   -0.0538    1.5400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3576    0.0814    0.2590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8002    0.6592   -1.4378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7748    2.9322    1.3895 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
  2  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 14 10  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
  7 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  6
 17 33  1  0
M  END


  Mrv1652304062013402D          

 17 17  0  0  0  0            999 V2000
 2500.7508 2500.4331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.0359 2500.8449    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2499.3148 2500.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.5998 2500.8573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.8787 2500.4577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.1638 2500.8694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2497.8787 2499.6322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2500.0359 2501.6704    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2501.4657 2500.8449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.1212 2499.5156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.8361 2499.1018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.1212 2500.3411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2500.7336 2499.5959    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2500.0662 2499.1109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3211 2498.3263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.1461 2498.3263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.4010 2499.1109    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
  2  8  1  6  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
 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>
HMDB0028827

> <DATABASE_NAME>
hmdb

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

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

> <INCHI_KEY>
YBTCBQBIJKGSJP-BQBZGAKWSA-N

> <FORMULA>
C10H16N2O5

> <MOLECULAR_WEIGHT>
244.247

> <EXACT_MASS>
244.105921623

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
23.613267525069777

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-3.20

> <JCHEM_LOGP>
-3.738591569758576

> <ALOGPS_LOGS>
-0.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.109796254781535

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2940542176131364

> <JCHEM_PKA_STRONGEST_BASIC>
8.442670147965806

> <JCHEM_POLAR_SURFACE_AREA>
120.92999999999999

> <JCHEM_REFRACTIVITY>
56.274200000000015

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.65e+01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0028827
     RDKit          3D
Glutamylproline
 33 33  0  0  0  0  0  0  0  0999 V2000
    2.2762   -0.1173   -1.9664 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2470   -0.7284   -1.1711 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7725   -1.1338    0.1509 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3206   -0.0923    1.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4899    0.6563    0.6226 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1805    0.4774   -0.4018 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8879    1.7130    1.4808 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0579    0.1617   -1.1074 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1599    1.3041   -1.6325 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1746   -0.1868   -0.5014 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4188   -1.4694    0.1327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9595   -1.5874    0.0722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2935   -0.1479    0.4549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3487    0.6270   -0.4193 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0838    1.9887    0.1081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0781    2.7595    0.2009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8627    2.4665    0.4959 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0111    0.8671   -2.2673 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4876   -0.6326   -2.8532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9601   -1.6737   -1.7166 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0718   -1.7798    0.7373 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6411   -1.8433   -0.0713 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5437    0.6318    1.4046 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6179   -0.6315    2.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2732    2.5401    1.0584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2061   -1.4165    1.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9758   -2.3249   -0.3645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3350   -2.3083    0.7994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2920   -1.7381   -0.9631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0377   -0.0538    1.5400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3576    0.0814    0.2590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8002    0.6592   -1.4378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7748    2.9322    1.3895 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
  2  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 14 10  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
  7 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  6
 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    4668.0684667.475   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    4666.7344668.244   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    4665.3884667.498   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    4664.0534668.267   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    4662.7074667.521   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0    4661.3724668.290   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    4662.7074665.980   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0    4666.7344669.785   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0    4669.4034668.244   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0    4670.6264665.762   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    4671.9614664.990   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0    4670.6264667.303   0.000  0.00  0.00           O+0
HETATM   13  N   UNK     0    4668.0364665.912   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0    4666.7904665.007   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    4667.2664663.542   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    4668.8064663.542   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    4669.2824665.007   0.000  0.00  0.00           C+0
CONECT    1    2    9   13                                                  
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                                                            
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    HMDB0028827
HETATM    1  N1  UNL     1       2.276  -0.117  -1.966  1.00  0.00           N  
HETATM    2  C1  UNL     1       1.247  -0.728  -1.171  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.773  -1.134   0.151  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.321  -0.092   1.044  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.490   0.656   0.623  1.00  0.00           C  
HETATM    6  O1  UNL     1       4.181   0.477  -0.402  1.00  0.00           O  
HETATM    7  O2  UNL     1       3.888   1.713   1.481  1.00  0.00           O  
HETATM    8  C5  UNL     1       0.058   0.162  -1.107  1.00  0.00           C  
HETATM    9  O3  UNL     1       0.160   1.304  -1.632  1.00  0.00           O  
HETATM   10  N2  UNL     1      -1.175  -0.187  -0.501  1.00  0.00           N  
HETATM   11  C6  UNL     1      -1.419  -1.469   0.133  1.00  0.00           C  
HETATM   12  C7  UNL     1      -2.960  -1.587   0.072  1.00  0.00           C  
HETATM   13  C8  UNL     1      -3.294  -0.148   0.455  1.00  0.00           C  
HETATM   14  C9  UNL     1      -2.349   0.627  -0.419  1.00  0.00           C  
HETATM   15  C10 UNL     1      -2.084   1.989   0.108  1.00  0.00           C  
HETATM   16  O4  UNL     1      -3.078   2.759   0.201  1.00  0.00           O  
HETATM   17  O5  UNL     1      -0.863   2.466   0.496  1.00  0.00           O  
HETATM   18  H1  UNL     1       2.011   0.867  -2.267  1.00  0.00           H  
HETATM   19  H2  UNL     1       2.488  -0.633  -2.853  1.00  0.00           H  
HETATM   20  H3  UNL     1       0.960  -1.674  -1.717  1.00  0.00           H  
HETATM   21  H4  UNL     1       1.072  -1.780   0.737  1.00  0.00           H  
HETATM   22  H5  UNL     1       2.641  -1.843  -0.071  1.00  0.00           H  
HETATM   23  H6  UNL     1       1.544   0.632   1.405  1.00  0.00           H  
HETATM   24  H7  UNL     1       2.618  -0.632   2.003  1.00  0.00           H  
HETATM   25  H8  UNL     1       4.273   2.540   1.058  1.00  0.00           H  
HETATM   26  H9  UNL     1      -1.206  -1.416   1.237  1.00  0.00           H  
HETATM   27  H10 UNL     1      -0.976  -2.325  -0.365  1.00  0.00           H  
HETATM   28  H11 UNL     1      -3.335  -2.308   0.799  1.00  0.00           H  
HETATM   29  H12 UNL     1      -3.292  -1.738  -0.963  1.00  0.00           H  
HETATM   30  H13 UNL     1      -3.038  -0.054   1.540  1.00  0.00           H  
HETATM   31  H14 UNL     1      -4.358   0.081   0.259  1.00  0.00           H  
HETATM   32  H15 UNL     1      -2.800   0.659  -1.438  1.00  0.00           H  
HETATM   33  H16 UNL     1      -0.775   2.932   1.389  1.00  0.00           H  
CONECT    1    2   18   19
CONECT    2    3    8   20
CONECT    3    4   21   22
CONECT    4    5   23   24
CONECT    5    6    6    7
CONECT    7   25
CONECT    8    9    9   10
CONECT   10   11   14
CONECT   11   12   26   27
CONECT   12   13   28   29
CONECT   13   14   30   31
CONECT   14   15   32
CONECT   15   16   16   17
CONECT   17   33
END

HMDB0028827
     RDKit          3D
Glutamylproline
 33 33  0  0  0  0  0  0  0  0999 V2000
    2.2762   -0.1173   -1.9664 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2470   -0.7284   -1.1711 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7725   -1.1338    0.1509 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3206   -0.0923    1.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4899    0.6563    0.6226 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1805    0.4774   -0.4018 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8879    1.7130    1.4808 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0579    0.1617   -1.1074 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1599    1.3041   -1.6325 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1746   -0.1868   -0.5014 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4188   -1.4694    0.1327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9595   -1.5874    0.0722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2935   -0.1479    0.4549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3487    0.6270   -0.4193 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0838    1.9887    0.1081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0781    2.7595    0.2009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8627    2.4665    0.4959 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0111    0.8671   -2.2673 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4876   -0.6326   -2.8532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9601   -1.6737   -1.7166 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0718   -1.7798    0.7373 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6411   -1.8433   -0.0713 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5437    0.6318    1.4046 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6179   -0.6315    2.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2732    2.5401    1.0584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2061   -1.4165    1.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9758   -2.3249   -0.3645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3350   -2.3083    0.7994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2920   -1.7381   -0.9631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0377   -0.0538    1.5400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3576    0.0814    0.2590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8002    0.6592   -1.4378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7748    2.9322    1.3895 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
  2  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 14 10  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
  7 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  6
 17 33  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
E-P	ChEBI
EP	ChEBI
L-Glu-L-pro	ChEBI
e-p Dipeptide	HMDB
EP dipeptide	HMDB
Glu-pro	HMDB
Glutamate proline dipeptide	HMDB
Glutamate-proline dipeptide	HMDB
L-Glutamyl-L-proline	HMDB
Α-glu-pro	HMDB
Α-L-glu-L-pro	HMDB
Α-glutamylproline	HMDB
Α-L-glutamyl-L-proline	HMDB
L-Α-glutamyl-L-proline	HMDB
alpha-Glu-pro	HMDB
alpha-L-Glu-L-pro	HMDB
alpha-Glutamylproline	HMDB
alpha-L-Glutamyl-L-proline	HMDB
L-alpha-Glutamyl-L-proline	HMDB
Glutamyl-proline	HMDB
Glutamic acid proline dipeptide	HMDB
Glutamic acid-proline dipeptide	HMDB
Glutamylproline	HMDB

Chemical Formula

C₁₀H₁₆N₂O₅

Average Molecular Weight

244.247

Monoisotopic Molecular Weight

244.105921623

IUPAC Name

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

Traditional Name

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

CAS Registry Number

41745-47-5

SMILES

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

InChI Identifier

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

InChI Key

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

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

dipeptide (CHEBI:73508 )

Ontology

Not Available

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
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)

Equine

Horse (FooDB: FOOD00378)

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)

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	-3.73	Extrapolated

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	97.9 g/L	ALOGPS
logP	-3.2	ALOGPS
logP	-3.7	ChemAxon
logS	-0.97	ALOGPS
pKa (Strongest Acidic)	3.29	ChemAxon
pKa (Strongest Basic)	8.44	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	23.61 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]+	158.406	30932474
DeepCCS	[M-H]-	156.048	30932474
DeepCCS	[M-2H]-	188.934	30932474
DeepCCS	[M+Na]+	164.499	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
Glutamylproline	N[C@@H](CCC(O)=O)C(=O)N1CCC[C@H]1C(O)=O	3255.2	Standard polar	33892256
Glutamylproline	N[C@@H](CCC(O)=O)C(=O)N1CCC[C@H]1C(O)=O	2184.5	Standard non polar	33892256
Glutamylproline	N[C@@H](CCC(O)=O)C(=O)N1CCC[C@H]1C(O)=O	2300.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Glutamylproline,1TMS,isomer #1	C[Si](C)(C)OC(=O)CC[C@H](N)C(=O)N1CCC[C@H]1C(=O)O	2218.4	Semi standard non polar	33892256
Glutamylproline,1TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@@H](N)CCC(=O)O	2192.8	Semi standard non polar	33892256
Glutamylproline,1TMS,isomer #3	C[Si](C)(C)N[C@@H](CCC(=O)O)C(=O)N1CCC[C@H]1C(=O)O	2246.9	Semi standard non polar	33892256
Glutamylproline,2TMS,isomer #1	C[Si](C)(C)OC(=O)CC[C@H](N)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	2231.2	Semi standard non polar	33892256
Glutamylproline,2TMS,isomer #2	C[Si](C)(C)N[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O	2262.2	Semi standard non polar	33892256
Glutamylproline,2TMS,isomer #3	C[Si](C)(C)N[C@@H](CCC(=O)O)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	2245.9	Semi standard non polar	33892256
Glutamylproline,2TMS,isomer #4	C[Si](C)(C)N([C@@H](CCC(=O)O)C(=O)N1CCC[C@H]1C(=O)O)[Si](C)(C)C	2368.2	Semi standard non polar	33892256
Glutamylproline,3TMS,isomer #1	C[Si](C)(C)N[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	2270.1	Semi standard non polar	33892256
Glutamylproline,3TMS,isomer #1	C[Si](C)(C)N[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	2336.0	Standard non polar	33892256
Glutamylproline,3TMS,isomer #2	C[Si](C)(C)OC(=O)CC[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2388.9	Semi standard non polar	33892256
Glutamylproline,3TMS,isomer #2	C[Si](C)(C)OC(=O)CC[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2377.1	Standard non polar	33892256
Glutamylproline,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@H](CCC(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2387.3	Semi standard non polar	33892256
Glutamylproline,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@H](CCC(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2364.9	Standard non polar	33892256
Glutamylproline,4TMS,isomer #1	C[Si](C)(C)OC(=O)CC[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2441.6	Semi standard non polar	33892256
Glutamylproline,4TMS,isomer #1	C[Si](C)(C)OC(=O)CC[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2407.4	Standard non polar	33892256
Glutamylproline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC[C@H](N)C(=O)N1CCC[C@H]1C(=O)O	2478.0	Semi standard non polar	33892256
Glutamylproline,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@@H](N)CCC(=O)O	2448.3	Semi standard non polar	33892256
Glutamylproline,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)O)C(=O)N1CCC[C@H]1C(=O)O	2494.5	Semi standard non polar	33892256
Glutamylproline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC[C@H](N)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	2692.8	Semi standard non polar	33892256
Glutamylproline,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O	2747.3	Semi standard non polar	33892256
Glutamylproline,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)O)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	2736.5	Semi standard non polar	33892256
Glutamylproline,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N([C@@H](CCC(=O)O)C(=O)N1CCC[C@H]1C(=O)O)[Si](C)(C)C(C)(C)C	2822.3	Semi standard non polar	33892256
Glutamylproline,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	2955.4	Semi standard non polar	33892256
Glutamylproline,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	2877.1	Standard non polar	33892256
Glutamylproline,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CC[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3089.8	Semi standard non polar	33892256
Glutamylproline,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CC[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2937.6	Standard non polar	33892256
Glutamylproline,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@H](CCC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3066.2	Semi standard non polar	33892256
Glutamylproline,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@H](CCC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2901.5	Standard non polar	33892256
Glutamylproline,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3312.0	Semi standard non polar	33892256
Glutamylproline,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3113.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 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 - Glutamylproline 10V, Positive-QTOF	splash10-004j-0290000000-d16857feda5a4823de9d	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamylproline 20V, Positive-QTOF	splash10-0fa2-6940000000-b7f91157a68d9fb1dd99	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamylproline 40V, Positive-QTOF	splash10-0aou-9200000000-73ff64e7d2a8a35ac556	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamylproline 10V, Negative-QTOF	splash10-0007-0690000000-f834be1f54a737d5176f	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamylproline 20V, Negative-QTOF	splash10-01rt-2930000000-7869ef082678b0019a02	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamylproline 40V, Negative-QTOF	splash10-08mi-9800000000-e8e5c97f369195c093fb	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamylproline 10V, Positive-QTOF	splash10-0002-0290000000-95e0403d7d0aba1af04c	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamylproline 20V, Positive-QTOF	splash10-00lr-9510000000-2193ae1f63be955d3510	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamylproline 40V, Positive-QTOF	splash10-05fr-9000000000-69c5865049770eec3514	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamylproline 10V, Negative-QTOF	splash10-0006-0390000000-9e627bb1f7ff8232af64	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamylproline 20V, Negative-QTOF	splash10-03di-4900000000-13c94e33e653daf7ce9c	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamylproline 40V, Negative-QTOF	splash10-03dj-9500000000-e8ef6624a8b520d9c1bc	2021-10-11	Wishart Lab	View Spectrum

NMR Spectra

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

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

FDB111869

KNApSAcK ID

Not Available

Chemspider ID

9393822

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11218768

PDB ID

Not Available

ChEBI ID

73508

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 Glutamylproline (HMDB0028827)

MOL for HMDB0028827 (Glutamylproline)

3D MOL for HMDB0028827 (Glutamylproline)

3D SDF for HMDB0028827 (Glutamylproline)

3D-SDF for HMDB0028827 (Glutamylproline)

PDB for HMDB0028827 (Glutamylproline)

3D PDB for HMDB0028827 (Glutamylproline)

SMILES for HMDB0028827 (Glutamylproline)

INCHI for HMDB0028827 (Glutamylproline)

Structure for HMDB0028827 (Glutamylproline)

3D Structure for HMDB0028827 (Glutamylproline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra