MiMeDB: Showing metabocard for gamma-Glutamylvaline (MMDBc0000447)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:37:58 UTC

Update Date

2024-04-30 19:32:26 UTC

Metabolite ID

MMDBc0000447

Metabolite Identification

Common Name

gamma-Glutamylvaline

Description

gamma-Glutamylvaline is a dipeptide composed of gamma-glutamate and valine. It 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-Glutamylvaline 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. It is found in urine (PMID: 3782411 ).

Structure

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

HMDB0011172
     RDKit          3D
gamma-Glutamylvaline
 35 34  0  0  0  0  0  0  0  0999 V2000
   -4.1766    0.7663    1.2690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9464    0.6934    0.4202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3691    0.5974   -1.0330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0654   -0.4869    0.7778 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9037   -0.5121   -0.0615 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4233   -0.3346    0.3953 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7050   -0.1352    1.6020 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5516   -0.3805   -0.5667 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8339   -0.1659    0.1678 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0445   -0.2085   -0.7330 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1935    0.0172    0.1684 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9930    0.8309   -1.7684 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1677    0.8535   -2.6906 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9240    1.8672   -1.7286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8113   -1.7571    0.7834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4483   -2.7698    0.1045 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9664   -1.9398    1.5319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6133    1.7961    1.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9838    0.6655    2.3349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9571    0.0727    0.8750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4050    1.6541    0.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3228   -0.4563   -1.3952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7165    1.2216   -1.6553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4212    0.9351   -1.1401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7154   -0.3059    1.8199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0578   -0.6733   -1.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5287   -1.3530   -1.1029 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3770    0.4468   -1.3130 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0029   -0.9222    0.9643 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8214    0.8185    0.7039 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1658   -1.2318   -1.1537 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9480    0.8720    0.7110 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1910   -0.7969    0.8116 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8724    1.6744   -2.0294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8638   -2.5404    2.3599 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 12 14  1  0
  4 15  1  0
 15 16  2  0
 15 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  1
  5 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  6
 11 32  1  0
 11 33  1  0
 14 34  1  0
 17 35  1  0
M  END


  Mrv1652312091700132D          

 17 16  0  0  0  0            999 V2000
 2498.5332 2500.3216    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2499.2483 2500.7333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2499.9632 2500.3216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.6780 2500.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.3929 2500.3216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.1079 2500.7333    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2502.8229 2500.3216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.5376 2500.7333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.8229 2499.4960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.1079 2501.5589    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2499.9632 2499.4960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2497.8183 2500.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.1035 2500.3216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.8183 2501.5589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.5332 2499.4960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.8183 2499.0822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2499.2483 2499.0822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 12  1  0  0  0  0
  1 15  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 11  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 10  1  6  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000447

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H18N2O5/c1-5(2)8(10(16)17)12-7(13)4-3-6(11)9(14)15/h5-6,8H,3-4,11H2,1-2H3,(H,12,13)(H,14,15)(H,16,17)/t6-,8-/m0/s1

> <INCHI_KEY>
AQAKHZVPOOGUCK-XPUUQOCRSA-N

> <FORMULA>
C10H18N2O5

> <MOLECULAR_WEIGHT>
246.263

> <EXACT_MASS>
246.121571688

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
24.50498750960178

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-2.90

> <JCHEM_LOGP>
-2.9243099728125683

> <ALOGPS_LOGS>
-1.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.970808482539323

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.0944816010323675

> <JCHEM_PKA_STRONGEST_BASIC>
9.312075794574314

> <JCHEM_POLAR_SURFACE_AREA>
129.72

> <JCHEM_REFRACTIVITY>
57.5807

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.02e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-amino-4-{[(1S)-1-carboxy-2-methylpropyl]carbamoyl}butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0011172
     RDKit          3D
gamma-Glutamylvaline
 35 34  0  0  0  0  0  0  0  0999 V2000
   -4.1766    0.7663    1.2690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9464    0.6934    0.4202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3691    0.5974   -1.0330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0654   -0.4869    0.7778 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9037   -0.5121   -0.0615 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4233   -0.3346    0.3953 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7050   -0.1352    1.6020 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5516   -0.3805   -0.5667 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8339   -0.1659    0.1678 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0445   -0.2085   -0.7330 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1935    0.0172    0.1684 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9930    0.8309   -1.7684 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1677    0.8535   -2.6906 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9240    1.8672   -1.7286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8113   -1.7571    0.7834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4483   -2.7698    0.1045 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9664   -1.9398    1.5319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6133    1.7961    1.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9838    0.6655    2.3349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9571    0.0727    0.8750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4050    1.6541    0.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3228   -0.4563   -1.3952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7165    1.2216   -1.6553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4212    0.9351   -1.1401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7154   -0.3059    1.8199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0578   -0.6733   -1.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5287   -1.3530   -1.1029 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3770    0.4468   -1.3130 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0029   -0.9222    0.9643 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8214    0.8185    0.7039 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1658   -1.2318   -1.1537 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9480    0.8720    0.7110 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1910   -0.7969    0.8116 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8724    1.6744   -2.0294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8638   -2.5404    2.3599 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 12 14  1  0
  4 15  1  0
 15 16  2  0
 15 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  1
  5 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  6
 11 32  1  0
 11 33  1  0
 14 34  1  0
 17 35  1  0
M  END

HEADER    PROTEIN                                 09-DEC-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-DEC-17         0                                  
HETATM    1  C   UNK     0    4663.9294667.267   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    4665.2644668.036   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0    4666.5984667.267   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    4667.9324668.036   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    4669.2674667.267   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    4670.6014668.036   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    4671.9364667.267   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    4673.2704668.036   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    4671.9364665.726   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0    4670.6014669.577   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0    4666.5984665.726   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    4662.5944668.036   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    4661.2604667.267   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    4662.5944669.577   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    4663.9294665.726   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0    4662.5944664.953   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0    4665.2644664.953   0.000  0.00  0.00           O+0
CONECT    1    2   12   15                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    6                                                            
CONECT   11    3                                                            
CONECT   12    1   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    1   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

COMPND    HMDB0011172
HETATM    1  C1  UNL     1      -4.177   0.766   1.269  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.946   0.693   0.420  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.369   0.597  -1.033  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.065  -0.487   0.778  1.00  0.00           C  
HETATM    5  N1  UNL     1      -0.904  -0.512  -0.061  1.00  0.00           N  
HETATM    6  C5  UNL     1       0.423  -0.335   0.395  1.00  0.00           C  
HETATM    7  O1  UNL     1       0.705  -0.135   1.602  1.00  0.00           O  
HETATM    8  C6  UNL     1       1.552  -0.381  -0.567  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.834  -0.166   0.168  1.00  0.00           C  
HETATM   10  C8  UNL     1       4.044  -0.208  -0.733  1.00  0.00           C  
HETATM   11  N2  UNL     1       5.194   0.017   0.168  1.00  0.00           N  
HETATM   12  C9  UNL     1       3.993   0.831  -1.768  1.00  0.00           C  
HETATM   13  O2  UNL     1       3.168   0.853  -2.691  1.00  0.00           O  
HETATM   14  O3  UNL     1       4.924   1.867  -1.729  1.00  0.00           O  
HETATM   15  C10 UNL     1      -2.811  -1.757   0.783  1.00  0.00           C  
HETATM   16  O4  UNL     1      -2.448  -2.770   0.105  1.00  0.00           O  
HETATM   17  O5  UNL     1      -3.966  -1.940   1.532  1.00  0.00           O  
HETATM   18  H1  UNL     1      -4.613   1.796   1.114  1.00  0.00           H  
HETATM   19  H2  UNL     1      -3.984   0.666   2.335  1.00  0.00           H  
HETATM   20  H3  UNL     1      -4.957   0.073   0.875  1.00  0.00           H  
HETATM   21  H4  UNL     1      -2.405   1.654   0.536  1.00  0.00           H  
HETATM   22  H5  UNL     1      -3.323  -0.456  -1.395  1.00  0.00           H  
HETATM   23  H6  UNL     1      -2.716   1.222  -1.655  1.00  0.00           H  
HETATM   24  H7  UNL     1      -4.421   0.935  -1.140  1.00  0.00           H  
HETATM   25  H8  UNL     1      -1.715  -0.306   1.820  1.00  0.00           H  
HETATM   26  H9  UNL     1      -1.058  -0.673  -1.079  1.00  0.00           H  
HETATM   27  H10 UNL     1       1.529  -1.353  -1.103  1.00  0.00           H  
HETATM   28  H11 UNL     1       1.377   0.447  -1.313  1.00  0.00           H  
HETATM   29  H12 UNL     1       3.003  -0.922   0.964  1.00  0.00           H  
HETATM   30  H13 UNL     1       2.821   0.818   0.704  1.00  0.00           H  
HETATM   31  H14 UNL     1       4.166  -1.232  -1.154  1.00  0.00           H  
HETATM   32  H15 UNL     1       4.948   0.872   0.711  1.00  0.00           H  
HETATM   33  H16 UNL     1       5.191  -0.797   0.812  1.00  0.00           H  
HETATM   34  H17 UNL     1       5.872   1.674  -2.029  1.00  0.00           H  
HETATM   35  H18 UNL     1      -3.864  -2.540   2.360  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    4   21
CONECT    3   22   23   24
CONECT    4    5   15   25
CONECT    5    6   26
CONECT    6    7    7    8
CONECT    8    9   27   28
CONECT    9   10   29   30
CONECT   10   11   12   31
CONECT   11   32   33
CONECT   12   13   13   14
CONECT   14   34
CONECT   15   16   16   17
CONECT   17   35
END

HMDB0011172
     RDKit          3D
gamma-Glutamylvaline
 35 34  0  0  0  0  0  0  0  0999 V2000
   -4.1766    0.7663    1.2690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9464    0.6934    0.4202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3691    0.5974   -1.0330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0654   -0.4869    0.7778 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9037   -0.5121   -0.0615 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4233   -0.3346    0.3953 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7050   -0.1352    1.6020 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5516   -0.3805   -0.5667 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8339   -0.1659    0.1678 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0445   -0.2085   -0.7330 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1935    0.0172    0.1684 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9930    0.8309   -1.7684 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1677    0.8535   -2.6906 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9240    1.8672   -1.7286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8113   -1.7571    0.7834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4483   -2.7698    0.1045 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9664   -1.9398    1.5319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6133    1.7961    1.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9838    0.6655    2.3349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9571    0.0727    0.8750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4050    1.6541    0.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3228   -0.4563   -1.3952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7165    1.2216   -1.6553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4212    0.9351   -1.1401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7154   -0.3059    1.8199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0578   -0.6733   -1.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5287   -1.3530   -1.1029 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3770    0.4468   -1.3130 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0029   -0.9222    0.9643 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8214    0.8185    0.7039 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1658   -1.2318   -1.1537 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9480    0.8720    0.7110 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1910   -0.7969    0.8116 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8724    1.6744   -2.0294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8638   -2.5404    2.3599 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 12 14  1  0
  4 15  1  0
 15 16  2  0
 15 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  1
  5 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  6
 11 32  1  0
 11 33  1  0
 14 34  1  0
 17 35  1  0
M  END

Synonyms

Value	Source
L-gamma-Glu-L-val	ChEBI
L-g-Glu-L-val	Generator
L-Γ-glu-L-val	Generator
g-Glutamylvaline	Generator
Γ-glutamylvaline	Generator
Γ-glu-val	HMDB
Γ-L-glu-L-val	HMDB
Γ-L-glutamyl-L-valine	HMDB
L-Γ-glutamyl-L-valine	HMDB
N-Γ-glutamylvaline	HMDB
N-L-Γ-glutamylvaline	HMDB
N-L-Γ-glutamyl-L-valine	HMDB
gamma-Glu-val	HMDB
gamma-L-Glu-L-val	HMDB
gamma-L-Glutamyl-L-valine	HMDB
L-gamma-Glutamyl-L-valine	HMDB
N-L-gamma-Glutamylvaline	HMDB
N-L-gamma-Glutamyl-L-valine	HMDB
g-Glu-val	HMDB
N-Γ-L-glutamyl-L-valine	HMDB
N-gamma-Glutamylvaline	HMDB
N-gamma-L-Glutamyl-L-valine	HMDB
gamma-Glutamylvaline	HMDB, ChEBI

Molecular Formula

C₁₀H₁₈N₂O₅

Average Mass

246.263

Monoisotopic Mass

246.121571688

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C10H18N2O5/c1-5(2)8(10(16)17)12-7(13)4-3-6(11)9(14)15/h5-6,8H,3-4,11H2,1-2H3,(H,12,13)(H,14,15)(H,16,17)/t6-,8-/m0/s1

InChI Key

AQAKHZVPOOGUCK-XPUUQOCRSA-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
Valine or derivatives
Alpha-amino acid
Alpha-amino acid or derivatives
L-alpha-amino acid
Methyl-branched fatty acid
Branched fatty acid
N-acyl-amine
Fatty acyl
Fatty acid
Dicarboxylic acid or derivatives
Fatty amide
Secondary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Amino acid
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

glutamyl-L-amino acid (CHEBI:68848 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	9.02 g/L	ALOGPS
logP	-2.9	ALOGPS
logP	-2.9	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	2.09	ChemAxon
pKa (Strongest Basic)	9.31	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	129.72 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	57.58 m³·mol⁻¹	ChemAxon
Polarizability	24.5 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ugj-0490000000-570014eb4534edfce899	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-107i-5940000000-8fdd03caafd389b6e73b	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9400000000-8ab7d89b0c6e2e1eff17	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0f6t-0190000000-01f7213e4f145c229f03	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fvj-3980000000-fd64f03e4003670f690f	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00xr-9400000000-30468bbfca4ce7249b34	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f9t-0390000000-b98dfd57b7b1a257fc10	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-7920000000-064bf60d4c9ec4495c11	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9300000000-192d8f0f004814ab26da	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0490000000-68e7fb2a1019db29bb38	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-2900000000-dec09fec1abcc84b0da3	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9300000000-7d72f0bd5bf88c1a02a8	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces
Placenta

Tissue Locations

Placenta

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

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

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	5	Human feces; Human sputum; Human ; Human subgingival plaque; Human saliva; Human stool	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Bacteroidetes	1	Human feces; Human stool; Human	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Host Biospecimen and Location

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

External Links

HMDB ID

HMDB0011172

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5378716

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7015683

PDB ID

Not Available

ChEBI ID

68848

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Jandke J, Spiteller G: Dipeptide analysis in human urine. J Chromatogr. 1986 Oct 31;382:39-45. doi: 10.1016/s0378-4347(00)83502-1. [PubMed:3782411 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for gamma-Glutamylvaline (MMDBc0000447)

MOL for #<Metabolite:0x00007fdb719b4b88>

3D MOL for #<Metabolite:0x00007fdb719b4b88>

3D SDF for #<Metabolite:0x00007fdb719b4b88>

3D-SDF for #<Metabolite:0x00007fdb719b4b88>

PDB for #<Metabolite:0x00007fdb719b4b88>

3D PDB for #<Metabolite:0x00007fdb719b4b88>

SMILES for #<Metabolite:0x00007fdb719b4b88>

INCHI for #<Metabolite:0x00007fdb719b4b88>

Structure for #<Metabolite:0x00007fdb719b4b88>

3D Structure for #<Metabolite:0x00007fdb719b4b88>