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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-06 21:02:40 UTC

Update Date

2021-09-14 15:45:45 UTC

HMDB ID

HMDB0028832

Secondary Accession Numbers

HMDB0059717
HMDB28832
HMDB59717

Metabolite Identification

Common Name

Glutamylvaline

Description

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

Structure

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

HMDB0028832
     RDKit          3D
Glutamylvaline
 35 34  0  0  0  0  0  0  0  0999 V2000
   -1.7637    1.8195   -0.8141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6382    1.0229    0.1735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6773    0.2634   -0.5297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7183    0.2317    1.0635 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8841   -0.5507    0.1157 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5530   -0.3563    0.2555 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9170    0.4303    1.1713 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4365   -1.0403   -0.6078 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9347   -0.9035   -1.9947 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9023   -1.0088   -0.5562 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6260    0.2856   -0.6716 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7538    1.0704    0.5938 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8541    2.2791    0.4806 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7649    0.3505    1.7559 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5546   -0.7835    1.7772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8287   -0.6944    1.6959 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0276   -1.8045    2.4974 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8211    2.0260   -0.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5374    1.0589   -1.6232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3176    2.6738   -1.2164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1345    1.8074    0.8094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9860    0.8721   -1.4624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6551    0.1836    0.0195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3588   -0.6949   -0.9288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1200    0.8498    1.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3638   -1.1443   -0.5471 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2001   -2.1838   -0.4043 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9012   -1.8553   -2.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6878   -0.3793   -2.5132 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3342   -1.8542   -1.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1244   -1.3518    0.5586 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0073    0.9755   -1.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5822    0.2324   -1.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3252    0.5907    2.5561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5178   -2.4180    3.0953 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
  8 10  1  0
 10 11  1  0
 11 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  1
  9 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 14 34  1  0
 17 35  1  0
M  END

      
  Mrv1652304062013412D          

 17 16  0  0  0  0            999 V2000
 2501.7860 2500.0010    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2501.0720 2499.5877    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3580 2500.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6419 2499.5877    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2498.9279 2500.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.2139 2499.5877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.4998 2500.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2496.7859 2499.5877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2497.4998 2500.8255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6419 2498.7633    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3580 2500.8255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.5000 2499.5877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.2140 2500.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.5000 2498.7633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.7860 2500.8255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.5000 2501.2366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.0720 2501.2366    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
  4 10  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  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>
HMDB0028832

> <DATABASE_NAME>
hmdb

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

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

> <INCHI_KEY>
SITLTJHOQZFJGG-XPUUQOCRSA-N

> <FORMULA>
C10H18N2O5

> <MOLECULAR_WEIGHT>
246.2603

> <EXACT_MASS>
246.121571696

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
24.684483436125653

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-2.95

> <JCHEM_LOGP>
-3.0870598443062156

> <ALOGPS_LOGS>
-1.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.246657564243728

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.429747502735709

> <JCHEM_PKA_STRONGEST_BASIC>
8.449795306283493

> <JCHEM_POLAR_SURFACE_AREA>
129.72

> <JCHEM_REFRACTIVITY>
57.5807

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.01e+01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0028832
     RDKit          3D
Glutamylvaline
 35 34  0  0  0  0  0  0  0  0999 V2000
   -1.7637    1.8195   -0.8141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6382    1.0229    0.1735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6773    0.2634   -0.5297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7183    0.2317    1.0635 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8841   -0.5507    0.1157 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5530   -0.3563    0.2555 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9170    0.4303    1.1713 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4365   -1.0403   -0.6078 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9347   -0.9035   -1.9947 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9023   -1.0088   -0.5562 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6260    0.2856   -0.6716 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7538    1.0704    0.5938 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8541    2.2791    0.4806 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7649    0.3505    1.7559 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5546   -0.7835    1.7772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8287   -0.6944    1.6959 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0276   -1.8045    2.4974 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8211    2.0260   -0.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5374    1.0589   -1.6232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3176    2.6738   -1.2164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1345    1.8074    0.8094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9860    0.8721   -1.4624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6551    0.1836    0.0195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3588   -0.6949   -0.9288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1200    0.8498    1.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3638   -1.1443   -0.5471 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2001   -2.1838   -0.4043 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9012   -1.8553   -2.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6878   -0.3793   -2.5132 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3342   -1.8542   -1.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1244   -1.3518    0.5586 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0073    0.9755   -1.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5822    0.2324   -1.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3252    0.5907    2.5561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5178   -2.4180    3.0953 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
  8 10  1  0
 10 11  1  0
 11 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  1
  9 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 14 34  1  0
 17 35  1  0
M  END

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  C   UNK     0    4670.0014666.669   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    4668.6684665.897   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0    4667.3354666.669   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    4665.9984665.897   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    4664.6654666.669   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    4663.3334665.897   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    4662.0004666.669   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    4660.6674665.897   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    4662.0004668.208   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0    4665.9984664.358   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0    4667.3354668.208   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    4671.3334665.897   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    4672.6664666.669   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    4671.3334664.358   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    4670.0014668.208   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0    4671.3334668.975   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0    4668.6684668.975   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   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    4                                                            
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    HMDB0028832
HETATM    1  C1  UNL     1      -1.764   1.820  -0.814  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.638   1.023   0.173  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.677   0.263  -0.530  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.718   0.232   1.063  1.00  0.00           C  
HETATM    5  N1  UNL     1      -0.884  -0.551   0.116  1.00  0.00           N  
HETATM    6  C5  UNL     1       0.553  -0.356   0.256  1.00  0.00           C  
HETATM    7  O1  UNL     1       0.917   0.430   1.171  1.00  0.00           O  
HETATM    8  C6  UNL     1       1.436  -1.040  -0.608  1.00  0.00           C  
HETATM    9  N2  UNL     1       0.935  -0.904  -1.995  1.00  0.00           N  
HETATM   10  C7  UNL     1       2.902  -1.009  -0.556  1.00  0.00           C  
HETATM   11  C8  UNL     1       3.626   0.286  -0.672  1.00  0.00           C  
HETATM   12  C9  UNL     1       3.754   1.070   0.594  1.00  0.00           C  
HETATM   13  O2  UNL     1       3.854   2.279   0.481  1.00  0.00           O  
HETATM   14  O3  UNL     1       3.765   0.351   1.756  1.00  0.00           O  
HETATM   15  C10 UNL     1      -2.555  -0.784   1.777  1.00  0.00           C  
HETATM   16  O4  UNL     1      -3.829  -0.694   1.696  1.00  0.00           O  
HETATM   17  O5  UNL     1      -2.028  -1.805   2.497  1.00  0.00           O  
HETATM   18  H1  UNL     1      -0.821   2.026  -0.302  1.00  0.00           H  
HETATM   19  H2  UNL     1      -1.537   1.059  -1.623  1.00  0.00           H  
HETATM   20  H3  UNL     1      -2.318   2.674  -1.216  1.00  0.00           H  
HETATM   21  H4  UNL     1      -3.134   1.807   0.809  1.00  0.00           H  
HETATM   22  H5  UNL     1      -3.986   0.872  -1.462  1.00  0.00           H  
HETATM   23  H6  UNL     1      -4.655   0.184   0.019  1.00  0.00           H  
HETATM   24  H7  UNL     1      -3.359  -0.695  -0.929  1.00  0.00           H  
HETATM   25  H8  UNL     1      -1.120   0.850   1.712  1.00  0.00           H  
HETATM   26  H9  UNL     1      -1.364  -1.144  -0.547  1.00  0.00           H  
HETATM   27  H10 UNL     1       1.200  -2.184  -0.404  1.00  0.00           H  
HETATM   28  H11 UNL     1       0.901  -1.855  -2.463  1.00  0.00           H  
HETATM   29  H12 UNL     1       1.688  -0.379  -2.513  1.00  0.00           H  
HETATM   30  H13 UNL     1       3.334  -1.854  -1.124  1.00  0.00           H  
HETATM   31  H14 UNL     1       3.124  -1.352   0.559  1.00  0.00           H  
HETATM   32  H15 UNL     1       3.007   0.976  -1.398  1.00  0.00           H  
HETATM   33  H16 UNL     1       4.582   0.232  -1.175  1.00  0.00           H  
HETATM   34  H17 UNL     1       4.325   0.591   2.556  1.00  0.00           H  
HETATM   35  H18 UNL     1      -2.518  -2.418   3.095  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   10   27
CONECT    9   28   29
CONECT   10   11   30   31
CONECT   11   12   32   33
CONECT   12   13   13   14
CONECT   14   34
CONECT   15   16   16   17
CONECT   17   35
END

HMDB0028832
     RDKit          3D
Glutamylvaline
 35 34  0  0  0  0  0  0  0  0999 V2000
   -1.7637    1.8195   -0.8141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6382    1.0229    0.1735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6773    0.2634   -0.5297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7183    0.2317    1.0635 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8841   -0.5507    0.1157 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5530   -0.3563    0.2555 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9170    0.4303    1.1713 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4365   -1.0403   -0.6078 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9347   -0.9035   -1.9947 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9023   -1.0088   -0.5562 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6260    0.2856   -0.6716 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7538    1.0704    0.5938 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8541    2.2791    0.4806 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7649    0.3505    1.7559 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5546   -0.7835    1.7772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8287   -0.6944    1.6959 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0276   -1.8045    2.4974 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8211    2.0260   -0.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5374    1.0589   -1.6232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3176    2.6738   -1.2164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1345    1.8074    0.8094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9860    0.8721   -1.4624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6551    0.1836    0.0195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3588   -0.6949   -0.9288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1200    0.8498    1.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3638   -1.1443   -0.5471 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2001   -2.1838   -0.4043 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9012   -1.8553   -2.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6878   -0.3793   -2.5132 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3342   -1.8542   -1.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1244   -1.3518    0.5586 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0073    0.9755   -1.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5822    0.2324   -1.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3252    0.5907    2.5561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5178   -2.4180    3.0953 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
  8 10  1  0
 10 11  1  0
 11 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  1
  9 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 14 34  1  0
 17 35  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
alpha-Glu-val	ChEBI
Glutamyl-valine	ChEBI
L-alpha-Glu-L-val	ChEBI
L-Glu-L-val	ChEBI
L-Glutamyl-L-valine	ChEBI
a-Glu-val	Generator
Α-glu-val	Generator
L-a-Glu-L-val	Generator
L-Α-glu-L-val	Generator
Α-L-glu-L-val	HMDB
Α-glutamylvaline	HMDB
Α-L-glutamyl-L-valine	HMDB
L-Α-glutamyl-L-valine	HMDB
N-Α-glutamylvaline	HMDB
N-Α-L-glutamyl-L-valine	HMDB
N-L-Α-glutamylvaline	HMDB
N-L-Α-glutamyl-L-valine	HMDB
alpha-L-Glu-L-val	HMDB
alpha-Glutamylvaline	HMDB
alpha-L-Glutamyl-L-valine	HMDB
L-alpha-Glutamyl-L-valine	HMDB
N-alpha-Glutamylvaline	HMDB
N-alpha-L-Glutamyl-L-valine	HMDB
N-L-alpha-Glutamylvaline	HMDB
N-L-alpha-Glutamyl-L-valine	HMDB
NSC 334345	HMDB
Glu-val	HMDB
N-Glutamylvaline	HMDB
N-L-Glutamyl-L-valine	HMDB
Glutamic acid valine dipeptide	HMDB
Glutamate valine dipeptide	HMDB
Glutamic acid-valine dipeptide	HMDB
Glutamate-valine dipeptide	HMDB
e-V Dipeptide	HMDB
EV dipeptide	HMDB
Glutamylvaline	HMDB, ChEBI

Chemical Formula

C₁₀H₁₈N₂O₅

Average Molecular Weight

246.2603

Monoisotopic Molecular Weight

246.121571696

IUPAC Name

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

Traditional Name

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

CAS Registry Number

5879-06-1

SMILES

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

InChI Identifier

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

InChI Key

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

glutamyl-L-amino acid (CHEBI:68846 )

Ontology

Not Available

Feces (PMID: 27015276)

Source

Endogenous

Endogenous (HMDB: HMDB0028832)

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	-3.08	Extrapolated

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	33.7 g/L	ALOGPS
logP	-3	ALOGPS
logP	-3.1	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	3.43	ChemAxon
pKa (Strongest Basic)	8.45	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	129.72 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	57.58 m³·mol⁻¹	ChemAxon
Polarizability	24.68 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	155.984	31661259
DarkChem	[M-H]-	153.915	31661259
DeepCCS	[M+H]+	161.737	30932474
DeepCCS	[M-H]-	159.379	30932474
DeepCCS	[M-2H]-	192.266	30932474
DeepCCS	[M+Na]+	167.83	30932474
AllCCS	[M+H]+	155.6	32859911
AllCCS	[M+H-H2O]+	152.4	32859911
AllCCS	[M+NH4]+	158.5	32859911
AllCCS	[M+Na]+	159.4	32859911
AllCCS	[M-H]-	155.2	32859911
AllCCS	[M+Na-2H]-	155.9	32859911
AllCCS	[M+HCOO]-	156.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.37 minutes	32390414
Predicted by Siyang on May 30, 2022	9.8938 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	8.35 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	320.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Glutamylvaline	CC(C)[C@H](NC(=O)[C@@H](N)CCC(O)=O)C(O)=O	3231.9	Standard polar	33892256
Glutamylvaline	CC(C)[C@H](NC(=O)[C@@H](N)CCC(O)=O)C(O)=O	1932.4	Standard non polar	33892256
Glutamylvaline	CC(C)[C@H](NC(=O)[C@@H](N)CCC(O)=O)C(O)=O	2149.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Glutamylvaline,1TMS,isomer #1	CC(C)[C@H](NC(=O)[C@@H](N)CCC(=O)O[Si](C)(C)C)C(=O)O	2107.8	Semi standard non polar	33892256
Glutamylvaline,1TMS,isomer #2	CC(C)[C@H](NC(=O)[C@@H](N)CCC(=O)O)C(=O)O[Si](C)(C)C	2101.4	Semi standard non polar	33892256
Glutamylvaline,1TMS,isomer #3	CC(C)[C@H](NC(=O)[C@H](CCC(=O)O)N[Si](C)(C)C)C(=O)O	2142.5	Semi standard non polar	33892256
Glutamylvaline,1TMS,isomer #4	CC(C)[C@@H](C(=O)O)N(C(=O)[C@@H](N)CCC(=O)O)[Si](C)(C)C	2054.7	Semi standard non polar	33892256
Glutamylvaline,2TMS,isomer #1	CC(C)[C@H](NC(=O)[C@@H](N)CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2123.0	Semi standard non polar	33892256
Glutamylvaline,2TMS,isomer #2	CC(C)[C@H](NC(=O)[C@H](CCC(=O)O[Si](C)(C)C)N[Si](C)(C)C)C(=O)O	2165.8	Semi standard non polar	33892256
Glutamylvaline,2TMS,isomer #3	CC(C)[C@@H](C(=O)O)N(C(=O)[C@@H](N)CCC(=O)O[Si](C)(C)C)[Si](C)(C)C	2044.8	Semi standard non polar	33892256
Glutamylvaline,2TMS,isomer #4	CC(C)[C@H](NC(=O)[C@H](CCC(=O)O)N[Si](C)(C)C)C(=O)O[Si](C)(C)C	2167.8	Semi standard non polar	33892256
Glutamylvaline,2TMS,isomer #5	CC(C)[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@@H](N)CCC(=O)O)[Si](C)(C)C	2075.3	Semi standard non polar	33892256
Glutamylvaline,2TMS,isomer #6	CC(C)[C@@H](C(=O)O)N(C(=O)[C@H](CCC(=O)O)N[Si](C)(C)C)[Si](C)(C)C	2135.0	Semi standard non polar	33892256
Glutamylvaline,2TMS,isomer #7	CC(C)[C@H](NC(=O)[C@H](CCC(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	2287.7	Semi standard non polar	33892256
Glutamylvaline,3TMS,isomer #1	CC(C)[C@H](NC(=O)[C@H](CCC(=O)O[Si](C)(C)C)N[Si](C)(C)C)C(=O)O[Si](C)(C)C	2168.6	Semi standard non polar	33892256
Glutamylvaline,3TMS,isomer #1	CC(C)[C@H](NC(=O)[C@H](CCC(=O)O[Si](C)(C)C)N[Si](C)(C)C)C(=O)O[Si](C)(C)C	2149.1	Standard non polar	33892256
Glutamylvaline,3TMS,isomer #2	CC(C)[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@@H](N)CCC(=O)O[Si](C)(C)C)[Si](C)(C)C	2073.6	Semi standard non polar	33892256
Glutamylvaline,3TMS,isomer #2	CC(C)[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@@H](N)CCC(=O)O[Si](C)(C)C)[Si](C)(C)C	2135.2	Standard non polar	33892256
Glutamylvaline,3TMS,isomer #3	CC(C)[C@@H](C(=O)O)N(C(=O)[C@H](CCC(=O)O[Si](C)(C)C)N[Si](C)(C)C)[Si](C)(C)C	2109.1	Semi standard non polar	33892256
Glutamylvaline,3TMS,isomer #3	CC(C)[C@@H](C(=O)O)N(C(=O)[C@H](CCC(=O)O[Si](C)(C)C)N[Si](C)(C)C)[Si](C)(C)C	2193.3	Standard non polar	33892256
Glutamylvaline,3TMS,isomer #4	CC(C)[C@H](NC(=O)[C@H](CCC(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	2297.8	Semi standard non polar	33892256
Glutamylvaline,3TMS,isomer #4	CC(C)[C@H](NC(=O)[C@H](CCC(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	2222.2	Standard non polar	33892256
Glutamylvaline,3TMS,isomer #5	CC(C)[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@H](CCC(=O)O)N[Si](C)(C)C)[Si](C)(C)C	2139.8	Semi standard non polar	33892256
Glutamylvaline,3TMS,isomer #5	CC(C)[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@H](CCC(=O)O)N[Si](C)(C)C)[Si](C)(C)C	2168.9	Standard non polar	33892256
Glutamylvaline,3TMS,isomer #6	CC(C)[C@H](NC(=O)[C@H](CCC(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2306.8	Semi standard non polar	33892256
Glutamylvaline,3TMS,isomer #6	CC(C)[C@H](NC(=O)[C@H](CCC(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2207.5	Standard non polar	33892256
Glutamylvaline,3TMS,isomer #7	CC(C)[C@@H](C(=O)O)N(C(=O)[C@H](CCC(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2264.5	Semi standard non polar	33892256
Glutamylvaline,3TMS,isomer #7	CC(C)[C@@H](C(=O)O)N(C(=O)[C@H](CCC(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2239.6	Standard non polar	33892256
Glutamylvaline,4TMS,isomer #1	CC(C)[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@H](CCC(=O)O[Si](C)(C)C)N[Si](C)(C)C)[Si](C)(C)C	2138.1	Semi standard non polar	33892256
Glutamylvaline,4TMS,isomer #1	CC(C)[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@H](CCC(=O)O[Si](C)(C)C)N[Si](C)(C)C)[Si](C)(C)C	2226.4	Standard non polar	33892256
Glutamylvaline,4TMS,isomer #2	CC(C)[C@H](NC(=O)[C@H](CCC(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2279.7	Semi standard non polar	33892256
Glutamylvaline,4TMS,isomer #2	CC(C)[C@H](NC(=O)[C@H](CCC(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2270.6	Standard non polar	33892256
Glutamylvaline,4TMS,isomer #3	CC(C)[C@@H](C(=O)O)N(C(=O)[C@H](CCC(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2278.9	Semi standard non polar	33892256
Glutamylvaline,4TMS,isomer #3	CC(C)[C@@H](C(=O)O)N(C(=O)[C@H](CCC(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2307.9	Standard non polar	33892256
Glutamylvaline,4TMS,isomer #4	CC(C)[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@H](CCC(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2306.1	Semi standard non polar	33892256
Glutamylvaline,4TMS,isomer #4	CC(C)[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@H](CCC(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2285.7	Standard non polar	33892256
Glutamylvaline,5TMS,isomer #1	CC(C)[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@H](CCC(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2330.2	Semi standard non polar	33892256
Glutamylvaline,5TMS,isomer #1	CC(C)[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@H](CCC(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2344.4	Standard non polar	33892256
Glutamylvaline,1TBDMS,isomer #1	CC(C)[C@H](NC(=O)[C@@H](N)CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	2351.1	Semi standard non polar	33892256
Glutamylvaline,1TBDMS,isomer #2	CC(C)[C@H](NC(=O)[C@@H](N)CCC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	2337.7	Semi standard non polar	33892256
Glutamylvaline,1TBDMS,isomer #3	CC(C)[C@H](NC(=O)[C@H](CCC(=O)O)N[Si](C)(C)C(C)(C)C)C(=O)O	2369.0	Semi standard non polar	33892256
Glutamylvaline,1TBDMS,isomer #4	CC(C)[C@@H](C(=O)O)N(C(=O)[C@@H](N)CCC(=O)O)[Si](C)(C)C(C)(C)C	2305.7	Semi standard non polar	33892256
Glutamylvaline,2TBDMS,isomer #1	CC(C)[C@H](NC(=O)[C@@H](N)CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2555.6	Semi standard non polar	33892256
Glutamylvaline,2TBDMS,isomer #2	CC(C)[C@H](NC(=O)[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)C(=O)O	2605.6	Semi standard non polar	33892256
Glutamylvaline,2TBDMS,isomer #3	CC(C)[C@@H](C(=O)O)N(C(=O)[C@@H](N)CCC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2527.8	Semi standard non polar	33892256
Glutamylvaline,2TBDMS,isomer #4	CC(C)[C@H](NC(=O)[C@H](CCC(=O)O)N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2588.8	Semi standard non polar	33892256
Glutamylvaline,2TBDMS,isomer #5	CC(C)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@@H](N)CCC(=O)O)[Si](C)(C)C(C)(C)C	2532.4	Semi standard non polar	33892256
Glutamylvaline,2TBDMS,isomer #6	CC(C)[C@@H](C(=O)O)N(C(=O)[C@H](CCC(=O)O)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2587.1	Semi standard non polar	33892256
Glutamylvaline,2TBDMS,isomer #7	CC(C)[C@H](NC(=O)[C@H](CCC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	2697.2	Semi standard non polar	33892256
Glutamylvaline,3TBDMS,isomer #1	CC(C)[C@H](NC(=O)[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2805.1	Semi standard non polar	33892256
Glutamylvaline,3TBDMS,isomer #1	CC(C)[C@H](NC(=O)[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2685.3	Standard non polar	33892256
Glutamylvaline,3TBDMS,isomer #2	CC(C)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@@H](N)CCC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2748.8	Semi standard non polar	33892256
Glutamylvaline,3TBDMS,isomer #2	CC(C)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@@H](N)CCC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2682.2	Standard non polar	33892256
Glutamylvaline,3TBDMS,isomer #3	CC(C)[C@@H](C(=O)O)N(C(=O)[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2817.2	Semi standard non polar	33892256
Glutamylvaline,3TBDMS,isomer #3	CC(C)[C@@H](C(=O)O)N(C(=O)[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2694.5	Standard non polar	33892256
Glutamylvaline,3TBDMS,isomer #4	CC(C)[C@H](NC(=O)[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	2970.3	Semi standard non polar	33892256
Glutamylvaline,3TBDMS,isomer #4	CC(C)[C@H](NC(=O)[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	2740.8	Standard non polar	33892256
Glutamylvaline,3TBDMS,isomer #5	CC(C)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@H](CCC(=O)O)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2810.0	Semi standard non polar	33892256
Glutamylvaline,3TBDMS,isomer #5	CC(C)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@H](CCC(=O)O)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2668.8	Standard non polar	33892256
Glutamylvaline,3TBDMS,isomer #6	CC(C)[C@H](NC(=O)[C@H](CCC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2951.5	Semi standard non polar	33892256
Glutamylvaline,3TBDMS,isomer #6	CC(C)[C@H](NC(=O)[C@H](CCC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2706.2	Standard non polar	33892256
Glutamylvaline,3TBDMS,isomer #7	CC(C)[C@@H](C(=O)O)N(C(=O)[C@H](CCC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2943.0	Semi standard non polar	33892256
Glutamylvaline,3TBDMS,isomer #7	CC(C)[C@@H](C(=O)O)N(C(=O)[C@H](CCC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2719.4	Standard non polar	33892256
Glutamylvaline,4TBDMS,isomer #1	CC(C)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3009.8	Semi standard non polar	33892256
Glutamylvaline,4TBDMS,isomer #1	CC(C)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2894.3	Standard non polar	33892256
Glutamylvaline,4TBDMS,isomer #2	CC(C)[C@H](NC(=O)[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3179.2	Semi standard non polar	33892256
Glutamylvaline,4TBDMS,isomer #2	CC(C)[C@H](NC(=O)[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2935.3	Standard non polar	33892256
Glutamylvaline,4TBDMS,isomer #3	CC(C)[C@@H](C(=O)O)N(C(=O)[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3177.5	Semi standard non polar	33892256
Glutamylvaline,4TBDMS,isomer #3	CC(C)[C@@H](C(=O)O)N(C(=O)[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2959.4	Standard non polar	33892256
Glutamylvaline,4TBDMS,isomer #4	CC(C)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@H](CCC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3170.3	Semi standard non polar	33892256
Glutamylvaline,4TBDMS,isomer #4	CC(C)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@H](CCC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2938.7	Standard non polar	33892256
Glutamylvaline,5TBDMS,isomer #1	CC(C)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3407.0	Semi standard non polar	33892256
Glutamylvaline,5TBDMS,isomer #1	CC(C)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3161.6	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Glutamylvaline GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-5910000000-dd206506b861529c598a	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glutamylvaline GC-MS (2 TMS) - 70eV, Positive	splash10-00di-7932000000-595f11ef6b35decd47d8	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glutamylvaline 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 - Glutamylvaline 10V, Positive-QTOF	splash10-0fb9-0390000000-fc60f6b4840884b6e83b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamylvaline 20V, Positive-QTOF	splash10-0uki-9730000000-5f2ae69e6f8b9b6f1dec	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamylvaline 40V, Positive-QTOF	splash10-0a4i-9100000000-7fd20ef70cf9ada32371	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamylvaline 10V, Negative-QTOF	splash10-0f6t-0190000000-c60caad92d79605d6dbd	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamylvaline 20V, Negative-QTOF	splash10-0fvj-2980000000-10ae3625f985d16042df	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamylvaline 40V, Negative-QTOF	splash10-01ba-8900000000-f1ca76cd02d3da89f5ad	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamylvaline 10V, Positive-QTOF	splash10-015a-1960000000-f9006730da0729f9edc1	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamylvaline 20V, Positive-QTOF	splash10-0ue9-4900000000-c37cd1f5d5d59f336494	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamylvaline 40V, Positive-QTOF	splash10-0a4i-9100000000-5b26ce5e030ae3c3279b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamylvaline 10V, Negative-QTOF	splash10-0002-0290000000-db6b00543f1b7512cb99	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamylvaline 20V, Negative-QTOF	splash10-004i-1900000000-8425065a485b241e2404	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamylvaline 40V, Negative-QTOF	splash10-0006-9500000000-e7692717f665a97bc5af	2021-10-12	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

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details

Associated Disorders and Diseases

Disease References

Colorectal cancer

Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB111873

KNApSAcK ID

Not Available

Chemspider ID

5360697

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6992567

PDB ID

Not Available

ChEBI ID

68846

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

Jandke J, Spiteller G: Dipeptide analysis in human urine. J Chromatogr. 1986 Oct 31;382:39-45. [PubMed:3782411 ]
Sovago I, Farkas E, Bertalan C, Lebkiri A, Kowalik-Jankowska T, Kozlowski H: Copper(II) complexes of dipeptides containing aspartyl, glutamyl, and histidyl residues in the side chain. J Inorg Biochem. 1993 Sep;51(4):715-26. [PubMed:7902418 ]
Kanazawa A, Kakimoto Y, Nakajima T, Sano I: Identification of gamma-glutamylserine, gamma-glutamylalanine, gamma-glutamylvaline and S-methylglutathione of bovine brain. Biochim Biophys Acta. 1965 Nov 15;111(1):90-5. [PubMed:5867340 ]
Schmugge M, Waye JS, Basran RK, Zurbriggen K, Frischknecht H: THE Hb S/beta+ -thalassemia phenotype demonstrates that the IVS-I (-2) (A>C) mutation is a mild beta-thalassemia allele. Hemoglobin. 2008;32(3):303-7. doi: 10.1080/03630260802004459. [PubMed:18473247 ]
Suzuki H, Kato K, Kumagai H: Enzymatic synthesis of gamma-glutamylvaline to improve the bitter taste of valine. J Agric Food Chem. 2004 Feb 11;52(3):577-80. [PubMed:14759151 ]
Frischknecht H, Troxler H, Greiner J, Hengartner H, Dutly F: Compound heterozygosity for Hb S [beta6(A3)GluVal, GAG-->GTG] and a new thalassemic mutation [beta132(H10)Lys-->term, AAA-->TAA] detected in a family from West Africa. Hemoglobin. 2008;32(3):309-13. doi: 10.1080/03630260701758866. [PubMed:18473248 ]

Showing metabocard for Glutamylvaline (HMDB0028832)

MOL for HMDB0028832 (Glutamylvaline)

3D MOL for HMDB0028832 (Glutamylvaline)

3D SDF for HMDB0028832 (Glutamylvaline)

3D-SDF for HMDB0028832 (Glutamylvaline)

PDB for HMDB0028832 (Glutamylvaline)

3D PDB for HMDB0028832 (Glutamylvaline)

SMILES for HMDB0028832 (Glutamylvaline)

INCHI for HMDB0028832 (Glutamylvaline)

Structure for HMDB0028832 (Glutamylvaline)

3D Structure for HMDB0028832 (Glutamylvaline)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra