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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-06 21:03:48 UTC

Update Date

2021-09-14 15:45:33 UTC

HMDB ID

HMDB0029129

Secondary Accession Numbers

HMDB29129

Metabolite Identification

Common Name

Valylhistidine

Description

Valylhistidine is a dipeptide composed of valine and histidine. It is an incomplete breakdown product of protein digestion or protein catabolism. Dipeptides are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Some dipeptides are known to have physiological or cell-signalling 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

HMDB0029129
     RDKit          3D
Valylhistidine
 36 36  0  0  0  0  0  0  0  0999 V2000
    2.7597    2.4038    1.1801 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5897    0.9031    0.9062 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8545    0.3757    0.2892 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3705    0.7369    0.1042 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2357    1.2422    0.8355 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1226   -0.6630   -0.4023 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1644   -1.1714   -0.9447 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0624   -1.2050   -0.2543 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3339   -1.7867   -0.0956 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3660   -1.4544   -1.1152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6590   -0.0005   -1.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6186    0.7063   -0.4691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5754    2.0021   -0.8266 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6196    2.1383   -1.7496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0595    0.9118   -1.9718 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2251   -3.2968    0.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1288   -3.8857    0.0239 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4317   -3.9718    0.1723 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4496    2.6759    2.2090 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8049    2.7181    0.9725 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1058    2.9896    0.4997 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4676    0.4323    1.9000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8871    0.3948   -0.8035 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1315   -0.6053    0.7257 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6807    1.0691    0.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4624    1.3477   -0.8247 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0181    2.2316    0.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2884    1.0221    1.8488 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2788   -2.3152   -1.0243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7952   -1.4568    0.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3341   -1.9522   -0.8447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0568   -1.7712   -2.1409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2510    0.1974    0.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3736    3.0810   -2.2102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2877    0.7737   -2.6571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4936   -4.8175    0.7618 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
  4  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
  9 16  1  0
 16 17  2  0
 16 18  1  0
 15 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  6
  5 27  1  0
  5 28  1  0
  8 29  1  0
  9 30  1  1
 10 31  1  0
 10 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  1  0
 18 36  1  0
M  END


  Mrv1652304062014252D          

 18 18  0  0  0  0            999 V2000
10023.927210024.1004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10024.644310024.5123    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10025.358710024.1004    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10026.073110024.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10026.787610024.1004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10026.073110025.3371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10023.213810024.5123    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10022.498410024.1004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10021.784910024.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10022.498410023.2754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10023.213810025.3371    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10023.927210023.2754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10025.358710023.2754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10026.074910022.8619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10026.161410022.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10026.970310021.8675    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10027.383810022.5838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10026.830510023.1983    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  0  0  0  0
  1 12  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  7  8  1  0  0  0  0
  7 11  1  6  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  3 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 17 18  1  0  0  0  0
 14 18  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029129

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)[C@H](N)C(=O)N[C@@H](CC1=CN=CN1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H18N4O3/c1-6(2)9(12)10(16)15-8(11(17)18)3-7-4-13-5-14-7/h4-6,8-9H,3,12H2,1-2H3,(H,13,14)(H,15,16)(H,17,18)/t8-,9-/m0/s1

> <INCHI_KEY>
BNQVUHQWZGTIBX-IUCAKERBSA-N

> <FORMULA>
C11H18N4O3

> <MOLECULAR_WEIGHT>
254.29

> <EXACT_MASS>
254.137890456

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
25.340082183742812

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-[(2S)-2-amino-3-methylbutanamido]-3-(1H-imidazol-5-yl)propanoic acid

> <ALOGPS_LOGP>
-2.47

> <JCHEM_LOGP>
-3.221766572987926

> <ALOGPS_LOGS>
-1.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.77560561003456

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5289539811116084

> <JCHEM_PKA_STRONGEST_BASIC>
8.521793193333457

> <JCHEM_POLAR_SURFACE_AREA>
121.1

> <JCHEM_REFRACTIVITY>
64.352

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.17e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(2S)-2-amino-3-methylbutanamido]-3-(3H-imidazol-4-yl)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029129
     RDKit          3D
Valylhistidine
 36 36  0  0  0  0  0  0  0  0999 V2000
    2.7597    2.4038    1.1801 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5897    0.9031    0.9062 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8545    0.3757    0.2892 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3705    0.7369    0.1042 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2357    1.2422    0.8355 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1226   -0.6630   -0.4023 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1644   -1.1714   -0.9447 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0624   -1.2050   -0.2543 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3339   -1.7867   -0.0956 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3660   -1.4544   -1.1152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6590   -0.0005   -1.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6186    0.7063   -0.4691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5754    2.0021   -0.8266 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6196    2.1383   -1.7496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0595    0.9118   -1.9718 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2251   -3.2968    0.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1288   -3.8857    0.0239 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4317   -3.9718    0.1723 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4496    2.6759    2.2090 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8049    2.7181    0.9725 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1058    2.9896    0.4997 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4676    0.4323    1.9000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8871    0.3948   -0.8035 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1315   -0.6053    0.7257 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6807    1.0691    0.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4624    1.3477   -0.8247 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0181    2.2316    0.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2884    1.0221    1.8488 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2788   -2.3152   -1.0243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7952   -1.4568    0.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3341   -1.9522   -0.8447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0568   -1.7712   -2.1409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2510    0.1974    0.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3736    3.0810   -2.2102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2877    0.7737   -2.6571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4936   -4.8175    0.7618 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
  4  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
  9 16  1  0
 16 17  2  0
 16 18  1  0
 15 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  6
  5 27  1  0
  5 28  1  0
  8 29  1  0
  9 30  1  1
 10 31  1  0
 10 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  1  0
 18 36  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    8711.3318711.654   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    8712.6698712.423   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0    8714.0038711.654   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8715.3368712.423   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8716.6708711.654   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8715.3368713.963   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8709.9998712.423   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8708.6648711.654   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8707.3328712.423   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8708.6648710.114   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0    8709.9998713.963   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0    8711.3318710.114   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0    8714.0038710.114   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8715.3408709.342   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8715.5018707.807   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0    8717.0118707.486   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0    8717.7838708.823   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0    8716.7508709.970   0.000  0.00  0.00           N+0
CONECT    1    2    7   12                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    1    8   11                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    7                                                            
CONECT   12    1                                                            
CONECT   13    3   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   18   16                                                       
CONECT   18   17   14                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0029129
HETATM    1  C1  UNL     1       2.760   2.404   1.180  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.590   0.903   0.906  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.855   0.376   0.289  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.370   0.737   0.104  1.00  0.00           C  
HETATM    5  N1  UNL     1       0.236   1.242   0.835  1.00  0.00           N  
HETATM    6  C5  UNL     1       1.123  -0.663  -0.402  1.00  0.00           C  
HETATM    7  O1  UNL     1       2.164  -1.171  -0.945  1.00  0.00           O  
HETATM    8  N2  UNL     1      -0.062  -1.205  -0.254  1.00  0.00           N  
HETATM    9  C6  UNL     1      -1.334  -1.787  -0.096  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.366  -1.454  -1.115  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.659  -0.001  -1.190  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.619   0.706  -0.469  1.00  0.00           C  
HETATM   13  N3  UNL     1      -3.575   2.002  -0.827  1.00  0.00           N  
HETATM   14  C10 UNL     1      -2.620   2.138  -1.750  1.00  0.00           C  
HETATM   15  N4  UNL     1      -2.060   0.912  -1.972  1.00  0.00           N  
HETATM   16  C11 UNL     1      -1.225  -3.297   0.037  1.00  0.00           C  
HETATM   17  O2  UNL     1      -0.129  -3.886   0.024  1.00  0.00           O  
HETATM   18  O3  UNL     1      -2.432  -3.972   0.172  1.00  0.00           O  
HETATM   19  H1  UNL     1       2.450   2.676   2.209  1.00  0.00           H  
HETATM   20  H2  UNL     1       3.805   2.718   0.973  1.00  0.00           H  
HETATM   21  H3  UNL     1       2.106   2.990   0.500  1.00  0.00           H  
HETATM   22  H4  UNL     1       2.468   0.432   1.900  1.00  0.00           H  
HETATM   23  H5  UNL     1       3.887   0.395  -0.804  1.00  0.00           H  
HETATM   24  H6  UNL     1       4.131  -0.605   0.726  1.00  0.00           H  
HETATM   25  H7  UNL     1       4.681   1.069   0.626  1.00  0.00           H  
HETATM   26  H8  UNL     1       1.462   1.348  -0.825  1.00  0.00           H  
HETATM   27  H9  UNL     1       0.018   2.232   0.610  1.00  0.00           H  
HETATM   28  H10 UNL     1       0.288   1.022   1.849  1.00  0.00           H  
HETATM   29  H11 UNL     1       0.279  -2.315  -1.024  1.00  0.00           H  
HETATM   30  H12 UNL     1      -1.795  -1.457   0.922  1.00  0.00           H  
HETATM   31  H13 UNL     1      -3.334  -1.952  -0.845  1.00  0.00           H  
HETATM   32  H14 UNL     1      -2.057  -1.771  -2.141  1.00  0.00           H  
HETATM   33  H15 UNL     1      -4.251   0.197   0.247  1.00  0.00           H  
HETATM   34  H16 UNL     1      -2.374   3.081  -2.210  1.00  0.00           H  
HETATM   35  H17 UNL     1      -1.288   0.774  -2.657  1.00  0.00           H  
HETATM   36  H18 UNL     1      -2.494  -4.818   0.762  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    4   22
CONECT    3   23   24   25
CONECT    4    5    6   26
CONECT    5   27   28
CONECT    6    7    7    8
CONECT    8    9   29
CONECT    9   10   16   30
CONECT   10   11   31   32
CONECT   11   12   12   15
CONECT   12   13   33
CONECT   13   14   14
CONECT   14   15   34
CONECT   15   35
CONECT   16   17   17   18
CONECT   18   36
END

HMDB0029129
     RDKit          3D
Valylhistidine
 36 36  0  0  0  0  0  0  0  0999 V2000
    2.7597    2.4038    1.1801 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5897    0.9031    0.9062 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8545    0.3757    0.2892 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3705    0.7369    0.1042 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2357    1.2422    0.8355 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1226   -0.6630   -0.4023 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1644   -1.1714   -0.9447 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0624   -1.2050   -0.2543 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3339   -1.7867   -0.0956 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3660   -1.4544   -1.1152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6590   -0.0005   -1.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6186    0.7063   -0.4691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5754    2.0021   -0.8266 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6196    2.1383   -1.7496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0595    0.9118   -1.9718 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2251   -3.2968    0.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1288   -3.8857    0.0239 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4317   -3.9718    0.1723 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4496    2.6759    2.2090 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8049    2.7181    0.9725 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1058    2.9896    0.4997 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4676    0.4323    1.9000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8871    0.3948   -0.8035 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1315   -0.6053    0.7257 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6807    1.0691    0.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4624    1.3477   -0.8247 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0181    2.2316    0.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2884    1.0221    1.8488 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2788   -2.3152   -1.0243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7952   -1.4568    0.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3341   -1.9522   -0.8447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0568   -1.7712   -2.1409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2510    0.1974    0.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3736    3.0810   -2.2102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2877    0.7737   -2.6571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4936   -4.8175    0.7618 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
  4  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
  9 16  1  0
 16 17  2  0
 16 18  1  0
 15 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  6
  5 27  1  0
  5 28  1  0
  8 29  1  0
  9 30  1  1
 10 31  1  0
 10 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  1  0
 18 36  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
L-Val-L-his	ChEBI
V-H	ChEBI
VH	ChEBI
L-Valyl-L-histidine	HMDB
N-L-Valyl-L-histidine	HMDB
N-Valylhistidine	HMDB
V-H Dipeptide	HMDB
VH Dipeptide	HMDB
Val-his	HMDB
Valine histidine dipeptide	HMDB
Valine-histidine dipeptide	HMDB
Valyl-histidine	HMDB
Valylhistidine	ChEBI

Chemical Formula

C₁₁H₁₈N₄O₃

Average Molecular Weight

254.29

Monoisotopic Molecular Weight

254.137890456

IUPAC Name

(2S)-2-[(2S)-2-amino-3-methylbutanamido]-3-(1H-imidazol-5-yl)propanoic acid

Traditional Name

(2S)-2-[(2S)-2-amino-3-methylbutanamido]-3-(3H-imidazol-4-yl)propanoic acid

CAS Registry Number

13589-07-6

SMILES

CC(C)[C@H](N)C(=O)N[C@@H](CC1=CN=CN1)C(O)=O

InChI Identifier

InChI=1S/C11H18N4O3/c1-6(2)9(12)10(16)15-8(11(17)18)3-7-4-13-5-14-7/h4-6,8-9H,3,12H2,1-2H3,(H,13,14)(H,15,16)(H,17,18)/t8-,9-/m0/s1

InChI Key

BNQVUHQWZGTIBX-IUCAKERBSA-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
Histidine or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Valine or derivatives
N-acyl-l-alpha-amino acid
Alpha-amino acid amide
Alpha-amino acid or derivatives
Imidazolyl carboxylic acid derivative
N-acyl-amine
Fatty amide
Fatty acyl
Azole
Imidazole
Heteroaromatic compound
Carboxamide group
Secondary carboxylic acid amide
Amino acid or derivatives
Amino acid
Carboxylic acid salt
Azacycle
Carboxylic acid
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Primary aliphatic amine
Organic zwitterion
Organic salt
Amine
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

dipeptide (CHEBI:73700 )

Ontology

Not Available

Feces (PMID: 25037050)

Source

Endogenous

Endogenous (HMDB: HMDB0029129)

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	-3.03	Extrapolated

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	6.17 g/L	ALOGPS
logP	-2.5	ALOGPS
logP	-3.2	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	3.53	ChemAxon
pKa (Strongest Basic)	8.52	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	121.1 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	64.35 m³·mol⁻¹	ChemAxon
Polarizability	25.34 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]+	161.853	30932474
DeepCCS	[M-H]-	159.495	30932474
DeepCCS	[M-2H]-	192.382	30932474
DeepCCS	[M+Na]+	167.946	30932474

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.	1.81 minutes	32390414
Predicted by Siyang on May 30, 2022	10.0736 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	8.75 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	403.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	457.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	239.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	50.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	158.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	47.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	317.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	254.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	844.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	599.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	48.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	742.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	168.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	232.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	477.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	641.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	357.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Valylhistidine	CC(C)[C@H](N)C(=O)N[C@@H](CC1=CN=CN1)C(O)=O	3197.2	Standard polar	33892256
Valylhistidine	CC(C)[C@H](N)C(=O)N[C@@H](CC1=CN=CN1)C(O)=O	2078.8	Standard non polar	33892256
Valylhistidine	CC(C)[C@H](N)C(=O)N[C@@H](CC1=CN=CN1)C(O)=O	2440.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Valylhistidine,1TMS,isomer #1	CC(C)[C@H](N)C(=O)N[C@@H](CC1=CN=C[NH]1)C(=O)O[Si](C)(C)C	2332.6	Semi standard non polar	33892256
Valylhistidine,1TMS,isomer #2	CC(C)[C@H](N[Si](C)(C)C)C(=O)N[C@@H](CC1=CN=C[NH]1)C(=O)O	2383.6	Semi standard non polar	33892256
Valylhistidine,1TMS,isomer #3	CC(C)[C@H](N)C(=O)N([C@@H](CC1=CN=C[NH]1)C(=O)O)[Si](C)(C)C	2293.4	Semi standard non polar	33892256
Valylhistidine,1TMS,isomer #4	CC(C)[C@H](N)C(=O)N[C@@H](CC1=CN=CN1[Si](C)(C)C)C(=O)O	2430.8	Semi standard non polar	33892256
Valylhistidine,2TMS,isomer #1	CC(C)[C@H](N[Si](C)(C)C)C(=O)N[C@@H](CC1=CN=C[NH]1)C(=O)O[Si](C)(C)C	2376.0	Semi standard non polar	33892256
Valylhistidine,2TMS,isomer #1	CC(C)[C@H](N[Si](C)(C)C)C(=O)N[C@@H](CC1=CN=C[NH]1)C(=O)O[Si](C)(C)C	2301.0	Standard non polar	33892256
Valylhistidine,2TMS,isomer #2	CC(C)[C@H](N)C(=O)N([C@@H](CC1=CN=C[NH]1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2299.1	Semi standard non polar	33892256
Valylhistidine,2TMS,isomer #2	CC(C)[C@H](N)C(=O)N([C@@H](CC1=CN=C[NH]1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2318.2	Standard non polar	33892256
Valylhistidine,2TMS,isomer #3	CC(C)[C@H](N)C(=O)N[C@@H](CC1=CN=CN1[Si](C)(C)C)C(=O)O[Si](C)(C)C	2439.5	Semi standard non polar	33892256
Valylhistidine,2TMS,isomer #3	CC(C)[C@H](N)C(=O)N[C@@H](CC1=CN=CN1[Si](C)(C)C)C(=O)O[Si](C)(C)C	2281.0	Standard non polar	33892256
Valylhistidine,2TMS,isomer #4	CC(C)[C@@H](C(=O)N[C@@H](CC1=CN=C[NH]1)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2471.2	Semi standard non polar	33892256
Valylhistidine,2TMS,isomer #4	CC(C)[C@@H](C(=O)N[C@@H](CC1=CN=C[NH]1)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2454.2	Standard non polar	33892256
Valylhistidine,2TMS,isomer #5	CC(C)[C@H](N[Si](C)(C)C)C(=O)N([C@@H](CC1=CN=C[NH]1)C(=O)O)[Si](C)(C)C	2326.1	Semi standard non polar	33892256
Valylhistidine,2TMS,isomer #5	CC(C)[C@H](N[Si](C)(C)C)C(=O)N([C@@H](CC1=CN=C[NH]1)C(=O)O)[Si](C)(C)C	2364.0	Standard non polar	33892256
Valylhistidine,2TMS,isomer #6	CC(C)[C@H](N[Si](C)(C)C)C(=O)N[C@@H](CC1=CN=CN1[Si](C)(C)C)C(=O)O	2477.3	Semi standard non polar	33892256
Valylhistidine,2TMS,isomer #6	CC(C)[C@H](N[Si](C)(C)C)C(=O)N[C@@H](CC1=CN=CN1[Si](C)(C)C)C(=O)O	2345.4	Standard non polar	33892256
Valylhistidine,2TMS,isomer #7	CC(C)[C@H](N)C(=O)N([C@@H](CC1=CN=CN1[Si](C)(C)C)C(=O)O)[Si](C)(C)C	2399.7	Semi standard non polar	33892256
Valylhistidine,2TMS,isomer #7	CC(C)[C@H](N)C(=O)N([C@@H](CC1=CN=CN1[Si](C)(C)C)C(=O)O)[Si](C)(C)C	2394.1	Standard non polar	33892256
Valylhistidine,3TMS,isomer #1	CC(C)[C@@H](C(=O)N[C@@H](CC1=CN=C[NH]1)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2448.3	Semi standard non polar	33892256
Valylhistidine,3TMS,isomer #1	CC(C)[C@@H](C(=O)N[C@@H](CC1=CN=C[NH]1)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2419.9	Standard non polar	33892256
Valylhistidine,3TMS,isomer #2	CC(C)[C@H](N[Si](C)(C)C)C(=O)N([C@@H](CC1=CN=C[NH]1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2323.0	Semi standard non polar	33892256
Valylhistidine,3TMS,isomer #2	CC(C)[C@H](N[Si](C)(C)C)C(=O)N([C@@H](CC1=CN=C[NH]1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2340.0	Standard non polar	33892256
Valylhistidine,3TMS,isomer #3	CC(C)[C@H](N[Si](C)(C)C)C(=O)N[C@@H](CC1=CN=CN1[Si](C)(C)C)C(=O)O[Si](C)(C)C	2500.2	Semi standard non polar	33892256
Valylhistidine,3TMS,isomer #3	CC(C)[C@H](N[Si](C)(C)C)C(=O)N[C@@H](CC1=CN=CN1[Si](C)(C)C)C(=O)O[Si](C)(C)C	2342.1	Standard non polar	33892256
Valylhistidine,3TMS,isomer #4	CC(C)[C@H](N)C(=O)N([C@@H](CC1=CN=CN1[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2427.4	Semi standard non polar	33892256
Valylhistidine,3TMS,isomer #4	CC(C)[C@H](N)C(=O)N([C@@H](CC1=CN=CN1[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2425.6	Standard non polar	33892256
Valylhistidine,3TMS,isomer #5	CC(C)[C@@H](C(=O)N([C@@H](CC1=CN=C[NH]1)C(=O)O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2442.6	Semi standard non polar	33892256
Valylhistidine,3TMS,isomer #5	CC(C)[C@@H](C(=O)N([C@@H](CC1=CN=C[NH]1)C(=O)O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2511.6	Standard non polar	33892256
Valylhistidine,3TMS,isomer #6	CC(C)[C@@H](C(=O)N[C@@H](CC1=CN=CN1[Si](C)(C)C)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2621.3	Semi standard non polar	33892256
Valylhistidine,3TMS,isomer #6	CC(C)[C@@H](C(=O)N[C@@H](CC1=CN=CN1[Si](C)(C)C)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2477.1	Standard non polar	33892256
Valylhistidine,3TMS,isomer #7	CC(C)[C@H](N[Si](C)(C)C)C(=O)N([C@@H](CC1=CN=CN1[Si](C)(C)C)C(=O)O)[Si](C)(C)C	2461.5	Semi standard non polar	33892256
Valylhistidine,3TMS,isomer #7	CC(C)[C@H](N[Si](C)(C)C)C(=O)N([C@@H](CC1=CN=CN1[Si](C)(C)C)C(=O)O)[Si](C)(C)C	2414.4	Standard non polar	33892256
Valylhistidine,4TMS,isomer #1	CC(C)[C@@H](C(=O)N([C@@H](CC1=CN=C[NH]1)C(=O)O[Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2494.2	Semi standard non polar	33892256
Valylhistidine,4TMS,isomer #1	CC(C)[C@@H](C(=O)N([C@@H](CC1=CN=C[NH]1)C(=O)O[Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2497.1	Standard non polar	33892256
Valylhistidine,4TMS,isomer #2	CC(C)[C@@H](C(=O)N[C@@H](CC1=CN=CN1[Si](C)(C)C)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2615.2	Semi standard non polar	33892256
Valylhistidine,4TMS,isomer #2	CC(C)[C@@H](C(=O)N[C@@H](CC1=CN=CN1[Si](C)(C)C)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2495.5	Standard non polar	33892256
Valylhistidine,4TMS,isomer #3	CC(C)[C@H](N[Si](C)(C)C)C(=O)N([C@@H](CC1=CN=CN1[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2461.7	Semi standard non polar	33892256
Valylhistidine,4TMS,isomer #3	CC(C)[C@H](N[Si](C)(C)C)C(=O)N([C@@H](CC1=CN=CN1[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2428.2	Standard non polar	33892256
Valylhistidine,4TMS,isomer #4	CC(C)[C@@H](C(=O)N([C@@H](CC1=CN=CN1[Si](C)(C)C)C(=O)O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2606.4	Semi standard non polar	33892256
Valylhistidine,4TMS,isomer #4	CC(C)[C@@H](C(=O)N([C@@H](CC1=CN=CN1[Si](C)(C)C)C(=O)O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2588.4	Standard non polar	33892256
Valylhistidine,5TMS,isomer #1	CC(C)[C@@H](C(=O)N([C@@H](CC1=CN=CN1[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2667.7	Semi standard non polar	33892256
Valylhistidine,5TMS,isomer #1	CC(C)[C@@H](C(=O)N([C@@H](CC1=CN=CN1[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2599.0	Standard non polar	33892256
Valylhistidine,1TBDMS,isomer #1	CC(C)[C@H](N)C(=O)N[C@@H](CC1=CN=C[NH]1)C(=O)O[Si](C)(C)C(C)(C)C	2577.5	Semi standard non polar	33892256
Valylhistidine,1TBDMS,isomer #2	CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N[C@@H](CC1=CN=C[NH]1)C(=O)O	2586.6	Semi standard non polar	33892256
Valylhistidine,1TBDMS,isomer #3	CC(C)[C@H](N)C(=O)N([C@@H](CC1=CN=C[NH]1)C(=O)O)[Si](C)(C)C(C)(C)C	2535.1	Semi standard non polar	33892256
Valylhistidine,1TBDMS,isomer #4	CC(C)[C@H](N)C(=O)N[C@@H](CC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)O	2692.7	Semi standard non polar	33892256
Valylhistidine,2TBDMS,isomer #1	CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N[C@@H](CC1=CN=C[NH]1)C(=O)O[Si](C)(C)C(C)(C)C	2807.4	Semi standard non polar	33892256
Valylhistidine,2TBDMS,isomer #1	CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N[C@@H](CC1=CN=C[NH]1)C(=O)O[Si](C)(C)C(C)(C)C	2717.7	Standard non polar	33892256
Valylhistidine,2TBDMS,isomer #2	CC(C)[C@H](N)C(=O)N([C@@H](CC1=CN=C[NH]1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2756.9	Semi standard non polar	33892256
Valylhistidine,2TBDMS,isomer #2	CC(C)[C@H](N)C(=O)N([C@@H](CC1=CN=C[NH]1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2742.5	Standard non polar	33892256
Valylhistidine,2TBDMS,isomer #3	CC(C)[C@H](N)C(=O)N[C@@H](CC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2923.0	Semi standard non polar	33892256
Valylhistidine,2TBDMS,isomer #3	CC(C)[C@H](N)C(=O)N[C@@H](CC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2702.5	Standard non polar	33892256
Valylhistidine,2TBDMS,isomer #4	CC(C)[C@@H](C(=O)N[C@@H](CC1=CN=C[NH]1)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2913.4	Semi standard non polar	33892256
Valylhistidine,2TBDMS,isomer #4	CC(C)[C@@H](C(=O)N[C@@H](CC1=CN=C[NH]1)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2828.3	Standard non polar	33892256
Valylhistidine,2TBDMS,isomer #5	CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N([C@@H](CC1=CN=C[NH]1)C(=O)O)[Si](C)(C)C(C)(C)C	2781.3	Semi standard non polar	33892256
Valylhistidine,2TBDMS,isomer #5	CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N([C@@H](CC1=CN=C[NH]1)C(=O)O)[Si](C)(C)C(C)(C)C	2754.5	Standard non polar	33892256
Valylhistidine,2TBDMS,isomer #6	CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N[C@@H](CC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)O	2940.7	Semi standard non polar	33892256
Valylhistidine,2TBDMS,isomer #6	CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N[C@@H](CC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)O	2744.0	Standard non polar	33892256
Valylhistidine,2TBDMS,isomer #7	CC(C)[C@H](N)C(=O)N([C@@H](CC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	2878.9	Semi standard non polar	33892256
Valylhistidine,2TBDMS,isomer #7	CC(C)[C@H](N)C(=O)N([C@@H](CC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	2784.2	Standard non polar	33892256
Valylhistidine,3TBDMS,isomer #1	CC(C)[C@@H](C(=O)N[C@@H](CC1=CN=C[NH]1)C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3138.2	Semi standard non polar	33892256
Valylhistidine,3TBDMS,isomer #1	CC(C)[C@@H](C(=O)N[C@@H](CC1=CN=C[NH]1)C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2958.2	Standard non polar	33892256
Valylhistidine,3TBDMS,isomer #2	CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N([C@@H](CC1=CN=C[NH]1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2989.8	Semi standard non polar	33892256
Valylhistidine,3TBDMS,isomer #2	CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N([C@@H](CC1=CN=C[NH]1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2889.9	Standard non polar	33892256
Valylhistidine,3TBDMS,isomer #3	CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N[C@@H](CC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3139.6	Semi standard non polar	33892256
Valylhistidine,3TBDMS,isomer #3	CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N[C@@H](CC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2929.8	Standard non polar	33892256
Valylhistidine,3TBDMS,isomer #4	CC(C)[C@H](N)C(=O)N([C@@H](CC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3077.8	Semi standard non polar	33892256
Valylhistidine,3TBDMS,isomer #4	CC(C)[C@H](N)C(=O)N([C@@H](CC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3010.4	Standard non polar	33892256
Valylhistidine,3TBDMS,isomer #5	CC(C)[C@@H](C(=O)N([C@@H](CC1=CN=C[NH]1)C(=O)O)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3087.2	Semi standard non polar	33892256
Valylhistidine,3TBDMS,isomer #5	CC(C)[C@@H](C(=O)N([C@@H](CC1=CN=C[NH]1)C(=O)O)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3033.5	Standard non polar	33892256
Valylhistidine,3TBDMS,isomer #6	CC(C)[C@@H](C(=O)N[C@@H](CC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3301.6	Semi standard non polar	33892256
Valylhistidine,3TBDMS,isomer #6	CC(C)[C@@H](C(=O)N[C@@H](CC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3017.0	Standard non polar	33892256
Valylhistidine,3TBDMS,isomer #7	CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N([C@@H](CC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	3125.3	Semi standard non polar	33892256
Valylhistidine,3TBDMS,isomer #7	CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N([C@@H](CC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	2968.9	Standard non polar	33892256
Valylhistidine,4TBDMS,isomer #1	CC(C)[C@@H](C(=O)N([C@@H](CC1=CN=C[NH]1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3327.3	Semi standard non polar	33892256
Valylhistidine,4TBDMS,isomer #1	CC(C)[C@@H](C(=O)N([C@@H](CC1=CN=C[NH]1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3175.9	Standard non polar	33892256
Valylhistidine,4TBDMS,isomer #2	CC(C)[C@@H](C(=O)N[C@@H](CC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3480.3	Semi standard non polar	33892256
Valylhistidine,4TBDMS,isomer #2	CC(C)[C@@H](C(=O)N[C@@H](CC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3199.2	Standard non polar	33892256
Valylhistidine,4TBDMS,isomer #3	CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N([C@@H](CC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3301.0	Semi standard non polar	33892256
Valylhistidine,4TBDMS,isomer #3	CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N([C@@H](CC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3153.6	Standard non polar	33892256
Valylhistidine,4TBDMS,isomer #4	CC(C)[C@@H](C(=O)N([C@@H](CC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3462.3	Semi standard non polar	33892256
Valylhistidine,4TBDMS,isomer #4	CC(C)[C@@H](C(=O)N([C@@H](CC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3254.6	Standard non polar	33892256
Valylhistidine,5TBDMS,isomer #1	CC(C)[C@@H](C(=O)N([C@@H](CC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3661.6	Semi standard non polar	33892256
Valylhistidine,5TBDMS,isomer #1	CC(C)[C@@H](C(=O)N([C@@H](CC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3453.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Valylhistidine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Valylhistidine 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 - Valylhistidine 10V, Negative-QTOF	splash10-0udi-0690000000-54918bc2bfdb31f63095	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valylhistidine 20V, Negative-QTOF	splash10-0a4i-4900000000-d7184ea7b59d57b3c260	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valylhistidine 40V, Negative-QTOF	splash10-066u-9600000000-90deb2911a10fd34993f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valylhistidine 10V, Positive-QTOF	splash10-0a4i-0190000000-339823bbe10c974f110f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valylhistidine 20V, Positive-QTOF	splash10-0c00-9800000000-8d87f4e9800d3d01c9f9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valylhistidine 40V, Positive-QTOF	splash10-08gl-9400000000-5b9772fb4f263b515e3d	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	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	25037050	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
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

FDB112131

KNApSAcK ID

Not Available

Chemspider ID

5731283

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7408624

PDB ID

Not Available

ChEBI ID

73700

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

Dixon HB: A reaction of glucose with peptides. Biochem J. 1972 Aug;129(1):203-8. [PubMed:4646775 ]
Ichiyanagi A, Hirokawa K, Gomi K, Nakatsu T, Kato H, Kajiyama N: Crystallization and preliminary crystallographic analysis of two eukaryotic fructosyl peptide oxidases. Acta Crystallogr Sect F Struct Biol Cryst Commun. 2013 Feb 1;69(Pt 2):130-3. doi: 10.1107/S1744309112051445. Epub 2013 Jan 30. [PubMed:23385752 ]
Mori N, Manning JM: Studies on the Amadori rearrangement in a model system: chromatographic isolation of intermediates and product. Anal Biochem. 1986 Feb 1;152(2):396-401. [PubMed:3963373 ]

Showing metabocard for Valylhistidine (HMDB0029129)

MOL for HMDB0029129 (Valylhistidine)

3D MOL for HMDB0029129 (Valylhistidine)

3D SDF for HMDB0029129 (Valylhistidine)

3D-SDF for HMDB0029129 (Valylhistidine)

PDB for HMDB0029129 (Valylhistidine)

3D PDB for HMDB0029129 (Valylhistidine)

SMILES for HMDB0029129 (Valylhistidine)

INCHI for HMDB0029129 (Valylhistidine)

Structure for HMDB0029129 (Valylhistidine)

3D Structure for HMDB0029129 (Valylhistidine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra