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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 21:03:49 UTC

Update Date

2021-09-14 15:45:34 UTC

HMDB ID

HMDB0029135

Secondary Accession Numbers

HMDB29135

Metabolite Identification

Common Name

Valylproline

Description

Valylproline is a dipeptide composed of valine and proline. 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

HMDB0029135
     RDKit          3D
Valylproline
 33 33  0  0  0  0  0  0  0  0999 V2000
    1.9076   -0.1860   -1.9086 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4123    0.9190   -1.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3238    2.1336   -1.2736 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5472    0.6055    0.4425 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9819    0.4015    0.6425 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8425   -0.6208    0.8493 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5685   -1.6418    1.1178 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5452   -0.7638    0.9676 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2103   -2.0127    1.3613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5551   -2.0159    0.6668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5526   -0.7111   -0.1326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6595    0.1401    0.7838 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3423    0.4859    2.0307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9769    0.0429    3.1324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4336    1.3353    1.9881 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1885   -0.3106   -2.7626 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9087    0.0378   -2.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9399   -1.1735   -1.4091 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4049    1.2662   -1.2638 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0914    2.8414   -0.4528 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3597    1.7916   -1.1087 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1712    2.5531   -2.2780 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2432    1.5088    0.9962 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3989   -0.1927   -0.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4782    1.2697    0.8615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3751   -2.0960    2.4345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5844   -2.8628    1.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4050   -2.0566    1.3646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5658   -2.8359   -0.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5725   -0.2994   -0.1050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1172   -0.8222   -1.1240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4269    1.0350    0.1971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4463    2.2345    1.5353 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  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 12  8  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  1
  5 24  1  0
  5 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  6
 15 33  1  0
M  END


  Mrv1652304032018482D          

 15 15  0  0  0  0            999 V2000
10000.042810000.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.327710000.8257    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.605510000.4268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.889510000.8381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.6055 9999.5998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.327710001.6525    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10000.760010000.8257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.4132 9999.4953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1304 9999.0808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.413210000.3214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.0258 9999.5746    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3584 9999.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6133 9998.3050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.4383 9998.3050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.6932 9999.0896    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  2  0  0  0  0
  2  3  1  0  0  0  0
  2  6  1  6  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 11 12  1  0  0  0  0
 11 15  1  0  0  0  0
  1 11  1  0  0  0  0
 15  8  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0029135

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H18N2O3/c1-6(2)8(11)9(13)12-5-3-4-7(12)10(14)15/h6-8H,3-5,11H2,1-2H3,(H,14,15)/t7-,8-/m0/s1

> <INCHI_KEY>
GIAZPLMMQOERPN-YUMQZZPRSA-N

> <FORMULA>
C10H18N2O3

> <MOLECULAR_WEIGHT>
214.265

> <EXACT_MASS>
214.131742448

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
22.476828758305377

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-1-[(2S)-2-amino-3-methylbutanoyl]pyrrolidine-2-carboxylic acid

> <ALOGPS_LOGP>
-0.78

> <JCHEM_LOGP>
-2.21973410343997

> <ALOGPS_LOGS>
-0.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8554103709039587

> <JCHEM_PKA_STRONGEST_BASIC>
8.507320059823522

> <JCHEM_POLAR_SURFACE_AREA>
83.63000000000001

> <JCHEM_REFRACTIVITY>
54.47940000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.03e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-1-[(2S)-2-amino-3-methylbutanoyl]pyrrolidine-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029135
     RDKit          3D
Valylproline
 33 33  0  0  0  0  0  0  0  0999 V2000
    1.9076   -0.1860   -1.9086 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4123    0.9190   -1.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3238    2.1336   -1.2736 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5472    0.6055    0.4425 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9819    0.4015    0.6425 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8425   -0.6208    0.8493 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5685   -1.6418    1.1178 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5452   -0.7638    0.9676 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2103   -2.0127    1.3613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5551   -2.0159    0.6668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5526   -0.7111   -0.1326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6595    0.1401    0.7838 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3423    0.4859    2.0307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9769    0.0429    3.1324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4336    1.3353    1.9881 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1885   -0.3106   -2.7626 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9087    0.0378   -2.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9399   -1.1735   -1.4091 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4049    1.2662   -1.2638 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0914    2.8414   -0.4528 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3597    1.7916   -1.1087 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1712    2.5531   -2.2780 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2432    1.5088    0.9962 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3989   -0.1927   -0.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4782    1.2697    0.8615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3751   -2.0960    2.4345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5844   -2.8628    1.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4050   -2.0566    1.3646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5658   -2.8359   -0.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5725   -0.2994   -0.1050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1172   -0.8222   -1.1240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4269    1.0350    0.1971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4463    2.2345    1.5353 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  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 12  8  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  1
  5 24  1  0
  5 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  6
 15 33  1  0
M  END

HEADER    PROTEIN                                 03-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-APR-20         0                                  
HETATM    1  C   UNK     0    8666.7478667.440   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8665.4128668.208   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8664.0648667.463   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8662.7278668.231   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8664.0648665.920   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0    8665.4128669.751   0.000  0.00  0.00           N+0
HETATM    7  O   UNK     0    8668.0858668.208   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0    8669.3058665.725   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0    8670.6438664.951   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8669.3058667.267   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0    8666.7158665.873   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0    8665.4698664.967   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8665.9458663.503   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8667.4858663.503   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8667.9618664.967   0.000  0.00  0.00           C+0
CONECT    1    2    7   11                                                  
CONECT    2    1    3    6                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    2                                                            
CONECT    7    1                                                            
CONECT    8    9   10   15                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11   12   15    1                                                  
CONECT   12   13   11                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   11    8                                                  
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0029135
HETATM    1  C1  UNL     1       1.908  -0.186  -1.909  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.412   0.919  -1.036  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.324   2.134  -1.274  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.547   0.606   0.443  1.00  0.00           C  
HETATM    5  N1  UNL     1       2.982   0.402   0.642  1.00  0.00           N  
HETATM    6  C5  UNL     1       0.842  -0.621   0.849  1.00  0.00           C  
HETATM    7  O1  UNL     1       1.569  -1.642   1.118  1.00  0.00           O  
HETATM    8  N2  UNL     1      -0.545  -0.764   0.968  1.00  0.00           N  
HETATM    9  C6  UNL     1      -1.210  -2.013   1.361  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.555  -2.016   0.667  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.553  -0.711  -0.133  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.659   0.140   0.784  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.342   0.486   2.031  1.00  0.00           C  
HETATM   14  O2  UNL     1      -1.977   0.043   3.132  1.00  0.00           O  
HETATM   15  O3  UNL     1      -3.434   1.335   1.988  1.00  0.00           O  
HETATM   16  H1  UNL     1       1.189  -0.311  -2.763  1.00  0.00           H  
HETATM   17  H2  UNL     1       2.909   0.038  -2.340  1.00  0.00           H  
HETATM   18  H3  UNL     1       1.940  -1.173  -1.409  1.00  0.00           H  
HETATM   19  H4  UNL     1       0.405   1.266  -1.264  1.00  0.00           H  
HETATM   20  H5  UNL     1       2.091   2.841  -0.453  1.00  0.00           H  
HETATM   21  H6  UNL     1       3.360   1.792  -1.109  1.00  0.00           H  
HETATM   22  H7  UNL     1       2.171   2.553  -2.278  1.00  0.00           H  
HETATM   23  H8  UNL     1       1.243   1.509   0.996  1.00  0.00           H  
HETATM   24  H9  UNL     1       3.399  -0.193  -0.081  1.00  0.00           H  
HETATM   25  H10 UNL     1       3.478   1.270   0.862  1.00  0.00           H  
HETATM   26  H11 UNL     1      -1.375  -2.096   2.435  1.00  0.00           H  
HETATM   27  H12 UNL     1      -0.584  -2.863   1.005  1.00  0.00           H  
HETATM   28  H13 UNL     1      -3.405  -2.057   1.365  1.00  0.00           H  
HETATM   29  H14 UNL     1      -2.566  -2.836  -0.088  1.00  0.00           H  
HETATM   30  H15 UNL     1      -3.573  -0.299  -0.105  1.00  0.00           H  
HETATM   31  H16 UNL     1      -2.117  -0.822  -1.124  1.00  0.00           H  
HETATM   32  H17 UNL     1      -1.427   1.035   0.197  1.00  0.00           H  
HETATM   33  H18 UNL     1      -3.446   2.234   1.535  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    4   19
CONECT    3   20   21   22
CONECT    4    5    6   23
CONECT    5   24   25
CONECT    6    7    7    8
CONECT    8    9   12
CONECT    9   10   26   27
CONECT   10   11   28   29
CONECT   11   12   30   31
CONECT   12   13   32
CONECT   13   14   14   15
CONECT   15   33
END

HMDB0029135
     RDKit          3D
Valylproline
 33 33  0  0  0  0  0  0  0  0999 V2000
    1.9076   -0.1860   -1.9086 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4123    0.9190   -1.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3238    2.1336   -1.2736 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5472    0.6055    0.4425 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9819    0.4015    0.6425 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8425   -0.6208    0.8493 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5685   -1.6418    1.1178 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5452   -0.7638    0.9676 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2103   -2.0127    1.3613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5551   -2.0159    0.6668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5526   -0.7111   -0.1326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6595    0.1401    0.7838 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3423    0.4859    2.0307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9769    0.0429    3.1324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4336    1.3353    1.9881 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1885   -0.3106   -2.7626 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9087    0.0378   -2.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9399   -1.1735   -1.4091 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4049    1.2662   -1.2638 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0914    2.8414   -0.4528 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3597    1.7916   -1.1087 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1712    2.5531   -2.2780 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2432    1.5088    0.9962 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3989   -0.1927   -0.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4782    1.2697    0.8615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3751   -2.0960    2.4345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5844   -2.8628    1.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4050   -2.0566    1.3646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5658   -2.8359   -0.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5725   -0.2994   -0.1050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1172   -0.8222   -1.1240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4269    1.0350    0.1971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4463    2.2345    1.5353 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  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 12  8  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  1
  5 24  1  0
  5 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  6
 15 33  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
L-Val-L-pro	ChEBI
V-P	ChEBI
VP	ChEBI
1-L-Valyl-L-proline	HMDB
1-L-Valylproline	HMDB
L-Valyl-L-proline	HMDB
L-alpha-Valyl-L-proline	HMDB
L-Α-valyl-L-proline	HMDB
N-L-Valyl-L-proline	HMDB
N-Valylproline	HMDB
V-p Dipeptide	HMDB
VP Dipeptide	HMDB
Val-pro	HMDB
Valine proline dipeptide	HMDB
Valine-proline dipeptide	HMDB
Valyl-proline	HMDB
Valylproline	ChEBI

Chemical Formula

C₁₀H₁₈N₂O₃

Average Molecular Weight

214.265

Monoisotopic Molecular Weight

214.131742448

IUPAC Name

(2S)-1-[(2S)-2-amino-3-methylbutanoyl]pyrrolidine-2-carboxylic acid

Traditional Name

(2S)-1-[(2S)-2-amino-3-methylbutanoyl]pyrrolidine-2-carboxylic acid

CAS Registry Number

20488-27-1

SMILES

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

InChI Identifier

InChI=1S/C10H18N2O3/c1-6(2)8(11)9(13)12-5-3-4-7(12)10(14)15/h6-8H,3-5,11H2,1-2H3,(H,14,15)/t7-,8-/m0/s1

InChI Key

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

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

dipeptide (CHEBI:73701 )

Ontology

Not Available

Not Available

Not Available

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	-2.22	Extrapolated

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	103 g/L	ALOGPS
logP	-0.78	ALOGPS
logP	-2.2	ChemAxon
logS	-0.32	ALOGPS
pKa (Strongest Acidic)	3.86	ChemAxon
pKa (Strongest Basic)	8.51	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.63 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	54.48 m³·mol⁻¹	ChemAxon
Polarizability	22.48 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]+	152.118	30932474
DeepCCS	[M-H]-	149.76	30932474
DeepCCS	[M-2H]-	182.774	30932474
DeepCCS	[M+Na]+	158.211	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Valylproline	CC(C)[C@H](N)C(=O)N1CCC[C@H]1C(O)=O	2675.3	Standard polar	33892256
Valylproline	CC(C)[C@H](N)C(=O)N1CCC[C@H]1C(O)=O	1810.8	Standard non polar	33892256
Valylproline	CC(C)[C@H](N)C(=O)N1CCC[C@H]1C(O)=O	1869.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Valylproline,1TMS,isomer #1	CC(C)[C@H](N)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	1809.2	Semi standard non polar	33892256
Valylproline,1TMS,isomer #2	CC(C)[C@H](N[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O	1855.4	Semi standard non polar	33892256
Valylproline,2TMS,isomer #1	CC(C)[C@H](N[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	1861.8	Semi standard non polar	33892256
Valylproline,2TMS,isomer #1	CC(C)[C@H](N[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	1903.2	Standard non polar	33892256
Valylproline,2TMS,isomer #2	CC(C)[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1995.1	Semi standard non polar	33892256
Valylproline,2TMS,isomer #2	CC(C)[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1965.4	Standard non polar	33892256
Valylproline,3TMS,isomer #1	CC(C)[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2053.6	Semi standard non polar	33892256
Valylproline,3TMS,isomer #1	CC(C)[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2043.3	Standard non polar	33892256
Valylproline,1TBDMS,isomer #1	CC(C)[C@H](N)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	2043.6	Semi standard non polar	33892256
Valylproline,1TBDMS,isomer #2	CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O	2079.2	Semi standard non polar	33892256
Valylproline,2TBDMS,isomer #1	CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	2312.6	Semi standard non polar	33892256
Valylproline,2TBDMS,isomer #1	CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	2309.7	Standard non polar	33892256
Valylproline,2TBDMS,isomer #2	CC(C)[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2437.1	Semi standard non polar	33892256
Valylproline,2TBDMS,isomer #2	CC(C)[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2396.0	Standard non polar	33892256
Valylproline,3TBDMS,isomer #1	CC(C)[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2672.8	Semi standard non polar	33892256
Valylproline,3TBDMS,isomer #1	CC(C)[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2623.5	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Valylproline 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 - Valylproline 10V, Negative-QTOF	splash10-03di-0190000000-a2b677fc4252b284c757	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valylproline 20V, Negative-QTOF	splash10-03di-4900000000-fbea73dc727349bb2d7c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valylproline 40V, Negative-QTOF	splash10-03dj-9500000000-45b2fc983242246e181b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valylproline 10V, Positive-QTOF	splash10-014i-2980000000-2a6ecccc6a1cb4556002	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valylproline 20V, Positive-QTOF	splash10-01b9-9510000000-8b1f1a971d05a351af08	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valylproline 40V, Positive-QTOF	splash10-00di-9000000000-7efa18764ade27937c96	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

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

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB098235

KNApSAcK ID

Not Available

Chemspider ID

8012993

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9837272

PDB ID

Not Available

ChEBI ID

73701

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

Kruszewska H, Zareba T, Tyski S: Examination of antimicrobial activity of selected non-antibiotic medicinal preparations. Acta Pol Pharm. 2012 Nov-Dec;69(6):1368-71. [PubMed:23285704 ]
Moczar M, David P, Loisance D: Vascular substitute from human placental arteries: glycosaminoglycan and elastin synthesis in the neo-intimal hyperplasia. Life Support Syst. 1984 Jul-Sep;2(3):201-8. [PubMed:6503349 ]
Sjolund M, Madsen K, von der Mark K, Thyberg J: Phenotype modulation in primary cultures of smooth-muscle cells from rat aorta. Synthesis of collagen and elastin. Differentiation. 1986;32(2):173-80. [PubMed:3539683 ]
Jansen RS, Addie R, Merkx R, Fish A, Mahakena S, Bleijerveld OB, Altelaar M, IJlst L, Wanders RJ, Borst P, van de Wetering K: N-lactoyl-amino acids are ubiquitous metabolites that originate from CNDP2-mediated reverse proteolysis of lactate and amino acids. Proc Natl Acad Sci U S A. 2015 May 26;112(21):6601-6. doi: 10.1073/pnas.1424638112. Epub 2015 May 11. [PubMed:25964343 ]

Showing metabocard for Valylproline (HMDB0029135)

MOL for HMDB0029135 (Valylproline)

3D MOL for HMDB0029135 (Valylproline)

3D SDF for HMDB0029135 (Valylproline)

3D-SDF for HMDB0029135 (Valylproline)

PDB for HMDB0029135 (Valylproline)

3D PDB for HMDB0029135 (Valylproline)

SMILES for HMDB0029135 (Valylproline)

INCHI for HMDB0029135 (Valylproline)

Structure for HMDB0029135 (Valylproline)

3D Structure for HMDB0029135 (Valylproline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra