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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 21:03:48 UTC

Update Date

2021-09-14 15:45:34 UTC

HMDB ID

HMDB0029128

Secondary Accession Numbers

HMDB29128

Metabolite Identification

Common Name

Valylhydroxyproline

Description

Valylhydroxyproline, also known as V-HP dipeptide or val-hpro, 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. Valylhydroxyproline has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make valylhydroxyproline a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Valylhydroxyproline.

Structure

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

HMDB0029128
     RDKit          3D
Valylhydroxyproline
 34 34  0  0  0  0  0  0  0  0999 V2000
    2.7309   -0.7150   -0.7967 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6626    0.4728    0.1320 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5773    0.1527    1.3116 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2787    0.7086    0.6862 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8868   -0.4527    1.4162 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2992    1.1650   -0.3257 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6641    2.1354   -1.0370 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9789    0.6067   -0.5429 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9038    1.1208   -1.5720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2644    0.9476   -0.9036 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3354    1.8665    0.1428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1095   -0.4319   -0.3241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6657   -0.4790    0.1061 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1568   -1.8007   -0.2753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2532   -1.9027   -1.1265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6851   -2.9306    0.3145 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7700   -0.7752   -1.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5053   -1.6563   -0.2893 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0839   -0.5745   -1.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0821    1.3731   -0.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1104   -0.7982    1.1881 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3623    0.9365    1.4439 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9967    0.0676    2.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3896    1.5614    1.4216 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4548   -0.2425    2.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6097   -1.2015    1.4729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8902    0.4222   -2.4320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6856    2.1484   -1.8554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0872    1.0341   -1.6134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4694    2.3028    0.3007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7986   -0.6116    0.5303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3002   -1.1868   -1.1422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6550   -0.3385    1.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2256   -2.9243    1.1679 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
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13  8  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  1
  5 25  1  0
  5 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  6
 11 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  1
 16 34  1  0
M  END


  Mrv1652304062014252D          

 16 16  0  0  0  0            999 V2000
10002.1009 9999.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.8128 9999.2054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.100910000.4412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.8095 9997.7700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.7175 9999.7002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10000.0502 9999.2152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3051 9998.4306    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.1301 9998.4306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.3850 9999.2152    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.717510000.5252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.432010000.9377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.574110000.9377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.288610000.5252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.003110001.7627    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10000.003110000.9377    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.2886 9999.7002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  7  4  1  1  0  0  0
  9  1  1  6  0  0  0
  5 10  1  0  0  0  0
 10 11  2  0  0  0  0
 15 13  1  0  0  0  0
 15 14  1  6  0  0  0
 10 15  1  0  0  0  0
 13 12  1  0  0  0  0
 13 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029128

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)[C@H](N)C(=O)N1C[C@H](O)C[C@H]1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H18N2O4/c1-5(2)8(11)9(14)12-4-6(13)3-7(12)10(15)16/h5-8,13H,3-4,11H2,1-2H3,(H,15,16)/t6-,7+,8+/m1/s1

> <INCHI_KEY>
IMOKOCYUKGZZAG-CSMHCCOUSA-N

> <FORMULA>
C10H18N2O4

> <MOLECULAR_WEIGHT>
230.264

> <EXACT_MASS>
230.126657068

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
23.23841017514942

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,4R)-1-[(2S)-2-amino-3-methylbutanoyl]-4-hydroxypyrrolidine-2-carboxylic acid

> <ALOGPS_LOGP>
-2.60

> <JCHEM_LOGP>
-3.3671717214364403

> <ALOGPS_LOGS>
-0.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.826415671193917

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.685008763455723

> <JCHEM_PKA_STRONGEST_BASIC>
8.507267035243478

> <JCHEM_POLAR_SURFACE_AREA>
103.86

> <JCHEM_REFRACTIVITY>
55.7973

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.57e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,4R)-1-[(2S)-2-amino-3-methylbutanoyl]-4-hydroxypyrrolidine-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029128
     RDKit          3D
Valylhydroxyproline
 34 34  0  0  0  0  0  0  0  0999 V2000
    2.7309   -0.7150   -0.7967 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6626    0.4728    0.1320 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5773    0.1527    1.3116 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2787    0.7086    0.6862 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8868   -0.4527    1.4162 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2992    1.1650   -0.3257 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6641    2.1354   -1.0370 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9789    0.6067   -0.5429 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9038    1.1208   -1.5720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2644    0.9476   -0.9036 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3354    1.8665    0.1428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1095   -0.4319   -0.3241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6657   -0.4790    0.1061 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1568   -1.8007   -0.2753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2532   -1.9027   -1.1265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6851   -2.9306    0.3145 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7700   -0.7752   -1.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5053   -1.6563   -0.2893 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0839   -0.5745   -1.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0821    1.3731   -0.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1104   -0.7982    1.1881 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3623    0.9365    1.4439 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9967    0.0676    2.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3896    1.5614    1.4216 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4548   -0.2425    2.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6097   -1.2015    1.4729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8902    0.4222   -2.4320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6856    2.1484   -1.8554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0872    1.0341   -1.6134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4694    2.3028    0.3007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7986   -0.6116    0.5303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3002   -1.1868   -1.1422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6550   -0.3385    1.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2256   -2.9243    1.1679 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
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13  8  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  1
  5 25  1  0
  5 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  6
 11 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  1
 16 34  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    8670.5888665.953   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8671.9178665.183   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8670.5888667.490   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8666.3118662.504   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0    8668.0068666.107   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0    8666.7608665.202   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8667.2368663.737   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8668.7768663.737   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8669.2528665.202   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8668.0068667.647   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8669.3408668.417   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8664.0058668.417   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8665.3398667.647   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0    8666.6728669.957   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0    8666.6728668.417   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8665.3398666.107   0.000  0.00  0.00           C+0
CONECT    1    2    3    9                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    7                                                            
CONECT    5    6    9   10                                                  
CONECT    6    7    5                                                       
CONECT    7    6    8    4                                                  
CONECT    8    7    9                                                       
CONECT    9    8    5    1                                                  
CONECT   10    5   11   15                                                  
CONECT   11   10                                                            
CONECT   12   13                                                            
CONECT   13   15   12   16                                                  
CONECT   14   15                                                            
CONECT   15   13   14   10                                                  
CONECT   16   13                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0029128
HETATM    1  C1  UNL     1       2.731  -0.715  -0.797  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.663   0.473   0.132  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.577   0.153   1.312  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.279   0.709   0.686  1.00  0.00           C  
HETATM    5  N1  UNL     1       0.887  -0.453   1.416  1.00  0.00           N  
HETATM    6  C5  UNL     1       0.299   1.165  -0.326  1.00  0.00           C  
HETATM    7  O1  UNL     1       0.664   2.135  -1.037  1.00  0.00           O  
HETATM    8  N2  UNL     1      -0.979   0.607  -0.543  1.00  0.00           N  
HETATM    9  C6  UNL     1      -1.904   1.121  -1.572  1.00  0.00           C  
HETATM   10  C7  UNL     1      -3.264   0.948  -0.904  1.00  0.00           C  
HETATM   11  O2  UNL     1      -3.335   1.866   0.143  1.00  0.00           O  
HETATM   12  C8  UNL     1      -3.110  -0.432  -0.324  1.00  0.00           C  
HETATM   13  C9  UNL     1      -1.666  -0.479   0.106  1.00  0.00           C  
HETATM   14  C10 UNL     1      -1.157  -1.801  -0.275  1.00  0.00           C  
HETATM   15  O3  UNL     1      -0.253  -1.903  -1.127  1.00  0.00           O  
HETATM   16  O4  UNL     1      -1.685  -2.931   0.315  1.00  0.00           O  
HETATM   17  H1  UNL     1       3.770  -0.775  -1.182  1.00  0.00           H  
HETATM   18  H2  UNL     1       2.505  -1.656  -0.289  1.00  0.00           H  
HETATM   19  H3  UNL     1       2.084  -0.575  -1.688  1.00  0.00           H  
HETATM   20  H4  UNL     1       3.082   1.373  -0.358  1.00  0.00           H  
HETATM   21  H5  UNL     1       4.110  -0.798   1.188  1.00  0.00           H  
HETATM   22  H6  UNL     1       4.362   0.937   1.444  1.00  0.00           H  
HETATM   23  H7  UNL     1       2.997   0.068   2.264  1.00  0.00           H  
HETATM   24  H8  UNL     1       1.390   1.561   1.422  1.00  0.00           H  
HETATM   25  H9  UNL     1       0.455  -0.243   2.345  1.00  0.00           H  
HETATM   26  H10 UNL     1       1.610  -1.201   1.473  1.00  0.00           H  
HETATM   27  H11 UNL     1      -1.890   0.422  -2.432  1.00  0.00           H  
HETATM   28  H12 UNL     1      -1.686   2.148  -1.855  1.00  0.00           H  
HETATM   29  H13 UNL     1      -4.087   1.034  -1.613  1.00  0.00           H  
HETATM   30  H14 UNL     1      -2.469   2.303   0.301  1.00  0.00           H  
HETATM   31  H15 UNL     1      -3.799  -0.612   0.530  1.00  0.00           H  
HETATM   32  H16 UNL     1      -3.300  -1.187  -1.142  1.00  0.00           H  
HETATM   33  H17 UNL     1      -1.655  -0.338   1.221  1.00  0.00           H  
HETATM   34  H18 UNL     1      -2.226  -2.924   1.168  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    4   20
CONECT    3   21   22   23
CONECT    4    5    6   24
CONECT    5   25   26
CONECT    6    7    7    8
CONECT    8    9   13
CONECT    9   10   27   28
CONECT   10   11   12   29
CONECT   11   30
CONECT   12   13   31   32
CONECT   13   14   33
CONECT   14   15   15   16
CONECT   16   34
END

HMDB0029128
     RDKit          3D
Valylhydroxyproline
 34 34  0  0  0  0  0  0  0  0999 V2000
    2.7309   -0.7150   -0.7967 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6626    0.4728    0.1320 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5773    0.1527    1.3116 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2787    0.7086    0.6862 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8868   -0.4527    1.4162 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2992    1.1650   -0.3257 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6641    2.1354   -1.0370 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9789    0.6067   -0.5429 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9038    1.1208   -1.5720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2644    0.9476   -0.9036 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3354    1.8665    0.1428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1095   -0.4319   -0.3241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6657   -0.4790    0.1061 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1568   -1.8007   -0.2753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2532   -1.9027   -1.1265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6851   -2.9306    0.3145 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7700   -0.7752   -1.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5053   -1.6563   -0.2893 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0839   -0.5745   -1.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0821    1.3731   -0.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1104   -0.7982    1.1881 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3623    0.9365    1.4439 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9967    0.0676    2.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3896    1.5614    1.4216 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4548   -0.2425    2.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6097   -1.2015    1.4729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8902    0.4222   -2.4320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6856    2.1484   -1.8554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0872    1.0341   -1.6134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4694    2.3028    0.3007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7986   -0.6116    0.5303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3002   -1.1868   -1.1422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6550   -0.3385    1.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2256   -2.9243    1.1679 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
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13  8  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  1
  5 25  1  0
  5 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  6
 11 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  1
 16 34  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Valine hydroxyproline dipeptide	HMDB
L-Valyl-L-hydroxyproline	HMDB
V-HP Dipeptide	HMDB
Val-hpro	HMDB
Valine-hydroxyproline dipeptide	HMDB
VHP Dipeptide	HMDB
Val-hyp	HMDB
L-Val-L-hyp	HMDB
Valyl-hydroxyproline	HMDB
(2S,4R)-1-[(2S)-2-Amino-3-methylbutanoyl]-4-hydroxypyrrolidine-2-carboxylate	HMDB
Valylhydroxyproline	HMDB

Chemical Formula

C₁₀H₁₈N₂O₄

Average Molecular Weight

230.264

Monoisotopic Molecular Weight

230.126657068

IUPAC Name

(2S,4R)-1-[(2S)-2-amino-3-methylbutanoyl]-4-hydroxypyrrolidine-2-carboxylic acid

Traditional Name

(2S,4R)-1-[(2S)-2-amino-3-methylbutanoyl]-4-hydroxypyrrolidine-2-carboxylic acid

CAS Registry Number

90965-79-0

SMILES

CC(C)[C@H](N)C(=O)N1C[C@H](O)C[C@H]1C(O)=O

InChI Identifier

InChI=1S/C10H18N2O4/c1-5(2)8(11)9(14)12-4-6(13)3-7(12)10(15)16/h5-8,13H,3-4,11H2,1-2H3,(H,15,16)/t6-,7+,8+/m1/s1

InChI Key

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

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	-3.37	Extrapolated

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	65.7 g/L	ALOGPS
logP	-2.6	ALOGPS
logP	-3.4	ChemAxon
logS	-0.54	ALOGPS
pKa (Strongest Acidic)	3.69	ChemAxon
pKa (Strongest Basic)	8.51	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	103.86 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	55.8 m³·mol⁻¹	ChemAxon
Polarizability	23.24 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]+	159.65	30932474
DeepCCS	[M-H]-	157.292	30932474
DeepCCS	[M-2H]-	190.178	30932474
DeepCCS	[M+Na]+	165.743	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Valylhydroxyproline	CC(C)[C@H](N)C(=O)N1C[C@H](O)C[C@H]1C(O)=O	2990.6	Standard polar	33892256
Valylhydroxyproline	CC(C)[C@H](N)C(=O)N1C[C@H](O)C[C@H]1C(O)=O	1920.4	Standard non polar	33892256
Valylhydroxyproline	CC(C)[C@H](N)C(=O)N1C[C@H](O)C[C@H]1C(O)=O	2051.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Valylhydroxyproline,1TMS,isomer #1	CC(C)[C@H](N)C(=O)N1C[C@H](O[Si](C)(C)C)C[C@H]1C(=O)O	2007.3	Semi standard non polar	33892256
Valylhydroxyproline,1TMS,isomer #2	CC(C)[C@H](N)C(=O)N1C[C@H](O)C[C@H]1C(=O)O[Si](C)(C)C	1932.5	Semi standard non polar	33892256
Valylhydroxyproline,1TMS,isomer #3	CC(C)[C@H](N[Si](C)(C)C)C(=O)N1C[C@H](O)C[C@H]1C(=O)O	1994.6	Semi standard non polar	33892256
Valylhydroxyproline,2TMS,isomer #1	CC(C)[C@H](N)C(=O)N1C[C@H](O[Si](C)(C)C)C[C@H]1C(=O)O[Si](C)(C)C	1976.2	Semi standard non polar	33892256
Valylhydroxyproline,2TMS,isomer #2	CC(C)[C@H](N[Si](C)(C)C)C(=O)N1C[C@H](O[Si](C)(C)C)C[C@H]1C(=O)O	2015.8	Semi standard non polar	33892256
Valylhydroxyproline,2TMS,isomer #3	CC(C)[C@H](N[Si](C)(C)C)C(=O)N1C[C@H](O)C[C@H]1C(=O)O[Si](C)(C)C	1989.2	Semi standard non polar	33892256
Valylhydroxyproline,2TMS,isomer #4	CC(C)[C@@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2125.8	Semi standard non polar	33892256
Valylhydroxyproline,3TMS,isomer #1	CC(C)[C@H](N[Si](C)(C)C)C(=O)N1C[C@H](O[Si](C)(C)C)C[C@H]1C(=O)O[Si](C)(C)C	2001.3	Semi standard non polar	33892256
Valylhydroxyproline,3TMS,isomer #1	CC(C)[C@H](N[Si](C)(C)C)C(=O)N1C[C@H](O[Si](C)(C)C)C[C@H]1C(=O)O[Si](C)(C)C	2084.0	Standard non polar	33892256
Valylhydroxyproline,3TMS,isomer #2	CC(C)[C@@H](C(=O)N1C[C@H](O[Si](C)(C)C)C[C@H]1C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2180.2	Semi standard non polar	33892256
Valylhydroxyproline,3TMS,isomer #2	CC(C)[C@@H](C(=O)N1C[C@H](O[Si](C)(C)C)C[C@H]1C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2184.3	Standard non polar	33892256
Valylhydroxyproline,3TMS,isomer #3	CC(C)[C@@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2136.1	Semi standard non polar	33892256
Valylhydroxyproline,3TMS,isomer #3	CC(C)[C@@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2148.3	Standard non polar	33892256
Valylhydroxyproline,4TMS,isomer #1	CC(C)[C@@H](C(=O)N1C[C@H](O[Si](C)(C)C)C[C@H]1C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2212.9	Semi standard non polar	33892256
Valylhydroxyproline,4TMS,isomer #1	CC(C)[C@@H](C(=O)N1C[C@H](O[Si](C)(C)C)C[C@H]1C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2225.1	Standard non polar	33892256
Valylhydroxyproline,1TBDMS,isomer #1	CC(C)[C@H](N)C(=O)N1C[C@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C(=O)O	2241.5	Semi standard non polar	33892256
Valylhydroxyproline,1TBDMS,isomer #2	CC(C)[C@H](N)C(=O)N1C[C@H](O)C[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	2177.1	Semi standard non polar	33892256
Valylhydroxyproline,1TBDMS,isomer #3	CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N1C[C@H](O)C[C@H]1C(=O)O	2220.1	Semi standard non polar	33892256
Valylhydroxyproline,2TBDMS,isomer #1	CC(C)[C@H](N)C(=O)N1C[C@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	2444.6	Semi standard non polar	33892256
Valylhydroxyproline,2TBDMS,isomer #2	CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N1C[C@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C(=O)O	2478.5	Semi standard non polar	33892256
Valylhydroxyproline,2TBDMS,isomer #3	CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N1C[C@H](O)C[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	2440.1	Semi standard non polar	33892256
Valylhydroxyproline,2TBDMS,isomer #4	CC(C)[C@@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2564.0	Semi standard non polar	33892256
Valylhydroxyproline,3TBDMS,isomer #1	CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N1C[C@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	2685.6	Semi standard non polar	33892256
Valylhydroxyproline,3TBDMS,isomer #1	CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N1C[C@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	2646.9	Standard non polar	33892256
Valylhydroxyproline,3TBDMS,isomer #2	CC(C)[C@@H](C(=O)N1C[C@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2847.9	Semi standard non polar	33892256
Valylhydroxyproline,3TBDMS,isomer #2	CC(C)[C@@H](C(=O)N1C[C@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2773.9	Standard non polar	33892256
Valylhydroxyproline,3TBDMS,isomer #3	CC(C)[C@@H](C(=O)N1C[C@H](O)C[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	2787.9	Semi standard non polar	33892256
Valylhydroxyproline,3TBDMS,isomer #3	CC(C)[C@@H](C(=O)N1C[C@H](O)C[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	2745.1	Standard non polar	33892256
Valylhydroxyproline,4TBDMS,isomer #1	CC(C)[C@@H](C(=O)N1C[C@H](O[Si](C)(C)C(C)(C)C)C[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	3050.6	Semi standard non polar	33892256
Valylhydroxyproline,4TBDMS,isomer #1	CC(C)[C@@H](C(=O)N1C[C@H](O[Si](C)(C)C(C)(C)C)C[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	2931.9	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Valylhydroxyproline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Valylhydroxyproline 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 - Valylhydroxyproline 10V, Negative-QTOF	splash10-03fr-1390000000-3c46c88086cc3c91d521	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valylhydroxyproline 20V, Negative-QTOF	splash10-03di-0900000000-3dc3706a3d43434c78a9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valylhydroxyproline 40V, Negative-QTOF	splash10-0a5c-9300000000-9c7638217ff5d24c717c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valylhydroxyproline 10V, Positive-QTOF	splash10-001i-0490000000-816724819e08ffdda493	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valylhydroxyproline 20V, Positive-QTOF	splash10-01x0-9840000000-3be88dca75b2d426e9af	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valylhydroxyproline 40V, Positive-QTOF	splash10-0bu9-9200000000-a55b8aea8b38eff07cd7	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

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

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

FDB112130

KNApSAcK ID

Not Available

Chemspider ID

43627771

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10242944

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Valylhydroxyproline (HMDB0029128)

MOL for HMDB0029128 (Valylhydroxyproline)

3D MOL for HMDB0029128 (Valylhydroxyproline)

3D SDF for HMDB0029128 (Valylhydroxyproline)

3D-SDF for HMDB0029128 (Valylhydroxyproline)

PDB for HMDB0029128 (Valylhydroxyproline)

3D PDB for HMDB0029128 (Valylhydroxyproline)

SMILES for HMDB0029128 (Valylhydroxyproline)

INCHI for HMDB0029128 (Valylhydroxyproline)

Structure for HMDB0029128 (Valylhydroxyproline)

3D Structure for HMDB0029128 (Valylhydroxyproline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra