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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 21:03:34 UTC

Update Date

2021-09-14 15:19:03 UTC

HMDB ID

HMDB0029069

Secondary Accession Numbers

HMDB29069

Metabolite Identification

Common Name

Threonylproline

Description

Threonylproline is a dipeptide composed of threonine 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

HMDB0029069
     RDKit          3D
Threonylproline
 31 31  0  0  0  0  0  0  0  0999 V2000
    2.8161    1.1338   -0.8827 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8291    0.4584    0.4455 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8618    1.3805    1.4986 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6925   -0.5202    0.6435 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6350   -1.4686   -0.4111 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3907    0.1537    0.8037 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2330    0.9734    1.7848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6692   -0.0934   -0.1014 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6128   -0.9433   -1.2658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9103   -0.7102   -2.0148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8378   -0.4101   -0.8704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9769    0.4712    0.0074 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5676    0.4523    1.3555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0140   -0.1299    2.3002 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7670    1.1012    1.5637 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7519    2.2308   -0.7058 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8027    0.9920   -1.4133 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0505    0.7907   -1.5807 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7750   -0.1388    0.5369 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8588    0.8524    2.3517 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9439   -1.0938    1.5840 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3410   -1.3176   -1.1658 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5949   -2.4634   -0.0964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5984   -1.9910   -0.9423 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1863   -0.6628   -1.9891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2141   -1.5509   -2.6350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7979    0.2202   -2.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0782   -1.3670   -0.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7524    0.1095   -1.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0120    1.4909   -0.4479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9546    2.0497    1.2777 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  6
  3 20  1  0
  4 21  1  1
  5 22  1  0
  5 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  6
 15 31  1  0
M  END


  Mrv1652304062014162D          

 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  1  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 O   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
 9999.3583 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
  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
  3  5  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0029069

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H16N2O4/c1-5(12)7(10)8(13)11-4-2-3-6(11)9(14)15/h5-7,12H,2-4,10H2,1H3,(H,14,15)/t5-,6+,7+/m1/s1

> <INCHI_KEY>
QOLYAJSZHIJCTO-VQVTYTSYSA-N

> <FORMULA>
C9H16N2O4

> <MOLECULAR_WEIGHT>
216.237

> <EXACT_MASS>
216.111007003

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
21.32306012570097

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-2.64

> <JCHEM_LOGP>
-3.7379822353191408

> <ALOGPS_LOGS>
-0.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.705648566920292

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6113968623837645

> <JCHEM_PKA_STRONGEST_BASIC>
7.915007223758969

> <JCHEM_POLAR_SURFACE_AREA>
103.86

> <JCHEM_REFRACTIVITY>
51.446300000000015

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.09e+02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029069
     RDKit          3D
Threonylproline
 31 31  0  0  0  0  0  0  0  0999 V2000
    2.8161    1.1338   -0.8827 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8291    0.4584    0.4455 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8618    1.3805    1.4986 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6925   -0.5202    0.6435 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6350   -1.4686   -0.4111 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3907    0.1537    0.8037 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2330    0.9734    1.7848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6692   -0.0934   -0.1014 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6128   -0.9433   -1.2658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9103   -0.7102   -2.0148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8378   -0.4101   -0.8704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9769    0.4712    0.0074 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5676    0.4523    1.3555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0140   -0.1299    2.3002 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7670    1.1012    1.5637 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7519    2.2308   -0.7058 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8027    0.9920   -1.4133 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0505    0.7907   -1.5807 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7750   -0.1388    0.5369 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8588    0.8524    2.3517 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9439   -1.0938    1.5840 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3410   -1.3176   -1.1658 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5949   -2.4634   -0.0964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5984   -1.9910   -0.9423 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1863   -0.6628   -1.9891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2141   -1.5509   -2.6350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7979    0.2202   -2.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0782   -1.3670   -0.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7524    0.1095   -1.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0120    1.4909   -0.4479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9546    2.0497    1.2777 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  6
  3 20  1  0
  4 21  1  1
  5 22  1  0
  5 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  6
 15 31  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    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  O   UNK     0    8664.0648665.920   0.000  0.00  0.00           O+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    HMDB0029069
HETATM    1  C1  UNL     1       2.816   1.134  -0.883  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.829   0.458   0.445  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.862   1.381   1.499  1.00  0.00           O  
HETATM    4  C3  UNL     1       1.693  -0.520   0.643  1.00  0.00           C  
HETATM    5  N1  UNL     1       1.635  -1.469  -0.411  1.00  0.00           N  
HETATM    6  C4  UNL     1       0.391   0.154   0.804  1.00  0.00           C  
HETATM    7  O2  UNL     1       0.233   0.973   1.785  1.00  0.00           O  
HETATM    8  N2  UNL     1      -0.669  -0.093  -0.101  1.00  0.00           N  
HETATM    9  C5  UNL     1      -0.613  -0.943  -1.266  1.00  0.00           C  
HETATM   10  C6  UNL     1      -1.910  -0.710  -2.015  1.00  0.00           C  
HETATM   11  C7  UNL     1      -2.838  -0.410  -0.870  1.00  0.00           C  
HETATM   12  C8  UNL     1      -1.977   0.471   0.007  1.00  0.00           C  
HETATM   13  C9  UNL     1      -2.568   0.452   1.356  1.00  0.00           C  
HETATM   14  O3  UNL     1      -2.014  -0.130   2.300  1.00  0.00           O  
HETATM   15  O4  UNL     1      -3.767   1.101   1.564  1.00  0.00           O  
HETATM   16  H1  UNL     1       2.752   2.231  -0.706  1.00  0.00           H  
HETATM   17  H2  UNL     1       3.803   0.992  -1.413  1.00  0.00           H  
HETATM   18  H3  UNL     1       2.050   0.791  -1.581  1.00  0.00           H  
HETATM   19  H4  UNL     1       3.775  -0.139   0.537  1.00  0.00           H  
HETATM   20  H5  UNL     1       2.859   0.852   2.352  1.00  0.00           H  
HETATM   21  H6  UNL     1       1.944  -1.094   1.584  1.00  0.00           H  
HETATM   22  H7  UNL     1       2.341  -1.318  -1.166  1.00  0.00           H  
HETATM   23  H8  UNL     1       1.595  -2.463  -0.096  1.00  0.00           H  
HETATM   24  H9  UNL     1      -0.598  -1.991  -0.942  1.00  0.00           H  
HETATM   25  H10 UNL     1       0.186  -0.663  -1.989  1.00  0.00           H  
HETATM   26  H11 UNL     1      -2.214  -1.551  -2.635  1.00  0.00           H  
HETATM   27  H12 UNL     1      -1.798   0.220  -2.601  1.00  0.00           H  
HETATM   28  H13 UNL     1      -3.078  -1.367  -0.348  1.00  0.00           H  
HETATM   29  H14 UNL     1      -3.752   0.109  -1.218  1.00  0.00           H  
HETATM   30  H15 UNL     1      -2.012   1.491  -0.448  1.00  0.00           H  
HETATM   31  H16 UNL     1      -3.955   2.050   1.278  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    4   19
CONECT    3   20
CONECT    4    5    6   21
CONECT    5   22   23
CONECT    6    7    7    8
CONECT    8    9   12
CONECT    9   10   24   25
CONECT   10   11   26   27
CONECT   11   12   28   29
CONECT   12   13   30
CONECT   13   14   14   15
CONECT   15   31
END

HMDB0029069
     RDKit          3D
Threonylproline
 31 31  0  0  0  0  0  0  0  0999 V2000
    2.8161    1.1338   -0.8827 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8291    0.4584    0.4455 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8618    1.3805    1.4986 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6925   -0.5202    0.6435 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6350   -1.4686   -0.4111 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3907    0.1537    0.8037 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2330    0.9734    1.7848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6692   -0.0934   -0.1014 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6128   -0.9433   -1.2658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9103   -0.7102   -2.0148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8378   -0.4101   -0.8704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9769    0.4712    0.0074 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5676    0.4523    1.3555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0140   -0.1299    2.3002 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7670    1.1012    1.5637 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7519    2.2308   -0.7058 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8027    0.9920   -1.4133 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0505    0.7907   -1.5807 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7750   -0.1388    0.5369 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8588    0.8524    2.3517 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9439   -1.0938    1.5840 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3410   -1.3176   -1.1658 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5949   -2.4634   -0.0964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5984   -1.9910   -0.9423 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1863   -0.6628   -1.9891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2141   -1.5509   -2.6350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7979    0.2202   -2.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0782   -1.3670   -0.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7524    0.1095   -1.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0120    1.4909   -0.4479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9546    2.0497    1.2777 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  6
  3 20  1  0
  4 21  1  1
  5 22  1  0
  5 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  6
 15 31  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
L-THR-L-Pro	ChEBI
T-P	ChEBI
TP	ChEBI
L-Threoninyl-L-proline	HMDB
L-Threonyl-L-proline	HMDB
N-L-Threoninyl-L-proline	HMDB
N-L-Threonyl-L-proline	HMDB
N-Threoninylproline	HMDB
N-Threonylproline	HMDB
T-p Dipeptide	HMDB
TP Dipeptide	HMDB
THR-Pro	HMDB
Threonine proline dipeptide	HMDB
Threonine-proline dipeptide	HMDB
Threoninyl-proline	HMDB
Threoninylproline	HMDB
Threonyl-proline	HMDB
Threonylproline	ChEBI

Chemical Formula

C₉H₁₆N₂O₄

Average Molecular Weight

216.237

Monoisotopic Molecular Weight

216.111007003

IUPAC Name

(2S)-1-[(2S,3R)-2-amino-3-hydroxybutanoyl]pyrrolidine-2-carboxylic acid

Traditional Name

(2S)-1-[(2S,3R)-2-amino-3-hydroxybutanoyl]pyrrolidine-2-carboxylic acid

CAS Registry Number

46398-79-2

SMILES

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

InChI Identifier

InChI=1S/C9H16N2O4/c1-5(12)7(10)8(13)11-4-2-3-6(11)9(14)15/h5-7,12H,2-4,10H2,1H3,(H,14,15)/t5-,6+,7+/m1/s1

InChI Key

QOLYAJSZHIJCTO-VQVTYTSYSA-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
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
N-acylpyrrolidine
Pyrrolidine carboxylic acid or derivatives
Pyrrolidine carboxylic acid
Tertiary carboxylic acid amide
Pyrrolidine
Amino acid or derivatives
Carboxamide group
Amino acid
Secondary alcohol
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

dipeptide (CHEBI:73662 )

Ontology

Not Available

Endogenous (HMDB: HMDB0029069)

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	-3.74	Extrapolated

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	109 g/L	ALOGPS
logP	-2.6	ALOGPS
logP	-3.7	ChemAxon
logS	-0.3	ALOGPS
pKa (Strongest Acidic)	3.61	ChemAxon
pKa (Strongest Basic)	7.92	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	51.45 m³·mol⁻¹	ChemAxon
Polarizability	21.32 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]+	155.786	30932474
DeepCCS	[M-H]-	153.391	30932474
DeepCCS	[M-2H]-	186.421	30932474
DeepCCS	[M+Na]+	161.699	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.	1.46 minutes	32390414
Predicted by Siyang on May 30, 2022	9.3559 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	8.69 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	376.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	497.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	239.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	63.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	160.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	45.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	269.0 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	248.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	799.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	569.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	41.8 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	682.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	167.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	192.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	657.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	529.8 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	349.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Threonylproline	C[C@@H](O)[C@H](N)C(=O)N1CCC[C@H]1C(O)=O	2912.2	Standard polar	33892256
Threonylproline	C[C@@H](O)[C@H](N)C(=O)N1CCC[C@H]1C(O)=O	2004.4	Standard non polar	33892256
Threonylproline	C[C@@H](O)[C@H](N)C(=O)N1CCC[C@H]1C(O)=O	2082.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Threonylproline,1TMS,isomer #1	C[C@@H](O[Si](C)(C)C)[C@H](N)C(=O)N1CCC[C@H]1C(=O)O	1930.5	Semi standard non polar	33892256
Threonylproline,1TMS,isomer #2	C[C@@H](O)[C@H](N)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	1908.5	Semi standard non polar	33892256
Threonylproline,1TMS,isomer #3	C[C@@H](O)[C@H](N[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O	1937.1	Semi standard non polar	33892256
Threonylproline,2TMS,isomer #1	C[C@@H](O[Si](C)(C)C)[C@H](N)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	1967.4	Semi standard non polar	33892256
Threonylproline,2TMS,isomer #2	C[C@@H](O[Si](C)(C)C)[C@H](N[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O	1963.8	Semi standard non polar	33892256
Threonylproline,2TMS,isomer #3	C[C@@H](O)[C@H](N[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	1955.3	Semi standard non polar	33892256
Threonylproline,2TMS,isomer #4	C[C@@H](O)[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2053.7	Semi standard non polar	33892256
Threonylproline,3TMS,isomer #1	C[C@@H](O[Si](C)(C)C)[C@H](N[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	2005.2	Semi standard non polar	33892256
Threonylproline,3TMS,isomer #1	C[C@@H](O[Si](C)(C)C)[C@H](N[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	2068.8	Standard non polar	33892256
Threonylproline,3TMS,isomer #2	C[C@@H](O[Si](C)(C)C)[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2099.3	Semi standard non polar	33892256
Threonylproline,3TMS,isomer #2	C[C@@H](O[Si](C)(C)C)[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2140.4	Standard non polar	33892256
Threonylproline,3TMS,isomer #3	C[C@@H](O)[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2093.6	Semi standard non polar	33892256
Threonylproline,3TMS,isomer #3	C[C@@H](O)[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2127.8	Standard non polar	33892256
Threonylproline,4TMS,isomer #1	C[C@@H](O[Si](C)(C)C)[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2180.0	Semi standard non polar	33892256
Threonylproline,4TMS,isomer #1	C[C@@H](O[Si](C)(C)C)[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2185.9	Standard non polar	33892256
Threonylproline,1TBDMS,isomer #1	C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](N)C(=O)N1CCC[C@H]1C(=O)O	2162.7	Semi standard non polar	33892256
Threonylproline,1TBDMS,isomer #2	C[C@@H](O)[C@H](N)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	2147.9	Semi standard non polar	33892256
Threonylproline,1TBDMS,isomer #3	C[C@@H](O)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O	2167.9	Semi standard non polar	33892256
Threonylproline,2TBDMS,isomer #1	C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](N)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	2416.4	Semi standard non polar	33892256
Threonylproline,2TBDMS,isomer #2	C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O	2422.8	Semi standard non polar	33892256
Threonylproline,2TBDMS,isomer #3	C[C@@H](O)[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	2425.8	Semi standard non polar	33892256
Threonylproline,2TBDMS,isomer #4	C[C@@H](O)[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	2498.0	Semi standard non polar	33892256
Threonylproline,3TBDMS,isomer #1	C[C@@H](O[Si](C)(C)C(C)(C)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	2677.0	Semi standard non polar	33892256
Threonylproline,3TBDMS,isomer #1	C[C@@H](O[Si](C)(C)C(C)(C)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	2661.6	Standard non polar	33892256
Threonylproline,3TBDMS,isomer #2	C[C@@H](O[Si](C)(C)C(C)(C)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	2768.6	Semi standard non polar	33892256
Threonylproline,3TBDMS,isomer #2	C[C@@H](O[Si](C)(C)C(C)(C)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	2753.8	Standard non polar	33892256
Threonylproline,3TBDMS,isomer #3	C[C@@H](O)[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	2746.9	Semi standard non polar	33892256
Threonylproline,3TBDMS,isomer #3	C[C@@H](O)[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	2723.6	Standard non polar	33892256
Threonylproline,4TBDMS,isomer #1	C[C@@H](O[Si](C)(C)C(C)(C)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	3008.7	Semi standard non polar	33892256
Threonylproline,4TBDMS,isomer #1	C[C@@H](O[Si](C)(C)C(C)(C)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	2924.9	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Threonylproline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Threonylproline 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 - Threonylproline 10V, Negative-QTOF	splash10-03xr-1950000000-b476d1efb077df71407f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Threonylproline 20V, Negative-QTOF	splash10-03di-5900000000-0058cc3feb883a4c8a72	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Threonylproline 40V, Negative-QTOF	splash10-03dj-9500000000-9deb06937b7a1d319240	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Threonylproline 10V, Positive-QTOF	splash10-014i-2690000000-f96833175bb41bc9a6f4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Threonylproline 20V, Positive-QTOF	splash10-01ba-9510000000-61e327454cf5ce5872d5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Threonylproline 40V, Positive-QTOF	splash10-05fr-9000000000-f007533db9a2f2940e1b	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)	2021-09-25	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

FDB112075

KNApSAcK ID

Not Available

Chemspider ID

8010092

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9834371

PDB ID

Not Available

ChEBI ID

73662

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

Ishiguro K, Takamatsu M, Tomizawa K, Omori A, Takahashi M, Arioka M, Uchida T, Imahori K: Tau protein kinase I converts normal tau protein into A68-like component of paired helical filaments. J Biol Chem. 1992 May 25;267(15):10897-901. [PubMed:1587865 ]

Showing metabocard for Threonylproline (HMDB0029069)

MOL for HMDB0029069 (Threonylproline)

3D MOL for HMDB0029069 (Threonylproline)

3D SDF for HMDB0029069 (Threonylproline)

3D-SDF for HMDB0029069 (Threonylproline)

PDB for HMDB0029069 (Threonylproline)

3D PDB for HMDB0029069 (Threonylproline)

SMILES for HMDB0029069 (Threonylproline)

INCHI for HMDB0029069 (Threonylproline)

Structure for HMDB0029069 (Threonylproline)

3D Structure for HMDB0029069 (Threonylproline)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra