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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2008-10-29 15:23:30 UTC

Update Date

2021-09-14 15:45:34 UTC

HMDB ID

HMDB0011179

Secondary Accession Numbers

HMDB11179

Metabolite Identification

Common Name

Prolylphenylalanine

Description

Prolylphenylalanine is a dipeptide composed of proline and phenylalanine. It is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. It is found in urine (PMID: 3782411 ).

Structure

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

HMDB0011179
     RDKit          3D
Prolylphenylalanine
 37 38  0  0  0  0  0  0  0  0999 V2000
   -0.2068   -2.1498   -1.1613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9476   -1.4884   -0.3917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1350   -2.0913    0.0377 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5532   -0.1349    0.0248 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5222    0.8685   -0.5017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9054    0.6915   -0.0605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3655    1.2706    1.1162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6672    1.1060    1.5205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5515    0.3694    0.7818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1243   -0.2203   -0.3955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7970   -0.0486   -0.8016 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7458    0.1663   -0.5833 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8689    0.4982    0.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7268    0.5289    1.4709 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1538    0.7929   -0.4352 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6793   -0.4348   -1.1912 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3660   -1.1672   -0.0307 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0561   -0.0082    0.6533 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1676    1.1066    0.5389 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1489   -3.0775    0.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4372   -0.0469    1.1255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1751    1.8961   -0.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4809    0.8093   -1.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6552    1.8477    1.6863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0293    1.5581    2.4405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5704    0.2607    1.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8233   -0.7980   -0.9717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4805   -0.5120   -1.7268 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8149    0.1281   -1.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0144    1.5732   -1.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8724   -1.0145   -1.6334 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4492   -0.0888   -1.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5903   -1.5430    0.6651 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0498   -1.9396   -0.3872 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9769    0.2233    0.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2924   -0.2776    1.7026 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7520    1.3463    1.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  4 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 11  6  1  0
 19 15  1  0
  3 20  1  0
  4 21  1  1
  5 22  1  0
  5 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 15 30  1  6
 16 31  1  0
 16 32  1  0
 17 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
M  END


  Mrv1652305161920152D          

 19 20  0  0  0  0            999 V2000
 2501.0250 2499.5612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3109 2499.9744    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2499.5968 2499.5612    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2498.8828 2499.9744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.8828 2500.7990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3109 2500.7990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.0250 2501.2101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2499.5968 2501.2101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2497.4977 2500.0555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2496.8303 2499.5705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.0852 2498.7859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.9102 2498.7859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.1651 2499.5705    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2503.1682 2500.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.4538 2501.2113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.7393 2500.7988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.7392 2499.9738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.4537 2499.5613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.1683 2499.9739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  4  5  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 10  1  0  0  0  0
  9 13  1  0  0  0  0
 13  4  1  6  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 14  1  0  0  0  0
  1 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0011179

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@@H]1CCCN1

> <INCHI_IDENTIFIER>
InChI=1S/C14H18N2O3/c17-13(11-7-4-8-15-11)16-12(14(18)19)9-10-5-2-1-3-6-10/h1-3,5-6,11-12,15H,4,7-9H2,(H,16,17)(H,18,19)/t11-,12-/m0/s1

> <INCHI_KEY>
IWIANZLCJVYEFX-RYUDHWBXSA-N

> <FORMULA>
C14H18N2O3

> <MOLECULAR_WEIGHT>
262.309

> <EXACT_MASS>
262.131742448

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
27.58882487853184

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-3-phenyl-2-{[(2S)-pyrrolidin-2-yl]formamido}propanoic acid

> <ALOGPS_LOGP>
-1.26

> <JCHEM_LOGP>
-1.4495372005460359

> <ALOGPS_LOGS>
-2.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.563718789077761

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.776881190856318

> <JCHEM_PKA_STRONGEST_BASIC>
9.806117414115185

> <JCHEM_POLAR_SURFACE_AREA>
78.43

> <JCHEM_REFRACTIVITY>
69.98070000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.29e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-3-phenyl-2-[(2S)-pyrrolidin-2-ylformamido]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0011179
     RDKit          3D
Prolylphenylalanine
 37 38  0  0  0  0  0  0  0  0999 V2000
   -0.2068   -2.1498   -1.1613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9476   -1.4884   -0.3917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1350   -2.0913    0.0377 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5532   -0.1349    0.0248 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5222    0.8685   -0.5017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9054    0.6915   -0.0605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3655    1.2706    1.1162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6672    1.1060    1.5205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5515    0.3694    0.7818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1243   -0.2203   -0.3955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7970   -0.0486   -0.8016 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7458    0.1663   -0.5833 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8689    0.4982    0.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7268    0.5289    1.4709 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1538    0.7929   -0.4352 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6793   -0.4348   -1.1912 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3660   -1.1672   -0.0307 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0561   -0.0082    0.6533 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1676    1.1066    0.5389 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1489   -3.0775    0.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4372   -0.0469    1.1255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1751    1.8961   -0.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4809    0.8093   -1.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6552    1.8477    1.6863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0293    1.5581    2.4405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5704    0.2607    1.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8233   -0.7980   -0.9717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4805   -0.5120   -1.7268 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8149    0.1281   -1.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0144    1.5732   -1.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8724   -1.0145   -1.6334 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4492   -0.0888   -1.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5903   -1.5430    0.6651 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0498   -1.9396   -0.3872 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9769    0.2233    0.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2924   -0.2776    1.7026 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7520    1.3463    1.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  4 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 11  6  1  0
 19 15  1  0
  3 20  1  0
  4 21  1  1
  5 22  1  0
  5 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 15 30  1  6
 16 31  1  0
 16 32  1  0
 17 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
M  END

HEADER    PROTEIN                                 16-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-MAY-19         0                                  
HETATM    1  C   UNK     0    4668.5804665.848   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    4667.2474666.619   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0    4665.9144665.848   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0    4664.5814666.619   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    4664.5814668.158   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    4667.2474668.158   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    4668.5804668.926   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    4665.9144668.926   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0    4661.9964666.770   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0    4660.7504665.865   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    4661.2264664.400   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    4662.7664664.400   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    4663.2424665.865   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    4672.5814668.158   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    4671.2474668.928   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    4669.9134668.158   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    4669.9134666.618   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    4671.2474665.848   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    4672.5814666.618   0.000  0.00  0.00           C+0
CONECT    1    2   17                                                       
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   13                                                  
CONECT    5    4                                                            
CONECT    6    2    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9   10   13                                                       
CONECT   10   11    9                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    9    4                                                  
CONECT   14   15   19                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18    1                                                  
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0011179
HETATM    1  O1  UNL     1      -0.207  -2.150  -1.161  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.948  -1.488  -0.392  1.00  0.00           C  
HETATM    3  O2  UNL     1      -2.135  -2.091   0.038  1.00  0.00           O  
HETATM    4  C2  UNL     1      -0.553  -0.135   0.025  1.00  0.00           C  
HETATM    5  C3  UNL     1      -1.522   0.869  -0.502  1.00  0.00           C  
HETATM    6  C4  UNL     1      -2.905   0.691  -0.060  1.00  0.00           C  
HETATM    7  C5  UNL     1      -3.365   1.271   1.116  1.00  0.00           C  
HETATM    8  C6  UNL     1      -4.667   1.106   1.521  1.00  0.00           C  
HETATM    9  C7  UNL     1      -5.552   0.369   0.782  1.00  0.00           C  
HETATM   10  C8  UNL     1      -5.124  -0.220  -0.395  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.797  -0.049  -0.802  1.00  0.00           C  
HETATM   12  N1  UNL     1       0.746   0.166  -0.583  1.00  0.00           N  
HETATM   13  C10 UNL     1       1.869   0.498   0.222  1.00  0.00           C  
HETATM   14  O3  UNL     1       1.727   0.529   1.471  1.00  0.00           O  
HETATM   15  C11 UNL     1       3.154   0.793  -0.435  1.00  0.00           C  
HETATM   16  C12 UNL     1       3.679  -0.435  -1.191  1.00  0.00           C  
HETATM   17  C13 UNL     1       4.366  -1.167  -0.031  1.00  0.00           C  
HETATM   18  C14 UNL     1       5.056  -0.008   0.653  1.00  0.00           C  
HETATM   19  N2  UNL     1       4.168   1.107   0.539  1.00  0.00           N  
HETATM   20  H1  UNL     1      -2.149  -3.077   0.175  1.00  0.00           H  
HETATM   21  H2  UNL     1      -0.437  -0.047   1.125  1.00  0.00           H  
HETATM   22  H3  UNL     1      -1.175   1.896  -0.192  1.00  0.00           H  
HETATM   23  H4  UNL     1      -1.481   0.809  -1.627  1.00  0.00           H  
HETATM   24  H5  UNL     1      -2.655   1.848   1.686  1.00  0.00           H  
HETATM   25  H6  UNL     1      -5.029   1.558   2.441  1.00  0.00           H  
HETATM   26  H7  UNL     1      -6.570   0.261   1.131  1.00  0.00           H  
HETATM   27  H8  UNL     1      -5.823  -0.798  -0.972  1.00  0.00           H  
HETATM   28  H9  UNL     1      -3.481  -0.512  -1.727  1.00  0.00           H  
HETATM   29  H10 UNL     1       0.815   0.128  -1.627  1.00  0.00           H  
HETATM   30  H11 UNL     1       3.014   1.573  -1.203  1.00  0.00           H  
HETATM   31  H12 UNL     1       2.872  -1.015  -1.633  1.00  0.00           H  
HETATM   32  H13 UNL     1       4.449  -0.089  -1.897  1.00  0.00           H  
HETATM   33  H14 UNL     1       3.590  -1.543   0.665  1.00  0.00           H  
HETATM   34  H15 UNL     1       5.050  -1.940  -0.387  1.00  0.00           H  
HETATM   35  H16 UNL     1       5.977   0.223   0.066  1.00  0.00           H  
HETATM   36  H17 UNL     1       5.292  -0.278   1.703  1.00  0.00           H  
HETATM   37  H18 UNL     1       3.752   1.346   1.459  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   20
CONECT    4    5   12   21
CONECT    5    6   22   23
CONECT    6    7    7   11
CONECT    7    8   24
CONECT    8    9    9   25
CONECT    9   10   26
CONECT   10   11   11   27
CONECT   11   28
CONECT   12   13   29
CONECT   13   14   14   15
CONECT   15   16   19   30
CONECT   16   17   31   32
CONECT   17   18   33   34
CONECT   18   19   35   36
CONECT   19   37
END

HMDB0011179
     RDKit          3D
Prolylphenylalanine
 37 38  0  0  0  0  0  0  0  0999 V2000
   -0.2068   -2.1498   -1.1613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9476   -1.4884   -0.3917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1350   -2.0913    0.0377 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5532   -0.1349    0.0248 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5222    0.8685   -0.5017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9054    0.6915   -0.0605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3655    1.2706    1.1162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6672    1.1060    1.5205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5515    0.3694    0.7818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1243   -0.2203   -0.3955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7970   -0.0486   -0.8016 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7458    0.1663   -0.5833 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8689    0.4982    0.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7268    0.5289    1.4709 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1538    0.7929   -0.4352 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6793   -0.4348   -1.1912 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3660   -1.1672   -0.0307 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0561   -0.0082    0.6533 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1676    1.1066    0.5389 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1489   -3.0775    0.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4372   -0.0469    1.1255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1751    1.8961   -0.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4809    0.8093   -1.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6552    1.8477    1.6863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0293    1.5581    2.4405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5704    0.2607    1.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8233   -0.7980   -0.9717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4805   -0.5120   -1.7268 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8149    0.1281   -1.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0144    1.5732   -1.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8724   -1.0145   -1.6334 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4492   -0.0888   -1.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5903   -1.5430    0.6651 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0498   -1.9396   -0.3872 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9769    0.2233    0.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2924   -0.2776    1.7026 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7520    1.3463    1.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  4 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 11  6  1  0
 19 15  1  0
  3 20  1  0
  4 21  1  1
  5 22  1  0
  5 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 15 30  1  6
 16 31  1  0
 16 32  1  0
 17 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
L-Pro-L-phe	ChEBI
PF	ChEBI
L-Prolyl-L-phenylalanine	HMDB
N-L-Prolyl-L-phenylalanine	HMDB
N-Prolylphenylalanine	HMDB
p-F Dipeptide	HMDB
PF Dipeptide	HMDB
Pro-phe	HMDB
Proline phenylalanine dipeptide	HMDB
Proline-phenylalanine dipeptide	HMDB
Prolyl-phenylalanine	HMDB
Prolylphenylalanine	ChEBI

Chemical Formula

C₁₄H₁₈N₂O₃

Average Molecular Weight

262.309

Monoisotopic Molecular Weight

262.131742448

IUPAC Name

(2S)-3-phenyl-2-{[(2S)-pyrrolidin-2-yl]formamido}propanoic acid

Traditional Name

(2S)-3-phenyl-2-[(2S)-pyrrolidin-2-ylformamido]propanoic acid

CAS Registry Number

13589-02-1

SMILES

OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@@H]1CCCN1

InChI Identifier

InChI=1S/C14H18N2O3/c17-13(11-7-4-8-15-11)16-12(14(18)19)9-10-5-2-1-3-6-10/h1-3,5-6,11-12,15H,4,7-9H2,(H,16,17)(H,18,19)/t11-,12-/m0/s1

InChI Key

IWIANZLCJVYEFX-RYUDHWBXSA-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
Phenylalanine or derivatives
N-acyl-alpha-amino acid
Proline or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-l-alpha-amino acid
Alpha-amino acid amide
3-phenylpropanoic-acid
Alpha-amino acid or derivatives
Amphetamine or derivatives
Pyrrolidine carboxylic acid or derivatives
Pyrrolidine-2-carboxamide
Benzenoid
Monocyclic benzene moiety
Pyrrolidine
Secondary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Amino acid
Secondary amine
Azacycle
Organoheterocyclic compound
Carboxylic acid
Monocarboxylic acid or derivatives
Secondary aliphatic amine
Organic oxygen compound
Organic oxide
Organonitrogen compound
Carbonyl group
Organooxygen compound
Organopnictogen compound
Hydrocarbon derivative
Amine
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

dipeptide (CHEBI:74795 )

Ontology

Not Available

Feces (PMID: 27015276)

Source

Endogenous

Endogenous (HMDB: HMDB0011179)

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	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.73 g/L	ALOGPS
logP	-1.3	ALOGPS
logP	-1.4	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	3.78	ChemAxon
pKa (Strongest Basic)	9.81	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	78.43 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	69.98 m³·mol⁻¹	ChemAxon
Polarizability	27.59 Å³	ChemAxon
Number of Rings	2	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]+	160.676	30932474
DeepCCS	[M-H]-	158.318	30932474
DeepCCS	[M-2H]-	191.751	30932474
DeepCCS	[M+Na]+	166.978	30932474
AllCCS	[M+H]+	161.9	32859911
AllCCS	[M+H-H2O]+	158.3	32859911
AllCCS	[M+NH4]+	165.2	32859911
AllCCS	[M+Na]+	166.2	32859911
AllCCS	[M-H]-	163.2	32859911
AllCCS	[M+Na-2H]-	163.2	32859911
AllCCS	[M+HCOO]-	163.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.63 minutes	32390414
Predicted by Siyang on May 30, 2022	9.933 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.83 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	187.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1113.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	220.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	121.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	168.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	87.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	281.3 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	317.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	635.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	728.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	335.2 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	958.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	204.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	234.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	414.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	342.0 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	96.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Prolylphenylalanine	OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@@H]1CCCN1	3616.3	Standard polar	33892256
Prolylphenylalanine	OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@@H]1CCCN1	2338.7	Standard non polar	33892256
Prolylphenylalanine	OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@@H]1CCCN1	2346.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Prolylphenylalanine,1TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@@H]1CCCN1	2340.0	Semi standard non polar	33892256
Prolylphenylalanine,1TMS,isomer #2	C[Si](C)(C)N(C(=O)[C@@H]1CCCN1)[C@@H](CC1=CC=CC=C1)C(=O)O	2313.6	Semi standard non polar	33892256
Prolylphenylalanine,1TMS,isomer #3	C[Si](C)(C)N1CCC[C@H]1C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O	2341.0	Semi standard non polar	33892256
Prolylphenylalanine,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@@H]1CCCN1)[Si](C)(C)C	2251.7	Semi standard non polar	33892256
Prolylphenylalanine,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@@H]1CCCN1)[Si](C)(C)C	2277.7	Standard non polar	33892256
Prolylphenylalanine,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@@H]1CCCN1)[Si](C)(C)C	3051.9	Standard polar	33892256
Prolylphenylalanine,2TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@@H]1CCCN1[Si](C)(C)C	2286.8	Semi standard non polar	33892256
Prolylphenylalanine,2TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@@H]1CCCN1[Si](C)(C)C	2313.3	Standard non polar	33892256
Prolylphenylalanine,2TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@@H]1CCCN1[Si](C)(C)C	3037.1	Standard polar	33892256
Prolylphenylalanine,2TMS,isomer #3	C[Si](C)(C)N1CCC[C@H]1C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	2277.0	Semi standard non polar	33892256
Prolylphenylalanine,2TMS,isomer #3	C[Si](C)(C)N1CCC[C@H]1C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	2351.2	Standard non polar	33892256
Prolylphenylalanine,2TMS,isomer #3	C[Si](C)(C)N1CCC[C@H]1C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	3053.0	Standard polar	33892256
Prolylphenylalanine,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@@H]1CCCN1[Si](C)(C)C)[Si](C)(C)C	2289.9	Semi standard non polar	33892256
Prolylphenylalanine,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@@H]1CCCN1[Si](C)(C)C)[Si](C)(C)C	2374.3	Standard non polar	33892256
Prolylphenylalanine,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@@H]1CCCN1[Si](C)(C)C)[Si](C)(C)C	2819.6	Standard polar	33892256
Prolylphenylalanine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@@H]1CCCN1	2588.4	Semi standard non polar	33892256
Prolylphenylalanine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(=O)[C@@H]1CCCN1)[C@@H](CC1=CC=CC=C1)C(=O)O	2551.4	Semi standard non polar	33892256
Prolylphenylalanine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1CCC[C@H]1C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O	2559.0	Semi standard non polar	33892256
Prolylphenylalanine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@@H]1CCCN1)[Si](C)(C)C(C)(C)C	2752.3	Semi standard non polar	33892256
Prolylphenylalanine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@@H]1CCCN1)[Si](C)(C)C(C)(C)C	2679.0	Standard non polar	33892256
Prolylphenylalanine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@@H]1CCCN1)[Si](C)(C)C(C)(C)C	3205.0	Standard polar	33892256
Prolylphenylalanine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@@H]1CCCN1[Si](C)(C)C(C)(C)C	2789.0	Semi standard non polar	33892256
Prolylphenylalanine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@@H]1CCCN1[Si](C)(C)C(C)(C)C	2724.3	Standard non polar	33892256
Prolylphenylalanine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@@H]1CCCN1[Si](C)(C)C(C)(C)C	3223.1	Standard polar	33892256
Prolylphenylalanine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1CCC[C@H]1C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	2768.9	Semi standard non polar	33892256
Prolylphenylalanine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1CCC[C@H]1C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	2731.8	Standard non polar	33892256
Prolylphenylalanine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1CCC[C@H]1C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	3229.0	Standard polar	33892256
Prolylphenylalanine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@@H]1CCCN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2982.0	Semi standard non polar	33892256
Prolylphenylalanine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@@H]1CCCN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2950.3	Standard non polar	33892256
Prolylphenylalanine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@@H]1CCCN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3112.0	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

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

Abnormal Concentrations

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

Associated Disorders and Diseases

Disease References

Colorectal cancer

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

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4894402

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6351946

PDB ID

Not Available

ChEBI ID

74795

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Jandke J, Spiteller G: Dipeptide analysis in human urine. J Chromatogr. 1986 Oct 31;382:39-45. [PubMed:3782411 ]

Showing metabocard for Prolylphenylalanine (HMDB0011179)

MOL for HMDB0011179 (Prolylphenylalanine)

3D MOL for HMDB0011179 (Prolylphenylalanine)

3D SDF for HMDB0011179 (Prolylphenylalanine)

3D-SDF for HMDB0011179 (Prolylphenylalanine)

PDB for HMDB0011179 (Prolylphenylalanine)

3D PDB for HMDB0011179 (Prolylphenylalanine)

SMILES for HMDB0011179 (Prolylphenylalanine)

INCHI for HMDB0011179 (Prolylphenylalanine)

Structure for HMDB0011179 (Prolylphenylalanine)

3D Structure for HMDB0011179 (Prolylphenylalanine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized