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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2008-10-29 15:22:48 UTC

Update Date

2022-09-22 18:34:20 UTC

HMDB ID

HMDB0011177

Secondary Accession Numbers

HMDB11177

Metabolite Identification

Common Name

Phenylalanylproline

Description

Phenylalanylproline, also known as FP or L-phe-L-pro, 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. Phenylalanylproline 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 phenylalanylproline a potential biomarker for the consumption of these foods. Phenylalanylproline is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on Phenylalanylproline.

Structure

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

HMDB0011177
     RDKit          3D
Phenylalanylproline
 37 38  0  0  0  0  0  0  0  0999 V2000
   -0.4910    0.0589    1.2937 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5147   -0.5853    0.0303 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5534    0.0832   -0.8635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9192    0.0221   -0.3150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3987    1.0395    0.4745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6810    1.0231    1.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4852   -0.0610    0.7465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0412   -1.1066   -0.0439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7653   -1.0452   -0.5602 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7597   -0.6074   -0.7019 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7490   -1.1190   -1.8833 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0117   -0.1303   -0.2620 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4489    0.4937    0.9654 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2279    1.6937    0.4133 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9639    1.1326   -0.7833 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2670   -0.1814   -1.0582 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0968   -1.3115   -0.6107 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1937   -1.5085   -1.1681 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7325   -2.1840    0.4052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6426    1.0730    1.1751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2047   -0.3307    1.9273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8567   -1.6461    0.1979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2650    1.1497   -0.9878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4747   -0.3805   -1.8570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8059    1.9142    0.7133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0321    1.8432    1.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4847   -0.0877    1.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6696   -1.9404   -0.2496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4241   -1.8780   -1.1844 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2080   -0.1637    1.4549 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6649    0.8011    1.6419 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9301    2.0486    1.2112 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5075    2.4847    0.1214 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8763    1.8009   -1.6658 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0429    0.9958   -0.5600 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9864   -0.2596   -2.1143 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0425   -3.1313    0.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  2 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
  9  4  1  0
 16 12  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  1
  3 23  1  0
  3 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  6
 19 37  1  0
M  END

                  
  Mrv1652304062012592D          

 19 20  0  0  0  0            999 V2000
 2500.7478 2500.2199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.0338 2500.6332    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2499.3114 2500.2323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.0338 2501.4576    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2501.4597 2500.6332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.1144 2499.3031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.8284 2498.8900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.1144 2500.1277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2497.8848 2501.8825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.1704 2501.4699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.1704 2500.6448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.8848 2500.2324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.5993 2500.6448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.5993 2501.4699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.7293 2499.3844    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2500.0619 2498.8993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3168 2498.1148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.1418 2498.1148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.3966 2498.8993    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  6  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14  9  1  0  0  0  0
  3 13  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 16  1  0  0  0  0
 15 19  1  0  0  0  0
 19  6  1  6  0  0  0
  1 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0011177

> <DATABASE_NAME>
hmdb

> <SMILES>
N[C@@H](CC1=CC=CC=C1)C(=O)N1CCC[C@H]1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H18N2O3/c15-11(9-10-5-2-1-3-6-10)13(17)16-8-4-7-12(16)14(18)19/h1-3,5-6,11-12H,4,7-9,15H2,(H,18,19)/t11-,12-/m0/s1

> <INCHI_KEY>
WEQJQNWXCSUVMA-RYUDHWBXSA-N

> <FORMULA>
C14H18N2O3

> <MOLECULAR_WEIGHT>
262.309

> <EXACT_MASS>
262.131742448

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
26.77952155321927

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.15

> <JCHEM_LOGP>
-1.4506579878025392

> <ALOGPS_LOGS>
-2.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7167540222523767

> <JCHEM_PKA_STRONGEST_BASIC>
8.002514644502652

> <JCHEM_POLAR_SURFACE_AREA>
83.63000000000001

> <JCHEM_REFRACTIVITY>
70.1028

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.11e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0011177
     RDKit          3D
Phenylalanylproline
 37 38  0  0  0  0  0  0  0  0999 V2000
   -0.4910    0.0589    1.2937 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5147   -0.5853    0.0303 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5534    0.0832   -0.8635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9192    0.0221   -0.3150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3987    1.0395    0.4745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6810    1.0231    1.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4852   -0.0610    0.7465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0412   -1.1066   -0.0439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7653   -1.0452   -0.5602 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7597   -0.6074   -0.7019 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7490   -1.1190   -1.8833 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0117   -0.1303   -0.2620 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4489    0.4937    0.9654 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2279    1.6937    0.4133 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9639    1.1326   -0.7833 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2670   -0.1814   -1.0582 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0968   -1.3115   -0.6107 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1937   -1.5085   -1.1681 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7325   -2.1840    0.4052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6426    1.0730    1.1751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2047   -0.3307    1.9273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8567   -1.6461    0.1979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2650    1.1497   -0.9878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4747   -0.3805   -1.8570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8059    1.9142    0.7133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0321    1.8432    1.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4847   -0.0877    1.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6696   -1.9404   -0.2496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4241   -1.8780   -1.1844 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2080   -0.1637    1.4549 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6649    0.8011    1.6419 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9301    2.0486    1.2112 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5075    2.4847    0.1214 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8763    1.8009   -1.6658 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0429    0.9958   -0.5600 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9864   -0.2596   -2.1143 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0425   -3.1313    0.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  2 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
  9  4  1  0
 16 12  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  1
  3 23  1  0
  3 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  6
 19 37  1  0
M  END

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  C   UNK     0    4668.0634667.077   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    4666.7304667.849   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    4665.3814667.100   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0    4666.7304669.388   0.000  0.00  0.00           N+0
HETATM    5  O   UNK     0    4669.3914667.849   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    4670.6144665.366   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    4671.9464664.595   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    4670.6144666.905   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0    4662.7184670.181   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    4661.3854669.410   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    4661.3854667.870   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    4662.7184667.100   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    4664.0524667.870   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    4664.0524669.410   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0    4668.0284665.518   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0    4666.7824664.612   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    4667.2584663.148   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    4668.7984663.148   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    4669.2744664.612   0.000  0.00  0.00           C+0
CONECT    1    2    5   15                                                  
CONECT    2    1    3    4                                                  
CONECT    3    2   13                                                       
CONECT    4    2                                                            
CONECT    5    1                                                            
CONECT    6    7    8   19                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9   10   14                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14    3                                                  
CONECT   14   13    9                                                       
CONECT   15   16   19    1                                                  
CONECT   16   17   15                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   15    6                                                  
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0011177
HETATM    1  N1  UNL     1      -0.491   0.059   1.294  1.00  0.00           N  
HETATM    2  C1  UNL     1      -0.515  -0.585   0.030  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.553   0.083  -0.864  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.919   0.022  -0.315  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.399   1.040   0.474  1.00  0.00           C  
HETATM    6  C5  UNL     1      -4.681   1.023   1.019  1.00  0.00           C  
HETATM    7  C6  UNL     1      -5.485  -0.061   0.747  1.00  0.00           C  
HETATM    8  C7  UNL     1      -5.041  -1.107  -0.044  1.00  0.00           C  
HETATM    9  C8  UNL     1      -3.765  -1.045  -0.560  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.760  -0.607  -0.702  1.00  0.00           C  
HETATM   11  O1  UNL     1       0.749  -1.119  -1.883  1.00  0.00           O  
HETATM   12  N2  UNL     1       2.012  -0.130  -0.262  1.00  0.00           N  
HETATM   13  C10 UNL     1       2.449   0.494   0.965  1.00  0.00           C  
HETATM   14  C11 UNL     1       3.228   1.694   0.413  1.00  0.00           C  
HETATM   15  C12 UNL     1       3.964   1.133  -0.783  1.00  0.00           C  
HETATM   16  C13 UNL     1       3.267  -0.181  -1.058  1.00  0.00           C  
HETATM   17  C14 UNL     1       4.097  -1.312  -0.611  1.00  0.00           C  
HETATM   18  O2  UNL     1       5.194  -1.509  -1.168  1.00  0.00           O  
HETATM   19  O3  UNL     1       3.733  -2.184   0.405  1.00  0.00           O  
HETATM   20  H1  UNL     1      -0.643   1.073   1.175  1.00  0.00           H  
HETATM   21  H2  UNL     1      -1.205  -0.331   1.927  1.00  0.00           H  
HETATM   22  H3  UNL     1      -0.857  -1.646   0.198  1.00  0.00           H  
HETATM   23  H4  UNL     1      -1.265   1.150  -0.988  1.00  0.00           H  
HETATM   24  H5  UNL     1      -1.475  -0.380  -1.857  1.00  0.00           H  
HETATM   25  H6  UNL     1      -2.806   1.914   0.713  1.00  0.00           H  
HETATM   26  H7  UNL     1      -5.032   1.843   1.641  1.00  0.00           H  
HETATM   27  H8  UNL     1      -6.485  -0.088   1.163  1.00  0.00           H  
HETATM   28  H9  UNL     1      -5.670  -1.940  -0.250  1.00  0.00           H  
HETATM   29  H10 UNL     1      -3.424  -1.878  -1.184  1.00  0.00           H  
HETATM   30  H11 UNL     1       3.208  -0.164   1.455  1.00  0.00           H  
HETATM   31  H12 UNL     1       1.665   0.801   1.642  1.00  0.00           H  
HETATM   32  H13 UNL     1       3.930   2.049   1.211  1.00  0.00           H  
HETATM   33  H14 UNL     1       2.507   2.485   0.121  1.00  0.00           H  
HETATM   34  H15 UNL     1       3.876   1.801  -1.666  1.00  0.00           H  
HETATM   35  H16 UNL     1       5.043   0.996  -0.560  1.00  0.00           H  
HETATM   36  H17 UNL     1       2.986  -0.260  -2.114  1.00  0.00           H  
HETATM   37  H18 UNL     1       4.042  -3.131   0.469  1.00  0.00           H  
CONECT    1    2   20   21
CONECT    2    3   10   22
CONECT    3    4   23   24
CONECT    4    5    5    9
CONECT    5    6   25
CONECT    6    7    7   26
CONECT    7    8   27
CONECT    8    9    9   28
CONECT    9   29
CONECT   10   11   11   12
CONECT   12   13   16
CONECT   13   14   30   31
CONECT   14   15   32   33
CONECT   15   16   34   35
CONECT   16   17   36
CONECT   17   18   18   19
CONECT   19   37
END

HMDB0011177
     RDKit          3D
Phenylalanylproline
 37 38  0  0  0  0  0  0  0  0999 V2000
   -0.4910    0.0589    1.2937 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5147   -0.5853    0.0303 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5534    0.0832   -0.8635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9192    0.0221   -0.3150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3987    1.0395    0.4745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6810    1.0231    1.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4852   -0.0610    0.7465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0412   -1.1066   -0.0439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7653   -1.0452   -0.5602 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7597   -0.6074   -0.7019 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7490   -1.1190   -1.8833 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0117   -0.1303   -0.2620 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4489    0.4937    0.9654 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2279    1.6937    0.4133 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9639    1.1326   -0.7833 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2670   -0.1814   -1.0582 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0968   -1.3115   -0.6107 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1937   -1.5085   -1.1681 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7325   -2.1840    0.4052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6426    1.0730    1.1751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2047   -0.3307    1.9273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8567   -1.6461    0.1979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2650    1.1497   -0.9878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4747   -0.3805   -1.8570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8059    1.9142    0.7133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0321    1.8432    1.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4847   -0.0877    1.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6696   -1.9404   -0.2496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4241   -1.8780   -1.1844 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2080   -0.1637    1.4549 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6649    0.8011    1.6419 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9301    2.0486    1.2112 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5075    2.4847    0.1214 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8763    1.8009   -1.6658 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0429    0.9958   -0.5600 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9864   -0.2596   -2.1143 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0425   -3.1313    0.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  2 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
  9  4  1  0
 16 12  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  1
  3 23  1  0
  3 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  6
 19 37  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
FP	ChEBI
L-Phe-L-pro	ChEBI
1-(3-Phenyl-L-alanyl)-proline	HMDB
1-L-Phenylalanyl-L-proline	HMDB
F-p Dipeptide	HMDB
FP Dipeptide	HMDB
L-1-(3-Phenyl-L-alanyl)-proline	HMDB
L-Phenylalanyl-L-proline	HMDB
Phe-pro	HMDB
Phenylalanine proline dipeptide	HMDB
Phenylalanine-proline dipeptide	HMDB
Phenylalanyl-proline	HMDB
Phenylalanylproline	ChEBI

Chemical Formula

C₁₄H₁₈N₂O₃

Average Molecular Weight

262.309

Monoisotopic Molecular Weight

262.131742448

IUPAC Name

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

Traditional Name

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

CAS Registry Number

7669-65-0

SMILES

N[C@@H](CC1=CC=CC=C1)C(=O)N1CCC[C@H]1C(O)=O

InChI Identifier

InChI=1S/C14H18N2O3/c15-11(9-10-5-2-1-3-6-10)13(17)16-8-4-7-12(16)14(18)19/h1-3,5-6,11-12H,4,7-9,15H2,(H,18,19)/t11-,12-/m0/s1

InChI Key

WEQJQNWXCSUVMA-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
Proline or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
N-acyl-l-alpha-amino acid
Alpha-amino acid amide
Alpha-amino acid or derivatives
Amphetamine or derivatives
N-acylpyrrolidine
Pyrrolidine carboxylic acid
Pyrrolidine carboxylic acid or derivatives
Aralkylamine
Monocyclic benzene moiety
Benzenoid
Pyrrolidine
Tertiary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Carboxylic acid salt
Amino acid
Organoheterocyclic compound
Carboxylic acid
Azacycle
Monocarboxylic acid or derivatives
Organic zwitterion
Organic nitrogen compound
Hydrocarbon derivative
Primary aliphatic amine
Organonitrogen compound
Amine
Organic oxygen compound
Carbonyl group
Organic oxide
Organopnictogen compound
Primary amine
Organooxygen compound
Organic salt
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

dipeptide (CHEBI:74750 )

Ontology

Not Available

Feces (PMID: 26709303)

Source

Endogenous

Endogenous (HMDB: HMDB0011177)

Exogenous

Food

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

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	2.11 g/L	ALOGPS
logP	-0.15	ALOGPS
logP	-1.5	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	3.72	ChemAxon
pKa (Strongest Basic)	8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.63 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	70.1 m³·mol⁻¹	ChemAxon
Polarizability	26.78 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]+	163.486	30932474
DeepCCS	[M-H]-	161.128	30932474
DeepCCS	[M-2H]-	194.014	30932474
DeepCCS	[M+Na]+	169.579	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]-	163.3	32859911
AllCCS	[M+Na-2H]-	163.3	32859911
AllCCS	[M+HCOO]-	163.5	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.	2.47 minutes	32390414
Predicted by Siyang on May 30, 2022	10.0693 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	6.15 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	223.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1073.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	223.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	125.0 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	92.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	292.4 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	322.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	681.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	724.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	287.3 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	948.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	209.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	241.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	394.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	379.6 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	114.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phenylalanylproline	N[C@@H](CC1=CC=CC=C1)C(=O)N1CCC[C@H]1C(O)=O	3435.3	Standard polar	33892256
Phenylalanylproline	N[C@@H](CC1=CC=CC=C1)C(=O)N1CCC[C@H]1C(O)=O	2352.5	Standard non polar	33892256
Phenylalanylproline	N[C@@H](CC1=CC=CC=C1)C(=O)N1CCC[C@H]1C(O)=O	2319.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Phenylalanylproline,1TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@@H](N)CC1=CC=CC=C1	2309.1	Semi standard non polar	33892256
Phenylalanylproline,1TMS,isomer #2	C[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N1CCC[C@H]1C(=O)O	2354.2	Semi standard non polar	33892256
Phenylalanylproline,2TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	2331.8	Semi standard non polar	33892256
Phenylalanylproline,2TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	2347.9	Standard non polar	33892256
Phenylalanylproline,2TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	2959.0	Standard polar	33892256
Phenylalanylproline,2TMS,isomer #2	C[Si](C)(C)N([C@@H](CC1=CC=CC=C1)C(=O)N1CCC[C@H]1C(=O)O)[Si](C)(C)C	2459.1	Semi standard non polar	33892256
Phenylalanylproline,2TMS,isomer #2	C[Si](C)(C)N([C@@H](CC1=CC=CC=C1)C(=O)N1CCC[C@H]1C(=O)O)[Si](C)(C)C	2403.4	Standard non polar	33892256
Phenylalanylproline,2TMS,isomer #2	C[Si](C)(C)N([C@@H](CC1=CC=CC=C1)C(=O)N1CCC[C@H]1C(=O)O)[Si](C)(C)C	3141.3	Standard polar	33892256
Phenylalanylproline,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C	2477.9	Semi standard non polar	33892256
Phenylalanylproline,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C	2451.0	Standard non polar	33892256
Phenylalanylproline,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C	2817.1	Standard polar	33892256
Phenylalanylproline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@@H](N)CC1=CC=CC=C1	2542.9	Semi standard non polar	33892256
Phenylalanylproline,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N1CCC[C@H]1C(=O)O	2568.9	Semi standard non polar	33892256
Phenylalanylproline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	2801.7	Semi standard non polar	33892256
Phenylalanylproline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	2735.7	Standard non polar	33892256
Phenylalanylproline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3137.6	Standard polar	33892256
Phenylalanylproline,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N([C@@H](CC1=CC=CC=C1)C(=O)N1CCC[C@H]1C(=O)O)[Si](C)(C)C(C)(C)C	2912.1	Semi standard non polar	33892256
Phenylalanylproline,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N([C@@H](CC1=CC=CC=C1)C(=O)N1CCC[C@H]1C(=O)O)[Si](C)(C)C(C)(C)C	2793.2	Standard non polar	33892256
Phenylalanylproline,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N([C@@H](CC1=CC=CC=C1)C(=O)N1CCC[C@H]1C(=O)O)[Si](C)(C)C(C)(C)C	3230.7	Standard polar	33892256
Phenylalanylproline,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3127.1	Semi standard non polar	33892256
Phenylalanylproline,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3019.6	Standard non polar	33892256
Phenylalanylproline,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3074.7	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Urine

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)	Female	Normal	26709303	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Both	Normal	25486321	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

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

FDB111640

KNApSAcK ID

Not Available

Chemspider ID

5383590

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7020641

PDB ID

Not Available

ChEBI ID

74750

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 Phenylalanylproline (HMDB0011177)

MOL for HMDB0011177 (Phenylalanylproline)

3D MOL for HMDB0011177 (Phenylalanylproline)

3D SDF for HMDB0011177 (Phenylalanylproline)

3D-SDF for HMDB0011177 (Phenylalanylproline)

PDB for HMDB0011177 (Phenylalanylproline)

3D PDB for HMDB0011177 (Phenylalanylproline)

SMILES for HMDB0011177 (Phenylalanylproline)

INCHI for HMDB0011177 (Phenylalanylproline)

Structure for HMDB0011177 (Phenylalanylproline)

3D Structure for HMDB0011177 (Phenylalanylproline)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized