Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

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

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 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

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Phenylalanylproline 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 - Phenylalanylproline 10V, Positive-QTOF	splash10-03dj-0290000000-ecf7bc2235340969f7bc	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylalanylproline 20V, Positive-QTOF	splash10-0fka-3940000000-1713a14aa8b8795c344b	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylalanylproline 40V, Positive-QTOF	splash10-00r6-9500000000-40b0c052b5f89ad3d5ae	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylalanylproline 10V, Negative-QTOF	splash10-03xr-0090000000-9c05820887e0ef0bc9d0	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylalanylproline 20V, Negative-QTOF	splash10-02t9-3390000000-aee039d9ff42f5383851	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylalanylproline 40V, Negative-QTOF	splash10-044m-8900000000-75a30a6e0b0565cdd569	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylalanylproline 10V, Negative-QTOF	splash10-03di-0190000000-c61bd120c2297af4869a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylalanylproline 20V, Negative-QTOF	splash10-03di-4970000000-1e3a2e147807c341713b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylalanylproline 40V, Negative-QTOF	splash10-03dm-9600000000-9fe04b81df6f93bb1ee8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylalanylproline 10V, Positive-QTOF	splash10-03dj-0390000000-0e5cdd9a879acb7ec178	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylalanylproline 20V, Positive-QTOF	splash10-006x-9820000000-c79514d6ca855800719d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylalanylproline 40V, Positive-QTOF	splash10-00fu-9600000000-d628918c604e71656d95	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

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

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

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	Not Specified	Both	Normal	25486321	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	26709303	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 Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra