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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2008-10-29 15:22:29 UTC

Update Date

2021-09-14 15:37:04 UTC

HMDB ID

HMDB0011176

Secondary Accession Numbers

HMDB0028996
HMDB11176
HMDB28996

Metabolite Identification

Common Name

Phenylalanylhydroxyproline

Description

Phenylalanylhydroxyproline is a proteolytic breakdown product of collagen. It belongs to the family of peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by the formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. It is found in urine (PMID: 3782411 ).

Structure

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

HMDB0011176
     RDKit          3D
Phenylalanylhydroxyproline
 38 39  0  0  0  0  0  0  0  0999 V2000
    1.6754   -2.5796   -0.2200 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5043   -1.7991    0.1920 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8596   -1.0512    1.4814 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0123   -0.1478    1.2516 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2839   -0.6313    1.4550 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3798    0.2075    1.2427 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1856    1.5124    0.8315 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9172    2.0066    0.6249 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8359    1.1532    0.8424 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0901   -0.8618   -0.8716 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9328   -0.6040   -1.7829 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1967   -0.2916   -0.8513 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6975    0.6911   -1.8415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6114    1.5911   -1.0329 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0528    2.8743   -0.8893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6074    0.9989    0.3873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3394   -0.4588    0.0050 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5003   -1.0725   -0.6564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5424   -1.2247    0.0331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5287   -1.4877   -1.9591 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1068   -2.1127   -1.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3651   -3.5425   -0.4351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3231   -2.4740    0.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0853   -1.8248    2.2313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0135   -0.5019    1.8044 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4480   -1.6564    1.7785 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3720   -0.1963    1.4096 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0749    2.1297    0.6788 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7884    3.0323    0.3028 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8328    1.5331    0.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7858    1.2978   -2.1183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1571    0.2261   -2.7063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6309    1.6353   -1.4390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0936    3.1963    0.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7801    1.3971    0.9909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6003    1.1122    0.8273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0674   -1.0375    0.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2216   -1.0392   -2.5748 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
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  9  4  1  0
 17 12  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  1
  3 24  1  0
  3 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  6
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  1
 20 38  1  0
M  END


  Mrv1652307191923482D          

 20 21  0  0  0  0            999 V2000
10002.1009 9999.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.8128 9999.2054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.100910000.4412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.8095 9997.7700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.7175 9999.7002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10000.0502 9999.2152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3051 9998.4306    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.1301 9998.4306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.3850 9999.2152    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.717510000.5252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.003110000.9377    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.432010000.9377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.288610000.5252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.003110001.7627    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9998.574110000.9377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.574110001.7626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.859610002.1752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.145110001.7627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.145110000.9377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.859610000.5251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  7  4  1  1  0  0  0
  9  1  1  6  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  6  0  0  0
 10 12  2  0  0  0  0
 13 15  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 16  2  0  0  0  0
 20 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0011176

> <DATABASE_NAME>
hmdb

> <SMILES>
N[C@@H](CC1=CC=CC=C1)C(=O)N1C[C@H](O)C[C@H]1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H18N2O4/c15-11(6-9-4-2-1-3-5-9)13(18)16-8-10(17)7-12(16)14(19)20/h1-5,10-12,17H,6-8,15H2,(H,19,20)/t10-,11+,12+/m1/s1

> <INCHI_KEY>
WJSNJMXOBDSZDL-WOPDTQHZSA-N

> <FORMULA>
C14H18N2O4

> <MOLECULAR_WEIGHT>
278.308

> <EXACT_MASS>
278.126657068

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
27.872331410774017

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.70

> <JCHEM_LOGP>
-2.598927908714749

> <ALOGPS_LOGS>
-2.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.826415508167337

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.587015356435035

> <JCHEM_PKA_STRONGEST_BASIC>
8.002459091033767

> <JCHEM_POLAR_SURFACE_AREA>
103.86

> <JCHEM_REFRACTIVITY>
71.42070000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.72e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0011176
     RDKit          3D
Phenylalanylhydroxyproline
 38 39  0  0  0  0  0  0  0  0999 V2000
    1.6754   -2.5796   -0.2200 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5043   -1.7991    0.1920 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8596   -1.0512    1.4814 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0123   -0.1478    1.2516 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2839   -0.6313    1.4550 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3798    0.2075    1.2427 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1856    1.5124    0.8315 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9172    2.0066    0.6249 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8359    1.1532    0.8424 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0901   -0.8618   -0.8716 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9328   -0.6040   -1.7829 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1967   -0.2916   -0.8513 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6975    0.6911   -1.8415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6114    1.5911   -1.0329 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0528    2.8743   -0.8893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6074    0.9989    0.3873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3394   -0.4588    0.0050 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5003   -1.0725   -0.6564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5424   -1.2247    0.0331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5287   -1.4877   -1.9591 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1068   -2.1127   -1.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3651   -3.5425   -0.4351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3231   -2.4740    0.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0853   -1.8248    2.2313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0135   -0.5019    1.8044 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4480   -1.6564    1.7785 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3720   -0.1963    1.4096 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0749    2.1297    0.6788 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7884    3.0323    0.3028 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8328    1.5331    0.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7858    1.2978   -2.1183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1571    0.2261   -2.7063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6309    1.6353   -1.4390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0936    3.1963    0.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7801    1.3971    0.9909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6003    1.1122    0.8273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0674   -1.0375    0.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2216   -1.0392   -2.5748 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
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  9  4  1  0
 17 12  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  1
  3 24  1  0
  3 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  6
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  1
 20 38  1  0
M  END

HEADER    PROTEIN                                 19-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUL-19         0                                  
HETATM    1  C   UNK     0    8670.5888665.953   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8671.9178665.183   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8670.5888667.490   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8666.3118662.504   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0    8668.0068666.107   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0    8666.7608665.202   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8667.2368663.737   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8668.7768663.737   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8669.2528665.202   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8668.0068667.647   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8666.6728668.417   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0    8669.3408668.417   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0    8665.3398667.647   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0    8666.6728669.957   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0    8664.0058668.417   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8664.0058669.957   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8662.6718670.727   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8661.3388669.957   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8661.3388668.417   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8662.6718667.647   0.000  0.00  0.00           C+0
CONECT    1    2    3    9                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    7                                                            
CONECT    5    6    9   10                                                  
CONECT    6    7    5                                                       
CONECT    7    6    8    4                                                  
CONECT    8    7    9                                                       
CONECT    9    8    5    1                                                  
CONECT   10    5   11   12                                                  
CONECT   11   10   13   14                                                  
CONECT   12   10                                                            
CONECT   13   11   15                                                       
CONECT   14   11                                                            
CONECT   15   13   16   20                                                  
CONECT   16   17   15                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0011176
HETATM    1  N1  UNL     1       1.675  -2.580  -0.220  1.00  0.00           N  
HETATM    2  C1  UNL     1       0.504  -1.799   0.192  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.860  -1.051   1.481  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.012  -0.148   1.252  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.284  -0.631   1.455  1.00  0.00           C  
HETATM    6  C5  UNL     1       4.380   0.208   1.243  1.00  0.00           C  
HETATM    7  C6  UNL     1       4.186   1.512   0.832  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.917   2.007   0.625  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.836   1.153   0.842  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.090  -0.862  -0.872  1.00  0.00           C  
HETATM   11  O1  UNL     1       0.933  -0.604  -1.783  1.00  0.00           O  
HETATM   12  N2  UNL     1      -1.197  -0.292  -0.851  1.00  0.00           N  
HETATM   13  C10 UNL     1      -1.697   0.691  -1.841  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.611   1.591  -1.033  1.00  0.00           C  
HETATM   15  O2  UNL     1      -2.053   2.874  -0.889  1.00  0.00           O  
HETATM   16  C12 UNL     1      -2.607   0.999   0.387  1.00  0.00           C  
HETATM   17  C13 UNL     1      -2.339  -0.459   0.005  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.500  -1.073  -0.656  1.00  0.00           C  
HETATM   19  O3  UNL     1      -4.542  -1.225   0.033  1.00  0.00           O  
HETATM   20  O4  UNL     1      -3.529  -1.488  -1.959  1.00  0.00           O  
HETATM   21  H1  UNL     1       2.107  -2.113  -1.061  1.00  0.00           H  
HETATM   22  H2  UNL     1       1.365  -3.542  -0.435  1.00  0.00           H  
HETATM   23  H3  UNL     1      -0.323  -2.474   0.417  1.00  0.00           H  
HETATM   24  H4  UNL     1       1.085  -1.825   2.231  1.00  0.00           H  
HETATM   25  H5  UNL     1      -0.014  -0.502   1.804  1.00  0.00           H  
HETATM   26  H6  UNL     1       3.448  -1.656   1.778  1.00  0.00           H  
HETATM   27  H7  UNL     1       5.372  -0.196   1.410  1.00  0.00           H  
HETATM   28  H8  UNL     1       5.075   2.130   0.679  1.00  0.00           H  
HETATM   29  H9  UNL     1       2.788   3.032   0.303  1.00  0.00           H  
HETATM   30  H10 UNL     1       0.833   1.533   0.682  1.00  0.00           H  
HETATM   31  H11 UNL     1      -0.786   1.298  -2.118  1.00  0.00           H  
HETATM   32  H12 UNL     1      -2.157   0.226  -2.706  1.00  0.00           H  
HETATM   33  H13 UNL     1      -3.631   1.635  -1.439  1.00  0.00           H  
HETATM   34  H14 UNL     1      -2.094   3.196   0.037  1.00  0.00           H  
HETATM   35  H15 UNL     1      -1.780   1.397   0.991  1.00  0.00           H  
HETATM   36  H16 UNL     1      -3.600   1.112   0.827  1.00  0.00           H  
HETATM   37  H17 UNL     1      -2.067  -1.037   0.878  1.00  0.00           H  
HETATM   38  H18 UNL     1      -4.222  -1.039  -2.575  1.00  0.00           H  
CONECT    1    2   21   22
CONECT    2    3   10   23
CONECT    3    4   24   25
CONECT    4    5    5    9
CONECT    5    6   26
CONECT    6    7    7   27
CONECT    7    8   28
CONECT    8    9    9   29
CONECT    9   30
CONECT   10   11   11   12
CONECT   12   13   17
CONECT   13   14   31   32
CONECT   14   15   16   33
CONECT   15   34
CONECT   16   17   35   36
CONECT   17   18   37
CONECT   18   19   19   20
CONECT   20   38
END

HMDB0011176
     RDKit          3D
Phenylalanylhydroxyproline
 38 39  0  0  0  0  0  0  0  0999 V2000
    1.6754   -2.5796   -0.2200 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5043   -1.7991    0.1920 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8596   -1.0512    1.4814 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0123   -0.1478    1.2516 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2839   -0.6313    1.4550 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3798    0.2075    1.2427 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1856    1.5124    0.8315 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9172    2.0066    0.6249 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8359    1.1532    0.8424 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0901   -0.8618   -0.8716 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9328   -0.6040   -1.7829 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1967   -0.2916   -0.8513 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6975    0.6911   -1.8415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6114    1.5911   -1.0329 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0528    2.8743   -0.8893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6074    0.9989    0.3873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3394   -0.4588    0.0050 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5003   -1.0725   -0.6564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5424   -1.2247    0.0331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5287   -1.4877   -1.9591 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1068   -2.1127   -1.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3651   -3.5425   -0.4351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3231   -2.4740    0.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0853   -1.8248    2.2313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0135   -0.5019    1.8044 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4480   -1.6564    1.7785 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3720   -0.1963    1.4096 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0749    2.1297    0.6788 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7884    3.0323    0.3028 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8328    1.5331    0.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7858    1.2978   -2.1183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1571    0.2261   -2.7063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6309    1.6353   -1.4390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0936    3.1963    0.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7801    1.3971    0.9909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6003    1.1122    0.8273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0674   -1.0375    0.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2216   -1.0392   -2.5748 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
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  9  4  1  0
 17 12  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  1
  3 24  1  0
  3 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  6
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  1
 20 38  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(4R)-L-Phenylalanyl-4-hydroxy-L-proline	HMDB
L-Phenylalanyl-L-hydroxyproline	HMDB
Phenylalanyl-hydroxyproline	HMDB
Phenylalanine hydroxyproline dipeptide	HMDB
Phenylalanine-hydroxyproline dipeptide	HMDB
(2S,4R)-1-[(2S)-2-Amino-3-phenylpropanoyl]-4-hydroxypyrrolidine-2-carboxylate	HMDB
Phenylalanylhydroxyproline	HMDB

Chemical Formula

C₁₄H₁₈N₂O₄

Average Molecular Weight

278.308

Monoisotopic Molecular Weight

278.126657068

IUPAC Name

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

Traditional Name

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

CAS Registry Number

90965-82-5

SMILES

N[C@@H](CC1=CC=CC=C1)C(=O)N1C[C@H](O)C[C@H]1C(O)=O

InChI Identifier

InChI=1S/C14H18N2O4/c15-11(6-9-4-2-1-3-5-9)13(18)16-8-10(17)7-12(16)14(19)20/h1-5,10-12,17H,6-8,15H2,(H,19,20)/t10-,11+,12+/m1/s1

InChI Key

WJSNJMXOBDSZDL-WOPDTQHZSA-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 or derivatives
N-acyl-l-alpha-amino acid
N-acyl-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
Tertiary carboxylic acid amide
Pyrrolidine
Secondary alcohol
Carboxamide group
Amino acid or derivatives
Amino acid
Azacycle
Organoheterocyclic compound
Carboxylic acid
Monocarboxylic acid or derivatives
Primary aliphatic amine
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Alcohol
Hydrocarbon derivative
Organic oxide
Amine
Primary amine
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Endogenous (HMDB: HMDB0011176)

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	2.72 g/L	ALOGPS
logP	-1.7	ALOGPS
logP	-2.6	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	3.59	ChemAxon
pKa (Strongest Basic)	8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	103.86 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	71.42 m³·mol⁻¹	ChemAxon
Polarizability	27.87 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]+	166.896	30932474
DeepCCS	[M-H]-	164.538	30932474
DeepCCS	[M-2H]-	198.477	30932474
DeepCCS	[M+Na]+	173.712	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.1 minutes	32390414
Predicted by Siyang on May 30, 2022	9.7245 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	7.13 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	348.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	656.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	223.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	93.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	169.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	73.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	267.6 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	299.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	800.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	644.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	147.4 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	813.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	178.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	222.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	438.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	466.0 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	201.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phenylalanylhydroxyproline	N[C@@H](CC1=CC=CC=C1)C(=O)N1C[C@H](O)C[C@H]1C(O)=O	3754.5	Standard polar	33892256
Phenylalanylhydroxyproline	N[C@@H](CC1=CC=CC=C1)C(=O)N1C[C@H](O)C[C@H]1C(O)=O	2540.1	Standard non polar	33892256
Phenylalanylhydroxyproline	N[C@@H](CC1=CC=CC=C1)C(=O)N1C[C@H](O)C[C@H]1C(O)=O	2580.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Phenylalanylhydroxyproline,1TMS,isomer #1	C[Si](C)(C)O[C@@H]1C[C@@H](C(=O)O)N(C(=O)[C@@H](N)CC2=CC=CC=C2)C1	2477.1	Semi standard non polar	33892256
Phenylalanylhydroxyproline,1TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O)CN1C(=O)[C@@H](N)CC1=CC=CC=C1	2411.0	Semi standard non polar	33892256
Phenylalanylhydroxyproline,1TMS,isomer #3	C[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N1C[C@H](O)C[C@H]1C(=O)O	2478.0	Semi standard non polar	33892256
Phenylalanylhydroxyproline,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O[Si](C)(C)C)CN1C(=O)[C@@H](N)CC1=CC=CC=C1	2432.4	Semi standard non polar	33892256
Phenylalanylhydroxyproline,2TMS,isomer #2	C[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N1C[C@H](O[Si](C)(C)C)C[C@H]1C(=O)O	2469.0	Semi standard non polar	33892256
Phenylalanylhydroxyproline,2TMS,isomer #3	C[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N1C[C@H](O)C[C@H]1C(=O)O[Si](C)(C)C	2428.0	Semi standard non polar	33892256
Phenylalanylhydroxyproline,2TMS,isomer #4	C[Si](C)(C)N([C@@H](CC1=CC=CC=C1)C(=O)N1C[C@H](O)C[C@H]1C(=O)O)[Si](C)(C)C	2575.3	Semi standard non polar	33892256
Phenylalanylhydroxyproline,3TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N1C[C@H](O[Si](C)(C)C)C[C@H]1C(=O)O[Si](C)(C)C	2454.2	Semi standard non polar	33892256
Phenylalanylhydroxyproline,3TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N1C[C@H](O[Si](C)(C)C)C[C@H]1C(=O)O[Si](C)(C)C	2490.7	Standard non polar	33892256
Phenylalanylhydroxyproline,3TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N1C[C@H](O[Si](C)(C)C)C[C@H]1C(=O)O[Si](C)(C)C	3045.3	Standard polar	33892256
Phenylalanylhydroxyproline,3TMS,isomer #2	C[Si](C)(C)O[C@@H]1C[C@@H](C(=O)O)N(C(=O)[C@H](CC2=CC=CC=C2)N([Si](C)(C)C)[Si](C)(C)C)C1	2598.5	Semi standard non polar	33892256
Phenylalanylhydroxyproline,3TMS,isomer #2	C[Si](C)(C)O[C@@H]1C[C@@H](C(=O)O)N(C(=O)[C@H](CC2=CC=CC=C2)N([Si](C)(C)C)[Si](C)(C)C)C1	2587.4	Standard non polar	33892256
Phenylalanylhydroxyproline,3TMS,isomer #2	C[Si](C)(C)O[C@@H]1C[C@@H](C(=O)O)N(C(=O)[C@H](CC2=CC=CC=C2)N([Si](C)(C)C)[Si](C)(C)C)C1	3200.6	Standard polar	33892256
Phenylalanylhydroxyproline,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O)CN1C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C	2574.1	Semi standard non polar	33892256
Phenylalanylhydroxyproline,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O)CN1C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C	2524.6	Standard non polar	33892256
Phenylalanylhydroxyproline,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O)CN1C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C	3086.5	Standard polar	33892256
Phenylalanylhydroxyproline,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O[Si](C)(C)C)CN1C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C	2624.7	Semi standard non polar	33892256
Phenylalanylhydroxyproline,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O[Si](C)(C)C)CN1C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C	2588.8	Standard non polar	33892256
Phenylalanylhydroxyproline,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O[Si](C)(C)C)CN1C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C	2915.8	Standard polar	33892256
Phenylalanylhydroxyproline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1C[C@@H](C(=O)O)N(C(=O)[C@@H](N)CC2=CC=CC=C2)C1	2714.7	Semi standard non polar	33892256
Phenylalanylhydroxyproline,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O)CN1C(=O)[C@@H](N)CC1=CC=CC=C1	2656.7	Semi standard non polar	33892256
Phenylalanylhydroxyproline,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N1C[C@H](O)C[C@H]1C(=O)O	2689.9	Semi standard non polar	33892256
Phenylalanylhydroxyproline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O[Si](C)(C)C(C)(C)C)CN1C(=O)[C@@H](N)CC1=CC=CC=C1	2922.2	Semi standard non polar	33892256
Phenylalanylhydroxyproline,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N1C[C@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C(=O)O	2962.7	Semi standard non polar	33892256
Phenylalanylhydroxyproline,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N1C[C@H](O)C[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	2910.2	Semi standard non polar	33892256
Phenylalanylhydroxyproline,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N([C@@H](CC1=CC=CC=C1)C(=O)N1C[C@H](O)C[C@H]1C(=O)O)[Si](C)(C)C(C)(C)C	3017.9	Semi standard non polar	33892256
Phenylalanylhydroxyproline,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N1C[C@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3141.5	Semi standard non polar	33892256
Phenylalanylhydroxyproline,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N1C[C@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3064.0	Standard non polar	33892256
Phenylalanylhydroxyproline,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N1C[C@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3317.3	Standard polar	33892256
Phenylalanylhydroxyproline,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1C[C@@H](C(=O)O)N(C(=O)[C@H](CC2=CC=CC=C2)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1	3304.7	Semi standard non polar	33892256
Phenylalanylhydroxyproline,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1C[C@@H](C(=O)O)N(C(=O)[C@H](CC2=CC=CC=C2)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1	3143.0	Standard non polar	33892256
Phenylalanylhydroxyproline,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1C[C@@H](C(=O)O)N(C(=O)[C@H](CC2=CC=CC=C2)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1	3390.0	Standard polar	33892256
Phenylalanylhydroxyproline,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O)CN1C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3245.3	Semi standard non polar	33892256
Phenylalanylhydroxyproline,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O)CN1C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3110.1	Standard non polar	33892256
Phenylalanylhydroxyproline,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O)CN1C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3309.4	Standard polar	33892256
Phenylalanylhydroxyproline,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O[Si](C)(C)C(C)(C)C)CN1C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3495.3	Semi standard non polar	33892256
Phenylalanylhydroxyproline,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O[Si](C)(C)C(C)(C)C)CN1C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3300.3	Standard non polar	33892256
Phenylalanylhydroxyproline,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O[Si](C)(C)C(C)(C)C)CN1C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3228.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Phenylalanylhydroxyproline 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 - Phenylalanylhydroxyproline 10V, Negative-QTOF	splash10-056r-0390000000-31ed9c98dbb66d5bdb3d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylalanylhydroxyproline 20V, Negative-QTOF	splash10-03di-1920000000-86a3c042ee9832c70b7d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylalanylhydroxyproline 40V, Negative-QTOF	splash10-002f-9700000000-1d418563be37aef5c2fa	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylalanylhydroxyproline 10V, Positive-QTOF	splash10-00b9-0790000000-f811e9ef2e5988d64fc5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylalanylhydroxyproline 20V, Positive-QTOF	splash10-006x-6900000000-8b8fa599b739a54284da	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylalanylhydroxyproline 40V, Positive-QTOF	splash10-006x-8900000000-6a6de752d6f704a905cb	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

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

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB027948

KNApSAcK ID

Not Available

Chemspider ID

29322585

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25227056

PDB ID

Not Available

ChEBI ID

188966

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 Phenylalanylhydroxyproline (HMDB0011176)

MOL for HMDB0011176 (Phenylalanylhydroxyproline)

3D MOL for HMDB0011176 (Phenylalanylhydroxyproline)

3D SDF for HMDB0011176 (Phenylalanylhydroxyproline)

3D-SDF for HMDB0011176 (Phenylalanylhydroxyproline)

PDB for HMDB0011176 (Phenylalanylhydroxyproline)

3D PDB for HMDB0011176 (Phenylalanylhydroxyproline)

SMILES for HMDB0011176 (Phenylalanylhydroxyproline)

INCHI for HMDB0011176 (Phenylalanylhydroxyproline)

Structure for HMDB0011176 (Phenylalanylhydroxyproline)

3D Structure for HMDB0011176 (Phenylalanylhydroxyproline)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra