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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:50 UTC

Update Date

2022-09-22 18:34:16 UTC

HMDB ID

HMDB0002372

Secondary Accession Numbers

HMDB02372

Metabolite Identification

Common Name

N-Phenylacetylphenylalanine

Description

N-Phenylacetylphenylalanine belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. N-Phenylacetylphenylalanine 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 N-phenylacetylphenylalanine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on N-Phenylacetylphenylalanine.

Structure

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

HMDB0002372
     RDKit          3D
N-Phenylacetylphenylalanine
 38 39  0  0  0  0  0  0  0  0999 V2000
   -0.9084    1.8566   -0.0763 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1869    1.6262    0.4850 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4442    1.9086   -0.2105 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8405    0.9034   -1.2165 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7666   -0.0571   -0.8021 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2030   -1.0437   -1.6562 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7144   -1.0828   -2.9464 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8026   -0.1500   -3.3796 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3764    0.8319   -2.5088 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1569    1.0876    1.7977 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0247    0.7907    2.5680 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4205   -0.6643    2.3222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7094   -0.8752    0.8752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9273   -0.6356    0.2849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1343   -0.8367   -1.0591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0924   -1.2937   -1.8583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8428   -1.5453   -1.2822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6846   -1.3283    0.0780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7279    0.9405    3.9929 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4556    1.2317    4.3370 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6692    0.7830    4.9770 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2541    2.0326    0.5347 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3710    2.8813   -0.8072 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1619   -0.0319    0.2236 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9356   -1.8083   -1.3416 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0533   -1.8550   -3.6231 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4121   -0.1774   -4.3980 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6576    1.6010   -2.7880 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1054    0.8949    2.2406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8449    1.4475    2.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2637   -0.9701    2.9325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5478   -1.2820    2.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7330   -0.2744    0.9290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0855   -0.6452   -1.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1798   -1.4704   -2.9182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0138   -1.9055   -1.8851 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3005   -1.5280    0.5106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3889    0.6437    5.9416 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 11 19  1  0
 19 20  2  0
 19 21  1  0
  9  4  1  0
 18 13  1  0
  3 22  1  0
  3 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  6
 12 31  1  0
 12 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 21 38  1  0
M  END

  Mrv0541 02231219302D          

 21 22  0  0  1  0            999 V2000
   44.7404  -28.4533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   44.7404  -27.6283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   44.0259  -29.6908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   43.3115  -27.6283    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   43.3115  -28.4533    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   42.5969  -28.8658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.5969  -29.6908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.0259  -26.3908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.0259  -27.2158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.0259  -28.8658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.7404  -25.9783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.3115  -30.1033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.8825  -30.1033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.3115  -30.9283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.8825  -30.9283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.4548  -26.3908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.7404  -25.1533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.5969  -31.3408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.1694  -25.9783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.4548  -24.7408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.1694  -25.1533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0  0  0  0
  2  9  2  0  0  0  0
  3 10  2  0  0  0  0
  5  4  1  6  0  0  0
  4  9  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  6  7  1  0  0  0  0
  7 12  2  0  0  0  0
  7 13  1  0  0  0  0
  8  9  1  0  0  0  0
  8 11  1  0  0  0  0
 11 16  2  0  0  0  0
 11 17  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  2  0  0  0  0
 14 18  2  0  0  0  0
 15 18  1  0  0  0  0
 16 19  1  0  0  0  0
 17 20  2  0  0  0  0
 19 21  2  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002372

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H17NO3/c19-16(12-14-9-5-2-6-10-14)18-15(17(20)21)11-13-7-3-1-4-8-13/h1-10,15H,11-12H2,(H,18,19)(H,20,21)/t15-/m0/s1

> <INCHI_KEY>
LIIPHJDKZNTNII-HNNXBMFYSA-N

> <FORMULA>
C17H17NO3

> <MOLECULAR_WEIGHT>
283.3218

> <EXACT_MASS>
283.120843415

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
29.96839497319879

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-3-phenyl-2-(2-phenylacetamido)propanoic acid

> <ALOGPS_LOGP>
2.39

> <JCHEM_LOGP>
2.7308014756666665

> <ALOGPS_LOGS>
-4.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.006142699763444

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.0786202487690595

> <JCHEM_PKA_STRONGEST_BASIC>
-2.5988768477799487

> <JCHEM_POLAR_SURFACE_AREA>
66.39999999999999

> <JCHEM_REFRACTIVITY>
79.28200000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.68e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-phenylacetyl-L-phenylalanine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002372
     RDKit          3D
N-Phenylacetylphenylalanine
 38 39  0  0  0  0  0  0  0  0999 V2000
   -0.9084    1.8566   -0.0763 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1869    1.6262    0.4850 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4442    1.9086   -0.2105 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8405    0.9034   -1.2165 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7666   -0.0571   -0.8021 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2030   -1.0437   -1.6562 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7144   -1.0828   -2.9464 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8026   -0.1500   -3.3796 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3764    0.8319   -2.5088 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1569    1.0876    1.7977 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0247    0.7907    2.5680 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4205   -0.6643    2.3222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7094   -0.8752    0.8752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9273   -0.6356    0.2849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1343   -0.8367   -1.0591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0924   -1.2937   -1.8583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8428   -1.5453   -1.2822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6846   -1.3283    0.0780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7279    0.9405    3.9929 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4556    1.2317    4.3370 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6692    0.7830    4.9770 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2541    2.0326    0.5347 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3710    2.8813   -0.8072 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1619   -0.0319    0.2236 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9356   -1.8083   -1.3416 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0533   -1.8550   -3.6231 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4121   -0.1774   -4.3980 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6576    1.6010   -2.7880 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1054    0.8949    2.2406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8449    1.4475    2.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2637   -0.9701    2.9325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5478   -1.2820    2.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7330   -0.2744    0.9290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0855   -0.6452   -1.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1798   -1.4704   -2.9182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0138   -1.9055   -1.8851 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3005   -1.5280    0.5106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3889    0.6437    5.9416 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 11 19  1  0
 19 20  2  0
 19 21  1  0
  9  4  1  0
 18 13  1  0
  3 22  1  0
  3 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  6
 12 31  1  0
 12 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 21 38  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      83.515 -53.113   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      83.515 -51.573   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      82.182 -55.423   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      80.848 -51.573   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      80.848 -53.113   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      79.514 -53.883   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      79.514 -55.423   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      82.182 -49.263   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      82.182 -50.803   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      82.182 -53.883   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      83.515 -48.493   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      80.848 -56.193   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      78.181 -56.193   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      80.848 -57.733   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      78.181 -57.733   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      84.849 -49.263   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      83.515 -46.953   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      79.514 -58.503   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      86.183 -48.493   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      84.849 -46.183   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      86.183 -46.953   0.000  0.00  0.00           C+0
CONECT    1   10                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4    5    9                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6   12   13                                                  
CONECT    8    9   11                                                       
CONECT    9    2    4    8                                                  
CONECT   10    1    3    5                                                  
CONECT   11    8   16   17                                                  
CONECT   12    7   14                                                       
CONECT   13    7   15                                                       
CONECT   14   12   18                                                       
CONECT   15   13   18                                                       
CONECT   16   11   19                                                       
CONECT   17   11   20                                                       
CONECT   18   14   15                                                       
CONECT   19   16   21                                                       
CONECT   20   17   21                                                       
CONECT   21   19   20                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0002372
HETATM    1  O1  UNL     1      -0.908   1.857  -0.076  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.187   1.626   0.485  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.444   1.909  -0.211  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.840   0.903  -1.216  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.767  -0.057  -0.802  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.203  -1.044  -1.656  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.714  -1.083  -2.946  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.803  -0.150  -3.380  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.376   0.832  -2.509  1.00  0.00           C  
HETATM   10  N1  UNL     1       0.157   1.088   1.798  1.00  0.00           N  
HETATM   11  C9  UNL     1      -1.025   0.791   2.568  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.420  -0.664   2.322  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.709  -0.875   0.875  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.927  -0.636   0.285  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.134  -0.837  -1.059  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.092  -1.294  -1.858  1.00  0.00           C  
HETATM   17  C15 UNL     1      -0.843  -1.545  -1.282  1.00  0.00           C  
HETATM   18  C16 UNL     1      -0.685  -1.328   0.078  1.00  0.00           C  
HETATM   19  C17 UNL     1      -0.728   0.941   3.993  1.00  0.00           C  
HETATM   20  O2  UNL     1       0.456   1.232   4.337  1.00  0.00           O  
HETATM   21  O3  UNL     1      -1.669   0.783   4.977  1.00  0.00           O  
HETATM   22  H1  UNL     1       2.254   2.033   0.535  1.00  0.00           H  
HETATM   23  H2  UNL     1       1.371   2.881  -0.807  1.00  0.00           H  
HETATM   24  H3  UNL     1       3.162  -0.032   0.224  1.00  0.00           H  
HETATM   25  H4  UNL     1       3.936  -1.808  -1.342  1.00  0.00           H  
HETATM   26  H5  UNL     1       3.053  -1.855  -3.623  1.00  0.00           H  
HETATM   27  H6  UNL     1       1.412  -0.177  -4.398  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.658   1.601  -2.788  1.00  0.00           H  
HETATM   29  H8  UNL     1       1.105   0.895   2.241  1.00  0.00           H  
HETATM   30  H9  UNL     1      -1.845   1.447   2.175  1.00  0.00           H  
HETATM   31  H10 UNL     1      -2.264  -0.970   2.933  1.00  0.00           H  
HETATM   32  H11 UNL     1      -0.548  -1.282   2.591  1.00  0.00           H  
HETATM   33  H12 UNL     1      -3.733  -0.274   0.929  1.00  0.00           H  
HETATM   34  H13 UNL     1      -4.085  -0.645  -1.516  1.00  0.00           H  
HETATM   35  H14 UNL     1      -2.180  -1.470  -2.918  1.00  0.00           H  
HETATM   36  H15 UNL     1      -0.014  -1.906  -1.885  1.00  0.00           H  
HETATM   37  H16 UNL     1       0.301  -1.528   0.511  1.00  0.00           H  
HETATM   38  H17 UNL     1      -1.389   0.644   5.942  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   10
CONECT    3    4   22   23
CONECT    4    5    5    9
CONECT    5    6   24
CONECT    6    7    7   25
CONECT    7    8   26
CONECT    8    9    9   27
CONECT    9   28
CONECT   10   11   29
CONECT   11   12   19   30
CONECT   12   13   31   32
CONECT   13   14   14   18
CONECT   14   15   33
CONECT   15   16   16   34
CONECT   16   17   35
CONECT   17   18   18   36
CONECT   18   37
CONECT   19   20   20   21
CONECT   21   38
END

HMDB0002372
     RDKit          3D
N-Phenylacetylphenylalanine
 38 39  0  0  0  0  0  0  0  0999 V2000
   -0.9084    1.8566   -0.0763 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1869    1.6262    0.4850 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4442    1.9086   -0.2105 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8405    0.9034   -1.2165 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7666   -0.0571   -0.8021 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2030   -1.0437   -1.6562 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7144   -1.0828   -2.9464 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8026   -0.1500   -3.3796 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3764    0.8319   -2.5088 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1569    1.0876    1.7977 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0247    0.7907    2.5680 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4205   -0.6643    2.3222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7094   -0.8752    0.8752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9273   -0.6356    0.2849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1343   -0.8367   -1.0591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0924   -1.2937   -1.8583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8428   -1.5453   -1.2822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6846   -1.3283    0.0780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7279    0.9405    3.9929 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4556    1.2317    4.3370 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6692    0.7830    4.9770 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2541    2.0326    0.5347 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3710    2.8813   -0.8072 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1619   -0.0319    0.2236 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9356   -1.8083   -1.3416 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0533   -1.8550   -3.6231 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4121   -0.1774   -4.3980 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6576    1.6010   -2.7880 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1054    0.8949    2.2406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8449    1.4475    2.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2637   -0.9701    2.9325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5478   -1.2820    2.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7330   -0.2744    0.9290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0855   -0.6452   -1.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1798   -1.4704   -2.9182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0138   -1.9055   -1.8851 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3005   -1.5280    0.5106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3889    0.6437    5.9416 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 11 19  1  0
 19 20  2  0
 19 21  1  0
  9  4  1  0
 18 13  1  0
  3 22  1  0
  3 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  6
 12 31  1  0
 12 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 21 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Phenyl-N-(phenylacetyl)-alanine	HMDB
L-3-Phenyl-N-(phenylacetyl)-alanine	HMDB
N-(Phenylacetyl)-L-phenylalanine	HMDB
N-Phenylacetyl-L-phenylalanine	HMDB, MeSH
N-Phenylacetylphenylalanine, (D)-isomer	MeSH, HMDB
(2S)-2-[(1-Hydroxy-2-phenylethylidene)amino]-3-phenylpropanoate	Generator, HMDB
N-Phenylacetylphenylalanine	MeSH

Chemical Formula

C₁₇H₁₇NO₃

Average Molecular Weight

283.3218

Monoisotopic Molecular Weight

283.120843415

IUPAC Name

(2S)-3-phenyl-2-(2-phenylacetamido)propanoic acid

Traditional Name

N-phenylacetyl-L-phenylalanine

CAS Registry Number

738-75-0

SMILES

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

InChI Identifier

InChI=1S/C17H17NO3/c19-16(12-14-9-5-2-6-10-14)18-15(17(20)21)11-13-7-3-1-4-8-13/h1-10,15H,11-12H2,(H,18,19)(H,20,21)/t15-/m0/s1

InChI Key

LIIPHJDKZNTNII-HNNXBMFYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Phenylalanine and derivatives

Alternative Parents

Substituents

Phenylalanine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
N-acyl-l-alpha-amino acid
3-phenylpropanoic-acid
Amphetamine or derivatives
Phenylacetamide
Monocyclic benzene moiety
Benzenoid
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0002372)
Cell membrane (HMDB: HMDB0002372)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0002372)
Feces (PMID: 27275383)

Source

Endogenous

Endogenous (HMDB: HMDB0002372)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.027 g/L	ALOGPS
logP	2.39	ALOGPS
logP	2.73	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	4.08	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.4 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	79.28 m³·mol⁻¹	ChemAxon
Polarizability	29.97 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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
DarkChem	[M+H]+	165.926	31661259
DarkChem	[M-H]-	165.503	31661259
DeepCCS	[M+H]+	165.729	30932474
DeepCCS	[M-H]-	163.371	30932474
DeepCCS	[M-2H]-	196.995	30932474
DeepCCS	[M+Na]+	172.221	30932474
AllCCS	[M+H]+	167.3	32859911
AllCCS	[M+H-H2O]+	163.7	32859911
AllCCS	[M+NH4]+	170.5	32859911
AllCCS	[M+Na]+	171.5	32859911
AllCCS	[M-H]-	169.5	32859911
AllCCS	[M+Na-2H]-	169.2	32859911
AllCCS	[M+HCOO]-	169.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Phenylacetylphenylalanine	OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)CC1=CC=CC=C1	3626.0	Standard polar	33892256
N-Phenylacetylphenylalanine	OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)CC1=CC=CC=C1	2260.5	Standard non polar	33892256
N-Phenylacetylphenylalanine	OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)CC1=CC=CC=C1	2409.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Phenylacetylphenylalanine,1TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)CC1=CC=CC=C1	2405.2	Semi standard non polar	33892256
N-Phenylacetylphenylalanine,1TMS,isomer #2	C[Si](C)(C)N(C(=O)CC1=CC=CC=C1)[C@@H](CC1=CC=CC=C1)C(=O)O	2410.8	Semi standard non polar	33892256
N-Phenylacetylphenylalanine,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C	2371.9	Semi standard non polar	33892256
N-Phenylacetylphenylalanine,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C	2422.6	Standard non polar	33892256
N-Phenylacetylphenylalanine,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C	3004.3	Standard polar	33892256
N-Phenylacetylphenylalanine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)CC1=CC=CC=C1	2670.5	Semi standard non polar	33892256
N-Phenylacetylphenylalanine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(=O)CC1=CC=CC=C1)[C@@H](CC1=CC=CC=C1)C(=O)O	2651.8	Semi standard non polar	33892256
N-Phenylacetylphenylalanine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2860.2	Semi standard non polar	33892256
N-Phenylacetylphenylalanine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2820.8	Standard non polar	33892256
N-Phenylacetylphenylalanine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	3147.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Phenylacetylphenylalanine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-7920000000-414527b0d8767edb022a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Phenylacetylphenylalanine GC-MS (1 TMS) - 70eV, Positive	splash10-006x-9301000000-6bba534fc811e446dd42	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Phenylacetylphenylalanine 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 - N-Phenylacetylphenylalanine 10V, Positive-QTOF	splash10-02ai-2890000000-731f005addd7e44b2d79	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Phenylacetylphenylalanine 20V, Positive-QTOF	splash10-014i-1920000000-1a43b8b4de97159d1462	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Phenylacetylphenylalanine 40V, Positive-QTOF	splash10-0006-9300000000-3ae402042e506b3eac68	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Phenylacetylphenylalanine 10V, Negative-QTOF	splash10-001i-0490000000-47fac515ba1e5c7e08a2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Phenylacetylphenylalanine 20V, Negative-QTOF	splash10-00m3-1940000000-4ac1507005c25d36f8b4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Phenylacetylphenylalanine 40V, Negative-QTOF	splash10-014l-9700000000-2bb6f7f95d0c2306716f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Phenylacetylphenylalanine 10V, Positive-QTOF	splash10-00lr-0590000000-c540ae154f5783eaed2c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Phenylacetylphenylalanine 20V, Positive-QTOF	splash10-00di-1900000000-f83c0d5eac6e34453864	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Phenylacetylphenylalanine 40V, Positive-QTOF	splash10-0006-9600000000-6e9bb33785266131fff2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Phenylacetylphenylalanine 10V, Negative-QTOF	splash10-03xr-1910000000-f164e21280a47480c5dd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Phenylacetylphenylalanine 20V, Negative-QTOF	splash10-044m-4910000000-948f26d129049ea5276f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Phenylacetylphenylalanine 40V, Negative-QTOF	splash10-00r7-7900000000-454ec737db24b4710cdd	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

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
Urine	Detected and Quantified	6.988 +/- 4.615 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	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
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Urine	Detected and Quantified	5.592 +/- 3.046 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022983

KNApSAcK ID

Not Available

Chemspider ID

43287

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

47579

PDB ID

Not Available

ChEBI ID

975589

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

Burley SK, Wang AH, Votano JR, Rich A: Antigelling and antisickling bisphenyl oligopeptides and peptide analogues have similar structural features. Biochemistry. 1987 Aug 11;26(16):5091-9. [PubMed:3663644 ]
Votano JR, Altman J, Wilchek M, Gorecki M, Rich A: Potential use of biaromatic L-phenylalanyl derivatives as therapeutic agents in the treatment of sickle cell disease. Proc Natl Acad Sci U S A. 1984 May;81(10):3190-4. [PubMed:6587344 ]

Showing metabocard for N-Phenylacetylphenylalanine (HMDB0002372)

MOL for HMDB0002372 (N-Phenylacetylphenylalanine)

3D MOL for HMDB0002372 (N-Phenylacetylphenylalanine)

3D SDF for HMDB0002372 (N-Phenylacetylphenylalanine)

3D-SDF for HMDB0002372 (N-Phenylacetylphenylalanine)

PDB for HMDB0002372 (N-Phenylacetylphenylalanine)

3D PDB for HMDB0002372 (N-Phenylacetylphenylalanine)

SMILES for HMDB0002372 (N-Phenylacetylphenylalanine)

INCHI for HMDB0002372 (N-Phenylacetylphenylalanine)

Structure for HMDB0002372 (N-Phenylacetylphenylalanine)

3D Structure for HMDB0002372 (N-Phenylacetylphenylalanine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra