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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 14:37:27 UTC

Update Date

2021-09-26 23:09:36 UTC

HMDB ID

HMDB0255086

Secondary Accession Numbers

None

Metabolite Identification

Common Name

N-Benzoyl-D-phenylalanine

Description

2-(benzoylamino)-3-phenylpropanoic acid 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. Based on a literature review a significant number of articles have been published on 2-(benzoylamino)-3-phenylpropanoic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). N-benzoyl-d-phenylalanine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically N-Benzoyl-D-phenylalanine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0255086
     RDKit          3D
N-Benzoyl-D-phenylalanine
 35 36  0  0  0  0  0  0  0  0999 V2000
    0.8839   -0.9010    1.6235 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1614   -0.6090    0.4218 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3367   -1.0896   -0.6281 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7978   -1.8995   -0.2990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0958   -1.3494   -0.8240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4252   -0.0157   -0.3196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0293    1.1389   -0.9564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3775    2.3555   -0.4213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1259    2.4474    0.7571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5176    1.2806    1.3874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1762    0.0467    0.8631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5956   -3.2290   -0.9544 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4126   -3.5041   -1.6495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5561   -4.2178   -0.7983 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3257    0.2122    0.2034 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0980    0.6557    1.2675 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2118    1.4394    1.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5971    1.8113   -0.1886 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8385    1.3768   -1.2477 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7147    0.5855   -1.0521 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5390   -0.8675   -1.6149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8677   -2.0394    0.7953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8921   -2.0774   -0.5608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0257   -1.3623   -1.9380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4549    1.0916   -1.8610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0667    3.2434   -0.9208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3608    3.4324    1.1163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0958    1.3527    2.2978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4968   -0.8484    1.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4835   -4.9355   -0.0905 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7966    0.3634    2.2753 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7627    1.7467    1.9476 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4925    2.4419   -0.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1219    1.6554   -2.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1477    0.2682   -1.9332 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  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  4 12  1  0
 12 13  2  0
 12 14  1  0
  2 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 11  6  1  0
 20 15  1  0
  3 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
 20 35  1  0
M  END


  Mrv1533004231518492D          

 20 21  0  0  0  0            999 V2000
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
  4 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  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 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0255086

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)C(CC1=CC=CC=C1)NC(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H15NO3/c18-15(13-9-5-2-6-10-13)17-14(16(19)20)11-12-7-3-1-4-8-12/h1-10,14H,11H2,(H,17,18)(H,19,20)

> <INCHI_KEY>
NPKISZUVEBESJI-UHFFFAOYSA-N

> <FORMULA>
C16H15NO3

> <MOLECULAR_WEIGHT>
269.3

> <EXACT_MASS>
269.105193347

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
27.985775167865377

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-phenyl-2-(phenylformamido)propanoic acid

> <ALOGPS_LOGP>
2.24

> <JCHEM_LOGP>
2.7506360943333332

> <ALOGPS_LOGS>
-3.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.169688209350973

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.829533351947858

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3434900480284337

> <JCHEM_POLAR_SURFACE_AREA>
66.4

> <JCHEM_REFRACTIVITY>
75.23060000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.86e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-phenyl-2-(phenylformamido)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0255086
     RDKit          3D
N-Benzoyl-D-phenylalanine
 35 36  0  0  0  0  0  0  0  0999 V2000
    0.8839   -0.9010    1.6235 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1614   -0.6090    0.4218 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3367   -1.0896   -0.6281 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7978   -1.8995   -0.2990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0958   -1.3494   -0.8240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4252   -0.0157   -0.3196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0293    1.1389   -0.9564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3775    2.3555   -0.4213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1259    2.4474    0.7571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5176    1.2806    1.3874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1762    0.0467    0.8631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5956   -3.2290   -0.9544 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4126   -3.5041   -1.6495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5561   -4.2178   -0.7983 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3257    0.2122    0.2034 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0980    0.6557    1.2675 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2118    1.4394    1.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5971    1.8113   -0.1886 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8385    1.3768   -1.2477 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7147    0.5855   -1.0521 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5390   -0.8675   -1.6149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8677   -2.0394    0.7953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8921   -2.0774   -0.5608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0257   -1.3623   -1.9380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4549    1.0916   -1.8610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0667    3.2434   -0.9208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3608    3.4324    1.1163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0958    1.3527    2.2978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4968   -0.8484    1.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4835   -4.9355   -0.0905 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7966    0.3634    2.2753 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7627    1.7467    1.9476 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4925    2.4419   -0.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1219    1.6554   -2.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1477    0.2682   -1.9332 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  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  4 12  1  0
 12 13  2  0
 12 14  1  0
  2 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 11  6  1  0
 20 15  1  0
  3 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
 20 35  1  0
M  END

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       4.001  -5.390   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    6                                                       
CONECT   12    4   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   20                                                  
CONECT   16   15   17                                                       
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    HMDB0255086
HETATM    1  O1  UNL     1       0.884  -0.901   1.623  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.161  -0.609   0.422  1.00  0.00           C  
HETATM    3  N1  UNL     1       0.337  -1.090  -0.628  1.00  0.00           N  
HETATM    4  C2  UNL     1      -0.798  -1.899  -0.299  1.00  0.00           C  
HETATM    5  C3  UNL     1      -2.096  -1.349  -0.824  1.00  0.00           C  
HETATM    6  C4  UNL     1      -2.425  -0.016  -0.320  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.029   1.139  -0.956  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.377   2.356  -0.421  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.126   2.447   0.757  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.518   1.281   1.387  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.176   0.047   0.863  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.596  -3.229  -0.954  1.00  0.00           C  
HETATM   13  O2  UNL     1       0.413  -3.504  -1.650  1.00  0.00           O  
HETATM   14  O3  UNL     1      -1.556  -4.218  -0.798  1.00  0.00           O  
HETATM   15  C11 UNL     1       2.326   0.212   0.203  1.00  0.00           C  
HETATM   16  C12 UNL     1       3.098   0.656   1.268  1.00  0.00           C  
HETATM   17  C13 UNL     1       4.212   1.439   1.080  1.00  0.00           C  
HETATM   18  C14 UNL     1       4.597   1.811  -0.189  1.00  0.00           C  
HETATM   19  C15 UNL     1       3.839   1.377  -1.248  1.00  0.00           C  
HETATM   20  C16 UNL     1       2.715   0.585  -1.052  1.00  0.00           C  
HETATM   21  H1  UNL     1       0.539  -0.867  -1.615  1.00  0.00           H  
HETATM   22  H2  UNL     1      -0.868  -2.039   0.795  1.00  0.00           H  
HETATM   23  H3  UNL     1      -2.892  -2.077  -0.561  1.00  0.00           H  
HETATM   24  H4  UNL     1      -2.026  -1.362  -1.938  1.00  0.00           H  
HETATM   25  H5  UNL     1      -1.455   1.092  -1.861  1.00  0.00           H  
HETATM   26  H6  UNL     1      -2.067   3.243  -0.921  1.00  0.00           H  
HETATM   27  H7  UNL     1      -3.361   3.432   1.116  1.00  0.00           H  
HETATM   28  H8  UNL     1      -4.096   1.353   2.298  1.00  0.00           H  
HETATM   29  H9  UNL     1      -3.497  -0.848   1.378  1.00  0.00           H  
HETATM   30  H10 UNL     1      -1.484  -4.936  -0.091  1.00  0.00           H  
HETATM   31  H11 UNL     1       2.797   0.363   2.275  1.00  0.00           H  
HETATM   32  H12 UNL     1       4.763   1.747   1.948  1.00  0.00           H  
HETATM   33  H13 UNL     1       5.493   2.442  -0.346  1.00  0.00           H  
HETATM   34  H14 UNL     1       4.122   1.655  -2.241  1.00  0.00           H  
HETATM   35  H15 UNL     1       2.148   0.268  -1.933  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   15
CONECT    3    4   21
CONECT    4    5   12   22
CONECT    5    6   23   24
CONECT    6    7    7   11
CONECT    7    8   25
CONECT    8    9    9   26
CONECT    9   10   27
CONECT   10   11   11   28
CONECT   11   29
CONECT   12   13   13   14
CONECT   14   30
CONECT   15   16   16   20
CONECT   16   17   31
CONECT   17   18   18   32
CONECT   18   19   33
CONECT   19   20   20   34
CONECT   20   35
END

HMDB0255086
     RDKit          3D
N-Benzoyl-D-phenylalanine
 35 36  0  0  0  0  0  0  0  0999 V2000
    0.8839   -0.9010    1.6235 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1614   -0.6090    0.4218 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3367   -1.0896   -0.6281 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7978   -1.8995   -0.2990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0958   -1.3494   -0.8240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4252   -0.0157   -0.3196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0293    1.1389   -0.9564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3775    2.3555   -0.4213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1259    2.4474    0.7571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5176    1.2806    1.3874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1762    0.0467    0.8631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5956   -3.2290   -0.9544 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4126   -3.5041   -1.6495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5561   -4.2178   -0.7983 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3257    0.2122    0.2034 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0980    0.6557    1.2675 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2118    1.4394    1.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5971    1.8113   -0.1886 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8385    1.3768   -1.2477 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7147    0.5855   -1.0521 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5390   -0.8675   -1.6149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8677   -2.0394    0.7953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8921   -2.0774   -0.5608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0257   -1.3623   -1.9380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4549    1.0916   -1.8610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0667    3.2434   -0.9208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3608    3.4324    1.1163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0958    1.3527    2.2978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4968   -0.8484    1.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4835   -4.9355   -0.0905 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7966    0.3634    2.2753 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7627    1.7467    1.9476 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4925    2.4419   -0.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1219    1.6554   -2.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1477    0.2682   -1.9332 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  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  4 12  1  0
 12 13  2  0
 12 14  1  0
  2 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 11  6  1  0
 20 15  1  0
  3 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
 20 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(Benzoylamino)-3-phenylpropionic acid	ChEBI
2-(Benzoylamino)-3-phenylpropionate	Generator
2-(Benzoylamino)-3-phenylpropanoate	Generator

Chemical Formula

C₁₆H₁₅NO₃

Average Molecular Weight

269.3

Monoisotopic Molecular Weight

269.105193347

IUPAC Name

3-phenyl-2-(phenylformamido)propanoic acid

Traditional Name

3-phenyl-2-(phenylformamido)propanoic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C(CC1=CC=CC=C1)NC(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C16H15NO3/c18-15(13-9-5-2-6-10-13)17-14(16(19)20)11-12-7-3-1-4-8-12/h1-10,14H,11H2,(H,17,18)(H,19,20)

InChI Key

NPKISZUVEBESJI-UHFFFAOYSA-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
Hippuric acid or derivatives
Hippuric acid
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
3-phenylpropanoic-acid
Amphetamine or derivatives
Benzamide
Benzoic acid or derivatives
Benzoyl
Monocyclic benzene moiety
Benzenoid
Secondary carboxylic acid amide
Carboxamide group
Monocarboxylic acid or derivatives
Carboxylic acid
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

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
logP	2.24	ALOGPS
logP	2.75	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	3.83	ChemAxon
pKa (Strongest Basic)	-1.3	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	5	ChemAxon
Refractivity	75.23 m³·mol⁻¹	ChemAxon
Polarizability	27.99 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
DeepCCS	[M+H]+	162.602	30932474
DeepCCS	[M-H]-	160.244	30932474
DeepCCS	[M-2H]-	193.13	30932474
DeepCCS	[M+Na]+	168.695	30932474
AllCCS	[M+H]+	163.2	32859911
AllCCS	[M+H-H2O]+	159.5	32859911
AllCCS	[M+NH4]+	166.6	32859911
AllCCS	[M+Na]+	167.6	32859911
AllCCS	[M-H]-	165.0	32859911
AllCCS	[M+Na-2H]-	164.7	32859911
AllCCS	[M+HCOO]-	164.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Benzoyl-D-phenylalanine	OC(=O)C(CC1=CC=CC=C1)NC(=O)C1=CC=CC=C1	3332.3	Standard polar	33892256
N-Benzoyl-D-phenylalanine	OC(=O)C(CC1=CC=CC=C1)NC(=O)C1=CC=CC=C1	2213.3	Standard non polar	33892256
N-Benzoyl-D-phenylalanine	OC(=O)C(CC1=CC=CC=C1)NC(=O)C1=CC=CC=C1	2365.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Benzoyl-D-phenylalanine,2TMS,isomer #1	C[Si](C)(C)OC(=O)C(CC1=CC=CC=C1)N(C(=O)C1=CC=CC=C1)[Si](C)(C)C	2299.7	Semi standard non polar	33892256
N-Benzoyl-D-phenylalanine,2TMS,isomer #1	C[Si](C)(C)OC(=O)C(CC1=CC=CC=C1)N(C(=O)C1=CC=CC=C1)[Si](C)(C)C	2313.8	Standard non polar	33892256
N-Benzoyl-D-phenylalanine,2TMS,isomer #1	C[Si](C)(C)OC(=O)C(CC1=CC=CC=C1)N(C(=O)C1=CC=CC=C1)[Si](C)(C)C	2872.5	Standard polar	33892256
N-Benzoyl-D-phenylalanine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=CC=C1)N(C(=O)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2789.7	Semi standard non polar	33892256
N-Benzoyl-D-phenylalanine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=CC=C1)N(C(=O)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2724.7	Standard non polar	33892256
N-Benzoyl-D-phenylalanine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=CC=C1)N(C(=O)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	3055.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Benzoyl-D-phenylalanine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-3910000000-c9390881176dd1cf0c6a	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Benzoyl-D-phenylalanine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Benzoyl-D-phenylalanine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Benzoyl-D-phenylalanine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Benzoyl-D-phenylalanine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Benzoyl-D-phenylalanine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

240518

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

273362

PDB ID

Not Available

ChEBI ID

90419

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for N-Benzoyl-D-phenylalanine (HMDB0255086)

MOL for HMDB0255086 (N-Benzoyl-D-phenylalanine)

3D MOL for HMDB0255086 (N-Benzoyl-D-phenylalanine)

3D SDF for HMDB0255086 (N-Benzoyl-D-phenylalanine)

3D-SDF for HMDB0255086 (N-Benzoyl-D-phenylalanine)

PDB for HMDB0255086 (N-Benzoyl-D-phenylalanine)

3D PDB for HMDB0255086 (N-Benzoyl-D-phenylalanine)

SMILES for HMDB0255086 (N-Benzoyl-D-phenylalanine)

INCHI for HMDB0255086 (N-Benzoyl-D-phenylalanine)

Structure for HMDB0255086 (N-Benzoyl-D-phenylalanine)

3D Structure for HMDB0255086 (N-Benzoyl-D-phenylalanine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra