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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:27:42 UTC

Update Date

2022-03-07 02:56:04 UTC

HMDB ID

HMDB0039102

Secondary Accession Numbers

HMDB39102

Metabolite Identification

Common Name

N-Carboxyacetyl-D-phenylalanine

Description

N-Carboxyacetyl-D-phenylalanine 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-Carboxyacetyl-D-phenylalanine has been detected, but not quantified in, pulses. This could make N-carboxyacetyl-D-phenylalanine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on N-Carboxyacetyl-D-phenylalanine.

Structure

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

HMDB0039102
     RDKit          3D
N-Carboxyacetyl-D-phenylalanine
 31 31  0  0  0  0  0  0  0  0999 V2000
    3.2194    1.4028    1.5033 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1095    2.0690    0.4643 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7533    3.2741    0.2525 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2371    1.5432   -0.6141 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6184    0.2515   -0.2443 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8826   -0.2453    0.8947 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7524   -0.4201   -1.1325 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1345   -1.6812   -0.7992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3697   -1.5248   -0.8775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7370   -0.4669    0.1075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0427   -0.7902    1.4184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3828    0.1674    2.3406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4194    1.4886    1.9439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1144    1.8185    0.6331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7702    0.8423   -0.2973 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5386   -2.7712   -1.7091 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3415   -2.5249   -2.6445 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0064   -4.0337   -1.4867 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3108    3.7528    0.9358 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4073    2.2820   -0.7322 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8189    1.4557   -1.5753 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5471    0.0002   -2.0600 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4717   -1.9619    0.2143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8628   -2.4792   -0.6780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6746   -1.1679   -1.8626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9919   -1.8572    1.6564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6178   -0.1295    3.3677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6893    2.2204    2.6871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1557    2.8733    0.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5328    1.1244   -1.3275 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2115   -4.5122   -0.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  8 16  1  0
 16 17  2  0
 16 18  1  0
 15 10  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 18 31  1  0
M  END


  Mrv0541 02241210072D          

 18 18  0  0  0  0            999 V2000
    0.5739    1.2306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2463    0.9847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7381    1.5590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4616   -0.3280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8049    0.0821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8049    0.9022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4616    1.3131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2001    0.9022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2001    0.0821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0664   -0.3280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3280    0.1638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3280   -0.3280    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0664   -1.5590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0664   -0.7381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7232   -0.3280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4616   -0.7381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4616   -1.5590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2001   -0.3280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2 11  1  0  0  0  0
  4  5  2  0  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  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 14  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0039102

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H13NO5/c14-10(7-11(15)16)13-9(12(17)18)6-8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H,13,14)(H,15,16)(H,17,18)

> <INCHI_KEY>
IHAMOIOWKITHQZ-UHFFFAOYSA-N

> <FORMULA>
C12H13NO5

> <MOLECULAR_WEIGHT>
251.2353

> <EXACT_MASS>
251.079372531

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
24.031796800806763

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(2-carboxyacetamido)-3-phenylpropanoic acid

> <ALOGPS_LOGP>
0.52

> <JCHEM_LOGP>
0.7886901019999998

> <ALOGPS_LOGS>
-2.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.134195958169494

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4299208546570927

> <JCHEM_PKA_STRONGEST_BASIC>
-6.053592235144011

> <JCHEM_POLAR_SURFACE_AREA>
103.7

> <JCHEM_REFRACTIVITY>
60.90420000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.04e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(2-carboxyacetamido)-3-phenylpropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0039102
     RDKit          3D
N-Carboxyacetyl-D-phenylalanine
 31 31  0  0  0  0  0  0  0  0999 V2000
    3.2194    1.4028    1.5033 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1095    2.0690    0.4643 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7533    3.2741    0.2525 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2371    1.5432   -0.6141 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6184    0.2515   -0.2443 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8826   -0.2453    0.8947 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7524   -0.4201   -1.1325 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1345   -1.6812   -0.7992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3697   -1.5248   -0.8775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7370   -0.4669    0.1075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0427   -0.7902    1.4184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3828    0.1674    2.3406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4194    1.4886    1.9439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1144    1.8185    0.6331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7702    0.8423   -0.2973 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5386   -2.7712   -1.7091 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3415   -2.5249   -2.6445 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0064   -4.0337   -1.4867 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3108    3.7528    0.9358 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4073    2.2820   -0.7322 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8189    1.4557   -1.5753 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5471    0.0002   -2.0600 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4717   -1.9619    0.2143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8628   -2.4792   -0.6780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6746   -1.1679   -1.8626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9919   -1.8572    1.6564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6178   -0.1295    3.3677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6893    2.2204    2.6871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1557    2.8733    0.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5328    1.1244   -1.3275 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2115   -4.5122   -0.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  8 16  1  0
 16 17  2  0
 16 18  1  0
 15 10  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 18 31  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       1.071   2.297   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.460   1.838   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.378   2.910   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -4.595  -0.612   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.369   0.153   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.369   1.684   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.595   2.451   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.974   1.684   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.974   0.153   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.991  -0.612   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.612   0.306   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       0.612  -0.612   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0       1.991  -2.910   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.991  -1.378   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.217  -0.612   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.595  -1.378   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.595  -2.910   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.974  -0.612   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2                                                            
CONECT    4    5    9                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    4    8                                                       
CONECT   10    5   11                                                       
CONECT   11    2   10   12                                                  
CONECT   12   11   14                                                       
CONECT   13   14                                                            
CONECT   14   12   13   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0039102
HETATM    1  O1  UNL     1       3.219   1.403   1.503  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.110   2.069   0.464  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.753   3.274   0.253  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.237   1.543  -0.614  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.618   0.251  -0.244  1.00  0.00           C  
HETATM    6  O3  UNL     1       1.883  -0.245   0.895  1.00  0.00           O  
HETATM    7  N1  UNL     1       0.752  -0.420  -1.133  1.00  0.00           N  
HETATM    8  C4  UNL     1       0.134  -1.681  -0.799  1.00  0.00           C  
HETATM    9  C5  UNL     1      -1.370  -1.525  -0.877  1.00  0.00           C  
HETATM   10  C6  UNL     1      -1.737  -0.467   0.107  1.00  0.00           C  
HETATM   11  C7  UNL     1      -2.043  -0.790   1.418  1.00  0.00           C  
HETATM   12  C8  UNL     1      -2.383   0.167   2.341  1.00  0.00           C  
HETATM   13  C9  UNL     1      -2.419   1.489   1.944  1.00  0.00           C  
HETATM   14  C10 UNL     1      -2.114   1.819   0.633  1.00  0.00           C  
HETATM   15  C11 UNL     1      -1.770   0.842  -0.297  1.00  0.00           C  
HETATM   16  C12 UNL     1       0.539  -2.771  -1.709  1.00  0.00           C  
HETATM   17  O4  UNL     1       1.342  -2.525  -2.645  1.00  0.00           O  
HETATM   18  O5  UNL     1       0.006  -4.034  -1.487  1.00  0.00           O  
HETATM   19  H1  UNL     1       4.311   3.753   0.936  1.00  0.00           H  
HETATM   20  H2  UNL     1       1.407   2.282  -0.732  1.00  0.00           H  
HETATM   21  H3  UNL     1       2.819   1.456  -1.575  1.00  0.00           H  
HETATM   22  H4  UNL     1       0.547   0.000  -2.060  1.00  0.00           H  
HETATM   23  H5  UNL     1       0.472  -1.962   0.214  1.00  0.00           H  
HETATM   24  H6  UNL     1      -1.863  -2.479  -0.678  1.00  0.00           H  
HETATM   25  H7  UNL     1      -1.675  -1.168  -1.863  1.00  0.00           H  
HETATM   26  H8  UNL     1      -1.992  -1.857   1.656  1.00  0.00           H  
HETATM   27  H9  UNL     1      -2.618  -0.130   3.368  1.00  0.00           H  
HETATM   28  H10 UNL     1      -2.689   2.220   2.687  1.00  0.00           H  
HETATM   29  H11 UNL     1      -2.156   2.873   0.363  1.00  0.00           H  
HETATM   30  H12 UNL     1      -1.533   1.124  -1.327  1.00  0.00           H  
HETATM   31  H13 UNL     1       0.212  -4.512  -0.614  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   19
CONECT    4    5   20   21
CONECT    5    6    6    7
CONECT    7    8   22
CONECT    8    9   16   23
CONECT    9   10   24   25
CONECT   10   11   11   15
CONECT   11   12   26
CONECT   12   13   13   27
CONECT   13   14   28
CONECT   14   15   15   29
CONECT   15   30
CONECT   16   17   17   18
CONECT   18   31
END

HMDB0039102
     RDKit          3D
N-Carboxyacetyl-D-phenylalanine
 31 31  0  0  0  0  0  0  0  0999 V2000
    3.2194    1.4028    1.5033 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1095    2.0690    0.4643 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7533    3.2741    0.2525 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2371    1.5432   -0.6141 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6184    0.2515   -0.2443 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8826   -0.2453    0.8947 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7524   -0.4201   -1.1325 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1345   -1.6812   -0.7992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3697   -1.5248   -0.8775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7370   -0.4669    0.1075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0427   -0.7902    1.4184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3828    0.1674    2.3406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4194    1.4886    1.9439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1144    1.8185    0.6331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7702    0.8423   -0.2973 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5386   -2.7712   -1.7091 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3415   -2.5249   -2.6445 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0064   -4.0337   -1.4867 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3108    3.7528    0.9358 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4073    2.2820   -0.7322 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8189    1.4557   -1.5753 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5471    0.0002   -2.0600 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4717   -1.9619    0.2143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8628   -2.4792   -0.6780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6746   -1.1679   -1.8626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9919   -1.8572    1.6564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6178   -0.1295    3.3677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6893    2.2204    2.6871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1557    2.8733    0.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5328    1.1244   -1.3275 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2115   -4.5122   -0.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  8 16  1  0
 16 17  2  0
 16 18  1  0
 15 10  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 18 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-Malonyl-D-phenylalanine	HMDB
2-[(2-Carboxy-1-hydroxyethylidene)amino]-3-phenylpropanoate	Generator

Chemical Formula

C₁₂H₁₃NO₅

Average Molecular Weight

251.2353

Monoisotopic Molecular Weight

251.079372531

IUPAC Name

2-(2-carboxyacetamido)-3-phenylpropanoic acid

Traditional Name

2-(2-carboxyacetamido)-3-phenylpropanoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C12H13NO5/c14-10(7-11(15)16)13-9(12(17)18)6-8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H,13,14)(H,15,16)(H,17,18)

InChI Key

IHAMOIOWKITHQZ-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
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
3-phenylpropanoic-acid
Amphetamine or derivatives
Monocyclic benzene moiety
Benzenoid
Dicarboxylic acid or derivatives
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0039102)
Cytoplasm (HMDB: HMDB0039102)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039102)

Source

Exogenous

Exogenous (HMDB: HMDB0039102)

Food

Food (HMDB: HMDB0039102)

Pulse

Pulses (FooDB: FOOD00867)

Endogenous

Plant

Fabaceae (HMDB: HMDB0039102)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0039102)

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
Water Solubility	1.04 g/L	ALOGPS
logP	0.52	ALOGPS
logP	0.79	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	3.43	ChemAxon
pKa (Strongest Basic)	-6.1	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	103.7 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	60.9 m³·mol⁻¹	ChemAxon
Polarizability	24.03 Å³	ChemAxon
Number of Rings	1	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]+	157.378	31661259
DarkChem	[M-H]-	153.613	31661259
DeepCCS	[M+H]+	151.572	30932474
DeepCCS	[M-H]-	149.214	30932474
DeepCCS	[M-2H]-	182.333	30932474
DeepCCS	[M+Na]+	157.665	30932474
AllCCS	[M+H]+	155.6	32859911
AllCCS	[M+H-H2O]+	152.1	32859911
AllCCS	[M+NH4]+	158.9	32859911
AllCCS	[M+Na]+	159.9	32859911
AllCCS	[M-H]-	155.8	32859911
AllCCS	[M+Na-2H]-	155.9	32859911
AllCCS	[M+HCOO]-	156.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.72 minutes	32390414
Predicted by Siyang on May 30, 2022	10.6963 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.47 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	105.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1404.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	260.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	112.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	168.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	93.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	323.6 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	391.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	134.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	791.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	362.2 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	1101.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	234.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	262.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	377.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	195.3 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	136.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Carboxyacetyl-D-phenylalanine	OC(=O)CC(=O)NC(CC1=CC=CC=C1)C(O)=O	3764.4	Standard polar	33892256
N-Carboxyacetyl-D-phenylalanine	OC(=O)CC(=O)NC(CC1=CC=CC=C1)C(O)=O	1787.8	Standard non polar	33892256
N-Carboxyacetyl-D-phenylalanine	OC(=O)CC(=O)NC(CC1=CC=CC=C1)C(O)=O	2207.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Carboxyacetyl-D-phenylalanine,1TMS,isomer #1	C[Si](C)(C)OC(=O)CC(=O)NC(CC1=CC=CC=C1)C(=O)O	2157.0	Semi standard non polar	33892256
N-Carboxyacetyl-D-phenylalanine,1TMS,isomer #2	C[Si](C)(C)OC(=O)C(CC1=CC=CC=C1)NC(=O)CC(=O)O	2127.8	Semi standard non polar	33892256
N-Carboxyacetyl-D-phenylalanine,1TMS,isomer #3	C[Si](C)(C)N(C(=O)CC(=O)O)C(CC1=CC=CC=C1)C(=O)O	2159.6	Semi standard non polar	33892256
N-Carboxyacetyl-D-phenylalanine,2TMS,isomer #1	C[Si](C)(C)OC(=O)CC(=O)NC(CC1=CC=CC=C1)C(=O)O[Si](C)(C)C	2171.9	Semi standard non polar	33892256
N-Carboxyacetyl-D-phenylalanine,2TMS,isomer #2	C[Si](C)(C)OC(=O)CC(=O)N(C(CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	2170.4	Semi standard non polar	33892256
N-Carboxyacetyl-D-phenylalanine,2TMS,isomer #3	C[Si](C)(C)OC(=O)C(CC1=CC=CC=C1)N(C(=O)CC(=O)O)[Si](C)(C)C	2160.2	Semi standard non polar	33892256
N-Carboxyacetyl-D-phenylalanine,3TMS,isomer #1	C[Si](C)(C)OC(=O)CC(=O)N(C(CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2168.1	Semi standard non polar	33892256
N-Carboxyacetyl-D-phenylalanine,3TMS,isomer #1	C[Si](C)(C)OC(=O)CC(=O)N(C(CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2224.4	Standard non polar	33892256
N-Carboxyacetyl-D-phenylalanine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC(=O)NC(CC1=CC=CC=C1)C(=O)O	2398.8	Semi standard non polar	33892256
N-Carboxyacetyl-D-phenylalanine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=CC=C1)NC(=O)CC(=O)O	2357.5	Semi standard non polar	33892256
N-Carboxyacetyl-D-phenylalanine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C(=O)CC(=O)O)C(CC1=CC=CC=C1)C(=O)O	2397.9	Semi standard non polar	33892256
N-Carboxyacetyl-D-phenylalanine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC(=O)NC(CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C	2644.8	Semi standard non polar	33892256
N-Carboxyacetyl-D-phenylalanine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CC(=O)N(C(CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	2655.0	Semi standard non polar	33892256
N-Carboxyacetyl-D-phenylalanine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=CC=C1)N(C(=O)CC(=O)O)[Si](C)(C)C(C)(C)C	2641.1	Semi standard non polar	33892256
N-Carboxyacetyl-D-phenylalanine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC(=O)N(C(CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2853.5	Semi standard non polar	33892256
N-Carboxyacetyl-D-phenylalanine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC(=O)N(C(CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2817.2	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Carboxyacetyl-D-phenylalanine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9420000000-af53976345e3195393c2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Carboxyacetyl-D-phenylalanine GC-MS (2 TMS) - 70eV, Positive	splash10-00fu-9132000000-6c27c068628f6d7aea33	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Carboxyacetyl-D-phenylalanine 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-Carboxyacetyl-D-phenylalanine 10V, Positive-QTOF	splash10-0j59-2790000000-5f8a870aa0d130035078	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Carboxyacetyl-D-phenylalanine 20V, Positive-QTOF	splash10-02tc-3920000000-f715c1bb668dd56154d2	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Carboxyacetyl-D-phenylalanine 40V, Positive-QTOF	splash10-0006-9200000000-210dd1ff7f22334507eb	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Carboxyacetyl-D-phenylalanine 10V, Negative-QTOF	splash10-0zfr-2390000000-7eb09e89046baf62fc75	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Carboxyacetyl-D-phenylalanine 20V, Negative-QTOF	splash10-0bt9-4950000000-a58aff01c98d00c82bd8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Carboxyacetyl-D-phenylalanine 40V, Negative-QTOF	splash10-0aou-9400000000-7838fd7b9a8f48bad038	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Carboxyacetyl-D-phenylalanine 10V, Negative-QTOF	splash10-03di-1910000000-7db4361124869d109432	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Carboxyacetyl-D-phenylalanine 20V, Negative-QTOF	splash10-0007-7900000000-d5f2490dfd37f56957ef	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Carboxyacetyl-D-phenylalanine 40V, Negative-QTOF	splash10-0006-9400000000-78375bf0f570126802d2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Carboxyacetyl-D-phenylalanine 10V, Positive-QTOF	splash10-00xr-0920000000-26a158221670644f1f54	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Carboxyacetyl-D-phenylalanine 20V, Positive-QTOF	splash10-00di-0900000000-05f6ea01ce0553a59a32	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Carboxyacetyl-D-phenylalanine 40V, Positive-QTOF	splash10-00di-5900000000-5709da933cdeb32d533e	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB018608

KNApSAcK ID

Not Available

Chemspider ID

13634418

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21257164

PDB ID

Not Available

ChEBI ID

168088

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for N-Carboxyacetyl-D-phenylalanine (HMDB0039102)

MOL for HMDB0039102 (N-Carboxyacetyl-D-phenylalanine)

3D MOL for HMDB0039102 (N-Carboxyacetyl-D-phenylalanine)

3D SDF for HMDB0039102 (N-Carboxyacetyl-D-phenylalanine)

3D-SDF for HMDB0039102 (N-Carboxyacetyl-D-phenylalanine)

PDB for HMDB0039102 (N-Carboxyacetyl-D-phenylalanine)

3D PDB for HMDB0039102 (N-Carboxyacetyl-D-phenylalanine)

SMILES for HMDB0039102 (N-Carboxyacetyl-D-phenylalanine)

INCHI for HMDB0039102 (N-Carboxyacetyl-D-phenylalanine)

Structure for HMDB0039102 (N-Carboxyacetyl-D-phenylalanine)

3D Structure for HMDB0039102 (N-Carboxyacetyl-D-phenylalanine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra