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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2009-02-24 09:13:55 UTC

Update Date

2021-09-14 15:47:12 UTC

HMDB ID

HMDB0011716

Secondary Accession Numbers

HMDB11716

Metabolite Identification

Common Name

N-Acetylvanilalanine

Description

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

Structure

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

HMDB0011716
     RDKit          3D
N-Acetylvanilalanine
 33 33  0  0  0  0  0  0  0  0999 V2000
   -4.0407    1.8853    1.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9981    0.5501    0.7804 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9566   -0.1098    0.2831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7001    0.4923    0.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6128   -0.0792   -0.4972 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7119    0.5107   -0.4846 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8077   -0.5285   -0.4347 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0555    0.0118   -0.3823 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2891    0.5398   -0.3317 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2668    2.0691   -0.0439 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4508    0.0558   -0.4638 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5290   -1.7272    0.3229 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1316   -2.8174    0.2493 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4587   -1.6746    1.2664 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8118   -1.3300   -0.9976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9953   -2.0199   -0.8806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0152   -1.3920   -0.2474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2418   -2.0628   -0.1076 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1525    2.1244    2.1167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9266    2.3674    0.4772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1698    2.4372    0.6468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5524    1.5073    0.6191 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8771    1.0820    0.5001 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8080    1.2052   -1.3267 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7294   -1.0055   -1.5693 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6461   -1.2666   -0.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9835    2.1535    1.0164 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2136    2.5410   -0.2456 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4534    2.5386   -0.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8552   -1.4904    2.2429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0067   -1.7903   -1.5587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0503   -3.0175   -1.2894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0366   -1.7599    0.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
  7 12  1  0
 12 13  2  0
 12 14  1  0
  5 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17  3  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  6 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
 10 27  1  0
 10 28  1  0
 10 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 18 33  1  0
M  END


  Mrv0541 02241201522D          

 18 18  0  0  0  0            999 V2000
   11.0897   -2.8278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6771   -3.5423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0897   -4.2568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9147   -4.2568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3272   -4.9713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1522   -4.9713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5647   -4.2568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3897   -4.2568    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1522   -3.5423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5647   -2.8278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3272   -3.5423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9147   -5.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0897   -5.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6771   -4.9713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8521   -4.9713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8022   -3.5423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6272   -3.5423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3897   -2.8278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3 14  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5 12  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
  8 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0011716

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(CC(NC(C)=O)C(O)=O)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C12H15NO5/c1-7(14)13-9(12(16)17)5-8-3-4-10(15)11(6-8)18-2/h3-4,6,9,15H,5H2,1-2H3,(H,13,14)(H,16,17)

> <INCHI_KEY>
UKDKTHYZLXZOSS-UHFFFAOYSA-N

> <FORMULA>
C12H15NO5

> <MOLECULAR_WEIGHT>
253.2512

> <EXACT_MASS>
253.095022595

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
25.07337297332647

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-acetamido-3-(4-hydroxy-3-methoxyphenyl)propanoic acid

> <ALOGPS_LOGP>
1.25

> <JCHEM_LOGP>
0.43522506866666627

> <ALOGPS_LOGS>
-2.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.94511065386889

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.479612836431998

> <JCHEM_PKA_STRONGEST_BASIC>
-1.4774978347489918

> <JCHEM_POLAR_SURFACE_AREA>
95.85999999999999

> <JCHEM_REFRACTIVITY>
63.00420000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.29e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-acetamido-3-(4-hydroxy-3-methoxyphenyl)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0011716
     RDKit          3D
N-Acetylvanilalanine
 33 33  0  0  0  0  0  0  0  0999 V2000
   -4.0407    1.8853    1.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9981    0.5501    0.7804 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9566   -0.1098    0.2831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7001    0.4923    0.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6128   -0.0792   -0.4972 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7119    0.5107   -0.4846 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8077   -0.5285   -0.4347 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0555    0.0118   -0.3823 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2891    0.5398   -0.3317 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2668    2.0691   -0.0439 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4508    0.0558   -0.4638 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5290   -1.7272    0.3229 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1316   -2.8174    0.2493 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4587   -1.6746    1.2664 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8118   -1.3300   -0.9976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9953   -2.0199   -0.8806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0152   -1.3920   -0.2474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2418   -2.0628   -0.1076 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1525    2.1244    2.1167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9266    2.3674    0.4772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1698    2.4372    0.6468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5524    1.5073    0.6191 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8771    1.0820    0.5001 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8080    1.2052   -1.3267 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7294   -1.0055   -1.5693 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6461   -1.2666   -0.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9835    2.1535    1.0164 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2136    2.5410   -0.2456 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4534    2.5386   -0.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8552   -1.4904    2.2429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0067   -1.7903   -1.5587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0503   -3.0175   -1.2894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0366   -1.7599    0.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
  7 12  1  0
 12 13  2  0
 12 14  1  0
  5 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17  3  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  6 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
 10 27  1  0
 10 28  1  0
 10 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 18 33  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  C   UNK     0      20.701  -5.279   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      19.931  -6.612   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      20.701  -7.946   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      22.241  -7.946   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      23.011  -9.280   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      24.551  -9.280   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      25.321  -7.946   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      26.861  -7.946   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      24.551  -6.612   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      25.321  -5.279   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      23.011  -6.612   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      22.241 -10.613   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      20.701 -10.613   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      19.931  -9.280   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      18.391  -9.280   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      27.631  -6.612   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      29.171  -6.612   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      26.861  -5.279   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7   16                                                       
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    5   13                                                       
CONECT   13   12   14                                                       
CONECT   14    3   13   15                                                  
CONECT   15   14                                                            
CONECT   16    8   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0011716
HETATM    1  C1  UNL     1      -4.041   1.885   1.082  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.998   0.550   0.780  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.957  -0.110   0.283  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.700   0.492   0.137  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.613  -0.079  -0.497  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.712   0.511  -0.485  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.808  -0.529  -0.435  1.00  0.00           C  
HETATM    8  N1  UNL     1       3.055   0.012  -0.382  1.00  0.00           N  
HETATM    9  C7  UNL     1       4.289   0.540  -0.332  1.00  0.00           C  
HETATM   10  C8  UNL     1       4.267   2.069  -0.044  1.00  0.00           C  
HETATM   11  O2  UNL     1       5.451   0.056  -0.464  1.00  0.00           O  
HETATM   12  C9  UNL     1       1.529  -1.727   0.323  1.00  0.00           C  
HETATM   13  O3  UNL     1       2.132  -2.817   0.249  1.00  0.00           O  
HETATM   14  O4  UNL     1       0.459  -1.675   1.266  1.00  0.00           O  
HETATM   15  C10 UNL     1      -0.812  -1.330  -0.998  1.00  0.00           C  
HETATM   16  C11 UNL     1      -1.995  -2.020  -0.881  1.00  0.00           C  
HETATM   17  C12 UNL     1      -3.015  -1.392  -0.247  1.00  0.00           C  
HETATM   18  O5  UNL     1      -4.242  -2.063  -0.108  1.00  0.00           O  
HETATM   19  H1  UNL     1      -4.153   2.124   2.117  1.00  0.00           H  
HETATM   20  H2  UNL     1      -4.927   2.367   0.477  1.00  0.00           H  
HETATM   21  H3  UNL     1      -3.170   2.437   0.647  1.00  0.00           H  
HETATM   22  H4  UNL     1      -1.552   1.507   0.619  1.00  0.00           H  
HETATM   23  H5  UNL     1       0.877   1.082   0.500  1.00  0.00           H  
HETATM   24  H6  UNL     1       0.808   1.205  -1.327  1.00  0.00           H  
HETATM   25  H7  UNL     1       1.729  -1.006  -1.569  1.00  0.00           H  
HETATM   26  H8  UNL     1       3.646  -1.267  -0.470  1.00  0.00           H  
HETATM   27  H9  UNL     1       3.984   2.154   1.016  1.00  0.00           H  
HETATM   28  H10 UNL     1       5.214   2.541  -0.246  1.00  0.00           H  
HETATM   29  H11 UNL     1       3.453   2.539  -0.701  1.00  0.00           H  
HETATM   30  H12 UNL     1       0.855  -1.490   2.243  1.00  0.00           H  
HETATM   31  H13 UNL     1      -0.007  -1.790  -1.559  1.00  0.00           H  
HETATM   32  H14 UNL     1      -2.050  -3.018  -1.289  1.00  0.00           H  
HETATM   33  H15 UNL     1      -5.037  -1.760   0.382  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3
CONECT    3    4    4   17
CONECT    4    5   22
CONECT    5    6   15   15
CONECT    6    7   23   24
CONECT    7    8   12   25
CONECT    8    9   26
CONECT    9   10   11   11
CONECT   10   27   28   29
CONECT   12   13   13   14
CONECT   14   30
CONECT   15   16   31
CONECT   16   17   17   32
CONECT   17   18
CONECT   18   33
END

HMDB0011716
     RDKit          3D
N-Acetylvanilalanine
 33 33  0  0  0  0  0  0  0  0999 V2000
   -4.0407    1.8853    1.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9981    0.5501    0.7804 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9566   -0.1098    0.2831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7001    0.4923    0.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6128   -0.0792   -0.4972 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7119    0.5107   -0.4846 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8077   -0.5285   -0.4347 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0555    0.0118   -0.3823 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2891    0.5398   -0.3317 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2668    2.0691   -0.0439 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4508    0.0558   -0.4638 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5290   -1.7272    0.3229 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1316   -2.8174    0.2493 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4587   -1.6746    1.2664 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8118   -1.3300   -0.9976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9953   -2.0199   -0.8806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0152   -1.3920   -0.2474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2418   -2.0628   -0.1076 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1525    2.1244    2.1167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9266    2.3674    0.4772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1698    2.4372    0.6468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5524    1.5073    0.6191 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8771    1.0820    0.5001 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8080    1.2052   -1.3267 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7294   -1.0055   -1.5693 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6461   -1.2666   -0.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9835    2.1535    1.0164 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2136    2.5410   -0.2456 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4534    2.5386   -0.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8552   -1.4904    2.2429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0067   -1.7903   -1.5587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0503   -3.0175   -1.2894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0366   -1.7599    0.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
  7 12  1  0
 12 13  2  0
 12 14  1  0
  5 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17  3  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  6 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
 10 27  1  0
 10 28  1  0
 10 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 18 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-Acetyl-vanilalanine	HMDB
3-(4-Hydroxy-3-methoxyphenyl)-2-[(1-hydroxyethylidene)amino]propanoate	Generator, HMDB

Chemical Formula

C₁₂H₁₅NO₅

Average Molecular Weight

253.2512

Monoisotopic Molecular Weight

253.095022595

IUPAC Name

2-acetamido-3-(4-hydroxy-3-methoxyphenyl)propanoic acid

Traditional Name

2-acetamido-3-(4-hydroxy-3-methoxyphenyl)propanoic acid

CAS Registry Number

Not Available

SMILES

COC1=CC(CC(NC(C)=O)C(O)=O)=CC=C1O

InChI Identifier

InChI=1S/C12H15NO5/c1-7(14)13-9(12(16)17)5-8-3-4-10(15)11(6-8)18-2/h3-4,6,9,15H,5H2,1-2H3,(H,13,14)(H,16,17)

InChI Key

UKDKTHYZLXZOSS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine 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

Tyrosine and derivatives

Alternative Parents

Substituents

Tyrosine or derivatives
Phenylalanine or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
3-phenylpropanoic-acid
Amphetamine or derivatives
Methoxyphenol
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Acetamide
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid
Ether
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organooxygen compound
Organopnictogen compound
Organonitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Health effect

Genetic disorder

Inborn errors of metabolism

Aromatic L-amino acid decarboxylase deficiency (HMDB: HMDB0011716)

Urine (PMID: 16288991)

Source

Endogenous

Endogenous (HMDB: HMDB0011716)

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	2.29 g/L	ALOGPS
logP	1.25	ALOGPS
logP	0.44	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	3.48	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	95.86 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	63 m³·mol⁻¹	ChemAxon
Polarizability	25.07 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]+	161.711	31661259
DarkChem	[M-H]-	160.448	31661259
DeepCCS	[M+H]+	155.031	30932474
DeepCCS	[M-H]-	152.673	30932474
DeepCCS	[M-2H]-	185.813	30932474
DeepCCS	[M+Na]+	161.124	30932474
AllCCS	[M+H]+	157.8	32859911
AllCCS	[M+H-H2O]+	154.2	32859911
AllCCS	[M+NH4]+	161.1	32859911
AllCCS	[M+Na]+	162.1	32859911
AllCCS	[M-H]-	157.4	32859911
AllCCS	[M+Na-2H]-	157.7	32859911
AllCCS	[M+HCOO]-	158.2	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.	3.12 minutes	32390414
Predicted by Siyang on May 30, 2022	9.9587 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.33 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	94.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1333.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	225.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	99.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	156.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	64.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	323.8 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	313.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	157.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	724.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	325.7 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	1024.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	215.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	242.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	397.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	254.4 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	150.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Acetylvanilalanine	COC1=CC(CC(NC(C)=O)C(O)=O)=CC=C1O	3818.0	Standard polar	33892256
N-Acetylvanilalanine	COC1=CC(CC(NC(C)=O)C(O)=O)=CC=C1O	2229.2	Standard non polar	33892256
N-Acetylvanilalanine	COC1=CC(CC(NC(C)=O)C(O)=O)=CC=C1O	2234.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Acetylvanilalanine,1TMS,isomer #1	COC1=CC(CC(NC(C)=O)C(=O)O[Si](C)(C)C)=CC=C1O	2207.6	Semi standard non polar	33892256
N-Acetylvanilalanine,1TMS,isomer #2	COC1=CC(CC(NC(C)=O)C(=O)O)=CC=C1O[Si](C)(C)C	2250.7	Semi standard non polar	33892256
N-Acetylvanilalanine,1TMS,isomer #3	COC1=CC(CC(C(=O)O)N(C(C)=O)[Si](C)(C)C)=CC=C1O	2189.6	Semi standard non polar	33892256
N-Acetylvanilalanine,2TMS,isomer #1	COC1=CC(CC(NC(C)=O)C(=O)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2235.5	Semi standard non polar	33892256
N-Acetylvanilalanine,2TMS,isomer #2	COC1=CC(CC(C(=O)O[Si](C)(C)C)N(C(C)=O)[Si](C)(C)C)=CC=C1O	2140.4	Semi standard non polar	33892256
N-Acetylvanilalanine,2TMS,isomer #3	COC1=CC(CC(C(=O)O)N(C(C)=O)[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2212.7	Semi standard non polar	33892256
N-Acetylvanilalanine,3TMS,isomer #1	COC1=CC(CC(C(=O)O[Si](C)(C)C)N(C(C)=O)[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2224.5	Semi standard non polar	33892256
N-Acetylvanilalanine,3TMS,isomer #1	COC1=CC(CC(C(=O)O[Si](C)(C)C)N(C(C)=O)[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2269.7	Standard non polar	33892256
N-Acetylvanilalanine,3TMS,isomer #1	COC1=CC(CC(C(=O)O[Si](C)(C)C)N(C(C)=O)[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2536.6	Standard polar	33892256
N-Acetylvanilalanine,1TBDMS,isomer #1	COC1=CC(CC(NC(C)=O)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O	2484.4	Semi standard non polar	33892256
N-Acetylvanilalanine,1TBDMS,isomer #2	COC1=CC(CC(NC(C)=O)C(=O)O)=CC=C1O[Si](C)(C)C(C)(C)C	2527.9	Semi standard non polar	33892256
N-Acetylvanilalanine,1TBDMS,isomer #3	COC1=CC(CC(C(=O)O)N(C(C)=O)[Si](C)(C)C(C)(C)C)=CC=C1O	2458.2	Semi standard non polar	33892256
N-Acetylvanilalanine,2TBDMS,isomer #1	COC1=CC(CC(NC(C)=O)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2751.4	Semi standard non polar	33892256
N-Acetylvanilalanine,2TBDMS,isomer #2	COC1=CC(CC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(C)=O)[Si](C)(C)C(C)(C)C)=CC=C1O	2657.3	Semi standard non polar	33892256
N-Acetylvanilalanine,2TBDMS,isomer #3	COC1=CC(CC(C(=O)O)N(C(C)=O)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2732.4	Semi standard non polar	33892256
N-Acetylvanilalanine,3TBDMS,isomer #1	COC1=CC(CC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(C)=O)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2934.8	Semi standard non polar	33892256
N-Acetylvanilalanine,3TBDMS,isomer #1	COC1=CC(CC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(C)=O)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2906.0	Standard non polar	33892256
N-Acetylvanilalanine,3TBDMS,isomer #1	COC1=CC(CC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(C)=O)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2883.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetylvanilalanine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9530000000-88e789bd50bcb7d1ca90	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetylvanilalanine GC-MS (2 TMS) - 70eV, Positive	splash10-00dl-9014000000-dda2c49be0e1b55e83da	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetylvanilalanine 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-Acetylvanilalanine 10V, Positive-QTOF	splash10-0udr-0290000000-7593dceb7a0c284d48db	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylvanilalanine 20V, Positive-QTOF	splash10-07vr-1970000000-4df59618dbc09ea1fe41	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylvanilalanine 40V, Positive-QTOF	splash10-0avr-4900000000-2639c0e6bef8583c7b1c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylvanilalanine 10V, Negative-QTOF	splash10-0udi-0190000000-73b12fcdc611e96a0765	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylvanilalanine 20V, Negative-QTOF	splash10-0rkc-5790000000-b29af3d062fafe86098d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylvanilalanine 40V, Negative-QTOF	splash10-052f-9500000000-057477279b85a32a5bda	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylvanilalanine 10V, Positive-QTOF	splash10-0k9i-0390000000-bdbcdae4f6b362d04067	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylvanilalanine 20V, Positive-QTOF	splash10-0006-1900000000-264e5b9060dd7a86cc6d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylvanilalanine 40V, Positive-QTOF	splash10-000i-2900000000-16d00125d12d59ab6b9a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylvanilalanine 10V, Negative-QTOF	splash10-0w29-2190000000-b9cf26a60b71f07e68e8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylvanilalanine 20V, Negative-QTOF	splash10-00di-9620000000-5a60924c52bbe2baa063	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylvanilalanine 40V, Negative-QTOF	splash10-007c-9400000000-52e667ed44aedb28a8f9	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	10 +/- 2 umol/mmol creatinine	Infant (0-1 year old)	Male	Aromatic L-amino acid decarboxylase deficiency	16288991	details

Associated Disorders and Diseases

Disease References

Aromatic L-amino acid decarboxylase deficiency
Abdenur JE, Abeling N, Specola N, Jorge L, Schenone AB, van Cruchten AC, Chamoles NA: Aromatic l-aminoacid decarboxylase deficiency: unusual neonatal presentation and additional findings in organic acid analysis. Mol Genet Metab. 2006 Jan;87(1):48-53. Epub 2005 Nov 9. [PubMed:16288991 ]

Associated OMIM IDs

608643 (Aromatic L-amino acid decarboxylase deficiency)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028401

KNApSAcK ID

Not Available

Chemspider ID

15185955

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12681285

PDB ID

Not Available

ChEBI ID

88403

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

Abdenur JE, Abeling N, Specola N, Jorge L, Schenone AB, van Cruchten AC, Chamoles NA: Aromatic l-aminoacid decarboxylase deficiency: unusual neonatal presentation and additional findings in organic acid analysis. Mol Genet Metab. 2006 Jan;87(1):48-53. Epub 2005 Nov 9. [PubMed:16288991 ]

Showing metabocard for N-Acetylvanilalanine (HMDB0011716)

MOL for HMDB0011716 (N-Acetylvanilalanine)

3D MOL for HMDB0011716 (N-Acetylvanilalanine)

3D SDF for HMDB0011716 (N-Acetylvanilalanine)

3D-SDF for HMDB0011716 (N-Acetylvanilalanine)

PDB for HMDB0011716 (N-Acetylvanilalanine)

3D PDB for HMDB0011716 (N-Acetylvanilalanine)

SMILES for HMDB0011716 (N-Acetylvanilalanine)

INCHI for HMDB0011716 (N-Acetylvanilalanine)

Structure for HMDB0011716 (N-Acetylvanilalanine)

3D Structure for HMDB0011716 (N-Acetylvanilalanine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra