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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2016-10-26 16:26:49 UTC

Update Date

2021-09-14 15:41:37 UTC

HMDB ID

HMDB0062175

Secondary Accession Numbers

HMDB62175

Metabolite Identification

Common Name

N-Lactoylphenylalanine

Description

N-Lactoylphenylalanine is a lactoyl derivative of phenylalanine. N-Lactoyl-amino acids are ubiquitous pseudodipeptides of lactic acid and amino acids that are rapidly formed by reverse proteolysis. A protease, cytosolic nonspecific dipeptidase 2 (CNDP2), catalyzes their formation. The plasma levels of these metabolites strongly correlate with plasma levels of lactate and amino acid (PMID: 25964343 ).

Structure

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

HMDB0062175
     RDKit          3D
N-Lactoylphenylalanine
 32 32  0  0  0  0  0  0  0  0999 V2000
   -4.2847    1.8126    0.3088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0236    0.3168    0.0893 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0741   -0.2904    1.3384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6390    0.2090   -0.4205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4067    0.7120   -1.5512 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6445   -0.4355    0.3506 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2790   -0.5395   -0.1573 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6074    0.1946    0.8331 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0227    0.1985    0.4981 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5321    1.1921   -0.3039 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8776    1.2462   -0.6484 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7267    0.2656   -0.1655 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2098   -0.7261    0.6370 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8585   -0.7776    0.9812 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0751   -1.9705   -0.2180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7492   -2.8333    0.1561 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3155   -2.3711   -0.6877 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3485    2.2119    0.7583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1688    1.9888    0.9343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3584    2.2539   -0.7082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7664   -0.1082   -0.6151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9098   -1.2514    1.3172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8924   -0.8326    1.2773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2060   -0.0538   -1.1686 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4487   -0.3334    1.8170 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1774    1.2154    0.9807 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8905    1.9796   -0.7009 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2843    2.0218   -1.2767 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7939    0.2911   -0.4266 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8628   -1.5000    1.0221 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5256   -1.6013    1.6312 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5425   -2.4853   -1.6598 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  7 15  1  0
 15 16  2  0
 15 17  1  0
 14  9  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  6
  3 22  1  0
  6 23  1  0
  7 24  1  6
  8 25  1  0
  8 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 17 32  1  0
M  END


  Mrv1652310261618262D          

 17 17  0  0  0  0            999 V2000
    0.0445    1.8296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6698    1.4171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6698    0.5919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0445    0.1794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7591    0.5919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7591    1.4171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3843    0.1794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3843   -0.6455    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0989   -1.0581    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8134   -0.6455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5279   -1.0581    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2424   -0.6455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5279   -1.8831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8134    0.1794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6698   -1.0581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6698   -1.8831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0446   -0.6455    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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  3  7  1  0  0  0  0
  8  7  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  8 15  1  0  0  0  0
 15 17  1  0  0  0  0
 15 16  2  0  0  0  0
 10 14  2  0  0  0  0
 11 13  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0062175

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H15NO4/c1-8(14)11(15)13-10(12(16)17)7-9-5-3-2-4-6-9/h2-6,8,10,14H,7H2,1H3,(H,13,15)(H,16,17)/t8-,10-/m0/s1

> <INCHI_KEY>
IIRJJZHHNGABMQ-WPRPVWTQSA-N

> <FORMULA>
C12H15NO4

> <MOLECULAR_WEIGHT>
237.255

> <EXACT_MASS>
237.100107967

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
24.088176761139

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-[(2S)-2-hydroxypropanamido]-3-phenylpropanoic acid

> <ALOGPS_LOGP>
0.47

> <JCHEM_LOGP>
0.6479778523333328

> <ALOGPS_LOGS>
-1.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.966197380378055

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9359014274350637

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4633610488133364

> <JCHEM_POLAR_SURFACE_AREA>
86.63000000000001

> <JCHEM_REFRACTIVITY>
60.7562

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.62e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(2S)-2-hydroxypropanamido]-3-phenylpropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0062175
     RDKit          3D
N-Lactoylphenylalanine
 32 32  0  0  0  0  0  0  0  0999 V2000
   -4.2847    1.8126    0.3088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0236    0.3168    0.0893 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0741   -0.2904    1.3384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6390    0.2090   -0.4205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4067    0.7120   -1.5512 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6445   -0.4355    0.3506 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2790   -0.5395   -0.1573 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6074    0.1946    0.8331 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0227    0.1985    0.4981 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5321    1.1921   -0.3039 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8776    1.2462   -0.6484 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7267    0.2656   -0.1655 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2098   -0.7261    0.6370 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8585   -0.7776    0.9812 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0751   -1.9705   -0.2180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7492   -2.8333    0.1561 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3155   -2.3711   -0.6877 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3485    2.2119    0.7583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1688    1.9888    0.9343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3584    2.2539   -0.7082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7664   -0.1082   -0.6151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9098   -1.2514    1.3172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8924   -0.8326    1.2773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2060   -0.0538   -1.1686 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4487   -0.3334    1.8170 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1774    1.2154    0.9807 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8905    1.9796   -0.7009 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2843    2.0218   -1.2767 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7939    0.2911   -0.4266 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8628   -1.5000    1.0221 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5256   -1.6013    1.6312 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5425   -2.4853   -1.6598 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  7 15  1  0
 15 16  2  0
 15 17  1  0
 14  9  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  6
  3 22  1  0
  6 23  1  0
  7 24  1  6
  8 25  1  0
  8 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 17 32  1  0
M  END

HEADER    PROTEIN                                 26-OCT-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-OCT-16         0                                  
HETATM    1  C   UNK     0       0.083   3.415   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.250   2.645   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.250   1.105   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.083   0.335   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.417   1.105   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.417   2.645   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.584   0.335   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.584  -1.205   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -3.918  -1.975   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -5.252  -1.205   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.585  -1.975   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -7.919  -1.205   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -6.585  -3.515   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -5.252   0.335   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.250  -1.975   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.250  -3.515   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.083  -1.205   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    3    8                                                       
CONECT    8    7   15    9                                                  
CONECT    9    8   10                                                       
CONECT   10   11   14    9                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   10                                                            
CONECT   15    8   17   16                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0062175
HETATM    1  C1  UNL     1      -4.285   1.813   0.309  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.024   0.317   0.089  1.00  0.00           C  
HETATM    3  O1  UNL     1      -4.074  -0.290   1.338  1.00  0.00           O  
HETATM    4  C3  UNL     1      -2.639   0.209  -0.421  1.00  0.00           C  
HETATM    5  O2  UNL     1      -2.407   0.712  -1.551  1.00  0.00           O  
HETATM    6  N1  UNL     1      -1.644  -0.435   0.351  1.00  0.00           N  
HETATM    7  C4  UNL     1      -0.279  -0.540  -0.157  1.00  0.00           C  
HETATM    8  C5  UNL     1       0.607   0.195   0.833  1.00  0.00           C  
HETATM    9  C6  UNL     1       2.023   0.198   0.498  1.00  0.00           C  
HETATM   10  C7  UNL     1       2.532   1.192  -0.304  1.00  0.00           C  
HETATM   11  C8  UNL     1       3.878   1.246  -0.648  1.00  0.00           C  
HETATM   12  C9  UNL     1       4.727   0.266  -0.166  1.00  0.00           C  
HETATM   13  C10 UNL     1       4.210  -0.726   0.637  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.858  -0.778   0.981  1.00  0.00           C  
HETATM   15  C12 UNL     1       0.075  -1.970  -0.218  1.00  0.00           C  
HETATM   16  O3  UNL     1      -0.749  -2.833   0.156  1.00  0.00           O  
HETATM   17  O4  UNL     1       1.315  -2.371  -0.688  1.00  0.00           O  
HETATM   18  H1  UNL     1      -3.348   2.212   0.758  1.00  0.00           H  
HETATM   19  H2  UNL     1      -5.169   1.989   0.934  1.00  0.00           H  
HETATM   20  H3  UNL     1      -4.358   2.254  -0.708  1.00  0.00           H  
HETATM   21  H4  UNL     1      -4.766  -0.108  -0.615  1.00  0.00           H  
HETATM   22  H5  UNL     1      -3.910  -1.251   1.317  1.00  0.00           H  
HETATM   23  H6  UNL     1      -1.892  -0.833   1.277  1.00  0.00           H  
HETATM   24  H7  UNL     1      -0.206  -0.054  -1.169  1.00  0.00           H  
HETATM   25  H8  UNL     1       0.449  -0.333   1.817  1.00  0.00           H  
HETATM   26  H9  UNL     1       0.177   1.215   0.981  1.00  0.00           H  
HETATM   27  H10 UNL     1       1.890   1.980  -0.701  1.00  0.00           H  
HETATM   28  H11 UNL     1       4.284   2.022  -1.277  1.00  0.00           H  
HETATM   29  H12 UNL     1       5.794   0.291  -0.427  1.00  0.00           H  
HETATM   30  H13 UNL     1       4.863  -1.500   1.022  1.00  0.00           H  
HETATM   31  H14 UNL     1       2.526  -1.601   1.631  1.00  0.00           H  
HETATM   32  H15 UNL     1       1.543  -2.485  -1.660  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    4   21
CONECT    3   22
CONECT    4    5    5    6
CONECT    6    7   23
CONECT    7    8   15   24
CONECT    8    9   25   26
CONECT    9   10   10   14
CONECT   10   11   27
CONECT   11   12   12   28
CONECT   12   13   29
CONECT   13   14   14   30
CONECT   14   31
CONECT   15   16   16   17
CONECT   17   32
END

HMDB0062175
     RDKit          3D
N-Lactoylphenylalanine
 32 32  0  0  0  0  0  0  0  0999 V2000
   -4.2847    1.8126    0.3088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0236    0.3168    0.0893 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0741   -0.2904    1.3384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6390    0.2090   -0.4205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4067    0.7120   -1.5512 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6445   -0.4355    0.3506 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2790   -0.5395   -0.1573 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6074    0.1946    0.8331 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0227    0.1985    0.4981 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5321    1.1921   -0.3039 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8776    1.2462   -0.6484 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7267    0.2656   -0.1655 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2098   -0.7261    0.6370 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8585   -0.7776    0.9812 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0751   -1.9705   -0.2180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7492   -2.8333    0.1561 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3155   -2.3711   -0.6877 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3485    2.2119    0.7583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1688    1.9888    0.9343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3584    2.2539   -0.7082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7664   -0.1082   -0.6151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9098   -1.2514    1.3172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8924   -0.8326    1.2773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2060   -0.0538   -1.1686 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4487   -0.3334    1.8170 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1774    1.2154    0.9807 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8905    1.9796   -0.7009 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2843    2.0218   -1.2767 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7939    0.2911   -0.4266 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8628   -1.5000    1.0221 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5256   -1.6013    1.6312 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5425   -2.4853   -1.6598 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  7 15  1  0
 15 16  2  0
 15 17  1  0
 14  9  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  6
  3 22  1  0
  6 23  1  0
  7 24  1  6
  8 25  1  0
  8 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 17 32  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2S)-2-{[(2S)-1,2-dihydroxypropylidene]amino}-3-phenylpropanoate	Generator
N-Lactoyl-phenylalanine	HMDB

Chemical Formula

C₁₂H₁₅NO₄

Average Molecular Weight

237.255

Monoisotopic Molecular Weight

237.100107967

IUPAC Name

(2S)-2-[(2S)-2-hydroxypropanamido]-3-phenylpropanoic acid

Traditional Name

(2S)-2-[(2S)-2-hydroxypropanamido]-3-phenylpropanoic acid

CAS Registry Number

183241-73-8

SMILES

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

InChI Identifier

InChI=1S/C12H15NO4/c1-8(14)11(15)13-10(12(16)17)7-9-5-3-2-4-6-9/h2-6,8,10,14H,7H2,1H3,(H,13,15)(H,16,17)/t8-,10-/m0/s1

InChI Key

IIRJJZHHNGABMQ-WPRPVWTQSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Phenylalanine and derivatives

Alternative Parents

Substituents

Phenylalanine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
N-acyl-l-alpha-amino acid
3-phenylpropanoic-acid
Amphetamine or derivatives
Monocyclic benzene moiety
Benzenoid
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
Organic nitrogen 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: 25964343)

Source

Exogenous

Exogenous (HMDB: HMDB0062175)

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	0.47	ALOGPS
logP	0.65	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	3.94	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.63 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	60.76 m³·mol⁻¹	ChemAxon
Polarizability	24.09 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
DeepCCS	[M+H]+	156.808	30932474
DeepCCS	[M-H]-	154.412	30932474
DeepCCS	[M-2H]-	187.34	30932474
DeepCCS	[M+Na]+	162.781	30932474
AllCCS	[M+H]+	154.8	32859911
AllCCS	[M+H-H2O]+	151.1	32859911
AllCCS	[M+NH4]+	158.2	32859911
AllCCS	[M+Na]+	159.1	32859911
AllCCS	[M-H]-	154.3	32859911
AllCCS	[M+Na-2H]-	154.6	32859911
AllCCS	[M+HCOO]-	155.2	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.	3.87 minutes	32390414
Predicted by Siyang on May 30, 2022	10.9755 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.24 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1557.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	274.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	118.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	167.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	98.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	354.6 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	430.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	104.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	847.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	381.8 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	1159.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	244.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	288.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	319.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	187.5 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	83.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Lactoylphenylalanine	C[C@H](O)C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O	3630.9	Standard polar	33892256
N-Lactoylphenylalanine	C[C@H](O)C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O	1843.8	Standard non polar	33892256
N-Lactoylphenylalanine	C[C@H](O)C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O	2013.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Lactoylphenylalanine,1TMS,isomer #1	C[C@H](O[Si](C)(C)C)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O	2038.4	Semi standard non polar	33892256
N-Lactoylphenylalanine,1TMS,isomer #2	C[C@H](O)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C	1989.0	Semi standard non polar	33892256
N-Lactoylphenylalanine,1TMS,isomer #3	C[C@H](O)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	1974.6	Semi standard non polar	33892256
N-Lactoylphenylalanine,2TMS,isomer #1	C[C@H](O[Si](C)(C)C)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C	2035.9	Semi standard non polar	33892256
N-Lactoylphenylalanine,2TMS,isomer #2	C[C@H](O[Si](C)(C)C)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	2029.0	Semi standard non polar	33892256
N-Lactoylphenylalanine,2TMS,isomer #3	C[C@H](O)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1984.6	Semi standard non polar	33892256
N-Lactoylphenylalanine,3TMS,isomer #1	C[C@H](O[Si](C)(C)C)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2050.7	Semi standard non polar	33892256
N-Lactoylphenylalanine,3TMS,isomer #1	C[C@H](O[Si](C)(C)C)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2110.5	Standard non polar	33892256
N-Lactoylphenylalanine,3TMS,isomer #1	C[C@H](O[Si](C)(C)C)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2338.3	Standard polar	33892256
N-Lactoylphenylalanine,1TBDMS,isomer #1	C[C@H](O[Si](C)(C)C(C)(C)C)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O	2280.1	Semi standard non polar	33892256
N-Lactoylphenylalanine,1TBDMS,isomer #2	C[C@H](O)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C	2241.2	Semi standard non polar	33892256
N-Lactoylphenylalanine,1TBDMS,isomer #3	C[C@H](O)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	2227.6	Semi standard non polar	33892256
N-Lactoylphenylalanine,2TBDMS,isomer #1	C[C@H](O[Si](C)(C)C(C)(C)C)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C	2512.7	Semi standard non polar	33892256
N-Lactoylphenylalanine,2TBDMS,isomer #2	C[C@H](O[Si](C)(C)C(C)(C)C)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	2514.8	Semi standard non polar	33892256
N-Lactoylphenylalanine,2TBDMS,isomer #3	C[C@H](O)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2482.2	Semi standard non polar	33892256
N-Lactoylphenylalanine,3TBDMS,isomer #1	C[C@H](O[Si](C)(C)C(C)(C)C)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2733.3	Semi standard non polar	33892256
N-Lactoylphenylalanine,3TBDMS,isomer #1	C[C@H](O[Si](C)(C)C(C)(C)C)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2712.2	Standard non polar	33892256
N-Lactoylphenylalanine,3TBDMS,isomer #1	C[C@H](O[Si](C)(C)C(C)(C)C)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2695.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Lactoylphenylalanine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0007-9410000000-0cd8bc043bded37b3028	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Lactoylphenylalanine GC-MS (2 TMS) - 70eV, Positive	splash10-00r6-8962000000-d40495ad1a3b7f904155	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Lactoylphenylalanine 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-Lactoylphenylalanine 10V, Positive-QTOF	splash10-00du-3690000000-fe5efaae7d2bebb9789f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Lactoylphenylalanine 20V, Positive-QTOF	splash10-00dl-4930000000-41557da015fa2684948e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Lactoylphenylalanine 40V, Positive-QTOF	splash10-0006-9400000000-058c16babbf885335478	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Lactoylphenylalanine 10V, Negative-QTOF	splash10-000i-1390000000-0316182060d4be2e1cc6	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Lactoylphenylalanine 20V, Negative-QTOF	splash10-022l-4930000000-892857fde979d5980752	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Lactoylphenylalanine 40V, Negative-QTOF	splash10-00di-9500000000-a13bb3961f97b3bfd4f0	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Lactoylphenylalanine 10V, Positive-QTOF	splash10-00y0-0930000000-3c841a42eb530533b34d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Lactoylphenylalanine 20V, Positive-QTOF	splash10-00di-1900000000-6f6baa05d00f1f797f8e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Lactoylphenylalanine 40V, Positive-QTOF	splash10-00di-5900000000-8e5673adb13e6b5047b6	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Lactoylphenylalanine 10V, Negative-QTOF	splash10-000i-4290000000-19943ccd0c8992a79bfe	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Lactoylphenylalanine 20V, Negative-QTOF	splash10-0006-9600000000-77641d15cd4aec9dc2db	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Lactoylphenylalanine 40V, Negative-QTOF	splash10-0f6x-9700000000-47c4e820924a31ceb6c5	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	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	Adult (>18 years old)	Not Specified	Normal	25964343	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	25964343	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Phenylketonuria	25964343	details

Associated Disorders and Diseases

Disease References

Phenylketonuria
Jansen RS, Addie R, Merkx R, Fish A, Mahakena S, Bleijerveld OB, Altelaar M, IJlst L, Wanders RJ, Borst P, van de Wetering K: N-lactoyl-amino acids are ubiquitous metabolites that originate from CNDP2-mediated reverse proteolysis of lactate and amino acids. Proc Natl Acad Sci U S A. 2015 May 26;112(21):6601-6. doi: 10.1073/pnas.1424638112. Epub 2015 May 11. [PubMed:25964343 ]

Associated OMIM IDs

261600 (Phenylketonuria)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11075454

PDB ID

Not Available

ChEBI ID

Not Available

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

Jansen RS, Addie R, Merkx R, Fish A, Mahakena S, Bleijerveld OB, Altelaar M, IJlst L, Wanders RJ, Borst P, van de Wetering K: N-lactoyl-amino acids are ubiquitous metabolites that originate from CNDP2-mediated reverse proteolysis of lactate and amino acids. Proc Natl Acad Sci U S A. 2015 May 26;112(21):6601-6. doi: 10.1073/pnas.1424638112. Epub 2015 May 11. [PubMed:25964343 ]

Showing metabocard for N-Lactoylphenylalanine (HMDB0062175)

MOL for HMDB0062175 (N-Lactoylphenylalanine)

3D MOL for HMDB0062175 (N-Lactoylphenylalanine)

3D SDF for HMDB0062175 (N-Lactoylphenylalanine)

3D-SDF for HMDB0062175 (N-Lactoylphenylalanine)

PDB for HMDB0062175 (N-Lactoylphenylalanine)

3D PDB for HMDB0062175 (N-Lactoylphenylalanine)

SMILES for HMDB0062175 (N-Lactoylphenylalanine)

INCHI for HMDB0062175 (N-Lactoylphenylalanine)

Structure for HMDB0062175 (N-Lactoylphenylalanine)

3D Structure for HMDB0062175 (N-Lactoylphenylalanine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra