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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 12:34:56 UTC

Update Date

2021-09-24 12:34:56 UTC

HMDB ID

HMDB0304809

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Pretyrosine

Description

Pretyrosine, also known as L-arogenate or L-arogenic acid, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. Pretyrosine has been detected, but not quantified in, milk (cow). This could make pretyrosine a potential biomarker for the consumption of these foods. Pretyrosine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Pretyrosine.

Structure

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

HMDB0304809
     RDKit          3D
Pretyrosine
 29 29  0  0  0  0  0  0  0  0999 V2000
    1.4690   -1.7514    0.2543 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7900   -0.5879   -0.5448 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1411    0.6474    0.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3642    0.5495    0.0523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8596    1.8530    0.6265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5338    1.8995    1.6868 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5569    3.0144   -0.0406 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8596   -0.5183    0.9127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9402   -1.2087    0.5727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6882   -0.9285   -0.6880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8672   -0.2310   -0.4203 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9146   -0.1760   -1.6763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8534    0.4978   -1.3332 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2578   -0.3909   -0.4836 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9917   -1.1638    0.1787 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8632    0.6558   -1.1583 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0373   -2.5700   -0.0594 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8296   -1.5409    1.2334 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4951   -0.7603   -1.6125 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5283    0.8258    1.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3838    1.4995   -0.6659 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2417    3.5940    0.2515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3633   -0.7628    1.8285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3309   -2.0078    1.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9832   -1.9252   -1.1156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6781   -0.7481   -0.6724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2893   -0.2199   -2.7181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3052    1.0431   -2.0892 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3592    1.4117   -0.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  4  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
  2 14  1  0
 14 15  2  0
 14 16  1  0
 13  4  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  6
  3 20  1  0
  3 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 16 29  1  0
M  END

  Mrv1652304032019082D          

 18 18  0  0  1  0            999 V2000
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1018    1.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9263    1.9947    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3635    1.2951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3272    1.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3136    2.7232    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1880    1.3239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9762    0.5667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4973    1.9947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7643    2.6656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5390    1.2663    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  6  1  1  0  0  0  0
  6  2  1  0  0  0  0
  7  5  1  0  0  0  0
  8  7  1  0  0  0  0
 10  3  1  0  0  0  0
 10  4  1  0  0  0  0
 10  5  1  0  0  0  0
 10  9  1  0  0  0  0
  7 11  1  1  0  0  0
 12  6  1  0  0  0  0
 13  8  2  0  0  0  0
 14  8  1  0  0  0  0
 15  9  2  0  0  0  0
 16  9  1  0  0  0  0
 17  6  1  0  0  0  0
  7 18  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0304809

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H13NO5/c11-7(8(13)14)5-10(9(15)16)3-1-6(12)2-4-10/h1-4,6-7,12H,5,11H2,(H,13,14)(H,15,16)/t6?,7-,10?/m0/s1

> <INCHI_KEY>
MIEILDYWGANZNH-DSQUFTABSA-N

> <FORMULA>
C10H13NO5

> <MOLECULAR_WEIGHT>
227.216

> <EXACT_MASS>
227.079372523

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
21.262431709882854

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-[(2S)-2-amino-2-carboxyethyl]-4-hydroxycyclohexa-2,5-diene-1-carboxylic acid

> <ALOGPS_LOGP>
-3.18

> <JCHEM_LOGP>
-3.087520089417646

> <ALOGPS_LOGS>
-1.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.0724243272322935

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.9577070914356351

> <JCHEM_PKA_STRONGEST_BASIC>
9.501665478022854

> <JCHEM_POLAR_SURFACE_AREA>
120.85000000000001

> <JCHEM_REFRACTIVITY>
55.9587

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.88e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
arogenate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0304809
     RDKit          3D
Pretyrosine
 29 29  0  0  0  0  0  0  0  0999 V2000
    1.4690   -1.7514    0.2543 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7900   -0.5879   -0.5448 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1411    0.6474    0.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3642    0.5495    0.0523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8596    1.8530    0.6265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5338    1.8995    1.6868 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5569    3.0144   -0.0406 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8596   -0.5183    0.9127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9402   -1.2087    0.5727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6882   -0.9285   -0.6880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8672   -0.2310   -0.4203 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9146   -0.1760   -1.6763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8534    0.4978   -1.3332 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2578   -0.3909   -0.4836 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9917   -1.1638    0.1787 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8632    0.6558   -1.1583 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0373   -2.5700   -0.0594 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8296   -1.5409    1.2334 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4951   -0.7603   -1.6125 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5283    0.8258    1.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3838    1.4995   -0.6659 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2417    3.5940    0.2515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3633   -0.7628    1.8285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3309   -2.0078    1.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9832   -1.9252   -1.1156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6781   -0.7481   -0.6724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2893   -0.2199   -2.7181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3052    1.0431   -2.0892 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3592    1.4117   -0.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  4  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
  2 14  1  0
 14 15  2  0
 14 16  1  0
 13  4  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  6
  3 20  1  0
  3 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 16 29  1  0
M  END

HEADER    PROTEIN                                 03-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-APR-20         0                                  
HETATM    1  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.057   3.670   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.596   3.723   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.412   2.418   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.611   3.670   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       4.319   5.083   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       5.951   2.471   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       3.689   1.058   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -0.928   3.723   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       1.427   4.976   0.000  0.00  0.00           O+0
HETATM   17  H   UNK     0       0.000  -1.540   0.000  0.00  0.00           H+0
HETATM   18  H   UNK     0       2.873   2.364   0.000  0.00  0.00           H+0
CONECT    1    3    6                                                       
CONECT    2    4    6                                                       
CONECT    3    1   10                                                       
CONECT    4    2   10                                                       
CONECT    5    7   10                                                       
CONECT    6    1    2   12   17                                             
CONECT    7    5    8   11   18                                             
CONECT    8    7   13   14                                                  
CONECT    9   10   15   16                                                  
CONECT   10    3    4    5    9                                             
CONECT   11    7                                                            
CONECT   12    6                                                            
CONECT   13    8                                                            
CONECT   14    8                                                            
CONECT   15    9                                                            
CONECT   16    9                                                            
CONECT   17    6                                                            
CONECT   18    7                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0304809
HETATM    1  N1  UNL     1       1.469  -1.751   0.254  1.00  0.00           N  
HETATM    2  C1  UNL     1       1.790  -0.588  -0.545  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.141   0.647   0.009  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.364   0.549   0.052  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.860   1.853   0.626  1.00  0.00           C  
HETATM    6  O1  UNL     1      -1.534   1.900   1.687  1.00  0.00           O  
HETATM    7  O2  UNL     1      -0.557   3.014  -0.041  1.00  0.00           O  
HETATM    8  C5  UNL     1      -0.860  -0.518   0.913  1.00  0.00           C  
HETATM    9  C6  UNL     1      -1.940  -1.209   0.573  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.688  -0.928  -0.688  1.00  0.00           C  
HETATM   11  O3  UNL     1      -3.867  -0.231  -0.420  1.00  0.00           O  
HETATM   12  C8  UNL     1      -1.915  -0.176  -1.676  1.00  0.00           C  
HETATM   13  C9  UNL     1      -0.853   0.498  -1.333  1.00  0.00           C  
HETATM   14  C10 UNL     1       3.258  -0.391  -0.484  1.00  0.00           C  
HETATM   15  O4  UNL     1       3.992  -1.164   0.179  1.00  0.00           O  
HETATM   16  O5  UNL     1       3.863   0.656  -1.158  1.00  0.00           O  
HETATM   17  H1  UNL     1       2.037  -2.570  -0.059  1.00  0.00           H  
HETATM   18  H2  UNL     1       1.830  -1.541   1.233  1.00  0.00           H  
HETATM   19  H3  UNL     1       1.495  -0.760  -1.613  1.00  0.00           H  
HETATM   20  H4  UNL     1       1.528   0.826   1.021  1.00  0.00           H  
HETATM   21  H5  UNL     1       1.384   1.500  -0.666  1.00  0.00           H  
HETATM   22  H6  UNL     1       0.242   3.594   0.252  1.00  0.00           H  
HETATM   23  H7  UNL     1      -0.363  -0.763   1.828  1.00  0.00           H  
HETATM   24  H8  UNL     1      -2.331  -2.008   1.194  1.00  0.00           H  
HETATM   25  H9  UNL     1      -2.983  -1.925  -1.116  1.00  0.00           H  
HETATM   26  H10 UNL     1      -4.678  -0.748  -0.672  1.00  0.00           H  
HETATM   27  H11 UNL     1      -2.289  -0.220  -2.718  1.00  0.00           H  
HETATM   28  H12 UNL     1      -0.305   1.043  -2.089  1.00  0.00           H  
HETATM   29  H13 UNL     1       4.359   1.412  -0.728  1.00  0.00           H  
CONECT    1    2   17   18
CONECT    2    3   14   19
CONECT    3    4   20   21
CONECT    4    5    8   13
CONECT    5    6    6    7
CONECT    7   22
CONECT    8    9    9   23
CONECT    9   10   24
CONECT   10   11   12   25
CONECT   11   26
CONECT   12   13   13   27
CONECT   13   28
CONECT   14   15   15   16
CONECT   16   29
END

HMDB0304809
     RDKit          3D
Pretyrosine
 29 29  0  0  0  0  0  0  0  0999 V2000
    1.4690   -1.7514    0.2543 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7900   -0.5879   -0.5448 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1411    0.6474    0.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3642    0.5495    0.0523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8596    1.8530    0.6265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5338    1.8995    1.6868 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5569    3.0144   -0.0406 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8596   -0.5183    0.9127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9402   -1.2087    0.5727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6882   -0.9285   -0.6880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8672   -0.2310   -0.4203 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9146   -0.1760   -1.6763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8534    0.4978   -1.3332 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2578   -0.3909   -0.4836 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9917   -1.1638    0.1787 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8632    0.6558   -1.1583 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0373   -2.5700   -0.0594 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8296   -1.5409    1.2334 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4951   -0.7603   -1.6125 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5283    0.8258    1.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3838    1.4995   -0.6659 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2417    3.5940    0.2515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3633   -0.7628    1.8285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3309   -2.0078    1.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9832   -1.9252   -1.1156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6781   -0.7481   -0.6724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2893   -0.2199   -2.7181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3052    1.0431   -2.0892 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3592    1.4117   -0.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  4  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
  2 14  1  0
 14 15  2  0
 14 16  1  0
 13  4  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  6
  3 20  1  0
  3 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 16 29  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
alpha-Amino-1-carboxy-4-hydroxy-2,5-cyclohexadiene-1-propanoic acid	ChEBI
L-Arogenate	ChEBI
L-Arogenic acid	Kegg
a-Amino-1-carboxy-4-hydroxy-2,5-cyclohexadiene-1-propanoate	Generator
a-Amino-1-carboxy-4-hydroxy-2,5-cyclohexadiene-1-propanoic acid	Generator
alpha-Amino-1-carboxy-4-hydroxy-2,5-cyclohexadiene-1-propanoate	Generator
Α-amino-1-carboxy-4-hydroxy-2,5-cyclohexadiene-1-propanoate	Generator
Α-amino-1-carboxy-4-hydroxy-2,5-cyclohexadiene-1-propanoic acid	Generator
Arogenate	HMDB
Pretyrosine	ChEBI

Chemical Formula

C₁₀H₁₃NO₅

Average Molecular Weight

227.216

Monoisotopic Molecular Weight

227.079372523

IUPAC Name

1-[(2S)-2-amino-2-carboxyethyl]-4-hydroxycyclohexa-2,5-diene-1-carboxylic acid

Traditional Name

arogenate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C10H13NO5/c11-7(8(13)14)5-10(9(15)16)3-1-6(12)2-4-10/h1-4,6-7,12H,5,11H2,(H,13,14)(H,15,16)/t6?,7-,10?/m0/s1

InChI Key

MIEILDYWGANZNH-DSQUFTABSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

L-alpha-amino acid
Dicarboxylic acid or derivatives
Secondary alcohol
Amino acid
Carboxylic acid
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organic nitrogen compound
Alcohol
Carbonyl group
Amine
Organic oxide
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

arogenic acid (CHEBI:17530 )

Ontology

Not Available

Exogenous (HMDB: HMDB0304809)

Food

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

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	-3.2	ALOGPS
logP	-3.1	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	1.96	ChemAxon
pKa (Strongest Basic)	9.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	120.85 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	55.96 m³·mol⁻¹	ChemAxon
Polarizability	21.26 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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
AllCCS	[M+H]+	151.009	32859911
AllCCS	[M+H-H2O]+	147.292	32859911
AllCCS	[M+Na]+	155.456	32859911
AllCCS	[M+NH4]+	154.463	32859911
AllCCS	[M-H]-	147.953	32859911
AllCCS	[M+Na-2H]-	148.297	32859911
AllCCS	[M+HCOO]-	148.772	32859911
DeepCCS	[M+H]+	151.527	30932474
DeepCCS	[M-H]-	149.132	30932474
DeepCCS	[M-2H]-	182.089	30932474
DeepCCS	[M+Na]+	157.563	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Pretyrosine,4TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1(C(=O)O[Si](C)(C)C)C=CC(O[Si](C)(C)C)C=C1)C(=O)O[Si](C)(C)C	2140.5	Semi standard non polar	33892256
Pretyrosine,4TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1(C(=O)O[Si](C)(C)C)C=CC(O[Si](C)(C)C)C=C1)C(=O)O[Si](C)(C)C	2185.7	Standard non polar	33892256
Pretyrosine,4TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1(C(=O)O[Si](C)(C)C)C=CC(O[Si](C)(C)C)C=C1)C(=O)O[Si](C)(C)C	2396.0	Standard polar	33892256
Pretyrosine,4TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](CC1(C(=O)O)C=CC(O[Si](C)(C)C)C=C1)N([Si](C)(C)C)[Si](C)(C)C	2312.9	Semi standard non polar	33892256
Pretyrosine,4TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](CC1(C(=O)O)C=CC(O[Si](C)(C)C)C=C1)N([Si](C)(C)C)[Si](C)(C)C	2279.6	Standard non polar	33892256
Pretyrosine,4TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](CC1(C(=O)O)C=CC(O[Si](C)(C)C)C=C1)N([Si](C)(C)C)[Si](C)(C)C	2716.1	Standard polar	33892256
Pretyrosine,4TMS,isomer #3	C[Si](C)(C)OC(=O)C1(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=CC(O[Si](C)(C)C)C=C1	2287.8	Semi standard non polar	33892256
Pretyrosine,4TMS,isomer #3	C[Si](C)(C)OC(=O)C1(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=CC(O[Si](C)(C)C)C=C1	2267.4	Standard non polar	33892256
Pretyrosine,4TMS,isomer #3	C[Si](C)(C)OC(=O)C1(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=CC(O[Si](C)(C)C)C=C1	2516.4	Standard polar	33892256
Pretyrosine,4TMS,isomer #4	C[Si](C)(C)OC(=O)[C@H](CC1(C(=O)O[Si](C)(C)C)C=CC(O)C=C1)N([Si](C)(C)C)[Si](C)(C)C	2277.4	Semi standard non polar	33892256
Pretyrosine,4TMS,isomer #4	C[Si](C)(C)OC(=O)[C@H](CC1(C(=O)O[Si](C)(C)C)C=CC(O)C=C1)N([Si](C)(C)C)[Si](C)(C)C	2211.8	Standard non polar	33892256
Pretyrosine,4TMS,isomer #4	C[Si](C)(C)OC(=O)[C@H](CC1(C(=O)O[Si](C)(C)C)C=CC(O)C=C1)N([Si](C)(C)C)[Si](C)(C)C	2776.4	Standard polar	33892256
Pretyrosine,5TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1(C(=O)O[Si](C)(C)C)C=CC(O[Si](C)(C)C)C=C1)N([Si](C)(C)C)[Si](C)(C)C	2295.4	Semi standard non polar	33892256
Pretyrosine,5TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1(C(=O)O[Si](C)(C)C)C=CC(O[Si](C)(C)C)C=C1)N([Si](C)(C)C)[Si](C)(C)C	2305.4	Standard non polar	33892256
Pretyrosine,5TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1(C(=O)O[Si](C)(C)C)C=CC(O[Si](C)(C)C)C=C1)N([Si](C)(C)C)[Si](C)(C)C	2335.8	Standard polar	33892256
Pretyrosine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1(C(=O)O[Si](C)(C)C(C)(C)C)C=CC(O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	3008.4	Semi standard non polar	33892256
Pretyrosine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1(C(=O)O[Si](C)(C)C(C)(C)C)C=CC(O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	2848.4	Standard non polar	33892256
Pretyrosine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1(C(=O)O[Si](C)(C)C(C)(C)C)C=CC(O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	2747.2	Standard polar	33892256
Pretyrosine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1(C(=O)O)C=CC(O[Si](C)(C)C(C)(C)C)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3260.1	Semi standard non polar	33892256
Pretyrosine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1(C(=O)O)C=CC(O[Si](C)(C)C(C)(C)C)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2966.0	Standard non polar	33892256
Pretyrosine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1(C(=O)O)C=CC(O[Si](C)(C)C(C)(C)C)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2975.3	Standard polar	33892256
Pretyrosine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C1(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=CC(O[Si](C)(C)C(C)(C)C)C=C1	3248.9	Semi standard non polar	33892256
Pretyrosine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C1(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=CC(O[Si](C)(C)C(C)(C)C)C=C1	2919.8	Standard non polar	33892256
Pretyrosine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C1(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=CC(O[Si](C)(C)C(C)(C)C)C=C1	2795.1	Standard polar	33892256
Pretyrosine,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1(C(=O)O[Si](C)(C)C(C)(C)C)C=CC(O)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3190.8	Semi standard non polar	33892256
Pretyrosine,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1(C(=O)O[Si](C)(C)C(C)(C)C)C=CC(O)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2913.4	Standard non polar	33892256
Pretyrosine,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1(C(=O)O[Si](C)(C)C(C)(C)C)C=CC(O)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3015.0	Standard polar	33892256
Pretyrosine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1(C(=O)O[Si](C)(C)C(C)(C)C)C=CC(O[Si](C)(C)C(C)(C)C)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3404.1	Semi standard non polar	33892256
Pretyrosine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1(C(=O)O[Si](C)(C)C(C)(C)C)C=CC(O[Si](C)(C)C(C)(C)C)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3126.9	Standard non polar	33892256
Pretyrosine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1(C(=O)O[Si](C)(C)C(C)(C)C)C=CC(O[Si](C)(C)C(C)(C)C)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2759.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Pretyrosine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2022-08-08	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 - Pretyrosine 10V, Positive-QTOF	splash10-03di-0950000000-782d5cfa738f90bf1526	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pretyrosine 20V, Positive-QTOF	splash10-03dr-0900000000-7bef5da41f16df9d557b	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pretyrosine 40V, Positive-QTOF	splash10-06ri-2900000000-776124826df3419e8de4	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pretyrosine 10V, Negative-QTOF	splash10-056r-0490000000-76f22ef81b7be13c221d	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pretyrosine 20V, Negative-QTOF	splash10-08gi-0930000000-3c123e79842b7a1d7f6b	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pretyrosine 40V, Negative-QTOF	splash10-00dr-8900000000-5ad707d2e6298afa8fb2	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pretyrosine 10V, Positive-QTOF	splash10-03di-0790000000-a5980aeb4d33d4e865ea	2021-10-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pretyrosine 20V, Positive-QTOF	splash10-000j-3900000000-9b39484ce8603a4f632f	2021-10-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pretyrosine 40V, Positive-QTOF	splash10-0a4i-5900000000-8533948c2db75eeed76d	2021-10-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pretyrosine 10V, Negative-QTOF	splash10-004u-7590000000-49b78f61c3dabe62db31	2021-10-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pretyrosine 20V, Negative-QTOF	splash10-0c2i-5980000000-6600e70309b0fe76fcc8	2021-10-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pretyrosine 40V, Negative-QTOF	splash10-00di-9700000000-49061b30153d2d401788	2021-10-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

439319

PDB ID

Not Available

ChEBI ID

17530

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

Not Available

Showing metabocard for Pretyrosine (HMDB0304809)

MOL for HMDB0304809 (Pretyrosine)

3D MOL for HMDB0304809 (Pretyrosine)

3D SDF for HMDB0304809 (Pretyrosine)

3D-SDF for HMDB0304809 (Pretyrosine)

PDB for HMDB0304809 (Pretyrosine)

3D PDB for HMDB0304809 (Pretyrosine)

SMILES for HMDB0304809 (Pretyrosine)

INCHI for HMDB0304809 (Pretyrosine)

Structure for HMDB0304809 (Pretyrosine)

3D Structure for HMDB0304809 (Pretyrosine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra