MiMeDB: Showing metabocard for N-Acetyl-L-tyrosine (MMDBc0000375)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:36:24 UTC

Update Date

2022-08-31 06:02:47 UTC

Metabolite ID

MMDBc0000375

Metabolite Identification

Common Name

N-Acetyl-L-tyrosine

Description

N-Acetyl-L-tyrosine or N-Acetyltyrosine, belongs to the class of organic compounds known as N-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. N-Acetyltyrosine can also be classified as an alpha amino acid or a derivatized alpha amino acid. Technically, N-Acetyltyrosine is a biologically available N-terminal capped form of the proteinogenic alpha amino acid L-tyrosine. N-acetyl amino acids can be produced either via direct synthesis of specific N-acetyltransferases or via the proteolytic degradation of N-acetylated proteins by specific hydrolases. N-terminal acetylation of proteins is a widespread and highly conserved process in eukaryotes that is involved in protection and stability of proteins (PMID: 16465618 ). About 85% of all human proteins and 68% of all yeast proteins are acetylated at their N-terminus (PMID: 21750686 ). Several proteins from prokaryotes and archaea are also modified by N-terminal acetylation. The majority of eukaryotic N-terminal-acetylation reactions occur through N-acetyltransferase enzymes or NAT‚Äôs (PMID: 30054468 ). These enzymes consist of three main oligomeric complexes NatA, NatB, and NatC, which are composed of at least a unique catalytic subunit and one unique ribosomal anchor. The substrate specificities of different NAT enzymes are mainly determined by the identities of the first two N-terminal residues of the target protein. The human NatA complex co-translationally acetylates N-termini that bear a small amino acid (A, S, T, C, and occasionally V and G) (PMID: 30054468 ). NatA also exists in a monomeric state and can post-translationally acetylate acidic N-termini residues (D-, E-). NatB and NatC acetylate N-terminal methionine with further specificity determined by the identity of the second amino acid. N-acetylated amino acids, such as N-acetyltyrosine can be released by an N-acylpeptide hydrolase from peptides generated by proteolytic degradation (PMID: 16465618 ). In addition to the NAT enzymes and protein-based acetylation, N-acetylation of free tyrosine can also occur. Many N-acetylamino acids, including N-acetyltyrosine are classified as uremic toxins if present in high abundance in the serum or plasma (PMID: 26317986 ; PMID: 20613759 ). Uremic toxins are a diverse group of endogenously produced molecules that, if not properly cleared or eliminated by the kidneys, can cause kidney damage, cardiovascular disease and neurological deficits (PMID: 18287557 ). N-Acetyl-L-tyrosine, has also been associated with several inborn metabolic disorders including tyrosinemia I and aromatic l-amino acid decarboxylase deficiency. N-acetyltyrosine, is used in place of as a tyrosine precursor and administered as a source of nutritional support where oral nutrition is inadequate or cannot be tolerated (PMID: 14621123 ). N-acetyltyrosine has also been identified as an endogenous stress response factor. Under stress conditions, mitochondria release low levels of reactive oxygen species (ROS), which triggers a cytoprotective response, called "mitohormesis". N-acetyltyrosine has recently been identified as an intrinsic triggering factor of mitohormesis in stressed animals (PMID: 32118349 ). Interventions and small molecules, which promote formation of reactive oxygen species (ROS), have been shown to increase stress resistance and lifespan of different model organisms. These phenotypes occur only in response to low concentrations of ROS, while higher concentrations of ROS exert opposing effects. In this regard, a stress-dependent increase in N-acetyltyrosine was recently found to occur in insect larvae that had endured high temperatures (i.e. thermal stress). N-acetyltyrosine treatment has also been demonstrated to induce thermotolerance in several tested insect species. N-acetyltyrosine has been identified in the serum of humans as well as mice, and its concentration in mice was shown to be increased by heat stress, with N-acetyltyrosine pretreatment lowering the concentrations of corticosterone and peroxidized lipids in heat stressed mice (PMID: 33617888 ).

Structure

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

HMDB0000866
     RDKit          3D
N-Acetyl-L-tyrosine
 29 29  0  0  0  0  0  0  0  0999 V2000
   -2.2467   -2.0182    1.3979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5967   -0.6881    1.3083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9197   -0.2500    2.2644 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7306    0.1076    0.1414 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1056    1.4059    0.0338 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0522    1.4197   -1.0762 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9877    0.4086   -0.7639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8298   -0.8710   -1.2260 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8163   -1.8130   -0.9249 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9264   -1.4819   -0.1835 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8971   -2.4496    0.1010 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0445   -0.1915    0.2586 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0880    0.7588   -0.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1057    2.4823   -0.1845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3534    2.2370   -0.2602 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7065    3.7945   -0.3131 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5031   -2.8320    1.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7821   -2.0517    2.3808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0089   -2.1419    0.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2917   -0.2609   -0.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5592    1.6086    0.9729 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3604    2.4357   -1.1389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5195    1.1303   -2.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0204   -1.1664   -1.8059 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6600   -2.8276   -1.3094 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7961   -3.0055    0.9557 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9084    0.0817    0.8400 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2132    1.7554    0.3385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0260    4.4232   -1.0376 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
  5 14  1  0
 14 15  2  0
 14 16  1  0
 13  7  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  5 21  1  1
  6 22  1  0
  6 23  1  0
  8 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 16 29  1  0
M  END


  Mrv1652305271900222D          

 16 16  0  0  1  0            999 V2000
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
 10 13  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000375

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H13NO4/c1-7(13)12-10(11(15)16)6-8-2-4-9(14)5-3-8/h2-5,10,14H,6H2,1H3,(H,12,13)(H,15,16)/t10-/m0/s1

> <INCHI_KEY>
CAHKINHBCWCHCF-JTQLQIEISA-N

> <FORMULA>
C11H13NO4

> <MOLECULAR_WEIGHT>
223.2252

> <EXACT_MASS>
223.084457909

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
22.253871389102308

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-acetamido-3-(4-hydroxyphenyl)propanoic acid

> <ALOGPS_LOGP>
1.03

> <JCHEM_LOGP>
0.5928963343333332

> <ALOGPS_LOGS>
-1.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.504642405543471

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6702334878899947

> <JCHEM_PKA_STRONGEST_BASIC>
-1.9831535533841467

> <JCHEM_POLAR_SURFACE_AREA>
86.63

> <JCHEM_REFRACTIVITY>
56.541000000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.51e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acetyl-L-tyrosine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000866
     RDKit          3D
N-Acetyl-L-tyrosine
 29 29  0  0  0  0  0  0  0  0999 V2000
   -2.2467   -2.0182    1.3979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5967   -0.6881    1.3083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9197   -0.2500    2.2644 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7306    0.1076    0.1414 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1056    1.4059    0.0338 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0522    1.4197   -1.0762 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9877    0.4086   -0.7639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8298   -0.8710   -1.2260 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8163   -1.8130   -0.9249 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9264   -1.4819   -0.1835 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8971   -2.4496    0.1010 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0445   -0.1915    0.2586 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0880    0.7588   -0.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1057    2.4823   -0.1845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3534    2.2370   -0.2602 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7065    3.7945   -0.3131 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5031   -2.8320    1.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7821   -2.0517    2.3808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0089   -2.1419    0.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2917   -0.2609   -0.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5592    1.6086    0.9729 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3604    2.4357   -1.1389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5195    1.1303   -2.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0204   -1.1664   -1.8059 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6600   -2.8276   -1.3094 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7961   -3.0055    0.9557 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9084    0.0817    0.8400 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2132    1.7554    0.3385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0260    4.4232   -1.0376 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
  5 14  1  0
 14 15  2  0
 14 16  1  0
 13  7  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  5 21  1  1
  6 22  1  0
  6 23  1  0
  8 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 16 29  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -6.160   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       2.667  -4.620   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002  -1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.336   0.770   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.668  -3.850   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       5.335  -6.160   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
CONECT   13   10                                                            
CONECT   14    5   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0000866
HETATM    1  C1  UNL     1      -2.247  -2.018   1.398  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.597  -0.688   1.308  1.00  0.00           C  
HETATM    3  O1  UNL     1      -0.920  -0.250   2.264  1.00  0.00           O  
HETATM    4  N1  UNL     1      -1.731   0.108   0.141  1.00  0.00           N  
HETATM    5  C3  UNL     1      -1.106   1.406   0.034  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.052   1.420  -1.076  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.988   0.409  -0.764  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.830  -0.871  -1.226  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.816  -1.813  -0.925  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.926  -1.482  -0.183  1.00  0.00           C  
HETATM   11  O2  UNL     1       3.897  -2.450   0.101  1.00  0.00           O  
HETATM   12  C9  UNL     1       3.045  -0.191   0.259  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.088   0.759  -0.023  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.106   2.482  -0.185  1.00  0.00           C  
HETATM   15  O3  UNL     1      -3.353   2.237  -0.260  1.00  0.00           O  
HETATM   16  O4  UNL     1      -1.707   3.795  -0.313  1.00  0.00           O  
HETATM   17  H1  UNL     1      -1.503  -2.832   1.355  1.00  0.00           H  
HETATM   18  H2  UNL     1      -2.782  -2.052   2.381  1.00  0.00           H  
HETATM   19  H3  UNL     1      -3.009  -2.142   0.597  1.00  0.00           H  
HETATM   20  H4  UNL     1      -2.292  -0.261  -0.645  1.00  0.00           H  
HETATM   21  H5  UNL     1      -0.559   1.609   0.973  1.00  0.00           H  
HETATM   22  H6  UNL     1       0.360   2.436  -1.139  1.00  0.00           H  
HETATM   23  H7  UNL     1      -0.519   1.130  -2.054  1.00  0.00           H  
HETATM   24  H8  UNL     1      -0.020  -1.166  -1.806  1.00  0.00           H  
HETATM   25  H9  UNL     1       1.660  -2.828  -1.309  1.00  0.00           H  
HETATM   26  H10 UNL     1       3.796  -3.006   0.956  1.00  0.00           H  
HETATM   27  H11 UNL     1       3.908   0.082   0.840  1.00  0.00           H  
HETATM   28  H12 UNL     1       2.213   1.755   0.338  1.00  0.00           H  
HETATM   29  H13 UNL     1      -2.026   4.423  -1.038  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    3    4
CONECT    4    5   20
CONECT    5    6   14   21
CONECT    6    7   22   23
CONECT    7    8    8   13
CONECT    8    9   24
CONECT    9   10   10   25
CONECT   10   11   12
CONECT   11   26
CONECT   12   13   13   27
CONECT   13   28
CONECT   14   15   15   16
CONECT   16   29
END

HMDB0000866
     RDKit          3D
N-Acetyl-L-tyrosine
 29 29  0  0  0  0  0  0  0  0999 V2000
   -2.2467   -2.0182    1.3979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5967   -0.6881    1.3083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9197   -0.2500    2.2644 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7306    0.1076    0.1414 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1056    1.4059    0.0338 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0522    1.4197   -1.0762 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9877    0.4086   -0.7639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8298   -0.8710   -1.2260 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8163   -1.8130   -0.9249 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9264   -1.4819   -0.1835 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8971   -2.4496    0.1010 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0445   -0.1915    0.2586 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0880    0.7588   -0.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1057    2.4823   -0.1845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3534    2.2370   -0.2602 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7065    3.7945   -0.3131 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5031   -2.8320    1.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7821   -2.0517    2.3808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0089   -2.1419    0.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2917   -0.2609   -0.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5592    1.6086    0.9729 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3604    2.4357   -1.1389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5195    1.1303   -2.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0204   -1.1664   -1.8059 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6600   -2.8276   -1.3094 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7961   -3.0055    0.9557 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9084    0.0817    0.8400 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2132    1.7554    0.3385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0260    4.4232   -1.0376 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
  5 14  1  0
 14 15  2  0
 14 16  1  0
 13  7  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  5 21  1  1
  6 22  1  0
  6 23  1  0
  8 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 16 29  1  0
M  END

Synonyms

Value	Source
N-Acetyl-4-hydroxyphenylalanine	ChEBI
N-Acetyltyrosine	ChEBI
(2S)-2-Acetylamino-3-(4-hydroxyphenyl)propanoate	HMDB
(2S)-2-Acetylamino-3-(4-hydroxyphenyl)propanoic acid	HMDB
L-N-Acetyl-tyrosine	HMDB
L-N-Acetyltyrosine	HMDB
N-Acetyl-tyrosine	HMDB
N-Acetyltyrosine, (DL)-isomer	HMDB
Acetyl-L-tyrosine	HMDB
N-Acetyltyrosine, (D)-isomer	HMDB

Molecular Formula

C₁₁H₁₃NO₄

Average Mass

223.2252

Monoisotopic Mass

223.084457909

IUPAC Name

(2S)-2-acetamido-3-(4-hydroxyphenyl)propanoic acid

Traditional Name

acetyl-L-tyrosine

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C11H13NO4/c1-7(13)12-10(11(15)16)6-8-2-4-9(14)5-3-8/h2-5,10,14H,6H2,1H3,(H,12,13)(H,15,16)/t10-/m0/s1

InChI Key

CAHKINHBCWCHCF-JTQLQIEISA-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
N-acyl-alpha amino acid or derivatives
N-acyl-l-alpha-amino acid
3-phenylpropanoic-acid
Amphetamine or derivatives
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Acetamide
Carboxamide group
Secondary carboxylic acid amide
Monocarboxylic acid or derivatives
Carboxylic acid
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

L-tyrosine derivative (CHEBI:21563 )
N-acetyl-L-amino acid (CHEBI:21563 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	2.51 g/L	ALOGPS
logP	1.03	ALOGPS
logP	0.59	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	3.67	ChemAxon
pKa (Strongest Basic)	-2	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	4	ChemAxon
Refractivity	56.54 m³·mol⁻¹	ChemAxon
Polarizability	22.25 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

Spectra

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Evidence Type	Host and Biospecimen	Data Source	Reference
Aromatic L-amino acid decarboxylase deficiency	Association	Human Urine	HMDB	16288991
Preterm birth	Association	Human Blood	HMDB	7815670
Tyrosinemia I	Association	Human Urine	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)
Tyrosinemia I	Association	Human Urine	HMDB	Physician's Guide to the Laboratory Diagnosis of Metabolic Diseases. 2nd ed. Berlin, Germany, Springer, 2003
Tyrosinemia I	Association	Human Urine	HMDB	Physician's Guide to the Laboratory Diagnosis of Metabolic Diseases. 2nd ed. Berlin, Germany, Springer, 2003

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1		Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Firmicutes	4	Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified								HMDB
Human	Detected and Quantified	10	2			Infant (0-1 year old)	Male	Aromatic L-amino acid decarboxylase deficiency	HMDB	16288991
Human	Detected and Quantified	331.0	74.0			Newborn (0-30 days old)	Both	Preterm birth	HMDB	7815670
Human	Detected and Quantified	1.00		0.00	2.00	Adult (>18 years old)	Both	Tyrosinemia I	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)
Human	Detected and Quantified	1.6		0	6.4	Infant (0-1 year old)	Both	Tyrosinemia I	HMDB	Physician's Guide to the Laboratory Diagnosis of Metabolic Diseases. 2nd ed. Berlin, Germany, Springer, 2003
Human	Detected and Quantified	75		0	781	Newborn (0-30 days old)	Both	Tyrosinemia I	HMDB	Physician's Guide to the Laboratory Diagnosis of Metabolic Diseases. 2nd ed. Berlin, Germany, Springer, 2003
Human	Detected and Quantified	<10				Children (1 - 18 years old)	Both	Normal	HMDB	BC Children's Hospital Biochemical Genetics Lab
Human	Detected and Quantified	0				Adult (>18 years old)	Both	Normal	HMDB	Physician's Guide to the Laboratory Diagnosis of Metabolic Diseases. 2nd ed. Berlin, Germany, Springer, 2003
Human	Detected and Quantified	1.600		0	6.400	Infant (0-1 year old)	Both	Normal	HMDB	Physician's Guide to the Laboratory Diagnosis of Metabolic Diseases. 2nd ed. Berlin, Germany, Springer, 2003
Human Urine	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	21389975
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0000866

DrugBank ID

DB11102

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022288

KNApSAcK ID

Not Available

Chemspider ID

61606

KEGG Compound ID

C01657

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

N-Acetyl-L-tyrosine

METLIN ID

Not Available

PubChem Compound

68310

PDB ID

Not Available

ChEBI ID

21563

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Rao NR, Bhat PG, Pattabiraman TN: Estimation of serum alpha 2-macroglobulin based on the esterolytic activity of bound alpha-chymotrypsin. Biochem Med. 1984 Dec;32(3):357-63. doi: 10.1016/0006-2944(84)90042-5. [PubMed:6083782 ]
Druml W, Hubl W, Roth E, Lochs H: Utilization of tyrosine-containing dipeptides and N-acetyl-tyrosine in hepatic failure. Hepatology. 1995 Apr;21(4):923-8. [PubMed:7705801 ]
Van Goudoever JB, Sulkers EJ, Timmerman M, Huijmans JG, Langer K, Carnielli VP, Sauer PJ: Amino acid solutions for premature neonates during the first week of life: the role of N-acetyl-L-cysteine and N-acetyl-L-tyrosine. JPEN J Parenter Enteral Nutr. 1994 Sep-Oct;18(5):404-8. doi: 10.1177/0148607194018005404. [PubMed:7815670 ]
Dietze EC, Grillo MP, Kalhorn T, Nieslanik BS, Jochheim CM, Atkins WM: Thiol ester hydrolysis catalyzed by glutathione S-transferase A1-1. Biochemistry. 1998 Oct 20;37(42):14948-57. doi: 10.1021/bi981284r. [PubMed:9778372 ]
Fu S, Wang H, Davies M, Dean R: Reactions of hypochlorous acid with tyrosine and peptidyl-tyrosyl residues give dichlorinated and aldehydic products in addition to 3-chlorotyrosine. J Biol Chem. 2000 Apr 14;275(15):10851-8. doi: 10.1074/jbc.275.15.10851. [PubMed:10753880 ]
Drabik G, Naskalski JW: Chlorination of N-acetyltyrosine with HOCl, chloramines, and myeloperoxidase-hydrogen peroxide-chloride system. Acta Biochim Pol. 2001;48(1):271-5. [PubMed:11440179 ]
Hoffer LJ, Sher K, Saboohi F, Bernier P, MacNamara EM, Rinzler D: N-acetyl-L-tyrosine as a tyrosine source in adult parenteral nutrition. JPEN J Parenter Enteral Nutr. 2003 Nov-Dec;27(6):419-22. doi: 10.1177/0148607103027006419. [PubMed:14621123 ]
Sass JO, Mohr V, Olbrich H, Engelke U, Horvath J, Fliegauf M, Loges NT, Schweitzer-Krantz S, Moebus R, Weiler P, Kispert A, Superti-Furga A, Wevers RA, Omran H: Mutations in ACY1, the gene encoding aminoacylase 1, cause a novel inborn error of metabolism. Am J Hum Genet. 2006 Mar;78(3):401-9. doi: 10.1086/500563. Epub 2006 Jan 18. [PubMed:16465618 ]
Vanholder R, Baurmeister U, Brunet P, Cohen G, Glorieux G, Jankowski J: A bench to bedside view of uremic toxins. J Am Soc Nephrol. 2008 May;19(5):863-70. doi: 10.1681/ASN.2007121377. Epub 2008 Feb 20. [PubMed:18287557 ]
Toyohara T, Akiyama Y, Suzuki T, Takeuchi Y, Mishima E, Tanemoto M, Momose A, Toki N, Sato H, Nakayama M, Hozawa A, Tsuji I, Ito S, Soga T, Abe T: Metabolomic profiling of uremic solutes in CKD patients. Hypertens Res. 2010 Sep;33(9):944-52. doi: 10.1038/hr.2010.113. Epub 2010 Jul 8. [PubMed:20613759 ]
Van Damme P, Hole K, Pimenta-Marques A, Helsens K, Vandekerckhove J, Martinho RG, Gevaert K, Arnesen T: NatF contributes to an evolutionary shift in protein N-terminal acetylation and is important for normal chromosome segregation. PLoS Genet. 2011 Jul;7(7):e1002169. doi: 10.1371/journal.pgen.1002169. Epub 2011 Jul 7. [PubMed:21750686 ]
Tanaka H, Sirich TL, Plummer NS, Weaver DS, Meyer TW: An Enlarged Profile of Uremic Solutes. PLoS One. 2015 Aug 28;10(8):e0135657. doi: 10.1371/journal.pone.0135657. eCollection 2015. [PubMed:26317986 ]
Ree R, Varland S, Arnesen T: Spotlight on protein N-terminal acetylation. Exp Mol Med. 2018 Jul 27;50(7):1-13. doi: 10.1038/s12276-018-0116-z. [PubMed:30054468 ]
Matsumura T, Uryu O, Matsuhisa F, Tajiri K, Matsumoto H, Hayakawa Y: N-acetyl-l-tyrosine is an intrinsic triggering factor of mitohormesis in stressed animals. EMBO Rep. 2020 May 6;21(5):e49211. doi: 10.15252/embr.201949211. Epub 2020 Mar 2. [PubMed:32118349 ]
Hayakawa Y: N-acetyltyrosine-induced redox signaling in hormesis. Biochim Biophys Acta Mol Cell Res. 2021 May;1868(6):118990. doi: 10.1016/j.bbamcr.2021.118990. Epub 2021 Feb 20. [PubMed:33617888 ]

Showing metabocard for N-Acetyl-L-tyrosine (MMDBc0000375)

MOL for #<Metabolite:0x00007f1219129e90>

3D MOL for #<Metabolite:0x00007f1219129e90>

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3D Structure for #<Metabolite:0x00007f1219129e90>