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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-10-13 04:31:28 UTC

HMDB ID

HMDB0000866

Secondary Accession Numbers

HMDB00866

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>
HMDB0000866

> <DATABASE_NAME>
hmdb

> <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

View in JSmol View NMR Assignments View Stereo Labels

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

Chemical Formula

C₁₁H₁₃NO₄

Average Molecular Weight

223.2252

Monoisotopic Molecular Weight

223.084457909

IUPAC Name

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

Traditional Name

acetyl-L-tyrosine

CAS Registry Number

537-55-3

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 )

Ontology

Physiological effect

Health effect

Nerve damage (PMID: 31434538)
Liver damage (PMID: 31434538)
Preterm birth (HMDB: HMDB0000866)
Aromatic l-amino acid decarboxylase deficiency (HMDB: HMDB0000866)
Tyrosinemia i (HMDB: HMDB0000866)

Urine (PMID: 16288991)
Feces (PMID: 27275383)

Non-excretory biofluid

Blood (PMID: 7815670)

Cellular substructure

Cytoplasm (HMDB: HMDB0000866)

Cytoplasm (HMDB: HMDB0000866)

Source

Endogenous

Endogenous (HMDB: HMDB0000866)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0000866)

Biomarker

Aromatic L-amino acid decarboxylase deficiency (MarkerDB: MDB00000270)
Tyrosinemia I (MarkerDB: MDB00000270)

Biological role

Waste product (PMID: 35448883)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	149 - 152 °C	Not Available
Boiling Point	530.00 to 533.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	297 mg/mL	Not Available
LogP	1.320	The Good Scents Company Information System

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	149.442	30932474
[M-H]-	Not Available	149.442	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000037

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	153.567	31661259
DarkChem	[M-H]-	149.593	31661259
AllCCS	[M+H]+	150.17	32859911
AllCCS	[M-H]-	149.818	32859911
DeepCCS	[M+H]+	150.047	30932474
DeepCCS	[M-H]-	147.651	30932474
DeepCCS	[M-2H]-	180.691	30932474
DeepCCS	[M+Na]+	156.015	30932474
AllCCS	[M+H]+	150.2	32859911
AllCCS	[M+H-H2O]+	146.4	32859911
AllCCS	[M+NH4]+	153.7	32859911
AllCCS	[M+Na]+	154.7	32859911
AllCCS	[M-H]-	149.8	32859911
AllCCS	[M+Na-2H]-	150.2	32859911
AllCCS	[M+HCOO]-	150.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Acetyl-L-tyrosine	CC(=O)N[C@@H](CC1=CC=C(O)C=C1)C(O)=O	3604.7	Standard polar	33892256
N-Acetyl-L-tyrosine	CC(=O)N[C@@H](CC1=CC=C(O)C=C1)C(O)=O	2108.4	Standard non polar	33892256
N-Acetyl-L-tyrosine	CC(=O)N[C@@H](CC1=CC=C(O)C=C1)C(O)=O	2187.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Acetyl-L-tyrosine,1TMS,isomer #1	CC(=O)N[C@@H](CC1=CC=C(O[Si](C)(C)C)C=C1)C(=O)O	2105.8	Semi standard non polar	33892256
N-Acetyl-L-tyrosine,1TMS,isomer #2	CC(=O)N[C@@H](CC1=CC=C(O)C=C1)C(=O)O[Si](C)(C)C	2087.0	Semi standard non polar	33892256
N-Acetyl-L-tyrosine,1TMS,isomer #3	CC(=O)N([C@@H](CC1=CC=C(O)C=C1)C(=O)O)[Si](C)(C)C	2091.8	Semi standard non polar	33892256
N-Acetyl-L-tyrosine,2TMS,isomer #1	CC(=O)N[C@@H](CC1=CC=C(O[Si](C)(C)C)C=C1)C(=O)O[Si](C)(C)C	2110.9	Semi standard non polar	33892256
N-Acetyl-L-tyrosine,2TMS,isomer #2	CC(=O)N([C@@H](CC1=CC=C(O[Si](C)(C)C)C=C1)C(=O)O)[Si](C)(C)C	2079.7	Semi standard non polar	33892256
N-Acetyl-L-tyrosine,2TMS,isomer #3	CC(=O)N([C@@H](CC1=CC=C(O)C=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2015.4	Semi standard non polar	33892256
N-Acetyl-L-tyrosine,3TMS,isomer #1	CC(=O)N([C@@H](CC1=CC=C(O[Si](C)(C)C)C=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2102.5	Semi standard non polar	33892256
N-Acetyl-L-tyrosine,3TMS,isomer #1	CC(=O)N([C@@H](CC1=CC=C(O[Si](C)(C)C)C=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2132.9	Standard non polar	33892256
N-Acetyl-L-tyrosine,3TMS,isomer #1	CC(=O)N([C@@H](CC1=CC=C(O[Si](C)(C)C)C=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2295.4	Standard polar	33892256
N-Acetyl-L-tyrosine,1TBDMS,isomer #1	CC(=O)N[C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O	2358.3	Semi standard non polar	33892256
N-Acetyl-L-tyrosine,1TBDMS,isomer #2	CC(=O)N[C@@H](CC1=CC=C(O)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	2323.7	Semi standard non polar	33892256
N-Acetyl-L-tyrosine,1TBDMS,isomer #3	CC(=O)N([C@@H](CC1=CC=C(O)C=C1)C(=O)O)[Si](C)(C)C(C)(C)C	2358.3	Semi standard non polar	33892256
N-Acetyl-L-tyrosine,2TBDMS,isomer #1	CC(=O)N[C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	2605.1	Semi standard non polar	33892256
N-Acetyl-L-tyrosine,2TBDMS,isomer #2	CC(=O)N([C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O)[Si](C)(C)C(C)(C)C	2627.8	Semi standard non polar	33892256
N-Acetyl-L-tyrosine,2TBDMS,isomer #3	CC(=O)N([C@@H](CC1=CC=C(O)C=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2532.2	Semi standard non polar	33892256
N-Acetyl-L-tyrosine,3TBDMS,isomer #1	CC(=O)N([C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2815.7	Semi standard non polar	33892256
N-Acetyl-L-tyrosine,3TBDMS,isomer #1	CC(=O)N([C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2762.8	Standard non polar	33892256
N-Acetyl-L-tyrosine,3TBDMS,isomer #1	CC(=O)N([C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2658.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - N-Acetyl-L-tyrosine GC-MS (3 TMS)	splash10-02t9-1790000000-9484167b29dc57768b67	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Acetyl-L-tyrosine GC-MS (2 TMS)	splash10-004i-1921000000-91d4d68bb345a8a8a747	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Acetyl-L-tyrosine GC-MS (Non-derivatized)	splash10-02t9-1790000000-9484167b29dc57768b67	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Acetyl-L-tyrosine GC-MS (Non-derivatized)	splash10-004i-1921000000-91d4d68bb345a8a8a747	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-L-tyrosine GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-9810000000-1b2e358b53063de15d83	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-L-tyrosine GC-MS (2 TMS) - 70eV, Positive	splash10-0uml-9574000000-9aeba0b3dc5069db4126	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-L-tyrosine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-L-tyrosine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-L-tyrosine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-L-tyrosine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-L-tyrosine GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-L-tyrosine GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-L-tyrosine GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-L-tyrosine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-L-tyrosine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-L-tyrosine GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-L-tyrosine GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-L-tyrosine GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-L-tyrosine GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-tyrosine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0059-0900000000-1a298550f3c63022066c	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-tyrosine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-000i-1900000000-489314daf5773f9fa91e	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-tyrosine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0006-9300000000-3a02844e3f23883a2818	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-tyrosine 20V, Positive-QTOF	splash10-000i-1900000000-c90d231f8d22d9f26ddc	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-tyrosine 10V, Positive-QTOF	splash10-000i-0900000000-ccea38bdb004d86be263	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-tyrosine 10V, Positive-QTOF	splash10-000l-2900000000-318d79dc731f181122e3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-tyrosine 30V, Positive-QTOF	splash10-0006-9500000000-5884fdc7247228527651	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-tyrosine 10V, Positive-QTOF	splash10-00kr-5900000000-9612848117c7c187b999	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-tyrosine 0V, Positive-QTOF	splash10-0072-8940000000-b6f543bf9466f5d0a83f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-tyrosine 30V, Positive-QTOF	splash10-0006-9300000000-b45eebbf975e26ab166b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-tyrosine 0V, Positive-QTOF	splash10-00dr-1940000000-33b69b7977f9d9af1050	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-tyrosine 30V, Negative-QTOF	splash10-0a4i-9600000000-a990ee67ce972fd9112e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-tyrosine 20V, Negative-QTOF	splash10-0a59-6900000000-faa99ebaf3b7d2305237	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-tyrosine 40V, Negative-QTOF	splash10-0a4l-9300000000-0995fa9131d49c7c9568	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-tyrosine 30V, Positive-QTOF	splash10-00ko-6900000000-2dc778488fd30e78d38a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-tyrosine 10V, Negative-QTOF	splash10-0089-2940000000-9ba200b376edff696810	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-tyrosine 40V, Positive-QTOF	splash10-0006-9100000000-28b05f6697d1910b23f9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-tyrosine 40V, Positive-QTOF	splash10-0006-9200000000-9bcdc6b13b9c4ec88928	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-tyrosine 20V, Positive-QTOF	splash10-000i-0900000000-7301664a6d8d33145cdf	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-L-tyrosine 10V, Positive-QTOF	splash10-05gi-0960000000-521b33c688de6d5af3c6	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-L-tyrosine 20V, Positive-QTOF	splash10-0540-0910000000-11b06e8237181862ad09	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-L-tyrosine 40V, Positive-QTOF	splash10-0a4i-4900000000-0ed4f6b83b0e699609da	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-L-tyrosine 10V, Negative-QTOF	splash10-00di-1690000000-1c3495d31ad780bf247c	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-L-tyrosine 20V, Negative-QTOF	splash10-05ir-4920000000-04fd94657e89950888ef	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-L-tyrosine 40V, Negative-QTOF	splash10-052f-9400000000-a5cd6e5756fee449095e	2017-07-26	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Urine	Detected and Quantified	0 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Physician's Guide...	details
Urine	Detected and Quantified	1.600 (0-6.400) umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	Physician's Guide...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21389975	details
Urine	Detected and Quantified	<10 umol/mmol creatinine	Children (1 - 18 years old)	Both	Normal	BC Children's Hos...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	331.0 +/- 74.0 uM	Newborn (0-30 days old)	Both	Preterm birth	7815670	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected and Quantified	1.6 (0-6.4) umol/mmol creatinine	Infant (0-1 year old)	Both	Tyrosinemia I	Physician's Guide...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal adenoma	27510537	details
Urine	Detected and Quantified	1.00 (0.00-2.00) umol/mmol creatinine	Adult (>18 years old)	Both	Tyrosinemia I	MetaGene: Metabol...	details
Urine	Detected and Quantified	10 +/- 2 umol/mmol creatinine	Infant (0-1 year old)	Male	Aromatic L-amino acid decarboxylase deficiency	16288991	details
Urine	Detected and Quantified	75 (0-781) umol/mmol creatinine	Newborn (0-30 days old)	Both	Tyrosinemia I	Physician's Guide...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Autosomal dominant polycystic kidney disease (ADPKD)	21389975	details

Associated Disorders and Diseases

Disease References

Preterm birth
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. [PubMed:7815670 ]
Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Aromatic L-amino acid decarboxylase deficiency
Abdenur JE, Abeling N, Specola N, Jorge L, Schenone AB, van Cruchten AC, Chamoles NA: Aromatic l-aminoacid decarboxylase deficiency: unusual neonatal presentation and additional findings in organic acid analysis. Mol Genet Metab. 2006 Jan;87(1):48-53. Epub 2005 Nov 9. [PubMed:16288991 ]
Tyrosinemia I
G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium. Blau N, Duran M, Blaskovics ME, Gibson KM (2003). Physician's Guide to the Laboratory Diagnosis of Metabolic Diseases. 2nd ed. Berlin, Germany, Springer, 2003. Springer.
Autosomal dominant polycystic kidney disease
Gronwald W, Klein MS, Zeltner R, Schulze BD, Reinhold SW, Deutschmann M, Immervoll AK, Boger CA, Banas B, Eckardt KU, Oefner PJ: Detection of autosomal dominant polycystic kidney disease by NMR spectroscopic fingerprinting of urine. Kidney Int. 2011 Jun;79(11):1244-53. doi: 10.1038/ki.2011.30. Epub 2011 Mar 9. [PubMed:21389975 ]

Associated OMIM IDs

114500 (Colorectal cancer)
608643 (Aromatic L-amino acid decarboxylase deficiency)
276700 (Tyrosinemia I)
601313 (Autosomal dominant polycystic kidney disease)

External Links

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

VMH ID

Not Available

MarkerDB ID

MDB00000270

Good Scents ID

rw1097521

References

Synthesis Reference

Liu, Aifu. Preparation of N-acetyl-L-tyrosine. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 5 pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

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. Epub 2006 Jan 18. [PubMed:16465618 ]
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. [PubMed:6083782 ]
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. [PubMed:14621123 ]
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. [PubMed:9778372 ]
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. [PubMed:7815670 ]
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 ]
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. [PubMed:10753880 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 (HMDB0000866)

MOL for HMDB0000866 (N-Acetyl-L-tyrosine)

3D MOL for HMDB0000866 (N-Acetyl-L-tyrosine)

3D SDF for HMDB0000866 (N-Acetyl-L-tyrosine)

3D-SDF for HMDB0000866 (N-Acetyl-L-tyrosine)

PDB for HMDB0000866 (N-Acetyl-L-tyrosine)

3D PDB for HMDB0000866 (N-Acetyl-L-tyrosine)

SMILES for HMDB0000866 (N-Acetyl-L-tyrosine)

INCHI for HMDB0000866 (N-Acetyl-L-tyrosine)

Structure for HMDB0000866 (N-Acetyl-L-tyrosine)

3D Structure for HMDB0000866 (N-Acetyl-L-tyrosine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra