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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-05-30 20:55:53 UTC

HMDB ID

HMDB0000206

Secondary Accession Numbers

HMDB00206

Metabolite Identification

Common Name

N6-Acetyl-L-lysine

Description

N-epsilon-Acetyl-L-lysine also known as Nepsilon-Acetyllysine or N6-Acetyllysine, 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 one of its nitrogen atoms. N-epsilon-Acetyl-L-lysine can also be classified as an alpha amino acid or a derivatized alpha amino acid. Technically, N-epsilon-Acetyl-L-lysine is a biologically available sidechain, N-capped form of the proteinogenic alpha amino acid L-lysine. Unlike L-lysine, acetylated lysine derivatives such as N-epsilon-Acetyl-L-lysine are zwitterionic compounds. These are molecules that contains an equal number of positively- and negatively-charged functional groups. N-epsilon-Acetyl-L-lysine is found naturally in eukaryotes ranging from yeast to plants to humans. N-acetyl amino acids can be produced either via direct synthesis of specific N-acetyltransferases or via the proteolytic degradation of N-acetylated proteins (often histones) by specific hydrolases. N-epsilon-Acetyl-L-lysine can be biosynthesized from L-lysine and acetyl-CoA via the enzyme known as Lysine N-acetyltransferase. Post-translational lysine-acetylation is one of two major modifications of lysine residues in various proteins - either N-terminal or N-alpha acetylation or N6 (sidechain) acetylation. Side-chain acetylation of specific lysine residues in the N-terminal domains of core histones is a biochemical marker of active genes. Acetylation is now known to play a major role in eukaryotic transcription. Specifically, acetyltransferase enzymes that act on particular lysine side chains of histones and other proteins are intimately involved in transcriptional activation. By modifying chromatin proteins and transcription-related factors, these acetylases are believed to regulate the transcription of many genes. The best-characterized mechanism is acetylation, catalyzed by histone acetyltransferase (HAT) enzymes. HATs function enzymatically by transferring an acetyl group from acetyl-coenzyme A (acetyl-CoA) to the amino group of certain lysine side chains within a histone's basic N-terminal tail region. Within a histone octamer, these regions extend out from the associated globular domains, and in the context of a nucleosome, they are believed to bind the DNA through charge interactions (positively charged histone tails associated with negatively charged DNA) or mediate interactions between nucleosomes. Lysine acetylation, which neutralizes part of a tail region's positive charge, is postulated to weaken histone-DNA or nucleosome-nucleosome interactions and/or signal a conformational change, thereby destabilizing nucleosome structure or arrangement and giving other nuclear factors, such as the transcription complex, more access to a genetic locus. In agreement with this is the fact that acetylated chromatin has long been associated with states of transcriptional activation. Specific recognition of N6-acetyl-L-lysine is a conserved function of all bromodomains found in different proteins, recognized as an emerging intracellular signalling mechanism that plays critical roles in regulating gene transcription, cell-cycle progression, apoptosis, DNA repair, and cytoskeletal organization (PMID: 9169194 , 10827952 , 17340003 , 16247734 , 9478947 , 10839822 ). N-acetylated amino acids, such as N-epsilon-Acetyl-L-lysine can be released by an N-acylpeptide hydrolase from histones going through proteolytic degradation (PMID: 16465618 ). Many N-acetylamino acids 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 ).

Structure

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

HMDB0000206
     RDKit          3D
N6-Acetyl-L-lysine
 29 28  0  0  0  0  0  0  0  0999 V2000
    4.7961    0.5208    0.4283 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6959    0.1055   -0.4683 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9746   -0.5665   -1.4807 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3554    0.4511   -0.2026 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3241    0.0204   -1.1092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0497    0.4796   -0.6693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4169   -0.0499    0.6812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7868    0.4552    1.0409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8621    0.0327    0.0755 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1187    0.6102    0.5826 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0694   -1.4180    0.0062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1609   -1.9902    0.3464 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0798   -2.3085   -0.4430 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0750   -0.2966    1.1256 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6673    0.7693   -0.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5264    1.4585    0.9620 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1430    1.0234    0.6647 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3230   -1.0886   -1.1228 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5221    0.4801   -2.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1427    1.5578   -0.7870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7558   -0.0009   -1.4043 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3039    0.2616    1.4735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3687   -1.1481    0.6396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1039    0.1061    2.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7781    1.5712    1.0345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6555    0.5056   -0.9070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4175    0.0233    1.3825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0030    1.6034    0.8524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9371   -3.1685    0.0687 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  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 11 13  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  6
 10 27  1  0
 10 28  1  0
 13 29  1  0
M  END

HMDB0000206
     RDKit          3D
N6-Acetyl-L-lysine
 29 28  0  0  0  0  0  0  0  0999 V2000
    4.7961    0.5208    0.4283 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6959    0.1055   -0.4683 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9746   -0.5665   -1.4807 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3554    0.4511   -0.2026 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3241    0.0204   -1.1092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0497    0.4796   -0.6693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4169   -0.0499    0.6812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7868    0.4552    1.0409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8621    0.0327    0.0755 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1187    0.6102    0.5826 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0694   -1.4180    0.0062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1609   -1.9902    0.3464 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0798   -2.3085   -0.4430 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0750   -0.2966    1.1256 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6673    0.7693   -0.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5264    1.4585    0.9620 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1430    1.0234    0.6647 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3230   -1.0886   -1.1228 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5221    0.4801   -2.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1427    1.5578   -0.7870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7558   -0.0009   -1.4043 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3039    0.2616    1.4735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3687   -1.1481    0.6396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1039    0.1061    2.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7781    1.5712    1.0345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6555    0.5056   -0.9070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4175    0.0233    1.3825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0030    1.6034    0.8524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9371   -3.1685    0.0687 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  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 11 13  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  6
 10 27  1  0
 10 28  1  0
 13 29  1  0
M  END

HEADER    PROTEIN                                 14-NOV-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-NOV-19         0                                  
HETATM    1  C   UNK     0      -4.675   0.415   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.675   1.955   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -3.342  -0.355   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      -3.342  -1.894   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       1.993  -0.355   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.008   0.415   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.659   0.415   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.674  -0.355   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -6.009  -0.355   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.660  -0.355   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.660  -1.894   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.994   0.415   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       3.327   0.415   0.000  0.00  0.00           N+0
CONECT    1    2    3    9                                                  
CONECT    2    1                                                            
CONECT    3    1    4    6                                                  
CONECT    4    3                                                            
CONECT    5   13    7                                                       
CONECT    6    3    8                                                       
CONECT    7    5    8                                                       
CONECT    8    6    7                                                       
CONECT    9    1                                                            
CONECT   10   11   12   13                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    5   10                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

COMPND    HMDB0000206
HETATM    1  C1  UNL     1       4.796   0.521   0.428  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.696   0.106  -0.468  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.975  -0.567  -1.481  1.00  0.00           O  
HETATM    4  N1  UNL     1       2.355   0.451  -0.203  1.00  0.00           N  
HETATM    5  C3  UNL     1       1.324   0.020  -1.109  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.050   0.480  -0.669  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.417  -0.050   0.681  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.787   0.455   1.041  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.862   0.033   0.076  1.00  0.00           C  
HETATM   10  N2  UNL     1      -4.119   0.610   0.583  1.00  0.00           N  
HETATM   11  C8  UNL     1      -3.069  -1.418   0.006  1.00  0.00           C  
HETATM   12  O2  UNL     1      -4.161  -1.990   0.346  1.00  0.00           O  
HETATM   13  O3  UNL     1      -2.080  -2.308  -0.443  1.00  0.00           O  
HETATM   14  H1  UNL     1       5.075  -0.297   1.126  1.00  0.00           H  
HETATM   15  H2  UNL     1       5.667   0.769  -0.244  1.00  0.00           H  
HETATM   16  H3  UNL     1       4.526   1.458   0.962  1.00  0.00           H  
HETATM   17  H4  UNL     1       2.143   1.023   0.665  1.00  0.00           H  
HETATM   18  H5  UNL     1       1.323  -1.089  -1.123  1.00  0.00           H  
HETATM   19  H6  UNL     1       1.522   0.480  -2.086  1.00  0.00           H  
HETATM   20  H7  UNL     1      -0.143   1.558  -0.787  1.00  0.00           H  
HETATM   21  H8  UNL     1      -0.756  -0.001  -1.404  1.00  0.00           H  
HETATM   22  H9  UNL     1       0.304   0.262   1.473  1.00  0.00           H  
HETATM   23  H10 UNL     1      -0.369  -1.148   0.640  1.00  0.00           H  
HETATM   24  H11 UNL     1      -2.104   0.106   2.059  1.00  0.00           H  
HETATM   25  H12 UNL     1      -1.778   1.571   1.034  1.00  0.00           H  
HETATM   26  H13 UNL     1      -2.655   0.506  -0.907  1.00  0.00           H  
HETATM   27  H14 UNL     1      -4.418   0.023   1.382  1.00  0.00           H  
HETATM   28  H15 UNL     1      -4.003   1.603   0.852  1.00  0.00           H  
HETATM   29  H16 UNL     1      -1.937  -3.168   0.069  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3    3    4
CONECT    4    5   17
CONECT    5    6   18   19
CONECT    6    7   20   21
CONECT    7    8   22   23
CONECT    8    9   24   25
CONECT    9   10   11   26
CONECT   10   27   28
CONECT   11   12   12   13
CONECT   13   29
END

HMDB0000206
     RDKit          3D
N6-Acetyl-L-lysine
 29 28  0  0  0  0  0  0  0  0999 V2000
    4.7961    0.5208    0.4283 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6959    0.1055   -0.4683 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9746   -0.5665   -1.4807 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3554    0.4511   -0.2026 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3241    0.0204   -1.1092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0497    0.4796   -0.6693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4169   -0.0499    0.6812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7868    0.4552    1.0409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8621    0.0327    0.0755 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1187    0.6102    0.5826 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0694   -1.4180    0.0062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1609   -1.9902    0.3464 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0798   -2.3085   -0.4430 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0750   -0.2966    1.1256 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6673    0.7693   -0.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5264    1.4585    0.9620 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1430    1.0234    0.6647 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3230   -1.0886   -1.1228 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5221    0.4801   -2.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1427    1.5578   -0.7870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7558   -0.0009   -1.4043 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3039    0.2616    1.4735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3687   -1.1481    0.6396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1039    0.1061    2.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7781    1.5712    1.0345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6555    0.5056   -0.9070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4175    0.0233    1.3825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0030    1.6034    0.8524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9371   -3.1685    0.0687 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  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 11 13  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  6
 10 27  1  0
 10 28  1  0
 13 29  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2S)-6-(Acetylamino)-2-aminohexanoic acid	ChEBI
N(6)-ACETYLLYSINE	ChEBI
N(zeta)-Acetyllysine	ChEBI
N-epsilon-Acetyl-L-lysine	ChEBI
N-Epsilon-Acetyllysine	ChEBI
N(epsilon)-Acetyl-L-lysine	ChEBI
N(zeta)-Acetyl-L-lysine	ChEBI
(2S)-6-(Acetylamino)-2-aminohexanoate	Generator
N(Z)-Acetyllysine	Generator
N(Ζ)-acetyllysine	Generator
N(Z)-Acetyl-L-lysine	Generator
N(Ζ)-acetyl-L-lysine	Generator
e-Acetyl-L-lysine	HMDB
e-N-Acetyl-L-lysine	HMDB
e-N-Acetyllysine	HMDB
epsilon-Acetyl-L-lysine	HMDB
epsilon-N-Acetyl-L-lysine	HMDB
epsilon-N-Acetyllysine	HMDB
L-e-N-Acetyllysine	HMDB
L-epsilon-N-Acetyllysine	HMDB
N-e-Acetyl-L-lysine	HMDB
N-e-Acetyllysine	HMDB
N6-Acetyllysine	HMDB
Ne-acetyl-L-lysine	HMDB
Ne-acetyllysine	HMDB
Omega-N-acetyl-L-lysine	HMDB
W-N-Acetyl-L-lysine	HMDB
N(6)-Acetyllsine	HMDB
Omega-acetyllsine	HMDB
(2S)-6-Acetamido-2-aminohexanoic acid	HMDB
6-Acetamido-2-aminohexanoic acid	HMDB
L-Ε-N-acetyllysine	HMDB
Nepsilon-acetyl-L-lysine	HMDB
Nepsilon-acetyllysine	HMDB
Nε-acetyl-L-lysine	HMDB
Nε-acetyllysine	HMDB
Ε-acetyl-L-lysine	HMDB
Ε-N-acetyl-L-lysine	HMDB
Ε-N-acetyllysine	HMDB
Ω-N-acetyl-L-lysine	HMDB
N6-Acetyl-L-lysine	ChEBI

Chemical Formula

C₈H₁₆N₂O₃

Average Molecular Weight

188.2242

Monoisotopic Molecular Weight

188.116092388

IUPAC Name

(2S)-2-amino-6-acetamidohexanoic acid

Traditional Name

N6-acetyllysine

CAS Registry Number

692-04-6

SMILES

CC(=O)NCCCC[C@H](N)C(O)=O

InChI Identifier

InChI=1S/C8H16N2O3/c1-6(11)10-5-3-2-4-7(9)8(12)13/h7H,2-5,9H2,1H3,(H,10,11)(H,12,13)/t7-/m0/s1

InChI Key

DTERQYGMUDWYAZ-ZETCQYMHSA-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
Medium-chain fatty acid
Amino fatty acid
Fatty acid
Fatty acyl
Amino acid
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Primary amine
Organooxygen compound
Organonitrogen compound
Carbonyl group
Primary aliphatic amine
Organic nitrogen compound
Organic oxygen compound
Amine
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

N(6)-acyl-L-lysine (CHEBI:17752 )
acetyl-L-lysine (CHEBI:17752 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	250 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	8346 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	139.75	30932474
[M+H]+	MetCCS_train_pos	142.3	30932474
[M-H]-	Not Available	139.75	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000010
[M+H]+	Not Available	142.438	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000010

Predicted Molecular Properties

Property	Value	Source
Water Solubility	17.5 g/L	ALOGPS
logP	-2.6	ALOGPS
logP	-3.2	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	2.43	ChemAxon
pKa (Strongest Basic)	9.53	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	92.42 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	47.25 m³·mol⁻¹	ChemAxon
Polarizability	20.29 Å³	ChemAxon
Number of Rings	0	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
DarkChem	[M+H]+	145.387	31661259
DarkChem	[M-H]-	139.745	31661259
AllCCS	[M+H]+	143.046	32859911
AllCCS	[M-H]-	142.039	32859911
DeepCCS	[M+H]+	141.404	30932474
DeepCCS	[M-H]-	137.576	30932474
DeepCCS	[M-2H]-	175.101	30932474
DeepCCS	[M+Na]+	150.667	30932474
AllCCS	[M+H]+	143.0	32859911
AllCCS	[M+H-H2O]+	139.4	32859911
AllCCS	[M+NH4]+	146.5	32859911
AllCCS	[M+Na]+	147.5	32859911
AllCCS	[M-H]-	142.0	32859911
AllCCS	[M+Na-2H]-	143.4	32859911
AllCCS	[M+HCOO]-	144.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N6-Acetyl-L-lysine	CC(=O)NCCCC[C@H](N)C(O)=O	2661.9	Standard polar	33892256
N6-Acetyl-L-lysine	CC(=O)NCCCC[C@H](N)C(O)=O	1853.2	Standard non polar	33892256
N6-Acetyl-L-lysine	CC(=O)NCCCC[C@H](N)C(O)=O	2034.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N6-Acetyl-L-lysine,1TMS,isomer #1	CC(=O)NCCCC[C@H](N)C(=O)O[Si](C)(C)C	1829.2	Semi standard non polar	33892256
N6-Acetyl-L-lysine,1TMS,isomer #2	CC(=O)NCCCC[C@H](N[Si](C)(C)C)C(=O)O	1903.0	Semi standard non polar	33892256
N6-Acetyl-L-lysine,1TMS,isomer #3	CC(=O)N(CCCC[C@H](N)C(=O)O)[Si](C)(C)C	1877.2	Semi standard non polar	33892256
N6-Acetyl-L-lysine,2TMS,isomer #1	CC(=O)NCCCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1928.9	Semi standard non polar	33892256
N6-Acetyl-L-lysine,2TMS,isomer #1	CC(=O)NCCCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1922.8	Standard non polar	33892256
N6-Acetyl-L-lysine,2TMS,isomer #1	CC(=O)NCCCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	2389.5	Standard polar	33892256
N6-Acetyl-L-lysine,2TMS,isomer #2	CC(=O)N(CCCC[C@H](N)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1821.4	Semi standard non polar	33892256
N6-Acetyl-L-lysine,2TMS,isomer #2	CC(=O)N(CCCC[C@H](N)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1946.0	Standard non polar	33892256
N6-Acetyl-L-lysine,2TMS,isomer #2	CC(=O)N(CCCC[C@H](N)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2687.9	Standard polar	33892256
N6-Acetyl-L-lysine,2TMS,isomer #3	CC(=O)N(CCCC[C@H](N[Si](C)(C)C)C(=O)O)[Si](C)(C)C	1945.8	Semi standard non polar	33892256
N6-Acetyl-L-lysine,2TMS,isomer #3	CC(=O)N(CCCC[C@H](N[Si](C)(C)C)C(=O)O)[Si](C)(C)C	1942.8	Standard non polar	33892256
N6-Acetyl-L-lysine,2TMS,isomer #3	CC(=O)N(CCCC[C@H](N[Si](C)(C)C)C(=O)O)[Si](C)(C)C	2495.9	Standard polar	33892256
N6-Acetyl-L-lysine,2TMS,isomer #4	CC(=O)NCCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2070.9	Semi standard non polar	33892256
N6-Acetyl-L-lysine,2TMS,isomer #4	CC(=O)NCCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1967.0	Standard non polar	33892256
N6-Acetyl-L-lysine,2TMS,isomer #4	CC(=O)NCCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2560.6	Standard polar	33892256
N6-Acetyl-L-lysine,3TMS,isomer #1	CC(=O)N(CCCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1920.1	Semi standard non polar	33892256
N6-Acetyl-L-lysine,3TMS,isomer #1	CC(=O)N(CCCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1993.5	Standard non polar	33892256
N6-Acetyl-L-lysine,3TMS,isomer #1	CC(=O)N(CCCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2125.8	Standard polar	33892256
N6-Acetyl-L-lysine,3TMS,isomer #2	CC(=O)NCCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2088.7	Semi standard non polar	33892256
N6-Acetyl-L-lysine,3TMS,isomer #2	CC(=O)NCCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2032.4	Standard non polar	33892256
N6-Acetyl-L-lysine,3TMS,isomer #2	CC(=O)NCCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2223.3	Standard polar	33892256
N6-Acetyl-L-lysine,3TMS,isomer #3	CC(=O)N(CCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2048.3	Semi standard non polar	33892256
N6-Acetyl-L-lysine,3TMS,isomer #3	CC(=O)N(CCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2060.4	Standard non polar	33892256
N6-Acetyl-L-lysine,3TMS,isomer #3	CC(=O)N(CCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2282.7	Standard polar	33892256
N6-Acetyl-L-lysine,4TMS,isomer #1	CC(=O)N(CCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2083.9	Semi standard non polar	33892256
N6-Acetyl-L-lysine,4TMS,isomer #1	CC(=O)N(CCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2104.0	Standard non polar	33892256
N6-Acetyl-L-lysine,4TMS,isomer #1	CC(=O)N(CCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2041.3	Standard polar	33892256
N6-Acetyl-L-lysine,1TBDMS,isomer #1	CC(=O)NCCCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C	2103.5	Semi standard non polar	33892256
N6-Acetyl-L-lysine,1TBDMS,isomer #2	CC(=O)NCCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O	2168.1	Semi standard non polar	33892256
N6-Acetyl-L-lysine,1TBDMS,isomer #3	CC(=O)N(CCCC[C@H](N)C(=O)O)[Si](C)(C)C(C)(C)C	2090.8	Semi standard non polar	33892256
N6-Acetyl-L-lysine,2TBDMS,isomer #1	CC(=O)NCCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2410.9	Semi standard non polar	33892256
N6-Acetyl-L-lysine,2TBDMS,isomer #1	CC(=O)NCCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2341.9	Standard non polar	33892256
N6-Acetyl-L-lysine,2TBDMS,isomer #1	CC(=O)NCCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2481.0	Standard polar	33892256
N6-Acetyl-L-lysine,2TBDMS,isomer #2	CC(=O)N(CCCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2291.7	Semi standard non polar	33892256
N6-Acetyl-L-lysine,2TBDMS,isomer #2	CC(=O)N(CCCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2373.5	Standard non polar	33892256
N6-Acetyl-L-lysine,2TBDMS,isomer #2	CC(=O)N(CCCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2713.8	Standard polar	33892256
N6-Acetyl-L-lysine,2TBDMS,isomer #3	CC(=O)N(CCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	2417.2	Semi standard non polar	33892256
N6-Acetyl-L-lysine,2TBDMS,isomer #3	CC(=O)N(CCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	2369.6	Standard non polar	33892256
N6-Acetyl-L-lysine,2TBDMS,isomer #3	CC(=O)N(CCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	2569.5	Standard polar	33892256
N6-Acetyl-L-lysine,2TBDMS,isomer #4	CC(=O)NCCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2534.8	Semi standard non polar	33892256
N6-Acetyl-L-lysine,2TBDMS,isomer #4	CC(=O)NCCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2381.5	Standard non polar	33892256
N6-Acetyl-L-lysine,2TBDMS,isomer #4	CC(=O)NCCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2580.1	Standard polar	33892256
N6-Acetyl-L-lysine,3TBDMS,isomer #1	CC(=O)N(CCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2606.9	Semi standard non polar	33892256
N6-Acetyl-L-lysine,3TBDMS,isomer #1	CC(=O)N(CCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2589.1	Standard non polar	33892256
N6-Acetyl-L-lysine,3TBDMS,isomer #1	CC(=O)N(CCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2472.3	Standard polar	33892256
N6-Acetyl-L-lysine,3TBDMS,isomer #2	CC(=O)NCCCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2769.3	Semi standard non polar	33892256
N6-Acetyl-L-lysine,3TBDMS,isomer #2	CC(=O)NCCCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2626.4	Standard non polar	33892256
N6-Acetyl-L-lysine,3TBDMS,isomer #2	CC(=O)NCCCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2486.9	Standard polar	33892256
N6-Acetyl-L-lysine,3TBDMS,isomer #3	CC(=O)N(CCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2703.9	Semi standard non polar	33892256
N6-Acetyl-L-lysine,3TBDMS,isomer #3	CC(=O)N(CCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2645.1	Standard non polar	33892256
N6-Acetyl-L-lysine,3TBDMS,isomer #3	CC(=O)N(CCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2546.8	Standard polar	33892256
N6-Acetyl-L-lysine,4TBDMS,isomer #1	CC(=O)N(CCCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2947.8	Semi standard non polar	33892256
N6-Acetyl-L-lysine,4TBDMS,isomer #1	CC(=O)N(CCCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2847.3	Standard non polar	33892256
N6-Acetyl-L-lysine,4TBDMS,isomer #1	CC(=O)N(CCCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2490.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - N6-Acetyl-L-lysine GC-MS (3 TMS)	splash10-0002-9610000000-6e30cfdb2a70cc49f983	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N6-Acetyl-L-lysine GC-MS (Non-derivatized)	splash10-0002-9610000000-6e30cfdb2a70cc49f983	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N6-Acetyl-L-lysine GC-EI-TOF (Non-derivatized)	splash10-004i-1900000000-e36d5532f4f0ed8ec34f	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N6-Acetyl-L-lysine GC-EI-TOF (Non-derivatized)	splash10-0002-9500000000-266c8b0fce84c71553b2	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N6-Acetyl-L-lysine GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9200000000-a186b34425c93ea31a66	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N6-Acetyl-L-lysine GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9110000000-255e47c2dfcdf6b61403	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N6-Acetyl-L-lysine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N6-Acetyl-L-lysine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N6-Acetyl-L-lysine GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N6-Acetyl-L-lysine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N6-Acetyl-L-lysine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N6-Acetyl-L-lysine GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - N6-Acetyl-L-lysine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-004r-1900000000-4745f7cfa9eaaef208ad	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N6-Acetyl-L-lysine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-001i-9000000000-635805826359aa05ec7c	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N6-Acetyl-L-lysine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-001i-9000000000-8857489c6ac957c71a5d	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N6-Acetyl-L-lysine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF	splash10-000i-0900000000-39f91157038523017046	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N6-Acetyl-L-lysine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF	splash10-000j-0900000000-183e1f50c20603f14c03	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N6-Acetyl-L-lysine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOF	splash10-0002-1900000000-da02d0f8bd73b5b96b46	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N6-Acetyl-L-lysine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOF	splash10-0a4j-9400000000-8531cdbb4e8108dbec95	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N6-Acetyl-L-lysine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOF	splash10-0a4l-9000000000-94d72f2c644db8c0b5cd	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N6-Acetyl-L-lysine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOF	splash10-000i-0900000000-c6ff005564503774a853	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N6-Acetyl-L-lysine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOF	splash10-004i-3900000000-dffc604f608a010e711e	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N6-Acetyl-L-lysine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOF	splash10-001i-9000000000-d6bc330de42890c4c091	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N6-Acetyl-L-lysine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOF	splash10-001i-9000000000-8d68337bf7a8db380cd7	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N6-Acetyl-L-lysine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOF	splash10-001i-9000000000-1400569a447d5f66c3a8	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N6-Acetyl-L-lysine LC-ESI-QQ , negative-QTOF	splash10-000i-0900000000-39f91157038523017046	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N6-Acetyl-L-lysine LC-ESI-QQ , negative-QTOF	splash10-000j-0900000000-183e1f50c20603f14c03	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N6-Acetyl-L-lysine LC-ESI-QQ , negative-QTOF	splash10-0002-1900000000-da02d0f8bd73b5b96b46	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N6-Acetyl-L-lysine LC-ESI-QQ , negative-QTOF	splash10-0a4j-9400000000-8531cdbb4e8108dbec95	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N6-Acetyl-L-lysine LC-ESI-QQ , negative-QTOF	splash10-0a4l-9000000000-94d72f2c644db8c0b5cd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N6-Acetyl-L-lysine LC-ESI-QQ , positive-QTOF	splash10-000i-0900000000-c6ff005564503774a853	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N6-Acetyl-L-lysine 10V, Positive-QTOF	splash10-0077-0900000000-e0d9659d3d504e9c8d81	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N6-Acetyl-L-lysine 20V, Positive-QTOF	splash10-0ued-3900000000-ae84e0c568d22d7c62fb	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N6-Acetyl-L-lysine 40V, Positive-QTOF	splash10-001i-9100000000-848f804e26f5a4edfcfb	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N6-Acetyl-L-lysine 10V, Negative-QTOF	splash10-000i-0900000000-545e3c760ee61913f301	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N6-Acetyl-L-lysine 20V, Negative-QTOF	splash10-05p2-3900000000-3a6e9f0c90d936bd6ae8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N6-Acetyl-L-lysine 40V, Negative-QTOF	splash10-052f-9000000000-33c2ede158e490bcc70f	2017-09-01	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)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Blood
Feces
Saliva
Urine

Tissue Locations

Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	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	27065191	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	2.036-2.828 umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	6022933	details
Urine	Detected and Quantified	9.318 +/- 4.75 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected and Quantified	1.14 (0.90-1.49) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	Analysis of 40 NI...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	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
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Attachment loss	31026179	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Periodontal Probing Depth	31026179	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Supragingival Plaque	31026179	details
Urine	Detected and Quantified	10.141 +/- 3.949 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details

Associated Disorders and Diseases

Disease References

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 ]
Attachment loss
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Periodontal Probing Depth
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Supragingival Plaque
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000476

KNApSAcK ID

Not Available

Chemspider ID

83801

KEGG Compound ID

C02727

BioCyc ID

CPD-567

BiGG ID

Not Available

Wikipedia Link

Acetyllysine

METLIN ID

5216

PubChem Compound

92832

PDB ID

Not Available

ChEBI ID

17752

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1266461

References

Synthesis Reference

Benoiton, Leo; Leclerc, Jean. An improved synthesis of e-N-acetyl-L-lysine and similar compounds. Canadian Journal of Chemistry (1965), 43(4), 991-3.

Material Safety Data Sheet (MSDS)

Not Available

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 ]
Jacobson RH, Ladurner AG, King DS, Tjian R: Structure and function of a human TAFII250 double bromodomain module. Science. 2000 May 26;288(5470):1422-5. [PubMed:10827952 ]
Armstrong MD, Robinow M: A case of hyperlysinemia: biochemical and clinical observations. Pediatrics. 1967 Apr;39(4):546-54. [PubMed:6022933 ]
Crane-Robinson C, Hebbes TR, Clayton AL, Thorne AW: Chromosomal mapping of core histone acetylation by immunoselection. Methods. 1997 May;12(1):48-56. [PubMed:9169194 ]
Jamonnak N, Fatkins DG, Wei L, Zheng W: N(epsilon)-methanesulfonyl-lysine as a non-hydrolyzable functional surrogate for N(epsilon)-acetyl-lysine. Org Biomol Chem. 2007 Mar 21;5(6):892-6. Epub 2007 Feb 5. [PubMed:17340003 ]
Iwabata H, Yoshida M, Komatsu Y: Proteomic analysis of organ-specific post-translational lysine-acetylation and -methylation in mice by use of anti-acetyllysine and -methyllysine mouse monoclonal antibodies. Proteomics. 2005 Dec;5(18):4653-64. [PubMed:16247734 ]
Hazen SL, d'Avignon A, Anderson MM, Hsu FF, Heinecke JW: Human neutrophils employ the myeloperoxidase-hydrogen peroxide-chloride system to oxidize alpha-amino acids to a family of reactive aldehydes. Mechanistic studies identifying labile intermediates along the reaction pathway. J Biol Chem. 1998 Feb 27;273(9):4997-5005. [PubMed:9478947 ]
Sterner DE, Berger SL: Acetylation of histones and transcription-related factors. Microbiol Mol Biol Rev. 2000 Jun;64(2):435-59. [PubMed:10839822 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
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 ]
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 ]

Showing metabocard for N6-Acetyl-L-lysine (HMDB0000206)

MOL for HMDB0000206 (N6-Acetyl-L-lysine)

3D MOL for HMDB0000206 (N6-Acetyl-L-lysine)

3D SDF for HMDB0000206 (N6-Acetyl-L-lysine)

3D-SDF for HMDB0000206 (N6-Acetyl-L-lysine)

PDB for HMDB0000206 (N6-Acetyl-L-lysine)

3D PDB for HMDB0000206 (N6-Acetyl-L-lysine)

SMILES for HMDB0000206 (N6-Acetyl-L-lysine)

INCHI for HMDB0000206 (N6-Acetyl-L-lysine)

Structure for HMDB0000206 (N6-Acetyl-L-lysine)

3D Structure for HMDB0000206 (N6-Acetyl-L-lysine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra