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

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:48:20 UTC
HMDB IDHMDB0000206
Secondary Accession Numbers
  • HMDB00206
Metabolite Identification
Common NameN6-Acetyl-L-lysine
DescriptionN-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
Data?1582752116
MOLSDF3D SDFPDB3D PDBSMILESInChI

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


  Mrv1652311141918292D          

 13 12  0  0  1  0            999 V2000
   -2.5047    0.2225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5047    1.0475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7902   -0.1900    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7902   -1.0149    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0676   -0.1900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0757    0.2225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3531    0.2225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3612   -0.1900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2192   -0.1900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4965   -0.1900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4965   -1.0149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2110    0.2225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7821    0.2225    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  3  4  1  6  0  0  0
  3  6  1  0  0  0  0
 13  5  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  8  1  0  0  0  0
  9  1  1  0  0  0  0
 11 10  2  0  0  0  0
 12 10  1  0  0  0  0
 13 10  1  0  0  0  0
M  END
Download

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

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

  Mrv1652311141918292D          

 13 12  0  0  1  0            999 V2000
   -2.5047    0.2225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5047    1.0475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7902   -0.1900    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7902   -1.0149    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0676   -0.1900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0757    0.2225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3531    0.2225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3612   -0.1900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2192   -0.1900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4965   -0.1900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4965   -1.0149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2110    0.2225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7821    0.2225    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  3  4  1  6  0  0  0
  3  6  1  0  0  0  0
 13  5  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  8  1  0  0  0  0
  9  1  1  0  0  0  0
 11 10  2  0  0  0  0
 12 10  1  0  0  0  0
 13 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000206

> <DATABASE_NAME>
hmdb

> <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

> <FORMULA>
C8H16N2O3

> <MOLECULAR_WEIGHT>
188.2242

> <EXACT_MASS>
188.116092388

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
20.288899867682026

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-6-acetamidohexanoic acid

> <ALOGPS_LOGP>
-2.58

> <JCHEM_LOGP>
-3.153974962346684

> <ALOGPS_LOGS>
-1.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.009273158088497

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.431122734632985

> <JCHEM_PKA_STRONGEST_BASIC>
9.526531386952614

> <JCHEM_POLAR_SURFACE_AREA>
92.41999999999999

> <JCHEM_REFRACTIVITY>
47.2533

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.75e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N6-acetyllysine

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for HMDB0000206 (N6-Acetyl-L-lysine)
https://cactus.nci.nih.gov/chemical/structure/CC(=O)NCCCC%5BC@H%5D(N)C(O)=O/f...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:28})
 29 28  0  0  0  0  0  0  0  0999 V2000
    5.7636   -0.8250    0.5159 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5746   -0.0542    0.0029 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7414    0.9510   -0.6549 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3258   -0.4819    0.2751 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1699    0.2674   -0.2236 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8813   -0.4262    0.2227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3258    0.3563   -0.2981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6145   -0.3374    0.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8216    0.4452   -0.3726 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7416    0.5596   -1.4536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8552    1.7711    0.2590 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0870   -0.3024   -0.0389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4738   -1.3394   -0.7982 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7530    0.0317    0.9122 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6818   -0.3308    0.1979 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7298   -0.8630    1.6047 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7395   -1.8387    0.1160 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1924   -1.2858    0.8012 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1941    1.2812    0.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2038    0.3055   -1.3124 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8573   -1.4400   -0.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8476   -0.4642    1.3115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3017    1.3700    0.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2920    0.3944   -1.3869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6386   -1.3511   -0.2516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6483   -0.3753    1.2370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9292    1.6920    1.2622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0475    2.3165   -0.0021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2923   -1.7877   -0.5449 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 15  1  0  0  0  0
  1 16  1  0  0  0  0
  1 17  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 18  1  0  0  0  0
  5  6  1  0  0  0  0
  5 19  1  0  0  0  0
  5 20  1  0  0  0  0
  6  7  1  0  0  0  0
  6 21  1  0  0  0  0
  6 22  1  0  0  0  0
  7  8  1  0  0  0  0
  7 23  1  0  0  0  0
  7 24  1  0  0  0  0
  8  9  1  0  0  0  0
  8 25  1  0  0  0  0
  8 26  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
 11 27  1  0  0  0  0
 11 28  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 13 29  1  0  0  0  0
M  END
$$$$

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

Download
3D PDB for HMDB0000206 (N6-Acetyl-L-lysine)
COMPND    https://cactus.nci.nih.gov/chemical/structure/CC(=O)NCCCC%5BC@H%5D(N)C(O)=O/f... 
AUTHOR    GENERATED BY OPEN BABEL 3.1.0
HETATM    1  C   UNK     1       5.764  -0.825   0.516  1.00  0.00           C  
HETATM    2  C   UNK     1       4.575  -0.054   0.003  1.00  0.00           C  
HETATM    3  O   UNK     1       4.741   0.951  -0.655  1.00  0.00           O  
HETATM    4  N   UNK     1       3.326  -0.482   0.275  1.00  0.00           N  
HETATM    5  C   UNK     1       2.170   0.267  -0.224  1.00  0.00           C  
HETATM    6  C   UNK     1       0.881  -0.426   0.223  1.00  0.00           C  
HETATM    7  C   UNK     1      -0.326   0.356  -0.298  1.00  0.00           C  
HETATM    8  C   UNK     1      -1.615  -0.337   0.148  1.00  0.00           C  
HETATM    9  C   UNK     1      -2.822   0.445  -0.373  1.00  0.00           C  
HETATM   10  H   UNK     1      -2.742   0.560  -1.454  1.00  0.00           H  
HETATM   11  N   UNK     1      -2.855   1.771   0.259  1.00  0.00           N  
HETATM   12  C   UNK     1      -4.087  -0.302  -0.039  1.00  0.00           C  
HETATM   13  O   UNK     1      -4.474  -1.339  -0.798  1.00  0.00           O  
HETATM   14  O   UNK     1      -4.753   0.032   0.912  1.00  0.00           O  
HETATM   15  H   UNK     1       6.682  -0.331   0.198  1.00  0.00           H  
HETATM   16  H   UNK     1       5.730  -0.863   1.605  1.00  0.00           H  
HETATM   17  H   UNK     1       5.739  -1.839   0.116  1.00  0.00           H  
HETATM   18  H   UNK     1       3.192  -1.286   0.801  1.00  0.00           H  
HETATM   19  H   UNK     1       2.194   1.281   0.176  1.00  0.00           H  
HETATM   20  H   UNK     1       2.204   0.305  -1.312  1.00  0.00           H  
HETATM   21  H   UNK     1       0.857  -1.440  -0.177  1.00  0.00           H  
HETATM   22  H   UNK     1       0.848  -0.464   1.312  1.00  0.00           H  
HETATM   23  H   UNK     1      -0.302   1.370   0.102  1.00  0.00           H  
HETATM   24  H   UNK     1      -0.292   0.394  -1.387  1.00  0.00           H  
HETATM   25  H   UNK     1      -1.639  -1.351  -0.252  1.00  0.00           H  
HETATM   26  H   UNK     1      -1.648  -0.375   1.237  1.00  0.00           H  
HETATM   27  H   UNK     1      -2.929   1.692   1.262  1.00  0.00           H  
HETATM   28  H   UNK     1      -2.047   2.317  -0.002  1.00  0.00           H  
HETATM   29  H   UNK     1      -5.292  -1.788  -0.545  1.00  0.00           H  
CONECT    1    2   15   16   17                                       
CONECT    2    1    3    3    4                                       
CONECT    3    2    2                                                 
CONECT    4    2    5   18                                            
CONECT    5    4    6   19   20                                       
CONECT    6    5    7   21   22                                       
CONECT    7    6    8   23   24                                       
CONECT    8    7    9   25   26                                       
CONECT    9    8   10   11   12                                       
CONECT   10    9                                                      
CONECT   11    9   27   28                                            
CONECT   12    9   13   14   14                                       
CONECT   13   12   29                                                 
CONECT   14   12   12                                                 
CONECT   15    1                                                      
CONECT   16    1                                                      
CONECT   17    1                                                      
CONECT   18    4                                                      
CONECT   19    5                                                      
CONECT   20    5                                                      
CONECT   21    6                                                      
CONECT   22    6                                                      
CONECT   23    7                                                      
CONECT   24    7                                                      
CONECT   25    8                                                      
CONECT   26    8                                                      
CONECT   27   11                                                      
CONECT   28   11                                                      
CONECT   29   13                                                      
MASTER        0    0    0    0    0    0    0    0   29    0   29    0
END

Download
SMILES for HMDB0000206 (N6-Acetyl-L-lysine)
CC(=O)NCCCC[C@H](N)C(O)=O
Download
INCHI for HMDB0000206 (N6-Acetyl-L-lysine)
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
Download
View in JSmolView Stereo Labels
Synonyms
ValueSource
(2S)-6-(Acetylamino)-2-aminohexanoic acidChEBI
N(6)-ACETYLLYSINEChEBI
N(zeta)-AcetyllysineChEBI
N-epsilon-Acetyl-L-lysineChEBI
N-Epsilon-AcetyllysineChEBI
N(epsilon)-Acetyl-L-lysineChEBI
N(zeta)-Acetyl-L-lysineChEBI
(2S)-6-(Acetylamino)-2-aminohexanoateGenerator
N(Z)-AcetyllysineGenerator
N(Ζ)-acetyllysineGenerator
N(Z)-Acetyl-L-lysineGenerator
N(Ζ)-acetyl-L-lysineGenerator
e-Acetyl-L-lysineHMDB
e-N-Acetyl-L-lysineHMDB
e-N-AcetyllysineHMDB
epsilon-Acetyl-L-lysineHMDB
epsilon-N-Acetyl-L-lysineHMDB
epsilon-N-AcetyllysineHMDB
L-e-N-AcetyllysineHMDB
L-epsilon-N-AcetyllysineHMDB
N-e-Acetyl-L-lysineHMDB
N-e-AcetyllysineHMDB
N6-AcetyllysineHMDB
Ne-acetyl-L-lysineHMDB
Ne-acetyllysineHMDB
Omega-N-acetyl-L-lysineHMDB
W-N-Acetyl-L-lysineHMDB
N(6)-AcetyllsineHMDB
Omega-acetyllsineHMDB
(2S)-6-Acetamido-2-aminohexanoic acidHMDB
6-Acetamido-2-aminohexanoic acidHMDB
L-Ε-N-acetyllysineHMDB
Nepsilon-acetyl-L-lysineHMDB
Nepsilon-acetyllysineHMDB
Nε-acetyl-L-lysineHMDB
Nε-acetyllysineHMDB
Ε-acetyl-L-lysineHMDB
Ε-N-acetyl-L-lysineHMDB
Ε-N-acetyllysineHMDB
Ω-N-acetyl-L-lysineHMDB
N6-Acetyl-L-lysineChEBI
Chemical FormulaC8H16N2O3
Average Molecular Weight188.2242
Monoisotopic Molecular Weight188.116092388
IUPAC Name(2S)-2-amino-6-acetamidohexanoic acid
Traditional NameN6-acetyllysine
CAS Registry Number692-04-6
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 KeyDTERQYGMUDWYAZ-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.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentL-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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Health effect:
Disposition
Route of exposure:
Source:
Biological location:
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point250 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility17.5 g/LALOGPS
logP-2.6ALOGPS
logP-3.2ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)2.43ChemAxon
pKa (Strongest Basic)9.53ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area92.42 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity47.25 m³·mol⁻¹ChemAxon
Polarizability20.29 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties
Collision Cross Sections
NameAdductTypeData SourceValueReference
DeepCCS[M-H]-ExperimentalMetCCS_train_neg139.7530932474  
DeepCCS[M+H]+ExperimentalMetCCS_train_pos142.330932474  
AllCCS[M-H]-ExperimentalNot Available139.75http://allccs.zhulab.cn/database/detail?ID=AllCCS00000010  
AllCCS[M+H]+ExperimentalNot Available142.438http://allccs.zhulab.cn/database/detail?ID=AllCCS00000010  
DarkChem[M+H]+PredictedNot Available145.38731661259  
DarkChem[M-H]-PredictedNot Available139.74531661259  
AllCCS[M+H]+PredictedNot Available143.04632859911  
AllCCS[M-H]-PredictedNot Available142.03932859911  
Retention Indices
Underivatized
Not Available
Derivatized
DerivativeValueReference
N6-Acetyl-L-lysine,1TMS,#11829.2021https://arxiv.org/abs/1905.12712
N6-Acetyl-L-lysine,1TMS,#21903.0305https://arxiv.org/abs/1905.12712
N6-Acetyl-L-lysine,1TMS,#31877.1987https://arxiv.org/abs/1905.12712
N6-Acetyl-L-lysine,1TBDMS,#12103.4568https://arxiv.org/abs/1905.12712
N6-Acetyl-L-lysine,1TBDMS,#22168.1458https://arxiv.org/abs/1905.12712
N6-Acetyl-L-lysine,1TBDMS,#32090.764https://arxiv.org/abs/1905.12712
Spectra
GC-MS
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0002-9610000000-6e30cfdb2a70cc49f9832014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0002-9610000000-6e30cfdb2a70cc49f9832017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-1900000000-e36d5532f4f0ed8ec34f2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-9500000000-266c8b0fce84c71553b22017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9200000000-a186b34425c93ea31a662017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9110000000-255e47c2dfcdf6b614032017-10-06View Spectrum
LC-MS/MS
Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004r-1900000000-4745f7cfa9eaaef208ad2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9000000000-635805826359aa05ec7c2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9000000000-8857489c6ac957c71a5d2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-0900000000-39f911570385230170462012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000j-0900000000-183e1f50c20603f14c032012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0002-1900000000-da02d0f8bd73b5b96b462012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4j-9400000000-8531cdbb4e8108dbec952012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4l-9000000000-94d72f2c644db8c0b5cd2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-000i-0900000000-c6ff005564503774a8532012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-004i-3900000000-dffc604f608a010e711e2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-001i-9000000000-d6bc330de42890c4c0912012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-001i-9000000000-8d68337bf7a8db380cd72012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-001i-9000000000-1400569a447d5f66c3a82012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0900000000-39f911570385230170462017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000j-0900000000-183e1f50c20603f14c032017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-1900000000-da02d0f8bd73b5b96b462017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4j-9400000000-8531cdbb4e8108dbec952017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4l-9000000000-94d72f2c644db8c0b5cd2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-0900000000-c6ff005564503774a8532017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  10V, Positivesplash10-0077-0900000000-e0d9659d3d504e9c8d812017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  20V, Positivesplash10-0ued-3900000000-ae84e0c568d22d7c62fb2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  40V, Positivesplash10-001i-9100000000-848f804e26f5a4edfcfb2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  10V, Negativesplash10-000i-0900000000-545e3c760ee61913f3012017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  20V, Negativesplash10-05p2-3900000000-3a6e9f0c90d936bd6ae82017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  40V, Negativesplash10-052f-9000000000-33c2ede158e490bcc70f2017-09-01View Spectrum
NMR
Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, predicted)2012-12-05View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
    • 

  • Feces
    • 

  • Saliva
    • 

  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
 
Normal
      Not Available
  details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal  details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
 
Normal		  details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
 
Normal		  details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
 
Normal		  details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
 
Normal		  details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
 
Normal		  details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
 
Normal		  details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
 
Normal		  details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
 
Normal		  details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
 
Normal		  details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
 
Normal		  details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
 
Normal		  details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
 
Normal		  details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
 
Normal		  details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
 
Normal		  details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal  details
UrineDetected and Quantified2.036-2.828 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal  details
UrineDetected and Quantified9.318 +/- 4.75 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
 
Normal
    • Mordechai, Hien, ...
  details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
 
Colorectal cancer		  details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer  details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
 
Colorectal cancer		  details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleAttachment loss   details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MalePeriodontal Probing Depth  details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleSupragingival Plaque  details
UrineDetected and Quantified10.141 +/- 3.949 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
 
Eosinophilic esophagitis
    • Mordechai, Hien, ...
  details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. 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  ] 
  2. 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  ] 
  3. 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
  1. 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
  1. 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
  1. 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
  1.  (). Mordechai, Hien, and David S. Wishart. . 
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB000476  
KNApSAcK IDNot Available
Chemspider ID83801  
KEGG Compound IDC02727  
BioCyc IDCPD-567  
BiGG IDNot Available
Wikipedia LinkAcetyllysine  
METLIN ID5216  
PubChem Compound92832  
PDB IDNot Available
ChEBI ID17752  
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceBenoiton, 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)Download (PDF)
General References
  1. Armstrong MD, Robinow M: A case of hyperlysinemia: biochemical and clinical observations. Pediatrics. 1967 Apr;39(4):546-54. [PubMed:6022933  ] 
  2. 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  ] 
  3. 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  ] 
  4. 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  ] 
  5. 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  ] 
  6. 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  ] 
  7. Sterner DE, Berger SL: Acetylation of histones and transcription-related factors. Microbiol Mol Biol Rev. 2000 Jun;64(2):435-59. [PubMed:10839822  ] 
  8. 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  ] 
  9. 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  ] 
  10. 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  ] 
  11. 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  ] 
  12. 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  ]