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Showing metabocard for N-alpha-Acetyl-L-lysine (HMDB0000446)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-05-30 20:55:52 UTC
HMDB IDHMDB0000446
Secondary Accession Numbers
  • HMDB00446
Metabolite Identification
Common NameN-alpha-Acetyl-L-lysine
DescriptionN-alpha-Acetyl-L-lysine also known as Nalpha-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 its terminal nitrogen atom. N-alpha-Acetyl-L-lysine can also be classified as an alpha amino acid or a derivatized alpha amino acid. Technically, N-alpha-Acetyl-L-lysine is a biologically available N-terminal capped form of the proteinogenic alpha amino acid L-lysine. Unlike L-lysine, acetylated lysine derivatives such as N-alpha-Acetyl-L-lysine are zwitterionic compounds. These are molecules that contains an equal number of positively- and negatively-charged functional groups. N-alpha-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 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’s (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-alpha-Acetyl-L-lysine 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 lysine can also occur. In particular, N-alpha-Acetyl-L-lysine can be biosynthesized from L-lysine and acetyl-CoA via the enzyme known as Lysine N-acetyltransferase. Individuals with hyperlysinaemia due to L-lysine alpha-ketoglutarate reductase deficiency will excrete high levels of N-alpha-Acetyl-L-lysine in their urine (PMID: 116084 ). L-lysine alpha-ketoglutarate reductase deficiency, if untreated, can lead to neurological and behavioral deficits (PMID: 116084 ). 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?1676999690
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000446 (N-alpha-Acetyl-L-lysine)


  Mrv1652304202022152D          

 13 12  0  0  0  0            999 V2000
 9998.1805 9996.7084    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.4668 9996.2951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7529 9996.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0388 9996.2951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.3247 9996.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.6105 9996.2951    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1805 9997.5323    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8942 9997.9449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6100 9997.5323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8942 9998.7699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8942 9996.2951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6100 9996.7084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8942 9995.4706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  6  0  0  0
  1 11  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
M  END
Download

3D MOL for HMDB0000446 (N-alpha-Acetyl-L-lysine)

HMDB0000446
     RDKit          3D
N-alpha-Acetyl-L-lysine
 29 28  0  0  0  0  0  0  0  0999 V2000
   -4.2867   -1.7349   -0.5531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9838   -1.2683   -0.0793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4306   -1.8966    0.8720 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2894   -0.1599   -0.6072 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9815    0.2657   -0.0931 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0647    0.1146   -1.1668 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4486    0.5174   -0.7514 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9286   -0.2947    0.4311 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3123    0.1039    0.8519 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2894   -0.0744   -0.1887 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0650    1.6299    0.4563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1344    2.2634    0.3968 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0351    2.2109    1.0393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0538   -0.9500   -0.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3421   -1.8443   -1.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5664   -2.6976   -0.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7029    0.3787   -1.3802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6758   -0.4223    0.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2378    0.6846   -2.0955 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0691   -0.9553   -1.5115 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4794    1.6049   -0.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1649    0.2886   -1.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2720   -0.2249    1.3121 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9424   -1.3643    0.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3283    1.1662    1.1506 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6055   -0.5502    1.7060 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5578    0.8244   -0.6245 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9309   -0.7758   -0.8621 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3211    3.1605    0.8456 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
  5 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  1
  6 19  1  0
  6 20  1  0
  7 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 13 29  1  0
M  END
Download

3D SDF for HMDB0000446 (N-alpha-Acetyl-L-lysine)


  Mrv1652304202022152D          

 13 12  0  0  0  0            999 V2000
 9998.1805 9996.7084    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.4668 9996.2951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7529 9996.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0388 9996.2951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.3247 9996.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.6105 9996.2951    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1805 9997.5323    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8942 9997.9449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6100 9997.5323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8942 9998.7699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8942 9996.2951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6100 9996.7084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8942 9995.4706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  6  0  0  0
  1 11  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000446

> <DATABASE_NAME>
hmdb

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

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

> <INCHI_KEY>
VEYYWZRYIYDQJM-ZETCQYMHSA-N

> <FORMULA>
C8H16N2O3

> <MOLECULAR_WEIGHT>
188.227

> <EXACT_MASS>
188.116092383

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
19.961306276615304

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-2.54

> <JCHEM_LOGP>
-3.154849831228551

> <ALOGPS_LOGS>
-1.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.916998108448613

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8943963051732786

> <JCHEM_PKA_STRONGEST_BASIC>
10.205475361447382

> <JCHEM_POLAR_SURFACE_AREA>
92.41999999999999

> <JCHEM_REFRACTIVITY>
47.2533

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.61e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nα-acetyllysine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0000446 (N-alpha-Acetyl-L-lysine)

HMDB0000446
     RDKit          3D
N-alpha-Acetyl-L-lysine
 29 28  0  0  0  0  0  0  0  0999 V2000
   -4.2867   -1.7349   -0.5531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9838   -1.2683   -0.0793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4306   -1.8966    0.8720 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2894   -0.1599   -0.6072 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9815    0.2657   -0.0931 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0647    0.1146   -1.1668 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4486    0.5174   -0.7514 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9286   -0.2947    0.4311 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3123    0.1039    0.8519 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2894   -0.0744   -0.1887 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0650    1.6299    0.4563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1344    2.2634    0.3968 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0351    2.2109    1.0393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0538   -0.9500   -0.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3421   -1.8443   -1.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5664   -2.6976   -0.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7029    0.3787   -1.3802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6758   -0.4223    0.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2378    0.6846   -2.0955 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0691   -0.9553   -1.5115 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4794    1.6049   -0.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1649    0.2886   -1.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2720   -0.2249    1.3121 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9424   -1.3643    0.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3283    1.1662    1.1506 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6055   -0.5502    1.7060 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5578    0.8244   -0.6245 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9309   -0.7758   -0.8621 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3211    3.1605    0.8456 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
  5 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  1
  6 19  1  0
  6 20  1  0
  7 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 13 29  1  0
M  END
Download

PDB for HMDB0000446 (N-alpha-Acetyl-L-lysine)

HEADER    PROTEIN                                 20-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-20         0                                  
HETATM    1  C   UNK     0    8663.2708660.522   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8661.9388659.751   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8660.6058660.522   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8659.2728659.751   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8657.9398660.522   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0    8656.6068659.751   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0    8663.2708662.060   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0    8664.6038662.830   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8665.9398662.060   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8664.6038664.370   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0    8664.6038659.751   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0    8665.9398660.522   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    8664.6038658.212   0.000  0.00  0.00           O+0
CONECT    1    2    7   11                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7    1    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    1   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END
Download

3D PDB for HMDB0000446 (N-alpha-Acetyl-L-lysine)

COMPND    HMDB0000446
HETATM    1  C1  UNL     1      -4.287  -1.735  -0.553  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.984  -1.268  -0.079  1.00  0.00           C  
HETATM    3  O1  UNL     1      -2.431  -1.897   0.872  1.00  0.00           O  
HETATM    4  N1  UNL     1      -2.289  -0.160  -0.607  1.00  0.00           N  
HETATM    5  C3  UNL     1      -0.981   0.266  -0.093  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.065   0.115  -1.167  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.449   0.517  -0.751  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.929  -0.295   0.431  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.312   0.104   0.852  1.00  0.00           C  
HETATM   10  N2  UNL     1       4.289  -0.074  -0.189  1.00  0.00           N  
HETATM   11  C8  UNL     1      -1.065   1.630   0.456  1.00  0.00           C  
HETATM   12  O2  UNL     1      -2.134   2.263   0.397  1.00  0.00           O  
HETATM   13  O3  UNL     1       0.035   2.211   1.039  1.00  0.00           O  
HETATM   14  H1  UNL     1      -5.054  -0.950  -0.302  1.00  0.00           H  
HETATM   15  H2  UNL     1      -4.342  -1.844  -1.657  1.00  0.00           H  
HETATM   16  H3  UNL     1      -4.566  -2.698  -0.088  1.00  0.00           H  
HETATM   17  H4  UNL     1      -2.703   0.379  -1.380  1.00  0.00           H  
HETATM   18  H5  UNL     1      -0.676  -0.422   0.740  1.00  0.00           H  
HETATM   19  H6  UNL     1      -0.238   0.685  -2.095  1.00  0.00           H  
HETATM   20  H7  UNL     1       0.069  -0.955  -1.512  1.00  0.00           H  
HETATM   21  H8  UNL     1       1.479   1.605  -0.588  1.00  0.00           H  
HETATM   22  H9  UNL     1       2.165   0.289  -1.586  1.00  0.00           H  
HETATM   23  H10 UNL     1       1.272  -0.225   1.312  1.00  0.00           H  
HETATM   24  H11 UNL     1       1.942  -1.364   0.135  1.00  0.00           H  
HETATM   25  H12 UNL     1       3.328   1.166   1.151  1.00  0.00           H  
HETATM   26  H13 UNL     1       3.606  -0.550   1.706  1.00  0.00           H  
HETATM   27  H14 UNL     1       4.558   0.824  -0.625  1.00  0.00           H  
HETATM   28  H15 UNL     1       3.931  -0.776  -0.862  1.00  0.00           H  
HETATM   29  H16 UNL     1       0.321   3.160   0.846  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3    3    4
CONECT    4    5   17
CONECT    5    6   11   18
CONECT    6    7   19   20
CONECT    7    8   21   22
CONECT    8    9   23   24
CONECT    9   10   25   26
CONECT   10   27   28
CONECT   11   12   12   13
CONECT   13   29
END
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SMILES for HMDB0000446 (N-alpha-Acetyl-L-lysine)

CC(=O)N[C@@H](CCCCN)C(O)=O
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INCHI for HMDB0000446 (N-alpha-Acetyl-L-lysine)

InChI=1S/C8H16N2O3/c1-6(11)10-7(8(12)13)4-2-3-5-9/h7H,2-5,9H2,1H3,(H,10,11)(H,12,13)/t7-/m0/s1
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
(2S)-2-(Acetylamino)-6-aminohexanoic acidChEBI
N(alpha)-AcetyllysineChEBI
N-Acetyl-L-lysineChEBI
N2-Acetyl-L-lysineChEBI
N(alpha)-Acetyl-L-lysineChEBI
(2S)-2-(Acetylamino)-6-aminohexanoateGenerator
N(a)-AcetyllysineGenerator
N(Α)-acetyllysineGenerator
N(a)-Acetyl-L-lysineGenerator
N(Α)-acetyl-L-lysineGenerator
N-a-Acetyl-L-lysineGenerator
N-Α-acetyl-L-lysineGenerator
6-Amino-L-2-acetamidohexanoic acidHMDB
N2-AcetyllysineHMDB
Nα-acetyl-L-lysineHMDB
Nα-acetyllysineHMDB
Nalpha-acetyl-L-lysineHMDB
Nalpha-acetyllysineHMDB
N-a-AcetyllysineHMDB
N-Α-acetyllysineHMDB
6-Amino-L-2-acetamidohexanoateHMDB
N-Acetyl poly-L-lysineHMDB
N-Acetyl polylysineHMDB
AcetyllysineHMDB
6-Amino-2-[(1-hydroxyethylidene)amino]hexanoateHMDB
N(2)-AcetyllysineHMDB
N(alpha)-Acetyllysine, (DL)-isomerHMDB
N-alpha-AcetyllysineHMDB
N-alpha-Acetyl-L-lysineChEBI
Chemical FormulaC8H16N2O3
Average Molecular Weight188.227
Monoisotopic Molecular Weight188.116092383
IUPAC Name(2S)-6-amino-2-acetamidohexanoic acid
Traditional Namenα-acetyllysine
CAS Registry Number1946-82-3
SMILES
CC(=O)N[C@@H](CCCCN)C(O)=O
InChI Identifier
InChI=1S/C8H16N2O3/c1-6(11)10-7(8(12)13)4-2-3-5-9/h7H,2-5,9H2,1H3,(H,10,11)(H,12,13)/t7-/m0/s1
InChI KeyVEYYWZRYIYDQJM-ZETCQYMHSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-alpha amino acids
Alternative Parents
Substituents
  • N-acyl-alpha-amino acid
  • Medium-chain fatty acid
  • Amino fatty acid
  • Fatty acyl
  • Fatty acid
  • Amino acid
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary amine
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Health effect
Disposition
Biological locationSource
ProcessNot Available
Role
Biological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point256 - 258 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility8037 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility16.1 g/LALOGPS
logP-2.5ALOGPS
logP-3.2ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)3.89ChemAxon
pKa (Strongest Basic)10.21ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area92.42 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity47.25 m³·mol⁻¹ChemAxon
Polarizability19.96 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+140.49630932474
DeepCCS[M-H]-137.52430932474
DeepCCS[M-2H]-174.11430932474
DeepCCS[M+Na]+149.65230932474
AllCCS[M+H]+143.432859911
AllCCS[M+H-H2O]+139.732859911
AllCCS[M+NH4]+146.832859911
AllCCS[M+Na]+147.832859911
AllCCS[M-H]-141.532859911
AllCCS[M+Na-2H]-142.832859911
AllCCS[M+HCOO]-144.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-alpha-Acetyl-L-lysineCC(=O)N[C@@H](CCCCN)C(O)=O2570.3Standard polar33892256
N-alpha-Acetyl-L-lysineCC(=O)N[C@@H](CCCCN)C(O)=O1789.5Standard non polar33892256
N-alpha-Acetyl-L-lysineCC(=O)N[C@@H](CCCCN)C(O)=O1745.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-alpha-Acetyl-L-lysine,1TMS,isomer #1CC(=O)N[C@@H](CCCCN)C(=O)O[Si](C)(C)C1730.2Semi standard non polar33892256
N-alpha-Acetyl-L-lysine,1TMS,isomer #2CC(=O)N[C@@H](CCCCN[Si](C)(C)C)C(=O)O1847.3Semi standard non polar33892256
N-alpha-Acetyl-L-lysine,1TMS,isomer #3CC(=O)N([C@@H](CCCCN)C(=O)O)[Si](C)(C)C1725.2Semi standard non polar33892256
N-alpha-Acetyl-L-lysine,2TMS,isomer #1CC(=O)N[C@@H](CCCCN[Si](C)(C)C)C(=O)O[Si](C)(C)C1884.6Semi standard non polar33892256
N-alpha-Acetyl-L-lysine,2TMS,isomer #1CC(=O)N[C@@H](CCCCN[Si](C)(C)C)C(=O)O[Si](C)(C)C1927.0Standard non polar33892256
N-alpha-Acetyl-L-lysine,2TMS,isomer #1CC(=O)N[C@@H](CCCCN[Si](C)(C)C)C(=O)O[Si](C)(C)C2436.0Standard polar33892256
N-alpha-Acetyl-L-lysine,2TMS,isomer #2CC(=O)N([C@@H](CCCCN)C(=O)O[Si](C)(C)C)[Si](C)(C)C1744.0Semi standard non polar33892256
N-alpha-Acetyl-L-lysine,2TMS,isomer #2CC(=O)N([C@@H](CCCCN)C(=O)O[Si](C)(C)C)[Si](C)(C)C1855.7Standard non polar33892256
N-alpha-Acetyl-L-lysine,2TMS,isomer #2CC(=O)N([C@@H](CCCCN)C(=O)O[Si](C)(C)C)[Si](C)(C)C2658.7Standard polar33892256
N-alpha-Acetyl-L-lysine,2TMS,isomer #3CC(=O)N([C@@H](CCCCN[Si](C)(C)C)C(=O)O)[Si](C)(C)C1832.0Semi standard non polar33892256
N-alpha-Acetyl-L-lysine,2TMS,isomer #3CC(=O)N([C@@H](CCCCN[Si](C)(C)C)C(=O)O)[Si](C)(C)C1944.1Standard non polar33892256
N-alpha-Acetyl-L-lysine,2TMS,isomer #3CC(=O)N([C@@H](CCCCN[Si](C)(C)C)C(=O)O)[Si](C)(C)C2402.1Standard polar33892256
N-alpha-Acetyl-L-lysine,2TMS,isomer #4CC(=O)N[C@@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)C(=O)O2063.5Semi standard non polar33892256
N-alpha-Acetyl-L-lysine,2TMS,isomer #4CC(=O)N[C@@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)C(=O)O1996.9Standard non polar33892256
N-alpha-Acetyl-L-lysine,2TMS,isomer #4CC(=O)N[C@@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)C(=O)O2743.5Standard polar33892256
N-alpha-Acetyl-L-lysine,3TMS,isomer #1CC(=O)N([C@@H](CCCCN[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C1859.3Semi standard non polar33892256
N-alpha-Acetyl-L-lysine,3TMS,isomer #1CC(=O)N([C@@H](CCCCN[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C2006.8Standard non polar33892256
N-alpha-Acetyl-L-lysine,3TMS,isomer #1CC(=O)N([C@@H](CCCCN[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C2086.2Standard polar33892256
N-alpha-Acetyl-L-lysine,3TMS,isomer #2CC(=O)N[C@@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C2106.1Semi standard non polar33892256
N-alpha-Acetyl-L-lysine,3TMS,isomer #2CC(=O)N[C@@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C2031.7Standard non polar33892256
N-alpha-Acetyl-L-lysine,3TMS,isomer #2CC(=O)N[C@@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C2291.6Standard polar33892256
N-alpha-Acetyl-L-lysine,3TMS,isomer #3CC(=O)N([C@@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)C(=O)O)[Si](C)(C)C2004.8Semi standard non polar33892256
N-alpha-Acetyl-L-lysine,3TMS,isomer #3CC(=O)N([C@@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)C(=O)O)[Si](C)(C)C2048.3Standard non polar33892256
N-alpha-Acetyl-L-lysine,3TMS,isomer #3CC(=O)N([C@@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)C(=O)O)[Si](C)(C)C2303.9Standard polar33892256
N-alpha-Acetyl-L-lysine,4TMS,isomer #1CC(=O)N([C@@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C2041.6Semi standard non polar33892256
N-alpha-Acetyl-L-lysine,4TMS,isomer #1CC(=O)N([C@@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C2086.8Standard non polar33892256
N-alpha-Acetyl-L-lysine,4TMS,isomer #1CC(=O)N([C@@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C2041.8Standard polar33892256
N-alpha-Acetyl-L-lysine,1TBDMS,isomer #1CC(=O)N[C@@H](CCCCN)C(=O)O[Si](C)(C)C(C)(C)C1984.8Semi standard non polar33892256
N-alpha-Acetyl-L-lysine,1TBDMS,isomer #2CC(=O)N[C@@H](CCCCN[Si](C)(C)C(C)(C)C)C(=O)O2098.7Semi standard non polar33892256
N-alpha-Acetyl-L-lysine,1TBDMS,isomer #3CC(=O)N([C@@H](CCCCN)C(=O)O)[Si](C)(C)C(C)(C)C1974.7Semi standard non polar33892256
N-alpha-Acetyl-L-lysine,2TBDMS,isomer #1CC(=O)N[C@@H](CCCCN[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2344.9Semi standard non polar33892256
N-alpha-Acetyl-L-lysine,2TBDMS,isomer #1CC(=O)N[C@@H](CCCCN[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2300.4Standard non polar33892256
N-alpha-Acetyl-L-lysine,2TBDMS,isomer #1CC(=O)N[C@@H](CCCCN[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2510.0Standard polar33892256
N-alpha-Acetyl-L-lysine,2TBDMS,isomer #2CC(=O)N([C@@H](CCCCN)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2224.0Semi standard non polar33892256
N-alpha-Acetyl-L-lysine,2TBDMS,isomer #2CC(=O)N([C@@H](CCCCN)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2263.8Standard non polar33892256
N-alpha-Acetyl-L-lysine,2TBDMS,isomer #2CC(=O)N([C@@H](CCCCN)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2663.4Standard polar33892256
N-alpha-Acetyl-L-lysine,2TBDMS,isomer #3CC(=O)N([C@@H](CCCCN[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C2341.6Semi standard non polar33892256
N-alpha-Acetyl-L-lysine,2TBDMS,isomer #3CC(=O)N([C@@H](CCCCN[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C2309.9Standard non polar33892256
N-alpha-Acetyl-L-lysine,2TBDMS,isomer #3CC(=O)N([C@@H](CCCCN[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C2505.2Standard polar33892256
N-alpha-Acetyl-L-lysine,2TBDMS,isomer #4CC(=O)N[C@@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O2497.1Semi standard non polar33892256
N-alpha-Acetyl-L-lysine,2TBDMS,isomer #4CC(=O)N[C@@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O2347.1Standard non polar33892256
N-alpha-Acetyl-L-lysine,2TBDMS,isomer #4CC(=O)N[C@@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O2713.9Standard polar33892256
N-alpha-Acetyl-L-lysine,3TBDMS,isomer #1CC(=O)N([C@@H](CCCCN[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2551.5Semi standard non polar33892256
N-alpha-Acetyl-L-lysine,3TBDMS,isomer #1CC(=O)N([C@@H](CCCCN[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2541.4Standard non polar33892256
N-alpha-Acetyl-L-lysine,3TBDMS,isomer #1CC(=O)N([C@@H](CCCCN[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2447.8Standard polar33892256
N-alpha-Acetyl-L-lysine,3TBDMS,isomer #2CC(=O)N[C@@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2742.9Semi standard non polar33892256
N-alpha-Acetyl-L-lysine,3TBDMS,isomer #2CC(=O)N[C@@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2589.2Standard non polar33892256
N-alpha-Acetyl-L-lysine,3TBDMS,isomer #2CC(=O)N[C@@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2535.3Standard polar33892256
N-alpha-Acetyl-L-lysine,3TBDMS,isomer #3CC(=O)N([C@@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C2681.5Semi standard non polar33892256
N-alpha-Acetyl-L-lysine,3TBDMS,isomer #3CC(=O)N([C@@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C2603.4Standard non polar33892256
N-alpha-Acetyl-L-lysine,3TBDMS,isomer #3CC(=O)N([C@@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C2561.1Standard polar33892256
N-alpha-Acetyl-L-lysine,4TBDMS,isomer #1CC(=O)N([C@@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2906.4Semi standard non polar33892256
N-alpha-Acetyl-L-lysine,4TBDMS,isomer #1CC(=O)N([C@@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2807.3Standard non polar33892256
N-alpha-Acetyl-L-lysine,4TBDMS,isomer #1CC(=O)N([C@@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2491.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-alpha-Acetyl-L-lysine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-alpha-Acetyl-L-lysine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-alpha-Acetyl-L-lysine GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-alpha-Acetyl-L-lysine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-alpha-Acetyl-L-lysine GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-alpha-Acetyl-L-lysine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-alpha-Acetyl-L-lysine GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-alpha-Acetyl-L-lysine GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - N-alpha-Acetyl-L-lysine Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-003i-1900000000-1bb977fd5835c87c7d012019-03-05HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-alpha-Acetyl-L-lysine Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-001i-9200000000-08d9b5954a220181ea5f2019-03-05HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-alpha-Acetyl-L-lysine Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-001i-9000000000-9404d66c59d266164c232019-03-05HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-alpha-Acetyl-L-lysine 30V, Negative-QTOFsplash10-052b-9600000000-64d02b65a9438fd24af12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-alpha-Acetyl-L-lysine 20V, Negative-QTOFsplash10-0002-2900000000-4e4307890c5505c5aeba2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-alpha-Acetyl-L-lysine 40V, Negative-QTOFsplash10-0006-9000000000-3d476e678ca9d6df5ea42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-alpha-Acetyl-L-lysine 10V, Negative-QTOFsplash10-0002-0900000000-28b149c70053eaa89aa02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-alpha-Acetyl-L-lysine 35V, Negative-QTOFsplash10-0002-0900000000-b154acfb571fb75b00f52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-alpha-Acetyl-L-lysine 35V, Positive-QTOFsplash10-003r-2900000000-b607df4d59ad27d4f5c32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-alpha-Acetyl-L-lysine 35V, Positive-QTOFsplash10-003r-2900000000-bde2837d508c6909ec122021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-alpha-Acetyl-L-lysine 10V, Positive-QTOFsplash10-000j-0900000000-0c503af7c1fbf54b2c2c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-alpha-Acetyl-L-lysine 20V, Positive-QTOFsplash10-001i-9700000000-cecd553985bf6c4d71602021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-alpha-Acetyl-L-lysine 40V, Positive-QTOFsplash10-053r-9000000000-f705bda3174a35c518f82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-alpha-Acetyl-L-lysine 10V, Negative-QTOFsplash10-0002-0900000000-637ed07817e215db52332021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-alpha-Acetyl-L-lysine 20V, Negative-QTOFsplash10-0002-1900000000-92bf1c9bbc3af7b68c0c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-alpha-Acetyl-L-lysine 40V, Negative-QTOFsplash10-0006-9000000000-57df45c6e237a09f2c4b2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2019-03-05Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2019-03-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedBoth
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
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)FemaleNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.67 (0.48-1.15) umol/mmol creatinineNewborn (0-30 days old)Both
Normal
    • Analysis of 40 NI...
 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
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 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB112380
KNApSAcK IDC00052355
Chemspider ID83869
KEGG Compound IDC12989
BioCyc IDN-ACETYL-L-LYSINE
BiGG IDNot Available
Wikipedia LinkAcetyllysine
METLIN ID5435
PubChem Compound92907
PDB IDNot Available
ChEBI ID35704
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1265811
References
Synthesis ReferenceAkagi, Aru; Soejima, Yasuhiro; Izumiya, Nobuo. Facile syntheses of e-acyl-L-lysines and abnormal optical rotations of a-acyl-L-lysines. Kyushu Sangyo Daigaku Kogakubu Kenkyu Hokoku (1992), 29 119-24.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Van Coster RN, Gerlo EA, Giardina TG, Engelke UF, Smet JE, De Praeter CM, Meersschaut VA, De Meirleir LJ, Seneca SH, Devreese B, Leroy JG, Herga S, Perrier JP, Wevers RA, Lissens W: Aminoacylase I deficiency: a novel inborn error of metabolism. Biochem Biophys Res Commun. 2005 Dec 23;338(3):1322-6. Epub 2005 Nov 2. [PubMed:16274666 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. vd Heiden C, Brink M, de Bree PK, v Sprang FJ, Wadman SK, de Pater JM, van Biervliet JP: Familial hyperlysinaemia due to L-lysine alpha-ketoglutarate reductase deficiency: results of attempted treatment. J Inherit Metab Dis. 1978;1(3):89-94. doi: 10.1007/BF01805679. [PubMed:116084 ]