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enzymes (2) Show 2 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-08-16 22:53:57 UTC

HMDB ID

HMDB0000201

Secondary Accession Numbers

HMDB0000456
HMDB0000515
HMDB00201
HMDB00456
HMDB00515

Metabolite Identification

Common Name

L-Acetylcarnitine

Description

L-Acetylcarnitine (Acetylcarnitine or ALC or LAC) is an acetic acid ester of carnitine that facilitates the movement of acetyl-CoA into the matrices of mammalian mitochondria during the oxidation of fatty acids. Acetylcarnitine is an endogenous compound widely distributed in many tissues, including brain. Chemically, acetylcarnitine is the acetylated derivative of the amino acid L-carnitine whose function is generally correlated with regulation of energy metabolism within mitochondria. The synthesis of acetylcarnitine is catalyzed by the enzyme carnitine acetyltransferase (CAT), which is located on the inner mitochondrial membrane as well as in endoplasmic reticulum and peroxisome. CAT promotes the transfer of an acetyl group from acetyl-Coenzyme A (acetyl-CoA) to carnitine, thereby producing acetylcarnitine and free CoA (PMID: 29267192 ). After being synthetized, acetylcarnitine is transported outside mitochondria into the cytosol by the enzyme carnitine/acetylcarnitine translocase (CACT). This is a crucial metabolic reaction for beta-oxidation of fatty acids whereby acetylcarnitine facilitates the transport of acetyl-CoA across mitochondrial membranes (PMID: 29267192 ). In addition to his metabolic role, L-acetylcarnitine possesses unique neuroprotective, neuromodulatory, and neurotrophic properties. acetylcarnitine is mobile throughout the plasma membranes and can rapidly cross blood-brain barrier. Indeed, acetylcarnitine can be transported by the high-affinity sodium-dependent organic cation/transporter (OCTN2), which is functionally expressed in cells forming the blood-brain barrier (PMID: 29267192 ). A wide range of mechanisms have been proposed to explain the multiplicity of acetylcarnitine activities within nervous tissues. In particular, it has been demonstrated that acetylcarnitine modulates the activity of nerve growth factor (NGF) and enhances the expression of NGF receptors in striatum/hippocampus during development (PMID: 29267192 ). Moreover, acetylcarnitine modulates different neurotransmitter systems, including the GABAergic, dopaminergic, and cholinergic system by increasing acetyl-CoA content and choline acetyltransferase (ChAT) activity. This may play an important role in counteracting various neurodegenerative disease processes (PMID: 15363640 ). In rodent models, L-acetylcarnitine has been found to be critical for hippocampal function and to induce rapid and lasting antidepressant-like effects via epigenetic mechanisms of histone acetylation (PMID: 30061399 ). More recently, levels of acetylcarnitine have been found to be reduced in people with major depressive disorder (MDD) (PMID: 30061399 ). In contrast to the positive neurotrophic effects for L-acetylcarnitine, it has been found that high blood levels of acetylcarnitine (>12 µmol/L) can be associated with inflammation or infection. Increases in acylcarnitine levels, especially for short-chain acylcarnitines such as acetylcarnitine appear to arise from the release of these compounds from the liver during infection or periods of stress/trauma. This is done to support increased levels of fatty acid beta-oxidation, which is needed for the production and synthesis of B and T-cells (macrophages, neutrophils) to fight infections or traumatic injuries. Interestingly, those suffering from sepsis or septicemia can have very high L-acetylcarnitine levels. It has been found that those with L-acetylcarnitine levels >20 µmol/L have up to 5X greater risk of dying (PMID: 30379669 ). This likely reflects a severe dysregulation of acylcarnitine production from a dysregulated immune system or damage to the liver. Overall, levels of L-acetylcarnitine correlate with the severity of organ dysfunction, inflammation and infection in sepsis and can serve as a prognostic biomarker for mortality prediction.

Structure

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

HMDB0000201
     RDKit          3D
L-Acetylcarnitine
 32 31  0  0  0  0  0  0  0  0999 V2000
    3.6718   -2.2299    0.7700 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5033   -1.7357   -0.0054 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1533   -2.3478   -1.0551 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7586   -0.6385    0.3405 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6188   -0.1862   -0.4484 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0082    1.1382   -1.0034 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3342    2.1870   -0.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5087    3.1012    0.1946 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5314    2.2190    0.6637 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5448   -0.2556    0.4423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8370    0.0813   -0.0401 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.8462   -0.7363    0.6943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1005   -0.1767   -1.4176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2252    1.4425    0.3096 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7920   -1.6545    1.7007 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5792   -2.2831    0.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4192   -3.2785    1.0929 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5551   -0.9142   -1.2762 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9471    1.0008   -1.6280 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2688    1.4872   -1.7732 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6797    2.8772    1.4156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3292    0.2998    1.4156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6139   -1.3278    0.8098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5882   -0.5694    1.7607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8290   -0.2787    0.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7374   -1.7808    0.4213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9021    0.7011   -2.0656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1949   -0.4012   -1.5392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5994   -1.1111   -1.7486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2713    1.5228    0.6692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6062    1.7006    1.2013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1041    2.1473   -0.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  5 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 11 14  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  5 18  1  6
  6 19  1  0
  6 20  1  0
  9 21  1  0
 10 22  1  0
 10 23  1  0
 12 24  1  0
 12 25  1  0
 12 26  1  0
 13 27  1  0
 13 28  1  0
 13 29  1  0
 14 30  1  0
 14 31  1  0
 14 32  1  0
M  CHG  1  11   1
M  END


  Mrv1652303262019402D          

 14 13  0  0  0  0            999 V2000
   -6.1163   -0.1994    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.4017   -0.6130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6871   -0.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9725   -0.6130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6871    0.6256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1163    0.6256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8309    1.0364    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -7.5494    0.6235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8309    1.8620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6846    1.5297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8226   -0.6233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8226   -1.4483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1080   -1.8620    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -7.5372   -1.8620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  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
  3  5  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
M  CHG  2   7   1  13  -1
M  END
> <DATABASE_ID>
HMDB0000201

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H17NO4/c1-7(11)14-8(5-9(12)13)6-10(2,3)4/h8H,5-6H2,1-4H3/t8-/m1/s1

> <INCHI_KEY>
RDHQFKQIGNGIED-MRVPVSSYSA-N

> <FORMULA>
C9H17NO4

> <MOLECULAR_WEIGHT>
203.238

> <EXACT_MASS>
203.115758031

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
20.822976329692786

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R)-3-(acetyloxy)-4-(trimethylazaniumyl)butanoate

> <ALOGPS_LOGP>
-2.39

> <JCHEM_LOGP>
-4.4463806378050785

> <ALOGPS_LOGS>
-2.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.089406374301865

> <JCHEM_PKA_STRONGEST_BASIC>
-7.0182421930796055

> <JCHEM_POLAR_SURFACE_AREA>
66.43

> <JCHEM_REFRACTIVITY>
72.6368

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.55e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acetyl-L-carnitine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000201
     RDKit          3D
L-Acetylcarnitine
 32 31  0  0  0  0  0  0  0  0999 V2000
    3.6718   -2.2299    0.7700 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5033   -1.7357   -0.0054 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1533   -2.3478   -1.0551 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7586   -0.6385    0.3405 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6188   -0.1862   -0.4484 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0082    1.1382   -1.0034 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3342    2.1870   -0.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5087    3.1012    0.1946 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5314    2.2190    0.6637 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5448   -0.2556    0.4423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8370    0.0813   -0.0401 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.8462   -0.7363    0.6943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1005   -0.1767   -1.4176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2252    1.4425    0.3096 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7920   -1.6545    1.7007 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5792   -2.2831    0.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4192   -3.2785    1.0929 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5551   -0.9142   -1.2762 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9471    1.0008   -1.6280 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2688    1.4872   -1.7732 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6797    2.8772    1.4156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3292    0.2998    1.4156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6139   -1.3278    0.8098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5882   -0.5694    1.7607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8290   -0.2787    0.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7374   -1.7808    0.4213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9021    0.7011   -2.0656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1949   -0.4012   -1.5392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5994   -1.1111   -1.7486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2713    1.5228    0.6692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6062    1.7006    1.2013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1041    2.1473   -0.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  5 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 11 14  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  5 18  1  6
  6 19  1  0
  6 20  1  0
  9 21  1  0
 10 22  1  0
 10 23  1  0
 12 24  1  0
 12 25  1  0
 12 26  1  0
 13 27  1  0
 13 28  1  0
 13 29  1  0
 14 30  1  0
 14 31  1  0
 14 32  1  0
M  CHG  1  11   1
M  END

HEADER    PROTEIN                                 26-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAR-20         0                                  
HETATM    1  C   UNK     0     -11.417  -0.372   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0     -10.083  -1.144   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -8.749  -0.372   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.415  -1.144   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -8.749   1.168   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0     -11.417   1.168   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0     -12.751   1.935   0.000  0.00  0.00           N+1
HETATM    8  C   UNK     0     -14.092   1.164   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -12.751   3.476   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -14.345   2.855   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -12.735  -1.164   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -12.735  -2.704   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0     -11.402  -3.476   0.000  0.00  0.00           O-1
HETATM   14  O   UNK     0     -14.069  -3.476   0.000  0.00  0.00           O+0
CONECT    1    2    6   11                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    1    7                                                       
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7                                                            
CONECT   11    1   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

COMPND    HMDB0304631
HETATM    1  C1  UNL     1       3.063   1.467   1.727  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.370   0.272   1.171  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.816  -0.844   1.511  1.00  0.00           O  
HETATM    4  O2  UNL     1       1.300   0.317   0.330  1.00  0.00           O  
HETATM    5  C3  UNL     1       0.667  -0.809  -0.180  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.647  -0.953  -1.659  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.002  -1.019  -2.260  1.00  0.00           C  
HETATM    8  O3  UNL     1       3.042  -0.955  -1.563  1.00  0.00           O  
HETATM    9  O4  UNL     1       2.174  -1.155  -3.626  1.00  0.00           O1-
HETATM   10  C6  UNL     1      -0.727  -1.001   0.367  1.00  0.00           C  
HETATM   11  N1  UNL     1      -1.639   0.062   0.115  1.00  0.00           N1+
HETATM   12  C7  UNL     1      -2.345  -0.032  -1.122  1.00  0.00           C  
HETATM   13  C8  UNL     1      -1.026   1.375   0.176  1.00  0.00           C  
HETATM   14  C9  UNL     1      -2.623   0.042   1.192  1.00  0.00           C  
HETATM   15  H1  UNL     1       3.081   1.408   2.845  1.00  0.00           H  
HETATM   16  H2  UNL     1       2.646   2.414   1.369  1.00  0.00           H  
HETATM   17  H3  UNL     1       4.122   1.406   1.398  1.00  0.00           H  
HETATM   18  H4  UNL     1       1.223  -1.709   0.227  1.00  0.00           H  
HETATM   19  H5  UNL     1      -0.008  -0.227  -2.178  1.00  0.00           H  
HETATM   20  H6  UNL     1       0.179  -1.960  -1.875  1.00  0.00           H  
HETATM   21  H7  UNL     1      -1.141  -1.923  -0.130  1.00  0.00           H  
HETATM   22  H8  UNL     1      -0.724  -1.233   1.448  1.00  0.00           H  
HETATM   23  H9  UNL     1      -3.434   0.029  -0.936  1.00  0.00           H  
HETATM   24  H10 UNL     1      -2.129   0.818  -1.814  1.00  0.00           H  
HETATM   25  H11 UNL     1      -2.202  -1.026  -1.638  1.00  0.00           H  
HETATM   26  H12 UNL     1      -0.391   1.610  -0.687  1.00  0.00           H  
HETATM   27  H13 UNL     1      -1.863   2.119   0.158  1.00  0.00           H  
HETATM   28  H14 UNL     1      -0.534   1.506   1.157  1.00  0.00           H  
HETATM   29  H15 UNL     1      -3.131   1.011   1.310  1.00  0.00           H  
HETATM   30  H16 UNL     1      -3.339  -0.806   1.032  1.00  0.00           H  
HETATM   31  H17 UNL     1      -2.079  -0.203   2.135  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6   10   18
CONECT    6    7   19   20
CONECT    7    8    8    9
CONECT   10   11   21   22
CONECT   11   12   13   14
CONECT   12   23   24   25
CONECT   13   26   27   28
CONECT   14   29   30   31
END

HMDB0000201
     RDKit          3D
L-Acetylcarnitine
 32 31  0  0  0  0  0  0  0  0999 V2000
    3.6718   -2.2299    0.7700 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5033   -1.7357   -0.0054 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1533   -2.3478   -1.0551 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7586   -0.6385    0.3405 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6188   -0.1862   -0.4484 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0082    1.1382   -1.0034 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3342    2.1870   -0.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5087    3.1012    0.1946 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5314    2.2190    0.6637 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5448   -0.2556    0.4423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8370    0.0813   -0.0401 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.8462   -0.7363    0.6943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1005   -0.1767   -1.4176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2252    1.4425    0.3096 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7920   -1.6545    1.7007 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5792   -2.2831    0.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4192   -3.2785    1.0929 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5551   -0.9142   -1.2762 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9471    1.0008   -1.6280 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2688    1.4872   -1.7732 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6797    2.8772    1.4156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3292    0.2998    1.4156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6139   -1.3278    0.8098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5882   -0.5694    1.7607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8290   -0.2787    0.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7374   -1.7808    0.4213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9021    0.7011   -2.0656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1949   -0.4012   -1.5392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5994   -1.1111   -1.7486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2713    1.5228    0.6692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6062    1.7006    1.2013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1041    2.1473   -0.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  5 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 11 14  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  5 18  1  6
  6 19  1  0
  6 20  1  0
  9 21  1  0
 10 22  1  0
 10 23  1  0
 12 24  1  0
 12 25  1  0
 12 26  1  0
 13 27  1  0
 13 28  1  0
 13 29  1  0
 14 30  1  0
 14 31  1  0
 14 32  1  0
M  CHG  1  11   1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(-)-Acetylcarnitine	ChEBI
(R)-Acetylcarnitine	ChEBI
Acetyl-L-(-)-carnitine	ChEBI
Acetyl-L-carnitine	ChEBI
L-Carnitine acetyl ester	ChEBI
L-O-Acetylcarnitine	ChEBI
O-Acetyl-(R)-carnitine	ChEBI
R-Acetylcarnitine	ChEBI
L-Acetylcarnitine	ChEBI
Branigen	MeSH, HMDB
Levocarnitine acetyl	MeSH, HMDB
Acetyl carnitine	MeSH, HMDB
Carnitine, acetyl	MeSH, HMDB
Alcar	MeSH, HMDB
Acetyl L carnitine	MeSH, HMDB
Acetylcarnitine, (R)-isomer	MeSH, HMDB
Medosan	MeSH, HMDB
ALC	HMDB
3-(Acetyloxy)-4-(trimethylammonio)butanoate	ChEBI, HMDB
Acetyl-DL-carnitine	ChEBI, HMDB
Acetylcarnitine	ChEBI, HMDB
DL-O-Acetylcarnitine	ChEBI, HMDB
3-(Acetyloxy)-4-(trimethylammonio)butanoic acid	Generator, HMDB
(+-)-Acetylcarnitine	HMDB
Acetyl-carnitine	HMDB
ALCAR	HMDB
Nicetile	HMDB
O-Acetyl-L-carnitine	HMDB
O-Acetylcarnitine	HMDB
(3R)-3-Acetyloxy-4-(trimethylazaniumyl)butanoate	HMDB
C2 Carnitine	HMDB

Chemical Formula

C₉H₁₇NO₄

Average Molecular Weight

203.238

Monoisotopic Molecular Weight

203.115758031

IUPAC Name

(3R)-3-(acetyloxy)-4-(trimethylazaniumyl)butanoate

Traditional Name

acetyl-L-carnitine

CAS Registry Number

3040-38-8

SMILES

CC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C

InChI Identifier

InChI=1S/C9H17NO4/c1-7(11)14-8(5-9(12)13)6-10(2,3)4/h8H,5-6H2,1-4H3/t8-/m1/s1

InChI Key

RDHQFKQIGNGIED-MRVPVSSYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Acyl carnitines

Alternative Parents

Substituents

Acyl-carnitine
Dicarboxylic acid or derivatives
Tetraalkylammonium salt
Quaternary ammonium salt
Carboxylic acid ester
Carboxylic acid salt
Carboxylic acid derivative
Carboxylic acid
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organic salt
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

O-acetylcarnitine (CHEBI:57589 )
O-acyl-L-carnitine (CHEBI:57589 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	145 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1000000 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	-4.031 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Astarita_pos	141.7	30932474
[M+H]+	MetCCS_test_pos	142.966	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.36 g/L	ALOGPS
logP	-2.4	ALOGPS
logP	-4.4	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	4.09	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	66.43 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	72.64 m³·mol⁻¹	ChemAxon
Polarizability	20.82 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
DeepCCS	[M+H]+	149.18	30932474
DeepCCS	[M-H]-	147.058	30932474
DeepCCS	[M-2H]-	180.296	30932474
DeepCCS	[M+Na]+	155.092	30932474
AllCCS	[M+H]+	145.9	32859911
AllCCS	[M+H-H2O]+	142.5	32859911
AllCCS	[M+NH4]+	149.1	32859911
AllCCS	[M+Na]+	150.0	32859911
AllCCS	[M-H]-	153.8	32859911
AllCCS	[M+Na-2H]-	155.1	32859911
AllCCS	[M+HCOO]-	156.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
L-Acetylcarnitine	CC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C	2322.9	Standard polar	33892256
L-Acetylcarnitine	CC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C	1232.0	Standard non polar	33892256
L-Acetylcarnitine	CC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C	1468.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
L-Acetylcarnitine,1TMS,isomer #1	CC(=O)O[C@H](CC(=O)O[Si](C)(C)C)C[N+](C)(C)C	1424.0	Semi standard non polar	33892256
L-Acetylcarnitine,1TBDMS,isomer #1	CC(=O)O[C@H](CC(=O)O[Si](C)(C)C(C)(C)C)C[N+](C)(C)C	1660.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - L-Acetylcarnitine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-9100000000-c3bf4495e8c4abf714db	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Acetylcarnitine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Acetylcarnitine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Acetylcarnitine GC-MS (TBDMS_1_1) - 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 - L-Acetylcarnitine Quattro_QQQ 10V, N/A-QTOF (Annotated)	splash10-000i-9200000000-e3a84538f1dadc72bc00	2018-05-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Acetylcarnitine Quattro_QQQ 25V, N/A-QTOF (Annotated)	splash10-000i-9000000000-5d5d6858632925cf1c81	2018-05-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Acetylcarnitine Quattro_QQQ 40V, N/A-QTOF (Annotated)	splash10-001i-9000000000-b7dbd311ea9af892ad91	2018-05-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Acetylcarnitine , positive-QTOF	splash10-0pb9-3930000000-1af0468e51346890699f	2018-05-25	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Acetylcarnitine 10V, Positive-QTOF	splash10-0udi-0090000000-71230651236adb31fa6f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Acetylcarnitine 20V, Positive-QTOF	splash10-0f79-9050000000-2a63f200e23202870ebe	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Acetylcarnitine 40V, Positive-QTOF	splash10-000i-9000000000-e9262cbaff8cb4ad0ba6	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2018-05-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane
Mitochondria
Endoplasmic reticulum
Peroxisome

Biospecimen Locations

Blood
Breast Milk
Cerebrospinal Fluid (CSF)
Feces
Saliva
Urine

Tissue Locations

Brain
Neuron
Placenta
Prostate
Semen
Skeletal Muscle

Pathways

Name	SMPDB/PathBank	KEGG
Biosynthesis of unsaturated fatty acids	Not Available
Oxidation of Branched Chain Fatty Acids		Not Available
Adrenoleukodystrophy, X-linked		Not Available
Carnitine-acylcarnitine translocase deficiency		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	5.48 +/- 2.15 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	16.540 +/- 3.340 uM	Infant (0-1 year old)	Not Specified	Normal	11489939	details
Blood	Detected and Quantified	3.00-12.5 uM	Adult (>18 years old)	Both	Normal	The Metabolo...	details
Blood	Detected and Quantified	3.57 (2.91-4.48) uM	Newborn (0-30 days old)	Not Available	Normal	25754623	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	4.09 +/- 5.83 uM	Children (1-13 years old)	Both	Normal	24521011	details
Blood	Detected and Quantified	1.30 +/- 0.81 uM	Children (1-13 years old)	Both	Normal	24521011	details
Blood	Detected and Quantified	6.26 (5.14-7.83) uM	Infant (0-1 year old)	Not Available	Normal	25754623	details
Blood	Detected and Quantified	8.05(3.22) uM	Adult (>18 years old)	Both	Normal	26010610	details
Blood	Detected and Quantified	3.00-12.5 uM	Adult (>18 years old)	Both	Normal	The Metabolo...	details
Blood	Detected and Quantified	6.2 +/- 0.6 uM	Adult (>18 years old)	Male	Normal	12905800	details
Blood	Detected and Quantified	5.7 +/- 0.7 uM	Adult (>18 years old)	Female	Normal	12905800	details
Blood	Detected and Quantified	6.56 +/- 2.26 uM	Adult (>18 years old)	Both	Normal	28278231	details
Blood	Detected and Quantified	4.90 (2.48-8.62) uM	Children (1-13 years old)	Both	Normal	9034211	details
Breast Milk	Detected and Quantified	10.5 +/- 4.7 uM	Adult (>18 years old)	Female	Normal	24027187	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.322 +/- 0.148 uM	Adult (>18 years old)	Not Specified	Normal	22546835	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	26476344	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	27543620	details
Feces	Detected and Quantified	0.69 +/- 0.33 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Feces	Detected and Quantified	0.39 +/- 0.2 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Normal	27609529	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Saliva	Detected and Quantified	0.973 +/- 0.002 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Saliva	Detected and Quantified	0.843 +/- 0.441 uM	Adult (>18 years old)	Male	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	0.955 +/- 0.442 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	1.53 +/- 1.23 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	1.68 +/- 0.780 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	22727327	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	17022649	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21177801	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22932811	details
Urine	Detected and Quantified	0.38-1.86 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	32340350	details
Urine	Detected and Quantified	0.85 +/- 0.38 umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	32340350	details
Urine	Detected and Quantified	0.92 +/- 0.39 umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	32340350	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21389975	details
Urine	Detected and Quantified	4.468 +/- 3.521 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected and Quantified	2.0 (0.4-5.9) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	2.8 (0.6-7.5) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	7.2058 +/- 6.0635 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected and Quantified	1.928 +/- 0.2829 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	12905800	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	26.700 +/- 9.700 uM	Infant (0-1 year old)	Not Specified	short-chain L-3-hydroxyacyl-CoA dehydrogenase deficiency	11489939	details
Blood	Detected and Quantified	27.740 +/- 9.800 uM	Infant (0-1 year old)	Female	3-Hydroxyacyl-CoA dehydrogenase deficiency (SCHAD)	11489939	details
Blood	Detected and Quantified	26.400 +/- 9.700 uM	Infant (0-1 year old)	Not Specified	Short-chain L-3-hydroxyacyl-CoA dehydrogenase deficiency	11489939	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25105552	details
Blood	Detected and Quantified	11.9(10-40) uM	Adult (>18 years old)	Both	Sepsis	26847922	details
Blood	Detected and Quantified	2.83 +/- 4.08 uM	Children (1-13 years old)	Both	Acetaminophen overdose	24521011	details
Blood	Detected and Quantified	2.5022 (2.2864) uM	Adult (>18 years old)	Female	Pregnancy with fetus having congenital heart defect	24704061	details
Blood	Detected and Quantified	10.28(3.49) uM	Adult (>18 years old)	Both	Heart failure with preserved ejection fraction	26010610	details
Blood	Detected and Quantified	800 +/- 200 uM	Adult (>18 years old)	Both	3-Methylcrotonyl-CoA Carboxylase Deficiency	25732994	details
Blood	Detected and Quantified	0.316 (0.091-0.760) uM	Adult (>18 years old)	Both	Very long-chain acyl-CoA dehydrogenase deficiency (vLCAD)	9034211	details
Blood	Detected and Quantified	6.82 +/- 3.64 uM	Children (1-13 years old)	Both	Obesity	Metabolomics reve...	details
Blood	Detected and Quantified	6.79 +/- 2.28 uM	Children (1-13 years old)	Both	Obesity	Metabolomics reve...	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Crohns disease	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Ulcerative colitis	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Unclassified IBD	27609529	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	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	Tooth Decay	31026179	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal adenoma	27510537	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal adenoma	27510537	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	21799048	details
Urine	Detected and Quantified	9.443 +/- 12.772 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected and Quantified	6.5552 +/- 13.7484 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25105552	details
Urine	Detected and Quantified	6.3512 +/- 10.4433 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Gastroesophageal reflux disease	Analysis of 30 no...	details

Associated Disorders and Diseases

Disease References

Very Long Chain Acyl-CoA Dehydrogenase Deficiency
Costa CG, Struys EA, Bootsma A, ten Brink HJ, Dorland L, Tavares de Almeida I, Duran M, Jakobs C: Quantitative analysis of plasma acylcarnitines using gas chromatography chemical ionization mass fragmentography. J Lipid Res. 1997 Jan;38(1):173-82. [PubMed:9034211 ]
Colorectal cancer
Ni Y, Xie G, Jia W: Metabonomics of human colorectal cancer: new approaches for early diagnosis and biomarker discovery. J Proteome Res. 2014 Sep 5;13(9):3857-70. doi: 10.1021/pr500443c. Epub 2014 Aug 14. [PubMed:25105552 ] 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 ]
3-Methyl-crotonyl-glycinuria
Thomsen JA, Lund AM, Olesen JH, Mohr M, Rasmussen J: Is L-Carnitine Supplementation Beneficial in 3-Methylcrotonyl-CoA Carboxylase Deficiency? JIMD Rep. 2015;21:79-88. doi: 10.1007/8904_2014_393. Epub 2015 Mar 3. [PubMed:25732994 ]
Obesity
Simone Wahl, Christina Holzapfel, Zhonghao Yu, Michaela Breier, Ivan Kondofersky, Christiane Fuchs, Paula Singmann, Cornelia Prehn, Jerzy Adamski, Harald Grallert, Thomas Illig, Rui Wang-Sattler, Thomas Reinehr (2013). Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children. Metabolomics.
Short-chain L-3-hydroxyacyl-CoA dehydrogenase deficiency
Clayton PT, Eaton S, Aynsley-Green A, Edginton M, Hussain K, Krywawych S, Datta V, Malingre HE, Berger R, van den Berg IE: Hyperinsulinism in short-chain L-3-hydroxyacyl-CoA dehydrogenase deficiency reveals the importance of beta-oxidation in insulin secretion. J Clin Invest. 2001 Aug;108(3):457-65. [PubMed:11489939 ]
3-Hydroxyacyl-CoA dehydrogenase deficiency
Clayton PT, Eaton S, Aynsley-Green A, Edginton M, Hussain K, Krywawych S, Datta V, Malingre HE, Berger R, van den Berg IE: Hyperinsulinism in short-chain L-3-hydroxyacyl-CoA dehydrogenase deficiency reveals the importance of beta-oxidation in insulin secretion. J Clin Invest. 2001 Aug;108(3):457-65. [PubMed:11489939 ]
Sepsis
Ferrario M, Cambiaghi A, Brunelli L, Giordano S, Caironi P, Guatteri L, Raimondi F, Gattinoni L, Latini R, Masson S, Ristagno G, Pastorelli R: Mortality prediction in patients with severe septic shock: a pilot study using a target metabolomics approach. Sci Rep. 2016 Feb 5;6:20391. doi: 10.1038/srep20391. [PubMed:26847922 ]
Crohn's disease
Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Ulcerative colitis
Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
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 ]
Tooth Decay
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

201475 (Very Long Chain Acyl-CoA Dehydrogenase Deficiency)
114500 (Colorectal cancer)
210200 (3-Methyl-crotonyl-glycinuria)
601665 (Obesity)
231530 (3-Hydroxyacyl-CoA dehydrogenase deficiency)
266600 (Crohn's disease)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

DB08842

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB093666

KNApSAcK ID

C00052178

Chemspider ID

5406074

KEGG Compound ID

Not Available

BioCyc ID

O-ACETYLCARNITINE

BiGG ID

Not Available

Wikipedia Link

Acetyl-L-carnitine

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

57589

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000096

Good Scents ID

rw1654391

References

Synthesis Reference

Gu, Heng-da; Shi, Shuang; Yang, Ying; Shi, Zhao-xin; Yu, Zhan-long. Synthesis of acetyl-L-carnitine by direct acylation method. Shenyang Huagong Xueyuan Xuebao (2006), 20(2), 154-155, 160.

Material Safety Data Sheet (MSDS)

Not Available

General References

Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Sakuma T: Alteration of urinary carnitine profile induced by benzoate administration. Arch Dis Child. 1991 Jul;66(7):873-5. [PubMed:1863104 ]
Grizard G, Lombard-Vignon N, Boucher D: Changes in carnitine and acetylcarnitine in human semen during cryopreservation. Hum Reprod. 1992 Oct;7(9):1245-8. [PubMed:1479006 ]
Kamimori H, Hamashima Y, Konishi M: Determination of carnitine and saturated-acyl group carnitines in human urine by high-performance liquid chromatography with fluorescence detection. Anal Biochem. 1994 May 1;218(2):417-24. [PubMed:8074302 ]
Cooper MB, Forte CA, Jones DA: Citrate interference with the determination of acetylcarnitine: a method for its elimination. Clin Chim Acta. 1986 Sep 30;159(3):291-9. [PubMed:3769216 ]
Spagnoli A, Lucca U, Menasce G, Bandera L, Cizza G, Forloni G, Tettamanti M, Frattura L, Tiraboschi P, Comelli M, et al.: Long-term acetyl-L-carnitine treatment in Alzheimer's disease. Neurology. 1991 Nov;41(11):1726-32. [PubMed:1944900 ]
Brooks DE: Carnitine, acetylcarnitine and the activity of carnitine acyltransferases in seminal plasma and spermatozoa of men, rams and rats. J Reprod Fertil. 1979 Jul;56(2):667-73. [PubMed:480318 ]
Inoue F, Terada N, Nakajima H, Okochi M, Kodo N, Kizaki Z, Kinugasa A, Sawada T: Effect of sports activity on carnitine metabolism. Measurement of free carnitine, gamma-butyrobetaine and acylcarnitines by tandem mass spectrometry. J Chromatogr B Biomed Sci Appl. 1999 Aug 6;731(1):83-8. [PubMed:10491992 ]
Niu YJ, Jiang ZM, Shu H, Li CF, Liu W, Yao GX, Jiang J, Li JQ, Longo A: [Assay of carnitine in plasma and urine of healthy adults]. Zhongguo Yi Xue Ke Xue Yuan Xue Bao. 2002 Apr;24(2):185-7. [PubMed:12905800 ]
Siliprandi N, Di Lisa F, Pieralisi G, Ripari P, Maccari F, Menabo R, Giamberardino MA, Vecchiet L: Metabolic changes induced by maximal exercise in human subjects following L-carnitine administration. Biochim Biophys Acta. 1990 Apr 23;1034(1):17-21. [PubMed:2328258 ]
Marzo A, Cardace G, Corbelleta C, Bassani E, Morabito E, Arrigoni Martelli E: Homeostatic equilibrium of L-carnitine family before and after i.v. administration of propionyl-L-carnitine in humans, dogs and rats. Eur J Drug Metab Pharmacokinet. 1991;Spec No 3:357-63. [PubMed:1820908 ]
Novak M, Wieser PB, Buch M, Hahn P: Acetylcarnitine and free carnitine in body fluids before and after birth. Pediatr Res. 1979 Jan;13(1):10-5. [PubMed:571081 ]
Battistin L, Pizzolato G, Dam M, Da Col C, Perlotto N, Saitta B, Borsato N, Calvani M, Ferlin G: Single-photon emission computed tomography studies with 99mTc-hexamethylpropyleneamine oxime in dementia: effects of acute administration of L-acetylcarnitine. Eur Neurol. 1989;29(5):261-5. [PubMed:2792144 ]
Deufel T: Determination of L-carnitine in biological fluids and tissues. J Clin Chem Clin Biochem. 1990 May;28(5):307-11. [PubMed:2380667 ]
Minkler PE, Hoppel CL: Quantification of free carnitine, individual short- and medium-chain acylcarnitines, and total carnitine in plasma by high-performance liquid chromatography. Anal Biochem. 1993 Aug 1;212(2):510-8. [PubMed:8214594 ]
Bruno G, Scaccianoce S, Bonamini M, Patacchioli FR, Cesarino F, Grassini P, Sorrentino E, Angelucci L, Lenzi GL: Acetyl-L-carnitine in Alzheimer disease: a short-term study on CSF neurotransmitters and neuropeptides. Alzheimer Dis Assoc Disord. 1995 Fall;9(3):128-31. [PubMed:8534410 ]
Pace S, Longo A, Toon S, Rolan P, Evans AM: Pharmacokinetics of propionyl-L-carnitine in humans: evidence for saturable tubular reabsorption. Br J Clin Pharmacol. 2000 Nov;50(5):441-8. [PubMed:11069438 ]
De Rosa M, Boggia B, Amalfi B, Zarrilli S, Vita A, Colao A, Lombardi G: Correlation between seminal carnitine and functional spermatozoal characteristics in men with semen dysfunction of various origins. Drugs R D. 2005;6(1):1-9. [PubMed:15801863 ]
Zanelli SA, Solenski NJ, Rosenthal RE, Fiskum G: Mechanisms of ischemic neuroprotection by acetyl-L-carnitine. Ann N Y Acad Sci. 2005 Aug;1053:153-61. [PubMed:16179519 ]
Kuratsune H, Yamaguti K, Lindh G, Evengard B, Hagberg G, Matsumura K, Iwase M, Onoe H, Takahashi M, Machii T, Kanakura Y, Kitani T, Langstrom B, Watanabe Y: Brain regions involved in fatigue sensation: reduced acetylcarnitine uptake into the brain. Neuroimage. 2002 Nov;17(3):1256-65. [PubMed:12414265 ]
Gray SC, Devito G, Nimmo MA: Effect of active warm-up on metabolism prior to and during intense dynamic exercise. Med Sci Sports Exerc. 2002 Dec;34(12):2091-6. [PubMed:12471321 ]
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 ]
Virmani A, Binienda Z: Role of carnitine esters in brain neuropathology. Mol Aspects Med. 2004 Oct-Dec;25(5-6):533-49. doi: 10.1016/j.mam.2004.06.003. [PubMed:15363640 ]
Nasca C, Bigio B, Lee FS, Young SP, Kautz MM, Albright A, Beasley J, Millington DS, Mathe AA, Kocsis JH, Murrough JW, McEwen BS, Rasgon N: Acetyl-l-carnitine deficiency in patients with major depressive disorder. Proc Natl Acad Sci U S A. 2018 Aug 21;115(34):8627-8632. doi: 10.1073/pnas.1801609115. Epub 2018 Jul 30. [PubMed:30061399 ]
Chiechio S, Canonico PL, Grilli M: l-Acetylcarnitine: A Mechanistically Distinctive and Potentially Rapid-Acting Antidepressant Drug. Int J Mol Sci. 2017 Dec 21;19(1). pii: ijms19010011. doi: 10.3390/ijms19010011. [PubMed:29267192 ]
Chung KP, Chen GY, Chuang TY, Huang YT, Chang HT, Chen YF, Liu WL, Chen YJ, Hsu CL, Huang MT, Kuo CH, Yu CJ: Increased Plasma Acetylcarnitine in Sepsis Is Associated With Multiple Organ Dysfunction and Mortality: A Multicenter Cohort Study. Crit Care Med. 2019 Feb;47(2):210-218. doi: 10.1097/CCM.0000000000003517. [PubMed:30379669 ]
Knuplez E, Marsche G: An Updated Review of Pro- and Anti-Inflammatory Properties of Plasma Lysophosphatidylcholines in the Vascular System. Int J Mol Sci. 2020 Jun 24;21(12). pii: ijms21124501. doi: 10.3390/ijms21124501. [PubMed:32599910 ]

Enzymes

Enzyme Details

1. Carnitine O-acetyltransferase

General function:: Involved in acyltransferase activity
Specific function:: Carnitine acetylase is specific for short chain fatty acids. Carnitine acetylase seems to affect the flux through the pyruvate dehydrogenase complex. It may be involved as well in the transport of acetyl-CoA into mitochondria.
Gene Name:: CRAT
Uniprot ID:: P43155
Molecular weight:: 70875.095

Reactions

Acetyl-CoA + L-Carnitine → Coenzyme A + L-Acetylcarnitine	details

Enzyme Details

2. Mitochondrial carnitine/acylcarnitine carrier protein

General function:: Involved in transporter activity
Specific function:: Mediates the transport of acylcarnitines of different length across the mitochondrial inner membrane from the cytosol to the mitochondrial matrix for their oxidation by the mitochondrial fatty acid-oxidation pathway.
Gene Name:: SLC25A20
Uniprot ID:: O43772
Molecular weight:: 32943.46

Showing metabocard for L-Acetylcarnitine (HMDB0000201)

MOL for HMDB0000201 (L-Acetylcarnitine)

3D MOL for HMDB0000201 (L-Acetylcarnitine)

3D SDF for HMDB0000201 (L-Acetylcarnitine)

3D-SDF for HMDB0000201 (L-Acetylcarnitine)

PDB for HMDB0000201 (L-Acetylcarnitine)

3D PDB for HMDB0000201 (L-Acetylcarnitine)

SMILES for HMDB0000201 (L-Acetylcarnitine)

INCHI for HMDB0000201 (L-Acetylcarnitine)

Structure for HMDB0000201 (L-Acetylcarnitine)

3D Structure for HMDB0000201 (L-Acetylcarnitine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions