NP-MRD: Showing NP-Card for L-Acetylcarnitine (NP0000056)

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Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-08-19 20:22:31 UTC

NP-MRD ID

NP0000056

Secondary Accession Numbers

None

Natural Product 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 ).

Structure

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

NP0000056
     RDKit          3D

 31 30  0  0  0  0  0  0  0  0999 V2000
    3.9108   -1.8091    1.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6880   -1.4630    0.3104 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3362   -2.0597   -0.7369 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8603   -0.4394    0.7301 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6773   -0.0523    0.0489 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7482    1.3485   -0.4663 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8217    1.6236   -1.4182 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6769    0.8041   -1.8362 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9176    2.9190   -1.9194 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.5486   -0.2724    0.8456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8010    0.0773    0.2973 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.9793   -0.0012   -1.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1878    1.4502    0.6856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8530   -0.7607    0.9174 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7850   -1.5867    2.1622 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8069   -1.2543    0.7067 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1711   -2.8842    0.9881 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6408   -0.7395   -0.8305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2001    1.6925   -0.9246 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9061    2.0648    0.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4381    0.2988    1.8160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6167   -1.3447    1.1980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7847   -0.7526   -1.3227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1115   -0.3883   -1.6890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3830    0.9350   -1.5638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4509    2.0692   -0.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0428    1.4816    1.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3468    1.9682    1.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9445   -1.6952    0.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7877   -0.2072    1.0234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4703   -1.0221    1.9272 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
 10 21  1  0
 10 22  1  0
 12 23  1  0
 12 24  1  0
 12 25  1  0
 13 26  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
 14 31  1  0
M  CHG  2   9  -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>
NP0000056

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

NP0000056
     RDKit          3D

 31 30  0  0  0  0  0  0  0  0999 V2000
    3.9108   -1.8091    1.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6880   -1.4630    0.3104 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3362   -2.0597   -0.7369 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8603   -0.4394    0.7301 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6773   -0.0523    0.0489 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7482    1.3485   -0.4663 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8217    1.6236   -1.4182 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6769    0.8041   -1.8362 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9176    2.9190   -1.9194 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.5486   -0.2724    0.8456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8010    0.0773    0.2973 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.9793   -0.0012   -1.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1878    1.4502    0.6856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8530   -0.7607    0.9174 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7850   -1.5867    2.1622 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8069   -1.2543    0.7067 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1711   -2.8842    0.9881 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6408   -0.7395   -0.8305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2001    1.6925   -0.9246 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9061    2.0648    0.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4381    0.2988    1.8160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6167   -1.3447    1.1980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7847   -0.7526   -1.3227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1115   -0.3883   -1.6890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3830    0.9350   -1.5638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4509    2.0692   -0.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0428    1.4816    1.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3468    1.9682    1.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9445   -1.6952    0.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7877   -0.2072    1.0234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4703   -1.0221    1.9272 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
 10 21  1  0
 10 22  1  0
 12 23  1  0
 12 24  1  0
 12 25  1  0
 13 26  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
 14 31  1  0
M  CHG  2   9  -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    NP0000056
HETATM    1  C1  UNL     1       3.911  -1.809   1.076  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.688  -1.463   0.310  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.336  -2.060  -0.737  1.00  0.00           O  
HETATM    4  O2  UNL     1       1.860  -0.439   0.730  1.00  0.00           O  
HETATM    5  C3  UNL     1       0.677  -0.052   0.049  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.748   1.349  -0.466  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.822   1.624  -1.418  1.00  0.00           C  
HETATM    8  O3  UNL     1       2.677   0.804  -1.836  1.00  0.00           O  
HETATM    9  O4  UNL     1       1.918   2.919  -1.919  1.00  0.00           O1-
HETATM   10  C6  UNL     1      -0.549  -0.272   0.846  1.00  0.00           C  
HETATM   11  N1  UNL     1      -1.801   0.077   0.297  1.00  0.00           N1+
HETATM   12  C7  UNL     1      -1.979  -0.001  -1.109  1.00  0.00           C  
HETATM   13  C8  UNL     1      -2.188   1.450   0.686  1.00  0.00           C  
HETATM   14  C9  UNL     1      -2.853  -0.761   0.917  1.00  0.00           C  
HETATM   15  H1  UNL     1       3.785  -1.587   2.162  1.00  0.00           H  
HETATM   16  H2  UNL     1       4.807  -1.254   0.707  1.00  0.00           H  
HETATM   17  H3  UNL     1       4.171  -2.884   0.988  1.00  0.00           H  
HETATM   18  H4  UNL     1       0.641  -0.740  -0.830  1.00  0.00           H  
HETATM   19  H5  UNL     1      -0.200   1.693  -0.925  1.00  0.00           H  
HETATM   20  H6  UNL     1       0.906   2.065   0.397  1.00  0.00           H  
HETATM   21  H7  UNL     1      -0.438   0.299   1.816  1.00  0.00           H  
HETATM   22  H8  UNL     1      -0.617  -1.345   1.198  1.00  0.00           H  
HETATM   23  H9  UNL     1      -2.785  -0.753  -1.323  1.00  0.00           H  
HETATM   24  H10 UNL     1      -1.112  -0.388  -1.689  1.00  0.00           H  
HETATM   25  H11 UNL     1      -2.383   0.935  -1.564  1.00  0.00           H  
HETATM   26  H12 UNL     1      -2.451   2.069  -0.196  1.00  0.00           H  
HETATM   27  H13 UNL     1      -3.043   1.482   1.361  1.00  0.00           H  
HETATM   28  H14 UNL     1      -1.347   1.968   1.195  1.00  0.00           H  
HETATM   29  H15 UNL     1      -2.945  -1.695   0.344  1.00  0.00           H  
HETATM   30  H16 UNL     1      -3.788  -0.207   1.023  1.00  0.00           H  
HETATM   31  H17 UNL     1      -2.470  -1.022   1.927  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

NP0000056
     RDKit          3D

31 30  0  0  0  0  0  0  0  0999 V2000
    3.9108   -1.8091    1.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6880   -1.4630    0.3104 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3362   -2.0597   -0.7369 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8603   -0.4394    0.7301 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6773   -0.0523    0.0489 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7482    1.3485   -0.4663 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8217    1.6236   -1.4182 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6769    0.8041   -1.8362 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9176    2.9190   -1.9194 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.5486   -0.2724    0.8456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8010    0.0773    0.2973 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.9793   -0.0012   -1.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1878    1.4502    0.6856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8530   -0.7607    0.9174 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7850   -1.5867    2.1622 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8069   -1.2543    0.7067 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1711   -2.8842    0.9881 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6408   -0.7395   -0.8305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2001    1.6925   -0.9246 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9061    2.0648    0.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4381    0.2988    1.8160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6167   -1.3447    1.1980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7847   -0.7526   -1.3227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1115   -0.3883   -1.6890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3830    0.9350   -1.5638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4509    2.0692   -0.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0428    1.4816    1.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3468    1.9682    1.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9445   -1.6952    0.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7877   -0.2072    1.0234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4703   -1.0221    1.9272 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
 10 21  1  0
 10 22  1  0
 12 23  1  0
 12 24  1  0
 12 25  1  0
 13 26  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
 14 31  1  0
M  CHG  2   9  -1  11   1
M  END

View in JSmol

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

Chemical Formula

C₉H₁₇NO₄

Average Mass

203.2380 Da

Monoisotopic Mass

203.11576 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, simulated)	Varshavi.d26			2021-10-09	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Varshavi.d26			2021-10-09	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, simulated)	Varshavi.d26			2021-07-25	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Homo sapiens	LOTUS Database	35616633
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Species Where Detected

Species Name	Source	Reference
Homo sapiens (Urine)	KNApSAcK Database	22123792

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 )

Physical Properties

State

Solid

Experimental 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

Predicted 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

External Links

HMDB ID

HMDB0000201

DrugBank ID

DB08842

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Acetyl-L-carnitine

METLIN ID

Not Available

PubChem Compound

7045767

PDB ID

Not Available

ChEBI ID

57589

Good Scents ID

rw1654391

References

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 ]
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 ]
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 ]

Showing NP-Card for L-Acetylcarnitine (NP0000056)

MOL for NP0000056 (L-Acetylcarnitine)

3D MOL for NP0000056 (L-Acetylcarnitine)

3D SDF for NP0000056 (L-Acetylcarnitine)

3D-SDF for NP0000056 (L-Acetylcarnitine)

PDB for NP0000056 (L-Acetylcarnitine)

3D PDB for NP0000056 (L-Acetylcarnitine)

SMILES for NP0000056 (L-Acetylcarnitine)

INCHI for NP0000056 (L-Acetylcarnitine)

Structure for NP0000056 (L-Acetylcarnitine)

3D Structure for NP0000056 (L-Acetylcarnitine)