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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2021-02-24 01:47:11 UTC

Update Date

2022-10-24 19:44:17 UTC

HMDB ID

HMDB0240773

Secondary Accession Numbers

None

Metabolite Identification

Common Name

DL-Acetylcarnitine

Description

DL-Acetylcarnitine is an acylcarnitine. More specifically, it is an acetic acid ester of carnitine. Acylcarnitines were first discovered more than 70 year ago (PMID: 13825279 ). It is believed that there are more than 1000 types of acylcarnitines in the human body. The general role of acylcarnitines is to transport acyl-groups (organic acids and fatty acids) from the cytoplasm into the mitochondria so that they can be broken down to produce energy. This process is known as beta-oxidation. According to a recent review (PMID: 35710135 ), acylcarnitines (ACs) can be classified into 9 different categories depending on the type and size of their acyl-group: 1) short-chain ACs; 2) medium-chain ACs; 3) long-chain ACs; 4) very long-chain ACs; 5) hydroxy ACs; 6) branched chain ACs; 7) unsaturated ACs; 8) dicarboxylic ACs and 9) miscellaneous ACs. Short-chain ACs have acyl-groups with two to five carbons (C2-C5), medium-chain ACs have acyl-groups with six to thirteen carbons (C6-C13), long-chain ACs have acyl-groups with fourteen to twenty once carbons (C14-C21) and very long-chain ACs have acyl groups with more than 22 carbons. DL-Acetylcarnitine is therefore classified as a long chain AC. As a long-chain acylcarnitine DL-Acetylcarnitine is generally formed through esterification with long-chain fatty acids obtained from the diet. The main function of most long-chain acylcarnitines is to ensure long chain fatty acid transport into the mitochondria (PMID: 22804748 ). Altered levels of long-chain acylcarnitines can serve as useful markers for inherited disorders of long-chain fatty acid metabolism. In particular DL-Acetylcarnitine is elevated in the blood or plasma of individuals with very long chain acyl-CoA dehydrogenase deficiency (PMID: 9034211 ), colorectal cancer (PMID: 25105552 ), short-chain 3-hydroxyacyl-CoA dehydrogenase deficiency (PMID: 11489939 ), paclitaxel induced neuropathy (PMID: 29946863 ), type 2 diabetes Mellitus (PMID: 28726959 ; PMID: 25964024 , PMID: 28726959 , PMID: 19369366 , PMID: 24358186 ), chronic heart failure (PMID: 22622056 ), ornithine transcarbamylase (PMID: 3346778 ), pre-diabetes (PMID: 23010998 , PMID: 24358186 ), type 1 diabetes mellitus (PMID: 16789638 ), methylmalonic acidemia (PMID: 8214594 ), myeloma (PMID: 30096165 ), and diastolic heart failure (PMID: 26010610 ). It is also decreased in the blood or plasma of individuals with 3-methyl-crotonyl-glycinuria (PMID: 25732994 ), antiviral drug induced neuropathy (PMID: 9030365 , PMID: 11364244 ), Alzheimer Disease (PMID: 27196316 ), major depressive disorder (PMID: 30061399 ), carnitine palmitoyltransferase 2 deficiency (PMID: 20543534 ), Familial Mediterranean Fever (PMID: 29900937 ), chronic fatigue syndrome (PMID: 9854142 ), methylmalonic acidemia (PMID: 15164354 ), hepatocellular carcinoma (PMID: 26976432 , PMID: 31662827 ), and coronary artery disease (PMID: 20173117 ). DL-Acetylcarnitine is elevated in the urine of individuals with colorectal cancer (25105552 ), uterine fibroids (32590215), heart failure (8070147), diabetes mellitus (10221661), and hepatocellular carcinoma (24923488). It is also decreased in the urine of individuals with carnitine palmitoyltransferase 2 deficiency (20543534 ). Carnitine palmitoyltransferase I (CPT I, EC:2.3.1.21) is involved in the synthesis of long-chain acylcarnitines (more than C12) on the mitochondrial outer membrane. Elevated serum/plasma levels of long-chain acylcarnitines are not only markers for incomplete FA oxidation but also are indicators of altered carbohydrate and lipid metabolism. High serum concentrations of long-chain acylcarnitines in the postprandial or fed state are markers of insulin resistance and arise from insulin's inability to inhibit CPT-1-dependent fatty acid metabolism in muscles and the heart (PMID: 19073774 ). Increased intracellular content of long-chain acylcarnitines is thought to serve as a feedback inhibition mechanism of insulin action (PMID: 23258903 ). In healthy subjects, increased concentrations of insulin effectively inhibits long-chain acylcarnitine production. Several studies have also found increased levels of circulating long-chain acylcarnitines in chronic heart failure patients (PMID: 26796394 ). The study of acylcarnitines is an active area of research and it is likely that many novel acylcarnitines will be discovered in the coming years. It is also likely that many novel roles in health and disease will be uncovered. An excellent review of the current state of knowledge for acylcarnitines is available (PMID: 35710135 ).

Structure

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

HMDB0240773
     RDKit          3D
DL-Acetylcarnitine
 31 30  0  0  0  0  0  0  0  0999 V2000
    4.0692   -1.4074    0.2730 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6685   -1.0865    0.7223 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1878   -1.5882    1.7551 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9306   -0.2172   -0.0468 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5945    0.1444    0.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5262    1.6434    0.3434 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4726    2.2071    1.3163 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1923    1.4253    1.9819 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5962    3.5884    1.5237 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.3404   -0.4382   -0.7340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7200   -0.1837   -0.5245 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.4407   -1.2808   -1.2107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2089    1.0310   -1.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1870   -0.2315    0.8263 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7472   -0.5728    0.5046 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4108   -2.3148    0.8216 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0816   -1.6298   -0.7967 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3819   -0.3304    1.2889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5062    2.0311    0.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8341    2.0820   -0.6549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1767   -1.5448   -0.6993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0653   -0.1132   -1.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4452   -1.4040   -0.8050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4102   -1.0400   -2.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8346   -2.2006   -1.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0243    0.8352   -1.8956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7016    1.7203   -0.4076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4578    1.6102   -1.6727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4583   -1.2727    1.1121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5533    0.2054    1.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1627    0.3328    0.8587 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  0
  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


  Mrv1652310061800322D          

 14 13  0  0  0  0            999 V2000
   -0.6039    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2211   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -0.8250    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -1.3184    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.0000    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.1105    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0  0  0  0
  8  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  5  1  0  0  0  0
 10  2  1  0  0  0  0
 10  3  1  0  0  0  0
 10  4  1  0  0  0  0
 10  6  1  0  0  0  0
 11  7  2  0  0  0  0
 12  9  2  0  0  0  0
 13  9  1  0  0  0  0
 14  7  1  0  0  0  0
 14  8  1  0  0  0  0
M  CHG  2  10   1  13  -1
M  END
> <DATABASE_ID>
HMDB0240773

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)OC(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

> <INCHI_KEY>
RDHQFKQIGNGIED-UHFFFAOYSA-N

> <FORMULA>
C9H17NO4

> <MOLECULAR_WEIGHT>
203.2356

> <EXACT_MASS>
203.115758037

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
20.882992325723116

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
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>
72.63680000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.55e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
alcar

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0240773
     RDKit          3D
DL-Acetylcarnitine
 31 30  0  0  0  0  0  0  0  0999 V2000
    4.0692   -1.4074    0.2730 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6685   -1.0865    0.7223 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1878   -1.5882    1.7551 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9306   -0.2172   -0.0468 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5945    0.1444    0.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5262    1.6434    0.3434 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4726    2.2071    1.3163 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1923    1.4253    1.9819 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5962    3.5884    1.5237 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.3404   -0.4382   -0.7340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7200   -0.1837   -0.5245 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.4407   -1.2808   -1.2107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2089    1.0310   -1.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1870   -0.2315    0.8263 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7472   -0.5728    0.5046 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4108   -2.3148    0.8216 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0816   -1.6298   -0.7967 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3819   -0.3304    1.2889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5062    2.0311    0.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8341    2.0820   -0.6549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1767   -1.5448   -0.6993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0653   -0.1132   -1.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4452   -1.4040   -0.8050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4102   -1.0400   -2.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8346   -2.2006   -1.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0243    0.8352   -1.8956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7016    1.7203   -0.4076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4578    1.6102   -1.6727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4583   -1.2727    1.1121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5533    0.2054    1.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1627    0.3328    0.8587 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  0
  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                                 06-OCT-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-OCT-18         0                                  
HETATM    1  C   UNK     0      -1.127   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.127  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.413  -1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.127   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.127   3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.206   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -1.127  -1.540   0.000  0.00  0.00           N+1
HETATM   11  O   UNK     0      -2.461   2.310   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.874   2.310   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       4.207  -0.000   0.000  0.00  0.00           O-1
HETATM   14  O   UNK     0       0.206   2.310   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2   10                                                            
CONECT    3   10                                                            
CONECT    4   10                                                            
CONECT    5    8    9                                                       
CONECT    6    8   10                                                       
CONECT    7    1   11   14                                                  
CONECT    8    5    6   14                                                  
CONECT    9    5   12   13                                                  
CONECT   10    2    3    4    6                                             
CONECT   11    7                                                            
CONECT   12    9                                                            
CONECT   13    9                                                            
CONECT   14    7    8                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

COMPND    HMDB0240773
HETATM    1  C1  UNL     1       4.069  -1.407   0.273  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.668  -1.087   0.722  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.188  -1.588   1.755  1.00  0.00           O  
HETATM    4  O2  UNL     1       1.931  -0.217  -0.047  1.00  0.00           O  
HETATM    5  C3  UNL     1       0.595   0.144   0.318  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.526   1.643   0.343  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.473   2.207   1.316  1.00  0.00           C  
HETATM    8  O3  UNL     1       2.192   1.425   1.982  1.00  0.00           O  
HETATM    9  O4  UNL     1       1.596   3.588   1.524  1.00  0.00           O1-
HETATM   10  C6  UNL     1      -0.340  -0.438  -0.734  1.00  0.00           C  
HETATM   11  N1  UNL     1      -1.720  -0.184  -0.525  1.00  0.00           N1+
HETATM   12  C7  UNL     1      -2.441  -1.281  -1.211  1.00  0.00           C  
HETATM   13  C8  UNL     1      -2.209   1.031  -1.138  1.00  0.00           C  
HETATM   14  C9  UNL     1      -2.187  -0.232   0.826  1.00  0.00           C  
HETATM   15  H1  UNL     1       4.747  -0.573   0.505  1.00  0.00           H  
HETATM   16  H2  UNL     1       4.411  -2.315   0.822  1.00  0.00           H  
HETATM   17  H3  UNL     1       4.082  -1.630  -0.797  1.00  0.00           H  
HETATM   18  H4  UNL     1       0.382  -0.330   1.289  1.00  0.00           H  
HETATM   19  H5  UNL     1      -0.506   2.031   0.476  1.00  0.00           H  
HETATM   20  H6  UNL     1       0.834   2.082  -0.655  1.00  0.00           H  
HETATM   21  H7  UNL     1      -0.177  -1.545  -0.699  1.00  0.00           H  
HETATM   22  H8  UNL     1      -0.065  -0.113  -1.749  1.00  0.00           H  
HETATM   23  H9  UNL     1      -3.445  -1.404  -0.805  1.00  0.00           H  
HETATM   24  H10 UNL     1      -2.410  -1.040  -2.294  1.00  0.00           H  
HETATM   25  H11 UNL     1      -1.835  -2.201  -1.079  1.00  0.00           H  
HETATM   26  H12 UNL     1      -3.024   0.835  -1.896  1.00  0.00           H  
HETATM   27  H13 UNL     1      -2.702   1.720  -0.408  1.00  0.00           H  
HETATM   28  H14 UNL     1      -1.458   1.610  -1.673  1.00  0.00           H  
HETATM   29  H15 UNL     1      -2.458  -1.273   1.112  1.00  0.00           H  
HETATM   30  H16 UNL     1      -1.553   0.205   1.587  1.00  0.00           H  
HETATM   31  H17 UNL     1      -3.163   0.333   0.859  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

HMDB0240773
     RDKit          3D
DL-Acetylcarnitine
 31 30  0  0  0  0  0  0  0  0999 V2000
    4.0692   -1.4074    0.2730 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6685   -1.0865    0.7223 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1878   -1.5882    1.7551 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9306   -0.2172   -0.0468 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5945    0.1444    0.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5262    1.6434    0.3434 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4726    2.2071    1.3163 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1923    1.4253    1.9819 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5962    3.5884    1.5237 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.3404   -0.4382   -0.7340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7200   -0.1837   -0.5245 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.4407   -1.2808   -1.2107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2089    1.0310   -1.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1870   -0.2315    0.8263 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7472   -0.5728    0.5046 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4108   -2.3148    0.8216 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0816   -1.6298   -0.7967 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3819   -0.3304    1.2889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5062    2.0311    0.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8341    2.0820   -0.6549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1767   -1.5448   -0.6993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0653   -0.1132   -1.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4452   -1.4040   -0.8050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4102   -1.0400   -2.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8346   -2.2006   -1.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0243    0.8352   -1.8956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7016    1.7203   -0.4076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4578    1.6102   -1.6727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4583   -1.2727    1.1121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5533    0.2054    1.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1627    0.3328    0.8587 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  0
  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 View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-(Acetyloxy)-4-(trimethylammonio)butanoate	ChEBI
Acetyl-DL-carnitine	ChEBI
Acetylcarnitine	ChEBI
DL-O-Acetylcarnitine	ChEBI
3-(Acetyloxy)-4-(trimethylammonio)butanoic acid	Generator
(+-)-Acetylcarnitine	HMDB
(-)-Acetylcarnitine	HMDB
(R)-Acetylcarnitine	HMDB
Acetyl-carnitine	HMDB
Acetyl-L-(-)-carnitine	HMDB
Acetyl-L-carnitine	HMDB
ALCAR	HMDB
L-Carnitine acetyl ester	HMDB
L-O-Acetylcarnitine	HMDB
Levocarnitine acetyl	HMDB
Nicetile	HMDB
O-Acetyl-L-carnitine	HMDB
O-Acetylcarnitine	HMDB
Acetylcarnitine, (R)-isomer	HMDB
Carnitine, acetyl	HMDB
Acetyl L carnitine	HMDB
Medosan	HMDB
Sigma-tau brand OF acetyl L-carnitine	HMDB
Acetyl carnitine	HMDB
Branigen	HMDB
Glaxo brand OF acetyl L-carnitine	HMDB
Sigma tau brand OF acetyl L carnitine	HMDB
Glaxo brand OF acetyl L carnitine	HMDB

Chemical Formula

C₉H₁₇NO₄

Average Molecular Weight

203.2356

Monoisotopic Molecular Weight

203.115758037

IUPAC Name

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

Traditional Name

alcar

CAS Registry Number

Not Available

SMILES

CC(=O)OC(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

InChI Key

RDHQFKQIGNGIED-UHFFFAOYSA-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-acylcarnitine (CHEBI:73024 )
an <i>O</i>-acyl-L-carnitine (O-ACETYLCARNITINE )

Ontology

Physiological effect

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 26847922)

Cell

All cells and tissues (PMID: 35710135)

Excreta

Biofluid or Excreta

Urine (PMID: 35710135)

Cellular substructure

Cytoplasm (PMID: 35710135)
Mitochondrion matrix (PMID: 35710135)

Organelle

Peroxisome (PMID: 35710135)

Source

Exogenous

Exogenous (HMDB: HMDB0240773)

Endogenous

Endogenous (HMDB: HMDB0240773)

Process

Not Available

Role

Biological role

Energy source (PMID: 35710135)

Industrial application

Pharmaceutical industry

Biomarker

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
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	20.88 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]+	147.853	30932474
DeepCCS	[M-H]-	145.907	30932474
DeepCCS	[M-2H]-	179.144	30932474
DeepCCS	[M+Na]+	153.764	30932474
AllCCS	[M+H]+	145.2	32859911
AllCCS	[M+H-H2O]+	141.7	32859911
AllCCS	[M+NH4]+	148.4	32859911
AllCCS	[M+Na]+	149.3	32859911
AllCCS	[M-H]-	152.2	32859911
AllCCS	[M+Na-2H]-	153.5	32859911
AllCCS	[M+HCOO]-	154.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	9.3997 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	6.99 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	565.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	232.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	88.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	159.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	46.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	245.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	274.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	764.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	772.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	54.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1238.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	185.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	195.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	512.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	367.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	112.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
DL-Acetylcarnitine	CC(=O)OC(CC([O-])=O)C[N+](C)(C)C	1796.0	Standard polar	33892256
DL-Acetylcarnitine	CC(=O)OC(CC([O-])=O)C[N+](C)(C)C	1113.5	Standard non polar	33892256
DL-Acetylcarnitine	CC(=O)OC(CC([O-])=O)C[N+](C)(C)C	1335.2	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 - DL-Acetylcarnitine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-9100000000-c3bf4495e8c4abf714db	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - DL-Acetylcarnitine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - DL-Acetylcarnitine Quattro_QQQ 10V, N/A-QTOF (Annotated)	splash10-000i-9200000000-e3a84538f1dadc72bc00	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - DL-Acetylcarnitine Quattro_QQQ 25V, N/A-QTOF (Annotated)	splash10-000i-9000000000-5d5d6858632925cf1c81	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - DL-Acetylcarnitine Quattro_QQQ 40V, N/A-QTOF (Annotated)	splash10-001i-9000000000-b7dbd311ea9af892ad91	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - DL-Acetylcarnitine , positive-QTOF	splash10-0pb9-3930000000-1af0468e51346890699f	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - DL-Acetylcarnitine 10V, Positive-QTOF	splash10-0udi-0090000000-71230651236adb31fa6f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - DL-Acetylcarnitine 20V, Positive-QTOF	splash10-0f79-9050000000-2a63f200e23202870ebe	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - DL-Acetylcarnitine 40V, Positive-QTOF	splash10-000i-9000000000-e9262cbaff8cb4ad0ba6	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	11.9(10-40) uM	Adult (>18 years old)	Both	Sepsis	26847922	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

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 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021904

KNApSAcK ID

Not Available

Chemspider ID

21243783

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

PDB ID

Not Available

ChEBI ID

73024

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
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 ]
Vernez L, Wenk M, Krahenbuhl S: Determination of carnitine and acylcarnitines in plasma by high-performance liquid chromatography/electrospray ionization ion trap tandem mass spectrometry. Rapid Commun Mass Spectrom. 2004;18(11):1233-8. [PubMed:15164354 ]
Kuratsune H, Yamaguti K, Lindh G, Evengard B, Takahashi M, Machii T, Matsumura K, Takaishi J, Kawata S, Langstrom B, Kanakura Y, Kitani T, Watanabe Y: Low levels of serum acylcarnitine in chronic fatigue syndrome and chronic hepatitis type C, but not seen in other diseases. Int J Mol Med. 1998 Jul;2(1):51-6. [PubMed:9854142 ]
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 ]
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 ]
Zordoky BN, Sung MM, Ezekowitz J, Mandal R, Han B, Bjorndahl TC, Bouatra S, Anderson T, Oudit GY, Wishart DS, Dyck JR: Metabolomic fingerprint of heart failure with preserved ejection fraction. PLoS One. 2015 May 26;10(5):e0124844. doi: 10.1371/journal.pone.0124844. eCollection 2015. [PubMed:26010610 ]
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 ]
Sud M, Fahy E, Cotter D, Brown A, Dennis EA, Glass CK, Merrill AH Jr, Murphy RC, Raetz CR, Russell DW, Subramaniam S: LMSD: LIPID MAPS structure database. Nucleic Acids Res. 2007 Jan;35(Database issue):D527-32. doi: 10.1093/nar/gkl838. Epub 2006 Nov 10. [PubMed:17098933 ]
FRITZ IB: Action of carnitine on long chain fatty acid oxidation by liver. Am J Physiol. 1959 Aug;197:297-304. doi: 10.1152/ajplegacy.1959.197.2.297. [PubMed:13825279 ]
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Showing metabocard for DL-Acetylcarnitine (HMDB0240773)

MOL for HMDB0240773 (DL-Acetylcarnitine)

3D MOL for HMDB0240773 (DL-Acetylcarnitine)

3D SDF for HMDB0240773 (DL-Acetylcarnitine)

3D-SDF for HMDB0240773 (DL-Acetylcarnitine)

PDB for HMDB0240773 (DL-Acetylcarnitine)

3D PDB for HMDB0240773 (DL-Acetylcarnitine)

SMILES for HMDB0240773 (DL-Acetylcarnitine)

INCHI for HMDB0240773 (DL-Acetylcarnitine)

Structure for HMDB0240773 (DL-Acetylcarnitine)

3D Structure for HMDB0240773 (DL-Acetylcarnitine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra