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Showing metabocard for DL-Acetylcarnitine (HMDB0240773)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2021-02-24 01:47:11 UTC
Update Date2022-10-24 19:44:17 UTC
HMDB IDHMDB0240773
Secondary Accession NumbersNone
Metabolite Identification
Common NameDL-Acetylcarnitine
DescriptionDL-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
Data?1658191591
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0240773 (DL-Acetylcarnitine)


  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
Download

3D MOL for HMDB0240773 (DL-Acetylcarnitine)

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
Download

3D SDF for HMDB0240773 (DL-Acetylcarnitine)


  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

$$$$
Download

3D-SDF for HMDB0240773 (DL-Acetylcarnitine)

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
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PDB for HMDB0240773 (DL-Acetylcarnitine)

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
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3D PDB for HMDB0240773 (DL-Acetylcarnitine)

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
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SMILES for HMDB0240773 (DL-Acetylcarnitine)

CC(=O)OC(CC([O-])=O)C[N+](C)(C)C
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INCHI for HMDB0240773 (DL-Acetylcarnitine)

InChI=1S/C9H17NO4/c1-7(11)14-8(5-9(12)13)6-10(2,3)4/h8H,5-6H2,1-4H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
3-(Acetyloxy)-4-(trimethylammonio)butanoateChEBI
Acetyl-DL-carnitineChEBI
AcetylcarnitineChEBI
DL-O-AcetylcarnitineChEBI
3-(Acetyloxy)-4-(trimethylammonio)butanoic acidGenerator
(+-)-AcetylcarnitineHMDB
(-)-AcetylcarnitineHMDB
(R)-AcetylcarnitineHMDB
Acetyl-carnitineHMDB
Acetyl-L-(-)-carnitineHMDB
Acetyl-L-carnitineHMDB
ALCARHMDB
L-Carnitine acetyl esterHMDB
L-O-AcetylcarnitineHMDB
Levocarnitine acetylHMDB
NicetileHMDB
O-Acetyl-L-carnitineHMDB
O-AcetylcarnitineHMDB
Acetylcarnitine, (R)-isomerHMDB
Carnitine, acetylHMDB
Acetyl L carnitineHMDB
MedosanHMDB
Sigma-tau brand OF acetyl L-carnitineHMDB
Acetyl carnitineHMDB
BranigenHMDB
Glaxo brand OF acetyl L-carnitineHMDB
Sigma tau brand OF acetyl L carnitineHMDB
Glaxo brand OF acetyl L carnitineHMDB
Chemical FormulaC9H17NO4
Average Molecular Weight203.2356
Monoisotopic Molecular Weight203.115758037
IUPAC Name3-(acetyloxy)-4-(trimethylazaniumyl)butanoate
Traditional Namealcar
CAS Registry NumberNot 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 KeyRDHQFKQIGNGIED-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentAcyl 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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Health effect
Disposition
Biological locationSource
ProcessNot Available
Role
Biological roleIndustrial application
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP-2.4ALOGPS
logP-4.4ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)4.09ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area66.43 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity72.64 m³·mol⁻¹ChemAxon
Polarizability20.88 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+147.85330932474
DeepCCS[M-H]-145.90730932474
DeepCCS[M-2H]-179.14430932474
DeepCCS[M+Na]+153.76430932474
AllCCS[M+H]+145.232859911
AllCCS[M+H-H2O]+141.732859911
AllCCS[M+NH4]+148.432859911
AllCCS[M+Na]+149.332859911
AllCCS[M-H]-152.232859911
AllCCS[M+Na-2H]-153.532859911
AllCCS[M+HCOO]-154.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DL-AcetylcarnitineCC(=O)OC(CC([O-])=O)C[N+](C)(C)C1796.0Standard polar33892256
DL-AcetylcarnitineCC(=O)OC(CC([O-])=O)C[N+](C)(C)C1113.5Standard non polar33892256
DL-AcetylcarnitineCC(=O)OC(CC([O-])=O)C[N+](C)(C)C1335.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - DL-Acetylcarnitine GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-9100000000-c3bf4495e8c4abf714db2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - DL-Acetylcarnitine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - DL-Acetylcarnitine Quattro_QQQ 10V, N/A-QTOF (Annotated)splash10-000i-9200000000-e3a84538f1dadc72bc002012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DL-Acetylcarnitine Quattro_QQQ 25V, N/A-QTOF (Annotated)splash10-000i-9000000000-5d5d6858632925cf1c812012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DL-Acetylcarnitine Quattro_QQQ 40V, N/A-QTOF (Annotated)splash10-001i-9000000000-b7dbd311ea9af892ad912012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DL-Acetylcarnitine , positive-QTOFsplash10-0pb9-3930000000-1af0468e51346890699f2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DL-Acetylcarnitine 10V, Positive-QTOFsplash10-0udi-0090000000-71230651236adb31fa6f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DL-Acetylcarnitine 20V, Positive-QTOFsplash10-0f79-9050000000-2a63f200e23202870ebe2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DL-Acetylcarnitine 40V, Positive-QTOFsplash10-000i-9000000000-e9262cbaff8cb4ad0ba62021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified11.9(10-40) uMAdult (>18 years old)BothSepsis details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease References
Sepsis
  1. 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 IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021904
KNApSAcK IDNot Available
Chemspider ID21243783
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound1
PDB IDNot Available
ChEBI ID73024
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  11. Reuter SE, Evans AM: Carnitine and acylcarnitines: pharmacokinetic, pharmacological and clinical aspects. Clin Pharmacokinet. 2012 Sep 1;51(9):553-72. doi: 10.1007/BF03261931. [PubMed:22804748 ]
  12. Bruce CR, Hoy AJ, Turner N, Watt MJ, Allen TL, Carpenter K, Cooney GJ, Febbraio MA, Kraegen EW: Overexpression of carnitine palmitoyltransferase-1 in skeletal muscle is sufficient to enhance fatty acid oxidation and improve high-fat diet-induced insulin resistance. Diabetes. 2009 Mar;58(3):550-8. doi: 10.2337/db08-1078. Epub 2008 Dec 10. [PubMed:19073774 ]
  13. Schooneman MG, Vaz FM, Houten SM, Soeters MR: Acylcarnitines: reflecting or inflicting insulin resistance? Diabetes. 2013 Jan;62(1):1-8. doi: 10.2337/db12-0466. [PubMed:23258903 ]
  14. Ahmad T, Kelly JP, McGarrah RW, Hellkamp AS, Fiuzat M, Testani JM, Wang TS, Verma A, Samsky MD, Donahue MP, Ilkayeva OR, Bowles DE, Patel CB, Milano CA, Rogers JG, Felker GM, O'Connor CM, Shah SH, Kraus WE: Prognostic Implications of Long-Chain Acylcarnitines in Heart Failure and Reversibility With Mechanical Circulatory Support. J Am Coll Cardiol. 2016 Jan 26;67(3):291-9. doi: 10.1016/j.jacc.2015.10.079. [PubMed:26796394 ]
  15. Kiykim E, Aktuglu Zeybek AC, Barut K, Zubarioglu T, Cansever MS, Alsancak S, Kasapcopur O: Screening of Free Carnitine and Acylcarnitine Status in Children With Familial Mediterranean Fever. Arch Rheumatol. 2016 Mar 10;31(2):133-138. doi: 10.5606/ArchRheumatol.2016.5696. eCollection 2016 Jun. [PubMed:29900937 ]
  16. Abu Bakar MH, Sarmidi MR: Association of cultured myotubes and fasting plasma metabolite profiles with mitochondrial dysfunction in type 2 diabetes subjects. Mol Biosyst. 2017 Aug 22;13(9):1838-1853. doi: 10.1039/c7mb00333a. [PubMed:28726959 ]
  17. Mai M, Tonjes A, Kovacs P, Stumvoll M, Fiedler GM, Leichtle AB: Serum levels of acylcarnitines are altered in prediabetic conditions. PLoS One. 2013 Dec 16;8(12):e82459. doi: 10.1371/journal.pone.0082459. eCollection 2013. [PubMed:24358186 ]
  18. Shah SH, Bain JR, Muehlbauer MJ, Stevens RD, Crosslin DR, Haynes C, Dungan J, Newby LK, Hauser ER, Ginsburg GS, Newgard CB, Kraus WE: Association of a peripheral blood metabolic profile with coronary artery disease and risk of subsequent cardiovascular events. Circ Cardiovasc Genet. 2010 Apr;3(2):207-14. doi: 10.1161/CIRCGENETICS.109.852814. Epub 2010 Feb 19. [PubMed:20173117 ]
  19. Adams SH, Hoppel CL, Lok KH, Zhao L, Wong SW, Minkler PE, Hwang DH, Newman JW, Garvey WT: Plasma acylcarnitine profiles suggest incomplete long-chain fatty acid beta-oxidation and altered tricarboxylic acid cycle activity in type 2 diabetic African-American women. J Nutr. 2009 Jun;139(6):1073-81. doi: 10.3945/jn.108.103754. Epub 2009 Apr 15. [PubMed:19369366 ]
  20. Sun Y, Kim JH, Vangipuram K, Hayes DF, Smith EML, Yeomans L, Henry NL, Stringer KA, Hertz DL: Pharmacometabolomics reveals a role for histidine, phenylalanine, and threonine in the development of paclitaxel-induced peripheral neuropathy. Breast Cancer Res Treat. 2018 Oct;171(3):657-666. doi: 10.1007/s10549-018-4862-3. Epub 2018 Jun 26. [PubMed:29946863 ]
  21. Ciborowski M, Adamska E, Rusak M, Godzien J, Wilk J, Citko A, Bauer W, Gorska M, Kretowski A: CE-MS-based serum fingerprinting to track evolution of type 2 diabetes mellitus. Electrophoresis. 2015 Sep;36(18):2286-2293. doi: 10.1002/elps.201500021. Epub 2015 Jun 26. [PubMed:25964024 ]
  22. Ueland T, Svardal A, Oie E, Askevold ET, Nymoen SH, Bjorndal B, Dahl CP, Gullestad L, Berge RK, Aukrust P: Disturbed carnitine regulation in chronic heart failure--increased plasma levels of palmitoyl-carnitine are associated with poor prognosis. Int J Cardiol. 2013 Sep 1;167(5):1892-9. doi: 10.1016/j.ijcard.2012.04.150. Epub 2012 May 22. [PubMed:22622056 ]
  23. Ohtani Y, Ohyanagi K, Yamamoto S, Matsuda I: Secondary carnitine deficiency in hyperammonemic attacks of ornithine transcarbamylase deficiency. J Pediatr. 1988 Mar;112(3):409-14. doi: 10.1016/s0022-3476(88)80321-4. [PubMed:3346778 ]
  24. Wang-Sattler R, Yu Z, Herder C, Messias AC, Floegel A, He Y, Heim K, Campillos M, Holzapfel C, Thorand B, Grallert H, Xu T, Bader E, Huth C, Mittelstrass K, Doring A, Meisinger C, Gieger C, Prehn C, Roemisch-Margl W, Carstensen M, Xie L, Yamanaka-Okumura H, Xing G, Ceglarek U, Thiery J, Giani G, Lickert H, Lin X, Li Y, Boeing H, Joost HG, de Angelis MH, Rathmann W, Suhre K, Prokisch H, Peters A, Meitinger T, Roden M, Wichmann HE, Pischon T, Adamski J, Illig T: Novel biomarkers for pre-diabetes identified by metabolomics. Mol Syst Biol. 2012;8:615. doi: 10.1038/msb.2012.43. [PubMed:23010998 ]
  25. Adal E, Koyuncu G, Aydin A, Celebi A, Kavunoglu G, Cam H: Asymptomatic cardiomyopathy in children and adolescents with type 1 diabetes mellitus: association of echocardiographic indicators with duration of diabetes mellitus and metabolic parameters. J Pediatr Endocrinol Metab. 2006 May;19(5):713-26. doi: 10.1515/jpem.2006.19.5.713. [PubMed:16789638 ]
  26. Steiner N, Muller U, Hajek R, Sevcikova S, Borjan B, Johrer K, Gobel G, Pircher A, Gunsilius E: The metabolomic plasma profile of myeloma patients is considerably different from healthy subjects and reveals potential new therapeutic targets. PLoS One. 2018 Aug 10;13(8):e0202045. doi: 10.1371/journal.pone.0202045. eCollection 2018. [PubMed:30096165 ]
  27. Famularo G, Moretti S, Marcellini S, Trinchieri V, Tzantzoglou S, Santini G, Longo A, De Simone C: Acetyl-carnitine deficiency in AIDS patients with neurotoxicity on treatment with antiretroviral nucleoside analogues. AIDS. 1997 Feb;11(2):185-90. doi: 10.1097/00002030-199702000-00008. [PubMed:9030365 ]
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