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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:00 UTC

HMDB ID

HMDB0000222

Secondary Accession Numbers

HMDB0000846
HMDB00222
HMDB00846

Metabolite Identification

Common Name

Palmitoylcarnitine

Description

L-Palmitoylcarnitine or hexadecanoylcarnitine is an acylcarnitine. It is technically a long-chain acyl fatty acid derivative ester of carnitine which facilitates the transfer of long-chain fatty acids from cytoplasm into mitochondria during the oxidation of fatty acids. 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. As part of this process, palmitic acid is first transported into the cell via the long-chain fatty acid transport protein 1 (FATP1). Once inside the cell it undergoes a reaction to form an acyl-CoA derivative called palmitoyl-CoA. This reaction is facilitated by the Long-chain fatty-acid CoA ligase 1 protein, which adds a CoA moiety to appropriate acyl groups. Many acyl-CoA groups will then further react with other zwitterionic compounds such as carnitine (to form acylcarnitines) and amino acids (to form acyl amides). The carnitine needed to form acylcarnitines inside the cell is transported into the cell by the organic cation/carnitine transporter 2. In forming an acylcarnitine derivative, palmitoyl-CoA reacts with L-carnitine to form palmitoylcarnitine. This reaction is catalyzed by carnitine O-palmitoyltransferase. This enzyme resides in the mitochondrial outer membrane. While this reaction takes place, the palmitoylcarnitine is moved into the mitochondrial intermembrane space. Following the reaction, the newly synthesized acylcarnitine is transported into the mitochondrial matrix by a mitochondrial carnitine/acylcarnitine carrier protein found in the mitochondrial inner membrane. Once in the matrix, palmitoylcarnitine can react with the carnitine O-palmitoyltransferase 2 enzyme found in the mitochondrial inner membrane to once again form palmitoyl-CoA and L-carnitine. Palmitoyl-CoA then enters into the mitochondrial beta-oxidation pathway to form aceytl-CoA. Acetyl-CoA can go on to enter the TCA cycle, or it can react with L-carnitine to form L-acetylcarnitine in a reaction catalyzed by Carnitine O-acetyltransferase. This reaction can occur in both directions, and L-acetylcarnitine and CoA can react to form acetyl-CoA and L-carnitine in certain circumstances. Finally, acetyl-CoA in the cytosol can be catalyzed by acetyl-CoA carboxylase 1 to form malonyl-CoA, which inhibits the action of carnitine O-palmitoyltransferase 1, thereby preventing palmitoylcarnitine from forming and thereby preventing it from being transported into the mitochondria. L-Palmitoylcarnitine has been also reported to change the activity of certain proteins and to stimulate the activity of caspases 3, 7, and 8. Interestingly, the level of this long-chain acylcarnitine has been shown to increase during apoptosis. Palmitoylcarnitine has also been reported to diminish the binding of phorbol esters (protein kinase C activators) and the autophosphorylation of the enzyme. Some of the physicochemical properties of palmitoylcarnitine may help to explain the need for coenzyme A-carnitine-coenzyme A acyl exchange during mitochondrial fatty acid import. The amphiphilic character of palmitoylcarnitine may also explain its proposed involvement in the pathogenesis of myocardial ischemia. L-Palmitoylcarnitine accumulates in ischemic myocardium and potentially contributes to myocardial damage through alterations in membrane molecular dynamics. This is a mechanism through which could play an important role in ischemic injury (PMID: 2540838 , 15363641 , 8706815 ). Palmitoylcarnitine is characteristically elevated in late-onset carnitine palmitoyltransferase II deficiency (OMIM: 255110 ).

Structure

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

  Mrv1652311191918112D          

 28 27  0  0  0  0            999 V2000
 9998.993110004.0773    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.707410003.6638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.421710004.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.136010003.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.850310004.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.564410003.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.278810004.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.993110003.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.706810004.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.422810003.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.136710004.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.852610003.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.566510004.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.280410003.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.994310004.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.710210003.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.424110004.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.138010003.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.421710004.9020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.993110004.9020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.278810005.3126    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
 9997.560410004.8999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.278810006.1379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.425210005.8057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.287010003.6535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.287010002.8289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.001110002.4154    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
 9997.572710002.4154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 20  1  6  0  0  0
  1 25  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 19  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
M  CHG  2  21   1  27  -1
M  END

HMDB0000222
     RDKit          3D
Palmitoylcarnitine
 74 73  0  0  0  0  0  0  0  0999 V2000
    7.9893   -3.2449   -1.8730 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1619   -2.7742   -0.4549 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9792   -1.8916   -0.0213 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6991   -2.6596   -0.0890 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4984   -1.7783    0.3153 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6613   -1.2955    1.6916 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5422   -0.5562    2.2886 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0733    0.6976    1.6892 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4372    0.6922    0.3533 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0181    2.1134   -0.0411 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0537    2.6779    0.9285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1910    1.8482    1.0621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1817    2.4783    2.0245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6115    3.8605    1.5549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2590    3.7247    0.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4318    2.8187    0.3838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4259    3.1716    1.0417 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3707    1.5708   -0.1950 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4607    0.6293   -0.0550 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9848   -0.5168    0.8110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8341   -1.2206    0.2660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3595   -0.8680   -0.8389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2410   -2.2680    0.9233 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0024    0.2608   -1.3806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1321   -0.6178   -1.4079 N   0  0  0  0  0  4  0  0  0  0  0  0
   -5.8801   -2.0074   -1.2520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1666   -0.1588   -0.4878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7394   -0.4449   -2.7501 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6161   -4.3113   -1.8731 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9710   -3.2090   -2.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2511   -2.5957   -2.3655 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1063   -2.1916   -0.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1745   -3.6497    0.2220 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1830   -1.5358    1.0149 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9653   -1.0140   -0.6905 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4944   -2.9596   -1.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6944   -3.5716    0.5263 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5977   -2.3639    0.1490 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5897   -0.9156   -0.4040 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5691   -0.5973    1.6933 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9931   -2.1398    2.3921 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6311   -1.2553    2.3799 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7835   -0.3938    3.4097 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3639    1.1771    2.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9038    1.4772    1.6301 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4585    0.1101    0.3978 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0174    0.3249   -0.4951 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9930    2.6875   -0.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6502    2.1211   -1.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7945    3.7164    0.5437 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4507    2.8421    1.9458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6458    1.5348    0.1121 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1185    0.8917    1.5885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6972    2.5896    2.9971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0841    1.8527    2.0425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7888    4.5966    1.5491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3589    4.2143    2.2934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5685    3.3655   -0.5708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6520    4.7228   -0.0849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2290    1.1552    0.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7445   -0.0270    1.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7861   -1.2313    1.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4771   -2.2250    1.5681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3514    1.2293   -1.8561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2014   -0.0805   -2.1009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4321   -2.5730   -2.0687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2913   -2.4547   -0.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8209   -2.2587   -1.4478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0411   -0.8398   -0.6267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8083   -0.1307    0.5410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4464    0.8641   -0.7992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8648   -0.4901   -2.6832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4215   -1.2528   -3.4378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5009    0.5532   -3.1550 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 19 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 25 28  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  0
  7 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  0
  9 47  1  0
 10 48  1  0
 10 49  1  0
 11 50  1  0
 11 51  1  0
 12 52  1  0
 12 53  1  0
 13 54  1  0
 13 55  1  0
 14 56  1  0
 14 57  1  0
 15 58  1  0
 15 59  1  0
 19 60  1  1
 20 61  1  0
 20 62  1  0
 23 63  1  0
 24 64  1  0
 24 65  1  0
 26 66  1  0
 26 67  1  0
 26 68  1  0
 27 69  1  0
 27 70  1  0
 27 71  1  0
 28 72  1  0
 28 73  1  0
 28 74  1  0
M  CHG  1  25   1
M  END

  Mrv1652311191918112D          

 28 27  0  0  0  0            999 V2000
 9998.993110004.0773    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.707410003.6638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.421710004.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.136010003.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.850310004.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.564410003.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.278810004.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.993110003.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.706810004.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.422810003.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.136710004.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.852610003.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.566510004.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.280410003.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.994310004.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.710210003.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.424110004.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.138010003.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.421710004.9020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.993110004.9020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.278810005.3126    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
 9997.560410004.8999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.278810006.1379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.425210005.8057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.287010003.6535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.287010002.8289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.001110002.4154    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
 9997.572710002.4154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 20  1  6  0  0  0
  1 25  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 19  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
M  CHG  2  21   1  27  -1
M  END
> <DATABASE_ID>
HMDB0000222

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C23H45NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(27)28-21(19-22(25)26)20-24(2,3)4/h21H,5-20H2,1-4H3/t21-/m1/s1

> <INCHI_KEY>
XOMRRQXKHMYMOC-OAQYLSRUSA-N

> <FORMULA>
C23H45NO4

> <MOLECULAR_WEIGHT>
399.6077

> <EXACT_MASS>
399.334858933

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
50.35273260304272

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
1.77

> <JCHEM_LOGP>
2.033547854194921

> <ALOGPS_LOGS>
-7.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.216763902737658

> <JCHEM_PKA_STRONGEST_BASIC>
-7.057186892022333

> <JCHEM_POLAR_SURFACE_AREA>
66.43

> <JCHEM_REFRACTIVITY>
137.07670000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
20

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.20e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
palmitoylcarnitine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000222
     RDKit          3D
Palmitoylcarnitine
 74 73  0  0  0  0  0  0  0  0999 V2000
    7.9893   -3.2449   -1.8730 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1619   -2.7742   -0.4549 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9792   -1.8916   -0.0213 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6991   -2.6596   -0.0890 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4984   -1.7783    0.3153 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6613   -1.2955    1.6916 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5422   -0.5562    2.2886 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0733    0.6976    1.6892 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4372    0.6922    0.3533 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0181    2.1134   -0.0411 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0537    2.6779    0.9285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1910    1.8482    1.0621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1817    2.4783    2.0245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6115    3.8605    1.5549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2590    3.7247    0.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4318    2.8187    0.3838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4259    3.1716    1.0417 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3707    1.5708   -0.1950 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4607    0.6293   -0.0550 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9848   -0.5168    0.8110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8341   -1.2206    0.2660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3595   -0.8680   -0.8389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2410   -2.2680    0.9233 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0024    0.2608   -1.3806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1321   -0.6178   -1.4079 N   0  0  0  0  0  4  0  0  0  0  0  0
   -5.8801   -2.0074   -1.2520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1666   -0.1588   -0.4878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7394   -0.4449   -2.7501 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6161   -4.3113   -1.8731 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9710   -3.2090   -2.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2511   -2.5957   -2.3655 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1063   -2.1916   -0.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1745   -3.6497    0.2220 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1830   -1.5358    1.0149 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9653   -1.0140   -0.6905 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4944   -2.9596   -1.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6944   -3.5716    0.5263 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5977   -2.3639    0.1490 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5897   -0.9156   -0.4040 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5691   -0.5973    1.6933 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9931   -2.1398    2.3921 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6311   -1.2553    2.3799 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7835   -0.3938    3.4097 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3639    1.1771    2.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9038    1.4772    1.6301 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4585    0.1101    0.3978 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0174    0.3249   -0.4951 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9930    2.6875   -0.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6502    2.1211   -1.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7945    3.7164    0.5437 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4507    2.8421    1.9458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6458    1.5348    0.1121 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1185    0.8917    1.5885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6972    2.5896    2.9971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0841    1.8527    2.0425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7888    4.5966    1.5491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3589    4.2143    2.2934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5685    3.3655   -0.5708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6520    4.7228   -0.0849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2290    1.1552    0.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7445   -0.0270    1.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7861   -1.2313    1.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4771   -2.2250    1.5681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3514    1.2293   -1.8561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2014   -0.0805   -2.1009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4321   -2.5730   -2.0687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2913   -2.4547   -0.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8209   -2.2587   -1.4478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0411   -0.8398   -0.6267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8083   -0.1307    0.5410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4464    0.8641   -0.7992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8648   -0.4901   -2.6832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4215   -1.2528   -3.4378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5009    0.5532   -3.1550 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 19 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 25 28  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  0
  7 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  0
  9 47  1  0
 10 48  1  0
 10 49  1  0
 11 50  1  0
 11 51  1  0
 12 52  1  0
 12 53  1  0
 13 54  1  0
 13 55  1  0
 14 56  1  0
 14 57  1  0
 15 58  1  0
 15 59  1  0
 19 60  1  1
 20 61  1  0
 20 62  1  0
 23 63  1  0
 24 64  1  0
 24 65  1  0
 26 66  1  0
 26 67  1  0
 26 68  1  0
 27 69  1  0
 27 70  1  0
 27 71  1  0
 28 72  1  0
 28 73  1  0
 28 74  1  0
M  CHG  1  25   1
M  END

HEADER    PROTEIN                                 19-NOV-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-NOV-19         0                                  
HETATM    1  C   UNK     0    8664.7878674.278   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8666.1218673.506   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8667.4548674.278   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8668.7878673.506   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8670.1218674.278   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8671.4548673.506   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8672.7878674.278   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8674.1208673.506   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8675.4538674.278   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8676.7898673.506   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8678.1228674.278   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8679.4588673.506   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8680.7918674.278   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8682.1238673.506   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8683.4568674.278   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8684.7928673.506   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8686.1258674.278   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8687.4588673.506   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0    8667.4548675.817   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0    8664.7878675.817   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0    8663.4548676.584   0.000  0.00  0.00           N+1
HETATM   22  C   UNK     0    8662.1138675.813   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8663.4548678.124   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8661.8608677.504   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8663.4698673.487   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8663.4698671.947   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0    8664.8028671.175   0.000  0.00  0.00           O-1
HETATM   28  O   UNK     0    8662.1368671.175   0.000  0.00  0.00           O+0
CONECT    1    2   20   25                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19    3                                                            
CONECT   20    1   21                                                       
CONECT   21   20   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21                                                            
CONECT   25    1   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   54    0
END

COMPND    HMDB0000222
HETATM    1  C1  UNL     1       7.989  -3.245  -1.873  1.00  0.00           C  
HETATM    2  C2  UNL     1       8.162  -2.774  -0.455  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.979  -1.892  -0.021  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.699  -2.660  -0.089  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.498  -1.778   0.315  1.00  0.00           C  
HETATM    6  C6  UNL     1       4.661  -1.295   1.692  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.542  -0.556   2.289  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.073   0.698   1.689  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.437   0.692   0.353  1.00  0.00           C  
HETATM   10  C10 UNL     1       2.018   2.113  -0.041  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.054   2.678   0.928  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.191   1.848   1.062  1.00  0.00           C  
HETATM   13  C13 UNL     1      -1.182   2.478   2.024  1.00  0.00           C  
HETATM   14  C14 UNL     1      -1.611   3.861   1.555  1.00  0.00           C  
HETATM   15  C15 UNL     1      -2.259   3.725   0.188  1.00  0.00           C  
HETATM   16  C16 UNL     1      -3.432   2.819   0.384  1.00  0.00           C  
HETATM   17  O1  UNL     1      -4.426   3.172   1.042  1.00  0.00           O  
HETATM   18  O2  UNL     1      -3.371   1.571  -0.195  1.00  0.00           O  
HETATM   19  C17 UNL     1      -4.461   0.629  -0.055  1.00  0.00           C  
HETATM   20  C18 UNL     1      -3.985  -0.517   0.811  1.00  0.00           C  
HETATM   21  C19 UNL     1      -2.834  -1.221   0.266  1.00  0.00           C  
HETATM   22  O3  UNL     1      -2.359  -0.868  -0.839  1.00  0.00           O  
HETATM   23  O4  UNL     1      -2.241  -2.268   0.923  1.00  0.00           O  
HETATM   24  C20 UNL     1      -5.002   0.261  -1.381  1.00  0.00           C  
HETATM   25  N1  UNL     1      -6.132  -0.618  -1.408  1.00  0.00           N1+
HETATM   26  C21 UNL     1      -5.880  -2.007  -1.252  1.00  0.00           C  
HETATM   27  C22 UNL     1      -7.167  -0.159  -0.488  1.00  0.00           C  
HETATM   28  C23 UNL     1      -6.739  -0.445  -2.750  1.00  0.00           C  
HETATM   29  H1  UNL     1       7.616  -4.311  -1.873  1.00  0.00           H  
HETATM   30  H2  UNL     1       8.971  -3.209  -2.420  1.00  0.00           H  
HETATM   31  H3  UNL     1       7.251  -2.596  -2.365  1.00  0.00           H  
HETATM   32  H4  UNL     1       9.106  -2.192  -0.352  1.00  0.00           H  
HETATM   33  H5  UNL     1       8.174  -3.650   0.222  1.00  0.00           H  
HETATM   34  H6  UNL     1       7.183  -1.536   1.015  1.00  0.00           H  
HETATM   35  H7  UNL     1       6.965  -1.014  -0.690  1.00  0.00           H  
HETATM   36  H8  UNL     1       5.494  -2.960  -1.135  1.00  0.00           H  
HETATM   37  H9  UNL     1       5.694  -3.572   0.526  1.00  0.00           H  
HETATM   38  H10 UNL     1       3.598  -2.364   0.149  1.00  0.00           H  
HETATM   39  H11 UNL     1       4.590  -0.916  -0.404  1.00  0.00           H  
HETATM   40  H12 UNL     1       5.569  -0.597   1.693  1.00  0.00           H  
HETATM   41  H13 UNL     1       4.993  -2.140   2.392  1.00  0.00           H  
HETATM   42  H14 UNL     1       2.631  -1.255   2.380  1.00  0.00           H  
HETATM   43  H15 UNL     1       3.783  -0.394   3.410  1.00  0.00           H  
HETATM   44  H16 UNL     1       2.364   1.177   2.456  1.00  0.00           H  
HETATM   45  H17 UNL     1       3.904   1.477   1.630  1.00  0.00           H  
HETATM   46  H18 UNL     1       1.458   0.110   0.398  1.00  0.00           H  
HETATM   47  H19 UNL     1       3.017   0.325  -0.495  1.00  0.00           H  
HETATM   48  H20 UNL     1       2.993   2.687  -0.033  1.00  0.00           H  
HETATM   49  H21 UNL     1       1.650   2.121  -1.080  1.00  0.00           H  
HETATM   50  H22 UNL     1       0.795   3.716   0.544  1.00  0.00           H  
HETATM   51  H23 UNL     1       1.451   2.842   1.946  1.00  0.00           H  
HETATM   52  H24 UNL     1      -0.646   1.535   0.112  1.00  0.00           H  
HETATM   53  H25 UNL     1       0.118   0.892   1.589  1.00  0.00           H  
HETATM   54  H26 UNL     1      -0.697   2.590   2.997  1.00  0.00           H  
HETATM   55  H27 UNL     1      -2.084   1.853   2.042  1.00  0.00           H  
HETATM   56  H28 UNL     1      -0.789   4.597   1.549  1.00  0.00           H  
HETATM   57  H29 UNL     1      -2.359   4.214   2.293  1.00  0.00           H  
HETATM   58  H30 UNL     1      -1.568   3.366  -0.571  1.00  0.00           H  
HETATM   59  H31 UNL     1      -2.652   4.723  -0.085  1.00  0.00           H  
HETATM   60  H32 UNL     1      -5.229   1.155   0.537  1.00  0.00           H  
HETATM   61  H33 UNL     1      -3.745  -0.027   1.807  1.00  0.00           H  
HETATM   62  H34 UNL     1      -4.786  -1.231   1.054  1.00  0.00           H  
HETATM   63  H35 UNL     1      -1.477  -2.225   1.568  1.00  0.00           H  
HETATM   64  H36 UNL     1      -5.351   1.229  -1.856  1.00  0.00           H  
HETATM   65  H37 UNL     1      -4.201  -0.081  -2.101  1.00  0.00           H  
HETATM   66  H38 UNL     1      -6.432  -2.573  -2.069  1.00  0.00           H  
HETATM   67  H39 UNL     1      -6.291  -2.455  -0.320  1.00  0.00           H  
HETATM   68  H40 UNL     1      -4.821  -2.259  -1.448  1.00  0.00           H  
HETATM   69  H41 UNL     1      -8.041  -0.840  -0.627  1.00  0.00           H  
HETATM   70  H42 UNL     1      -6.808  -0.131   0.541  1.00  0.00           H  
HETATM   71  H43 UNL     1      -7.446   0.864  -0.799  1.00  0.00           H  
HETATM   72  H44 UNL     1      -7.865  -0.490  -2.683  1.00  0.00           H  
HETATM   73  H45 UNL     1      -6.422  -1.253  -3.438  1.00  0.00           H  
HETATM   74  H46 UNL     1      -6.501   0.553  -3.155  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3   32   33
CONECT    3    4   34   35
CONECT    4    5   36   37
CONECT    5    6   38   39
CONECT    6    7   40   41
CONECT    7    8   42   43
CONECT    8    9   44   45
CONECT    9   10   46   47
CONECT   10   11   48   49
CONECT   11   12   50   51
CONECT   12   13   52   53
CONECT   13   14   54   55
CONECT   14   15   56   57
CONECT   15   16   58   59
CONECT   16   17   17   18
CONECT   18   19
CONECT   19   20   24   60
CONECT   20   21   61   62
CONECT   21   22   22   23
CONECT   23   63
CONECT   24   25   64   65
CONECT   25   26   27   28
CONECT   26   66   67   68
CONECT   27   69   70   71
CONECT   28   72   73   74
END

HMDB0000222
     RDKit          3D
Palmitoylcarnitine
 74 73  0  0  0  0  0  0  0  0999 V2000
    7.9893   -3.2449   -1.8730 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1619   -2.7742   -0.4549 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9792   -1.8916   -0.0213 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6991   -2.6596   -0.0890 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4984   -1.7783    0.3153 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6613   -1.2955    1.6916 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5422   -0.5562    2.2886 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0733    0.6976    1.6892 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4372    0.6922    0.3533 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0181    2.1134   -0.0411 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0537    2.6779    0.9285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1910    1.8482    1.0621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1817    2.4783    2.0245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6115    3.8605    1.5549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2590    3.7247    0.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4318    2.8187    0.3838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4259    3.1716    1.0417 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3707    1.5708   -0.1950 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4607    0.6293   -0.0550 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9848   -0.5168    0.8110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8341   -1.2206    0.2660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3595   -0.8680   -0.8389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2410   -2.2680    0.9233 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0024    0.2608   -1.3806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1321   -0.6178   -1.4079 N   0  0  0  0  0  4  0  0  0  0  0  0
   -5.8801   -2.0074   -1.2520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1666   -0.1588   -0.4878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7394   -0.4449   -2.7501 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6161   -4.3113   -1.8731 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9710   -3.2090   -2.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2511   -2.5957   -2.3655 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1063   -2.1916   -0.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1745   -3.6497    0.2220 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1830   -1.5358    1.0149 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9653   -1.0140   -0.6905 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4944   -2.9596   -1.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6944   -3.5716    0.5263 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5977   -2.3639    0.1490 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5897   -0.9156   -0.4040 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5691   -0.5973    1.6933 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9931   -2.1398    2.3921 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6311   -1.2553    2.3799 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7835   -0.3938    3.4097 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3639    1.1771    2.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9038    1.4772    1.6301 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4585    0.1101    0.3978 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0174    0.3249   -0.4951 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9930    2.6875   -0.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6502    2.1211   -1.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7945    3.7164    0.5437 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4507    2.8421    1.9458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6458    1.5348    0.1121 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1185    0.8917    1.5885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6972    2.5896    2.9971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0841    1.8527    2.0425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7888    4.5966    1.5491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3589    4.2143    2.2934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5685    3.3655   -0.5708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6520    4.7228   -0.0849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2290    1.1552    0.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7445   -0.0270    1.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7861   -1.2313    1.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4771   -2.2250    1.5681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3514    1.2293   -1.8561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2014   -0.0805   -2.1009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4321   -2.5730   -2.0687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2913   -2.4547   -0.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8209   -2.2587   -1.4478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0411   -0.8398   -0.6267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8083   -0.1307    0.5410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4464    0.8641   -0.7992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8648   -0.4901   -2.6832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4215   -1.2528   -3.4378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5009    0.5532   -3.1550 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 19 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 25 28  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  0
  7 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  0
  9 47  1  0
 10 48  1  0
 10 49  1  0
 11 50  1  0
 11 51  1  0
 12 52  1  0
 12 53  1  0
 13 54  1  0
 13 55  1  0
 14 56  1  0
 14 57  1  0
 15 58  1  0
 15 59  1  0
 19 60  1  1
 20 61  1  0
 20 62  1  0
 23 63  1  0
 24 64  1  0
 24 65  1  0
 26 66  1  0
 26 67  1  0
 26 68  1  0
 27 69  1  0
 27 70  1  0
 27 71  1  0
 28 72  1  0
 28 73  1  0
 28 74  1  0
M  CHG  1  25   1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3R)-3-(Hexadecanoyloxy)-4-(trimethylazaniumyl)butanoate	ChEBI
(3R)-3-Palmitoyloxy-4-(trimethylammonio)butanoate	ChEBI
Hexadecanoyl-L-carnitine	ChEBI
Hexadecanoylcarnitine	ChEBI
Hexadecenoyl carnitine	ChEBI
L-Carnitine palmitoyl ester	ChEBI
O-Hexadecanoyl-(R)-carnitine	ChEBI
O-Hexadecanoyl-R-carnitine	ChEBI
Palmitoyl-L-carnitine	ChEBI
Palmitoylcarnitine	ChEBI
(3R)-3-(Hexadecanoyloxy)-4-(trimethylazaniumyl)butanoic acid	Generator
(3R)-3-Palmitoyloxy-4-(trimethylammonio)butanoic acid	Generator
(+)-Palmitoylcarnitine	HMDB
3-Carboxy-N,N,N-trimethyl-2-[(1-oxohexadecyl)oxy]-1-propanaminium	HMDB
L(-)-Palmitylcarnitine	HMDB
L-Palmitoyl-L-carnitine	HMDB
Palmitoyl-(-)-carnitine	HMDB
Palmityl-L-carnitine	HMDB
Palmitylcarnitine	HMDB
(2R)-Palmitoylcarnitine	HMDB
C16 Carnitine	HMDB
L-Palmitoylcarnitine	HMDB

Chemical Formula

C₂₃H₄₆NO₄

Average Molecular Weight

400.623

Monoisotopic Molecular Weight

400.342135385

IUPAC Name

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

Traditional Name

palmitoylcarnitine

CAS Registry Number

2364-67-2

SMILES

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

InChI Identifier

InChI=1S/C23H45NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(27)28-21(19-22(25)26)20-24(2,3)4/h21H,5-20H2,1-4H3/p+1/t21-/m1/s1

InChI Key

XOMRRQXKHMYMOC-OAQYLSRUSA-O

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-acyl-L-carnitine (CHEBI:17490 )
O-palmitoylcarnitine (CHEBI:17490 )
Fatty acyl carnitines (C02990 )
Fatty acyl carnitines (LMFA07070004 )

Ontology

Physiological effect

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 16425363)
Saliva (HMDB: HMDB0000222)

Cellular substructure

Organelle

Mitochondrion (HMDB: HMDB0000222)
Peroxisome (PMID: 35710135)

Organ

Placenta (HMDB: HMDB0000222)

Excreta

Biofluid or Excreta

Urine (PMID: 12482618)
Feces (PMID: 23384618)

Cell

All cells and tissues (PMID: 35710135)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000222)

Source

Endogenous

Endogenous (HMDB: HMDB0000222)

Animal

Animal (HMDB: HMDB0000222)

Exogenous

Food

Food (HMDB: HMDB0000222)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Exogenous (HMDB: HMDB0000222)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0000222)
Fatty Acid Metabolism (HMDB: HMDB0000222)
Fatty Acid Metabolism (PathBank: SMP0002361)

Disease pathway

Lipid metabolism pathway (HMDB: HMDB0000222)

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0000222)

Cellular process

Cell signaling (HMDB: HMDB0000222)

Biochemical process

Lipid transport (HMDB: HMDB0000222)

Role

Physical Properties

State

Solid

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
Water Solubility	1.2e-05 g/L	ALOGPS
logP	1.77	ALOGPS
logP	2.03	ChemAxon
logS	-7.6	ALOGPS
pKa (Strongest Acidic)	4.22	ChemAxon
pKa (Strongest Basic)	-7.1	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	20	ChemAxon
Refractivity	137.08 m³·mol⁻¹	ChemAxon
Polarizability	50.35 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]+	214.767	30932474
DeepCCS	[M-H]-	210.748	30932474
DeepCCS	[M-2H]-	247.291	30932474
DeepCCS	[M+Na]+	223.582	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Palmitoylcarnitine	CCCCCCCCCCCCCCCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C	3731.4	Standard polar	33892256
Palmitoylcarnitine	CCCCCCCCCCCCCCCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C	2561.0	Standard non polar	33892256
Palmitoylcarnitine	CCCCCCCCCCCCCCCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C	2785.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Palmitoylcarnitine,1TMS,isomer #1	CCCCCCCCCCCCCCCC(=O)O[C@H](CC(=O)O[Si](C)(C)C)C[N+](C)(C)C	2795.6	Semi standard non polar	33892256
Palmitoylcarnitine,1TBDMS,isomer #1	CCCCCCCCCCCCCCCC(=O)O[C@H](CC(=O)O[Si](C)(C)C(C)(C)C)C[N+](C)(C)C	3032.8	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 - Palmitoylcarnitine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-9220000000-890219021b84f6894540	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Palmitoylcarnitine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Palmitoylcarnitine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Palmitoylcarnitine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Palmitoylcarnitine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Palmitoylcarnitine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0udi-1000900000-109f35c9819eb5eed7b7	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Palmitoylcarnitine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-000i-9000000000-9d6bb14eddb4cfa8341a	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Palmitoylcarnitine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-000i-9000000000-87b1d0debe4e0cb7bd31	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Palmitoylcarnitine Linear Ion Trap , negative-QTOF	splash10-014i-0139500000-21c36c851939b94d4523	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Palmitoylcarnitine Linear Ion Trap , negative-QTOF	splash10-014i-0029600000-69ebe292c2ce42c8d810	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Palmitoylcarnitine Linear Ion Trap , positive-QTOF	splash10-0f6x-0139600000-197944fd1aa4ac44bdd2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Palmitoylcarnitine Linear Ion Trap , positive-QTOF	splash10-0uxr-0000613900-006582b143e5906e51cc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Palmitoylcarnitine Linear Ion Trap , positive-QTOF	splash10-0uxr-0000614900-14a5d773f652b71671fb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Palmitoylcarnitine Linear Ion Trap , positive-QTOF	splash10-0f6x-0139600000-b0528be9c13e412551af	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Palmitoylcarnitine 10V, Positive-QTOF	splash10-0udi-0000900000-b54b0a7f2164f15f15f2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Palmitoylcarnitine 20V, Positive-QTOF	splash10-0f79-9000500000-d7434e08a3e0942fa2e9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Palmitoylcarnitine 40V, Positive-QTOF	splash10-000i-9000000000-e9262cbaff8cb4ad0ba6	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane
Mitochondria

Biospecimen Locations

Blood
Feces
Saliva
Urine

Tissue Locations

Placenta

Pathways

Name	SMPDB/PathBank	KEGG
Fatty acid Metabolism
Ethylmalonic Encephalopathy		Not Available
Glutaric Aciduria Type I		Not Available
Short Chain Acyl CoA Dehydrogenase Deficiency (SCAD Deficiency)		Not Available
Carnitine palmitoyl transferase deficiency (I)		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.153 (0.073-0.227) uM	Children (1-13 years old)	Both	Normal	9034211	details
Blood	Detected and Quantified	0.113 +/- 0.006 uM	Adult (>18 years old)	Both	Normal	16425363	details
Blood	Detected and Quantified	0.050-0.180 uM	Adult (>18 years old)	Both	Normal	Molecular You	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	0.15 +/- 0.17 uM	Children (1-13 years old)	Both	Normal	24521011	details
Blood	Detected and Quantified	0.06 +/- 0.04 uM	Children (1-13 years old)	Both	Normal	24521011	details
Blood	Detected and Quantified	0.11 +/- 0.03 uM	Adult (>18 years old)	Both	Normal	28278231	details
Blood	Detected and Quantified	0.12(0.03) uM	Adult (>18 years old)	Both	Normal	26010610	details
Blood	Detected and Quantified	0.050-0.180 uM	Adult (>18 years old)	Both	Normal	Molecular You	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	23384618	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected and Quantified	0.36 +/- 0.27 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected and Quantified	0.22 +/- 0.07 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Saliva	Detected and Quantified	0.034 +/- 0.012 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.01-0.06 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	32340350	details
Urine	Detected and Quantified	0.01(0.01-0.07) umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	32340350	details
Urine	Detected and Quantified	0.01(0.01-0.03) umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	32340350	details
Urine	Detected and Quantified	0.0022 (0.0020-0.0030) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	0.006 +/- 0.0018 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected and Quantified	0.5 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	12482618	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	1.909 (1.012-2.233) uM	Adult (>18 years old)	Both	Very long-chain acyl-CoA dehydrogenase deficiency (vLCAD)	9034211	details
Blood	Detected and Quantified	0.097 +/- 0.006 uM	Adult (>18 years old)	Both	Celiac disease	16425363	details
Blood	Detected and Quantified	0.13 +/- 0.09 uM	Children (1-13 years old)	Both	Acetaminophen overdose	24521011	details
Blood	Detected and Quantified	0.046 (0.0375) uM	Adult (>18 years old)	Female	Pregnancy with fetus having congenital heart defect	24704061	details
Blood	Detected and Quantified	0.14(0.04) uM	Adult (>18 years old)	Both	Heart failure with preserved ejection fraction	26010610	details
Blood	Detected and Quantified	0.096 +/- 0.032 uM	Children (1-13 years old)	Both	Obesity	Metabolomics reve...	details
Blood	Detected and Quantified	0.101 +/- 0.026 uM	Children (1-13 years old)	Both	Obesity	Metabolomics reve...	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	liver cirrhosis	23384618	details
Urine	Detected and Quantified	0.0046 +/- 0.0018 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected and Quantified	0.0064 +/- 0.0047 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Gastroesophageal reflux disease	Analysis of 30 no...	details

Associated Disorders and Diseases

Disease References

Celiac disease
Bene J, Komlosi K, Gasztonyi B, Juhasz M, Tulassay Z, Melegh B: Plasma carnitine ester profile in adult celiac disease patients maintained on long-term gluten free diet. World J Gastroenterol. 2005 Nov 14;11(42):6671-5. [PubMed:16425363 ]
Very Long Chain Acyl-CoA Dehydrogenase Deficiency
Costa CG, Struys EA, Bootsma A, ten Brink HJ, Dorland L, Tavares de Almeida I, Duran M, Jakobs C: Quantitative analysis of plasma acylcarnitines using gas chromatography chemical ionization mass fragmentography. J Lipid Res. 1997 Jan;38(1):173-82. [PubMed:9034211 ]
Obesity
Simone Wahl, Christina Holzapfel, Zhonghao Yu, Michaela Breier, Ivan Kondofersky, Christiane Fuchs, Paula Singmann, Cornelia Prehn, Jerzy Adamski, Harald Grallert, Thomas Illig, Rui Wang-Sattler, Thomas Reinehr (2013). Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children. Metabolomics.
Cirrhosis
Huang HJ, Zhang AY, Cao HC, Lu HF, Wang BH, Xie Q, Xu W, Li LJ: Metabolomic analyses of faeces reveals malabsorption in cirrhotic patients. Dig Liver Dis. 2013 Aug;45(8):677-82. doi: 10.1016/j.dld.2013.01.001. Epub 2013 Feb 4. [PubMed:23384618 ]
Colorectal cancer
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

212750 (Celiac disease)
201475 (Very Long Chain Acyl-CoA Dehydrogenase Deficiency)
601665 (Obesity)
114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021910

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

17490

Food Biomarker Ontology

Not Available

VMH ID

PMTCRN

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Norum, Kaare R. Palmityl coenzyme A-carnitine palmityltransferase. Purification from calf-liver mitochondria and some properties of the enzyme. Biochimica et Biophysica Acta, Specialized Section on Enzymological Subjects (1964), 89(1), 95-108.

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
Mueller P, Schulze A, Schindler I, Ethofer T, Buehrdel P, Ceglarek U: Validation of an ESI-MS/MS screening method for acylcarnitine profiling in urine specimens of neonates, children, adolescents and adults. Clin Chim Acta. 2003 Jan;327(1-2):47-57. [PubMed:12482618 ]
Moder M, Kiessling A, Loster H, Bruggemann L: The pattern of urinary acylcarnitines determined by electrospray mass spectrometry: a new tool in the diagnosis of diabetes mellitus. Anal Bioanal Chem. 2003 Jan;375(2):200-10. Epub 2003 Jan 4. [PubMed:12560963 ]
Wasant P, Matsumoto I, Naylor E, Liammongkolkul S: Mitochondrial fatty acid oxidation disorders in Thai infants: a report of 3 cases. J Med Assoc Thai. 2002 Aug;85 Suppl 2:S710-9. [PubMed:12403251 ]
Young SP, Matern D, Gregersen N, Stevens RD, Bali D, Liu HM, Koeberl DD, Millington DS: A comparison of in vitro acylcarnitine profiling methods for the diagnosis of classical and variant short chain acyl-CoA dehydrogenase deficiency. Clin Chim Acta. 2003 Nov;337(1-2):103-13. [PubMed:14568186 ]
Poorthuis BJ, Jille-Vlckova T, Onkenhout W: Determination of acylcarnitines in urine of patients with inborn errors of metabolism using high-performance liquid chromatography after derivatization with 4'-bromophenacylbromide. Clin Chim Acta. 1993 Jul 16;216(1-2):53-61. [PubMed:8222273 ]
Bhuiyan AK, Jackson S, Turnbull DM, Aynsley-Green A, Leonard JV, Bartlett K: The measurement of carnitine and acyl-carnitines: application to the investigation of patients with suspected inherited disorders of mitochondrial fatty acid oxidation. Clin Chim Acta. 1992 May 15;207(3):185-204. [PubMed:1327583 ]
Nalecz KA, Miecz D, Berezowski V, Cecchelli R: Carnitine: transport and physiological functions in the brain. Mol Aspects Med. 2004 Oct-Dec;25(5-6):551-67. [PubMed:15363641 ]
Watanabe H, Kobayashi A, Hayashi H, Yamazaki N: Effects of long-chain acyl carnitine on membrane fluidity of human erythrocytes. Biochim Biophys Acta. 1989 Apr 28;980(3):315-8. [PubMed:2540838 ]
Goni FM, Requero MA, Alonso A: Palmitoylcarnitine, a surface-active metabolite. FEBS Lett. 1996 Jul 15;390(1):1-5. [PubMed:8706815 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

Enzyme Details

1. Carnitine O-palmitoyltransferase 1, muscle isoform

General function:: Involved in acyltransferase activity
Specific function:: Not Available
Gene Name:: CPT1B
Uniprot ID:: Q92523
Molecular weight:: 83890.705

Reactions

Palmityl-CoA + L-Carnitine → Coenzyme A + Palmitoylcarnitine	details

Enzyme Details

2. Carnitine O-palmitoyltransferase 1, liver isoform

General function:: Involved in acyltransferase activity
Specific function:: Catalyzes the transfer of the acyl group of long-chain fatty acid-CoA conjugates onto carnitine, an essential step for the mitochondrial uptake of long-chain fatty acids and their subsequent beta-oxidation in the mitochondrion. Plays an important role in triglyceride metabolism.
Gene Name:: CPT1A
Uniprot ID:: P50416
Molecular weight:: 86238.415

Reactions

Palmityl-CoA + L-Carnitine → Coenzyme A + Palmitoylcarnitine	details

Enzyme Details

3. Carnitine O-palmitoyltransferase 2, mitochondrial

General function:: Involved in acyltransferase activity
Specific function:: Not Available
Gene Name:: CPT2
Uniprot ID:: P23786
Molecular weight:: 73776.335

Reactions

Palmityl-CoA + L-Carnitine → Coenzyme A + Palmitoylcarnitine	details

Enzyme Details

4. Carnitine O-palmitoyltransferase 1, brain isoform

General function:: Involved in acyltransferase activity
Specific function:: Not Available
Gene Name:: CPT1C
Uniprot ID:: Q8TCG5
Molecular weight:: 89712.575

Reactions

Palmityl-CoA + L-Carnitine → Coenzyme A + Palmitoylcarnitine	details

Enzyme Details

5. Long-chain-fatty-acid--CoA ligase 1

General function:: Involved in catalytic activity
Specific function:: Activation of long-chain fatty acids for both synthesis of cellular lipids, and degradation via beta-oxidation. Preferentially uses palmitoleate, oleate and linoleate.
Gene Name:: ACSL1
Uniprot ID:: P33121
Molecular weight:: 77942.685

Showing metabocard for Palmitoylcarnitine (HMDB0000222)

MOL for HMDB0000222 (Palmitoylcarnitine)

3D MOL for HMDB0000222 (Palmitoylcarnitine)

3D SDF for HMDB0000222 (Palmitoylcarnitine)

3D-SDF for HMDB0000222 (Palmitoylcarnitine)

PDB for HMDB0000222 (Palmitoylcarnitine)

3D PDB for HMDB0000222 (Palmitoylcarnitine)

SMILES for HMDB0000222 (Palmitoylcarnitine)

INCHI for HMDB0000222 (Palmitoylcarnitine)

Structure for HMDB0000222 (Palmitoylcarnitine)

3D Structure for HMDB0000222 (Palmitoylcarnitine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions

Reactions

Reactions