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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-02-24 01:47:22 UTC

Update Date

2021-09-14 15:29:55 UTC

HMDB ID

HMDB0240774

Secondary Accession Numbers

None

Metabolite Identification

Common Name

L-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 increased during apoptosis. Palmitoylcarnitine was also 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

  Mrv1652302242102472D          

 29 28  0  0  1  0            999 V2000
    7.2336    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0940    3.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2690    4.1763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9190    4.1763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9480    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6625    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3770    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0914    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8059    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5204    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2349    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9493    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6638    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3783    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0927    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8072    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5217    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2362    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3796    6.2388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0940    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3796    5.4138    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.0940    6.6513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9506    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0940    4.1763    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   20.0940    7.4763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8085    6.2388    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   17.9506    6.2388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6651    5.0013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0940    5.8263    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 21 19  1  0  0  0  0
 21 20  1  0  0  0  0
 22 19  1  0  0  0  0
 23 18  1  0  0  0  0
 24  2  1  0  0  0  0
 24  3  1  0  0  0  0
 24  4  1  0  0  0  0
 24 20  1  0  0  0  0
 25 22  2  0  0  0  0
 26 22  1  0  0  0  0
 27 23  2  0  0  0  0
 21 28  1  6  0  0  0
 28 23  1  0  0  0  0
 21 29  1  6  0  0  0
M  CHG  2  24   1  26  -1
M  END

HMDB0240774
     RDKit          3D
L-Palmitoylcarnitine
 73 72  0  0  0  0  0  0  0  0999 V2000
    8.3690   -2.9847    0.1126 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2815   -1.6590    0.7979 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7135   -0.5824   -0.1245 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6531    0.7281    0.6276 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1061    1.8380   -0.2108 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7055    1.5998   -0.7147 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7185    1.4192    0.3861 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3339    1.1916   -0.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2695   -0.0260   -1.0591 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8835   -0.2153   -1.6210 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9114   -0.3815   -0.5054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5097   -0.5984   -0.9859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9908    0.5543   -1.7961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9958    1.8601   -1.0572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8657    1.8523    0.1591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2832    1.5711   -0.1155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0199    2.5231   -0.5478 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9058    0.3554    0.0519 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3018    0.2028   -0.2509 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3485   -0.7444   -1.4194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7572   -2.0617   -1.1703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2154   -2.4505   -0.1118 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7984   -2.9835   -2.2165 O   0  0  0  0  0  1  0  0  0  0  0  0
   -5.9834   -0.2545    0.9814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3986   -0.4597    0.8960 N   0  0  0  0  0  4  0  0  0  0  0  0
   -8.1099    0.4331    0.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7063   -1.8273    0.5386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9112   -0.2436    2.2661 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2668   -3.8437    0.8274 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3942   -3.0967   -0.3296 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6010   -3.1179   -0.6738 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6502   -1.7448    1.6929 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2870   -1.3091    1.1302 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7207   -0.9354   -0.4293 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3240   -0.4638   -1.0307 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0795    0.5460    1.5526 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6726    1.0227    0.9412 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7602    1.8968   -1.1296 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1683    2.8253    0.2637 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4165    2.4882   -1.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7652    0.7538   -1.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6615    2.3645    0.9648 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9487    0.6030    1.0806 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7037    0.9566    0.7225 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0246    2.1219   -0.6786 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4749   -0.9040   -0.4081 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9529    0.0112   -1.9325 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6158    0.7367   -2.1685 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8472   -1.0391   -2.3667 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8597    0.6051    0.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2299   -1.1964    0.1451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4685   -1.4873   -1.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1603   -0.8730   -0.1511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3387    0.6634   -2.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0054    0.3361   -2.1989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0049    2.2377   -0.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4468    2.6179   -1.7643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8261    2.8995    0.5819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5201    1.1974    0.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7262    1.1655   -0.6076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6880   -0.2612   -2.2079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3400   -0.7967   -1.9172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7402    0.4706    1.8096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5181   -1.2074    1.3268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1207    0.6220    0.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3565    0.0406   -0.9637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6437    1.4545    0.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9374   -1.8990   -0.5227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5710   -2.1872    1.1417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8433   -2.4757    0.7878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6679   -1.1039    2.9081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3619    0.6375    2.6580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9832    0.0112    2.2523 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  6
 20 61  1  0
 20 62  1  0
 24 63  1  0
 24 64  1  0
 26 65  1  0
 26 66  1  0
 26 67  1  0
 27 68  1  0
 27 69  1  0
 27 70  1  0
 28 71  1  0
 28 72  1  0
 28 73  1  0
M  CHG  2  23  -1  25   1
M  END

  Mrv1652302242102472D          

 29 28  0  0  1  0            999 V2000
    7.2336    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0940    3.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2690    4.1763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9190    4.1763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9480    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6625    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3770    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0914    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8059    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5204    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2349    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9493    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6638    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3783    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0927    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8072    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5217    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2362    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3796    6.2388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0940    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3796    5.4138    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.0940    6.6513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9506    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0940    4.1763    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   20.0940    7.4763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8085    6.2388    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   17.9506    6.2388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6651    5.0013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0940    5.8263    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 21 19  1  0  0  0  0
 21 20  1  0  0  0  0
 22 19  1  0  0  0  0
 23 18  1  0  0  0  0
 24  2  1  0  0  0  0
 24  3  1  0  0  0  0
 24  4  1  0  0  0  0
 24 20  1  0  0  0  0
 25 22  2  0  0  0  0
 26 22  1  0  0  0  0
 27 23  2  0  0  0  0
 21 28  1  6  0  0  0
 28 23  1  0  0  0  0
 21 29  1  6  0  0  0
M  CHG  2  24   1  26  -1
M  END
> <DATABASE_ID>
HMDB0240774

> <DATABASE_NAME>
hmdb

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

> <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-/m0/s1

> <INCHI_KEY>
XOMRRQXKHMYMOC-NRFANRHFSA-N

> <FORMULA>
C23H45NO4

> <MOLECULAR_WEIGHT>
399.616

> <EXACT_MASS>
399.334858933

$$$$

HMDB0240774
     RDKit          3D
L-Palmitoylcarnitine
 73 72  0  0  0  0  0  0  0  0999 V2000
    8.3690   -2.9847    0.1126 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2815   -1.6590    0.7979 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7135   -0.5824   -0.1245 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6531    0.7281    0.6276 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1061    1.8380   -0.2108 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7055    1.5998   -0.7147 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7185    1.4192    0.3861 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3339    1.1916   -0.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2695   -0.0260   -1.0591 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8835   -0.2153   -1.6210 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9114   -0.3815   -0.5054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5097   -0.5984   -0.9859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9908    0.5543   -1.7961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9958    1.8601   -1.0572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8657    1.8523    0.1591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2832    1.5711   -0.1155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0199    2.5231   -0.5478 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9058    0.3554    0.0519 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3018    0.2028   -0.2509 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3485   -0.7444   -1.4194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7572   -2.0617   -1.1703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2154   -2.4505   -0.1118 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7984   -2.9835   -2.2165 O   0  0  0  0  0  1  0  0  0  0  0  0
   -5.9834   -0.2545    0.9814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3986   -0.4597    0.8960 N   0  0  0  0  0  4  0  0  0  0  0  0
   -8.1099    0.4331    0.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7063   -1.8273    0.5386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9112   -0.2436    2.2661 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2668   -3.8437    0.8274 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3942   -3.0967   -0.3296 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6010   -3.1179   -0.6738 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6502   -1.7448    1.6929 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2870   -1.3091    1.1302 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7207   -0.9354   -0.4293 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3240   -0.4638   -1.0307 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0795    0.5460    1.5526 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6726    1.0227    0.9412 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7602    1.8968   -1.1296 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1683    2.8253    0.2637 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4165    2.4882   -1.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7652    0.7538   -1.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6615    2.3645    0.9648 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9487    0.6030    1.0806 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7037    0.9566    0.7225 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0246    2.1219   -0.6786 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4749   -0.9040   -0.4081 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9529    0.0112   -1.9325 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6158    0.7367   -2.1685 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8472   -1.0391   -2.3667 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8597    0.6051    0.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2299   -1.1964    0.1451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4685   -1.4873   -1.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1603   -0.8730   -0.1511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3387    0.6634   -2.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0054    0.3361   -2.1989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0049    2.2377   -0.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4468    2.6179   -1.7643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8261    2.8995    0.5819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5201    1.1974    0.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7262    1.1655   -0.6076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6880   -0.2612   -2.2079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3400   -0.7967   -1.9172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7402    0.4706    1.8096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5181   -1.2074    1.3268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1207    0.6220    0.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3565    0.0406   -0.9637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6437    1.4545    0.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9374   -1.8990   -0.5227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5710   -2.1872    1.1417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8433   -2.4757    0.7878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6679   -1.1039    2.9081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3619    0.6375    2.6580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9832    0.0112    2.2523 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  6
 20 61  1  0
 20 62  1  0
 24 63  1  0
 24 64  1  0
 26 65  1  0
 26 66  1  0
 26 67  1  0
 27 68  1  0
 27 69  1  0
 27 70  1  0
 28 71  1  0
 28 72  1  0
 28 73  1  0
M  CHG  2  23  -1  25   1
M  END

HEADER    PROTEIN                                 24-FEB-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-21         0                                  
HETATM    1  C   UNK     0      13.503   9.336   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      37.509   6.256   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      35.969   7.796   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      39.049   7.796   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.836  10.106   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.170   9.336   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.504  10.106   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      18.837   9.336   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      20.171  10.106   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.505   9.336   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      22.838  10.106   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      24.172   9.336   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      25.506  10.106   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      26.839   9.336   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      28.173  10.106   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      29.507   9.336   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      30.840  10.106   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      32.174   9.336   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      36.175  11.646   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      37.509   9.336   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      36.175  10.106   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      37.509  12.416   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      33.508  10.106   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0      37.509   7.796   0.000  0.00  0.00           N+1
HETATM   25  O   UNK     0      37.509  13.956   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      38.843  11.646   0.000  0.00  0.00           O-1
HETATM   27  O   UNK     0      33.508  11.646   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      34.842   9.336   0.000  0.00  0.00           O+0
HETATM   29  H   UNK     0      37.509  10.876   0.000  0.00  0.00           H+0
CONECT    1    5                                                            
CONECT    2   24                                                            
CONECT    3   24                                                            
CONECT    4   24                                                            
CONECT    5    1    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   23                                                       
CONECT   19   21   22                                                       
CONECT   20   21   24                                                       
CONECT   21   19   20   28   29                                             
CONECT   22   19   25   26                                                  
CONECT   23   18   27   28                                                  
CONECT   24    2    3    4   20                                             
CONECT   25   22                                                            
CONECT   26   22                                                            
CONECT   27   23                                                            
CONECT   28   21   23                                                       
CONECT   29   21                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   56    0
END

COMPND    HMDB0240774
HETATM    1  C1  UNL     1       8.369  -2.985   0.113  1.00  0.00           C  
HETATM    2  C2  UNL     1       8.281  -1.659   0.798  1.00  0.00           C  
HETATM    3  C3  UNL     1       7.714  -0.582  -0.124  1.00  0.00           C  
HETATM    4  C4  UNL     1       7.653   0.728   0.628  1.00  0.00           C  
HETATM    5  C5  UNL     1       7.106   1.838  -0.211  1.00  0.00           C  
HETATM    6  C6  UNL     1       5.705   1.600  -0.715  1.00  0.00           C  
HETATM    7  C7  UNL     1       4.719   1.419   0.386  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.334   1.192  -0.188  1.00  0.00           C  
HETATM    9  C9  UNL     1       3.270  -0.026  -1.059  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.884  -0.215  -1.621  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.911  -0.381  -0.505  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.510  -0.598  -0.986  1.00  0.00           C  
HETATM   13  C13 UNL     1      -0.991   0.554  -1.796  1.00  0.00           C  
HETATM   14  C14 UNL     1      -0.996   1.860  -1.057  1.00  0.00           C  
HETATM   15  C15 UNL     1      -1.866   1.852   0.159  1.00  0.00           C  
HETATM   16  C16 UNL     1      -3.283   1.571  -0.115  1.00  0.00           C  
HETATM   17  O1  UNL     1      -4.020   2.523  -0.548  1.00  0.00           O  
HETATM   18  O2  UNL     1      -3.906   0.355   0.052  1.00  0.00           O  
HETATM   19  C17 UNL     1      -5.302   0.203  -0.251  1.00  0.00           C  
HETATM   20  C18 UNL     1      -5.349  -0.744  -1.419  1.00  0.00           C  
HETATM   21  C19 UNL     1      -4.757  -2.062  -1.170  1.00  0.00           C  
HETATM   22  O3  UNL     1      -4.215  -2.451  -0.112  1.00  0.00           O  
HETATM   23  O4  UNL     1      -4.798  -2.984  -2.216  1.00  0.00           O1-
HETATM   24  C20 UNL     1      -5.983  -0.255   0.981  1.00  0.00           C  
HETATM   25  N1  UNL     1      -7.399  -0.460   0.896  1.00  0.00           N1+
HETATM   26  C21 UNL     1      -8.110   0.433   0.041  1.00  0.00           C  
HETATM   27  C22 UNL     1      -7.706  -1.827   0.539  1.00  0.00           C  
HETATM   28  C23 UNL     1      -7.911  -0.244   2.266  1.00  0.00           C  
HETATM   29  H1  UNL     1       8.267  -3.844   0.827  1.00  0.00           H  
HETATM   30  H2  UNL     1       9.394  -3.097  -0.330  1.00  0.00           H  
HETATM   31  H3  UNL     1       7.601  -3.118  -0.674  1.00  0.00           H  
HETATM   32  H4  UNL     1       7.650  -1.745   1.693  1.00  0.00           H  
HETATM   33  H5  UNL     1       9.287  -1.309   1.130  1.00  0.00           H  
HETATM   34  H6  UNL     1       6.721  -0.935  -0.429  1.00  0.00           H  
HETATM   35  H7  UNL     1       8.324  -0.464  -1.031  1.00  0.00           H  
HETATM   36  H8  UNL     1       7.079   0.546   1.553  1.00  0.00           H  
HETATM   37  H9  UNL     1       8.673   1.023   0.941  1.00  0.00           H  
HETATM   38  H10 UNL     1       7.760   1.897  -1.130  1.00  0.00           H  
HETATM   39  H11 UNL     1       7.168   2.825   0.264  1.00  0.00           H  
HETATM   40  H12 UNL     1       5.417   2.488  -1.303  1.00  0.00           H  
HETATM   41  H13 UNL     1       5.765   0.754  -1.426  1.00  0.00           H  
HETATM   42  H14 UNL     1       4.661   2.365   0.965  1.00  0.00           H  
HETATM   43  H15 UNL     1       4.949   0.603   1.081  1.00  0.00           H  
HETATM   44  H16 UNL     1       2.704   0.957   0.722  1.00  0.00           H  
HETATM   45  H17 UNL     1       3.025   2.122  -0.679  1.00  0.00           H  
HETATM   46  H18 UNL     1       3.475  -0.904  -0.408  1.00  0.00           H  
HETATM   47  H19 UNL     1       3.953   0.011  -1.933  1.00  0.00           H  
HETATM   48  H20 UNL     1       1.616   0.737  -2.168  1.00  0.00           H  
HETATM   49  H21 UNL     1       1.847  -1.039  -2.367  1.00  0.00           H  
HETATM   50  H22 UNL     1       0.860   0.605   0.045  1.00  0.00           H  
HETATM   51  H23 UNL     1       1.230  -1.196   0.145  1.00  0.00           H  
HETATM   52  H24 UNL     1      -0.469  -1.487  -1.662  1.00  0.00           H  
HETATM   53  H25 UNL     1      -1.160  -0.873  -0.151  1.00  0.00           H  
HETATM   54  H26 UNL     1      -0.339   0.663  -2.685  1.00  0.00           H  
HETATM   55  H27 UNL     1      -2.005   0.336  -2.199  1.00  0.00           H  
HETATM   56  H28 UNL     1      -0.005   2.238  -0.811  1.00  0.00           H  
HETATM   57  H29 UNL     1      -1.447   2.618  -1.764  1.00  0.00           H  
HETATM   58  H30 UNL     1      -1.826   2.900   0.582  1.00  0.00           H  
HETATM   59  H31 UNL     1      -1.520   1.197   0.962  1.00  0.00           H  
HETATM   60  H32 UNL     1      -5.726   1.166  -0.608  1.00  0.00           H  
HETATM   61  H33 UNL     1      -4.688  -0.261  -2.208  1.00  0.00           H  
HETATM   62  H34 UNL     1      -6.340  -0.797  -1.917  1.00  0.00           H  
HETATM   63  H35 UNL     1      -5.740   0.471   1.810  1.00  0.00           H  
HETATM   64  H36 UNL     1      -5.518  -1.207   1.327  1.00  0.00           H  
HETATM   65  H37 UNL     1      -9.121   0.622   0.511  1.00  0.00           H  
HETATM   66  H38 UNL     1      -8.357   0.041  -0.964  1.00  0.00           H  
HETATM   67  H39 UNL     1      -7.644   1.455   0.004  1.00  0.00           H  
HETATM   68  H40 UNL     1      -7.937  -1.899  -0.523  1.00  0.00           H  
HETATM   69  H41 UNL     1      -8.571  -2.187   1.142  1.00  0.00           H  
HETATM   70  H42 UNL     1      -6.843  -2.476   0.788  1.00  0.00           H  
HETATM   71  H43 UNL     1      -7.668  -1.104   2.908  1.00  0.00           H  
HETATM   72  H44 UNL     1      -7.362   0.637   2.658  1.00  0.00           H  
HETATM   73  H45 UNL     1      -8.983   0.011   2.252  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   24   25   63   64
CONECT   25   26   27   28
CONECT   26   65   66   67
CONECT   27   68   69   70
CONECT   28   71   72   73
END

HMDB0240774
     RDKit          3D
L-Palmitoylcarnitine
 73 72  0  0  0  0  0  0  0  0999 V2000
    8.3690   -2.9847    0.1126 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2815   -1.6590    0.7979 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7135   -0.5824   -0.1245 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6531    0.7281    0.6276 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1061    1.8380   -0.2108 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7055    1.5998   -0.7147 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7185    1.4192    0.3861 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3339    1.1916   -0.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2695   -0.0260   -1.0591 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8835   -0.2153   -1.6210 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9114   -0.3815   -0.5054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5097   -0.5984   -0.9859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9908    0.5543   -1.7961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9958    1.8601   -1.0572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8657    1.8523    0.1591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2832    1.5711   -0.1155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0199    2.5231   -0.5478 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9058    0.3554    0.0519 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3018    0.2028   -0.2509 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3485   -0.7444   -1.4194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7572   -2.0617   -1.1703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2154   -2.4505   -0.1118 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7984   -2.9835   -2.2165 O   0  0  0  0  0  1  0  0  0  0  0  0
   -5.9834   -0.2545    0.9814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3986   -0.4597    0.8960 N   0  0  0  0  0  4  0  0  0  0  0  0
   -8.1099    0.4331    0.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7063   -1.8273    0.5386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9112   -0.2436    2.2661 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2668   -3.8437    0.8274 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3942   -3.0967   -0.3296 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6010   -3.1179   -0.6738 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6502   -1.7448    1.6929 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2870   -1.3091    1.1302 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7207   -0.9354   -0.4293 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3240   -0.4638   -1.0307 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0795    0.5460    1.5526 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6726    1.0227    0.9412 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7602    1.8968   -1.1296 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1683    2.8253    0.2637 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4165    2.4882   -1.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7652    0.7538   -1.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6615    2.3645    0.9648 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9487    0.6030    1.0806 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7037    0.9566    0.7225 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0246    2.1219   -0.6786 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4749   -0.9040   -0.4081 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9529    0.0112   -1.9325 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6158    0.7367   -2.1685 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8472   -1.0391   -2.3667 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8597    0.6051    0.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2299   -1.1964    0.1451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4685   -1.4873   -1.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1603   -0.8730   -0.1511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3387    0.6634   -2.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0054    0.3361   -2.1989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0049    2.2377   -0.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4468    2.6179   -1.7643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8261    2.8995    0.5819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5201    1.1974    0.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7262    1.1655   -0.6076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6880   -0.2612   -2.2079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3400   -0.7967   -1.9172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7402    0.4706    1.8096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5181   -1.2074    1.3268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1207    0.6220    0.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3565    0.0406   -0.9637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6437    1.4545    0.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9374   -1.8990   -0.5227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5710   -2.1872    1.1417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8433   -2.4757    0.7878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6679   -1.1039    2.9081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3619    0.6375    2.6580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9832    0.0112    2.2523 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  6
 20 61  1  0
 20 62  1  0
 24 63  1  0
 24 64  1  0
 26 65  1  0
 26 66  1  0
 26 67  1  0
 27 68  1  0
 27 69  1  0
 27 70  1  0
 28 71  1  0
 28 72  1  0
 28 73  1  0
M  CHG  2  23  -1  25   1
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₃H₄₅NO₄

Average Molecular Weight

399.616

Monoisotopic Molecular Weight

399.334858933

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

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

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-/m0/s1

InChI Key

XOMRRQXKHMYMOC-NRFANRHFSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Acyl carnitines

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Disposition

Biological location

Cellular substructure

Organelle

Mitochondrion (HMDB: HMDB0240774)
Peroxisome (PMID: 35710135)

Cell

All cells and tissues (PMID: 35710135)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 35710135)
Saliva (HMDB: HMDB0240774)

Excreta

Biofluid or Excreta

Urine (PMID: 35710135)
Feces (HMDB: HMDB0240774)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0240774)

Source

Exogenous

Exogenous (HMDB: HMDB0240774)

Food

Food (HMDB: HMDB0240774)

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)

Endogenous

Endogenous (HMDB: HMDB0240774)

Animal

Animal (HMDB: HMDB0240774)

Process

Role

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	204.486	30932474
[M+H]+	Astarita_pos	217.0	30932474
[M+H]+	MetCCS_test_pos	214.027	30932474
[M-H]-	Not Available	204.486	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000185
[M+H]+	Not Available	214.0	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000185

Predicted Molecular Properties

Property	Value	Source

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	186.576	30932474
DeepCCS	[M-H]-	184.179	30932474
DeepCCS	[M-2H]-	218.209	30932474
DeepCCS	[M+Na]+	193.037	30932474
AllCCS	[M+H]+	217.2	32859911
AllCCS	[M+H-H2O]+	215.2	32859911
AllCCS	[M+NH4]+	218.9	32859911
AllCCS	[M+Na]+	219.4	32859911
AllCCS	[M-H]-	210.0	32859911
AllCCS	[M+Na-2H]-	211.6	32859911
AllCCS	[M+HCOO]-	213.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
L-Palmitoylcarnitine	[H][C@](CC([O-])=O)(C[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC	2962.0	Standard polar	33892256
L-Palmitoylcarnitine	[H][C@](CC([O-])=O)(C[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC	2461.2	Standard non polar	33892256
L-Palmitoylcarnitine	[H][C@](CC([O-])=O)(C[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC	2707.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - L-Palmitoylcarnitine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Palmitoylcarnitine 20V, Negative-QTOF	splash10-0a4i-0193000000-4e98054aa1c8a7c5e34c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Palmitoylcarnitine 40V, Negative-QTOF	splash10-0a4i-4696000000-0c7c24a252500b89aba8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Palmitoylcarnitine 40V, Positive-QTOF	splash10-000i-9000000000-99048e98e6b5a354c599	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Palmitoylcarnitine 10V, Negative-QTOF	splash10-0a4i-0194000000-0184776772e1f6226ed0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Palmitoylcarnitine 20V, Positive-QTOF	splash10-0f79-9000400000-6d3823e36ee3ebd7b10e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Palmitoylcarnitine 10V, Positive-QTOF	splash10-0udi-1000900000-7f8308808c84aa00fd01	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Palmitoylcarnitine 10V, Positive-QTOF	splash10-0udi-0000900000-b54b0a7f2164f15f15f2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Palmitoylcarnitine 20V, Positive-QTOF	splash10-0f79-9000500000-d7434e08a3e0942fa2e9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Palmitoylcarnitine 40V, Positive-QTOF	splash10-000i-9000000000-e9262cbaff8cb4ad0ba6	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

16016

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Palmitoylcarnitine

METLIN ID

Not Available

PubChem Compound

16902

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
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 ]
Minkler PE, Kerner J, North KN, Hoppel CL: Quantitation of long-chain acylcarnitines by HPLC/fluorescence detection: application to plasma and tissue specimens from patients with carnitine palmitoyltransferase-II deficiency. Clin Chim Acta. 2005 Feb;352(1-2):81-92. [PubMed:15653102 ]
Fingerhut R, Roschinger W, Muntau AC, Dame T, Kreischer J, Arnecke R, Superti-Furga A, Troxler H, Liebl B, Olgemoller B, Roscher AA: Hepatic carnitine palmitoyltransferase I deficiency: acylcarnitine profiles in blood spots are highly specific. Clin Chem. 2001 Oct;47(10):1763-8. [PubMed:11568084 ]
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 ]
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Showing metabocard for L-Palmitoylcarnitine (HMDB0240774)

MOL for HMDB0240774 (L-Palmitoylcarnitine)

3D MOL for HMDB0240774 (L-Palmitoylcarnitine)

3D SDF for HMDB0240774 (L-Palmitoylcarnitine)

3D-SDF for HMDB0240774 (L-Palmitoylcarnitine)

PDB for HMDB0240774 (L-Palmitoylcarnitine)

3D PDB for HMDB0240774 (L-Palmitoylcarnitine)

SMILES for HMDB0240774 (L-Palmitoylcarnitine)

INCHI for HMDB0240774 (L-Palmitoylcarnitine)

Structure for HMDB0240774 (L-Palmitoylcarnitine)

3D Structure for HMDB0240774 (L-Palmitoylcarnitine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra