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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2007-05-23 10:45:07 UTC

Update Date

2022-03-07 02:49:31 UTC

HMDB ID

HMDB0006469

Secondary Accession Numbers

HMDB0013212
HMDB06469
HMDB13212

Metabolite Identification

Common Name

Linoleyl carnitine

Description

Linoleyl carnitine is a long-chain acyl fatty acid derivative ester of carnitine. Long-chain acyl fatty acid derivatives accumulate in the cytosol and serum of patients suffering of mitochondrial carnitine palmitoyltransferase II (CPT II, EC 2.3.1.12) deficiency, the most common inherited disorder of lipid metabolism in adults. Carnitine palmitoyltransferase II deficiency is an autosomal recessive disorder of fatty acid metabolism presenting as two clinical phenotypes: (i) a severe infantile hepatocardiomuscular form and (ii) a milder adult muscular form. Energy production from long-chain fatty acids (LCFAs) requires the transport of LCFAs into the mitochondrial matrix. This transport is carnitine-dependent and involves translocation machinery. Mitochondrial fatty acid oxidation disorders cause hypoglycaemia, hepatic dysfunction, myopathy, cardiomyopathy and encephalopathy. Patients with end-stage renal disease (ESRD) undergoing long-term haemodialysis exhibit elevated acylcarnitine concentrations (PMID: 11999976 , 10682306 , 15025677 , 16168195 ). Moreover, linoleyl carnitine is found to be associated with glutaric aciduria II, which is an inborn error of metabolism.

Structure

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

  Mrv1652303202017022D          

 30 29  0  0  0  0            999 V2000
 9993.8988 9999.7907    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9994.6128 9999.3774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9993.898810000.6151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.1931 9999.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.3268 9999.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.184810001.0255    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
 9993.1931 9998.5428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0408 9999.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.326810000.6151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.466910000.6130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.184810001.8504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.331810001.5184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.9071 9998.1295    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
 9992.4791 9998.1295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7549 9999.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4689 9999.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1829 9999.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8969 9999.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6109 9999.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3253 9999.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0389 9999.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.8638 9999.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.5795 9999.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.2931 9999.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.1181 9999.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.8316 9999.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.5452 9999.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.2588 9999.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.9745 9999.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.6881 9999.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  6  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  4  7  1  0  0  0  0
  5  8  1  0  0  0  0
  5  9  2  0  0  0  0
  6 10  1  0  0  0  0
  6 11  1  0  0  0  0
  6 12  1  0  0  0  0
  7 13  1  0  0  0  0
  7 14  2  0  0  0  0
  8 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
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  CHG  2   6   1  13  -1
M  END

HMDB0006469
     RDKit          3D
Linoleyl carnitine
 76 75  0  0  0  0  0  0  0  0999 V2000
    9.4100    2.8345    0.8061 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6143    1.3786    0.5218 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2670    0.6844    0.3513 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4837   -0.7723    0.0682 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1173   -1.4507   -0.0725 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4088   -1.2554    1.1861 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2877   -0.6966    1.4617 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3317   -0.0527    0.5599 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6584    0.0563   -0.8450 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0296   -0.4469   -1.8567 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8467   -1.2455   -2.0564 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8681   -1.5794   -1.0187 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0813   -0.3391   -0.6236 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0975   -0.5908    0.4854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9031   -1.6204    0.0976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7047   -1.2685   -1.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5096   -0.0117   -1.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4819   -0.1114    0.0844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1516   -0.2884    1.2806 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8494   -0.0120   -0.1490 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8155   -0.1021    0.8862 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.5610   -1.3827    0.6937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6076   -1.6811    1.6692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8779   -0.9709    2.6584 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3496   -2.8537    1.4607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5992    1.1322    1.0698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3758    1.6325    0.0023 N   0  0  0  0  0  4  0  0  0  0  0  0
   -6.9614    2.9807   -0.4078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5037    0.8420   -1.1747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7548    1.8288    0.5011 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3769    3.0954    0.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1596    3.4456    0.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5548    3.0430    1.9024 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1310    0.8687    1.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1416    1.2864   -0.4346 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6207    0.8654    1.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7708    1.2049   -0.5171 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1175   -0.9569   -0.7984 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9199   -1.2120    1.0086 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6870   -1.1701   -1.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3918   -2.5568   -0.2017 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9930   -1.6964    2.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9981   -0.7012    2.5473 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2165    1.0439    0.9221 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2976   -0.4396    0.8009 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5639    0.7217   -1.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5801   -0.1691   -2.8478 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1300   -2.2105   -2.6511 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2291   -0.7255   -2.8930 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2131   -2.1788   -0.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1172   -2.3073   -1.5187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5101   -0.0353   -1.5725 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6759    0.5432   -0.3930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3471    0.3814    0.7751 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6804   -0.9299    1.3672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3259   -2.5484   -0.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5753   -1.8832    0.9412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1192   -1.2916   -2.0492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4545   -2.1067   -1.2373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8769    0.9016   -0.9449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0966    0.0387   -1.9869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2238   -0.2481    1.8452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8873   -1.5727   -0.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7779   -2.2129    0.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7977   -3.7039    1.4192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1977    1.0719    2.0138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8636    1.9765    1.3298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8339    3.4073   -0.9859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8343    3.6339    0.4695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1170    2.9648   -1.0982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3598    0.1216   -1.0775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8884    1.5555   -1.9751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5967    0.4272   -1.6026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8697    2.7890    1.0087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0554    1.0266    1.1909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4732    1.8049   -0.3494 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  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  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  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 21 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 27 30  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  4 39  1  0
  5 40  1  0
  5 41  1  0
  6 42  1  0
  7 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  0
 10 47  1  0
 11 48  1  0
 11 49  1  0
 12 50  1  0
 12 51  1  0
 13 52  1  0
 13 53  1  0
 14 54  1  0
 14 55  1  0
 15 56  1  0
 15 57  1  0
 16 58  1  0
 16 59  1  0
 17 60  1  0
 17 61  1  0
 21 62  1  1
 22 63  1  0
 22 64  1  0
 25 65  1  0
 26 66  1  0
 26 67  1  0
 28 68  1  0
 28 69  1  0
 28 70  1  0
 29 71  1  0
 29 72  1  0
 29 73  1  0
 30 74  1  0
 30 75  1  0
 30 76  1  0
M  CHG  1  27   1
M  END

  Mrv1652303202017022D          

 30 29  0  0  0  0            999 V2000
 9993.8988 9999.7907    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9994.6128 9999.3774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9993.898810000.6151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.1931 9999.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.3268 9999.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.184810001.0255    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
 9993.1931 9998.5428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0408 9999.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.326810000.6151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.466910000.6130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.184810001.8504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.331810001.5184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.9071 9998.1295    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
 9992.4791 9998.1295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7549 9999.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4689 9999.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1829 9999.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8969 9999.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6109 9999.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3253 9999.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0389 9999.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.8638 9999.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.5795 9999.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.2931 9999.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.1181 9999.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.8316 9999.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.5452 9999.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.2588 9999.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.9745 9999.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.6881 9999.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  6  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  4  7  1  0  0  0  0
  5  8  1  0  0  0  0
  5  9  2  0  0  0  0
  6 10  1  0  0  0  0
  6 11  1  0  0  0  0
  6 12  1  0  0  0  0
  7 13  1  0  0  0  0
  7 14  2  0  0  0  0
  8 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
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  CHG  2   6   1  13  -1
M  END
> <DATABASE_ID>
HMDB0006469

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC\C=C/C\C=C/CCCCCCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C25H45NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-25(29)30-23(21-24(27)28)22-26(2,3)4/h9-10,12-13,23H,5-8,11,14-22H2,1-4H3/b10-9-,13-12-/t23-/m1/s1

> <INCHI_KEY>
MJLXQSQYKZWZCB-DQFWFXSYSA-N

> <FORMULA>
C25H45NO4

> <MOLECULAR_WEIGHT>
423.6291

> <EXACT_MASS>
423.334858933

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
51.76996122414735

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R)-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]-4-(trimethylazaniumyl)butanoate

> <ALOGPS_LOGP>
1.46

> <JCHEM_LOGP>
2.1988418708615876

> <ALOGPS_LOGS>
-7.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.216763902737658

> <JCHEM_PKA_STRONGEST_BASIC>
-7.057186892022398

> <JCHEM_POLAR_SURFACE_AREA>
66.43

> <JCHEM_REFRACTIVITY>
148.5119

> <JCHEM_ROTATABLE_BOND_COUNT>
20

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.62e-06 g/l

> <JCHEM_TRADITIONAL_IUPAC>
linoleoylcarnitine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0006469
     RDKit          3D
Linoleyl carnitine
 76 75  0  0  0  0  0  0  0  0999 V2000
    9.4100    2.8345    0.8061 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6143    1.3786    0.5218 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2670    0.6844    0.3513 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4837   -0.7723    0.0682 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1173   -1.4507   -0.0725 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4088   -1.2554    1.1861 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2877   -0.6966    1.4617 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3317   -0.0527    0.5599 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6584    0.0563   -0.8450 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0296   -0.4469   -1.8567 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8467   -1.2455   -2.0564 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8681   -1.5794   -1.0187 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0813   -0.3391   -0.6236 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0975   -0.5908    0.4854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9031   -1.6204    0.0976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7047   -1.2685   -1.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5096   -0.0117   -1.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4819   -0.1114    0.0844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1516   -0.2884    1.2806 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8494   -0.0120   -0.1490 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8155   -0.1021    0.8862 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.5610   -1.3827    0.6937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6076   -1.6811    1.6692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8779   -0.9709    2.6584 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3496   -2.8537    1.4607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5992    1.1322    1.0698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3758    1.6325    0.0023 N   0  0  0  0  0  4  0  0  0  0  0  0
   -6.9614    2.9807   -0.4078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5037    0.8420   -1.1747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7548    1.8288    0.5011 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3769    3.0954    0.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1596    3.4456    0.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5548    3.0430    1.9024 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1310    0.8687    1.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1416    1.2864   -0.4346 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6207    0.8654    1.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7708    1.2049   -0.5171 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1175   -0.9569   -0.7984 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9199   -1.2120    1.0086 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6870   -1.1701   -1.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3918   -2.5568   -0.2017 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9930   -1.6964    2.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9981   -0.7012    2.5473 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2165    1.0439    0.9221 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2976   -0.4396    0.8009 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5639    0.7217   -1.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5801   -0.1691   -2.8478 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1300   -2.2105   -2.6511 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2291   -0.7255   -2.8930 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2131   -2.1788   -0.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1172   -2.3073   -1.5187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5101   -0.0353   -1.5725 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6759    0.5432   -0.3930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3471    0.3814    0.7751 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6804   -0.9299    1.3672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3259   -2.5484   -0.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5753   -1.8832    0.9412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1192   -1.2916   -2.0492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4545   -2.1067   -1.2373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8769    0.9016   -0.9449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0966    0.0387   -1.9869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2238   -0.2481    1.8452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8873   -1.5727   -0.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7779   -2.2129    0.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7977   -3.7039    1.4192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1977    1.0719    2.0138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8636    1.9765    1.3298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8339    3.4073   -0.9859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8343    3.6339    0.4695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1170    2.9648   -1.0982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3598    0.1216   -1.0775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8884    1.5555   -1.9751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5967    0.4272   -1.6026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8697    2.7890    1.0087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0554    1.0266    1.1909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4732    1.8049   -0.3494 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  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  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  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 21 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 27 30  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  4 39  1  0
  5 40  1  0
  5 41  1  0
  6 42  1  0
  7 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  0
 10 47  1  0
 11 48  1  0
 11 49  1  0
 12 50  1  0
 12 51  1  0
 13 52  1  0
 13 53  1  0
 14 54  1  0
 14 55  1  0
 15 56  1  0
 15 57  1  0
 16 58  1  0
 16 59  1  0
 17 60  1  0
 17 61  1  0
 21 62  1  1
 22 63  1  0
 22 64  1  0
 25 65  1  0
 26 66  1  0
 26 67  1  0
 28 68  1  0
 28 69  1  0
 28 70  1  0
 29 71  1  0
 29 72  1  0
 29 73  1  0
 30 74  1  0
 30 75  1  0
 30 76  1  0
M  CHG  1  27   1
M  END

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0    8655.2788666.276   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8656.6118665.504   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8655.2788667.815   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8653.9608665.485   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8657.9438666.276   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0    8653.9458668.581   0.000  0.00  0.00           N+1
HETATM    7  C   UNK     0    8653.9608663.947   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8659.2768665.504   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0    8657.9438667.815   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0    8652.6058667.811   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8653.9458670.121   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8652.3538669.501   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0    8655.2938663.175   0.000  0.00  0.00           O-1
HETATM   14  O   UNK     0    8652.6288663.175   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0    8660.6098666.276   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8661.9428665.504   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8663.2758666.276   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8664.6088665.504   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8665.9408666.276   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8667.2748665.504   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8668.6068666.276   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8670.1468666.276   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8671.4828665.504   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8672.8148666.276   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8674.3548666.276   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8675.6868665.504   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8677.0188666.276   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8678.3508665.504   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8679.6868666.276   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8681.0188665.504   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1    6                                                       
CONECT    4    1    7                                                       
CONECT    5    2    8    9                                                  
CONECT    6    3   10   11   12                                             
CONECT    7    4   13   14                                                  
CONECT    8    5   15                                                       
CONECT    9    5                                                            
CONECT   10    6                                                            
CONECT   11    6                                                            
CONECT   12    6                                                            
CONECT   13    7                                                            
CONECT   14    7                                                            
CONECT   15    8   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   58    0
END

COMPND    HMDB0006469
HETATM    1  C1  UNL     1       9.410   2.835   0.806  1.00  0.00           C  
HETATM    2  C2  UNL     1       9.614   1.379   0.522  1.00  0.00           C  
HETATM    3  C3  UNL     1       8.267   0.684   0.351  1.00  0.00           C  
HETATM    4  C4  UNL     1       8.484  -0.772   0.068  1.00  0.00           C  
HETATM    5  C5  UNL     1       7.117  -1.451  -0.072  1.00  0.00           C  
HETATM    6  C6  UNL     1       6.409  -1.255   1.186  1.00  0.00           C  
HETATM    7  C7  UNL     1       5.288  -0.697   1.462  1.00  0.00           C  
HETATM    8  C8  UNL     1       4.332  -0.053   0.560  1.00  0.00           C  
HETATM    9  C9  UNL     1       4.658   0.056  -0.845  1.00  0.00           C  
HETATM   10  C10 UNL     1       4.030  -0.447  -1.857  1.00  0.00           C  
HETATM   11  C11 UNL     1       2.847  -1.246  -2.056  1.00  0.00           C  
HETATM   12  C12 UNL     1       1.868  -1.579  -1.019  1.00  0.00           C  
HETATM   13  C13 UNL     1       1.081  -0.339  -0.624  1.00  0.00           C  
HETATM   14  C14 UNL     1       0.098  -0.591   0.485  1.00  0.00           C  
HETATM   15  C15 UNL     1      -0.903  -1.620   0.098  1.00  0.00           C  
HETATM   16  C16 UNL     1      -1.705  -1.269  -1.102  1.00  0.00           C  
HETATM   17  C17 UNL     1      -2.510  -0.012  -1.023  1.00  0.00           C  
HETATM   18  C18 UNL     1      -3.482  -0.111   0.084  1.00  0.00           C  
HETATM   19  O1  UNL     1      -3.152  -0.288   1.281  1.00  0.00           O  
HETATM   20  O2  UNL     1      -4.849  -0.012  -0.149  1.00  0.00           O  
HETATM   21  C19 UNL     1      -5.816  -0.102   0.886  1.00  0.00           C  
HETATM   22  C20 UNL     1      -6.561  -1.383   0.694  1.00  0.00           C  
HETATM   23  C21 UNL     1      -7.608  -1.681   1.669  1.00  0.00           C  
HETATM   24  O3  UNL     1      -7.878  -0.971   2.658  1.00  0.00           O  
HETATM   25  O4  UNL     1      -8.350  -2.854   1.461  1.00  0.00           O  
HETATM   26  C22 UNL     1      -6.599   1.132   1.070  1.00  0.00           C  
HETATM   27  N1  UNL     1      -7.376   1.632   0.002  1.00  0.00           N1+
HETATM   28  C23 UNL     1      -6.961   2.981  -0.408  1.00  0.00           C  
HETATM   29  C24 UNL     1      -7.504   0.842  -1.175  1.00  0.00           C  
HETATM   30  C25 UNL     1      -8.755   1.829   0.501  1.00  0.00           C  
HETATM   31  H1  UNL     1       8.377   3.095   0.492  1.00  0.00           H  
HETATM   32  H2  UNL     1      10.160   3.446   0.247  1.00  0.00           H  
HETATM   33  H3  UNL     1       9.555   3.043   1.902  1.00  0.00           H  
HETATM   34  H4  UNL     1      10.131   0.869   1.348  1.00  0.00           H  
HETATM   35  H5  UNL     1      10.142   1.286  -0.435  1.00  0.00           H  
HETATM   36  H6  UNL     1       7.621   0.865   1.228  1.00  0.00           H  
HETATM   37  H7  UNL     1       7.771   1.205  -0.517  1.00  0.00           H  
HETATM   38  H8  UNL     1       9.118  -0.957  -0.798  1.00  0.00           H  
HETATM   39  H9  UNL     1       8.920  -1.212   1.009  1.00  0.00           H  
HETATM   40  H10 UNL     1       6.687  -1.170  -1.004  1.00  0.00           H  
HETATM   41  H11 UNL     1       7.392  -2.557  -0.202  1.00  0.00           H  
HETATM   42  H12 UNL     1       6.993  -1.696   2.070  1.00  0.00           H  
HETATM   43  H13 UNL     1       4.998  -0.701   2.547  1.00  0.00           H  
HETATM   44  H14 UNL     1       4.216   1.044   0.922  1.00  0.00           H  
HETATM   45  H15 UNL     1       3.298  -0.440   0.801  1.00  0.00           H  
HETATM   46  H16 UNL     1       5.564   0.722  -1.044  1.00  0.00           H  
HETATM   47  H17 UNL     1       4.580  -0.169  -2.848  1.00  0.00           H  
HETATM   48  H18 UNL     1       3.130  -2.211  -2.651  1.00  0.00           H  
HETATM   49  H19 UNL     1       2.229  -0.726  -2.893  1.00  0.00           H  
HETATM   50  H20 UNL     1       2.213  -2.179  -0.159  1.00  0.00           H  
HETATM   51  H21 UNL     1       1.117  -2.307  -1.519  1.00  0.00           H  
HETATM   52  H22 UNL     1       0.510  -0.035  -1.573  1.00  0.00           H  
HETATM   53  H23 UNL     1       1.676   0.543  -0.393  1.00  0.00           H  
HETATM   54  H24 UNL     1      -0.347   0.381   0.775  1.00  0.00           H  
HETATM   55  H25 UNL     1       0.680  -0.930   1.367  1.00  0.00           H  
HETATM   56  H26 UNL     1      -0.326  -2.548  -0.168  1.00  0.00           H  
HETATM   57  H27 UNL     1      -1.575  -1.883   0.941  1.00  0.00           H  
HETATM   58  H28 UNL     1      -1.119  -1.292  -2.049  1.00  0.00           H  
HETATM   59  H29 UNL     1      -2.455  -2.107  -1.237  1.00  0.00           H  
HETATM   60  H30 UNL     1      -1.877   0.902  -0.945  1.00  0.00           H  
HETATM   61  H31 UNL     1      -3.097   0.039  -1.987  1.00  0.00           H  
HETATM   62  H32 UNL     1      -5.224  -0.248   1.845  1.00  0.00           H  
HETATM   63  H33 UNL     1      -6.887  -1.573  -0.363  1.00  0.00           H  
HETATM   64  H34 UNL     1      -5.778  -2.213   0.831  1.00  0.00           H  
HETATM   65  H35 UNL     1      -7.798  -3.704   1.419  1.00  0.00           H  
HETATM   66  H36 UNL     1      -7.198   1.072   2.014  1.00  0.00           H  
HETATM   67  H37 UNL     1      -5.864   1.977   1.330  1.00  0.00           H  
HETATM   68  H38 UNL     1      -7.834   3.407  -0.986  1.00  0.00           H  
HETATM   69  H39 UNL     1      -6.834   3.634   0.470  1.00  0.00           H  
HETATM   70  H40 UNL     1      -6.117   2.965  -1.098  1.00  0.00           H  
HETATM   71  H41 UNL     1      -8.360   0.122  -1.078  1.00  0.00           H  
HETATM   72  H42 UNL     1      -7.888   1.555  -1.975  1.00  0.00           H  
HETATM   73  H43 UNL     1      -6.597   0.427  -1.603  1.00  0.00           H  
HETATM   74  H44 UNL     1      -8.870   2.789   1.009  1.00  0.00           H  
HETATM   75  H45 UNL     1      -9.055   1.027   1.191  1.00  0.00           H  
HETATM   76  H46 UNL     1      -9.473   1.805  -0.349  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3   34   35
CONECT    3    4   36   37
CONECT    4    5   38   39
CONECT    5    6   40   41
CONECT    6    7    7   42
CONECT    7    8   43
CONECT    8    9   44   45
CONECT    9   10   10   46
CONECT   10   11   47
CONECT   11   12   48   49
CONECT   12   13   50   51
CONECT   13   14   52   53
CONECT   14   15   54   55
CONECT   15   16   56   57
CONECT   16   17   58   59
CONECT   17   18   60   61
CONECT   18   19   19   20
CONECT   20   21
CONECT   21   22   26   62
CONECT   22   23   63   64
CONECT   23   24   24   25
CONECT   25   65
CONECT   26   27   66   67
CONECT   27   28   29   30
CONECT   28   68   69   70
CONECT   29   71   72   73
CONECT   30   74   75   76
END

HMDB0006469
     RDKit          3D
Linoleyl carnitine
 76 75  0  0  0  0  0  0  0  0999 V2000
    9.4100    2.8345    0.8061 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6143    1.3786    0.5218 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2670    0.6844    0.3513 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4837   -0.7723    0.0682 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1173   -1.4507   -0.0725 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4088   -1.2554    1.1861 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2877   -0.6966    1.4617 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3317   -0.0527    0.5599 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6584    0.0563   -0.8450 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0296   -0.4469   -1.8567 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8467   -1.2455   -2.0564 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8681   -1.5794   -1.0187 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0813   -0.3391   -0.6236 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0975   -0.5908    0.4854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9031   -1.6204    0.0976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7047   -1.2685   -1.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5096   -0.0117   -1.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4819   -0.1114    0.0844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1516   -0.2884    1.2806 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8494   -0.0120   -0.1490 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8155   -0.1021    0.8862 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.5610   -1.3827    0.6937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6076   -1.6811    1.6692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8779   -0.9709    2.6584 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3496   -2.8537    1.4607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5992    1.1322    1.0698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3758    1.6325    0.0023 N   0  0  0  0  0  4  0  0  0  0  0  0
   -6.9614    2.9807   -0.4078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5037    0.8420   -1.1747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7548    1.8288    0.5011 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3769    3.0954    0.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1596    3.4456    0.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5548    3.0430    1.9024 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1310    0.8687    1.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1416    1.2864   -0.4346 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6207    0.8654    1.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7708    1.2049   -0.5171 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1175   -0.9569   -0.7984 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9199   -1.2120    1.0086 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6870   -1.1701   -1.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3918   -2.5568   -0.2017 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9930   -1.6964    2.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9981   -0.7012    2.5473 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2165    1.0439    0.9221 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2976   -0.4396    0.8009 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5639    0.7217   -1.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5801   -0.1691   -2.8478 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1300   -2.2105   -2.6511 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2291   -0.7255   -2.8930 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2131   -2.1788   -0.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1172   -2.3073   -1.5187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5101   -0.0353   -1.5725 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6759    0.5432   -0.3930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3471    0.3814    0.7751 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6804   -0.9299    1.3672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3259   -2.5484   -0.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5753   -1.8832    0.9412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1192   -1.2916   -2.0492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4545   -2.1067   -1.2373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8769    0.9016   -0.9449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0966    0.0387   -1.9869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2238   -0.2481    1.8452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8873   -1.5727   -0.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7779   -2.2129    0.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7977   -3.7039    1.4192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1977    1.0719    2.0138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8636    1.9765    1.3298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8339    3.4073   -0.9859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8343    3.6339    0.4695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1170    2.9648   -1.0982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3598    0.1216   -1.0775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8884    1.5555   -1.9751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5967    0.4272   -1.6026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8697    2.7890    1.0087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0554    1.0266    1.1909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4732    1.8049   -0.3494 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  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  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  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 21 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 27 30  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  4 39  1  0
  5 40  1  0
  5 41  1  0
  6 42  1  0
  7 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  0
 10 47  1  0
 11 48  1  0
 11 49  1  0
 12 50  1  0
 12 51  1  0
 13 52  1  0
 13 53  1  0
 14 54  1  0
 14 55  1  0
 15 56  1  0
 15 57  1  0
 16 58  1  0
 16 59  1  0
 17 60  1  0
 17 61  1  0
 21 62  1  1
 22 63  1  0
 22 64  1  0
 25 65  1  0
 26 66  1  0
 26 67  1  0
 28 68  1  0
 28 69  1  0
 28 70  1  0
 29 71  1  0
 29 72  1  0
 29 73  1  0
 30 74  1  0
 30 75  1  0
 30 76  1  0
M  CHG  1  27   1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Decadienylcarnitine	ChEBI
Octadecadienyl-L-carnitine	ChEBI
3-Carboxy-N,N,N-trimethyl-2-[(1-oxo-9,12-octadecadienyl)oxy]-1-propanaminium	HMDB
3-Carboxy-N,N,N-trimethyl-2-[[(9Z,12Z)-1-oxo-9,12-octadecadienyl]oxy]-1-propanaminium	HMDB
9,12-Octadecadienoylcarnitine	HMDB
9,12-Octadecadienylcarnitine	HMDB
alpha-Linoleoylcarnitine	HMDB
Linoleic acid carnitine	HMDB
Linoleoyl carnitine	HMDB
Linoleoylcarnitine	HMDB
C18:2 Carnitine	HMDB
L-Linoleoylcarnitine	HMDB

Chemical Formula

C₂₅H₄₆NO₄

Average Molecular Weight

424.645

Monoisotopic Molecular Weight

424.342135385

IUPAC Name

(3R)-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]-4-(trimethylazaniumyl)butanoate

Traditional Name

linoleoylcarnitine

CAS Registry Number

36816-10-1

SMILES

CCCCC\C=C/C\C=C/CCCCCCCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C

InChI Identifier

InChI=1S/C25H45NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-25(29)30-23(21-24(27)28)22-26(2,3)4/h9-10,12-13,23H,5-8,11,14-22H2,1-4H3/p+1/b10-9-,13-12-/t23-/m1/s1

InChI Key

MJLXQSQYKZWZCB-DQFWFXSYSA-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-octadecadienoyl-L-carnitine (CHEBI:84098 )
Fatty acyl carnitines (LMFA07070009 )

Ontology

Not Available

Not Available

Not Available

Not Available

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	8.6e-06 g/L	ALOGPS
logP	1.46	ALOGPS
logP	2.2	ChemAxon
logS	-7.7	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	148.51 m³·mol⁻¹	ChemAxon
Polarizability	51.77 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]+	219.566	30932474
DeepCCS	[M-H]-	217.208	30932474
DeepCCS	[M-2H]-	251.054	30932474
DeepCCS	[M+Na]+	227.222	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Linoleyl carnitine	CCCCC\C=C/C\C=C/CCCCCCCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C	3688.6	Standard polar	33892256
Linoleyl carnitine	CCCCC\C=C/C\C=C/CCCCCCCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C	2583.0	Standard non polar	33892256
Linoleyl carnitine	CCCCC\C=C/C\C=C/CCCCCCCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C	2916.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Linoleyl carnitine,1TMS,isomer #1	CCCCC/C=C\C/C=C\CCCCCCCC(=O)O[C@H](CC(=O)O[Si](C)(C)C)C[N+](C)(C)C	2962.5	Semi standard non polar	33892256
Linoleyl carnitine,1TBDMS,isomer #1	CCCCC/C=C\C/C=C\CCCCCCCC(=O)O[C@H](CC(=O)O[Si](C)(C)C(C)(C)C)C[N+](C)(C)C	3192.3	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 - cis,cis-9,12-Octadecadienoyl-L-carnitine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-9230000000-8e303f952de7b09a4059	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cis,cis-9,12-Octadecadienoyl-L-carnitine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cis,cis-9,12-Octadecadienoyl-L-carnitine 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linoleyl carnitine 10V, Positive-QTOF	splash10-074l-0953800000-c042c48279e03c6942dd	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linoleyl carnitine 20V, Positive-QTOF	splash10-0006-1920000000-23f60e51d007ae34b3c8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linoleyl carnitine 40V, Positive-QTOF	splash10-0006-4930000000-838683bf758f3bdc0bfd	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linoleyl carnitine 10V, Negative-QTOF	splash10-00di-1031900000-9dae0fd9ea2fd4d9a94a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linoleyl carnitine 20V, Negative-QTOF	splash10-03k9-1179400000-b3c183368ca837a1abb3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linoleyl carnitine 40V, Negative-QTOF	splash10-06vu-5090000000-1b5b91637ffacc86b31f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linoleyl carnitine 10V, Positive-QTOF	splash10-00di-0000900000-013b520638a6f6e841ef	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linoleyl carnitine 20V, Positive-QTOF	splash10-0079-9000500000-f8699786d83873f3e7b3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linoleyl carnitine 40V, Positive-QTOF	splash10-000i-9000000000-e9262cbaff8cb4ad0ba6	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane
Mitochondria

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.06 +/- 0.03 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	0.040-0.080 uM	Adult (>18 years old)	Both	Normal	Molecular You	details
Blood	Detected and Quantified	0.05 +/- 0.02 uM	Adult (>18 years old)	Both	Normal	28278231	details
Blood	Detected and Quantified	0.05(0.02) uM	Adult (>18 years old)	Both	Normal	26010610	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	0.51 uM	Infant (0-1 year old)	Male	Normal	16388731	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected and Quantified	0.36 +/- 0.23 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Feces	Detected and Quantified	0.14 +/- 0.09 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Feces	Detected and Quantified	0.36 +/- 0.17 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Feces	Detected and Quantified	0.1 +/- 0.07 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Urine	Detected and Quantified	0.10 (0.04-0.30) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.0007 (0.0003-0.002) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	0.0-0.01 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	32340350	details
Urine	Detected and Quantified	0.0 (0.0-0.01) umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	32340350	details
Urine	Detected and Quantified	0.0 (0.0-0.01) umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	32340350	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.042 +/- 0.011 uM	Children (1-13 years old)	Both	Obesity	Metabolomics reve...	details
Blood	Detected and Quantified	0.07(0.03) uM	Adult (>18 years old)	Both	Heart failure with preserved ejection fraction	26010610	details
Blood	Detected and Quantified	0.045 +/- 0.010 uM	Children (1-13 years old)	Both	Obesity	Metabolomics reve...	details
Blood	Detected and Quantified	0.06(0.02) uM	Adult (>18 years old)	Both	Heart failure with reduced ejection fraction	26010610	details
Blood	Detected and Quantified	0.0317 (0.0179) uM	Adult (>18 years old)	Female	Pregnancy with fetus having congenital heart defect	24704061	details
Blood	Detected and Quantified	0.0208 (0.0151) uM	Adult (>18 years old)	Female	Pregnancy with fetus having congenital heart defect	24704061	details
Blood	Detected and Quantified	0.0498 (0.0156) uM	Adult (>18 years old)	Female	Pregnancy	24704061	details
Blood	Detected and Quantified	2.35 uM	Infant (0-1 year old)	Male	Glutaric aciduria II	16388731	details

Associated Disorders and Diseases

Disease References

Pregnancy
Bahado-Singh RO, Ertl R, Mandal R, Bjorndahl TC, Syngelaki A, Han B, Dong E, Liu PB, Alpay-Savasan Z, Wishart DS, Nicolaides KH: Metabolomic prediction of fetal congenital heart defect in the first trimester. Am J Obstet Gynecol. 2014 Sep;211(3):240.e1-240.e14. doi: 10.1016/j.ajog.2014.03.056. Epub 2014 Apr 1. [PubMed:24704061 ]
Glutaric aciduria II
Domizio S, Romanelli A, Brindisino P, Puglielli C, Conte E, Domizio R, Sgarrella MC, Sabatino G: Glutaric aciduria type II: a case report. Int J Immunopathol Pharmacol. 2005 Oct-Dec;18(4):805-8. [PubMed:16388731 ]
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.

Associated OMIM IDs

231680 (Glutaric aciduria II)
601665 (Obesity)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023928

KNApSAcK ID

Not Available

Chemspider ID

4952667

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

2614398

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6450015

PDB ID

Not Available

ChEBI ID

84098

Food Biomarker Ontology

Not Available

VMH ID

LNLCCRN

MarkerDB ID

MDB00029888

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Reuter SE, Evans AM, Faull RJ, Chace DH, Fornasini G: Impact of haemodialysis on individual endogenous plasma acylcarnitine concentrations in end-stage renal disease. Ann Clin Biochem. 2005 Sep;42(Pt 5):387-93. [PubMed:16168195 ]
Gempel K, Kiechl S, Hofmann S, Lochmuller H, Kiechl-Kohlendorfer U, Willeit J, Sperl W, Rettinger A, Bieger I, Pongratz D, Gerbitz KD, Bauer MF: Screening for carnitine palmitoyltransferase II deficiency by tandem mass spectrometry. J Inherit Metab Dis. 2002 Feb;25(1):17-27. [PubMed:11999976 ]
Shen JJ, Matern D, Millington DS, Hillman S, Feezor MD, Bennett MJ, Qumsiyeh M, Kahler SG, Chen YT, Van Hove JL: Acylcarnitines in fibroblasts of patients with long-chain 3-hydroxyacyl-CoA dehydrogenase deficiency and other fatty acid oxidation disorders. J Inherit Metab Dis. 2000 Feb;23(1):27-44. [PubMed:10682306 ]
Spiekerkoetter U, Tokunaga C, Wendel U, Mayatepek E, Exil V, Duran M, Wijburg FA, Wanders RJ, Strauss AW: Changes in blood carnitine and acylcarnitine profiles of very long-chain acyl-CoA dehydrogenase-deficient mice subjected to stress. Eur J Clin Invest. 2004 Mar;34(3):191-6. [PubMed:15025677 ]
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 ]

Showing metabocard for Linoleyl carnitine (HMDB0006469)

MOL for HMDB0006469 (Linoleyl carnitine)

3D MOL for HMDB0006469 (Linoleyl carnitine)

3D SDF for HMDB0006469 (Linoleyl carnitine)

3D-SDF for HMDB0006469 (Linoleyl carnitine)

PDB for HMDB0006469 (Linoleyl carnitine)

3D PDB for HMDB0006469 (Linoleyl carnitine)

SMILES for HMDB0006469 (Linoleyl carnitine)

INCHI for HMDB0006469 (Linoleyl carnitine)

Structure for HMDB0006469 (Linoleyl carnitine)

3D Structure for HMDB0006469 (Linoleyl carnitine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra