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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2010-02-22 11:49:49 UTC

Update Date

2022-10-24 19:44:13 UTC

HMDB ID

HMDB0013334

Secondary Accession Numbers

HMDB13334

Metabolite Identification

Common Name

9,12-Hexadecadienoylcarnitine

Description

9,12-Hexadecadienoylcarnitine is an acylcarnitine. More specifically, it is an 9,12-hexadecadienoic acid ester of carnitine. Acylcarnitines were first discovered more than 70 year ago (PMID: 13825279 ). It is believed that there are more than 1000 types of acylcarnitines in the human body. The general role of acylcarnitines is to transport acyl-groups (organic acids and fatty acids) from the cytoplasm into the mitochondria so that they can be broken down to produce energy. This process is known as beta-oxidation. According to a recent review (PMID: 35710135 ), acylcarnitines (ACs) can be classified into 9 different categories depending on the type and size of their acyl-group: 1) short-chain ACs; 2) medium-chain ACs; 3) long-chain ACs; 4) very long-chain ACs; 5) hydroxy ACs; 6) branched chain ACs; 7) unsaturated ACs; 8) dicarboxylic ACs and 9) miscellaneous ACs. Short-chain ACs have acyl-groups with two to five carbons (C2-C5), medium-chain ACs have acyl-groups with six to thirteen carbons (C6-C13), long-chain ACs have acyl-groups with fourteen to twenty once carbons (C14-C21) and very long-chain ACs have acyl groups with more than 22 carbons. 9,12-Hexadecadienoylcarnitine is therefore classified as a long chain AC. As a long-chain acylcarnitine 9,12-hexadecadienoylcarnitine is generally formed through esterification with long-chain fatty acids obtained from the diet. The main function of most long-chain acylcarnitines is to ensure long chain fatty acid transport into the mitochondria (PMID: 22804748 ). Altered levels of long-chain acylcarnitines can serve as useful markers for inherited disorders of long-chain fatty acid metabolism. Carnitine palmitoyltransferase I (CPT I, EC:2.3.1.21) is involved in the synthesis of long-chain acylcarnitines (more than C12) on the mitochondrial outer membrane. Elevated serum/plasma levels of long-chain acylcarnitines are not only markers for incomplete FA oxidation but also are indicators of altered carbohydrate and lipid metabolism. High serum concentrations of long-chain acylcarnitines in the postprandial or fed state are markers of insulin resistance and arise from insulin's inability to inhibit CPT-1-dependent fatty acid metabolism in muscles and the heart (PMID: 19073774 ). Increased intracellular content of long-chain acylcarnitines is thought to serve as a feedback inhibition mechanism of insulin action (PMID: 23258903 ). In healthy subjects, increased concentrations of insulin effectively inhibits long-chain acylcarnitine production. Several studies have also found increased levels of circulating long-chain acylcarnitines in chronic heart failure patients (PMID: 26796394 ). The study of acylcarnitines is an active area of research and it is likely that many novel acylcarnitines will be discovered in the coming years. It is also likely that many novel roles in health and disease will be uncovered. An excellent review of the current state of knowledge for acylcarnitines is available (PMID: 35710135 ).

Structure

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


  Mrv1652307191923532D          

 28 27  0  0  0  0            999 V2000
 9994.6226 9999.7907    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9995.3366 9999.3774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0506 9999.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7646 9999.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4787 9999.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1927 9999.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9067 9999.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6207 9999.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3351 9999.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0487 9999.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.7643 9999.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.5893 9999.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.3029 9999.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.0165 9999.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.8414 9999.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.5550 9999.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.2686 9999.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.9843 9999.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.050610000.6151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.622610000.6151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.908610001.0255    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
 9993.190510000.6130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.908610001.8504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.055610001.5184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.9169 9999.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.9169 9998.5428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.6309 9998.1295    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
 9993.2029 9998.1295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 20  1  6  0  0  0
  1 25  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 19  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
M  CHG  2  21   1  27  -1
M  END

HMDB0013334
     RDKit          3D
9,12-Hexadecadienoylcarnitine
 70 69  0  0  0  0  0  0  0  0999 V2000
    8.4629    3.5022   -0.2348 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3796    2.0449    0.1030 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4229    1.8882    1.2775 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3033    0.4810    1.6593 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1851   -0.1751    1.6282 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8746    0.3975    1.2025 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4133   -0.4003    0.0677 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2896   -1.0782    0.0603 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3860   -1.0995    1.1998 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0432   -0.5476    0.9825 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0569   -1.1489    0.0674 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3365   -1.2993   -1.3581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8127   -1.8023   -2.1637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3456   -3.1346   -1.9949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9028   -3.6189   -0.7112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9896   -2.7528   -0.2177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5076   -3.1016    0.8981 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4925   -1.6336   -0.8196 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5637   -0.8596   -0.2414 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7150   -0.9834   -1.1855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3647   -0.4826   -2.5224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2973   -0.3517   -3.3628 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1019   -0.1524   -2.9149 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1247    0.5387   -0.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0266    1.4844    0.4765 N   0  0  0  0  0  4  0  0  0  0  0  0
   -5.5122    2.3350   -0.6292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1760    1.0039    1.1595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3176    2.4558    1.3470 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1148    3.6664   -1.2636 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8883    4.1197    0.4856 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5323    3.8083   -0.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3607    1.6487    0.4382 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0588    1.4815   -0.7720 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5222    2.4809    1.2054 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0020    2.3774    2.1392 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2036   -0.0704    1.9956 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1436   -1.2315    1.9260 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2606    0.4587    2.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9667    1.4552    0.8356 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0686   -0.4125   -0.8156 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0965   -1.6392   -0.8459 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8499   -0.6967    2.1456 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2991   -2.2234    1.5013 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1356    0.5761    0.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4909   -0.4550    1.9918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2921   -2.0868    0.5780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8637   -0.4522    0.1302 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6789   -0.3199   -1.7633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1555   -2.0643   -1.5655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6566   -1.0427   -2.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5353   -1.5976   -3.2656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5707   -3.9188   -2.3625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1335   -3.2819   -2.8364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4267   -4.6542   -0.9430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1668   -3.8822    0.0297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8628   -1.3513    0.7182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6657   -0.5310   -0.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8801   -2.1052   -1.3319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8945    0.4353   -3.7110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6991    0.9861   -1.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2152    0.5592    0.6357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3730    1.8148   -1.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7932    3.3393   -0.2245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6806    2.3949   -1.3498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1249    1.2771    0.6415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2653    1.5497    2.1557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1627   -0.0601    1.4604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6088    1.9452    2.0083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1092    3.0056    1.8768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7515    3.1876    0.7388 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  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  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
  5 37  1  0
  6 38  1  0
  6 39  1  0
  7 40  1  0
  8 41  1  0
  9 42  1  0
  9 43  1  0
 10 44  1  0
 10 45  1  0
 11 46  1  0
 11 47  1  0
 12 48  1  0
 12 49  1  0
 13 50  1  0
 13 51  1  0
 14 52  1  0
 14 53  1  0
 15 54  1  0
 15 55  1  0
 19 56  1  1
 20 57  1  0
 20 58  1  0
 23 59  1  0
 24 60  1  0
 24 61  1  0
 26 62  1  0
 26 63  1  0
 26 64  1  0
 27 65  1  0
 27 66  1  0
 27 67  1  0
 28 68  1  0
 28 69  1  0
 28 70  1  0
M  CHG  1  25   1
M  END


  Mrv1652307191923532D          

 28 27  0  0  0  0            999 V2000
 9994.6226 9999.7907    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9995.3366 9999.3774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0506 9999.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7646 9999.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4787 9999.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1927 9999.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9067 9999.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6207 9999.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3351 9999.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0487 9999.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.7643 9999.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.5893 9999.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.3029 9999.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.0165 9999.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.8414 9999.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.5550 9999.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.2686 9999.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.9843 9999.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.050610000.6151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.622610000.6151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.908610001.0255    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
 9993.190510000.6130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.908610001.8504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.055610001.5184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.9169 9999.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.9169 9998.5428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.6309 9998.1295    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
 9993.2029 9998.1295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 20  1  6  0  0  0
  1 25  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 19  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
M  CHG  2  21   1  27  -1
M  END
> <DATABASE_ID>
HMDB0013334

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C23H41NO4/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/h7-8,10-11,21H,5-6,9,12-20H2,1-4H3/b8-7-,11-10-/t21-/m1/s1

> <INCHI_KEY>
CMVGCHSJDXKPBB-ROVXQSMVSA-N

> <FORMULA>
C23H41NO4

> <MOLECULAR_WEIGHT>
395.584

> <EXACT_MASS>
395.303558804

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
47.6844175432321

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
0.76

> <JCHEM_LOGP>
1.3097045408615875

> <ALOGPS_LOGS>
-7.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.216763902737658

> <JCHEM_PKA_STRONGEST_BASIC>
-7.0571868920224

> <JCHEM_POLAR_SURFACE_AREA>
66.43

> <JCHEM_REFRACTIVITY>
139.3099

> <JCHEM_ROTATABLE_BOND_COUNT>
18

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.59e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-3-[(9Z,12Z)-hexadeca-9,12-dienoyloxy]-4-(trimethylammonio)butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013334
     RDKit          3D
9,12-Hexadecadienoylcarnitine
 70 69  0  0  0  0  0  0  0  0999 V2000
    8.4629    3.5022   -0.2348 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3796    2.0449    0.1030 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4229    1.8882    1.2775 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3033    0.4810    1.6593 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1851   -0.1751    1.6282 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8746    0.3975    1.2025 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4133   -0.4003    0.0677 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2896   -1.0782    0.0603 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3860   -1.0995    1.1998 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0432   -0.5476    0.9825 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0569   -1.1489    0.0674 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3365   -1.2993   -1.3581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8127   -1.8023   -2.1637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3456   -3.1346   -1.9949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9028   -3.6189   -0.7112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9896   -2.7528   -0.2177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5076   -3.1016    0.8981 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4925   -1.6336   -0.8196 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5637   -0.8596   -0.2414 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7150   -0.9834   -1.1855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3647   -0.4826   -2.5224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2973   -0.3517   -3.3628 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1019   -0.1524   -2.9149 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1247    0.5387   -0.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0266    1.4844    0.4765 N   0  0  0  0  0  4  0  0  0  0  0  0
   -5.5122    2.3350   -0.6292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1760    1.0039    1.1595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3176    2.4558    1.3470 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1148    3.6664   -1.2636 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8883    4.1197    0.4856 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5323    3.8083   -0.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3607    1.6487    0.4382 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0588    1.4815   -0.7720 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5222    2.4809    1.2054 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0020    2.3774    2.1392 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2036   -0.0704    1.9956 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1436   -1.2315    1.9260 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2606    0.4587    2.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9667    1.4552    0.8356 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0686   -0.4125   -0.8156 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0965   -1.6392   -0.8459 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8499   -0.6967    2.1456 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2991   -2.2234    1.5013 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1356    0.5761    0.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4909   -0.4550    1.9918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2921   -2.0868    0.5780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8637   -0.4522    0.1302 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6789   -0.3199   -1.7633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1555   -2.0643   -1.5655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6566   -1.0427   -2.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5353   -1.5976   -3.2656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5707   -3.9188   -2.3625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1335   -3.2819   -2.8364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4267   -4.6542   -0.9430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1668   -3.8822    0.0297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8628   -1.3513    0.7182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6657   -0.5310   -0.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8801   -2.1052   -1.3319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8945    0.4353   -3.7110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6991    0.9861   -1.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2152    0.5592    0.6357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3730    1.8148   -1.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7932    3.3393   -0.2245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6806    2.3949   -1.3498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1249    1.2771    0.6415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2653    1.5497    2.1557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1627   -0.0601    1.4604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6088    1.9452    2.0083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1092    3.0056    1.8768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7515    3.1876    0.7388 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  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  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
  5 37  1  0
  6 38  1  0
  6 39  1  0
  7 40  1  0
  8 41  1  0
  9 42  1  0
  9 43  1  0
 10 44  1  0
 10 45  1  0
 11 46  1  0
 11 47  1  0
 12 48  1  0
 12 49  1  0
 13 50  1  0
 13 51  1  0
 14 52  1  0
 14 53  1  0
 15 54  1  0
 15 55  1  0
 19 56  1  1
 20 57  1  0
 20 58  1  0
 23 59  1  0
 24 60  1  0
 24 61  1  0
 26 62  1  0
 26 63  1  0
 26 64  1  0
 27 65  1  0
 27 66  1  0
 27 67  1  0
 28 68  1  0
 28 69  1  0
 28 70  1  0
M  CHG  1  25   1
M  END

HEADER    PROTEIN                                 19-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUL-19         0                                  
HETATM    1  C   UNK     0    8656.6298666.276   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8657.9628665.504   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8659.2948666.276   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8660.6278665.504   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8661.9608666.276   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8663.2938665.504   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8664.6268666.276   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8665.9598665.504   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8667.2928666.276   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8668.6248665.504   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8669.9608666.276   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8671.5008666.276   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8672.8328665.504   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8674.1648666.276   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8675.7048666.276   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8677.0368665.504   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8678.3688666.276   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8679.7048665.504   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0    8659.2948667.815   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0    8656.6298667.815   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0    8655.2968668.581   0.000  0.00  0.00           N+1
HETATM   22  C   UNK     0    8653.9568667.811   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8655.2968670.121   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8653.7048669.501   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8655.3128665.485   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8655.3128663.947   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0    8656.6448663.175   0.000  0.00  0.00           O-1
HETATM   28  O   UNK     0    8653.9798663.175   0.000  0.00  0.00           O+0
CONECT    1    2   20   25                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19    3                                                            
CONECT   20    1   21                                                       
CONECT   21   20   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21                                                            
CONECT   25    1   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   54    0
END

COMPND    HMDB0013334
HETATM    1  C1  UNL     1       8.463   3.502  -0.235  1.00  0.00           C  
HETATM    2  C2  UNL     1       8.380   2.045   0.103  1.00  0.00           C  
HETATM    3  C3  UNL     1       7.423   1.888   1.277  1.00  0.00           C  
HETATM    4  C4  UNL     1       7.303   0.481   1.659  1.00  0.00           C  
HETATM    5  C5  UNL     1       6.185  -0.175   1.628  1.00  0.00           C  
HETATM    6  C6  UNL     1       4.875   0.397   1.202  1.00  0.00           C  
HETATM    7  C7  UNL     1       4.413  -0.400   0.068  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.290  -1.078   0.060  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.386  -1.100   1.200  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.043  -0.548   0.982  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.057  -1.149   0.067  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.336  -1.299  -1.358  1.00  0.00           C  
HETATM   13  C13 UNL     1      -0.813  -1.802  -2.164  1.00  0.00           C  
HETATM   14  C14 UNL     1      -1.346  -3.135  -1.995  1.00  0.00           C  
HETATM   15  C15 UNL     1      -1.903  -3.619  -0.711  1.00  0.00           C  
HETATM   16  C16 UNL     1      -2.990  -2.753  -0.218  1.00  0.00           C  
HETATM   17  O1  UNL     1      -3.508  -3.102   0.898  1.00  0.00           O  
HETATM   18  O2  UNL     1      -3.493  -1.634  -0.820  1.00  0.00           O  
HETATM   19  C17 UNL     1      -4.564  -0.860  -0.241  1.00  0.00           C  
HETATM   20  C18 UNL     1      -5.715  -0.983  -1.185  1.00  0.00           C  
HETATM   21  C19 UNL     1      -5.365  -0.483  -2.522  1.00  0.00           C  
HETATM   22  O3  UNL     1      -6.297  -0.352  -3.363  1.00  0.00           O  
HETATM   23  O4  UNL     1      -4.102  -0.152  -2.915  1.00  0.00           O  
HETATM   24  C20 UNL     1      -4.125   0.539  -0.071  1.00  0.00           C  
HETATM   25  N1  UNL     1      -5.027   1.484   0.476  1.00  0.00           N1+
HETATM   26  C21 UNL     1      -5.512   2.335  -0.629  1.00  0.00           C  
HETATM   27  C22 UNL     1      -6.176   1.004   1.160  1.00  0.00           C  
HETATM   28  C23 UNL     1      -4.318   2.456   1.347  1.00  0.00           C  
HETATM   29  H1  UNL     1       8.115   3.666  -1.264  1.00  0.00           H  
HETATM   30  H2  UNL     1       7.888   4.120   0.486  1.00  0.00           H  
HETATM   31  H3  UNL     1       9.532   3.808  -0.174  1.00  0.00           H  
HETATM   32  H4  UNL     1       9.361   1.649   0.438  1.00  0.00           H  
HETATM   33  H5  UNL     1       8.059   1.482  -0.772  1.00  0.00           H  
HETATM   34  H6  UNL     1       6.522   2.481   1.205  1.00  0.00           H  
HETATM   35  H7  UNL     1       8.002   2.377   2.139  1.00  0.00           H  
HETATM   36  H8  UNL     1       8.204  -0.070   1.996  1.00  0.00           H  
HETATM   37  H9  UNL     1       6.144  -1.232   1.926  1.00  0.00           H  
HETATM   38  H10 UNL     1       4.261   0.459   2.088  1.00  0.00           H  
HETATM   39  H11 UNL     1       4.967   1.455   0.836  1.00  0.00           H  
HETATM   40  H12 UNL     1       5.069  -0.412  -0.816  1.00  0.00           H  
HETATM   41  H13 UNL     1       3.096  -1.639  -0.846  1.00  0.00           H  
HETATM   42  H14 UNL     1       2.850  -0.697   2.146  1.00  0.00           H  
HETATM   43  H15 UNL     1       2.299  -2.223   1.501  1.00  0.00           H  
HETATM   44  H16 UNL     1       1.136   0.576   0.730  1.00  0.00           H  
HETATM   45  H17 UNL     1       0.491  -0.455   1.992  1.00  0.00           H  
HETATM   46  H18 UNL     1      -0.292  -2.087   0.578  1.00  0.00           H  
HETATM   47  H19 UNL     1      -0.864  -0.452   0.130  1.00  0.00           H  
HETATM   48  H20 UNL     1       0.679  -0.320  -1.763  1.00  0.00           H  
HETATM   49  H21 UNL     1       1.155  -2.064  -1.565  1.00  0.00           H  
HETATM   50  H22 UNL     1      -1.657  -1.043  -2.042  1.00  0.00           H  
HETATM   51  H23 UNL     1      -0.535  -1.598  -3.266  1.00  0.00           H  
HETATM   52  H24 UNL     1      -0.571  -3.919  -2.363  1.00  0.00           H  
HETATM   53  H25 UNL     1      -2.134  -3.282  -2.836  1.00  0.00           H  
HETATM   54  H26 UNL     1      -2.427  -4.654  -0.943  1.00  0.00           H  
HETATM   55  H27 UNL     1      -1.167  -3.882   0.030  1.00  0.00           H  
HETATM   56  H28 UNL     1      -4.863  -1.351   0.718  1.00  0.00           H  
HETATM   57  H29 UNL     1      -6.666  -0.531  -0.823  1.00  0.00           H  
HETATM   58  H30 UNL     1      -5.880  -2.105  -1.332  1.00  0.00           H  
HETATM   59  H31 UNL     1      -3.895   0.435  -3.711  1.00  0.00           H  
HETATM   60  H32 UNL     1      -3.699   0.986  -1.011  1.00  0.00           H  
HETATM   61  H33 UNL     1      -3.215   0.559   0.636  1.00  0.00           H  
HETATM   62  H34 UNL     1      -6.373   1.815  -1.068  1.00  0.00           H  
HETATM   63  H35 UNL     1      -5.793   3.339  -0.225  1.00  0.00           H  
HETATM   64  H36 UNL     1      -4.681   2.395  -1.350  1.00  0.00           H  
HETATM   65  H37 UNL     1      -7.125   1.277   0.642  1.00  0.00           H  
HETATM   66  H38 UNL     1      -6.265   1.550   2.156  1.00  0.00           H  
HETATM   67  H39 UNL     1      -6.163  -0.060   1.460  1.00  0.00           H  
HETATM   68  H40 UNL     1      -3.609   1.945   2.008  1.00  0.00           H  
HETATM   69  H41 UNL     1      -5.109   3.006   1.877  1.00  0.00           H  
HETATM   70  H42 UNL     1      -3.752   3.188   0.739  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3   32   33
CONECT    3    4   34   35
CONECT    4    5    5   36
CONECT    5    6   37
CONECT    6    7   38   39
CONECT    7    8    8   40
CONECT    8    9   41
CONECT    9   10   42   43
CONECT   10   11   44   45
CONECT   11   12   46   47
CONECT   12   13   48   49
CONECT   13   14   50   51
CONECT   14   15   52   53
CONECT   15   16   54   55
CONECT   16   17   17   18
CONECT   18   19
CONECT   19   20   24   56
CONECT   20   21   57   58
CONECT   21   22   22   23
CONECT   23   59
CONECT   24   25   60   61
CONECT   25   26   27   28
CONECT   26   62   63   64
CONECT   27   65   66   67
CONECT   28   68   69   70
END

HMDB0013334
     RDKit          3D
9,12-Hexadecadienoylcarnitine
 70 69  0  0  0  0  0  0  0  0999 V2000
    8.4629    3.5022   -0.2348 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3796    2.0449    0.1030 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4229    1.8882    1.2775 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3033    0.4810    1.6593 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1851   -0.1751    1.6282 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8746    0.3975    1.2025 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4133   -0.4003    0.0677 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2896   -1.0782    0.0603 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3860   -1.0995    1.1998 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0432   -0.5476    0.9825 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0569   -1.1489    0.0674 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3365   -1.2993   -1.3581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8127   -1.8023   -2.1637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3456   -3.1346   -1.9949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9028   -3.6189   -0.7112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9896   -2.7528   -0.2177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5076   -3.1016    0.8981 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4925   -1.6336   -0.8196 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5637   -0.8596   -0.2414 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7150   -0.9834   -1.1855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3647   -0.4826   -2.5224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2973   -0.3517   -3.3628 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1019   -0.1524   -2.9149 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1247    0.5387   -0.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0266    1.4844    0.4765 N   0  0  0  0  0  4  0  0  0  0  0  0
   -5.5122    2.3350   -0.6292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1760    1.0039    1.1595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3176    2.4558    1.3470 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1148    3.6664   -1.2636 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8883    4.1197    0.4856 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5323    3.8083   -0.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3607    1.6487    0.4382 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0588    1.4815   -0.7720 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5222    2.4809    1.2054 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0020    2.3774    2.1392 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2036   -0.0704    1.9956 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1436   -1.2315    1.9260 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2606    0.4587    2.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9667    1.4552    0.8356 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0686   -0.4125   -0.8156 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0965   -1.6392   -0.8459 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8499   -0.6967    2.1456 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2991   -2.2234    1.5013 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1356    0.5761    0.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4909   -0.4550    1.9918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2921   -2.0868    0.5780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8637   -0.4522    0.1302 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6789   -0.3199   -1.7633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1555   -2.0643   -1.5655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6566   -1.0427   -2.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5353   -1.5976   -3.2656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5707   -3.9188   -2.3625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1335   -3.2819   -2.8364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4267   -4.6542   -0.9430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1668   -3.8822    0.0297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8628   -1.3513    0.7182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6657   -0.5310   -0.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8801   -2.1052   -1.3319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8945    0.4353   -3.7110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6991    0.9861   -1.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2152    0.5592    0.6357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3730    1.8148   -1.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7932    3.3393   -0.2245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6806    2.3949   -1.3498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1249    1.2771    0.6415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2653    1.5497    2.1557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1627   -0.0601    1.4604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6088    1.9452    2.0083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1092    3.0056    1.8768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7515    3.1876    0.7388 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  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  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
  5 37  1  0
  6 38  1  0
  6 39  1  0
  7 40  1  0
  8 41  1  0
  9 42  1  0
  9 43  1  0
 10 44  1  0
 10 45  1  0
 11 46  1  0
 11 47  1  0
 12 48  1  0
 12 49  1  0
 13 50  1  0
 13 51  1  0
 14 52  1  0
 14 53  1  0
 15 54  1  0
 15 55  1  0
 19 56  1  1
 20 57  1  0
 20 58  1  0
 23 59  1  0
 24 60  1  0
 24 61  1  0
 26 62  1  0
 26 63  1  0
 26 64  1  0
 27 65  1  0
 27 66  1  0
 27 67  1  0
 28 68  1  0
 28 69  1  0
 28 70  1  0
M  CHG  1  25   1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(Z,Z)9,12-Hexadecadienoylcarnitine	HMDB
9(Z),12(Z)-Hexadecadienoylcarnitine	HMDB
9,12-Hexadecadienylcarnitine	HMDB
9Z,12Z-Hexadecadienoylcarnitine	HMDB
Acyl carnitine C16:2	HMDB
Hexadecadienyl-L-carnitine	HMDB
(3R)-3-[(9Z,12Z)-Hexadeca-9,12-dienoyloxy]-4-(trimethylazaniumyl)butanoic acid	HMDB

Chemical Formula

C₂₃H₄₂NO₄

Average Molecular Weight

396.591

Monoisotopic Molecular Weight

396.310835257

IUPAC Name

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

Traditional Name

(3R)-3-[(9Z,12Z)-hexadeca-9,12-dienoyloxy]-4-(trimethylammonio)butanoate

CAS Registry Number

1911579-97-9

SMILES

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

InChI Identifier

InChI=1S/C23H41NO4/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/h7-8,10-11,21H,5-6,9,12-20H2,1-4H3/p+1/b8-7-,11-10-/t21-/m1/s1

InChI Key

CMVGCHSJDXKPBB-ROVXQSMVSA-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 salt
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic salt
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Health effect

Cancer

Breast cancer (PMID: 35710135)

Diabetes mellitus type 2 (PMID: 35710135)
Celiac disease (PMID: 35710135)
Inflammatory bowel disease (PMID: 35710135)

Circulatory system disorder

Cardiac disorder

Cardiovascular disease (PMID: 35710135)
Heart failure (PMID: 35710135)

Renal system and urinary system

Renal disorder

Renal cell carcinoma (PMID: 35710135)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21359215)
Saliva (HMDB: HMDB0013334)

Excreta

Biofluid or Excreta

Urine (PMID: 24023812)
Feces (PMID: 27624970)

Cellular substructure

Organelle

peroxisome (PMID: 35710135)

Cell

All cells and tissues (PMID: 35710135)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
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)

Equine

Horse (FooDB: FOOD00378)

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)

Process

Not Available

Role

Biological role

Energy source (PMID: 35710135)

Industrial application

Pharmaceutical industry

Biomarker

Physical Properties

State

Solid

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.6e-05 g/L	ALOGPS
logP	0.76	ALOGPS
logP	1.31	ChemAxon
logS	-7.4	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	18	ChemAxon
Refractivity	139.31 m³·mol⁻¹	ChemAxon
Polarizability	47.68 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]+	203.194	30932474
DeepCCS	[M-H]-	200.043	30932474
DeepCCS	[M-2H]-	235.592	30932474
DeepCCS	[M+Na]+	211.881	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
9,12-Hexadecadienoylcarnitine	CCC\C=C/C\C=C/CCCCCCCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C	3596.5	Standard polar	33892256
9,12-Hexadecadienoylcarnitine	CCC\C=C/C\C=C/CCCCCCCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C	2422.9	Standard non polar	33892256
9,12-Hexadecadienoylcarnitine	CCC\C=C/C\C=C/CCCCCCCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C	2725.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
9,12-Hexadecadienoylcarnitine,1TMS,isomer #1	CCC/C=C\C/C=C\CCCCCCCC(=O)O[C@H](CC(=O)O[Si](C)(C)C)C[N+](C)(C)C	2769.5	Semi standard non polar	33892256
9,12-Hexadecadienoylcarnitine,1TBDMS,isomer #1	CCC/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	3001.5	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 - 9,12-Hexadecadienoylcarnitine 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 - 9,12-Hexadecadienoylcarnitine 10V, Positive-QTOF	splash10-0002-0009000000-8f0fc69f96bfd61e7cfa	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9,12-Hexadecadienoylcarnitine 20V, Positive-QTOF	splash10-000j-9005000000-a5dcc70637f039e125e8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9,12-Hexadecadienoylcarnitine 40V, Positive-QTOF	splash10-000i-9000000000-e9262cbaff8cb4ad0ba6	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces
Saliva
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.01 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	0.0080-0.0250 uM	Adult (>18 years old)	Both	Normal	Molecular You	details
Feces	Detected and Quantified	0.19 +/- 0.09 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Feces	Detected and Quantified	0.11 +/- 0.04 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Saliva	Detected and Quantified	0.011 +/- 0.002 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	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	0.0010 (0.0005-0.0040) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.011 (0.0057) uM	Adult (>18 years old)	Female	Pregnancy with fetus having congenital heart defect	24704061	details

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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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

Okun JG, Kolker S, Schulze A, Kohlmuller D, Olgemoller K, Lindner M, Hoffmann GF, Wanders RJ, Mayatepek E: A method for quantitative acylcarnitine profiling in human skin fibroblasts using unlabelled palmitic acid: diagnosis of fatty acid oxidation disorders and differentiation between biochemical phenotypes of MCAD deficiency. Biochim Biophys Acta. 2002 Oct 10;1584(2-3):91-8. [PubMed:12385891 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
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Showing metabocard for 9,12-Hexadecadienoylcarnitine (HMDB0013334)

MOL for HMDB0013334 (9,12-Hexadecadienoylcarnitine)

3D MOL for HMDB0013334 (9,12-Hexadecadienoylcarnitine)

3D SDF for HMDB0013334 (9,12-Hexadecadienoylcarnitine)

3D-SDF for HMDB0013334 (9,12-Hexadecadienoylcarnitine)

PDB for HMDB0013334 (9,12-Hexadecadienoylcarnitine)

3D PDB for HMDB0013334 (9,12-Hexadecadienoylcarnitine)

SMILES for HMDB0013334 (9,12-Hexadecadienoylcarnitine)

INCHI for HMDB0013334 (9,12-Hexadecadienoylcarnitine)

Structure for HMDB0013334 (9,12-Hexadecadienoylcarnitine)

3D Structure for HMDB0013334 (9,12-Hexadecadienoylcarnitine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra