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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-02-24 01:48:23 UTC

Update Date

2022-10-24 19:44:18 UTC

HMDB ID

HMDB0240780

Secondary Accession Numbers

None

Metabolite Identification

Common Name

O-Linoleoylcarnitine

Description

O-Linoleoylcarnitine is an acylcarnitine. More specifically, it is an linoleic 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. O-Linoleoylcarnitine is therefore classified as a long chain AC. As a long-chain acylcarnitine O-Linoleoylcarnitine is generally formed through esterification with long-chain fatty acids obtained from the diet. The main function of most long-chain acylcarnitines is to ensure long chain fatty acid transport into the mitochondria (PMID: 22804748 ). Altered levels of long-chain acylcarnitines can serve as useful markers for inherited disorders of long-chain fatty acid metabolism. In particular O-Linoleoylcarnitine is elevated in the blood or plasma of individuals with Parkinson disease (PMID: 29294246 ), chronic heart failure (PMID: 26796394 , PMID: 27473038 ), carnitine/acylcarnitine translocase (CACT) deficiency (PMID: 15057979 ), and ischaemia/reperfusion (PMID: 26936967 , PMID: 22607863 , PMID: 24468136 ). 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


  Mrv1652310061800322D          

 34 33  0  0  0  0            999 V2000
    0.6632    5.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947    1.2079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2697    2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9197    2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6632    4.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3776    4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3776    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921    2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066    1.6204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5211    2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    1.6204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5224    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2368    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802    4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947    4.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947    2.0329    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   12.0947    5.3329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8092    4.0954    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    9.9513    4.0954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3776    1.6204    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066    0.7954    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    0.7954    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    1.6204    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  2  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
 23 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 21  1  0  0  0  0
 25 20  1  0  0  0  0
 26  2  1  0  0  0  0
 26  3  1  0  0  0  0
 26  4  1  0  0  0  0
 26 22  1  0  0  0  0
 27 24  2  0  0  0  0
 28 24  1  0  0  0  0
 29 25  2  0  0  0  0
 30 23  1  0  0  0  0
 30 25  1  0  0  0  0
 31  9  1  0  0  0  0
 32 10  1  0  0  0  0
 33 12  1  0  0  0  0
 34 13  1  0  0  0  0
M  CHG  2  26   1  28  -1
M  END

HMDB0240780
     RDKit          3D
O-Linoleoylcarnitine
 75 74  0  0  0  0  0  0  0  0999 V2000
    7.5494   -2.0290    1.8948 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9790   -2.1100    0.4601 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0077   -2.6803   -0.4906 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7137   -2.0486   -0.7112 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7479   -1.8952    0.4002 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5211   -1.2351   -0.1075 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0219   -0.0749    0.3137 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6374    0.7041    1.3515 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1706    2.0302    1.1438 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2173    2.7850    0.1070 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7067    2.5081   -1.2368 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7783    3.5833   -1.7185 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5868    3.9279   -0.9382 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5745    2.8674   -0.7190 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0824    2.3594   -2.0663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9536    1.2690   -1.9320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1642    1.7330   -1.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1843    0.6619   -1.0529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9064   -0.4532   -1.5703 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3782    0.8160   -0.4143 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3253   -0.3275   -0.3388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5046    0.2094   -1.0848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6678   -0.6165   -1.2647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7299   -0.4507   -0.6316 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6416   -1.6682   -2.1893 O   0  0  0  0  0  1  0  0  0  0  0  0
   -5.4842   -0.6113    1.1082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2585   -1.6963    1.5573 N   0  0  0  0  0  4  0  0  0  0  0  0
   -7.5363   -1.2948    2.1289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5157   -2.2912    2.7234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4679   -2.7934    0.6660 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2251   -1.0196    2.2214 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8386   -2.8280    2.1780 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4418   -2.2345    2.5790 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4405   -1.1481    0.1097 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8716   -2.8123    0.4536 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8645   -3.7667   -0.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5700   -2.8161   -1.4707 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1784   -2.5830   -1.5542 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8948   -1.0232   -1.1628 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3827   -2.9441    0.6935 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1171   -1.4785    1.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9579   -1.7541   -0.9197 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0654    0.2214   -0.1815 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8027    0.8636    2.1614 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3470    0.0759    1.9522 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6339    2.4846    2.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7065    3.7835    0.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6356    2.6366   -1.9206 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3956    1.5000   -1.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4841    3.2744   -2.7655 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4164    4.4978   -1.8913 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8457    4.4573    0.0240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0450    4.7525   -1.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8229    2.0468   -0.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3005    3.3878   -0.2060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3805    3.2073   -2.6138 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9271    1.9677   -2.6583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2727    1.0122   -2.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4901    0.3695   -1.4719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6466    2.5277   -1.8284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9410    2.1881   -0.2164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8083   -1.1303   -0.8680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8033    1.1919   -0.6189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1218    0.4809   -2.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8659    0.3220    1.6314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4329   -0.7175    1.5412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5447   -1.4615    3.2161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3733   -1.9127    1.6931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7127   -0.2052    1.9570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4338   -2.1615    2.5656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8333   -3.3459    2.8501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7938   -1.7501    3.6468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9452   -2.6692   -0.2852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2251   -3.7815    1.1442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5617   -2.8845    0.4401 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  0
 22 63  1  0
 22 64  1  0
 26 65  1  0
 26 66  1  0
 28 67  1  0
 28 68  1  0
 28 69  1  0
 29 70  1  0
 29 71  1  0
 29 72  1  0
 30 73  1  0
 30 74  1  0
 30 75  1  0
M  CHG  2  25  -1  27   1
M  END


  Mrv1652310061800322D          

 34 33  0  0  0  0            999 V2000
    0.6632    5.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947    1.2079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2697    2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9197    2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6632    4.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3776    4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3776    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921    2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066    1.6204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5211    2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    1.6204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5224    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2368    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802    4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947    4.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947    2.0329    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   12.0947    5.3329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8092    4.0954    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    9.9513    4.0954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3776    1.6204    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066    0.7954    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    0.7954    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    1.6204    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  2  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
 23 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 21  1  0  0  0  0
 25 20  1  0  0  0  0
 26  2  1  0  0  0  0
 26  3  1  0  0  0  0
 26  4  1  0  0  0  0
 26 22  1  0  0  0  0
 27 24  2  0  0  0  0
 28 24  1  0  0  0  0
 29 25  2  0  0  0  0
 30 23  1  0  0  0  0
 30 25  1  0  0  0  0
 31  9  1  0  0  0  0
 32 10  1  0  0  0  0
 33 12  1  0  0  0  0
 34 13  1  0  0  0  0
M  CHG  2  26   1  28  -1
M  END
> <DATABASE_ID>
HMDB0240780

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]\C(CCCCC)=C(/[H])C\C([H])=C(\[H])CCCCCCCC(=O)OC(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-

> <INCHI_KEY>
MJLXQSQYKZWZCB-UTJQPWESSA-N

> <FORMULA>
C25H45NO4

> <MOLECULAR_WEIGHT>
423.638

> <EXACT_MASS>
423.334858933

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
51.263591267702665

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
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>
66.42999999999999

> <JCHEM_REFRACTIVITY>
148.5119

> <JCHEM_ROTATABLE_BOND_COUNT>
20

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.62e-06 g/l

> <JCHEM_TRADITIONAL_IUPAC>
linoelaidyl carnitine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0240780
     RDKit          3D
O-Linoleoylcarnitine
 75 74  0  0  0  0  0  0  0  0999 V2000
    7.5494   -2.0290    1.8948 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9790   -2.1100    0.4601 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0077   -2.6803   -0.4906 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7137   -2.0486   -0.7112 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7479   -1.8952    0.4002 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5211   -1.2351   -0.1075 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0219   -0.0749    0.3137 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6374    0.7041    1.3515 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1706    2.0302    1.1438 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2173    2.7850    0.1070 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7067    2.5081   -1.2368 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7783    3.5833   -1.7185 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5868    3.9279   -0.9382 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5745    2.8674   -0.7190 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0824    2.3594   -2.0663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9536    1.2690   -1.9320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1642    1.7330   -1.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1843    0.6619   -1.0529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9064   -0.4532   -1.5703 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3782    0.8160   -0.4143 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3253   -0.3275   -0.3388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5046    0.2094   -1.0848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6678   -0.6165   -1.2647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7299   -0.4507   -0.6316 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6416   -1.6682   -2.1893 O   0  0  0  0  0  1  0  0  0  0  0  0
   -5.4842   -0.6113    1.1082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2585   -1.6963    1.5573 N   0  0  0  0  0  4  0  0  0  0  0  0
   -7.5363   -1.2948    2.1289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5157   -2.2912    2.7234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4679   -2.7934    0.6660 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2251   -1.0196    2.2214 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8386   -2.8280    2.1780 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4418   -2.2345    2.5790 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4405   -1.1481    0.1097 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8716   -2.8123    0.4536 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8645   -3.7667   -0.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5700   -2.8161   -1.4707 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1784   -2.5830   -1.5542 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8948   -1.0232   -1.1628 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3827   -2.9441    0.6935 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1171   -1.4785    1.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9579   -1.7541   -0.9197 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0654    0.2214   -0.1815 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8027    0.8636    2.1614 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3470    0.0759    1.9522 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6339    2.4846    2.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7065    3.7835    0.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6356    2.6366   -1.9206 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3956    1.5000   -1.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4841    3.2744   -2.7655 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4164    4.4978   -1.8913 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8457    4.4573    0.0240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0450    4.7525   -1.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8229    2.0468   -0.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3005    3.3878   -0.2060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3805    3.2073   -2.6138 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9271    1.9677   -2.6583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2727    1.0122   -2.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4901    0.3695   -1.4719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6466    2.5277   -1.8284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9410    2.1881   -0.2164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8083   -1.1303   -0.8680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8033    1.1919   -0.6189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1218    0.4809   -2.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8659    0.3220    1.6314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4329   -0.7175    1.5412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5447   -1.4615    3.2161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3733   -1.9127    1.6931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7127   -0.2052    1.9570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4338   -2.1615    2.5656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8333   -3.3459    2.8501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7938   -1.7501    3.6468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9452   -2.6692   -0.2852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2251   -3.7815    1.1442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5617   -2.8845    0.4401 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  0
 22 63  1  0
 22 64  1  0
 26 65  1  0
 26 66  1  0
 28 67  1  0
 28 68  1  0
 28 69  1  0
 29 70  1  0
 29 71  1  0
 29 72  1  0
 30 73  1  0
 30 74  1  0
 30 75  1  0
M  CHG  2  25  -1  27   1
M  END

HEADER    PROTEIN                                 06-OCT-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-OCT-18         0                                  
HETATM    1  C   UNK     0       1.238   9.955   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      22.577   2.255   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      21.037   3.795   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      24.117   3.795   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.238   8.415   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.572   7.645   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.572   6.105   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.905   5.335   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.905   3.795   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.239   3.025   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.573   3.795   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.906   3.025   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.240   3.795   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.240   5.335   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.574   6.105   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.907   5.335   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.241   6.105   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.575   5.335   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.908   6.105   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      17.242   5.335   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      21.243   7.645   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      22.577   5.335   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      21.243   6.105   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      22.577   8.415   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      18.576   6.105   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0      22.577   3.795   0.000  0.00  0.00           N+1
HETATM   27  O   UNK     0      22.577   9.955   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      23.910   7.645   0.000  0.00  0.00           O-1
HETATM   29  O   UNK     0      18.576   7.645   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      19.909   5.335   0.000  0.00  0.00           O+0
HETATM   31  H   UNK     0       2.572   3.025   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0       5.239   1.485   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0       7.906   1.485   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0      10.574   3.025   0.000  0.00  0.00           H+0
CONECT    1    5                                                            
CONECT    2   26                                                            
CONECT    3   26                                                            
CONECT    4   26                                                            
CONECT    5    1    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   31                                                  
CONECT   10    9   11   32                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   33                                                  
CONECT   13   12   14   34                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   25                                                       
CONECT   21   23   24                                                       
CONECT   22   23   26                                                       
CONECT   23   21   22   30                                                  
CONECT   24   21   27   28                                                  
CONECT   25   20   29   30                                                  
CONECT   26    2    3    4   22                                             
CONECT   27   24                                                            
CONECT   28   24                                                            
CONECT   29   25                                                            
CONECT   30   23   25                                                       
CONECT   31    9                                                            
CONECT   32   10                                                            
CONECT   33   12                                                            
CONECT   34   13                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   66    0
END

COMPND    HMDB0240780
HETATM    1  C1  UNL     1       7.549  -2.029   1.895  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.979  -2.110   0.460  1.00  0.00           C  
HETATM    3  C3  UNL     1       7.008  -2.680  -0.491  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.714  -2.049  -0.711  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.748  -1.895   0.400  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.521  -1.235  -0.107  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.022  -0.075   0.314  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.637   0.704   1.352  1.00  0.00           C  
HETATM    9  C9  UNL     1       4.171   2.030   1.144  1.00  0.00           C  
HETATM   10  C10 UNL     1       4.217   2.785   0.107  1.00  0.00           C  
HETATM   11  C11 UNL     1       3.707   2.508  -1.237  1.00  0.00           C  
HETATM   12  C12 UNL     1       2.778   3.583  -1.718  1.00  0.00           C  
HETATM   13  C13 UNL     1       1.587   3.928  -0.938  1.00  0.00           C  
HETATM   14  C14 UNL     1       0.574   2.867  -0.719  1.00  0.00           C  
HETATM   15  C15 UNL     1       0.082   2.359  -2.066  1.00  0.00           C  
HETATM   16  C16 UNL     1      -0.954   1.269  -1.932  1.00  0.00           C  
HETATM   17  C17 UNL     1      -2.164   1.733  -1.188  1.00  0.00           C  
HETATM   18  C18 UNL     1      -3.184   0.662  -1.053  1.00  0.00           C  
HETATM   19  O1  UNL     1      -2.906  -0.453  -1.570  1.00  0.00           O  
HETATM   20  O2  UNL     1      -4.378   0.816  -0.414  1.00  0.00           O  
HETATM   21  C19 UNL     1      -5.325  -0.328  -0.339  1.00  0.00           C  
HETATM   22  C20 UNL     1      -6.505   0.209  -1.085  1.00  0.00           C  
HETATM   23  C21 UNL     1      -7.668  -0.617  -1.265  1.00  0.00           C  
HETATM   24  O3  UNL     1      -8.730  -0.451  -0.632  1.00  0.00           O  
HETATM   25  O4  UNL     1      -7.642  -1.668  -2.189  1.00  0.00           O1-
HETATM   26  C22 UNL     1      -5.484  -0.611   1.108  1.00  0.00           C  
HETATM   27  N1  UNL     1      -6.258  -1.696   1.557  1.00  0.00           N1+
HETATM   28  C23 UNL     1      -7.536  -1.295   2.129  1.00  0.00           C  
HETATM   29  C24 UNL     1      -5.516  -2.291   2.723  1.00  0.00           C  
HETATM   30  C25 UNL     1      -6.468  -2.793   0.666  1.00  0.00           C  
HETATM   31  H1  UNL     1       7.225  -1.020   2.221  1.00  0.00           H  
HETATM   32  H2  UNL     1       6.839  -2.828   2.178  1.00  0.00           H  
HETATM   33  H3  UNL     1       8.442  -2.234   2.579  1.00  0.00           H  
HETATM   34  H4  UNL     1       8.441  -1.148   0.110  1.00  0.00           H  
HETATM   35  H5  UNL     1       8.872  -2.812   0.454  1.00  0.00           H  
HETATM   36  H6  UNL     1       6.864  -3.767  -0.173  1.00  0.00           H  
HETATM   37  H7  UNL     1       7.570  -2.816  -1.471  1.00  0.00           H  
HETATM   38  H8  UNL     1       5.178  -2.583  -1.554  1.00  0.00           H  
HETATM   39  H9  UNL     1       5.895  -1.023  -1.163  1.00  0.00           H  
HETATM   40  H10 UNL     1       4.383  -2.944   0.694  1.00  0.00           H  
HETATM   41  H11 UNL     1       5.117  -1.478   1.315  1.00  0.00           H  
HETATM   42  H12 UNL     1       2.958  -1.754  -0.920  1.00  0.00           H  
HETATM   43  H13 UNL     1       2.065   0.221  -0.182  1.00  0.00           H  
HETATM   44  H14 UNL     1       2.803   0.864   2.161  1.00  0.00           H  
HETATM   45  H15 UNL     1       4.347   0.076   1.952  1.00  0.00           H  
HETATM   46  H16 UNL     1       4.634   2.485   2.074  1.00  0.00           H  
HETATM   47  H17 UNL     1       4.707   3.783   0.230  1.00  0.00           H  
HETATM   48  H18 UNL     1       4.636   2.637  -1.921  1.00  0.00           H  
HETATM   49  H19 UNL     1       3.396   1.500  -1.453  1.00  0.00           H  
HETATM   50  H20 UNL     1       2.484   3.274  -2.765  1.00  0.00           H  
HETATM   51  H21 UNL     1       3.416   4.498  -1.891  1.00  0.00           H  
HETATM   52  H22 UNL     1       1.846   4.457   0.024  1.00  0.00           H  
HETATM   53  H23 UNL     1       1.045   4.752  -1.515  1.00  0.00           H  
HETATM   54  H24 UNL     1       0.823   2.047  -0.069  1.00  0.00           H  
HETATM   55  H25 UNL     1      -0.300   3.388  -0.206  1.00  0.00           H  
HETATM   56  H26 UNL     1      -0.381   3.207  -2.614  1.00  0.00           H  
HETATM   57  H27 UNL     1       0.927   1.968  -2.658  1.00  0.00           H  
HETATM   58  H28 UNL     1      -1.273   1.012  -2.962  1.00  0.00           H  
HETATM   59  H29 UNL     1      -0.490   0.370  -1.472  1.00  0.00           H  
HETATM   60  H30 UNL     1      -2.647   2.528  -1.828  1.00  0.00           H  
HETATM   61  H31 UNL     1      -1.941   2.188  -0.216  1.00  0.00           H  
HETATM   62  H32 UNL     1      -4.808  -1.130  -0.868  1.00  0.00           H  
HETATM   63  H33 UNL     1      -6.803   1.192  -0.619  1.00  0.00           H  
HETATM   64  H34 UNL     1      -6.122   0.481  -2.110  1.00  0.00           H  
HETATM   65  H35 UNL     1      -5.866   0.322   1.631  1.00  0.00           H  
HETATM   66  H36 UNL     1      -4.433  -0.718   1.541  1.00  0.00           H  
HETATM   67  H37 UNL     1      -7.545  -1.461   3.216  1.00  0.00           H  
HETATM   68  H38 UNL     1      -8.373  -1.913   1.693  1.00  0.00           H  
HETATM   69  H39 UNL     1      -7.713  -0.205   1.957  1.00  0.00           H  
HETATM   70  H40 UNL     1      -4.434  -2.161   2.566  1.00  0.00           H  
HETATM   71  H41 UNL     1      -5.833  -3.346   2.850  1.00  0.00           H  
HETATM   72  H42 UNL     1      -5.794  -1.750   3.647  1.00  0.00           H  
HETATM   73  H43 UNL     1      -5.945  -2.669  -0.285  1.00  0.00           H  
HETATM   74  H44 UNL     1      -6.225  -3.781   1.144  1.00  0.00           H  
HETATM   75  H45 UNL     1      -7.562  -2.884   0.440  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   26   27   65   66
CONECT   27   28   29   30
CONECT   28   67   68   69
CONECT   29   70   71   72
CONECT   30   73   74   75
END

HMDB0240780
     RDKit          3D
O-Linoleoylcarnitine
 75 74  0  0  0  0  0  0  0  0999 V2000
    7.5494   -2.0290    1.8948 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9790   -2.1100    0.4601 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0077   -2.6803   -0.4906 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7137   -2.0486   -0.7112 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7479   -1.8952    0.4002 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5211   -1.2351   -0.1075 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0219   -0.0749    0.3137 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6374    0.7041    1.3515 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1706    2.0302    1.1438 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2173    2.7850    0.1070 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7067    2.5081   -1.2368 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7783    3.5833   -1.7185 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5868    3.9279   -0.9382 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5745    2.8674   -0.7190 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0824    2.3594   -2.0663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9536    1.2690   -1.9320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1642    1.7330   -1.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1843    0.6619   -1.0529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9064   -0.4532   -1.5703 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3782    0.8160   -0.4143 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3253   -0.3275   -0.3388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5046    0.2094   -1.0848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6678   -0.6165   -1.2647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7299   -0.4507   -0.6316 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6416   -1.6682   -2.1893 O   0  0  0  0  0  1  0  0  0  0  0  0
   -5.4842   -0.6113    1.1082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2585   -1.6963    1.5573 N   0  0  0  0  0  4  0  0  0  0  0  0
   -7.5363   -1.2948    2.1289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5157   -2.2912    2.7234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4679   -2.7934    0.6660 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2251   -1.0196    2.2214 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8386   -2.8280    2.1780 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4418   -2.2345    2.5790 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4405   -1.1481    0.1097 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8716   -2.8123    0.4536 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8645   -3.7667   -0.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5700   -2.8161   -1.4707 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1784   -2.5830   -1.5542 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8948   -1.0232   -1.1628 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3827   -2.9441    0.6935 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1171   -1.4785    1.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9579   -1.7541   -0.9197 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0654    0.2214   -0.1815 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8027    0.8636    2.1614 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3470    0.0759    1.9522 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6339    2.4846    2.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7065    3.7835    0.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6356    2.6366   -1.9206 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3956    1.5000   -1.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4841    3.2744   -2.7655 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4164    4.4978   -1.8913 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8457    4.4573    0.0240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0450    4.7525   -1.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8229    2.0468   -0.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3005    3.3878   -0.2060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3805    3.2073   -2.6138 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9271    1.9677   -2.6583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2727    1.0122   -2.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4901    0.3695   -1.4719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6466    2.5277   -1.8284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9410    2.1881   -0.2164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8083   -1.1303   -0.8680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8033    1.1919   -0.6189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1218    0.4809   -2.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8659    0.3220    1.6314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4329   -0.7175    1.5412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5447   -1.4615    3.2161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3733   -1.9127    1.6931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7127   -0.2052    1.9570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4338   -2.1615    2.5656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8333   -3.3459    2.8501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7938   -1.7501    3.6468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9452   -2.6692   -0.2852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2251   -3.7815    1.1442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5617   -2.8845    0.4401 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  0
 22 63  1  0
 22 64  1  0
 26 65  1  0
 26 66  1  0
 28 67  1  0
 28 68  1  0
 28 69  1  0
 29 70  1  0
 29 71  1  0
 29 72  1  0
 30 73  1  0
 30 74  1  0
 30 75  1  0
M  CHG  2  25  -1  27   1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(9Z,12Z)-Octadeca-9,12-dienoylcarnitine	ChEBI
3-[(9Z,12Z)-Octadeca-9,12-dienoyloxy]-4-(trimethylammonio)butanoate	ChEBI
9cis,12cis-Octadecadienoylcarnitine	ChEBI
Linoleylcarnitine	ChEBI
3-[(9Z,12Z)-Octadeca-9,12-dienoyloxy]-4-(trimethylammonio)butanoic acid	Generator

Chemical Formula

C₂₅H₄₅NO₄

Average Molecular Weight

423.638

Monoisotopic Molecular Weight

423.334858933

IUPAC Name

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

Traditional Name

linoelaidyl carnitine

CAS Registry Number

Not Available

SMILES

[H]\C(CCCCC)=C(/[H])C\C([H])=C(\[H])CCCCCCCC(=O)OC(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-

InChI Key

MJLXQSQYKZWZCB-UTJQPWESSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Acyl carnitines

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

carboxylic ester (CHEBI:73072 )
O-acylcarnitine (CHEBI:73072 )
ammonium betaine (CHEBI:73072 )

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

Cell

All cells and tissues (PMID: 35710135)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 35710135)

Excreta

Biofluid or Excreta

Urine (PMID: 35710135)

Cellular substructure

cytoplasm (PMID: 35710135)
mitochondrion matrix (PMID: 35710135)

Organelle

peroxisome (PMID: 35710135)

Source

Endogenous

Endogenous (HMDB: HMDB0240780)

Process

Not Available

Role

Biological role

Energy source (PMID: 35710135)

Industrial application

Pharmaceutical industry

Biomarker

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
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	51.26 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]+	216.085	30932474
DeepCCS	[M-H]-	213.69	30932474
DeepCCS	[M-2H]-	246.574	30932474
DeepCCS	[M+Na]+	221.998	30932474
AllCCS	[M+H]+	219.0	32859911
AllCCS	[M+H-H2O]+	217.2	32859911
AllCCS	[M+NH4]+	220.7	32859911
AllCCS	[M+Na]+	221.2	32859911
AllCCS	[M-H]-	211.2	32859911
AllCCS	[M+Na-2H]-	213.6	32859911
AllCCS	[M+HCOO]-	216.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
O-Linoleoylcarnitine	[H]\C(CCCCC)=C(/[H])C\C([H])=C(\[H])CCCCCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C	3464.9	Standard polar	33892256
O-Linoleoylcarnitine	[H]\C(CCCCC)=C(/[H])C\C([H])=C(\[H])CCCCCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C	2560.4	Standard non polar	33892256
O-Linoleoylcarnitine	[H]\C(CCCCC)=C(/[H])C\C([H])=C(\[H])CCCCCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C	2895.7	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 - O-Linoleoylcarnitine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - O-Linoleoylcarnitine 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 - O-Linoleoylcarnitine 10V, Positive-QTOF	splash10-00di-0000900000-013b520638a6f6e841ef	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Linoleoylcarnitine 20V, Positive-QTOF	splash10-0079-9000500000-f8699786d83873f3e7b3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Linoleoylcarnitine 40V, Positive-QTOF	splash10-000i-9000000000-e9262cbaff8cb4ad0ba6	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28639188

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

51000598

PDB ID

Not Available

ChEBI ID

73072

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

Iacobazzi V, Pasquali M, Singh R, Matern D, Rinaldo P, Amat di San Filippo C, Palmieri F, Longo N: Response to therapy in carnitine/acylcarnitine translocase (CACT) deficiency due to a novel missense mutation. Am J Med Genet A. 2004 Apr 15;126A(2):150-5. [PubMed:15057979 ]
Sud M, Fahy E, Cotter D, Brown A, Dennis EA, Glass CK, Merrill AH Jr, Murphy RC, Raetz CR, Russell DW, Subramaniam S: LMSD: LIPID MAPS structure database. Nucleic Acids Res. 2007 Jan;35(Database issue):D527-32. doi: 10.1093/nar/gkl838. Epub 2006 Nov 10. [PubMed:17098933 ]
FRITZ IB: Action of carnitine on long chain fatty acid oxidation by liver. Am J Physiol. 1959 Aug;197:297-304. doi: 10.1152/ajplegacy.1959.197.2.297. [PubMed:13825279 ]
Reuter SE, Evans AM: Carnitine and acylcarnitines: pharmacokinetic, pharmacological and clinical aspects. Clin Pharmacokinet. 2012 Sep 1;51(9):553-72. doi: 10.1007/BF03261931. [PubMed:22804748 ]
Bruce CR, Hoy AJ, Turner N, Watt MJ, Allen TL, Carpenter K, Cooney GJ, Febbraio MA, Kraegen EW: Overexpression of carnitine palmitoyltransferase-1 in skeletal muscle is sufficient to enhance fatty acid oxidation and improve high-fat diet-induced insulin resistance. Diabetes. 2009 Mar;58(3):550-8. doi: 10.2337/db08-1078. Epub 2008 Dec 10. [PubMed:19073774 ]
Schooneman MG, Vaz FM, Houten SM, Soeters MR: Acylcarnitines: reflecting or inflicting insulin resistance? Diabetes. 2013 Jan;62(1):1-8. doi: 10.2337/db12-0466. [PubMed:23258903 ]
Ahmad T, Kelly JP, McGarrah RW, Hellkamp AS, Fiuzat M, Testani JM, Wang TS, Verma A, Samsky MD, Donahue MP, Ilkayeva OR, Bowles DE, Patel CB, Milano CA, Rogers JG, Felker GM, O'Connor CM, Shah SH, Kraus WE: Prognostic Implications of Long-Chain Acylcarnitines in Heart Failure and Reversibility With Mechanical Circulatory Support. J Am Coll Cardiol. 2016 Jan 26;67(3):291-9. doi: 10.1016/j.jacc.2015.10.079. [PubMed:26796394 ]
Hunter WG, Kelly JP, McGarrah RW 3rd, Khouri MG, Craig D, Haynes C, Ilkayeva O, Stevens RD, Bain JR, Muehlbauer MJ, Newgard CB, Felker GM, Hernandez AF, Velazquez EJ, Kraus WE, Shah SH: Metabolomic Profiling Identifies Novel Circulating Biomarkers of Mitochondrial Dysfunction Differentially Elevated in Heart Failure With Preserved Versus Reduced Ejection Fraction: Evidence for Shared Metabolic Impairments in Clinical Heart Failure. J Am Heart Assoc. 2016 Jul 29;5(8). pii: JAHA.115.003190. doi: 10.1161/JAHA.115.003190. [PubMed:27473038 ]
Liepinsh E, Makrecka-Kuka M, Volska K, Kuka J, Makarova E, Antone U, Sevostjanovs E, Vilskersts R, Strods A, Tars K, Dambrova M: Long-chain acylcarnitines determine ischaemia/reperfusion-induced damage in heart mitochondria. Biochem J. 2016 May 1;473(9):1191-202. doi: 10.1042/BCJ20160164. Epub 2016 Mar 2. [PubMed:26936967 ]
Shah SH, Sun JL, Stevens RD, Bain JR, Muehlbauer MJ, Pieper KS, Haynes C, Hauser ER, Kraus WE, Granger CB, Newgard CB, Califf RM, Newby LK: Baseline metabolomic profiles predict cardiovascular events in patients at risk for coronary artery disease. Am Heart J. 2012 May;163(5):844-850.e1. doi: 10.1016/j.ahj.2012.02.005. [PubMed:22607863 ]
Rizza S, Copetti M, Rossi C, Cianfarani MA, Zucchelli M, Luzi A, Pecchioli C, Porzio O, Di Cola G, Urbani A, Pellegrini F, Federici M: Metabolomics signature improves the prediction of cardiovascular events in elderly subjects. Atherosclerosis. 2014 Feb;232(2):260-4. doi: 10.1016/j.atherosclerosis.2013.10.029. Epub 2013 Nov 18. [PubMed:24468136 ]
Chang KH, Cheng ML, Tang HY, Huang CY, Wu YR, Chen CM: Alternations of Metabolic Profile and Kynurenine Metabolism in the Plasma of Parkinson's Disease. Mol Neurobiol. 2018 Aug;55(8):6319-6328. doi: 10.1007/s12035-017-0845-3. Epub 2018 Jan 2. [PubMed:29294246 ]
Dambrova M, Makrecka-Kuka M, Kuka J, Vilskersts R, Nordberg D, Attwood MM, Smesny S, Sen ZD, Guo AC, Oler E, Tian S, Zheng J, Wishart DS, Liepinsh E, Schioth HB: Acylcarnitines: Nomenclature, Biomarkers, Therapeutic Potential, Drug Targets, and Clinical Trials. Pharmacol Rev. 2022 Jul;74(3):506-551. doi: 10.1124/pharmrev.121.000408. [PubMed:35710135 ]

Showing metabocard for O-Linoleoylcarnitine (HMDB0240780)

MOL for HMDB0240780 (O-Linoleoylcarnitine)

3D MOL for HMDB0240780 (O-Linoleoylcarnitine)

3D SDF for HMDB0240780 (O-Linoleoylcarnitine)

3D-SDF for HMDB0240780 (O-Linoleoylcarnitine)

PDB for HMDB0240780 (O-Linoleoylcarnitine)

3D PDB for HMDB0240780 (O-Linoleoylcarnitine)

SMILES for HMDB0240780 (O-Linoleoylcarnitine)

INCHI for HMDB0240780 (O-Linoleoylcarnitine)

Structure for HMDB0240780 (O-Linoleoylcarnitine)

3D Structure for HMDB0240780 (O-Linoleoylcarnitine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra