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Record Information

Version

5.0

Status

Predicted

Creation Date

2021-03-31 19:17:45 UTC

Update Date

2022-10-24 19:45:13 UTC

HMDB ID

HMDB0241586

Secondary Accession Numbers

None

Metabolite Identification

Common Name

3-Icosa-5,8,11-trienoylcarnitine

Description

3-Icosa-5,8,11-trienoylcarnitine is an acylcarnitine. More specifically, it is an 3-hydroxyicosa-5,8,11-trienoic 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. 3-Icosa-5,8,11-trienoylcarnitine is therefore classified as a long chain AC. As a long-chain acylcarnitine 3-Icosa-5,8,11-trienoylcarnitine 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


  Mrv1652303312121172D          

 33 32  0  0  0  0            999 V2000
   -4.1467    0.0809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1467    0.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4322    1.3184    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -4.8612    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8612    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1467    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1467    3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8612    3.7934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4322    3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7177    3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0033    3.7934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7177    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0033    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2888    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5756    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2901    2.1434    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -6.7026    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8776    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0046    1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  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  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 13 12  1  4  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  4  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  4  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
  5 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
M  CHG  2   3  -1  30   1
M  END

HMDB0241586
     RDKit          3D
3-Icosa-5,8,11-trienoylcarnitine
 80 79  0  0  0  0  0  0  0  0999 V2000
    9.5704    0.4218    0.4104 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9260   -1.0135    0.4383 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0107   -1.9896   -0.1755 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7258   -2.2838    0.3854 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5960   -1.4209    0.6873 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6017   -0.4289    1.7636 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3205    0.3573    1.8197 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0455    1.3413    0.7654 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0032    1.0296   -0.6428 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9977    1.0878   -1.4844 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6366    1.5178   -1.0810 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6935    0.4188   -1.3618 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6781    0.4969   -2.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2644    1.6531   -2.9279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0331    2.2681   -2.6764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9677    2.0427   -1.8359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0806    1.0491   -0.7727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2796    1.7132    0.5938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3754    0.6712    1.5137 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4622    2.6210    0.6508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7109    1.8920    0.3849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7794    2.5806    0.4153 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8575    0.5650    0.1117 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1326   -0.0536   -0.1231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1970   -0.5725   -1.5352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0197    0.5805   -2.4556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8727    0.9668   -2.7289 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1446    1.1855   -2.9772 O   0  0  0  0  0  1  0  0  0  0  0  0
   -6.3968   -1.0765    0.9252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6375   -1.7775    0.8538 N   0  0  0  0  0  4  0  0  0  0  0  0
   -8.7717   -0.9154    0.5731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6592   -2.8953   -0.0472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8636   -2.3127    2.2216 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6036    0.9377    1.3995 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6073    0.6476   -0.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3309    0.9941   -0.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9785   -1.0890   -0.0045 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1001   -1.2746    1.5321 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6636   -2.9645   -0.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9546   -1.7831   -1.3149 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2674   -3.1055   -0.3305 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8591   -3.0220    1.3101 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7741   -2.2065    1.0775 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0230   -1.1280   -0.2526 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5824   -1.0391    2.7438 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3978    0.3056    1.8382 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4367   -0.3601    1.8352 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2417    0.8973    2.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1533    1.9606    1.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9268    2.1147    0.8667 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9756    0.7532   -1.1487 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1651    0.8055   -2.5376 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5682    1.7418    0.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4376    2.4549   -1.5968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9148   -0.5258   -0.8251 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0940   -0.4557   -2.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3101    1.3490   -4.0432 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0666    2.4534   -2.9138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2429    3.1528   -3.4093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8734    2.7228   -1.9211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8872    0.3087   -0.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1573    0.4487   -0.7041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3288    2.2888    0.7668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5928   -0.2029    1.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5191    3.1261    1.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3059    3.4565   -0.0856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8724    0.7706   -0.0147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3430   -1.3050   -1.6517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1029   -1.1470   -1.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5661   -1.8250    0.8883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3177   -0.6284    1.9605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6433   -1.3096    1.1802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0804   -1.1053   -0.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5991    0.1364    0.8198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6920   -3.1284   -0.5212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4986   -2.8002   -0.7982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9429   -3.8123    0.5444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1465   -3.1215    2.4354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8834   -2.7292    2.3007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6653   -1.4786    2.9212 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  3
 10 11  1  0
 11 12  1  0
 12 13  2  3
 13 14  1  0
 14 15  1  0
 15 16  2  3
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 24 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
 30 33  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  0
  2 38  1  0
  3 39  1  0
  3 40  1  0
  4 41  1  0
  4 42  1  0
  5 43  1  0
  5 44  1  0
  6 45  1  0
  6 46  1  0
  7 47  1  0
  7 48  1  0
  8 49  1  0
  8 50  1  0
  9 51  1  0
 10 52  1  0
 11 53  1  0
 11 54  1  0
 12 55  1  0
 13 56  1  0
 14 57  1  0
 14 58  1  0
 15 59  1  0
 16 60  1  0
 17 61  1  0
 17 62  1  0
 18 63  1  0
 19 64  1  0
 20 65  1  0
 20 66  1  0
 24 67  1  0
 25 68  1  0
 25 69  1  0
 29 70  1  0
 29 71  1  0
 31 72  1  0
 31 73  1  0
 31 74  1  0
 32 75  1  0
 32 76  1  0
 32 77  1  0
 33 78  1  0
 33 79  1  0
 33 80  1  0
M  CHG  2  28  -1  30   1
M  END


  Mrv1652303312121172D          

 33 32  0  0  0  0            999 V2000
   -4.1467    0.0809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1467    0.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4322    1.3184    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -4.8612    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8612    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1467    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1467    3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8612    3.7934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4322    3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7177    3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0033    3.7934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7177    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0033    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2888    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5756    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2901    2.1434    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -6.7026    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8776    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0046    1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  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  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 13 12  1  4  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  4  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  4  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
  5 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
M  CHG  2   3  -1  30   1
M  END
> <DATABASE_ID>
HMDB0241586

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCCC=CCC=CCC=CCC(O)CC(=O)OC(CC([O-])=O)C[N+](C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C27H47NO5/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-24(29)21-27(32)33-25(22-26(30)31)23-28(2,3)4/h12-13,15-16,18-19,24-25,29H,5-11,14,17,20-23H2,1-4H3

> <INCHI_KEY>
XYEDXCSCWRSRQM-UHFFFAOYSA-N

> <FORMULA>
C27H47NO5

> <MOLECULAR_WEIGHT>
465.675

> <EXACT_MASS>
465.345423617

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
55.262162527196125

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(3-hydroxyicosa-5,8,11-trienoyl)oxy]-4-(trimethylazaniumyl)butanoate

> <JCHEM_LOGP>
1.4952464771949203

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.944500523378007

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.11961580225018

> <JCHEM_PKA_STRONGEST_BASIC>
-2.823075755372682

> <JCHEM_POLAR_SURFACE_AREA>
86.66000000000001

> <JCHEM_REFRACTIVITY>
160.34599999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
21

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3-[(3-hydroxyicosa-5,8,11-trienoyl)oxy]-4-(trimethylammonio)butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0241586
     RDKit          3D
3-Icosa-5,8,11-trienoylcarnitine
 80 79  0  0  0  0  0  0  0  0999 V2000
    9.5704    0.4218    0.4104 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9260   -1.0135    0.4383 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0107   -1.9896   -0.1755 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7258   -2.2838    0.3854 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5960   -1.4209    0.6873 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6017   -0.4289    1.7636 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3205    0.3573    1.8197 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0455    1.3413    0.7654 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0032    1.0296   -0.6428 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9977    1.0878   -1.4844 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6366    1.5178   -1.0810 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6935    0.4188   -1.3618 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6781    0.4969   -2.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2644    1.6531   -2.9279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0331    2.2681   -2.6764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9677    2.0427   -1.8359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0806    1.0491   -0.7727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2796    1.7132    0.5938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3754    0.6712    1.5137 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4622    2.6210    0.6508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7109    1.8920    0.3849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7794    2.5806    0.4153 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8575    0.5650    0.1117 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1326   -0.0536   -0.1231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1970   -0.5725   -1.5352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0197    0.5805   -2.4556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8727    0.9668   -2.7289 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1446    1.1855   -2.9772 O   0  0  0  0  0  1  0  0  0  0  0  0
   -6.3968   -1.0765    0.9252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6375   -1.7775    0.8538 N   0  0  0  0  0  4  0  0  0  0  0  0
   -8.7717   -0.9154    0.5731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6592   -2.8953   -0.0472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8636   -2.3127    2.2216 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6036    0.9377    1.3995 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6073    0.6476   -0.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3309    0.9941   -0.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9785   -1.0890   -0.0045 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1001   -1.2746    1.5321 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6636   -2.9645   -0.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9546   -1.7831   -1.3149 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2674   -3.1055   -0.3305 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8591   -3.0220    1.3101 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7741   -2.2065    1.0775 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0230   -1.1280   -0.2526 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5824   -1.0391    2.7438 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3978    0.3056    1.8382 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4367   -0.3601    1.8352 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2417    0.8973    2.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1533    1.9606    1.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9268    2.1147    0.8667 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9756    0.7532   -1.1487 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1651    0.8055   -2.5376 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5682    1.7418    0.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4376    2.4549   -1.5968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9148   -0.5258   -0.8251 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0940   -0.4557   -2.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3101    1.3490   -4.0432 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0666    2.4534   -2.9138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2429    3.1528   -3.4093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8734    2.7228   -1.9211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8872    0.3087   -0.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1573    0.4487   -0.7041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3288    2.2888    0.7668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5928   -0.2029    1.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5191    3.1261    1.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3059    3.4565   -0.0856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8724    0.7706   -0.0147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3430   -1.3050   -1.6517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1029   -1.1470   -1.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5661   -1.8250    0.8883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3177   -0.6284    1.9605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6433   -1.3096    1.1802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0804   -1.1053   -0.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5991    0.1364    0.8198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6920   -3.1284   -0.5212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4986   -2.8002   -0.7982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9429   -3.8123    0.5444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1465   -3.1215    2.4354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8834   -2.7292    2.3007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6653   -1.4786    2.9212 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  3
 10 11  1  0
 11 12  1  0
 12 13  2  3
 13 14  1  0
 14 15  1  0
 15 16  2  3
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 24 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
 30 33  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  0
  2 38  1  0
  3 39  1  0
  3 40  1  0
  4 41  1  0
  4 42  1  0
  5 43  1  0
  5 44  1  0
  6 45  1  0
  6 46  1  0
  7 47  1  0
  7 48  1  0
  8 49  1  0
  8 50  1  0
  9 51  1  0
 10 52  1  0
 11 53  1  0
 11 54  1  0
 12 55  1  0
 13 56  1  0
 14 57  1  0
 14 58  1  0
 15 59  1  0
 16 60  1  0
 17 61  1  0
 17 62  1  0
 18 63  1  0
 19 64  1  0
 20 65  1  0
 20 66  1  0
 24 67  1  0
 25 68  1  0
 25 69  1  0
 29 70  1  0
 29 71  1  0
 31 72  1  0
 31 73  1  0
 31 74  1  0
 32 75  1  0
 32 76  1  0
 32 77  1  0
 33 78  1  0
 33 79  1  0
 33 80  1  0
M  CHG  2  28  -1  30   1
M  END

HEADER    PROTEIN                                 31-MAR-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-MAR-21         0                                  
HETATM    1  O   UNK     0      -7.740   0.151   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -7.740   1.691   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -6.407   2.461   0.000  0.00  0.00           O-1
HETATM    4  C   UNK     0      -9.074   2.461   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -9.074   4.001   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -7.740   4.771   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -7.740   6.311   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -9.074   7.081   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -6.407   7.081   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.073   6.311   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -3.739   7.081   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -5.073   4.771   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.739   4.001   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.406   4.771   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.072   4.001   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.262   4.771   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.595   4.001   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.929   4.771   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.263   4.001   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.596   4.771   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.597   4.001   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.598   4.771   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      16.266   4.771   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -10.408   4.771   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0     -11.742   4.001   0.000  0.00  0.00           N+1
HETATM   31  C   UNK     0     -12.512   5.335   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -10.972   2.667   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -13.075   3.231   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   29                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
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   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29    5   30                                                       
CONECT   30   29   31   32   33                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   30                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   64    0
END

COMPND    HMDB0241586
HETATM    1  C1  UNL     1       9.570   0.422   0.410  1.00  0.00           C  
HETATM    2  C2  UNL     1       9.926  -1.013   0.438  1.00  0.00           C  
HETATM    3  C3  UNL     1       9.011  -1.990  -0.175  1.00  0.00           C  
HETATM    4  C4  UNL     1       7.726  -2.284   0.385  1.00  0.00           C  
HETATM    5  C5  UNL     1       6.596  -1.421   0.687  1.00  0.00           C  
HETATM    6  C6  UNL     1       6.602  -0.429   1.764  1.00  0.00           C  
HETATM    7  C7  UNL     1       5.320   0.357   1.820  1.00  0.00           C  
HETATM    8  C8  UNL     1       5.045   1.341   0.765  1.00  0.00           C  
HETATM    9  C9  UNL     1       5.003   1.030  -0.643  1.00  0.00           C  
HETATM   10  C10 UNL     1       3.998   1.088  -1.484  1.00  0.00           C  
HETATM   11  C11 UNL     1       2.637   1.518  -1.081  1.00  0.00           C  
HETATM   12  C12 UNL     1       1.693   0.419  -1.362  1.00  0.00           C  
HETATM   13  C13 UNL     1       0.678   0.497  -2.160  1.00  0.00           C  
HETATM   14  C14 UNL     1       0.264   1.653  -2.928  1.00  0.00           C  
HETATM   15  C15 UNL     1      -1.033   2.268  -2.676  1.00  0.00           C  
HETATM   16  C16 UNL     1      -1.968   2.043  -1.836  1.00  0.00           C  
HETATM   17  C17 UNL     1      -2.081   1.049  -0.773  1.00  0.00           C  
HETATM   18  C18 UNL     1      -2.280   1.713   0.594  1.00  0.00           C  
HETATM   19  O1  UNL     1      -2.375   0.671   1.514  1.00  0.00           O  
HETATM   20  C19 UNL     1      -3.462   2.621   0.651  1.00  0.00           C  
HETATM   21  C20 UNL     1      -4.711   1.892   0.385  1.00  0.00           C  
HETATM   22  O2  UNL     1      -5.779   2.581   0.415  1.00  0.00           O  
HETATM   23  O3  UNL     1      -4.858   0.565   0.112  1.00  0.00           O  
HETATM   24  C21 UNL     1      -6.133  -0.054  -0.123  1.00  0.00           C  
HETATM   25  C22 UNL     1      -6.197  -0.572  -1.535  1.00  0.00           C  
HETATM   26  C23 UNL     1      -6.020   0.581  -2.456  1.00  0.00           C  
HETATM   27  O4  UNL     1      -4.873   0.967  -2.729  1.00  0.00           O  
HETATM   28  O5  UNL     1      -7.145   1.186  -2.977  1.00  0.00           O1-
HETATM   29  C24 UNL     1      -6.397  -1.077   0.925  1.00  0.00           C  
HETATM   30  N1  UNL     1      -7.638  -1.777   0.854  1.00  0.00           N1+
HETATM   31  C25 UNL     1      -8.772  -0.915   0.573  1.00  0.00           C  
HETATM   32  C26 UNL     1      -7.659  -2.895  -0.047  1.00  0.00           C  
HETATM   33  C27 UNL     1      -7.864  -2.313   2.222  1.00  0.00           C  
HETATM   34  H1  UNL     1       9.604   0.938   1.399  1.00  0.00           H  
HETATM   35  H2  UNL     1       8.607   0.648  -0.124  1.00  0.00           H  
HETATM   36  H3  UNL     1      10.331   0.994  -0.207  1.00  0.00           H  
HETATM   37  H4  UNL     1      10.978  -1.089  -0.004  1.00  0.00           H  
HETATM   38  H5  UNL     1      10.100  -1.275   1.532  1.00  0.00           H  
HETATM   39  H6  UNL     1       9.664  -2.964  -0.244  1.00  0.00           H  
HETATM   40  H7  UNL     1       8.955  -1.783  -1.315  1.00  0.00           H  
HETATM   41  H8  UNL     1       7.267  -3.105  -0.331  1.00  0.00           H  
HETATM   42  H9  UNL     1       7.859  -3.022   1.310  1.00  0.00           H  
HETATM   43  H10 UNL     1       5.774  -2.206   1.077  1.00  0.00           H  
HETATM   44  H11 UNL     1       6.023  -1.128  -0.253  1.00  0.00           H  
HETATM   45  H12 UNL     1       6.582  -1.039   2.744  1.00  0.00           H  
HETATM   46  H13 UNL     1       7.398   0.306   1.838  1.00  0.00           H  
HETATM   47  H14 UNL     1       4.437  -0.360   1.835  1.00  0.00           H  
HETATM   48  H15 UNL     1       5.242   0.897   2.814  1.00  0.00           H  
HETATM   49  H16 UNL     1       4.153   1.961   1.088  1.00  0.00           H  
HETATM   50  H17 UNL     1       5.927   2.115   0.867  1.00  0.00           H  
HETATM   51  H18 UNL     1       5.976   0.753  -1.149  1.00  0.00           H  
HETATM   52  H19 UNL     1       4.165   0.806  -2.538  1.00  0.00           H  
HETATM   53  H20 UNL     1       2.568   1.742   0.019  1.00  0.00           H  
HETATM   54  H21 UNL     1       2.438   2.455  -1.597  1.00  0.00           H  
HETATM   55  H22 UNL     1       1.915  -0.526  -0.825  1.00  0.00           H  
HETATM   56  H23 UNL     1       0.094  -0.456  -2.286  1.00  0.00           H  
HETATM   57  H24 UNL     1       0.310   1.349  -4.043  1.00  0.00           H  
HETATM   58  H25 UNL     1       1.067   2.453  -2.914  1.00  0.00           H  
HETATM   59  H26 UNL     1      -1.243   3.153  -3.409  1.00  0.00           H  
HETATM   60  H27 UNL     1      -2.873   2.723  -1.921  1.00  0.00           H  
HETATM   61  H28 UNL     1      -2.887   0.309  -0.964  1.00  0.00           H  
HETATM   62  H29 UNL     1      -1.157   0.449  -0.704  1.00  0.00           H  
HETATM   63  H30 UNL     1      -1.329   2.289   0.767  1.00  0.00           H  
HETATM   64  H31 UNL     1      -2.593  -0.203   1.087  1.00  0.00           H  
HETATM   65  H32 UNL     1      -3.519   3.126   1.668  1.00  0.00           H  
HETATM   66  H33 UNL     1      -3.306   3.456  -0.086  1.00  0.00           H  
HETATM   67  H34 UNL     1      -6.872   0.771  -0.015  1.00  0.00           H  
HETATM   68  H35 UNL     1      -5.343  -1.305  -1.652  1.00  0.00           H  
HETATM   69  H36 UNL     1      -7.103  -1.147  -1.767  1.00  0.00           H  
HETATM   70  H37 UNL     1      -5.566  -1.825   0.888  1.00  0.00           H  
HETATM   71  H38 UNL     1      -6.318  -0.628   1.961  1.00  0.00           H  
HETATM   72  H39 UNL     1      -9.643  -1.310   1.180  1.00  0.00           H  
HETATM   73  H40 UNL     1      -9.080  -1.105  -0.475  1.00  0.00           H  
HETATM   74  H41 UNL     1      -8.599   0.136   0.820  1.00  0.00           H  
HETATM   75  H42 UNL     1      -6.692  -3.128  -0.521  1.00  0.00           H  
HETATM   76  H43 UNL     1      -8.499  -2.800  -0.798  1.00  0.00           H  
HETATM   77  H44 UNL     1      -7.943  -3.812   0.544  1.00  0.00           H  
HETATM   78  H45 UNL     1      -7.146  -3.122   2.435  1.00  0.00           H  
HETATM   79  H46 UNL     1      -8.883  -2.729   2.301  1.00  0.00           H  
HETATM   80  H47 UNL     1      -7.665  -1.479   2.921  1.00  0.00           H  
CONECT    1    2   34   35   36
CONECT    2    3   37   38
CONECT    3    4   39   40
CONECT    4    5   41   42
CONECT    5    6   43   44
CONECT    6    7   45   46
CONECT    7    8   47   48
CONECT    8    9   49   50
CONECT    9   10   10   51
CONECT   10   11   52
CONECT   11   12   53   54
CONECT   12   13   13   55
CONECT   13   14   56
CONECT   14   15   57   58
CONECT   15   16   16   59
CONECT   16   17   60
CONECT   17   18   61   62
CONECT   18   19   20   63
CONECT   19   64
CONECT   20   21   65   66
CONECT   21   22   22   23
CONECT   23   24
CONECT   24   25   29   67
CONECT   25   26   68   69
CONECT   26   27   27   28
CONECT   29   30   70   71
CONECT   30   31   32   33
CONECT   31   72   73   74
CONECT   32   75   76   77
CONECT   33   78   79   80
END

HMDB0241586
     RDKit          3D
3-Icosa-5,8,11-trienoylcarnitine
 80 79  0  0  0  0  0  0  0  0999 V2000
    9.5704    0.4218    0.4104 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9260   -1.0135    0.4383 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0107   -1.9896   -0.1755 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7258   -2.2838    0.3854 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5960   -1.4209    0.6873 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6017   -0.4289    1.7636 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3205    0.3573    1.8197 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0455    1.3413    0.7654 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0032    1.0296   -0.6428 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9977    1.0878   -1.4844 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6366    1.5178   -1.0810 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6935    0.4188   -1.3618 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6781    0.4969   -2.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2644    1.6531   -2.9279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0331    2.2681   -2.6764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9677    2.0427   -1.8359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0806    1.0491   -0.7727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2796    1.7132    0.5938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3754    0.6712    1.5137 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4622    2.6210    0.6508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7109    1.8920    0.3849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7794    2.5806    0.4153 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8575    0.5650    0.1117 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1326   -0.0536   -0.1231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1970   -0.5725   -1.5352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0197    0.5805   -2.4556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8727    0.9668   -2.7289 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1446    1.1855   -2.9772 O   0  0  0  0  0  1  0  0  0  0  0  0
   -6.3968   -1.0765    0.9252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6375   -1.7775    0.8538 N   0  0  0  0  0  4  0  0  0  0  0  0
   -8.7717   -0.9154    0.5731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6592   -2.8953   -0.0472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8636   -2.3127    2.2216 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6036    0.9377    1.3995 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6073    0.6476   -0.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3309    0.9941   -0.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9785   -1.0890   -0.0045 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1001   -1.2746    1.5321 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6636   -2.9645   -0.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9546   -1.7831   -1.3149 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2674   -3.1055   -0.3305 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8591   -3.0220    1.3101 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7741   -2.2065    1.0775 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0230   -1.1280   -0.2526 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5824   -1.0391    2.7438 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3978    0.3056    1.8382 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4367   -0.3601    1.8352 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2417    0.8973    2.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1533    1.9606    1.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9268    2.1147    0.8667 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9756    0.7532   -1.1487 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1651    0.8055   -2.5376 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5682    1.7418    0.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4376    2.4549   -1.5968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9148   -0.5258   -0.8251 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0940   -0.4557   -2.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3101    1.3490   -4.0432 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0666    2.4534   -2.9138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2429    3.1528   -3.4093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8734    2.7228   -1.9211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8872    0.3087   -0.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1573    0.4487   -0.7041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3288    2.2888    0.7668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5928   -0.2029    1.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5191    3.1261    1.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3059    3.4565   -0.0856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8724    0.7706   -0.0147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3430   -1.3050   -1.6517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1029   -1.1470   -1.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5661   -1.8250    0.8883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3177   -0.6284    1.9605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6433   -1.3096    1.1802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0804   -1.1053   -0.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5991    0.1364    0.8198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6920   -3.1284   -0.5212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4986   -2.8002   -0.7982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9429   -3.8123    0.5444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1465   -3.1215    2.4354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8834   -2.7292    2.3007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6653   -1.4786    2.9212 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  3
 10 11  1  0
 11 12  1  0
 12 13  2  3
 13 14  1  0
 14 15  1  0
 15 16  2  3
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 24 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
 30 33  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  0
  2 38  1  0
  3 39  1  0
  3 40  1  0
  4 41  1  0
  4 42  1  0
  5 43  1  0
  5 44  1  0
  6 45  1  0
  6 46  1  0
  7 47  1  0
  7 48  1  0
  8 49  1  0
  8 50  1  0
  9 51  1  0
 10 52  1  0
 11 53  1  0
 11 54  1  0
 12 55  1  0
 13 56  1  0
 14 57  1  0
 14 58  1  0
 15 59  1  0
 16 60  1  0
 17 61  1  0
 17 62  1  0
 18 63  1  0
 19 64  1  0
 20 65  1  0
 20 66  1  0
 24 67  1  0
 25 68  1  0
 25 69  1  0
 29 70  1  0
 29 71  1  0
 31 72  1  0
 31 73  1  0
 31 74  1  0
 32 75  1  0
 32 76  1  0
 32 77  1  0
 33 78  1  0
 33 79  1  0
 33 80  1  0
M  CHG  2  28  -1  30   1
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₇H₄₇NO₅

Average Molecular Weight

465.675

Monoisotopic Molecular Weight

465.345423617

IUPAC Name

3-[(3-hydroxyicosa-5,8,11-trienoyl)oxy]-4-(trimethylazaniumyl)butanoate

Traditional Name

3-[(3-hydroxyicosa-5,8,11-trienoyl)oxy]-4-(trimethylammonio)butanoate

CAS Registry Number

Not Available

SMILES

CCCCCCCCC=CCC=CCC=CCC(O)CC(=O)OC(CC([O-])=O)C[N+](C)(C)C

InChI Identifier

InChI=1S/C27H47NO5/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-24(29)21-27(32)33-25(22-26(30)31)23-28(2,3)4/h12-13,15-16,18-19,24-25,29H,5-11,14,17,20-23H2,1-4H3

InChI Key

XYEDXCSCWRSRQM-UHFFFAOYSA-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
Beta-hydroxy acid
Hydroxy acid
Dicarboxylic acid or derivatives
Tetraalkylammonium salt
Quaternary ammonium salt
Secondary alcohol
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
Organic zwitterion
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Alcohol
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

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)

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	1.5	ChemAxon
pKa (Strongest Acidic)	4.12	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	86.66 Å²	ChemAxon
Rotatable Bond Count	21	ChemAxon
Refractivity	160.35 m³·mol⁻¹	ChemAxon
Polarizability	55.26 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]+	226.394	30932474
DeepCCS	[M-H]-	223.597	30932474
DeepCCS	[M-2H]-	257.383	30932474
DeepCCS	[M+Na]+	233.892	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Icosa-5,8,11-trienoylcarnitine	CCCCCCCCC=CCC=CCC=CCC(O)CC(=O)OC(CC([O-])=O)C[N+](C)(C)C	3847.8	Standard polar	33892256
3-Icosa-5,8,11-trienoylcarnitine	CCCCCCCCC=CCC=CCC=CCC(O)CC(=O)OC(CC([O-])=O)C[N+](C)(C)C	2816.6	Standard non polar	33892256
3-Icosa-5,8,11-trienoylcarnitine	CCCCCCCCC=CCC=CCC=CCC(O)CC(=O)OC(CC([O-])=O)C[N+](C)(C)C	3181.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Icosa-5,8,11-trienoylcarnitine,1TMS,isomer #1	CCCCCCCCC=CCC=CCC=CCC(CC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)O[Si](C)(C)C	3193.9	Semi standard non polar	33892256
3-Icosa-5,8,11-trienoylcarnitine,1TBDMS,isomer #1	CCCCCCCCC=CCC=CCC=CCC(CC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)O[Si](C)(C)C(C)(C)C	3422.1	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 - 3-Icosa-5,8,11-trienoylcarnitine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Icosa-5,8,11-trienoylcarnitine 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 - 3-Icosa-5,8,11-trienoylcarnitine 10V, Positive-QTOF	Not Available	2021-04-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Icosa-5,8,11-trienoylcarnitine 20V, Positive-QTOF	Not Available	2021-04-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Icosa-5,8,11-trienoylcarnitine 40V, Positive-QTOF	Not Available	2021-04-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Icosa-5,8,11-trienoylcarnitine 10V, Positive-QTOF	splash10-014i-0000900000-60995b9549c22bf85ecf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Icosa-5,8,11-trienoylcarnitine 20V, Positive-QTOF	splash10-00kr-9000500000-61947bd011c5551fe927	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Icosa-5,8,11-trienoylcarnitine 40V, Positive-QTOF	splash10-000i-9000000000-e9262cbaff8cb4ad0ba6	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Acylcarnitine 3-Icosa-5,8,11-trienoylcarnitine		Not Available

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

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

Blazenovic I, Kind T, Sa MR, Ji J, Vaniya A, Wancewicz B, Roberts BS, Torbasinovic H, Lee T, Mehta SS, Showalter MR, Song H, Kwok J, Jahn D, Kim J, Fiehn O: Structure Annotation of All Mass Spectra in Untargeted Metabolomics. Anal Chem. 2019 Feb 5;91(3):2155-2162. doi: 10.1021/acs.analchem.8b04698. Epub 2019 Jan 16. [PubMed:30608141 ]
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 ]
Yu D, Zhou L, Xuan Q, Wang L, Zhao X, Lu X, Xu G: Strategy for Comprehensive Identification of Acylcarnitines Based on Liquid Chromatography-High-Resolution Mass Spectrometry. Anal Chem. 2018 May 1;90(9):5712-5718. doi: 10.1021/acs.analchem.7b05471. Epub 2018 Apr 20. [PubMed:29651844 ]
Yan X, Markey SP, Marupaka R, Dong Q, Cooper BT, Mirokhin YA, Wallace WE, Stein SE: Mass Spectral Library of Acylcarnitines Derived from Human Urine. Anal Chem. 2020 May 5;92(9):6521-6528. doi: 10.1021/acs.analchem.0c00129. Epub 2020 Apr 23. [PubMed:32271007 ]
Zuniga A, Li L: Ultra-high performance liquid chromatography tandem mass spectrometry for comprehensive analysis of urinary acylcarnitines. Anal Chim Acta. 2011 Mar 9;689(1):77-84. doi: 10.1016/j.aca.2011.01.018. Epub 2011 Jan 18. [PubMed:21338760 ]
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 3-Icosa-5,8,11-trienoylcarnitine (HMDB0241586)

MOL for HMDB0241586 (3-Icosa-5,8,11-trienoylcarnitine)

3D MOL for HMDB0241586 (3-Icosa-5,8,11-trienoylcarnitine)

3D SDF for HMDB0241586 (3-Icosa-5,8,11-trienoylcarnitine)

3D-SDF for HMDB0241586 (3-Icosa-5,8,11-trienoylcarnitine)

PDB for HMDB0241586 (3-Icosa-5,8,11-trienoylcarnitine)

3D PDB for HMDB0241586 (3-Icosa-5,8,11-trienoylcarnitine)

SMILES for HMDB0241586 (3-Icosa-5,8,11-trienoylcarnitine)

INCHI for HMDB0241586 (3-Icosa-5,8,11-trienoylcarnitine)

Structure for HMDB0241586 (3-Icosa-5,8,11-trienoylcarnitine)

3D Structure for HMDB0241586 (3-Icosa-5,8,11-trienoylcarnitine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra