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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:32 UTC

Update Date

2022-10-24 19:44:10 UTC

HMDB ID

HMDB0002014

Secondary Accession Numbers

HMDB02014

Metabolite Identification

Common Name

cis-5-Tetradecenoylcarnitine

Description

cis-5-Tetradecenoylcarnitine is an acylcarnitine. More specifically, it is an cis-5-tetradecenoic 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. cis-5-Tetradecenoylcarnitine is therefore classified as a long chain AC. As a long-chain acylcarnitine cis-5-Tetradecenoylcarnitine 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 cis-5-Tetradecenoylcarnitine is elevated in the blood or plasma of individuals with very long-chain acyl-CoA dehydrogenase (VLACD) deficiency (PMID: 25843429 , PMID: 19327992 , PMID: 11433098 , PMID: 18670371 , PMID: 12828998 ), trifunctional protein (mitochondrial long-chain ketoacyl-coa thiolase) deficiency (PMID: 16423905 ), mitochondrial dysfunction in diabetes patients (PMID: 28726959 ), acadvl acyl-coa dehydrogenase very long chain deficiency (PMID: 29491033 ), nonalcoholic fatty liver disease (NAFLD) (PMID: 27211699 ), and insulin resistance type 2 diabetes (PMID: 24358186 ). 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 ). Defects in enzymes of the beta-oxidation pathway cause sudden, unexplained death in childhood, acute hepatic encephalopathy or liver failure, skeletal myopathy, and cardiomyopathy (PMID: 7479827 ). 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

HMDB02014.mol
  Mrv0541 02231219192D          

 26 25  0  0  0  0            999 V2000
   -5.0012    0.2063    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -4.2867    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5722    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8578    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8578    1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5722    1.8562    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -5.4137    0.9207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7156   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8569   -0.6232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5722   -0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8578   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5722    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2867    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0012    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7156    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8578   -1.8562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.8562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  7  1  0  0  0  0
  1  8  1  0  0  0  0
  1  9  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 15  2  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
 21 20  1  0  0  0  0
 22 21  1  0  0  0  0
 22 23  1  0  0  0  0
 11 24  2  0  0  0  0
  5 25  2  0  0  0  0
 13 26  1  0  0  0  0
 26 14  1  0  0  0  0
 16 15  1  0  0  0  0
M  CHG  2   1   1   6  -1
M  END

HMDB0002014
     RDKit          3D
cis-5-Tetradecenoylcarnitine
 65 64  0  0  0  0  0  0  0  0999 V2000
    9.0404   -1.1535   -2.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8628   -1.2800   -1.0769 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9265   -0.1547   -1.4060 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6789   -0.1914   -0.5229 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0508   -0.0685    0.8958 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0205   -0.0411    1.9394 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0522    1.0435    2.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1364    1.3644    0.9317 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1768    2.4379    1.3174 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9002    2.2558    1.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2386    1.0160    0.9088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5929    0.4839    2.0627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3153   -0.7869    1.7443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2642   -0.6056    0.5875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8987   -0.7377   -0.5861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5979   -0.2785    0.8226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5386   -0.0966   -0.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0176    1.3548   -0.2505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8189    2.2212   -0.4459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0269    2.4205    0.5099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5611    2.8144   -1.6713 O   0  0  0  0  0  1  0  0  0  0  0  0
   -5.6757   -0.9992    0.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7570   -1.0399   -0.8802 N   0  0  0  0  0  4  0  0  0  0  0  0
   -7.4355   -2.3305   -0.6424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7647   -0.0153   -0.7178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3920   -1.0605   -2.2772 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6019   -0.2223   -1.7917 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6938   -2.0244   -1.9642 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6283   -1.0570   -3.0597 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3935   -2.2629   -1.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2583   -1.1517   -0.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5940   -0.1728   -2.4645 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4785    0.7986   -1.2511 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9139    0.4450   -0.9374 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2632   -1.2561   -0.6854 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7295    0.8206    1.0436 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7376   -0.9445    1.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3948   -1.0068    1.8367 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5432   -0.2684    2.9322 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5260    2.0112    2.4649 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3911    0.7681    2.9714 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7344    0.4678    0.5190 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7729    1.9090    0.1422 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6367    3.3948    1.6208 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2834    3.1282    1.6058 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8160    0.2510    0.4111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5352    1.3205    0.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1147    0.2652    2.8885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2654    1.2814    2.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5998   -1.5553    1.4426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8704   -1.1124    2.6367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9733   -0.2813   -1.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7027    1.5695   -1.0782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5477    1.5990    0.6892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0728   -0.7513    1.0412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2679   -2.0448    0.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6289   -2.3865    0.4497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3788   -2.3501   -1.2380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7343   -3.1101   -0.9372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8356    0.6431   -1.6178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7671   -0.4830   -0.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6533    0.5706    0.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2887   -1.4946   -2.8127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5842   -1.7984   -2.4529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2268   -0.0811   -2.7247 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  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 17 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  0
  6 39  1  0
  7 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
 10 45  1  0
 11 46  1  0
 11 47  1  0
 12 48  1  0
 12 49  1  0
 13 50  1  0
 13 51  1  0
 17 52  1  0
 18 53  1  0
 18 54  1  0
 22 55  1  0
 22 56  1  0
 24 57  1  0
 24 58  1  0
 24 59  1  0
 25 60  1  0
 25 61  1  0
 25 62  1  0
 26 63  1  0
 26 64  1  0
 26 65  1  0
M  CHG  2  21  -1  23   1
M  END

HMDB02014.mol
  Mrv0541 02231219192D          

 26 25  0  0  0  0            999 V2000
   -5.0012    0.2063    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -4.2867    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5722    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8578    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8578    1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5722    1.8562    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -5.4137    0.9207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7156   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8569   -0.6232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5722   -0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8578   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5722    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2867    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0012    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7156    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8578   -1.8562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.8562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  7  1  0  0  0  0
  1  8  1  0  0  0  0
  1  9  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 15  2  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
 21 20  1  0  0  0  0
 22 21  1  0  0  0  0
 22 23  1  0  0  0  0
 11 24  2  0  0  0  0
  5 25  2  0  0  0  0
 13 26  1  0  0  0  0
 26 14  1  0  0  0  0
 16 15  1  0  0  0  0
M  CHG  2   1   1   6  -1
M  END
> <DATABASE_ID>
HMDB0002014

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCC\C=C/CCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C21H39NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-21(25)26-19(17-20(23)24)18-22(2,3)4/h12-13,19H,5-11,14-18H2,1-4H3/b13-12-

> <INCHI_KEY>
NNCBVXBBLABOCB-SEYXRHQNSA-N

> <FORMULA>
C21H39NO4

> <MOLECULAR_WEIGHT>
369.5387

> <EXACT_MASS>
369.287908741

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
44.59717913488928

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[(5Z)-tetradec-5-enoyloxy]-4-(trimethylazaniumyl)butanoate

> <ALOGPS_LOGP>
0.48

> <JCHEM_LOGP>
0.7824888675282539

> <ALOGPS_LOGS>
-7.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.235690941127461

> <JCHEM_PKA_STRONGEST_BASIC>
-7.05730458065797

> <JCHEM_POLAR_SURFACE_AREA>
66.43

> <JCHEM_REFRACTIVITY>
128.9913

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.71e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cis-5-tetradecenoylcarnitine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002014
     RDKit          3D
cis-5-Tetradecenoylcarnitine
 65 64  0  0  0  0  0  0  0  0999 V2000
    9.0404   -1.1535   -2.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8628   -1.2800   -1.0769 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9265   -0.1547   -1.4060 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6789   -0.1914   -0.5229 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0508   -0.0685    0.8958 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0205   -0.0411    1.9394 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0522    1.0435    2.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1364    1.3644    0.9317 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1768    2.4379    1.3174 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9002    2.2558    1.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2386    1.0160    0.9088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5929    0.4839    2.0627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3153   -0.7869    1.7443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2642   -0.6056    0.5875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8987   -0.7377   -0.5861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5979   -0.2785    0.8226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5386   -0.0966   -0.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0176    1.3548   -0.2505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8189    2.2212   -0.4459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0269    2.4205    0.5099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5611    2.8144   -1.6713 O   0  0  0  0  0  1  0  0  0  0  0  0
   -5.6757   -0.9992    0.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7570   -1.0399   -0.8802 N   0  0  0  0  0  4  0  0  0  0  0  0
   -7.4355   -2.3305   -0.6424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7647   -0.0153   -0.7178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3920   -1.0605   -2.2772 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6019   -0.2223   -1.7917 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6938   -2.0244   -1.9642 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6283   -1.0570   -3.0597 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3935   -2.2629   -1.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2583   -1.1517   -0.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5940   -0.1728   -2.4645 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4785    0.7986   -1.2511 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9139    0.4450   -0.9374 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2632   -1.2561   -0.6854 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7295    0.8206    1.0436 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7376   -0.9445    1.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3948   -1.0068    1.8367 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5432   -0.2684    2.9322 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5260    2.0112    2.4649 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3911    0.7681    2.9714 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7344    0.4678    0.5190 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7729    1.9090    0.1422 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6367    3.3948    1.6208 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2834    3.1282    1.6058 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8160    0.2510    0.4111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5352    1.3205    0.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1147    0.2652    2.8885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2654    1.2814    2.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5998   -1.5553    1.4426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8704   -1.1124    2.6367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9733   -0.2813   -1.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7027    1.5695   -1.0782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5477    1.5990    0.6892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0728   -0.7513    1.0412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2679   -2.0448    0.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6289   -2.3865    0.4497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3788   -2.3501   -1.2380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7343   -3.1101   -0.9372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8356    0.6431   -1.6178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7671   -0.4830   -0.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6533    0.5706    0.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2887   -1.4946   -2.8127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5842   -1.7984   -2.4529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2268   -0.0811   -2.7247 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  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 17 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  0
  6 39  1  0
  7 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
 10 45  1  0
 11 46  1  0
 11 47  1  0
 12 48  1  0
 12 49  1  0
 13 50  1  0
 13 51  1  0
 17 52  1  0
 18 53  1  0
 18 54  1  0
 22 55  1  0
 22 56  1  0
 24 57  1  0
 24 58  1  0
 24 59  1  0
 25 60  1  0
 25 61  1  0
 25 62  1  0
 26 63  1  0
 26 64  1  0
 26 65  1  0
M  CHG  2  21  -1  23   1
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: HMDB02014.mol                                     
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0      -9.336   0.385   0.000  0.00  0.00           N+1
HETATM    2  C   UNK     0      -8.002   1.155   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.668   0.385   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335   1.155   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.335   2.695   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -6.668   3.465   0.000  0.00  0.00           O-1
HETATM    7  C   UNK     0     -10.106   1.719   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -10.669  -0.385   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -9.066  -1.163   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -6.668  -1.155   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -5.335  -1.925   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001  -1.155   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667  -1.925   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  -1.925   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -1.155   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   0.385   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   1.155   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001   0.385   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335   1.155   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668   0.385   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002   1.155   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.336   0.385   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.669   1.155   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -5.335  -3.465   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -4.001   3.465   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -1.334  -1.155   0.000  0.00  0.00           C+0
CONECT    1    2    7    8    9                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   25                                                  
CONECT    6    5                                                            
CONECT    7    1                                                            
CONECT    8    1                                                            
CONECT    9    1                                                            
CONECT   10    3   11                                                       
CONECT   11   10   12   24                                                  
CONECT   12   11   13                                                       
CONECT   13   12   26                                                       
CONECT   14   15   26                                                       
CONECT   15   14   16                                                       
CONECT   16   17   15                                                       
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                                                            
CONECT   24   11                                                            
CONECT   25    5                                                            
CONECT   26   13   14                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   50    0
END

COMPND    HMDB0002014
HETATM    1  C1  UNL     1       9.040  -1.153  -2.044  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.863  -1.280  -1.077  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.927  -0.155  -1.406  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.679  -0.191  -0.523  1.00  0.00           C  
HETATM    5  C5  UNL     1       6.051  -0.069   0.896  1.00  0.00           C  
HETATM    6  C6  UNL     1       5.021  -0.041   1.939  1.00  0.00           C  
HETATM    7  C7  UNL     1       4.052   1.043   2.078  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.136   1.364   0.932  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.177   2.438   1.317  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.900   2.256   1.298  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.239   1.016   0.909  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.593   0.484   2.063  1.00  0.00           C  
HETATM   13  C13 UNL     1      -1.315  -0.787   1.744  1.00  0.00           C  
HETATM   14  C14 UNL     1      -2.264  -0.606   0.588  1.00  0.00           C  
HETATM   15  O1  UNL     1      -1.899  -0.738  -0.586  1.00  0.00           O  
HETATM   16  O2  UNL     1      -3.598  -0.279   0.823  1.00  0.00           O  
HETATM   17  C15 UNL     1      -4.539  -0.097  -0.253  1.00  0.00           C  
HETATM   18  C16 UNL     1      -5.018   1.355  -0.251  1.00  0.00           C  
HETATM   19  C17 UNL     1      -3.819   2.221  -0.446  1.00  0.00           C  
HETATM   20  O3  UNL     1      -3.027   2.420   0.510  1.00  0.00           O  
HETATM   21  O4  UNL     1      -3.561   2.814  -1.671  1.00  0.00           O1-
HETATM   22  C18 UNL     1      -5.676  -0.999   0.023  1.00  0.00           C  
HETATM   23  N1  UNL     1      -6.757  -1.040  -0.880  1.00  0.00           N1+
HETATM   24  C19 UNL     1      -7.435  -2.330  -0.642  1.00  0.00           C  
HETATM   25  C20 UNL     1      -7.765  -0.015  -0.718  1.00  0.00           C  
HETATM   26  C21 UNL     1      -6.392  -1.061  -2.277  1.00  0.00           C  
HETATM   27  H1  UNL     1       9.602  -0.222  -1.792  1.00  0.00           H  
HETATM   28  H2  UNL     1       9.694  -2.024  -1.964  1.00  0.00           H  
HETATM   29  H3  UNL     1       8.628  -1.057  -3.060  1.00  0.00           H  
HETATM   30  H4  UNL     1       7.393  -2.263  -1.113  1.00  0.00           H  
HETATM   31  H5  UNL     1       8.258  -1.152  -0.023  1.00  0.00           H  
HETATM   32  H6  UNL     1       6.594  -0.173  -2.465  1.00  0.00           H  
HETATM   33  H7  UNL     1       7.479   0.799  -1.251  1.00  0.00           H  
HETATM   34  H8  UNL     1       4.914   0.445  -0.937  1.00  0.00           H  
HETATM   35  H9  UNL     1       5.263  -1.256  -0.685  1.00  0.00           H  
HETATM   36  H10 UNL     1       6.729   0.821   1.044  1.00  0.00           H  
HETATM   37  H11 UNL     1       6.738  -0.944   1.156  1.00  0.00           H  
HETATM   38  H12 UNL     1       4.395  -1.007   1.837  1.00  0.00           H  
HETATM   39  H13 UNL     1       5.543  -0.268   2.932  1.00  0.00           H  
HETATM   40  H14 UNL     1       4.526   2.011   2.465  1.00  0.00           H  
HETATM   41  H15 UNL     1       3.391   0.768   2.971  1.00  0.00           H  
HETATM   42  H16 UNL     1       2.734   0.468   0.519  1.00  0.00           H  
HETATM   43  H17 UNL     1       3.773   1.909   0.142  1.00  0.00           H  
HETATM   44  H18 UNL     1       2.637   3.395   1.621  1.00  0.00           H  
HETATM   45  H19 UNL     1       0.283   3.128   1.606  1.00  0.00           H  
HETATM   46  H20 UNL     1       0.816   0.251   0.411  1.00  0.00           H  
HETATM   47  H21 UNL     1      -0.535   1.321   0.125  1.00  0.00           H  
HETATM   48  H22 UNL     1       0.115   0.265   2.889  1.00  0.00           H  
HETATM   49  H23 UNL     1      -1.265   1.281   2.434  1.00  0.00           H  
HETATM   50  H24 UNL     1      -0.600  -1.555   1.443  1.00  0.00           H  
HETATM   51  H25 UNL     1      -1.870  -1.112   2.637  1.00  0.00           H  
HETATM   52  H26 UNL     1      -3.973  -0.281  -1.179  1.00  0.00           H  
HETATM   53  H27 UNL     1      -5.703   1.570  -1.078  1.00  0.00           H  
HETATM   54  H28 UNL     1      -5.548   1.599   0.689  1.00  0.00           H  
HETATM   55  H29 UNL     1      -6.073  -0.751   1.041  1.00  0.00           H  
HETATM   56  H30 UNL     1      -5.268  -2.045   0.141  1.00  0.00           H  
HETATM   57  H31 UNL     1      -7.629  -2.387   0.450  1.00  0.00           H  
HETATM   58  H32 UNL     1      -8.379  -2.350  -1.238  1.00  0.00           H  
HETATM   59  H33 UNL     1      -6.734  -3.110  -0.937  1.00  0.00           H  
HETATM   60  H34 UNL     1      -7.836   0.643  -1.618  1.00  0.00           H  
HETATM   61  H35 UNL     1      -8.767  -0.483  -0.644  1.00  0.00           H  
HETATM   62  H36 UNL     1      -7.653   0.571   0.216  1.00  0.00           H  
HETATM   63  H37 UNL     1      -7.289  -1.495  -2.813  1.00  0.00           H  
HETATM   64  H38 UNL     1      -5.584  -1.798  -2.453  1.00  0.00           H  
HETATM   65  H39 UNL     1      -6.227  -0.081  -2.725  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3   30   31
CONECT    3    4   32   33
CONECT    4    5   34   35
CONECT    5    6   36   37
CONECT    6    7   38   39
CONECT    7    8   40   41
CONECT    8    9   42   43
CONECT    9   10   10   44
CONECT   10   11   45
CONECT   11   12   46   47
CONECT   12   13   48   49
CONECT   13   14   50   51
CONECT   14   15   15   16
CONECT   16   17
CONECT   17   18   22   52
CONECT   18   19   53   54
CONECT   19   20   20   21
CONECT   22   23   55   56
CONECT   23   24   25   26
CONECT   24   57   58   59
CONECT   25   60   61   62
CONECT   26   63   64   65
END

HMDB0002014
     RDKit          3D
cis-5-Tetradecenoylcarnitine
 65 64  0  0  0  0  0  0  0  0999 V2000
    9.0404   -1.1535   -2.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8628   -1.2800   -1.0769 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9265   -0.1547   -1.4060 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6789   -0.1914   -0.5229 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0508   -0.0685    0.8958 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0205   -0.0411    1.9394 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0522    1.0435    2.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1364    1.3644    0.9317 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1768    2.4379    1.3174 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9002    2.2558    1.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2386    1.0160    0.9088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5929    0.4839    2.0627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3153   -0.7869    1.7443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2642   -0.6056    0.5875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8987   -0.7377   -0.5861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5979   -0.2785    0.8226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5386   -0.0966   -0.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0176    1.3548   -0.2505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8189    2.2212   -0.4459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0269    2.4205    0.5099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5611    2.8144   -1.6713 O   0  0  0  0  0  1  0  0  0  0  0  0
   -5.6757   -0.9992    0.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7570   -1.0399   -0.8802 N   0  0  0  0  0  4  0  0  0  0  0  0
   -7.4355   -2.3305   -0.6424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7647   -0.0153   -0.7178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3920   -1.0605   -2.2772 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6019   -0.2223   -1.7917 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6938   -2.0244   -1.9642 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6283   -1.0570   -3.0597 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3935   -2.2629   -1.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2583   -1.1517   -0.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5940   -0.1728   -2.4645 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4785    0.7986   -1.2511 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9139    0.4450   -0.9374 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2632   -1.2561   -0.6854 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7295    0.8206    1.0436 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7376   -0.9445    1.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3948   -1.0068    1.8367 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5432   -0.2684    2.9322 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5260    2.0112    2.4649 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3911    0.7681    2.9714 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7344    0.4678    0.5190 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7729    1.9090    0.1422 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6367    3.3948    1.6208 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2834    3.1282    1.6058 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8160    0.2510    0.4111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5352    1.3205    0.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1147    0.2652    2.8885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2654    1.2814    2.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5998   -1.5553    1.4426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8704   -1.1124    2.6367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9733   -0.2813   -1.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7027    1.5695   -1.0782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5477    1.5990    0.6892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0728   -0.7513    1.0412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2679   -2.0448    0.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6289   -2.3865    0.4497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3788   -2.3501   -1.2380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7343   -3.1101   -0.9372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8356    0.6431   -1.6178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7671   -0.4830   -0.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6533    0.5706    0.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2887   -1.4946   -2.8127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5842   -1.7984   -2.4529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2268   -0.0811   -2.7247 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  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 17 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  0
  6 39  1  0
  7 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
 10 45  1  0
 11 46  1  0
 11 47  1  0
 12 48  1  0
 12 49  1  0
 13 50  1  0
 13 51  1  0
 17 52  1  0
 18 53  1  0
 18 54  1  0
 22 55  1  0
 22 56  1  0
 24 57  1  0
 24 58  1  0
 24 59  1  0
 25 60  1  0
 25 61  1  0
 25 62  1  0
 26 63  1  0
 26 64  1  0
 26 65  1  0
M  CHG  2  21  -1  23   1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-[(5Z)-Tetradec-5-enoyloxy]-4-(trimethylammonio)butanoate	ChEBI
3-[(5Z)-Tetradec-5-enoyloxy]-4-(trimethylammonio)butanoic acid	Generator
cis-5-Tetradecenoylcarnitine	ChEBI

Chemical Formula

C₂₁H₃₉NO₄

Average Molecular Weight

369.5387

Monoisotopic Molecular Weight

369.287908741

IUPAC Name

3-[(5Z)-tetradec-5-enoyloxy]-4-(trimethylazaniumyl)butanoate

Traditional Name

cis-5-tetradecenoylcarnitine

CAS Registry Number

835598-21-5

SMILES

CCCCCCCC\C=C/CCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C

InChI Identifier

InChI=1S/C21H39NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-21(25)26-19(17-20(23)24)18-22(2,3)4/h12-13,19H,5-11,14-18H2,1-4H3/b13-12-

InChI Key

NNCBVXBBLABOCB-SEYXRHQNSA-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

O-acylcarnitine (CHEBI:73060 )

Ontology

Physiological effect

Health effect

Cancer

Breast cancer (PMID: 35710135)

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

Circulatory system disorder

Cardiac disorder

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

Renal system and urinary system

Renal disorder

Renal cell carcinoma (PMID: 35710135)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 9034211)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Cellular substructure

Organelle

peroxisome (PMID: 35710135)

Cell

All cells and tissues (PMID: 35710135)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Process

Not Available

Role

Biological role

Energy source (PMID: 35710135)

Industrial application

Pharmaceutical industry

Biomarker

Physical Properties

State

Solid

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.7e-05 g/L	ALOGPS
logP	0.48	ALOGPS
logP	0.78	ChemAxon
logS	-7.4	ALOGPS
pKa (Strongest Acidic)	4.24	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	17	ChemAxon
Refractivity	128.99 m³·mol⁻¹	ChemAxon
Polarizability	44.6 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	210.23	30932474
DeepCCS	[M-H]-	206.21	30932474
DeepCCS	[M-2H]-	242.754	30932474
DeepCCS	[M+Na]+	219.045	30932474
AllCCS	[M+H]+	204.2	32859911
AllCCS	[M+H-H2O]+	202.0	32859911
AllCCS	[M+NH4]+	206.2	32859911
AllCCS	[M+Na]+	206.8	32859911
AllCCS	[M-H]-	199.3	32859911
AllCCS	[M+Na-2H]-	201.0	32859911
AllCCS	[M+HCOO]-	202.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
cis-5-Tetradecenoylcarnitine	CCCCCCCC\C=C/CCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C	2922.5	Standard polar	33892256
cis-5-Tetradecenoylcarnitine	CCCCCCCC\C=C/CCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C	2227.3	Standard non polar	33892256
cis-5-Tetradecenoylcarnitine	CCCCCCCC\C=C/CCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C	2441.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - cis-5-Tetradecenoylcarnitine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-9210000000-d55933555203a81af3b0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cis-5-Tetradecenoylcarnitine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cis-5-Tetradecenoylcarnitine 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 - cis-5-Tetradecenoylcarnitine 10V, Positive-QTOF	splash10-0fkc-0729000000-b7724178fd672abeda7c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-5-Tetradecenoylcarnitine 20V, Positive-QTOF	splash10-0006-1900000000-a2f60fad8c99a570c7b0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-5-Tetradecenoylcarnitine 40V, Positive-QTOF	splash10-02fx-4900000000-6ae1e898595b8e8b61f5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-5-Tetradecenoylcarnitine 10V, Negative-QTOF	splash10-014i-0029000000-a5108e2a8a5c949c7942	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-5-Tetradecenoylcarnitine 20V, Negative-QTOF	splash10-0aor-1289000000-351e00d1ad0b6a3015e9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-5-Tetradecenoylcarnitine 40V, Negative-QTOF	splash10-0a6u-7590000000-8eeb0dac52aa2c1d6246	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-5-Tetradecenoylcarnitine 10V, Positive-QTOF	splash10-00di-0009000000-1a5965dc435463ee085f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-5-Tetradecenoylcarnitine 20V, Positive-QTOF	splash10-0079-9005000000-84dcf946c3b41ee8ec83	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-5-Tetradecenoylcarnitine 40V, Positive-QTOF	splash10-000i-9000000000-e9262cbaff8cb4ad0ba6	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.06 +/- 0.03 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	0.020-0.240 uM	Adult (>18 years old)	Both	Normal	Molecular You	details
Blood	Detected and Quantified	0.03 (0.03-0.04) uM	Newborn (0-30 days old)	Not Available	Normal	25754623	details
Blood	Detected and Quantified	0.020-0.240 uM	Adult (>18 years old)	Both	Normal	Molecular You	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	0.08 (0.06-0.11) uM	Infant (0-1 year old)	Not Available	Normal	25754623	details
Blood	Detected and Quantified	<1 uM	Newborn (0-30 days old)	Not Specified	Normal	16950999	details
Blood	Detected and Quantified	0.032 (0.005-0.097) uM	Children (1-13 years old)	Both	Normal	9034211	details
Urine	Detected and Quantified	0.0038 +/- 0.0015 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.1014 (0.0757) uM	Adult (>18 years old)	Female	Pregnancy with fetus having congenital heart defect	24704061	details
Blood	Detected and Quantified	0.122 +/- 0.042 uM	Children (1-13 years old)	Both	Obesity	Metabolomics reve...	details
Blood	Detected and Quantified	0.131 +/- 0.048 uM	Children (1-13 years old)	Both	Obesity	Metabolomics reve...	details
Blood	Detected and Quantified	5.223 (2.658-7.891) uM	Adult (>18 years old)	Both	Very long-chain acyl-CoA dehydrogenase deficiency (vLCAD)	9034211	details
Urine	Detected and Quantified	0.0039 +/- 0.0013 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected and Quantified	0.0089 +/- 0.0114 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Gastroesophageal reflux disease	Analysis of 30 no...	details

Associated Disorders and Diseases

Disease References

Very Long Chain Acyl-CoA Dehydrogenase Deficiency
Costa CG, Struys EA, Bootsma A, ten Brink HJ, Dorland L, Tavares de Almeida I, Duran M, Jakobs C: Quantitative analysis of plasma acylcarnitines using gas chromatography chemical ionization mass fragmentography. J Lipid Res. 1997 Jan;38(1):173-82. [PubMed:9034211 ]
Obesity
Simone Wahl, Christina Holzapfel, Zhonghao Yu, Michaela Breier, Ivan Kondofersky, Christiane Fuchs, Paula Singmann, Cornelia Prehn, Jerzy Adamski, Harald Grallert, Thomas Illig, Rui Wang-Sattler, Thomas Reinehr (2013). Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children. Metabolomics.
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

201475 (Very Long Chain Acyl-CoA Dehydrogenase Deficiency)
601665 (Obesity)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022796

KNApSAcK ID

Not Available

Chemspider ID

17216151

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6437

PubChem Compound

22833575

PDB ID

Not Available

ChEBI ID

73060

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000366

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Strauss AW, Powell CK, Hale DE, Anderson MM, Ahuja A, Brackett JC, Sims HF: Molecular basis of human mitochondrial very-long-chain acyl-CoA dehydrogenase deficiency causing cardiomyopathy and sudden death in childhood. Proc Natl Acad Sci U S A. 1995 Nov 7;92(23):10496-500. [PubMed:7479827 ]
Shigematsu Y, Hirano S, Hata I, Tanaka Y, Sudo M, Tajima T, Sakura N, Yamaguchi S, Takayanagi M: Selective screening for fatty acid oxidation disorders by tandem mass spectrometry: difficulties in practical discrimination. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):63-72. [PubMed:12828998 ]
Wood JC, Magera MJ, Rinaldo P, Seashore MR, Strauss AW, Friedman A: Diagnosis of very long chain acyl-dehydrogenase deficiency from an infant's newborn screening card. Pediatrics. 2001 Jul;108(1):E19. [PubMed:11433098 ]
Archie JP Jr: Splenic artery stump back pressure. Am Surg. 1992 Aug;58(8):504-5. [PubMed:1642390 ]
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Showing metabocard for cis-5-Tetradecenoylcarnitine (HMDB0002014)

MOL for HMDB0002014 (cis-5-Tetradecenoylcarnitine)

3D MOL for HMDB0002014 (cis-5-Tetradecenoylcarnitine)

3D SDF for HMDB0002014 (cis-5-Tetradecenoylcarnitine)

3D-SDF for HMDB0002014 (cis-5-Tetradecenoylcarnitine)

PDB for HMDB0002014 (cis-5-Tetradecenoylcarnitine)

3D PDB for HMDB0002014 (cis-5-Tetradecenoylcarnitine)

SMILES for HMDB0002014 (cis-5-Tetradecenoylcarnitine)

INCHI for HMDB0002014 (cis-5-Tetradecenoylcarnitine)

Structure for HMDB0002014 (cis-5-Tetradecenoylcarnitine)

3D Structure for HMDB0002014 (cis-5-Tetradecenoylcarnitine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra