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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2009-11-30 15:50:58 UTC

Update Date

2023-05-30 20:55:49 UTC

HMDB ID

HMDB0013207

Secondary Accession Numbers

HMDB13207

Metabolite Identification

Common Name

9-Hexadecenoylcarnitine

Description

9-Hexadecenoylcarnitine is an acylcarnitine. More specifically, it is an 9-hexadecenoic acid ester of carnitine. Acylcarnitines were first discovered more than 70 year ago (PMID: 13825279 ). It is believed that there are more than 1000 types of acylcarnitines in the human body. The general role of acylcarnitines is to transport acyl-groups (organic acids and fatty acids) from the cytoplasm into the mitochondria so that they can be broken down to produce energy. This process is known as beta-oxidation. According to a recent review (PMID: 35710135 ), acylcarnitines (ACs) can be classified into 9 different categories depending on the type and size of their acyl-group: 1) short-chain ACs; 2) medium-chain ACs; 3) long-chain ACs; 4) very long-chain ACs; 5) hydroxy ACs; 6) branched chain ACs; 7) unsaturated ACs; 8) dicarboxylic ACs and 9) miscellaneous ACs. Short-chain ACs have acyl-groups with two to five carbons (C2-C5), medium-chain ACs have acyl-groups with six to thirteen carbons (C6-C13), long-chain ACs have acyl-groups with fourteen to twenty once carbons (C14-C21) and very long-chain ACs have acyl groups with more than 22 carbons. 9-Hexadecenoylcarnitine is therefore classified as a long chain AC. As a long-chain acylcarnitine 9-hexadecenoylcarnitine 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 9-hexadecenoylcarnitine is elevated in the blood or plasma of individuals with children obesity (PMID: 23108202 ). It is also decreased in the blood or plasma of individuals with familial Mediterranean fever (PMID: 29900937 ). 9-Hexadecenoylcarnitine is found to be associated with glutaric aciduria II, which is an inborn error of 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

      
  Mrv1652303081900382D          

 28 27  0  0  0  0            999 V2000
 9995.879710001.0029    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9996.593810000.5896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.307910001.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.022010000.5896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.736110001.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.450210000.5896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.164210001.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.878310000.5896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.593310001.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.307010000.5896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.020610001.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.845710001.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.561510000.5896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.275210001.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.988710000.5896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.702510001.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.418210000.5896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.131910001.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.307910001.8274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.879710001.8274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.165610002.2379    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
 9994.447310001.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.165610003.0629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.312510002.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.173910000.5793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.1739 9999.7549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.8880 9999.3415    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
 9994.4598 9999.3415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 20  1  6  0  0  0
  1 25  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 19  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
M  CHG  2  21   1  27  -1
M  END

HMDB0013207
     RDKit          3D
9-Hexadecenoylcarnitine
 71 70  0  0  0  0  0  0  0  0999 V2000
   10.3224    0.3413    1.0832 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1204    0.8116    1.8632 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0175    1.2894    0.9369 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5850    0.1742    0.0377 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4957    0.6244   -0.8827 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2452    1.0964   -0.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6825    0.0316    0.6973 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4618   -0.4312    0.5496 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5055    0.0665   -0.4661 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0978   -1.0476   -1.4198 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4225   -2.1915   -0.8113 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1076   -2.1103   -0.1585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0203   -1.7715   -1.0347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1764   -0.4625   -1.6683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4205    0.6441   -0.6497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7102    0.2623    0.0505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6187   -0.0747    1.2509 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9059    0.3026   -0.6562 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0940   -0.0818    0.1310 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4563   -1.4152   -0.5152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5793   -2.1303    0.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6826   -2.1966   -0.5601 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4889   -2.7997    1.2435 O   0  0  0  0  0  1  0  0  0  0  0  0
   -6.0413    1.0195   -0.1534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3064    1.0757    0.4602 N   0  0  0  0  0  4  0  0  0  0  0  0
   -7.5527    0.2676    1.6002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3387    0.9127   -0.5853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5400    2.4842    0.9076 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1618   -0.7049    0.6908 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4406    0.9620    0.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2573    0.4101    1.6650 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7195   -0.0083    2.4755 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4412    1.6923    2.4798 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2098    1.6491    1.5758 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3746    2.1117    0.2704 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3306   -0.7527    0.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4543   -0.0911   -0.6047 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2052   -0.1060   -1.6368 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8611    1.5282   -1.4230 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5293    1.9945    0.5014 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5839    1.5036   -0.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2950   -0.4390    1.5094 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1324   -1.2480    1.2357 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5789    0.3250    0.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7735    0.9831   -0.9826 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7006   -0.6341   -2.3551 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1317   -1.4479   -1.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3951   -3.0681   -1.5648 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1678   -2.6400   -0.0522 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1238   -1.4782    0.7780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1198   -3.1540    0.2551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9714   -1.9447   -0.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1271   -2.6012   -1.8182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1872   -0.5101   -2.2312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4860   -0.1566   -2.4517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6221    0.6297    0.0818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5138    1.6279   -1.1477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7821   -0.2611    1.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5600   -2.1101   -0.4630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5303   -1.2182   -1.6301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5385    2.0365    0.0042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1798    1.0404   -1.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9587    0.9340    2.4296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3575   -0.4895    1.4898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6109   -0.1179    2.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5631    1.9113   -1.0368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2176    0.3768   -0.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8640    0.3528   -1.4447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6327    2.6302    0.9644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0776    2.6298    1.8829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0997    3.1614    0.1472 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  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 19 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 25 28  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  0
  8 43  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  0
 10 47  1  0
 11 48  1  0
 11 49  1  0
 12 50  1  0
 12 51  1  0
 13 52  1  0
 13 53  1  0
 14 54  1  0
 14 55  1  0
 15 56  1  0
 15 57  1  0
 19 58  1  1
 20 59  1  0
 20 60  1  0
 24 61  1  0
 24 62  1  0
 26 63  1  0
 26 64  1  0
 26 65  1  0
 27 66  1  0
 27 67  1  0
 27 68  1  0
 28 69  1  0
 28 70  1  0
 28 71  1  0
M  CHG  2  23  -1  25   1
M  END

      
  Mrv1652303081900382D          

 28 27  0  0  0  0            999 V2000
 9995.879710001.0029    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9996.593810000.5896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.307910001.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.022010000.5896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.736110001.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.450210000.5896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.164210001.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.878310000.5896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.593310001.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.307010000.5896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.020610001.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.845710001.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.561510000.5896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.275210001.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.988710000.5896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.702510001.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.418210000.5896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.131910001.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.307910001.8274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.879710001.8274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.165610002.2379    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
 9994.447310001.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.165610003.0629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.312510002.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.173910000.5793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.1739 9999.7549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.8880 9999.3415    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
 9994.4598 9999.3415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 20  1  6  0  0  0
  1 25  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 19  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
M  CHG  2  21   1  27  -1
M  END
> <DATABASE_ID>
HMDB0013207

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C23H43NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(27)28-21(19-22(25)26)20-24(2,3)4/h10-11,21H,5-9,12-20H2,1-4H3/b11-10-/t21-/m1/s1

> <INCHI_KEY>
JFAGPSOZZSTLRF-KUFMOJEASA-N

> <FORMULA>
C23H43NO4

> <MOLECULAR_WEIGHT>
397.6

> <EXACT_MASS>
397.319208869

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
48.8332856600807

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R)-3-[(9Z)-hexadec-9-enoyloxy]-4-(trimethylazaniumyl)butanoate

> <ALOGPS_LOGP>
1.03

> <JCHEM_LOGP>
1.6716261975282545

> <ALOGPS_LOGS>
-7.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.216763902737658

> <JCHEM_PKA_STRONGEST_BASIC>
-7.0571868920224

> <JCHEM_POLAR_SURFACE_AREA>
66.43

> <JCHEM_REFRACTIVITY>
138.1933

> <JCHEM_ROTATABLE_BOND_COUNT>
19

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.72e-06 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-3-[(9Z)-hexadec-9-enoyloxy]-4-(trimethylammonio)butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013207
     RDKit          3D
9-Hexadecenoylcarnitine
 71 70  0  0  0  0  0  0  0  0999 V2000
   10.3224    0.3413    1.0832 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1204    0.8116    1.8632 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0175    1.2894    0.9369 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5850    0.1742    0.0377 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4957    0.6244   -0.8827 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2452    1.0964   -0.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6825    0.0316    0.6973 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4618   -0.4312    0.5496 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5055    0.0665   -0.4661 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0978   -1.0476   -1.4198 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4225   -2.1915   -0.8113 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1076   -2.1103   -0.1585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0203   -1.7715   -1.0347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1764   -0.4625   -1.6683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4205    0.6441   -0.6497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7102    0.2623    0.0505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6187   -0.0747    1.2509 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9059    0.3026   -0.6562 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0940   -0.0818    0.1310 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4563   -1.4152   -0.5152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5793   -2.1303    0.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6826   -2.1966   -0.5601 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4889   -2.7997    1.2435 O   0  0  0  0  0  1  0  0  0  0  0  0
   -6.0413    1.0195   -0.1534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3064    1.0757    0.4602 N   0  0  0  0  0  4  0  0  0  0  0  0
   -7.5527    0.2676    1.6002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3387    0.9127   -0.5853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5400    2.4842    0.9076 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1618   -0.7049    0.6908 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4406    0.9620    0.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2573    0.4101    1.6650 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7195   -0.0083    2.4755 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4412    1.6923    2.4798 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2098    1.6491    1.5758 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3746    2.1117    0.2704 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3306   -0.7527    0.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4543   -0.0911   -0.6047 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2052   -0.1060   -1.6368 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8611    1.5282   -1.4230 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5293    1.9945    0.5014 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5839    1.5036   -0.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2950   -0.4390    1.5094 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1324   -1.2480    1.2357 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5789    0.3250    0.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7735    0.9831   -0.9826 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7006   -0.6341   -2.3551 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1317   -1.4479   -1.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3951   -3.0681   -1.5648 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1678   -2.6400   -0.0522 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1238   -1.4782    0.7780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1198   -3.1540    0.2551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9714   -1.9447   -0.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1271   -2.6012   -1.8182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1872   -0.5101   -2.2312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4860   -0.1566   -2.4517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6221    0.6297    0.0818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5138    1.6279   -1.1477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7821   -0.2611    1.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5600   -2.1101   -0.4630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5303   -1.2182   -1.6301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5385    2.0365    0.0042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1798    1.0404   -1.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9587    0.9340    2.4296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3575   -0.4895    1.4898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6109   -0.1179    2.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5631    1.9113   -1.0368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2176    0.3768   -0.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8640    0.3528   -1.4447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6327    2.6302    0.9644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0776    2.6298    1.8829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0997    3.1614    0.1472 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  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 19 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 25 28  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  0
  8 43  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  0
 10 47  1  0
 11 48  1  0
 11 49  1  0
 12 50  1  0
 12 51  1  0
 13 52  1  0
 13 53  1  0
 14 54  1  0
 14 55  1  0
 15 56  1  0
 15 57  1  0
 19 58  1  1
 20 59  1  0
 20 60  1  0
 24 61  1  0
 24 62  1  0
 26 63  1  0
 26 64  1  0
 26 65  1  0
 27 66  1  0
 27 67  1  0
 27 68  1  0
 28 69  1  0
 28 70  1  0
 28 71  1  0
M  CHG  2  23  -1  25   1
M  END

HEADER    PROTEIN                                 08-MAR-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-MAR-19         0                                  
HETATM    1  C   UNK     0    8658.9758668.539   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8660.3088667.767   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8661.6418668.539   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8662.9748667.767   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8664.3078668.539   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8665.6408667.767   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8666.9738668.539   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8668.3068667.767   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8669.6418668.539   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8670.9738667.767   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8672.3058668.539   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8673.8458668.539   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8675.1818667.767   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8676.5148668.539   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8677.8468667.767   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8679.1788668.539   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8680.5148667.767   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8681.8468668.539   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0    8661.6418670.078   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0    8658.9758670.078   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0    8657.6428670.844   0.000  0.00  0.00           N+1
HETATM   22  C   UNK     0    8656.3028670.074   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8657.6428672.384   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8656.0508671.764   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8657.6588667.748   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8657.6588666.209   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0    8658.9918665.437   0.000  0.00  0.00           O-1
HETATM   28  O   UNK     0    8656.3258665.437   0.000  0.00  0.00           O+0
CONECT    1    2   20   25                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19    3                                                            
CONECT   20    1   21                                                       
CONECT   21   20   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21                                                            
CONECT   25    1   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   54    0
END

COMPND    HMDB0013207
HETATM    1  C1  UNL     1      10.322   0.341   1.083  1.00  0.00           C  
HETATM    2  C2  UNL     1       9.120   0.812   1.863  1.00  0.00           C  
HETATM    3  C3  UNL     1       8.018   1.289   0.937  1.00  0.00           C  
HETATM    4  C4  UNL     1       7.585   0.174   0.038  1.00  0.00           C  
HETATM    5  C5  UNL     1       6.496   0.624  -0.883  1.00  0.00           C  
HETATM    6  C6  UNL     1       5.245   1.096  -0.129  1.00  0.00           C  
HETATM    7  C7  UNL     1       4.682   0.032   0.697  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.462  -0.431   0.550  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.506   0.067  -0.466  1.00  0.00           C  
HETATM   10  C10 UNL     1       2.098  -1.048  -1.420  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.422  -2.192  -0.811  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.108  -2.110  -0.158  1.00  0.00           C  
HETATM   13  C13 UNL     1      -1.020  -1.772  -1.035  1.00  0.00           C  
HETATM   14  C14 UNL     1      -1.176  -0.463  -1.668  1.00  0.00           C  
HETATM   15  C15 UNL     1      -1.420   0.644  -0.650  1.00  0.00           C  
HETATM   16  C16 UNL     1      -2.710   0.262   0.051  1.00  0.00           C  
HETATM   17  O1  UNL     1      -2.619  -0.075   1.251  1.00  0.00           O  
HETATM   18  O2  UNL     1      -3.906   0.303  -0.656  1.00  0.00           O  
HETATM   19  C17 UNL     1      -5.094  -0.082   0.131  1.00  0.00           C  
HETATM   20  C18 UNL     1      -5.456  -1.415  -0.515  1.00  0.00           C  
HETATM   21  C19 UNL     1      -6.579  -2.130   0.021  1.00  0.00           C  
HETATM   22  O3  UNL     1      -7.683  -2.197  -0.560  1.00  0.00           O  
HETATM   23  O4  UNL     1      -6.489  -2.800   1.244  1.00  0.00           O1-
HETATM   24  C20 UNL     1      -6.041   1.020  -0.153  1.00  0.00           C  
HETATM   25  N1  UNL     1      -7.306   1.076   0.460  1.00  0.00           N1+
HETATM   26  C21 UNL     1      -7.553   0.268   1.600  1.00  0.00           C  
HETATM   27  C22 UNL     1      -8.339   0.913  -0.585  1.00  0.00           C  
HETATM   28  C23 UNL     1      -7.540   2.484   0.908  1.00  0.00           C  
HETATM   29  H1  UNL     1      10.162  -0.705   0.691  1.00  0.00           H  
HETATM   30  H2  UNL     1      10.441   0.962   0.168  1.00  0.00           H  
HETATM   31  H3  UNL     1      11.257   0.410   1.665  1.00  0.00           H  
HETATM   32  H4  UNL     1       8.720  -0.008   2.475  1.00  0.00           H  
HETATM   33  H5  UNL     1       9.441   1.692   2.480  1.00  0.00           H  
HETATM   34  H6  UNL     1       7.210   1.649   1.576  1.00  0.00           H  
HETATM   35  H7  UNL     1       8.375   2.112   0.270  1.00  0.00           H  
HETATM   36  H8  UNL     1       7.331  -0.753   0.592  1.00  0.00           H  
HETATM   37  H9  UNL     1       8.454  -0.091  -0.605  1.00  0.00           H  
HETATM   38  H10 UNL     1       6.205  -0.106  -1.637  1.00  0.00           H  
HETATM   39  H11 UNL     1       6.861   1.528  -1.423  1.00  0.00           H  
HETATM   40  H12 UNL     1       5.529   1.995   0.501  1.00  0.00           H  
HETATM   41  H13 UNL     1       4.584   1.504  -0.898  1.00  0.00           H  
HETATM   42  H14 UNL     1       5.295  -0.439   1.509  1.00  0.00           H  
HETATM   43  H15 UNL     1       3.132  -1.248   1.236  1.00  0.00           H  
HETATM   44  H16 UNL     1       1.579   0.325   0.134  1.00  0.00           H  
HETATM   45  H17 UNL     1       2.773   0.983  -0.983  1.00  0.00           H  
HETATM   46  H18 UNL     1       1.701  -0.634  -2.355  1.00  0.00           H  
HETATM   47  H19 UNL     1       3.132  -1.448  -1.767  1.00  0.00           H  
HETATM   48  H20 UNL     1       1.395  -3.068  -1.565  1.00  0.00           H  
HETATM   49  H21 UNL     1       2.168  -2.640  -0.052  1.00  0.00           H  
HETATM   50  H22 UNL     1       0.124  -1.478   0.778  1.00  0.00           H  
HETATM   51  H23 UNL     1      -0.120  -3.154   0.255  1.00  0.00           H  
HETATM   52  H24 UNL     1      -1.971  -1.945  -0.420  1.00  0.00           H  
HETATM   53  H25 UNL     1      -1.127  -2.601  -1.818  1.00  0.00           H  
HETATM   54  H26 UNL     1      -2.187  -0.510  -2.231  1.00  0.00           H  
HETATM   55  H27 UNL     1      -0.486  -0.157  -2.452  1.00  0.00           H  
HETATM   56  H28 UNL     1      -0.622   0.630   0.082  1.00  0.00           H  
HETATM   57  H29 UNL     1      -1.514   1.628  -1.148  1.00  0.00           H  
HETATM   58  H30 UNL     1      -4.782  -0.261   1.145  1.00  0.00           H  
HETATM   59  H31 UNL     1      -4.560  -2.110  -0.463  1.00  0.00           H  
HETATM   60  H32 UNL     1      -5.530  -1.218  -1.630  1.00  0.00           H  
HETATM   61  H33 UNL     1      -5.538   2.037   0.004  1.00  0.00           H  
HETATM   62  H34 UNL     1      -6.180   1.040  -1.285  1.00  0.00           H  
HETATM   63  H35 UNL     1      -7.959   0.934   2.430  1.00  0.00           H  
HETATM   64  H36 UNL     1      -8.358  -0.489   1.490  1.00  0.00           H  
HETATM   65  H37 UNL     1      -6.611  -0.118   2.035  1.00  0.00           H  
HETATM   66  H38 UNL     1      -8.563   1.911  -1.037  1.00  0.00           H  
HETATM   67  H39 UNL     1      -9.218   0.377  -0.238  1.00  0.00           H  
HETATM   68  H40 UNL     1      -7.864   0.353  -1.445  1.00  0.00           H  
HETATM   69  H41 UNL     1      -8.633   2.630   0.964  1.00  0.00           H  
HETATM   70  H42 UNL     1      -7.078   2.630   1.883  1.00  0.00           H  
HETATM   71  H43 UNL     1      -7.100   3.161   0.147  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3   32   33
CONECT    3    4   34   35
CONECT    4    5   36   37
CONECT    5    6   38   39
CONECT    6    7   40   41
CONECT    7    8    8   42
CONECT    8    9   43
CONECT    9   10   44   45
CONECT   10   11   46   47
CONECT   11   12   48   49
CONECT   12   13   50   51
CONECT   13   14   52   53
CONECT   14   15   54   55
CONECT   15   16   56   57
CONECT   16   17   17   18
CONECT   18   19
CONECT   19   20   24   58
CONECT   20   21   59   60
CONECT   21   22   22   23
CONECT   24   25   61   62
CONECT   25   26   27   28
CONECT   26   63   64   65
CONECT   27   66   67   68
CONECT   28   69   70   71
END

HMDB0013207
     RDKit          3D
9-Hexadecenoylcarnitine
 71 70  0  0  0  0  0  0  0  0999 V2000
   10.3224    0.3413    1.0832 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1204    0.8116    1.8632 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0175    1.2894    0.9369 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5850    0.1742    0.0377 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4957    0.6244   -0.8827 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2452    1.0964   -0.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6825    0.0316    0.6973 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4618   -0.4312    0.5496 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5055    0.0665   -0.4661 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0978   -1.0476   -1.4198 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4225   -2.1915   -0.8113 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1076   -2.1103   -0.1585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0203   -1.7715   -1.0347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1764   -0.4625   -1.6683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4205    0.6441   -0.6497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7102    0.2623    0.0505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6187   -0.0747    1.2509 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9059    0.3026   -0.6562 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0940   -0.0818    0.1310 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4563   -1.4152   -0.5152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5793   -2.1303    0.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6826   -2.1966   -0.5601 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4889   -2.7997    1.2435 O   0  0  0  0  0  1  0  0  0  0  0  0
   -6.0413    1.0195   -0.1534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3064    1.0757    0.4602 N   0  0  0  0  0  4  0  0  0  0  0  0
   -7.5527    0.2676    1.6002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3387    0.9127   -0.5853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5400    2.4842    0.9076 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1618   -0.7049    0.6908 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4406    0.9620    0.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2573    0.4101    1.6650 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7195   -0.0083    2.4755 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4412    1.6923    2.4798 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2098    1.6491    1.5758 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3746    2.1117    0.2704 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3306   -0.7527    0.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4543   -0.0911   -0.6047 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2052   -0.1060   -1.6368 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8611    1.5282   -1.4230 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5293    1.9945    0.5014 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5839    1.5036   -0.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2950   -0.4390    1.5094 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1324   -1.2480    1.2357 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5789    0.3250    0.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7735    0.9831   -0.9826 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7006   -0.6341   -2.3551 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1317   -1.4479   -1.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3951   -3.0681   -1.5648 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1678   -2.6400   -0.0522 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1238   -1.4782    0.7780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1198   -3.1540    0.2551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9714   -1.9447   -0.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1271   -2.6012   -1.8182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1872   -0.5101   -2.2312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4860   -0.1566   -2.4517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6221    0.6297    0.0818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5138    1.6279   -1.1477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7821   -0.2611    1.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5600   -2.1101   -0.4630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5303   -1.2182   -1.6301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5385    2.0365    0.0042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1798    1.0404   -1.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9587    0.9340    2.4296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3575   -0.4895    1.4898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6109   -0.1179    2.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5631    1.9113   -1.0368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2176    0.3768   -0.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8640    0.3528   -1.4447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6327    2.6302    0.9644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0776    2.6298    1.8829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0997    3.1614    0.1472 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  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 19 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 25 28  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  0
  8 43  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  0
 10 47  1  0
 11 48  1  0
 11 49  1  0
 12 50  1  0
 12 51  1  0
 13 52  1  0
 13 53  1  0
 14 54  1  0
 14 55  1  0
 15 56  1  0
 15 57  1  0
 19 58  1  1
 20 59  1  0
 20 60  1  0
 24 61  1  0
 24 62  1  0
 26 63  1  0
 26 64  1  0
 26 65  1  0
 27 66  1  0
 27 67  1  0
 27 68  1  0
 28 69  1  0
 28 70  1  0
 28 71  1  0
M  CHG  2  23  -1  25   1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3R)-3-[(9Z)-Hexadec-9-enoyloxy]-4-(trimethylazaniumyl)butanoic acid	HMDB
Palmitoleoylcarnitine	HMDB
9-Hexadecenoylcarnitine	HMDB

Chemical Formula

C₂₃H₄₃NO₄

Average Molecular Weight

397.6

Monoisotopic Molecular Weight

397.319208869

IUPAC Name

(3R)-3-[(9Z)-hexadec-9-enoyloxy]-4-(trimethylazaniumyl)butanoate

Traditional Name

(3R)-3-[(9Z)-hexadec-9-enoyloxy]-4-(trimethylammonio)butanoate

CAS Registry Number

329321-94-0

SMILES

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

InChI Identifier

InChI=1S/C23H43NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(27)28-21(19-22(25)26)20-24(2,3)4/h10-11,21H,5-9,12-20H2,1-4H3/b11-10-/t21-/m1/s1

InChI Key

JFAGPSOZZSTLRF-KUFMOJEASA-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

Not Available

Ontology

Physiological effect

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21359215)

Organ

Placenta (HMDB: HMDB0013207)

Excreta

Biofluid or Excreta

Feces (PMID: 27624970)
Urine (PMID: 32340350)

Cellular substructure

Organelle

Peroxisome (PMID: 35710135)

Cell

All cells and tissues (PMID: 35710135)

Source

Exogenous

Exogenous (HMDB: HMDB0013207)

Endogenous

Endogenous (HMDB: HMDB0013207)

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	9.9e-06 g/L	ALOGPS
logP	1.03	ALOGPS
logP	1.67	ChemAxon
logS	-7.7	ALOGPS
pKa (Strongest Acidic)	4.22	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	66.43 Å²	ChemAxon
Rotatable Bond Count	19	ChemAxon
Refractivity	138.19 m³·mol⁻¹	ChemAxon
Polarizability	48.83 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]+	208.751	30932474
DeepCCS	[M-H]-	205.301	30932474
DeepCCS	[M-2H]-	241.273	30932474
DeepCCS	[M+Na]+	217.566	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
9-Hexadecenoylcarnitine	CCCCCC\C=C/CCCCCCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C	3018.0	Standard polar	33892256
9-Hexadecenoylcarnitine	CCCCCC\C=C/CCCCCCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C	2419.9	Standard non polar	33892256
9-Hexadecenoylcarnitine	CCCCCC\C=C/CCCCCCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C	2682.1	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 - 9-Hexadecenoylcarnitine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Hexadecenoylcarnitine 10V, Positive-QTOF	splash10-0002-0009000000-78c0db1f7d539241ca80	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Hexadecenoylcarnitine 20V, Positive-QTOF	splash10-000j-9005000000-9978022cc1181ffa3452	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Hexadecenoylcarnitine 40V, Positive-QTOF	splash10-000i-9000000000-e9262cbaff8cb4ad0ba6	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.03 +/- 0.01 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	0.010-0.060 uM	Adult (>18 years old)	Both	Normal	Molecular You	details
Blood	Detected and Quantified	0.03 +/- 0.01 uM	Children (1-13 years old)	Both	Normal	23108202	details
Blood	Detected and Quantified	<0.08 uM	Adolescent (13-18 years old)	Male	Normal	24453145	details
Feces	Detected and Quantified	0.29 +/- 0.16 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Feces	Detected and Quantified	0.25 +/- 0.11 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Urine	Detected and Quantified	0.03 (0.02-0.05) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	Analysis of 40 NI...	details
Urine	Detected and Quantified	0.0-0.03 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	32340350	details
Urine	Detected and Quantified	0.01 +/- 0.01 umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	32340350	details
Urine	Detected and Quantified	0.01 +/- 0.0 umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	32340350	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.04 +/- 0.01 uM	Children (1-13 years old)	Both	Obese	24740590	details
Blood	Detected and Quantified	0.04 +/- 0.01 uM	Children (1-13 years old)	Both	Obese	24740590	details
Blood	Detected and Quantified	0.04 +/- 0.01 uM	Children (1-13 years old)	Both	Obese	24740590	details
Blood	Detected and Quantified	0.041 +/- 0.012 uM	Children (1-13 years old)	Both	Obesity	Metabolomics reve...	details
Blood	Detected and Quantified	0.044 +/- 0.013 uM	Children (1-13 years old)	Both	Obesity	Metabolomics reve...	details
Blood	Detected and Quantified	0.04 +/- 0.01 uM	Children (1-13 years old)	Both	Obese	23108202	details
Blood	Detected and Quantified	0.33 uM	Adolescent (13-18 years old)	Male	Glutaric aciduria II	24453145	details
Blood	Detected and Quantified	0.9 uM	Adolescent (13-18 years old)	Male	Glutaric aciduria II	24453145	details

Associated Disorders and Diseases

Disease References

Glutaric aciduria II
Prasad M, Hussain S: Glutaric aciduria type II presenting as myopathy and rhabdomyolysis in a teenager. J Child Neurol. 2015 Jan;30(1):96-9. doi: 10.1177/0883073813516676. Epub 2014 Jan 21. [PubMed:24453145 ]
Obesity
Reinehr T, Wolters B, Knop C, Lass N, Hellmuth C, Harder U, Peissner W, Wahl S, Grallert H, Adamski J, Illig T, Prehn C, Yu Z, Wang-Sattler R, Koletzko B: Changes in the serum metabolite profile in obese children with weight loss. Eur J Nutr. 2015 Mar;54(2):173-81. doi: 10.1007/s00394-014-0698-8. Epub 2014 Apr 17. [PubMed:24740590 ] Wahl S, Yu Z, Kleber M, Singmann P, Holzapfel C, He Y, Mittelstrass K, Polonikov A, Prehn C, Romisch-Margl W, Adamski J, Suhre K, Grallert H, Illig T, Wang-Sattler R, Reinehr T: Childhood obesity is associated with changes in the serum metabolite profile. Obes Facts. 2012;5(5):660-70. doi: 10.1159/000343204. Epub 2012 Oct 4. [PubMed:23108202 ] Simone Wahl, Christina Holzapfel, Zhonghao Yu, Michaela Breier, Ivan Kondofersky, Christiane Fuchs, Paula Singmann, Cornelia Prehn, Jerzy Adamski, Harald Grallert, Thomas Illig, Rui Wang-Sattler, Thomas Reinehr (2013). Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children. Metabolomics.

Associated OMIM IDs

231680 (Glutaric aciduria II)
601665 (Obesity)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

107447736

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

156908005

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

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Showing metabocard for 9-Hexadecenoylcarnitine (HMDB0013207)

MOL for HMDB0013207 (9-Hexadecenoylcarnitine)

3D MOL for HMDB0013207 (9-Hexadecenoylcarnitine)

3D SDF for HMDB0013207 (9-Hexadecenoylcarnitine)

3D-SDF for HMDB0013207 (9-Hexadecenoylcarnitine)

PDB for HMDB0013207 (9-Hexadecenoylcarnitine)

3D PDB for HMDB0013207 (9-Hexadecenoylcarnitine)

SMILES for HMDB0013207 (9-Hexadecenoylcarnitine)

INCHI for HMDB0013207 (9-Hexadecenoylcarnitine)

Structure for HMDB0013207 (9-Hexadecenoylcarnitine)

3D Structure for HMDB0013207 (9-Hexadecenoylcarnitine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra