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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2010-02-22 12:02:22 UTC

Update Date

2022-10-24 19:44:13 UTC

HMDB ID

HMDB0013336

Secondary Accession Numbers

HMDB13336

Metabolite Identification

Common Name

3-Hydroxyhexadecanoylcarnitine

Description

3-Hydroxyhexadecanoylcarnitine is an acylcarnitine. More specifically, it is an 3-hydroxyhexadecanoic acid ester of carnitine. Acylcarnitines were first discovered more than 70 year ago (PMID: 13825279 ). It is believed that there are more than 1000 types of acylcarnitines in the human body. The general role of acylcarnitines is to transport acyl-groups (organic acids and fatty acids) from the cytoplasm into the mitochondria so that they can be broken down to produce energy. This process is known as beta-oxidation. According to a recent review (PMID: 35710135 ), acylcarnitines (ACs) can be classified into 9 different categories depending on the type and size of their acyl-group: 1) short-chain ACs; 2) medium-chain ACs; 3) long-chain ACs; 4) very long-chain ACs; 5) hydroxy ACs; 6) branched chain ACs; 7) unsaturated ACs; 8) dicarboxylic ACs and 9) miscellaneous ACs. Short-chain ACs have acyl-groups with two to five carbons (C2-C5), medium-chain ACs have acyl-groups with six to thirteen carbons (C6-C13), long-chain ACs have acyl-groups with fourteen to twenty once carbons (C14-C21) and very long-chain ACs have acyl groups with more than 22 carbons. 3-Hydroxyhexadecanoylcarnitine is therefore classified as a long chain AC. As a long-chain acylcarnitine 3-hydroxyhexadecanoylcarnitine 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 3-hydroxyhexadecanoylcarnitine is elevated in the blood or plasma of individuals with type 2 diabetes mellitus (PMID: 24358186 , PMID: 32708684 , PMID: 24837145 ), long-chain 3-hydroxy acyl CoA dehydrogenase deficiency (PMID: 25888220 ), and mitochondrial trifunctional protein deficiency (PMID: 19880769 ). It is also decreased in the blood or plasma of individuals with psoriasis (PMID: 33391503 ). 3-Hydroxyhexadecanoylcarnitine can be found in urine and faces as well. 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

      
  Mrv1652301312018062D          

 29 28  0  0  0  0            999 V2000
10003.995910007.9523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.281610008.3657    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10003.281610009.1905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.567210009.6011    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
10001.848810009.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.567210010.4264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.713710010.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.575510007.9420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.575510007.1174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.289610006.7038    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
10001.861110006.7038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.710210008.3657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.424510007.9523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.138810008.3657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.852910007.9523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.567310008.3657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.281610007.9523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.995310008.3657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.711310007.9523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.425210008.3657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.141110007.9523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.854910008.3657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.568810007.9523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.282710008.3657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.998610007.9523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.712610008.3657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10015.426510007.9523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.138810009.1905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.710210009.1905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 12  1  0  0  0  0
  2  3  1  6  0  0  0
  2  8  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 12 13  1  0  0  0  0
 12 29  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 28  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
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  CHG  2   4   1  10  -1
M  END

HMDB0013336
     RDKit          3D
3-Hydroxyhexadecanoylcarnitine
 74 73  0  0  0  0  0  0  0  0999 V2000
    7.6505   -1.1082    0.6872 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3008   -2.3916    0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8972   -2.7718   -0.1397 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1191   -1.9142   -1.0699 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0057   -0.5085   -0.6481 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1395    0.2608   -1.6641 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7807   -0.3459   -1.7276 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0482   -0.3383   -0.4214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8953    1.1106    0.0357 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1385    1.0377    1.3509 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9433    2.4032    1.9113 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1799    3.2811    1.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1905    2.9748    0.6363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2291    2.9166    1.6882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4697    2.7274    0.9301 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2014    1.6521    2.5231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4384    0.4321    1.7206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1212   -0.6904    2.2133 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9883    0.5061    0.4721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1814   -0.7295   -0.2597 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2515   -0.6694   -1.4639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3086   -1.8728   -2.2823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9859   -2.8588   -1.9492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5804   -1.9348   -3.4876 O   0  0  0  0  0  1  0  0  0  0  0  0
   -4.6013   -0.7554   -0.7144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5974   -0.7495    0.3211 N   0  0  0  0  0  4  0  0  0  0  0  0
   -6.8536   -1.2445   -0.2707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3212   -1.6048    1.4333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8520    0.5797    0.7875 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5283   -1.3391    1.4044 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8345   -0.6767    1.2621 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0912   -0.3285    0.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7712   -3.2321    0.6706 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7950   -2.4460   -0.9691 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9107   -3.8557   -0.5020 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3431   -2.8983    0.8513 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5352   -1.9406   -2.1151 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1183   -2.4200   -1.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6869   -0.2958    0.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0147   -0.0229   -0.7986 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1547    1.3279   -1.4216 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6347    0.1204   -2.6416 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1708    0.3269   -2.4113 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8072   -1.3106   -2.2394 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5865   -0.8539    0.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0812   -0.8314   -0.5418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8810    1.5643    0.2529 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4008    1.7020   -0.7338 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2513    0.4547    1.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8035    0.4543    2.0344 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0150    2.8508    2.0132 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6447    2.3420    2.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7932    3.4682    0.0513 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2607    4.3495    1.4639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4796    3.7464   -0.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1644    2.0040    0.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4017    3.8151    2.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0943    3.4387    1.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1225    1.6997    3.2119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3661    1.5315    3.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8541   -1.5809    0.3397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2184   -0.4888   -1.0924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5310    0.2497   -2.0322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7589   -1.6232   -1.3837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7656    0.1487   -1.3865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7055   -0.6846    0.1514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9669   -2.3205   -0.0523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8085   -1.0982   -1.3515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7929   -2.5506    1.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3141   -1.9724    1.8338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8250   -1.0778    2.2662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9418    0.7073    1.0669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6267    1.3112    0.0098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3035    0.8416    1.7043 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  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 20 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 26 29  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  6 42  1  0
  7 43  1  0
  7 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  0
  9 48  1  0
 10 49  1  0
 10 50  1  0
 11 51  1  0
 11 52  1  0
 12 53  1  0
 12 54  1  0
 13 55  1  0
 13 56  1  0
 14 57  1  0
 15 58  1  0
 16 59  1  0
 16 60  1  0
 20 61  1  1
 21 62  1  0
 21 63  1  0
 25 64  1  0
 25 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
 29 72  1  0
 29 73  1  0
 29 74  1  0
M  CHG  2  24  -1  26   1
M  END

      
  Mrv1652301312018062D          

 29 28  0  0  0  0            999 V2000
10003.995910007.9523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.281610008.3657    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10003.281610009.1905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.567210009.6011    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
10001.848810009.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.567210010.4264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.713710010.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.575510007.9420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.575510007.1174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.289610006.7038    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
10001.861110006.7038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.710210008.3657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.424510007.9523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.138810008.3657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.852910007.9523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.567310008.3657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.281610007.9523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.995310008.3657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.711310007.9523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.425210008.3657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.141110007.9523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.854910008.3657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.568810007.9523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.282710008.3657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.998610007.9523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.712610008.3657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10015.426510007.9523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.138810009.1905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.710210009.1905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 12  1  0  0  0  0
  2  3  1  6  0  0  0
  2  8  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 12 13  1  0  0  0  0
 12 29  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 28  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
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  CHG  2   4   1  10  -1
M  END
> <DATABASE_ID>
HMDB0013336

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCCCCCCCC(O)CC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C23H45NO5/c1-5-6-7-8-9-10-11-12-13-14-15-16-20(25)17-23(28)29-21(18-22(26)27)19-24(2,3)4/h20-21,25H,5-19H2,1-4H3/t20?,21-/m1/s1

> <INCHI_KEY>
XKAZIAFZAQAHHG-BPGUCPLFSA-N

> <FORMULA>
C23H45NO5

> <MOLECULAR_WEIGHT>
415.615

> <EXACT_MASS>
415.329773553

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
50.99136136133673

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R)-3-[(3-hydroxyhexadecanoyl)oxy]-4-(trimethylazaniumyl)butanoate

> <ALOGPS_LOGP>
0.35

> <JCHEM_LOGP>
0.8027367871949209

> <ALOGPS_LOGS>
-6.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.000091801572765

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.102434316471337

> <JCHEM_PKA_STRONGEST_BASIC>
-2.798760130283852

> <JCHEM_POLAR_SURFACE_AREA>
86.66

> <JCHEM_REFRACTIVITY>
138.59220000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
20

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.46e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-3-[(3-hydroxyhexadecanoyl)oxy]-4-(trimethylammonio)butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013336
     RDKit          3D
3-Hydroxyhexadecanoylcarnitine
 74 73  0  0  0  0  0  0  0  0999 V2000
    7.6505   -1.1082    0.6872 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3008   -2.3916    0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8972   -2.7718   -0.1397 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1191   -1.9142   -1.0699 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0057   -0.5085   -0.6481 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1395    0.2608   -1.6641 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7807   -0.3459   -1.7276 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0482   -0.3383   -0.4214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8953    1.1106    0.0357 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1385    1.0377    1.3509 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9433    2.4032    1.9113 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1799    3.2811    1.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1905    2.9748    0.6363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2291    2.9166    1.6882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4697    2.7274    0.9301 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2014    1.6521    2.5231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4384    0.4321    1.7206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1212   -0.6904    2.2133 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9883    0.5061    0.4721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1814   -0.7295   -0.2597 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2515   -0.6694   -1.4639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3086   -1.8728   -2.2823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9859   -2.8588   -1.9492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5804   -1.9348   -3.4876 O   0  0  0  0  0  1  0  0  0  0  0  0
   -4.6013   -0.7554   -0.7144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5974   -0.7495    0.3211 N   0  0  0  0  0  4  0  0  0  0  0  0
   -6.8536   -1.2445   -0.2707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3212   -1.6048    1.4333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8520    0.5797    0.7875 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5283   -1.3391    1.4044 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8345   -0.6767    1.2621 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0912   -0.3285    0.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7712   -3.2321    0.6706 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7950   -2.4460   -0.9691 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9107   -3.8557   -0.5020 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3431   -2.8983    0.8513 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5352   -1.9406   -2.1151 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1183   -2.4200   -1.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6869   -0.2958    0.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0147   -0.0229   -0.7986 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1547    1.3279   -1.4216 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6347    0.1204   -2.6416 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1708    0.3269   -2.4113 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8072   -1.3106   -2.2394 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5865   -0.8539    0.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0812   -0.8314   -0.5418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8810    1.5643    0.2529 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4008    1.7020   -0.7338 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2513    0.4547    1.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8035    0.4543    2.0344 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0150    2.8508    2.0132 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6447    2.3420    2.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7932    3.4682    0.0513 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2607    4.3495    1.4639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4796    3.7464   -0.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1644    2.0040    0.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4017    3.8151    2.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0943    3.4387    1.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1225    1.6997    3.2119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3661    1.5315    3.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8541   -1.5809    0.3397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2184   -0.4888   -1.0924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5310    0.2497   -2.0322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7589   -1.6232   -1.3837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7656    0.1487   -1.3865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7055   -0.6846    0.1514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9669   -2.3205   -0.0523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8085   -1.0982   -1.3515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7929   -2.5506    1.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3141   -1.9724    1.8338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8250   -1.0778    2.2662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9418    0.7073    1.0669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6267    1.3112    0.0098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3035    0.8416    1.7043 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  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 20 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 26 29  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  6 42  1  0
  7 43  1  0
  7 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  0
  9 48  1  0
 10 49  1  0
 10 50  1  0
 11 51  1  0
 11 52  1  0
 12 53  1  0
 12 54  1  0
 13 55  1  0
 13 56  1  0
 14 57  1  0
 15 58  1  0
 16 59  1  0
 16 60  1  0
 20 61  1  1
 21 62  1  0
 21 63  1  0
 25 64  1  0
 25 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
 29 72  1  0
 29 73  1  0
 29 74  1  0
M  CHG  2  24  -1  26   1
M  END

HEADER    PROTEIN                                 31-JAN-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-JAN-20         0                                  
HETATM    1  O   UNK     0    8674.1268681.511   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8672.7928682.283   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8672.7928683.822   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0    8671.4598684.589   0.000  0.00  0.00           N+1
HETATM    5  C   UNK     0    8670.1188683.818   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8671.4598686.129   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8669.8668685.509   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8671.4748681.492   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8671.4748679.952   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8672.8078679.180   0.000  0.00  0.00           O-1
HETATM   11  O   UNK     0    8670.1418679.180   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8675.4598682.283   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8676.7928681.511   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8678.1268682.283   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8679.4598681.511   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8680.7928682.283   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8682.1268681.511   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8683.4588682.283   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8684.7948681.511   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8686.1278682.283   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8687.4638681.511   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8688.7968682.283   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8690.1288681.511   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8691.4618682.283   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8692.7978681.511   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8694.1308682.283   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8695.4638681.511   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0    8678.1268683.822   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0    8675.4598683.822   0.000  0.00  0.00           O+0
CONECT    1    2   12                                                       
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6    7                                             
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    4                                                            
CONECT    8    2    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    1   13   29                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   28                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   14                                                            
CONECT   29   12                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   56    0
END

COMPND    HMDB0013336
HETATM    1  C1  UNL     1       7.650  -1.108   0.687  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.301  -2.392   0.057  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.897  -2.772  -0.140  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.119  -1.914  -1.070  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.006  -0.509  -0.648  1.00  0.00           C  
HETATM    6  C6  UNL     1       4.139   0.261  -1.664  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.781  -0.346  -1.728  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.048  -0.338  -0.421  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.895   1.111   0.036  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.138   1.038   1.351  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.943   2.403   1.911  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.180   3.281   1.021  1.00  0.00           C  
HETATM   13  C13 UNL     1      -1.190   2.975   0.636  1.00  0.00           C  
HETATM   14  C14 UNL     1      -2.229   2.917   1.688  1.00  0.00           C  
HETATM   15  O1  UNL     1      -3.470   2.727   0.930  1.00  0.00           O  
HETATM   16  C15 UNL     1      -2.201   1.652   2.523  1.00  0.00           C  
HETATM   17  C16 UNL     1      -2.438   0.432   1.721  1.00  0.00           C  
HETATM   18  O2  UNL     1      -2.121  -0.690   2.213  1.00  0.00           O  
HETATM   19  O3  UNL     1      -2.988   0.506   0.472  1.00  0.00           O  
HETATM   20  C17 UNL     1      -3.181  -0.730  -0.260  1.00  0.00           C  
HETATM   21  C18 UNL     1      -2.251  -0.669  -1.464  1.00  0.00           C  
HETATM   22  C19 UNL     1      -2.309  -1.873  -2.282  1.00  0.00           C  
HETATM   23  O4  UNL     1      -2.986  -2.859  -1.949  1.00  0.00           O  
HETATM   24  O5  UNL     1      -1.580  -1.935  -3.488  1.00  0.00           O1-
HETATM   25  C20 UNL     1      -4.601  -0.755  -0.714  1.00  0.00           C  
HETATM   26  N1  UNL     1      -5.597  -0.749   0.321  1.00  0.00           N1+
HETATM   27  C21 UNL     1      -6.854  -1.245  -0.271  1.00  0.00           C  
HETATM   28  C22 UNL     1      -5.321  -1.605   1.433  1.00  0.00           C  
HETATM   29  C23 UNL     1      -5.852   0.580   0.788  1.00  0.00           C  
HETATM   30  H1  UNL     1       8.528  -1.339   1.404  1.00  0.00           H  
HETATM   31  H2  UNL     1       6.835  -0.677   1.262  1.00  0.00           H  
HETATM   32  H3  UNL     1       8.091  -0.328   0.032  1.00  0.00           H  
HETATM   33  H4  UNL     1       7.771  -3.232   0.671  1.00  0.00           H  
HETATM   34  H5  UNL     1       7.795  -2.446  -0.969  1.00  0.00           H  
HETATM   35  H6  UNL     1       5.911  -3.856  -0.502  1.00  0.00           H  
HETATM   36  H7  UNL     1       5.343  -2.898   0.851  1.00  0.00           H  
HETATM   37  H8  UNL     1       5.535  -1.941  -2.115  1.00  0.00           H  
HETATM   38  H9  UNL     1       4.118  -2.420  -1.194  1.00  0.00           H  
HETATM   39  H10 UNL     1       4.687  -0.296   0.365  1.00  0.00           H  
HETATM   40  H11 UNL     1       6.015  -0.023  -0.799  1.00  0.00           H  
HETATM   41  H12 UNL     1       4.155   1.328  -1.422  1.00  0.00           H  
HETATM   42  H13 UNL     1       4.635   0.120  -2.642  1.00  0.00           H  
HETATM   43  H14 UNL     1       2.171   0.327  -2.411  1.00  0.00           H  
HETATM   44  H15 UNL     1       2.807  -1.311  -2.239  1.00  0.00           H  
HETATM   45  H16 UNL     1       2.587  -0.854   0.389  1.00  0.00           H  
HETATM   46  H17 UNL     1       1.081  -0.831  -0.542  1.00  0.00           H  
HETATM   47  H18 UNL     1       2.881   1.564   0.253  1.00  0.00           H  
HETATM   48  H19 UNL     1       1.401   1.702  -0.734  1.00  0.00           H  
HETATM   49  H20 UNL     1       0.251   0.455   1.166  1.00  0.00           H  
HETATM   50  H21 UNL     1       1.804   0.454   2.034  1.00  0.00           H  
HETATM   51  H22 UNL     1       2.015   2.851   2.013  1.00  0.00           H  
HETATM   52  H23 UNL     1       0.645   2.342   2.964  1.00  0.00           H  
HETATM   53  H24 UNL     1       0.793   3.468   0.051  1.00  0.00           H  
HETATM   54  H25 UNL     1       0.261   4.349   1.464  1.00  0.00           H  
HETATM   55  H26 UNL     1      -1.480   3.746  -0.168  1.00  0.00           H  
HETATM   56  H27 UNL     1      -1.164   2.004   0.037  1.00  0.00           H  
HETATM   57  H28 UNL     1      -2.402   3.815   2.270  1.00  0.00           H  
HETATM   58  H29 UNL     1      -4.094   3.439   1.142  1.00  0.00           H  
HETATM   59  H30 UNL     1      -3.123   1.700   3.212  1.00  0.00           H  
HETATM   60  H31 UNL     1      -1.366   1.531   3.192  1.00  0.00           H  
HETATM   61  H32 UNL     1      -2.854  -1.581   0.340  1.00  0.00           H  
HETATM   62  H33 UNL     1      -1.218  -0.489  -1.092  1.00  0.00           H  
HETATM   63  H34 UNL     1      -2.531   0.250  -2.032  1.00  0.00           H  
HETATM   64  H35 UNL     1      -4.759  -1.623  -1.384  1.00  0.00           H  
HETATM   65  H36 UNL     1      -4.766   0.149  -1.386  1.00  0.00           H  
HETATM   66  H37 UNL     1      -7.706  -0.685   0.151  1.00  0.00           H  
HETATM   67  H38 UNL     1      -6.967  -2.320  -0.052  1.00  0.00           H  
HETATM   68  H39 UNL     1      -6.809  -1.098  -1.352  1.00  0.00           H  
HETATM   69  H40 UNL     1      -4.793  -2.551   1.145  1.00  0.00           H  
HETATM   70  H41 UNL     1      -6.314  -1.972   1.834  1.00  0.00           H  
HETATM   71  H42 UNL     1      -4.825  -1.078   2.266  1.00  0.00           H  
HETATM   72  H43 UNL     1      -6.942   0.707   1.067  1.00  0.00           H  
HETATM   73  H44 UNL     1      -5.627   1.311   0.010  1.00  0.00           H  
HETATM   74  H45 UNL     1      -5.303   0.842   1.704  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3   33   34
CONECT    3    4   35   36
CONECT    4    5   37   38
CONECT    5    6   39   40
CONECT    6    7   41   42
CONECT    7    8   43   44
CONECT    8    9   45   46
CONECT    9   10   47   48
CONECT   10   11   49   50
CONECT   11   12   51   52
CONECT   12   13   53   54
CONECT   13   14   55   56
CONECT   14   15   16   57
CONECT   15   58
CONECT   16   17   59   60
CONECT   17   18   18   19
CONECT   19   20
CONECT   20   21   25   61
CONECT   21   22   62   63
CONECT   22   23   23   24
CONECT   25   26   64   65
CONECT   26   27   28   29
CONECT   27   66   67   68
CONECT   28   69   70   71
CONECT   29   72   73   74
END

HMDB0013336
     RDKit          3D
3-Hydroxyhexadecanoylcarnitine
 74 73  0  0  0  0  0  0  0  0999 V2000
    7.6505   -1.1082    0.6872 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3008   -2.3916    0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8972   -2.7718   -0.1397 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1191   -1.9142   -1.0699 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0057   -0.5085   -0.6481 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1395    0.2608   -1.6641 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7807   -0.3459   -1.7276 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0482   -0.3383   -0.4214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8953    1.1106    0.0357 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1385    1.0377    1.3509 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9433    2.4032    1.9113 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1799    3.2811    1.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1905    2.9748    0.6363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2291    2.9166    1.6882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4697    2.7274    0.9301 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2014    1.6521    2.5231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4384    0.4321    1.7206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1212   -0.6904    2.2133 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9883    0.5061    0.4721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1814   -0.7295   -0.2597 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2515   -0.6694   -1.4639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3086   -1.8728   -2.2823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9859   -2.8588   -1.9492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5804   -1.9348   -3.4876 O   0  0  0  0  0  1  0  0  0  0  0  0
   -4.6013   -0.7554   -0.7144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5974   -0.7495    0.3211 N   0  0  0  0  0  4  0  0  0  0  0  0
   -6.8536   -1.2445   -0.2707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3212   -1.6048    1.4333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8520    0.5797    0.7875 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5283   -1.3391    1.4044 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8345   -0.6767    1.2621 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0912   -0.3285    0.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7712   -3.2321    0.6706 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7950   -2.4460   -0.9691 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9107   -3.8557   -0.5020 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3431   -2.8983    0.8513 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5352   -1.9406   -2.1151 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1183   -2.4200   -1.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6869   -0.2958    0.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0147   -0.0229   -0.7986 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1547    1.3279   -1.4216 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6347    0.1204   -2.6416 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1708    0.3269   -2.4113 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8072   -1.3106   -2.2394 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5865   -0.8539    0.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0812   -0.8314   -0.5418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8810    1.5643    0.2529 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4008    1.7020   -0.7338 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2513    0.4547    1.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8035    0.4543    2.0344 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0150    2.8508    2.0132 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6447    2.3420    2.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7932    3.4682    0.0513 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2607    4.3495    1.4639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4796    3.7464   -0.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1644    2.0040    0.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4017    3.8151    2.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0943    3.4387    1.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1225    1.6997    3.2119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3661    1.5315    3.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8541   -1.5809    0.3397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2184   -0.4888   -1.0924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5310    0.2497   -2.0322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7589   -1.6232   -1.3837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7656    0.1487   -1.3865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7055   -0.6846    0.1514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9669   -2.3205   -0.0523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8085   -1.0982   -1.3515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7929   -2.5506    1.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3141   -1.9724    1.8338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8250   -1.0778    2.2662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9418    0.7073    1.0669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6267    1.3112    0.0098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3035    0.8416    1.7043 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  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 20 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 26 29  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  6 42  1  0
  7 43  1  0
  7 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  0
  9 48  1  0
 10 49  1  0
 10 50  1  0
 11 51  1  0
 11 52  1  0
 12 53  1  0
 12 54  1  0
 13 55  1  0
 13 56  1  0
 14 57  1  0
 15 58  1  0
 16 59  1  0
 16 60  1  0
 20 61  1  1
 21 62  1  0
 21 63  1  0
 25 64  1  0
 25 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
 29 72  1  0
 29 73  1  0
 29 74  1  0
M  CHG  2  24  -1  26   1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Hydroxypalmitoylcarnitine	HMDB
(3R)-3-[(3-Hydroxyhexadecanoyl)oxy]-4-(trimethylazaniumyl)butanoic acid	HMDB
3-Hydroxyhexadecanoylcarnitine	HMDB

Chemical Formula

C₂₃H₄₅NO₅

Average Molecular Weight

415.615

Monoisotopic Molecular Weight

415.329773553

IUPAC Name

(3R)-3-[(3-hydroxyhexadecanoyl)oxy]-4-(trimethylazaniumyl)butanoate

Traditional Name

(3R)-3-[(3-hydroxyhexadecanoyl)oxy]-4-(trimethylammonio)butanoate

CAS Registry Number

195207-76-2

SMILES

CCCCCCCCCCCCCC(O)CC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C

InChI Identifier

InChI=1S/C23H45NO5/c1-5-6-7-8-9-10-11-12-13-14-15-16-20(25)17-23(28)29-21(18-22(26)27)19-24(2,3)4/h20-21,25H,5-19H2,1-4H3/t20?,21-/m1/s1

InChI Key

XKAZIAFZAQAHHG-BPGUCPLFSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Acyl carnitines

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Not Available

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	8.9e-05 g/L	ALOGPS
logP	0.35	ALOGPS
logP	0.8	ChemAxon
logS	-6.7	ALOGPS
pKa (Strongest Acidic)	4.1	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	86.66 Å²	ChemAxon
Rotatable Bond Count	20	ChemAxon
Refractivity	138.59 m³·mol⁻¹	ChemAxon
Polarizability	50.99 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]+	206.948	30932474
DeepCCS	[M-H]-	203.503	30932474
DeepCCS	[M-2H]-	239.346	30932474
DeepCCS	[M+Na]+	215.578	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	8.56 minutes	32390414
Predicted by Siyang on May 30, 2022	16.1819 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.23 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	75.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2524.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	181.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	232.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	168.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	387.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	735.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	683.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	627.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1815.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	532.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	2039.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	375.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	457.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	241.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	74.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxyhexadecanoylcarnitine	CCCCCCCCCCCCCC(O)CC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C	3323.7	Standard polar	33892256
3-Hydroxyhexadecanoylcarnitine	CCCCCCCCCCCCCC(O)CC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C	2650.4	Standard non polar	33892256
3-Hydroxyhexadecanoylcarnitine	CCCCCCCCCCCCCC(O)CC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C	2873.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxyhexadecanoylcarnitine,1TMS,isomer #1	CCCCCCCCCCCCCC(CC(=O)O[C@H](CC(=O)[O-])C[N+](C)(C)C)O[Si](C)(C)C	2814.8	Semi standard non polar	33892256
3-Hydroxyhexadecanoylcarnitine,1TBDMS,isomer #1	CCCCCCCCCCCCCC(CC(=O)O[C@H](CC(=O)[O-])C[N+](C)(C)C)O[Si](C)(C)C(C)(C)C	3044.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxyhexadecanoylcarnitine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyhexadecanoylcarnitine 10V, Positive-QTOF	splash10-014i-0000900000-1eb100b2120916e48047	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyhexadecanoylcarnitine 20V, Positive-QTOF	splash10-00kr-9000500000-7fed585e2fa9417df9a7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyhexadecanoylcarnitine 40V, Positive-QTOF	splash10-000i-9000000000-e9262cbaff8cb4ad0ba6	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
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	0.0050-0.0200 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
Feces	Detected and Quantified	0.26 +/- 0.14 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Feces	Detected and Quantified	0.24 +/- 0.1 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Urine	Detected and Quantified	0.0015 (0.0006-0.0050) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029396

KNApSAcK ID

Not Available

Chemspider ID

48061760

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

126456228

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

3HEXDCRN

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Zhang X, Zhang C, Chen L, Han X, Ji L: Human serum acylcarnitine profiles in different glucose tolerance states. Diabetes Res Clin Pract. 2014 Jun;104(3):376-82. doi: 10.1016/j.diabres.2014.04.013. Epub 2014 Apr 28. [PubMed:24837145 ]
FRITZ IB: Action of carnitine on long chain fatty acid oxidation by liver. Am J Physiol. 1959 Aug;197:297-304. doi: 10.1152/ajplegacy.1959.197.2.297. [PubMed:13825279 ]
Reuter SE, Evans AM: Carnitine and acylcarnitines: pharmacokinetic, pharmacological and clinical aspects. Clin Pharmacokinet. 2012 Sep 1;51(9):553-72. doi: 10.1007/BF03261931. [PubMed:22804748 ]
Bruce CR, Hoy AJ, Turner N, Watt MJ, Allen TL, Carpenter K, Cooney GJ, Febbraio MA, Kraegen EW: Overexpression of carnitine palmitoyltransferase-1 in skeletal muscle is sufficient to enhance fatty acid oxidation and improve high-fat diet-induced insulin resistance. Diabetes. 2009 Mar;58(3):550-8. doi: 10.2337/db08-1078. Epub 2008 Dec 10. [PubMed:19073774 ]
Schooneman MG, Vaz FM, Houten SM, Soeters MR: Acylcarnitines: reflecting or inflicting insulin resistance? Diabetes. 2013 Jan;62(1):1-8. doi: 10.2337/db12-0466. [PubMed:23258903 ]
Ahmad T, Kelly JP, McGarrah RW, Hellkamp AS, Fiuzat M, Testani JM, Wang TS, Verma A, Samsky MD, Donahue MP, Ilkayeva OR, Bowles DE, Patel CB, Milano CA, Rogers JG, Felker GM, O'Connor CM, Shah SH, Kraus WE: Prognostic Implications of Long-Chain Acylcarnitines in Heart Failure and Reversibility With Mechanical Circulatory Support. J Am Coll Cardiol. 2016 Jan 26;67(3):291-9. doi: 10.1016/j.jacc.2015.10.079. [PubMed:26796394 ]
Mai M, Tonjes A, Kovacs P, Stumvoll M, Fiedler GM, Leichtle AB: Serum levels of acylcarnitines are altered in prediabetic conditions. PLoS One. 2013 Dec 16;8(12):e82459. doi: 10.1371/journal.pone.0082459. eCollection 2013. [PubMed:24358186 ]
Chen C, Hou G, Zeng C, Ren Y, Chen X, Peng C: Metabolomic profiling reveals amino acid and carnitine alterations as metabolic signatures in psoriasis. Theranostics. 2021 Jan 1;11(2):754-767. doi: 10.7150/thno.51154. eCollection 2021. [PubMed:33391503 ]
Park HD, Kim SR, Ki CS, Lee SY, Chang YS, Jin DK, Park WS: Two novel HADHB gene mutations in a Korean patient with mitochondrial trifunctional protein deficiency. Ann Clin Lab Sci. 2009 Fall;39(4):399-404. [PubMed:19880769 ]
Hameed A, Mojsak P, Buczynska A, Suleria HAR, Kretowski A, Ciborowski M: Altered Metabolome of Lipids and Amino Acids Species: A Source of Early Signature Biomarkers of T2DM. J Clin Med. 2020 Jul 16;9(7). pii: jcm9072257. doi: 10.3390/jcm9072257. [PubMed:32708684 ]
Karall D, Brunner-Krainz M, Kogelnig K, Konstantopoulou V, Maier EM, Moslinger D, Plecko B, Sperl W, Volkmar B, Scholl-Burgi S: Clinical outcome, biochemical and therapeutic follow-up in 14 Austrian patients with Long-Chain 3-Hydroxy Acyl CoA Dehydrogenase Deficiency (LCHADD). Orphanet J Rare Dis. 2015 Feb 22;10:21. doi: 10.1186/s13023-015-0236-7. [PubMed:25888220 ]
Dambrova M, Makrecka-Kuka M, Kuka J, Vilskersts R, Nordberg D, Attwood MM, Smesny S, Sen ZD, Guo AC, Oler E, Tian S, Zheng J, Wishart DS, Liepinsh E, Schioth HB: Acylcarnitines: Nomenclature, Biomarkers, Therapeutic Potential, Drug Targets, and Clinical Trials. Pharmacol Rev. 2022 Jul;74(3):506-551. doi: 10.1124/pharmrev.121.000408. [PubMed:35710135 ]

Showing metabocard for 3-Hydroxyhexadecanoylcarnitine (HMDB0013336)

MOL for HMDB0013336 (3-Hydroxyhexadecanoylcarnitine)

3D MOL for HMDB0013336 (3-Hydroxyhexadecanoylcarnitine)

3D SDF for HMDB0013336 (3-Hydroxyhexadecanoylcarnitine)

3D-SDF for HMDB0013336 (3-Hydroxyhexadecanoylcarnitine)

PDB for HMDB0013336 (3-Hydroxyhexadecanoylcarnitine)

3D PDB for HMDB0013336 (3-Hydroxyhexadecanoylcarnitine)

SMILES for HMDB0013336 (3-Hydroxyhexadecanoylcarnitine)

INCHI for HMDB0013336 (3-Hydroxyhexadecanoylcarnitine)

Structure for HMDB0013336 (3-Hydroxyhexadecanoylcarnitine)

3D Structure for HMDB0013336 (3-Hydroxyhexadecanoylcarnitine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra