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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2010-02-22 11:52:59 UTC

Update Date

2022-10-24 19:44:13 UTC

HMDB ID

HMDB0013335

Secondary Accession Numbers

HMDB13335

Metabolite Identification

Common Name

3-Hydroxyhexadecadienoylcarnitine

Description

3-Hydroxyhexadecadienoylcarnitine is an acylcarnitine. More specifically, it is an 3-hydroxyhexadecadienoic 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-Hydroxyhexadecadienoylcarnitine is therefore classified as a long chain AC. As a long-chain acylcarnitine 3-hydroxyhexadecadienoylcarnitine is generally formed through esterification with long-chain fatty acids obtained from the diet. The main function of most long-chain acylcarnitines is to ensure long chain fatty acid transport into the mitochondria (PMID: 22804748 ). Altered levels of long-chain acylcarnitines can serve as useful markers for inherited disorders of long-chain fatty acid metabolism. Carnitine palmitoyltransferase I (CPT I, EC:2.3.1.21) is involved in the synthesis of long-chain acylcarnitines (more than C12) on the mitochondrial outer membrane. Elevated serum/plasma levels of long-chain acylcarnitines are not only markers for incomplete FA oxidation but also are indicators of altered carbohydrate and lipid metabolism. High serum concentrations of long-chain acylcarnitines in the postprandial or fed state are markers of insulin resistance and arise from insulin's inability to inhibit CPT-1-dependent fatty acid metabolism in muscles and the heart (PMID: 19073774 ). Increased intracellular content of long-chain acylcarnitines is thought to serve as a feedback inhibition mechanism of insulin action (PMID: 23258903 ). In healthy subjects, increased concentrations of insulin effectively inhibits long-chain acylcarnitine production. Several studies have also found increased levels of circulating long-chain acylcarnitines in chronic heart failure patients (PMID: 26796394 ). The study of acylcarnitines is an active area of research and it is likely that many novel acylcarnitines will be discovered in the coming years. It is also likely that many novel roles in health and disease will be uncovered. An excellent review of the current state of knowledge for acylcarnitines is available (PMID: 35710135 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

  Mrv1652303202021382D          

 29 28  0  0  0  0            999 V2000
 2493.9443 2499.8005    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2494.6583 2499.3872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2495.3723 2499.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2496.0863 2499.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2496.8003 2499.8005    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2497.5143 2499.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.2282 2499.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.9423 2499.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6564 2499.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3702 2499.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.0841 2499.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.9087 2499.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2495.3723 2500.6248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2493.9443 2500.6248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2493.2303 2501.0360    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
 2492.5122 2500.6230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2493.2303 2501.8607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2492.3773 2501.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2493.2365 2499.3769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2493.2365 2498.5526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2493.9526 2498.1392    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
 2492.5246 2498.1392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.6237 2499.3871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.3377 2499.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2504.1624 2499.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2504.8765 2499.3871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2505.5914 2499.7988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2506.3054 2499.3855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2496.8003 2500.6255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 14  1  6  0  0  0
  1 19  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 13  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
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 12 23  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
  5 29  1  6  0  0  0
M  CHG  2  15   1  21  -1
M  END

HMDB0013335
     RDKit          3D
3-Hydroxyhexadecadienoylcarnitine
 70 69  0  0  0  0  0  0  0  0999 V2000
    8.0675    3.2881   -0.8019 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5682    3.0336   -0.9247 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3383    1.7369   -1.7196 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9971    0.6693   -0.9631 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3734   -0.3545   -0.4935 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9315   -0.6286   -0.6274 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2673   -0.7287    0.6830 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6461   -1.8081    1.1080 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5603   -3.0214    0.3075 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2147   -3.5039   -0.1159 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2188   -3.9257    0.8748 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7018   -2.9911    1.8849 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0785   -1.7753    1.2179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4162   -0.8812    2.3195 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6510   -0.4970    3.1477 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1230    0.3049    1.7408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2980   -0.1132    0.9709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7147   -1.2801    0.9056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9917    0.8575    0.2685 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1440    0.4832   -0.4921 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9777    0.7677   -1.9411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7285    2.1880   -2.2223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6023    3.0088   -1.2978 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6339    2.6118   -3.5354 O   0  0  0  0  0  1  0  0  0  0  0  0
   -5.3052    1.2250    0.0888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5827    1.0333   -0.5012 N   0  0  0  0  0  4  0  0  0  0  0  0
   -6.8878   -0.2555   -1.0172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5542    1.3092    0.5912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9036    2.0188   -1.5197 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5699    2.9455   -1.7448 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4948    2.6895    0.0327 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2338    4.3639   -0.7016 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0596    3.8491   -1.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1455    2.8471    0.0828 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2806    1.6592   -1.8841 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8994    1.8853   -2.6795 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0781    0.7667   -0.7993 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9736   -1.0973    0.0613 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3730    0.1949   -1.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8286   -1.4939   -1.2891 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2697    0.1293    1.3746 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1884   -1.8103    2.1209 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2945   -3.1034   -0.5241 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9842   -3.8444    1.0254 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4059   -4.4073   -0.8024 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7630   -2.7772   -0.8755 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3301   -4.3331    0.3057 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6815   -4.7975    1.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2361   -3.5247    2.3226 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3102   -2.7217    2.7309 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8448   -1.1861    0.6639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7165   -2.1528    0.5732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1066   -1.4535    3.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3669    0.2113    3.7748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4047    0.9112    1.1068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3923    1.0011    2.5810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3002   -0.6379   -0.3746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0864    0.2259   -2.3754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8305    0.3275   -2.5003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4327    0.9343    1.1909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1501    2.3306    0.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2003   -1.0642   -0.7592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8859   -0.5825   -0.5899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1030   -0.2258   -2.1279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1286    0.8399    1.4860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5637    0.9922    0.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5067    2.4188    0.7295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3466    2.9480   -1.2620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9849    2.3012   -1.3766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7508    1.6696   -2.5453 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  2  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
 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
  5 38  1  0
  6 39  1  0
  6 40  1  0
  7 41  1  0
  8 42  1  0
  9 43  1  0
  9 44  1  0
 10 45  1  0
 10 46  1  0
 11 47  1  0
 11 48  1  0
 12 49  1  0
 12 50  1  0
 13 51  1  0
 13 52  1  0
 14 53  1  1
 15 54  1  0
 16 55  1  0
 16 56  1  0
 20 57  1  6
 21 58  1  0
 21 59  1  0
 25 60  1  0
 25 61  1  0
 27 62  1  0
 27 63  1  0
 27 64  1  0
 28 65  1  0
 28 66  1  0
 28 67  1  0
 29 68  1  0
 29 69  1  0
 29 70  1  0
M  CHG  2  24  -1  26   1
M  END

  Mrv1652303202021382D          

 29 28  0  0  0  0            999 V2000
 2493.9443 2499.8005    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2494.6583 2499.3872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2495.3723 2499.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2496.0863 2499.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2496.8003 2499.8005    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2497.5143 2499.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.2282 2499.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.9423 2499.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6564 2499.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3702 2499.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.0841 2499.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.9087 2499.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2495.3723 2500.6248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2493.9443 2500.6248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2493.2303 2501.0360    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
 2492.5122 2500.6230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2493.2303 2501.8607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2492.3773 2501.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2493.2365 2499.3769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2493.2365 2498.5526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2493.9526 2498.1392    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
 2492.5246 2498.1392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.6237 2499.3871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.3377 2499.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2504.1624 2499.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2504.8765 2499.3871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2505.5914 2499.7988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2506.3054 2499.3855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2496.8003 2500.6255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 14  1  6  0  0  0
  1 19  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 13  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
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 12 23  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
  5 29  1  6  0  0  0
M  CHG  2  15   1  21  -1
M  END
> <DATABASE_ID>
HMDB0013335

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C23H41NO5/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/h7-8,10-11,20-21,25H,5-6,9,12-19H2,1-4H3/b8-7-,11-10-/t20-,21-/m1/s1

> <INCHI_KEY>
CPHHQDCIGLXPCO-IMMUWJHFSA-N

> <FORMULA>
C23H41NO5

> <MOLECULAR_WEIGHT>
411.583

> <EXACT_MASS>
411.298473424

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
48.44505247789326

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R)-3-{[(3R,9Z,12Z)-3-hydroxyhexadeca-9,12-dienoyl]oxy}-4-(trimethylazaniumyl)butanoate

> <ALOGPS_LOGP>
-0.28

> <JCHEM_LOGP>
0.07889347386158835

> <ALOGPS_LOGS>
-6.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.000091590500702

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.102434316471337

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7987602226067727

> <JCHEM_POLAR_SURFACE_AREA>
86.66000000000001

> <JCHEM_REFRACTIVITY>
140.82540000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
18

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.20e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-3-{[(3R,9Z,12Z)-3-hydroxyhexadeca-9,12-dienoyl]oxy}-4-(trimethylammonio)butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013335
     RDKit          3D
3-Hydroxyhexadecadienoylcarnitine
 70 69  0  0  0  0  0  0  0  0999 V2000
    8.0675    3.2881   -0.8019 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5682    3.0336   -0.9247 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3383    1.7369   -1.7196 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9971    0.6693   -0.9631 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3734   -0.3545   -0.4935 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9315   -0.6286   -0.6274 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2673   -0.7287    0.6830 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6461   -1.8081    1.1080 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5603   -3.0214    0.3075 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2147   -3.5039   -0.1159 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2188   -3.9257    0.8748 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7018   -2.9911    1.8849 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0785   -1.7753    1.2179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4162   -0.8812    2.3195 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6510   -0.4970    3.1477 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1230    0.3049    1.7408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2980   -0.1132    0.9709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7147   -1.2801    0.9056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9917    0.8575    0.2685 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1440    0.4832   -0.4921 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9777    0.7677   -1.9411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7285    2.1880   -2.2223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6023    3.0088   -1.2978 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6339    2.6118   -3.5354 O   0  0  0  0  0  1  0  0  0  0  0  0
   -5.3052    1.2250    0.0888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5827    1.0333   -0.5012 N   0  0  0  0  0  4  0  0  0  0  0  0
   -6.8878   -0.2555   -1.0172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5542    1.3092    0.5912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9036    2.0188   -1.5197 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5699    2.9455   -1.7448 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4948    2.6895    0.0327 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2338    4.3639   -0.7016 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0596    3.8491   -1.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1455    2.8471    0.0828 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2806    1.6592   -1.8841 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8994    1.8853   -2.6795 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0781    0.7667   -0.7993 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9736   -1.0973    0.0613 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3730    0.1949   -1.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8286   -1.4939   -1.2891 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2697    0.1293    1.3746 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1884   -1.8103    2.1209 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2945   -3.1034   -0.5241 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9842   -3.8444    1.0254 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4059   -4.4073   -0.8024 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7630   -2.7772   -0.8755 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3301   -4.3331    0.3057 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6815   -4.7975    1.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2361   -3.5247    2.3226 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3102   -2.7217    2.7309 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8448   -1.1861    0.6639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7165   -2.1528    0.5732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1066   -1.4535    3.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3669    0.2113    3.7748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4047    0.9112    1.1068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3923    1.0011    2.5810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3002   -0.6379   -0.3746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0864    0.2259   -2.3754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8305    0.3275   -2.5003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4327    0.9343    1.1909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1501    2.3306    0.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2003   -1.0642   -0.7592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8859   -0.5825   -0.5899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1030   -0.2258   -2.1279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1286    0.8399    1.4860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5637    0.9922    0.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5067    2.4188    0.7295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3466    2.9480   -1.2620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9849    2.3012   -1.3766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7508    1.6696   -2.5453 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  2  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
 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
  5 38  1  0
  6 39  1  0
  6 40  1  0
  7 41  1  0
  8 42  1  0
  9 43  1  0
  9 44  1  0
 10 45  1  0
 10 46  1  0
 11 47  1  0
 11 48  1  0
 12 49  1  0
 12 50  1  0
 13 51  1  0
 13 52  1  0
 14 53  1  1
 15 54  1  0
 16 55  1  0
 16 56  1  0
 20 57  1  6
 21 58  1  0
 21 59  1  0
 25 60  1  0
 25 61  1  0
 27 62  1  0
 27 63  1  0
 27 64  1  0
 28 65  1  0
 28 66  1  0
 28 67  1  0
 29 68  1  0
 29 69  1  0
 29 70  1  0
M  CHG  2  24  -1  26   1
M  END

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0    4655.3634666.294   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    4656.6954665.523   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    4658.0284666.294   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    4659.3614665.523   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    4660.6944666.294   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    4662.0274665.523   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    4663.3594666.294   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    4664.6924665.523   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    4666.0254666.294   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    4667.3584665.523   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    4668.6904666.294   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    4670.2304666.294   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0    4658.0284667.833   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0    4655.3634667.833   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0    4654.0304668.601   0.000  0.00  0.00           N+1
HETATM   16  C   UNK     0    4652.6894667.830   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    4654.0304670.140   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    4652.4384669.521   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    4654.0414665.504   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    4654.0414663.965   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0    4655.3784663.193   0.000  0.00  0.00           O-1
HETATM   22  O   UNK     0    4652.7134663.193   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0    4671.5644665.523   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    4672.8974666.294   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    4674.4364666.294   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    4675.7694665.523   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    4677.1044666.291   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    4678.4374665.520   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0    4660.6944667.834   0.000  0.00  0.00           O+0
CONECT    1    2   14   19                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   29                                                  
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   23                                                       
CONECT   13    3                                                            
CONECT   14    1   15                                                       
CONECT   15   14   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15                                                            
CONECT   19    1   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   24   12                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29    5                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   56    0
END

COMPND    HMDB0013335
HETATM    1  C1  UNL     1       8.067   3.288  -0.802  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.568   3.034  -0.925  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.338   1.737  -1.720  1.00  0.00           C  
HETATM    4  C4  UNL     1       6.997   0.669  -0.963  1.00  0.00           C  
HETATM    5  C5  UNL     1       6.373  -0.355  -0.494  1.00  0.00           C  
HETATM    6  C6  UNL     1       4.932  -0.629  -0.627  1.00  0.00           C  
HETATM    7  C7  UNL     1       4.267  -0.729   0.683  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.646  -1.808   1.108  1.00  0.00           C  
HETATM    9  C9  UNL     1       3.560  -3.021   0.308  1.00  0.00           C  
HETATM   10  C10 UNL     1       2.215  -3.504  -0.116  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.219  -3.926   0.875  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.702  -2.991   1.885  1.00  0.00           C  
HETATM   13  C13 UNL     1       0.079  -1.775   1.218  1.00  0.00           C  
HETATM   14  C14 UNL     1      -0.416  -0.881   2.320  1.00  0.00           C  
HETATM   15  O1  UNL     1       0.651  -0.497   3.148  1.00  0.00           O  
HETATM   16  C15 UNL     1      -1.123   0.305   1.741  1.00  0.00           C  
HETATM   17  C16 UNL     1      -2.298  -0.113   0.971  1.00  0.00           C  
HETATM   18  O2  UNL     1      -2.715  -1.280   0.906  1.00  0.00           O  
HETATM   19  O3  UNL     1      -2.992   0.857   0.268  1.00  0.00           O  
HETATM   20  C17 UNL     1      -4.144   0.483  -0.492  1.00  0.00           C  
HETATM   21  C18 UNL     1      -3.978   0.768  -1.941  1.00  0.00           C  
HETATM   22  C19 UNL     1      -3.728   2.188  -2.222  1.00  0.00           C  
HETATM   23  O4  UNL     1      -3.602   3.009  -1.298  1.00  0.00           O  
HETATM   24  O5  UNL     1      -3.634   2.612  -3.535  1.00  0.00           O1-
HETATM   25  C20 UNL     1      -5.305   1.225   0.089  1.00  0.00           C  
HETATM   26  N1  UNL     1      -6.583   1.033  -0.501  1.00  0.00           N1+
HETATM   27  C21 UNL     1      -6.888  -0.255  -1.017  1.00  0.00           C  
HETATM   28  C22 UNL     1      -7.554   1.309   0.591  1.00  0.00           C  
HETATM   29  C23 UNL     1      -6.904   2.019  -1.520  1.00  0.00           C  
HETATM   30  H1  UNL     1       8.570   2.945  -1.745  1.00  0.00           H  
HETATM   31  H2  UNL     1       8.495   2.689   0.033  1.00  0.00           H  
HETATM   32  H3  UNL     1       8.234   4.364  -0.702  1.00  0.00           H  
HETATM   33  H4  UNL     1       6.060   3.849  -1.441  1.00  0.00           H  
HETATM   34  H5  UNL     1       6.145   2.847   0.083  1.00  0.00           H  
HETATM   35  H6  UNL     1       5.281   1.659  -1.884  1.00  0.00           H  
HETATM   36  H7  UNL     1       6.899   1.885  -2.679  1.00  0.00           H  
HETATM   37  H8  UNL     1       8.078   0.767  -0.799  1.00  0.00           H  
HETATM   38  H9  UNL     1       6.974  -1.097   0.061  1.00  0.00           H  
HETATM   39  H10 UNL     1       4.373   0.195  -1.175  1.00  0.00           H  
HETATM   40  H11 UNL     1       4.829  -1.494  -1.289  1.00  0.00           H  
HETATM   41  H12 UNL     1       4.270   0.129   1.375  1.00  0.00           H  
HETATM   42  H13 UNL     1       3.188  -1.810   2.121  1.00  0.00           H  
HETATM   43  H14 UNL     1       4.295  -3.103  -0.524  1.00  0.00           H  
HETATM   44  H15 UNL     1       3.984  -3.844   1.025  1.00  0.00           H  
HETATM   45  H16 UNL     1       2.406  -4.407  -0.802  1.00  0.00           H  
HETATM   46  H17 UNL     1       1.763  -2.777  -0.875  1.00  0.00           H  
HETATM   47  H18 UNL     1       0.330  -4.333   0.306  1.00  0.00           H  
HETATM   48  H19 UNL     1       1.681  -4.797   1.445  1.00  0.00           H  
HETATM   49  H20 UNL     1      -0.236  -3.525   2.323  1.00  0.00           H  
HETATM   50  H21 UNL     1       1.310  -2.722   2.731  1.00  0.00           H  
HETATM   51  H22 UNL     1       0.845  -1.186   0.664  1.00  0.00           H  
HETATM   52  H23 UNL     1      -0.716  -2.153   0.573  1.00  0.00           H  
HETATM   53  H24 UNL     1      -1.107  -1.453   3.001  1.00  0.00           H  
HETATM   54  H25 UNL     1       0.367   0.211   3.775  1.00  0.00           H  
HETATM   55  H26 UNL     1      -0.405   0.911   1.107  1.00  0.00           H  
HETATM   56  H27 UNL     1      -1.392   1.001   2.581  1.00  0.00           H  
HETATM   57  H28 UNL     1      -4.300  -0.638  -0.375  1.00  0.00           H  
HETATM   58  H29 UNL     1      -3.086   0.226  -2.375  1.00  0.00           H  
HETATM   59  H30 UNL     1      -4.831   0.327  -2.500  1.00  0.00           H  
HETATM   60  H31 UNL     1      -5.433   0.934   1.191  1.00  0.00           H  
HETATM   61  H32 UNL     1      -5.150   2.331   0.170  1.00  0.00           H  
HETATM   62  H33 UNL     1      -6.200  -1.064  -0.759  1.00  0.00           H  
HETATM   63  H34 UNL     1      -7.886  -0.583  -0.590  1.00  0.00           H  
HETATM   64  H35 UNL     1      -7.103  -0.226  -2.128  1.00  0.00           H  
HETATM   65  H36 UNL     1      -7.129   0.840   1.486  1.00  0.00           H  
HETATM   66  H37 UNL     1      -8.564   0.992   0.323  1.00  0.00           H  
HETATM   67  H38 UNL     1      -7.507   2.419   0.730  1.00  0.00           H  
HETATM   68  H39 UNL     1      -6.347   2.948  -1.262  1.00  0.00           H  
HETATM   69  H40 UNL     1      -7.985   2.301  -1.377  1.00  0.00           H  
HETATM   70  H41 UNL     1      -6.751   1.670  -2.545  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3   33   34
CONECT    3    4   35   36
CONECT    4    5    5   37
CONECT    5    6   38
CONECT    6    7   39   40
CONECT    7    8    8   41
CONECT    8    9   42
CONECT    9   10   43   44
CONECT   10   11   45   46
CONECT   11   12   47   48
CONECT   12   13   49   50
CONECT   13   14   51   52
CONECT   14   15   16   53
CONECT   15   54
CONECT   16   17   55   56
CONECT   17   18   18   19
CONECT   19   20
CONECT   20   21   25   57
CONECT   21   22   58   59
CONECT   22   23   23   24
CONECT   25   26   60   61
CONECT   26   27   28   29
CONECT   27   62   63   64
CONECT   28   65   66   67
CONECT   29   68   69   70
END

HMDB0013335
     RDKit          3D
3-Hydroxyhexadecadienoylcarnitine
 70 69  0  0  0  0  0  0  0  0999 V2000
    8.0675    3.2881   -0.8019 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5682    3.0336   -0.9247 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3383    1.7369   -1.7196 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9971    0.6693   -0.9631 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3734   -0.3545   -0.4935 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9315   -0.6286   -0.6274 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2673   -0.7287    0.6830 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6461   -1.8081    1.1080 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5603   -3.0214    0.3075 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2147   -3.5039   -0.1159 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2188   -3.9257    0.8748 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7018   -2.9911    1.8849 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0785   -1.7753    1.2179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4162   -0.8812    2.3195 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6510   -0.4970    3.1477 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1230    0.3049    1.7408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2980   -0.1132    0.9709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7147   -1.2801    0.9056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9917    0.8575    0.2685 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1440    0.4832   -0.4921 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9777    0.7677   -1.9411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7285    2.1880   -2.2223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6023    3.0088   -1.2978 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6339    2.6118   -3.5354 O   0  0  0  0  0  1  0  0  0  0  0  0
   -5.3052    1.2250    0.0888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5827    1.0333   -0.5012 N   0  0  0  0  0  4  0  0  0  0  0  0
   -6.8878   -0.2555   -1.0172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5542    1.3092    0.5912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9036    2.0188   -1.5197 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5699    2.9455   -1.7448 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4948    2.6895    0.0327 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2338    4.3639   -0.7016 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0596    3.8491   -1.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1455    2.8471    0.0828 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2806    1.6592   -1.8841 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8994    1.8853   -2.6795 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0781    0.7667   -0.7993 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9736   -1.0973    0.0613 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3730    0.1949   -1.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8286   -1.4939   -1.2891 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2697    0.1293    1.3746 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1884   -1.8103    2.1209 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2945   -3.1034   -0.5241 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9842   -3.8444    1.0254 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4059   -4.4073   -0.8024 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7630   -2.7772   -0.8755 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3301   -4.3331    0.3057 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6815   -4.7975    1.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2361   -3.5247    2.3226 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3102   -2.7217    2.7309 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8448   -1.1861    0.6639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7165   -2.1528    0.5732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1066   -1.4535    3.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3669    0.2113    3.7748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4047    0.9112    1.1068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3923    1.0011    2.5810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3002   -0.6379   -0.3746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0864    0.2259   -2.3754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8305    0.3275   -2.5003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4327    0.9343    1.1909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1501    2.3306    0.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2003   -1.0642   -0.7592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8859   -0.5825   -0.5899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1030   -0.2258   -2.1279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1286    0.8399    1.4860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5637    0.9922    0.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5067    2.4188    0.7295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3466    2.9480   -1.2620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9849    2.3012   -1.3766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7508    1.6696   -2.5453 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  2  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
 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
  5 38  1  0
  6 39  1  0
  6 40  1  0
  7 41  1  0
  8 42  1  0
  9 43  1  0
  9 44  1  0
 10 45  1  0
 10 46  1  0
 11 47  1  0
 11 48  1  0
 12 49  1  0
 12 50  1  0
 13 51  1  0
 13 52  1  0
 14 53  1  1
 15 54  1  0
 16 55  1  0
 16 56  1  0
 20 57  1  6
 21 58  1  0
 21 59  1  0
 25 60  1  0
 25 61  1  0
 27 62  1  0
 27 63  1  0
 27 64  1  0
 28 65  1  0
 28 66  1  0
 28 67  1  0
 29 68  1  0
 29 69  1  0
 29 70  1  0
M  CHG  2  24  -1  26   1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(3R)-3-{[(3R,9Z,12Z)-3-hydroxyhexadeca-9,12-dienoyl]oxy}-4-(trimethylazaniumyl)butanoic acid	HMDB
(9Z,12Z)-3-Hydroxyhexadecadienoylcarnitine	HMDB
3-Hydroxyhexadecadienoylcarnitine	HMDB

Chemical Formula

C₂₃H₄₁NO₅

Average Molecular Weight

411.583

Monoisotopic Molecular Weight

411.298473424

IUPAC Name

(3R)-3-{[(3R,9Z,12Z)-3-hydroxyhexadeca-9,12-dienoyl]oxy}-4-(trimethylazaniumyl)butanoate

Traditional Name

(3R)-3-{[(3R,9Z,12Z)-3-hydroxyhexadeca-9,12-dienoyl]oxy}-4-(trimethylammonio)butanoate

CAS Registry Number

Not Available

SMILES

CCC\C=C/C\C=C/CCCCC[C@@H](O)CC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C

InChI Identifier

InChI=1S/C23H41NO5/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/h7-8,10-11,20-21,25H,5-6,9,12-19H2,1-4H3/b8-7-,11-10-/t20-,21-/m1/s1

InChI Key

CPHHQDCIGLXPCO-IMMUWJHFSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Acyl carnitines

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0013335)

Excreta

Biofluid or Excreta

Urine (PMID: 32340350)

Cell

All cells and tissues (PMID: 35710135)

Cellular substructure

Cytoplasm (PMID: 35710135)
Mitochondrion matrix (PMID: 35710135)

Organelle

Peroxisome (PMID: 35710135)

Source

Endogenous

Endogenous (HMDB: HMDB0013335)

Exogenous

Food

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Process

Not Available

Role

Biological role

Energy source (PMID: 35710135)

Industrial application

Pharmaceutical industry

Biomarker

Physical Properties

State

Solid

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00028 g/L	ALOGPS
logP	-0.28	ALOGPS
logP	0.079	ChemAxon
logS	-6.3	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	18	ChemAxon
Refractivity	140.83 m³·mol⁻¹	ChemAxon
Polarizability	48.45 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]+	221.857	30932474
DeepCCS	[M-H]-	218.597	30932474
DeepCCS	[M-2H]-	252.854	30932474
DeepCCS	[M+Na]+	229.355	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxyhexadecadienoylcarnitine	CCC\C=C/C\C=C/CCCCC[C@@H](O)CC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C	3498.2	Standard polar	33892256
3-Hydroxyhexadecadienoylcarnitine	CCC\C=C/C\C=C/CCCCC[C@@H](O)CC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C	2591.6	Standard non polar	33892256
3-Hydroxyhexadecadienoylcarnitine	CCC\C=C/C\C=C/CCCCC[C@@H](O)CC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C	2855.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxyhexadecadienoylcarnitine,1TMS,isomer #1	CCC/C=C\C/C=C\CCCCC[C@H](CC(=O)O[C@H](CC(=O)[O-])C[N+](C)(C)C)O[Si](C)(C)C	2823.6	Semi standard non polar	33892256
3-Hydroxyhexadecadienoylcarnitine,1TBDMS,isomer #1	CCC/C=C\C/C=C\CCCCC[C@H](CC(=O)O[C@H](CC(=O)[O-])C[N+](C)(C)C)O[Si](C)(C)C(C)(C)C	3064.8	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-Hydroxyhexadecadienoylcarnitine 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-Hydroxyhexadecadienoylcarnitine 10V, Positive-QTOF	splash10-03di-0000900000-1269b367e35d410eba46	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyhexadecadienoylcarnitine 20V, Positive-QTOF	splash10-01p9-9000500000-24738fda1f7bf7078e91	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyhexadecadienoylcarnitine 40V, Positive-QTOF	splash10-000i-9000000000-e9262cbaff8cb4ad0ba6	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.000-0.030 uM	Adult (>18 years old)	Both	Normal	Molecular You	details
Urine	Detected and Quantified	0.0-0.01 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	32340350	details
Urine	Detected and Quantified	0.0(0.0-0.01) umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	32340350	details
Urine	Detected and Quantified	0.0(0.0-0.01) umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	32340350	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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

156908017

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

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 ]
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-Hydroxyhexadecadienoylcarnitine (HMDB0013335)

MOL for HMDB0013335 (3-Hydroxyhexadecadienoylcarnitine)

3D MOL for HMDB0013335 (3-Hydroxyhexadecadienoylcarnitine)

3D SDF for HMDB0013335 (3-Hydroxyhexadecadienoylcarnitine)

3D-SDF for HMDB0013335 (3-Hydroxyhexadecadienoylcarnitine)

PDB for HMDB0013335 (3-Hydroxyhexadecadienoylcarnitine)

3D PDB for HMDB0013335 (3-Hydroxyhexadecadienoylcarnitine)

SMILES for HMDB0013335 (3-Hydroxyhexadecadienoylcarnitine)

INCHI for HMDB0013335 (3-Hydroxyhexadecadienoylcarnitine)

Structure for HMDB0013335 (3-Hydroxyhexadecadienoylcarnitine)

3D Structure for HMDB0013335 (3-Hydroxyhexadecadienoylcarnitine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra