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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2009-11-30 15:50:17 UTC

Update Date

2022-10-24 19:44:12 UTC

HMDB ID

HMDB0013166

Secondary Accession Numbers

HMDB13166

Metabolite Identification

Common Name

2-Hydroxymyristoylcarnitine

Description

2-Hydroxymyristoylcarnitine is an acylcarnitine. More specifically, it is an 2-hydroxymyristic 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. 2-Hydroxymyristoylcarnitine is therefore classified as a long chain AC. As a long-chain acylcarnitine 2-hydroxymyristoylcarnitine 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 2-hydroxymyristoylcarnitine is elevated in the blood or plasma of individuals with CVD in type 2 diabetes mellitus (PMID: 32431666 ). 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


  Mrv0541 02251208182D          

 27 26  0  0  0  0            999 V2000
   11.2120   -9.1116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9264   -8.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6409   -9.1116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3554   -8.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0699   -9.1116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7844   -8.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4988   -9.1116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2133   -8.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9278   -9.1116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9278   -9.9366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6423   -8.6991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6423   -7.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3567   -7.4616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0713   -7.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0713   -8.6991    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   19.7857   -7.4616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9278   -7.4616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9278   -6.6366    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   17.7528   -6.6366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1028   -6.6366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9278   -5.8116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4975   -8.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7830   -9.1116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0686   -8.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2133   -7.8740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3541   -9.1116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6396   -8.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
 11  9  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 12 11  1  0  0  0  0
 14 16  2  0  0  0  0
 17 12  1  0  0  0  0
 18 17  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 22  1  1  0  0  0  0
 23 22  1  0  0  0  0
 24 23  1  0  0  0  0
 25  8  1  0  0  0  0
 26 24  1  0  0  0  0
 27 26  1  0  0  0  0
M  CHG  2  15  -1  18   1
M  END

HMDB0013166
     RDKit          3D
2-Hydroxymyristoylcarnitine
 68 67  0  0  0  0  0  0  0  0999 V2000
    6.6557    2.5326    1.7232 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2414    1.3494    0.7921 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4619    0.7610    0.2374 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4488   -0.3895   -0.6704 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8044   -0.2922   -1.9692 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3990   -0.0429   -2.1627 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3209   -0.9357   -1.6914 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1823   -1.0891   -0.2438 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0479   -2.0373    0.1484 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7065   -1.5540   -0.3588 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6927   -2.5748    0.0966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6649   -2.1995   -0.3638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1753   -0.8750    0.1337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2327   -0.8425    1.5192 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5320   -0.5805   -0.4538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7205   -0.5569   -1.6889 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5615   -0.3374    0.3989 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8984   -0.0448    0.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7281   -1.2109    0.4597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6584   -1.3876    1.9449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9789   -0.6408    2.6930 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3626   -2.4082    2.5406 O   0  0  0  0  0  1  0  0  0  0  0  0
   -5.3528    1.2798    0.4788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6669    1.7008    0.1603 N   0  0  0  0  0  4  0  0  0  0  0  0
   -7.5856    1.5333    1.3087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6810    3.1670   -0.0532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3131    1.0988   -0.9507 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2754    2.1029    2.5299 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7252    2.9969    2.0603 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2760    3.1827    1.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7605    0.5897    1.4656 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5263    1.8275    0.1088 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0738    1.6227   -0.1968 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1052    0.4333    1.1391 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2215   -1.3696   -0.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6022   -0.6489   -0.8974 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1695   -1.1635   -2.6548 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3453    0.5974   -2.5231 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1914    0.0442   -3.3319 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0709    1.0198   -1.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4157   -1.9597   -2.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3585   -0.5076   -2.1533 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0937   -1.3834    0.2544 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8701   -0.0974    0.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2425   -3.0203   -0.3099 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0124   -2.1735    1.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4274   -0.5809    0.0968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7329   -1.5500   -1.4507 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9465   -3.5542   -0.3643 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6979   -2.6463    1.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7670   -2.3020   -1.4674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3791   -2.9714    0.0465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4776   -0.0854   -0.2031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2533    0.1205    1.7922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8593   -0.0715   -1.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7760   -1.1914    0.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3209   -2.1833    0.0498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1620    1.4037    1.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6468    2.0407    0.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5348    2.0829    1.1048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1558    1.9807    2.2240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8269    0.4924    1.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0255    3.4398   -0.8919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3876    3.6642    0.8797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7573    3.4242   -0.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2207    0.4986   -0.6635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7658    1.9228   -1.5819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6731    0.5496   -1.6593 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
 13 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 18 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 24 27  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  0
  6 40  1  0
  7 41  1  0
  7 42  1  0
  8 43  1  0
  8 44  1  0
  9 45  1  0
  9 46  1  0
 10 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 12 51  1  0
 12 52  1  0
 13 53  1  0
 14 54  1  0
 18 55  1  0
 19 56  1  0
 19 57  1  0
 23 58  1  0
 23 59  1  0
 25 60  1  0
 25 61  1  0
 25 62  1  0
 26 63  1  0
 26 64  1  0
 26 65  1  0
 27 66  1  0
 27 67  1  0
 27 68  1  0
M  CHG  2  22  -1  24   1
M  END


  Mrv0541 02251208182D          

 27 26  0  0  0  0            999 V2000
   11.2120   -9.1116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9264   -8.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6409   -9.1116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3554   -8.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0699   -9.1116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7844   -8.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4988   -9.1116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2133   -8.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9278   -9.1116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9278   -9.9366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6423   -8.6991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6423   -7.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3567   -7.4616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0713   -7.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0713   -8.6991    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   19.7857   -7.4616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9278   -7.4616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9278   -6.6366    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   17.7528   -6.6366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1028   -6.6366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9278   -5.8116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4975   -8.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7830   -9.1116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0686   -8.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2133   -7.8740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3541   -9.1116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6396   -8.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
 11  9  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 12 11  1  0  0  0  0
 14 16  2  0  0  0  0
 17 12  1  0  0  0  0
 18 17  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 22  1  1  0  0  0  0
 23 22  1  0  0  0  0
 24 23  1  0  0  0  0
 25  8  1  0  0  0  0
 26 24  1  0  0  0  0
 27 26  1  0  0  0  0
M  CHG  2  15  -1  18   1
M  END
> <DATABASE_ID>
HMDB0013166

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H41NO5/c1-5-6-7-8-9-10-11-12-13-14-15-19(23)21(26)27-18(16-20(24)25)17-22(2,3)4/h18-19,23H,5-17H2,1-4H3

> <INCHI_KEY>
WWDZVVWQNWNRDM-UHFFFAOYSA-N

> <FORMULA>
C21H41NO5

> <MOLECULAR_WEIGHT>
387.5539

> <EXACT_MASS>
387.298473427

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
47.02964537862937

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[(2-hydroxytetradecanoyl)oxy]-4-(trimethylazaniumyl)butanoate

> <ALOGPS_LOGP>
-0.36

> <JCHEM_LOGP>
0.2733446035282538

> <ALOGPS_LOGS>
-6.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.70403588929113

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.102434141023542

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8031681922566483

> <JCHEM_POLAR_SURFACE_AREA>
86.66000000000001

> <JCHEM_REFRACTIVITY>
129.3669

> <JCHEM_ROTATABLE_BOND_COUNT>
18

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.83e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(2-hydroxytetradecanoyl)oxy]-4-(trimethylammonio)butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013166
     RDKit          3D
2-Hydroxymyristoylcarnitine
 68 67  0  0  0  0  0  0  0  0999 V2000
    6.6557    2.5326    1.7232 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2414    1.3494    0.7921 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4619    0.7610    0.2374 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4488   -0.3895   -0.6704 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8044   -0.2922   -1.9692 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3990   -0.0429   -2.1627 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3209   -0.9357   -1.6914 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1823   -1.0891   -0.2438 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0479   -2.0373    0.1484 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7065   -1.5540   -0.3588 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6927   -2.5748    0.0966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6649   -2.1995   -0.3638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1753   -0.8750    0.1337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2327   -0.8425    1.5192 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5320   -0.5805   -0.4538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7205   -0.5569   -1.6889 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5615   -0.3374    0.3989 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8984   -0.0448    0.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7281   -1.2109    0.4597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6584   -1.3876    1.9449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9789   -0.6408    2.6930 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3626   -2.4082    2.5406 O   0  0  0  0  0  1  0  0  0  0  0  0
   -5.3528    1.2798    0.4788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6669    1.7008    0.1603 N   0  0  0  0  0  4  0  0  0  0  0  0
   -7.5856    1.5333    1.3087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6810    3.1670   -0.0532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3131    1.0988   -0.9507 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2754    2.1029    2.5299 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7252    2.9969    2.0603 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2760    3.1827    1.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7605    0.5897    1.4656 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5263    1.8275    0.1088 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0738    1.6227   -0.1968 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1052    0.4333    1.1391 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2215   -1.3696   -0.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6022   -0.6489   -0.8974 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1695   -1.1635   -2.6548 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3453    0.5974   -2.5231 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1914    0.0442   -3.3319 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0709    1.0198   -1.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4157   -1.9597   -2.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3585   -0.5076   -2.1533 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0937   -1.3834    0.2544 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8701   -0.0974    0.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2425   -3.0203   -0.3099 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0124   -2.1735    1.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4274   -0.5809    0.0968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7329   -1.5500   -1.4507 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9465   -3.5542   -0.3643 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6979   -2.6463    1.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7670   -2.3020   -1.4674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3791   -2.9714    0.0465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4776   -0.0854   -0.2031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2533    0.1205    1.7922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8593   -0.0715   -1.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7760   -1.1914    0.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3209   -2.1833    0.0498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1620    1.4037    1.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6468    2.0407    0.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5348    2.0829    1.1048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1558    1.9807    2.2240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8269    0.4924    1.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0255    3.4398   -0.8919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3876    3.6642    0.8797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7573    3.4242   -0.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2207    0.4986   -0.6635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7658    1.9228   -1.5819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6731    0.5496   -1.6593 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
 13 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 18 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 24 27  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  0
  6 40  1  0
  7 41  1  0
  7 42  1  0
  8 43  1  0
  8 44  1  0
  9 45  1  0
  9 46  1  0
 10 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 12 51  1  0
 12 52  1  0
 13 53  1  0
 14 54  1  0
 18 55  1  0
 19 56  1  0
 19 57  1  0
 23 58  1  0
 23 59  1  0
 25 60  1  0
 25 61  1  0
 25 62  1  0
 26 63  1  0
 26 64  1  0
 26 65  1  0
 27 66  1  0
 27 67  1  0
 27 68  1  0
M  CHG  2  22  -1  24   1
M  END

HEADER    PROTEIN                                 25-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-FEB-12         0                                  
HETATM    1  C   UNK     0      20.929 -17.008   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      22.263 -16.238   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      23.596 -17.008   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      24.930 -16.238   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      26.264 -17.008   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      27.598 -16.238   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      28.931 -17.008   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      30.265 -16.238   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      31.599 -17.008   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      31.599 -18.548   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      32.932 -16.238   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      32.932 -14.698   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      34.266 -13.928   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      35.600 -14.698   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      35.600 -16.238   0.000  0.00  0.00           O-1
HETATM   16  O   UNK     0      36.933 -13.928   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      31.599 -13.928   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      31.599 -12.388   0.000  0.00  0.00           N+1
HETATM   19  C   UNK     0      33.139 -12.388   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      30.059 -12.388   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      31.599 -10.848   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      19.595 -16.238   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      18.262 -17.008   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.928 -16.238   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      30.265 -14.698   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      15.594 -17.008   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      14.261 -16.238   0.000  0.00  0.00           C+0
CONECT    1    2   22                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   25                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   13   11   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   12   18                                                       
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18                                                            
CONECT   22    1   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   26                                                       
CONECT   25    8                                                            
CONECT   26   24   27                                                       
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   52    0
END

COMPND    HMDB0013166
HETATM    1  C1  UNL     1       6.656   2.533   1.723  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.241   1.349   0.792  1.00  0.00           C  
HETATM    3  C3  UNL     1       7.462   0.761   0.237  1.00  0.00           C  
HETATM    4  C4  UNL     1       7.449  -0.389  -0.670  1.00  0.00           C  
HETATM    5  C5  UNL     1       6.804  -0.292  -1.969  1.00  0.00           C  
HETATM    6  C6  UNL     1       5.399  -0.043  -2.163  1.00  0.00           C  
HETATM    7  C7  UNL     1       4.321  -0.936  -1.691  1.00  0.00           C  
HETATM    8  C8  UNL     1       4.182  -1.089  -0.244  1.00  0.00           C  
HETATM    9  C9  UNL     1       3.048  -2.037   0.148  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.707  -1.554  -0.359  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.693  -2.575   0.097  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.665  -2.199  -0.364  1.00  0.00           C  
HETATM   13  C13 UNL     1      -1.175  -0.875   0.134  1.00  0.00           C  
HETATM   14  O1  UNL     1      -1.233  -0.842   1.519  1.00  0.00           O  
HETATM   15  C14 UNL     1      -2.532  -0.580  -0.454  1.00  0.00           C  
HETATM   16  O2  UNL     1      -2.721  -0.557  -1.689  1.00  0.00           O  
HETATM   17  O3  UNL     1      -3.562  -0.337   0.399  1.00  0.00           O  
HETATM   18  C15 UNL     1      -4.898  -0.045   0.000  1.00  0.00           C  
HETATM   19  C16 UNL     1      -5.728  -1.211   0.460  1.00  0.00           C  
HETATM   20  C17 UNL     1      -5.658  -1.388   1.945  1.00  0.00           C  
HETATM   21  O4  UNL     1      -4.979  -0.641   2.693  1.00  0.00           O  
HETATM   22  O5  UNL     1      -6.363  -2.408   2.541  1.00  0.00           O1-
HETATM   23  C18 UNL     1      -5.353   1.280   0.479  1.00  0.00           C  
HETATM   24  N1  UNL     1      -6.667   1.701   0.160  1.00  0.00           N1+
HETATM   25  C19 UNL     1      -7.586   1.533   1.309  1.00  0.00           C  
HETATM   26  C20 UNL     1      -6.681   3.167  -0.053  1.00  0.00           C  
HETATM   27  C21 UNL     1      -7.313   1.099  -0.951  1.00  0.00           C  
HETATM   28  H1  UNL     1       7.275   2.103   2.530  1.00  0.00           H  
HETATM   29  H2  UNL     1       5.725   2.997   2.060  1.00  0.00           H  
HETATM   30  H3  UNL     1       7.276   3.183   1.088  1.00  0.00           H  
HETATM   31  H4  UNL     1       5.760   0.590   1.466  1.00  0.00           H  
HETATM   32  H5  UNL     1       5.526   1.827   0.109  1.00  0.00           H  
HETATM   33  H6  UNL     1       8.074   1.623  -0.197  1.00  0.00           H  
HETATM   34  H7  UNL     1       8.105   0.433   1.139  1.00  0.00           H  
HETATM   35  H8  UNL     1       7.222  -1.370  -0.137  1.00  0.00           H  
HETATM   36  H9  UNL     1       8.602  -0.649  -0.897  1.00  0.00           H  
HETATM   37  H10 UNL     1       7.170  -1.164  -2.655  1.00  0.00           H  
HETATM   38  H11 UNL     1       7.345   0.597  -2.523  1.00  0.00           H  
HETATM   39  H12 UNL     1       5.191   0.044  -3.332  1.00  0.00           H  
HETATM   40  H13 UNL     1       5.071   1.020  -1.897  1.00  0.00           H  
HETATM   41  H14 UNL     1       4.416  -1.960  -2.184  1.00  0.00           H  
HETATM   42  H15 UNL     1       3.358  -0.508  -2.153  1.00  0.00           H  
HETATM   43  H16 UNL     1       5.094  -1.383   0.254  1.00  0.00           H  
HETATM   44  H17 UNL     1       3.870  -0.097   0.183  1.00  0.00           H  
HETATM   45  H18 UNL     1       3.243  -3.020  -0.310  1.00  0.00           H  
HETATM   46  H19 UNL     1       3.012  -2.174   1.246  1.00  0.00           H  
HETATM   47  H20 UNL     1       1.427  -0.581   0.097  1.00  0.00           H  
HETATM   48  H21 UNL     1       1.733  -1.550  -1.451  1.00  0.00           H  
HETATM   49  H22 UNL     1       0.947  -3.554  -0.364  1.00  0.00           H  
HETATM   50  H23 UNL     1       0.698  -2.646   1.213  1.00  0.00           H  
HETATM   51  H24 UNL     1      -0.767  -2.302  -1.467  1.00  0.00           H  
HETATM   52  H25 UNL     1      -1.379  -2.971   0.046  1.00  0.00           H  
HETATM   53  H26 UNL     1      -0.478  -0.085  -0.203  1.00  0.00           H  
HETATM   54  H27 UNL     1      -1.253   0.121   1.792  1.00  0.00           H  
HETATM   55  H28 UNL     1      -4.859  -0.072  -1.109  1.00  0.00           H  
HETATM   56  H29 UNL     1      -6.776  -1.191   0.177  1.00  0.00           H  
HETATM   57  H30 UNL     1      -5.321  -2.183   0.050  1.00  0.00           H  
HETATM   58  H31 UNL     1      -5.162   1.404   1.587  1.00  0.00           H  
HETATM   59  H32 UNL     1      -4.647   2.041   0.023  1.00  0.00           H  
HETATM   60  H33 UNL     1      -8.535   2.083   1.105  1.00  0.00           H  
HETATM   61  H34 UNL     1      -7.156   1.981   2.224  1.00  0.00           H  
HETATM   62  H35 UNL     1      -7.827   0.492   1.509  1.00  0.00           H  
HETATM   63  H36 UNL     1      -6.026   3.440  -0.892  1.00  0.00           H  
HETATM   64  H37 UNL     1      -6.388   3.664   0.880  1.00  0.00           H  
HETATM   65  H38 UNL     1      -7.757   3.424  -0.234  1.00  0.00           H  
HETATM   66  H39 UNL     1      -8.221   0.499  -0.663  1.00  0.00           H  
HETATM   67  H40 UNL     1      -7.766   1.923  -1.582  1.00  0.00           H  
HETATM   68  H41 UNL     1      -6.673   0.550  -1.659  1.00  0.00           H  
CONECT    1    2   28   29   30
CONECT    2    3   31   32
CONECT    3    4   33   34
CONECT    4    5   35   36
CONECT    5    6   37   38
CONECT    6    7   39   40
CONECT    7    8   41   42
CONECT    8    9   43   44
CONECT    9   10   45   46
CONECT   10   11   47   48
CONECT   11   12   49   50
CONECT   12   13   51   52
CONECT   13   14   15   53
CONECT   14   54
CONECT   15   16   16   17
CONECT   17   18
CONECT   18   19   23   55
CONECT   19   20   56   57
CONECT   20   21   21   22
CONECT   23   24   58   59
CONECT   24   25   26   27
CONECT   25   60   61   62
CONECT   26   63   64   65
CONECT   27   66   67   68
END

HMDB0013166
     RDKit          3D
2-Hydroxymyristoylcarnitine
 68 67  0  0  0  0  0  0  0  0999 V2000
    6.6557    2.5326    1.7232 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2414    1.3494    0.7921 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4619    0.7610    0.2374 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4488   -0.3895   -0.6704 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8044   -0.2922   -1.9692 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3990   -0.0429   -2.1627 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3209   -0.9357   -1.6914 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1823   -1.0891   -0.2438 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0479   -2.0373    0.1484 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7065   -1.5540   -0.3588 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6927   -2.5748    0.0966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6649   -2.1995   -0.3638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1753   -0.8750    0.1337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2327   -0.8425    1.5192 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5320   -0.5805   -0.4538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7205   -0.5569   -1.6889 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5615   -0.3374    0.3989 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8984   -0.0448    0.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7281   -1.2109    0.4597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6584   -1.3876    1.9449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9789   -0.6408    2.6930 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3626   -2.4082    2.5406 O   0  0  0  0  0  1  0  0  0  0  0  0
   -5.3528    1.2798    0.4788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6669    1.7008    0.1603 N   0  0  0  0  0  4  0  0  0  0  0  0
   -7.5856    1.5333    1.3087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6810    3.1670   -0.0532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3131    1.0988   -0.9507 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2754    2.1029    2.5299 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7252    2.9969    2.0603 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2760    3.1827    1.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7605    0.5897    1.4656 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5263    1.8275    0.1088 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0738    1.6227   -0.1968 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1052    0.4333    1.1391 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2215   -1.3696   -0.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6022   -0.6489   -0.8974 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1695   -1.1635   -2.6548 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3453    0.5974   -2.5231 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1914    0.0442   -3.3319 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0709    1.0198   -1.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4157   -1.9597   -2.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3585   -0.5076   -2.1533 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0937   -1.3834    0.2544 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8701   -0.0974    0.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2425   -3.0203   -0.3099 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0124   -2.1735    1.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4274   -0.5809    0.0968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7329   -1.5500   -1.4507 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9465   -3.5542   -0.3643 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6979   -2.6463    1.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7670   -2.3020   -1.4674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3791   -2.9714    0.0465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4776   -0.0854   -0.2031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2533    0.1205    1.7922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8593   -0.0715   -1.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7760   -1.1914    0.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3209   -2.1833    0.0498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1620    1.4037    1.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6468    2.0407    0.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5348    2.0829    1.1048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1558    1.9807    2.2240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8269    0.4924    1.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0255    3.4398   -0.8919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3876    3.6642    0.8797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7573    3.4242   -0.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2207    0.4986   -0.6635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7658    1.9228   -1.5819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6731    0.5496   -1.6593 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
 13 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 18 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 24 27  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  0
  6 40  1  0
  7 41  1  0
  7 42  1  0
  8 43  1  0
  8 44  1  0
  9 45  1  0
  9 46  1  0
 10 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 12 51  1  0
 12 52  1  0
 13 53  1  0
 14 54  1  0
 18 55  1  0
 19 56  1  0
 19 57  1  0
 23 58  1  0
 23 59  1  0
 25 60  1  0
 25 61  1  0
 25 62  1  0
 26 63  1  0
 26 64  1  0
 26 65  1  0
 27 66  1  0
 27 67  1  0
 27 68  1  0
M  CHG  2  22  -1  24   1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₁H₄₁NO₅

Average Molecular Weight

387.5539

Monoisotopic Molecular Weight

387.298473427

IUPAC Name

3-[(2-hydroxytetradecanoyl)oxy]-4-(trimethylazaniumyl)butanoate

Traditional Name

3-[(2-hydroxytetradecanoyl)oxy]-4-(trimethylammonio)butanoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C21H41NO5/c1-5-6-7-8-9-10-11-12-13-14-15-19(23)21(26)27-18(16-20(24)25)17-22(2,3)4/h18-19,23H,5-17H2,1-4H3

InChI Key

WWDZVVWQNWNRDM-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Acyl carnitines

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Health effect

Cancer

Breast cancer (PMID: 35710135)

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

Circulatory system disorder

Cardiac disorder

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

Renal system and urinary system

Renal disorder

Renal cell carcinoma (PMID: 35710135)

Disposition

Biological location

Cytoplasm (HMDB: HMDB0013166)
Cell membrane (HMDB: HMDB0013166)

Biofluid or Excreta

Blood (HMDB: HMDB0013166)
Urine (HMDB: HMDB0013166)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Cellular substructure

Organelle

peroxisome (PMID: 35710135)

Cell

All cells and tissues (PMID: 35710135)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0013166)

Source

Endogenous

Endogenous (HMDB: HMDB0013166)

Animal

Animal (HMDB: HMDB0013166)

Exogenous

Food

Food (HMDB: HMDB0013166)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0013166)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0013166)

Cellular process

Cell signaling (HMDB: HMDB0013166)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0013166)

Role

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	0.00018 g/L	ALOGPS
logP	-0.36	ALOGPS
logP	0.27	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	4.1	ChemAxon
pKa (Strongest Basic)	-3.8	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	129.37 m³·mol⁻¹	ChemAxon
Polarizability	47.03 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	212.245	30932474
DeepCCS	[M-H]-	208.225	30932474
DeepCCS	[M-2H]-	244.769	30932474
DeepCCS	[M+Na]+	221.06	30932474
AllCCS	[M+H]+	209.6	32859911
AllCCS	[M+H-H2O]+	207.5	32859911
AllCCS	[M+NH4]+	211.4	32859911
AllCCS	[M+Na]+	212.0	32859911
AllCCS	[M-H]-	205.5	32859911
AllCCS	[M+Na-2H]-	206.8	32859911
AllCCS	[M+HCOO]-	208.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Hydroxymyristoylcarnitine	CCCCCCCCCCCCC(O)C(=O)OC(CC([O-])=O)C[N+](C)(C)C	3132.9	Standard polar	33892256
2-Hydroxymyristoylcarnitine	CCCCCCCCCCCCC(O)C(=O)OC(CC([O-])=O)C[N+](C)(C)C	2368.8	Standard non polar	33892256
2-Hydroxymyristoylcarnitine	CCCCCCCCCCCCC(O)C(=O)OC(CC([O-])=O)C[N+](C)(C)C	2565.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Hydroxymyristoylcarnitine,1TMS,isomer #1	CCCCCCCCCCCCC(O[Si](C)(C)C)C(=O)OC(CC(=O)[O-])C[N+](C)(C)C	2566.2	Semi standard non polar	33892256
2-Hydroxymyristoylcarnitine,1TBDMS,isomer #1	CCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)C(=O)OC(CC(=O)[O-])C[N+](C)(C)C	2794.0	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 - 2-Hydroxymyristoylcarnitine GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9210000000-760f1ccd251ebb1bd6ef	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxymyristoylcarnitine 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 - 2-Hydroxymyristoylcarnitine 10V, Positive-QTOF	splash10-000i-0009000000-25880a3b3db50968190f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxymyristoylcarnitine 20V, Positive-QTOF	splash10-000i-9005000000-00237239bef4b8d45e6e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxymyristoylcarnitine 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

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	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

FDB029320

KNApSAcK ID

Not Available

Chemspider ID

35032586

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481642

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

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
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 ]
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Showing metabocard for 2-Hydroxymyristoylcarnitine (HMDB0013166)

MOL for HMDB0013166 (2-Hydroxymyristoylcarnitine)

3D MOL for HMDB0013166 (2-Hydroxymyristoylcarnitine)

3D SDF for HMDB0013166 (2-Hydroxymyristoylcarnitine)

3D-SDF for HMDB0013166 (2-Hydroxymyristoylcarnitine)

PDB for HMDB0013166 (2-Hydroxymyristoylcarnitine)

3D PDB for HMDB0013166 (2-Hydroxymyristoylcarnitine)

SMILES for HMDB0013166 (2-Hydroxymyristoylcarnitine)

INCHI for HMDB0013166 (2-Hydroxymyristoylcarnitine)

Structure for HMDB0013166 (2-Hydroxymyristoylcarnitine)

3D Structure for HMDB0013166 (2-Hydroxymyristoylcarnitine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra