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Showing metabocard for O-Palmitoleoylcarnitine (HMDB0240782)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2021-02-24 01:48:43 UTC
Update Date2022-10-24 19:44:18 UTC
HMDB IDHMDB0240782
Secondary Accession NumbersNone
Metabolite Identification
Common NameO-Palmitoleoylcarnitine
DescriptionO-Palmitoleoylcarnitine is an acylcarnitine. More specifically, it is an palmitoleic 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. O-Palmitoleoylcarnitine is therefore classified as a long chain AC. As a long-chain acylcarnitine O-Palmitoleoylcarnitine 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 O-Palmitoleoylcarnitine is elevated in the blood or plasma of individuals with children obesity (PMID: 23108202 ). It is also decreased in the blood or plasma of individuals with familial Mediterranean fever (PMID: 29900937 ). 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
Data?1614133323
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0240782 (O-Palmitoleoylcarnitine)


  Mrv1652302242102482D          

 30 29  0  0  0  0            999 V2000
    6.3789    7.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947    1.2079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2697    2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9197    2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    6.9829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    6.5704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    5.7454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    5.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    4.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5224    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2368    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802    4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947    4.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947    2.0329    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   12.0947    5.3329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8092    4.0954    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    9.9513    4.0954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5211    4.5079    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5211    2.8579    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
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  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  2  0  0  0  0
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 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
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 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 21 19  1  0  0  0  0
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 22 19  1  0  0  0  0
 23 18  1  0  0  0  0
 24  2  1  0  0  0  0
 24  3  1  0  0  0  0
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 28 21  1  0  0  0  0
 28 23  1  0  0  0  0
 29 10  1  0  0  0  0
 30 11  1  0  0  0  0
M  CHG  2  24   1  26  -1
M  END
Download

3D MOL for HMDB0240782 (O-Palmitoleoylcarnitine)

HMDB0240782
     RDKit          3D
O-Palmitoleoylcarnitine
 71 70  0  0  0  0  0  0  0  0999 V2000
   -8.3679   -2.9136    0.8550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9627   -2.1095    2.0823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8829   -0.6692    1.6585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8554   -0.5329    0.5515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4893   -0.9525    0.9452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5388   -0.7830   -0.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4826    0.6174   -0.6555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4027    1.3370   -0.6442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0928    0.8596   -0.2164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1114    0.9688   -1.3623 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1802    2.5315   -0.7168 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3082    1.1564   -0.1992 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7554    0.8384    0.8769 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0283    0.1724   -0.8603 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1967   -1.1570   -0.4323 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6138   -2.0866   -1.4773 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7280   -3.5119   -1.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2253   -3.8721   -0.0401 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2684   -4.5172   -1.9922 O   0  0  0  0  0  1  0  0  0  0  0  0
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    6.3327   -0.5144    0.6442 N   0  0  0  0  0  4  0  0  0  0  0  0
    7.7153   -1.0230    0.7671 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7823   -0.6368    1.9835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1435   -3.6429    1.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.4380   -1.9991    1.3019 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5932   -1.2859   -0.0525 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4905    2.3717   -0.9713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0390   -0.1920    0.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7443    1.4574    0.6654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4309    0.3221   -2.2199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0992    0.6031   -1.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2974    2.4030   -2.6636 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7730    1.7846    0.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9324    3.9759   -1.5912 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5687    2.2616   -2.1102 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4635    3.2038    0.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7076   -1.3988    0.5092 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5399   -1.8743   -1.6370 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1503   -1.8557   -2.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.1175   -1.0774   -1.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6544   -1.9326    1.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0503   -1.2232   -0.2638 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3305   -0.2234    1.2676 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5215    1.2409    0.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1610    1.0931   -0.7644 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9098    1.5166    0.9956 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5936   -0.5249    2.7535 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2778   -1.5894    2.1696 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0927    0.2122    2.1638 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
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  5  6  1  0
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  7  8  2  0
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 18 19  1  0
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 20 21  1  0
 21 22  2  0
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 19 24  1  0
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  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  0
  8 43  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  0
 10 47  1  0
 11 48  1  0
 11 49  1  0
 12 50  1  0
 12 51  1  0
 13 52  1  0
 13 53  1  0
 14 54  1  0
 14 55  1  0
 15 56  1  0
 15 57  1  0
 19 58  1  0
 20 59  1  0
 20 60  1  0
 24 61  1  0
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 26 63  1  0
 26 64  1  0
 26 65  1  0
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 27 67  1  0
 27 68  1  0
 28 69  1  0
 28 70  1  0
 28 71  1  0
M  CHG  2  23  -1  25   1
M  END
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3D SDF for HMDB0240782 (O-Palmitoleoylcarnitine)


  Mrv1652302242102482D          

 30 29  0  0  0  0            999 V2000
    6.3789    7.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947    1.2079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2697    2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9197    2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    6.9829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    6.5704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    5.7454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    5.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    4.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5224    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2368    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802    4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947    4.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947    2.0329    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   12.0947    5.3329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8092    4.0954    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    9.9513    4.0954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5211    4.5079    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5211    2.8579    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  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  1  0  0  0  0
 11 10  2  0  0  0  0
 12 11  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
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 21 19  1  0  0  0  0
 21 20  1  0  0  0  0
 22 19  1  0  0  0  0
 23 18  1  0  0  0  0
 24  2  1  0  0  0  0
 24  3  1  0  0  0  0
 24  4  1  0  0  0  0
 24 20  1  0  0  0  0
 25 22  2  0  0  0  0
 26 22  1  0  0  0  0
 27 23  2  0  0  0  0
 28 21  1  0  0  0  0
 28 23  1  0  0  0  0
 29 10  1  0  0  0  0
 30 11  1  0  0  0  0
M  CHG  2  24   1  26  -1
M  END
> <DATABASE_ID>
HMDB0240782

> <DATABASE_NAME>
hmdb

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

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

> <INCHI_KEY>
JFAGPSOZZSTLRF-KHPPLWFESA-N

> <FORMULA>
C23H43NO4

> <MOLECULAR_WEIGHT>
397.6

> <EXACT_MASS>
397.319208869

$$$$
Download

3D-SDF for HMDB0240782 (O-Palmitoleoylcarnitine)

HMDB0240782
     RDKit          3D
O-Palmitoleoylcarnitine
 71 70  0  0  0  0  0  0  0  0999 V2000
   -8.3679   -2.9136    0.8550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9627   -2.1095    2.0823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8829   -0.6692    1.6585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8554   -0.5329    0.5515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4893   -0.9525    0.9452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5388   -0.7830   -0.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4826    0.6174   -0.6555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4027    1.3370   -0.6442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0928    0.8596   -0.2164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1114    0.9688   -1.3623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9987    2.3972   -1.7993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5381    3.2581   -0.6698 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8043    2.8198   -0.1511 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8393    2.9149   -1.2388 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1802    2.5315   -0.7168 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3082    1.1564   -0.1992 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7554    0.8384    0.8769 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0283    0.1724   -0.8603 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1967   -1.1570   -0.4323 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6138   -2.0866   -1.4773 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7280   -3.5119   -1.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2253   -3.8721   -0.0401 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2684   -4.5172   -1.9922 O   0  0  0  0  0  1  0  0  0  0  0  0
    5.6931   -1.3692   -0.3013 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3327   -0.5144    0.6442 N   0  0  0  0  0  4  0  0  0  0  0  0
    7.7153   -1.0230    0.7671 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4582    0.8612    0.2573 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7823   -0.6368    1.9835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1435   -3.6429    1.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8063   -2.2606    0.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4996   -3.5132    0.4679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7654   -2.2514    2.8636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9944   -2.4343    2.4735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6622   -0.0067    2.5097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8724   -0.3156    1.2472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8325    0.5538    0.2618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1856   -1.0575   -0.3683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4380   -1.9991    1.3019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1197   -0.3251    1.7881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5932   -1.2859   -0.0525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0175   -1.4069   -1.0758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4278    1.0663   -1.0083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4905    2.3717   -0.9713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0390   -0.1920    0.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7443    1.4574    0.6654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4309    0.3221   -2.2199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0992    0.6031   -1.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9774    2.8010   -2.1725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2974    2.4030   -2.6636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2825    3.3294    0.1510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3701    4.3121   -1.0736 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0959    3.4546    0.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7730    1.7846    0.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9324    3.9759   -1.5912 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5687    2.2616   -2.1102 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4635    3.2038    0.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9536    2.7527   -1.4996 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7076   -1.3988    0.5092 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5399   -1.8743   -1.6370 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1503   -1.8557   -2.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9887   -2.4088   -0.1339 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1175   -1.0774   -1.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6544   -1.9326    1.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0503   -1.2232   -0.2638 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3305   -0.2234    1.2676 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5215    1.2409    0.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1610    1.0931   -0.7644 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9098    1.5166    0.9956 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5936   -0.5249    2.7535 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2778   -1.5894    2.1696 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0927    0.2122    2.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 19 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 25 28  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  0
  8 43  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  0
 10 47  1  0
 11 48  1  0
 11 49  1  0
 12 50  1  0
 12 51  1  0
 13 52  1  0
 13 53  1  0
 14 54  1  0
 14 55  1  0
 15 56  1  0
 15 57  1  0
 19 58  1  0
 20 59  1  0
 20 60  1  0
 24 61  1  0
 24 62  1  0
 26 63  1  0
 26 64  1  0
 26 65  1  0
 27 66  1  0
 27 67  1  0
 27 68  1  0
 28 69  1  0
 28 70  1  0
 28 71  1  0
M  CHG  2  23  -1  25   1
M  END
Download

PDB for HMDB0240782 (O-Palmitoleoylcarnitine)

HEADER    PROTEIN                                 24-FEB-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-21         0                                  
HETATM    1  C   UNK     0      11.907  14.575   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      22.577   2.255   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      21.037   3.795   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      24.117   3.795   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.907  13.035   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.574  12.265   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.574  10.725   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.240   9.955   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.240   8.415   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.906   7.645   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.906   6.105   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.240   5.335   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.574   6.105   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.907   5.335   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.241   6.105   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.575   5.335   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      15.908   6.105   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.242   5.335   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      21.243   7.645   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      22.577   5.335   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      21.243   6.105   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      22.577   8.415   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      18.576   6.105   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0      22.577   3.795   0.000  0.00  0.00           N+1
HETATM   25  O   UNK     0      22.577   9.955   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      23.910   7.645   0.000  0.00  0.00           O-1
HETATM   27  O   UNK     0      18.576   7.645   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      19.909   5.335   0.000  0.00  0.00           O+0
HETATM   29  H   UNK     0       6.573   8.415   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0       6.573   5.335   0.000  0.00  0.00           H+0
CONECT    1    5                                                            
CONECT    2   24                                                            
CONECT    3   24                                                            
CONECT    4   24                                                            
CONECT    5    1    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   29                                                  
CONECT   11   10   12   30                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   23                                                       
CONECT   19   21   22                                                       
CONECT   20   21   24                                                       
CONECT   21   19   20   28                                                  
CONECT   22   19   25   26                                                  
CONECT   23   18   27   28                                                  
CONECT   24    2    3    4   20                                             
CONECT   25   22                                                            
CONECT   26   22                                                            
CONECT   27   23                                                            
CONECT   28   21   23                                                       
CONECT   29   10                                                            
CONECT   30   11                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   58    0
END
Download

3D PDB for HMDB0240782 (O-Palmitoleoylcarnitine)

COMPND    HMDB0240782
HETATM    1  C1  UNL     1      -8.368  -2.914   0.855  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.963  -2.109   2.082  1.00  0.00           C  
HETATM    3  C3  UNL     1      -7.883  -0.669   1.658  1.00  0.00           C  
HETATM    4  C4  UNL     1      -6.855  -0.533   0.551  1.00  0.00           C  
HETATM    5  C5  UNL     1      -5.489  -0.952   0.945  1.00  0.00           C  
HETATM    6  C6  UNL     1      -4.539  -0.783  -0.238  1.00  0.00           C  
HETATM    7  C7  UNL     1      -4.483   0.617  -0.655  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.403   1.337  -0.644  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.093   0.860  -0.216  1.00  0.00           C  
HETATM   10  C10 UNL     1      -1.111   0.969  -1.362  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.999   2.397  -1.799  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.538   3.258  -0.670  1.00  0.00           C  
HETATM   13  C13 UNL     1       0.804   2.820  -0.151  1.00  0.00           C  
HETATM   14  C14 UNL     1       1.839   2.915  -1.239  1.00  0.00           C  
HETATM   15  C15 UNL     1       3.180   2.531  -0.717  1.00  0.00           C  
HETATM   16  C16 UNL     1       3.308   1.156  -0.199  1.00  0.00           C  
HETATM   17  O1  UNL     1       2.755   0.838   0.877  1.00  0.00           O  
HETATM   18  O2  UNL     1       4.028   0.172  -0.860  1.00  0.00           O  
HETATM   19  C17 UNL     1       4.197  -1.157  -0.432  1.00  0.00           C  
HETATM   20  C18 UNL     1       3.614  -2.087  -1.477  1.00  0.00           C  
HETATM   21  C19 UNL     1       3.728  -3.512  -1.115  1.00  0.00           C  
HETATM   22  O3  UNL     1       4.225  -3.872  -0.040  1.00  0.00           O  
HETATM   23  O4  UNL     1       3.268  -4.517  -1.992  1.00  0.00           O1-
HETATM   24  C20 UNL     1       5.693  -1.369  -0.301  1.00  0.00           C  
HETATM   25  N1  UNL     1       6.333  -0.514   0.644  1.00  0.00           N1+
HETATM   26  C21 UNL     1       7.715  -1.023   0.767  1.00  0.00           C  
HETATM   27  C22 UNL     1       6.458   0.861   0.257  1.00  0.00           C  
HETATM   28  C23 UNL     1       5.782  -0.637   1.984  1.00  0.00           C  
HETATM   29  H1  UNL     1      -9.143  -3.643   1.138  1.00  0.00           H  
HETATM   30  H2  UNL     1      -8.806  -2.261   0.071  1.00  0.00           H  
HETATM   31  H3  UNL     1      -7.500  -3.513   0.468  1.00  0.00           H  
HETATM   32  H4  UNL     1      -8.765  -2.251   2.864  1.00  0.00           H  
HETATM   33  H5  UNL     1      -6.994  -2.434   2.473  1.00  0.00           H  
HETATM   34  H6  UNL     1      -7.662  -0.007   2.510  1.00  0.00           H  
HETATM   35  H7  UNL     1      -8.872  -0.316   1.247  1.00  0.00           H  
HETATM   36  H8  UNL     1      -6.833   0.554   0.262  1.00  0.00           H  
HETATM   37  H9  UNL     1      -7.186  -1.058  -0.368  1.00  0.00           H  
HETATM   38  H10 UNL     1      -5.438  -1.999   1.302  1.00  0.00           H  
HETATM   39  H11 UNL     1      -5.120  -0.325   1.788  1.00  0.00           H  
HETATM   40  H12 UNL     1      -3.593  -1.286  -0.052  1.00  0.00           H  
HETATM   41  H13 UNL     1      -5.018  -1.407  -1.076  1.00  0.00           H  
HETATM   42  H14 UNL     1      -5.428   1.066  -1.008  1.00  0.00           H  
HETATM   43  H15 UNL     1      -3.490   2.372  -0.971  1.00  0.00           H  
HETATM   44  H16 UNL     1      -2.039  -0.192   0.124  1.00  0.00           H  
HETATM   45  H17 UNL     1      -1.744   1.457   0.665  1.00  0.00           H  
HETATM   46  H18 UNL     1      -1.431   0.322  -2.220  1.00  0.00           H  
HETATM   47  H19 UNL     1      -0.099   0.603  -1.103  1.00  0.00           H  
HETATM   48  H20 UNL     1      -1.977   2.801  -2.173  1.00  0.00           H  
HETATM   49  H21 UNL     1      -0.297   2.403  -2.664  1.00  0.00           H  
HETATM   50  H22 UNL     1      -1.282   3.329   0.151  1.00  0.00           H  
HETATM   51  H23 UNL     1      -0.370   4.312  -1.074  1.00  0.00           H  
HETATM   52  H24 UNL     1       1.096   3.455   0.732  1.00  0.00           H  
HETATM   53  H25 UNL     1       0.773   1.785   0.258  1.00  0.00           H  
HETATM   54  H26 UNL     1       1.932   3.976  -1.591  1.00  0.00           H  
HETATM   55  H27 UNL     1       1.569   2.262  -2.110  1.00  0.00           H  
HETATM   56  H28 UNL     1       3.464   3.204   0.143  1.00  0.00           H  
HETATM   57  H29 UNL     1       3.954   2.753  -1.500  1.00  0.00           H  
HETATM   58  H30 UNL     1       3.708  -1.399   0.509  1.00  0.00           H  
HETATM   59  H31 UNL     1       2.540  -1.874  -1.637  1.00  0.00           H  
HETATM   60  H32 UNL     1       4.150  -1.856  -2.423  1.00  0.00           H  
HETATM   61  H33 UNL     1       5.989  -2.409  -0.134  1.00  0.00           H  
HETATM   62  H34 UNL     1       6.118  -1.077  -1.312  1.00  0.00           H  
HETATM   63  H35 UNL     1       7.654  -1.933   1.380  1.00  0.00           H  
HETATM   64  H36 UNL     1       8.050  -1.223  -0.264  1.00  0.00           H  
HETATM   65  H37 UNL     1       8.331  -0.223   1.268  1.00  0.00           H  
HETATM   66  H38 UNL     1       7.522   1.241   0.345  1.00  0.00           H  
HETATM   67  H39 UNL     1       6.161   1.093  -0.764  1.00  0.00           H  
HETATM   68  H40 UNL     1       5.910   1.517   0.996  1.00  0.00           H  
HETATM   69  H41 UNL     1       6.594  -0.525   2.754  1.00  0.00           H  
HETATM   70  H42 UNL     1       5.278  -1.589   2.170  1.00  0.00           H  
HETATM   71  H43 UNL     1       5.093   0.212   2.164  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3   32   33
CONECT    3    4   34   35
CONECT    4    5   36   37
CONECT    5    6   38   39
CONECT    6    7   40   41
CONECT    7    8    8   42
CONECT    8    9   43
CONECT    9   10   44   45
CONECT   10   11   46   47
CONECT   11   12   48   49
CONECT   12   13   50   51
CONECT   13   14   52   53
CONECT   14   15   54   55
CONECT   15   16   56   57
CONECT   16   17   17   18
CONECT   18   19
CONECT   19   20   24   58
CONECT   20   21   59   60
CONECT   21   22   22   23
CONECT   24   25   61   62
CONECT   25   26   27   28
CONECT   26   63   64   65
CONECT   27   66   67   68
CONECT   28   69   70   71
END
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SMILES for HMDB0240782 (O-Palmitoleoylcarnitine)

[H]\C(CCCCCC)=C(/[H])CCCCCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C
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INCHI for HMDB0240782 (O-Palmitoleoylcarnitine)

InChI=1S/C23H43NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(27)28-21(19-22(25)26)20-24(2,3)4/h10-11,21H,5-9,12-20H2,1-4H3/b11-10-
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View in JSmolView Stereo Labels
Synonyms
ValueSource
(9Z)-Hexadec-9-enoylcarnitineChEBI
3-[(9Z)-Hexadec-9-enoyloxy]-4-(trimethylammonio)butanoateChEBI
cis-9-HexadecenoylcarnitineChEBI
3-[(9Z)-Hexadec-9-enoyloxy]-4-(trimethylammonio)butanoic acidGenerator
Chemical FormulaC23H43NO4
Average Molecular Weight397.6
Monoisotopic Molecular Weight397.319208869
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILES
[H]\C(CCCCCC)=C(/[H])CCCCCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C
InChI Identifier
InChI=1S/C23H43NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(27)28-21(19-22(25)26)20-24(2,3)4/h10-11,21H,5-9,12-20H2,1-4H3/b11-10-
InChI KeyJFAGPSOZZSTLRF-KHPPLWFESA-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentAcyl carnitines
Alternative Parents
Substituents
  • Acyl-carnitine
  • Dicarboxylic acid or derivatives
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Carboxylic acid ester
  • Carboxylic acid salt
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic salt
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Health effect
Disposition
Biological locationSource
ProcessNot Available
Role
Biological roleIndustrial application
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+227.50630932474
DeepCCS[M-H]-225.14830932474
DeepCCS[M-2H]-258.39230932474
DeepCCS[M+Na]+234.89830932474
AllCCS[M+H]+213.232859911
AllCCS[M+H-H2O]+211.232859911
AllCCS[M+NH4]+215.132859911
AllCCS[M+Na]+215.632859911
AllCCS[M-H]-206.532859911
AllCCS[M+Na-2H]-208.532859911
AllCCS[M+HCOO]-210.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
O-Palmitoleoylcarnitine[H]\C(CCCCCC)=C(/[H])CCCCCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C3140.9Standard polar33892256
O-Palmitoleoylcarnitine[H]\C(CCCCCC)=C(/[H])CCCCCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C2409.5Standard non polar33892256
O-Palmitoleoylcarnitine[H]\C(CCCCCC)=C(/[H])CCCCCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C2678.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - O-Palmitoleoylcarnitine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Palmitoleoylcarnitine 10V, Positive-QTOFsplash10-0002-0009000000-78c0db1f7d539241ca802021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Palmitoleoylcarnitine 20V, Positive-QTOFsplash10-000j-9005000000-9978022cc1181ffa34522021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Palmitoleoylcarnitine 40V, Positive-QTOFsplash10-000i-9000000000-e9262cbaff8cb4ad0ba62021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID28639183
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound71464547
PDB IDNot Available
ChEBI ID73066
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Wahl S, Yu Z, Kleber M, Singmann P, Holzapfel C, He Y, Mittelstrass K, Polonikov A, Prehn C, Romisch-Margl W, Adamski J, Suhre K, Grallert H, Illig T, Wang-Sattler R, Reinehr T: Childhood obesity is associated with changes in the serum metabolite profile. Obes Facts. 2012;5(5):660-70. doi: 10.1159/000343204. Epub 2012 Oct 4. [PubMed:23108202 ]
  2. Sud M, Fahy E, Cotter D, Brown A, Dennis EA, Glass CK, Merrill AH Jr, Murphy RC, Raetz CR, Russell DW, Subramaniam S: LMSD: LIPID MAPS structure database. Nucleic Acids Res. 2007 Jan;35(Database issue):D527-32. doi: 10.1093/nar/gkl838. Epub 2006 Nov 10. [PubMed:17098933 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. Kiykim E, Aktuglu Zeybek AC, Barut K, Zubarioglu T, Cansever MS, Alsancak S, Kasapcopur O: Screening of Free Carnitine and Acylcarnitine Status in Children With Familial Mediterranean Fever. Arch Rheumatol. 2016 Mar 10;31(2):133-138. doi: 10.5606/ArchRheumatol.2016.5696. eCollection 2016 Jun. [PubMed:29900937 ]
  9. 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 ]