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Showing metabocard for O-Palmitoylcarnitine (HMDB0240783)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2021-02-24 01:48:53 UTC
Update Date2022-10-24 19:44:18 UTC
HMDB IDHMDB0240783
Secondary Accession NumbersNone
Metabolite Identification
Common NameO-Palmitoylcarnitine
DescriptionO-Palmitoylcarnitine is an acylcarnitine. More specifically, it is an palmitic 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-Palmitoylcarnitine is therefore classified as a long chain AC. As a long-chain acylcarnitine O-Palmitoylcarnitine 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-Palmitoylcarnitine is elevated in the blood or plasma of individuals with very long chain acyl-CoA dehydrogenase (VLCAD) deficiency (PMID: 9034211 ), sleep deprivation (PMID: 31419538 ), carnitine palmitoyl transferase 2 deficiency (PMID: 15653102 ), carnitine-acylcarnitine translocase deficiency (PMID: 12403251 ), type 2 diabetes mellitus (PMID: 27694567 , PMID: 24837145 , PMID: 20111019 ), non-alcoholic fatty liver disease (PMID: 27211699 ), obesity (PMID: 20111019 ), pulmonary arterial hypertension (PMID: 27006481 ), chronic heart failure (PMID: 22622056 ), cardiovascular mortality in chronic kidney disease (PMID: 24308938 ), diastolic heart failure (PMID: 26010610 , PMID: 27473038 ), and systolic heart failure (PMID: 27473038 ). It is also decreased in the blood or plasma of individuals with intracerebral hemorrhage (PMID: 29265114 ), carnitine palmitoyl transferase 1A deficiency (PMID: 11568084 ), and psoriasis (PMID: 33391503 ). It is found to be increased in feces of patients with cirrhosis (PMID: 23384618 ). 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?1614132698
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0240783 (O-Palmitoylcarnitine)


  Mrv1652302242102482D          

 28 27  0  0  0  0            999 V2000
    7.2336    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0940    3.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2690    4.1763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9190    4.1763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9480    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6625    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3770    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0914    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8059    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5204    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2349    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9493    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6638    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3783    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0927    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8072    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5217    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2362    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3796    6.2388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0940    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3796    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0940    6.6513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9506    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0940    4.1763    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   20.0940    7.4763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8085    6.2388    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   17.9506    6.2388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6651    5.0013    0.0000 O   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  1  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
M  CHG  2  24   1  26  -1
M  END
Download

3D MOL for HMDB0240783 (O-Palmitoylcarnitine)

HMDB0240783
     RDKit          3D
O-Palmitoylcarnitine
 73 72  0  0  0  0  0  0  0  0999 V2000
   10.1717   -0.0319    1.4314 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0947    0.8000    0.7247 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1670    0.4984   -0.7381 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1752    1.2402   -1.5762 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7274    0.9602   -1.2071 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3912   -0.4877   -1.3167 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9024   -0.6822   -0.9889 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5635   -0.1960    0.3618 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2308   -0.4420    0.8929 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9616    0.0355    0.3047 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6294   -0.4818   -1.0388 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2809   -0.1632   -1.6047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9302   -0.7724   -1.0569 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.1558    1.6802    0.8085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9666    2.3888    0.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.0613    3.0717    1.0656 O   0  0  0  0  0  1  0  0  0  0  0  0
   -7.1514   -0.6387    0.8679 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.6709    0.1562   -0.8338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2087   -1.6326    0.5564 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7537   -0.6387    0.6987 H   0  0  0  0  0  0  0  0  0  0  0  0
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    9.6935   -0.7471    2.1396 H   0  0  0  0  0  0  0  0  0  0  0  0
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    8.0956    0.5015    1.1099 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9639   -0.5975   -0.8680 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.6316    1.2481   -0.1347 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0938    1.5924   -1.8284 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5297   -0.8749   -2.3370 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0133   -1.0734   -0.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4241   -0.0302   -1.7633 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6425   -1.7447   -1.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7547    0.9257    0.4573 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3092   -0.6510    1.0990 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1871   -0.0747    2.0031 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1564   -1.5771    1.0924 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0969    1.2088    0.2025 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1244    0.0109    1.0023 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3993   -0.0386   -1.7591 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8437   -1.5956   -1.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1888    0.9709   -1.7053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3437   -0.4502   -2.7161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9109   -1.9008   -1.2444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7875   -0.3847   -1.7122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5102   -1.2278    0.9601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1497    0.4283    0.7191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6360   -1.0659    1.8947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5390   -2.2987    0.6323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9343    0.1909   -0.7509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0866    2.1615    0.4903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0951    1.7704    1.9106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0746   -0.6209    1.9996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8638   -1.6975    0.6040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3180    1.4988    1.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3756    0.5707    2.4071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9965    0.0655    1.9270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5261   -0.3465   -1.3567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8082    0.0377   -1.5177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9520    1.2520   -0.8457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8906   -2.2371    1.4296 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2801   -1.3986    0.5320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9793   -2.2228   -0.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 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
  7 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  0
  9 47  1  0
 10 48  1  0
 10 49  1  0
 11 50  1  0
 11 51  1  0
 12 52  1  0
 12 53  1  0
 13 54  1  0
 13 55  1  0
 14 56  1  0
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 15 58  1  0
 15 59  1  0
 19 60  1  0
 20 61  1  0
 20 62  1  0
 24 63  1  0
 24 64  1  0
 26 65  1  0
 26 66  1  0
 26 67  1  0
 27 68  1  0
 27 69  1  0
 27 70  1  0
 28 71  1  0
 28 72  1  0
 28 73  1  0
M  CHG  2  23  -1  25   1
M  END
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3D SDF for HMDB0240783 (O-Palmitoylcarnitine)


  Mrv1652302242102482D          

 28 27  0  0  0  0            999 V2000
    7.2336    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0940    3.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2690    4.1763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9190    4.1763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9480    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6625    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3770    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0914    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8059    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5204    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2349    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9493    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6638    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3783    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0927    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8072    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5217    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2362    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3796    6.2388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0940    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3796    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0940    6.6513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9506    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0940    4.1763    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   20.0940    7.4763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8085    6.2388    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   17.9506    6.2388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6651    5.0013    0.0000 O   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  1  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
M  CHG  2  24   1  26  -1
M  END
> <DATABASE_ID>
HMDB0240783

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C23H45NO4/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/h21H,5-20H2,1-4H3

> <INCHI_KEY>
XOMRRQXKHMYMOC-UHFFFAOYSA-N

> <FORMULA>
C23H45NO4

> <MOLECULAR_WEIGHT>
399.616

> <EXACT_MASS>
399.334858933

$$$$
Download

3D-SDF for HMDB0240783 (O-Palmitoylcarnitine)

HMDB0240783
     RDKit          3D
O-Palmitoylcarnitine
 73 72  0  0  0  0  0  0  0  0999 V2000
   10.1717   -0.0319    1.4314 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0947    0.8000    0.7247 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1670    0.4984   -0.7381 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1752    1.2402   -1.5762 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7274    0.9602   -1.2071 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3912   -0.4877   -1.3167 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9024   -0.6822   -0.9889 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5635   -0.1960    0.3618 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2308   -0.4420    0.8929 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9616    0.0355    0.3047 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6294   -0.4818   -1.0388 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2809   -0.1632   -1.6047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9302   -0.7724   -1.0569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2462   -0.5816    0.3588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5742   -1.1917    0.8125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7572   -0.6853    0.1427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9351   -0.5610   -1.0904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8583   -0.2707    0.9154 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0619    0.2355    0.3586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1558    1.6802    0.8085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9666    2.3888    0.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7258    2.3937   -0.9884 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0613    3.0717    1.0656 O   0  0  0  0  0  1  0  0  0  0  0  0
   -7.1514   -0.6387    0.8679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4749   -0.3544    0.4762 N   0  0  0  0  0  4  0  0  0  0  0  0
   -9.0672    0.4946    1.5197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6709    0.1562   -0.8338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2087   -1.6326    0.5564 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7537   -0.6387    0.6987 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8491    0.6102    2.0275 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6935   -0.7471    2.1396 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2912    1.8575    0.9819 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0956    0.5015    1.1099 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9639   -0.5975   -0.8680 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1899    0.7460   -1.1443 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3226    2.3280   -1.3861 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3654    1.0245   -2.6429 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6316    1.2481   -0.1347 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0938    1.5924   -1.8284 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5297   -0.8749   -2.3370 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0133   -1.0734   -0.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4241   -0.0302   -1.7633 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6425   -1.7447   -1.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7547    0.9257    0.4573 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3092   -0.6510    1.0990 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1871   -0.0747    2.0031 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1564   -1.5771    1.0924 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0969    1.2088    0.2025 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1244    0.0109    1.0023 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3993   -0.0386   -1.7591 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8437   -1.5956   -1.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1888    0.9709   -1.7053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3437   -0.4502   -2.7161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9109   -1.9008   -1.2444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7875   -0.3847   -1.7122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5102   -1.2278    0.9601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1497    0.4283    0.7191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6360   -1.0659    1.8947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5390   -2.2987    0.6323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9343    0.1909   -0.7509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0866    2.1615    0.4903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0951    1.7704    1.9106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0746   -0.6209    1.9996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8638   -1.6975    0.6040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3180    1.4988    1.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3756    0.5707    2.4071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9965    0.0655    1.9270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5261   -0.3465   -1.3567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8082    0.0377   -1.5177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9520    1.2520   -0.8457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8906   -2.2371    1.4296 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2801   -1.3986    0.5320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9793   -2.2228   -0.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 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
  7 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  0
  9 47  1  0
 10 48  1  0
 10 49  1  0
 11 50  1  0
 11 51  1  0
 12 52  1  0
 12 53  1  0
 13 54  1  0
 13 55  1  0
 14 56  1  0
 14 57  1  0
 15 58  1  0
 15 59  1  0
 19 60  1  0
 20 61  1  0
 20 62  1  0
 24 63  1  0
 24 64  1  0
 26 65  1  0
 26 66  1  0
 26 67  1  0
 27 68  1  0
 27 69  1  0
 27 70  1  0
 28 71  1  0
 28 72  1  0
 28 73  1  0
M  CHG  2  23  -1  25   1
M  END
Download

PDB for HMDB0240783 (O-Palmitoylcarnitine)

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      13.503   9.336   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      37.509   6.256   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      35.969   7.796   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      39.049   7.796   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.836  10.106   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.170   9.336   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.504  10.106   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      18.837   9.336   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      20.171  10.106   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.505   9.336   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      22.838  10.106   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      24.172   9.336   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      25.506  10.106   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      26.839   9.336   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      28.173  10.106   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      29.507   9.336   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      30.840  10.106   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      32.174   9.336   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      36.175  11.646   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      37.509   9.336   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      36.175  10.106   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      37.509  12.416   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      33.508  10.106   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0      37.509   7.796   0.000  0.00  0.00           N+1
HETATM   25  O   UNK     0      37.509  13.956   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      38.843  11.646   0.000  0.00  0.00           O-1
HETATM   27  O   UNK     0      33.508  11.646   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      34.842   9.336   0.000  0.00  0.00           O+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                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   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                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   54    0
END
Download

3D PDB for HMDB0240783 (O-Palmitoylcarnitine)

COMPND    HMDB0240783
HETATM    1  C1  UNL     1      10.172  -0.032   1.431  1.00  0.00           C  
HETATM    2  C2  UNL     1       9.095   0.800   0.725  1.00  0.00           C  
HETATM    3  C3  UNL     1       9.167   0.498  -0.738  1.00  0.00           C  
HETATM    4  C4  UNL     1       8.175   1.240  -1.576  1.00  0.00           C  
HETATM    5  C5  UNL     1       6.727   0.960  -1.207  1.00  0.00           C  
HETATM    6  C6  UNL     1       6.391  -0.488  -1.317  1.00  0.00           C  
HETATM    7  C7  UNL     1       4.902  -0.682  -0.989  1.00  0.00           C  
HETATM    8  C8  UNL     1       4.563  -0.196   0.362  1.00  0.00           C  
HETATM    9  C9  UNL     1       3.231  -0.442   0.893  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.962   0.036   0.305  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.629  -0.482  -1.039  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.281  -0.163  -1.605  1.00  0.00           C  
HETATM   13  C13 UNL     1      -0.930  -0.772  -1.057  1.00  0.00           C  
HETATM   14  C14 UNL     1      -1.246  -0.582   0.359  1.00  0.00           C  
HETATM   15  C15 UNL     1      -2.574  -1.192   0.812  1.00  0.00           C  
HETATM   16  C16 UNL     1      -3.757  -0.685   0.143  1.00  0.00           C  
HETATM   17  O1  UNL     1      -3.935  -0.561  -1.090  1.00  0.00           O  
HETATM   18  O2  UNL     1      -4.858  -0.271   0.915  1.00  0.00           O  
HETATM   19  C17 UNL     1      -6.062   0.235   0.359  1.00  0.00           C  
HETATM   20  C18 UNL     1      -6.156   1.680   0.808  1.00  0.00           C  
HETATM   21  C19 UNL     1      -4.967   2.389   0.269  1.00  0.00           C  
HETATM   22  O3  UNL     1      -4.726   2.394  -0.988  1.00  0.00           O  
HETATM   23  O4  UNL     1      -4.061   3.072   1.066  1.00  0.00           O1-
HETATM   24  C20 UNL     1      -7.151  -0.639   0.868  1.00  0.00           C  
HETATM   25  N1  UNL     1      -8.475  -0.354   0.476  1.00  0.00           N1+
HETATM   26  C21 UNL     1      -9.067   0.495   1.520  1.00  0.00           C  
HETATM   27  C22 UNL     1      -8.671   0.156  -0.834  1.00  0.00           C  
HETATM   28  C23 UNL     1      -9.209  -1.633   0.556  1.00  0.00           C  
HETATM   29  H1  UNL     1      10.754  -0.639   0.699  1.00  0.00           H  
HETATM   30  H2  UNL     1      10.849   0.610   2.027  1.00  0.00           H  
HETATM   31  H3  UNL     1       9.694  -0.747   2.140  1.00  0.00           H  
HETATM   32  H4  UNL     1       9.291   1.857   0.982  1.00  0.00           H  
HETATM   33  H5  UNL     1       8.096   0.501   1.110  1.00  0.00           H  
HETATM   34  H6  UNL     1       8.964  -0.597  -0.868  1.00  0.00           H  
HETATM   35  H7  UNL     1      10.190   0.746  -1.144  1.00  0.00           H  
HETATM   36  H8  UNL     1       8.323   2.328  -1.386  1.00  0.00           H  
HETATM   37  H9  UNL     1       8.365   1.025  -2.643  1.00  0.00           H  
HETATM   38  H10 UNL     1       6.632   1.248  -0.135  1.00  0.00           H  
HETATM   39  H11 UNL     1       6.094   1.592  -1.828  1.00  0.00           H  
HETATM   40  H12 UNL     1       6.530  -0.875  -2.337  1.00  0.00           H  
HETATM   41  H13 UNL     1       7.013  -1.073  -0.600  1.00  0.00           H  
HETATM   42  H14 UNL     1       4.424  -0.030  -1.763  1.00  0.00           H  
HETATM   43  H15 UNL     1       4.643  -1.745  -1.096  1.00  0.00           H  
HETATM   44  H16 UNL     1       4.755   0.926   0.457  1.00  0.00           H  
HETATM   45  H17 UNL     1       5.309  -0.651   1.099  1.00  0.00           H  
HETATM   46  H18 UNL     1       3.187  -0.075   2.003  1.00  0.00           H  
HETATM   47  H19 UNL     1       3.156  -1.577   1.092  1.00  0.00           H  
HETATM   48  H20 UNL     1       2.097   1.209   0.203  1.00  0.00           H  
HETATM   49  H21 UNL     1       1.124   0.011   1.002  1.00  0.00           H  
HETATM   50  H22 UNL     1       2.399  -0.039  -1.759  1.00  0.00           H  
HETATM   51  H23 UNL     1       1.844  -1.596  -1.111  1.00  0.00           H  
HETATM   52  H24 UNL     1       0.189   0.971  -1.705  1.00  0.00           H  
HETATM   53  H25 UNL     1       0.344  -0.450  -2.716  1.00  0.00           H  
HETATM   54  H26 UNL     1      -0.911  -1.901  -1.244  1.00  0.00           H  
HETATM   55  H27 UNL     1      -1.787  -0.385  -1.712  1.00  0.00           H  
HETATM   56  H28 UNL     1      -0.510  -1.228   0.960  1.00  0.00           H  
HETATM   57  H29 UNL     1      -1.150   0.428   0.719  1.00  0.00           H  
HETATM   58  H30 UNL     1      -2.636  -1.066   1.895  1.00  0.00           H  
HETATM   59  H31 UNL     1      -2.539  -2.299   0.632  1.00  0.00           H  
HETATM   60  H32 UNL     1      -5.934   0.191  -0.751  1.00  0.00           H  
HETATM   61  H33 UNL     1      -7.087   2.161   0.490  1.00  0.00           H  
HETATM   62  H34 UNL     1      -6.095   1.770   1.911  1.00  0.00           H  
HETATM   63  H35 UNL     1      -7.075  -0.621   2.000  1.00  0.00           H  
HETATM   64  H36 UNL     1      -6.864  -1.698   0.604  1.00  0.00           H  
HETATM   65  H37 UNL     1      -9.318   1.499   1.125  1.00  0.00           H  
HETATM   66  H38 UNL     1      -8.376   0.571   2.407  1.00  0.00           H  
HETATM   67  H39 UNL     1      -9.997   0.066   1.927  1.00  0.00           H  
HETATM   68  H40 UNL     1      -9.526  -0.346  -1.357  1.00  0.00           H  
HETATM   69  H41 UNL     1      -7.808   0.038  -1.518  1.00  0.00           H  
HETATM   70  H42 UNL     1      -8.952   1.252  -0.846  1.00  0.00           H  
HETATM   71  H43 UNL     1      -8.891  -2.237   1.430  1.00  0.00           H  
HETATM   72  H44 UNL     1     -10.280  -1.399   0.532  1.00  0.00           H  
HETATM   73  H45 UNL     1      -8.979  -2.223  -0.353  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   42   43
CONECT    8    9   44   45
CONECT    9   10   46   47
CONECT   10   11   48   49
CONECT   11   12   50   51
CONECT   12   13   52   53
CONECT   13   14   54   55
CONECT   14   15   56   57
CONECT   15   16   58   59
CONECT   16   17   17   18
CONECT   18   19
CONECT   19   20   24   60
CONECT   20   21   61   62
CONECT   21   22   22   23
CONECT   24   25   63   64
CONECT   25   26   27   28
CONECT   26   65   66   67
CONECT   27   68   69   70
CONECT   28   71   72   73
END
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SMILES for HMDB0240783 (O-Palmitoylcarnitine)

CCCCCCCCCCCCCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C
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INCHI for HMDB0240783 (O-Palmitoylcarnitine)

InChI=1S/C23H45NO4/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/h21H,5-20H2,1-4H3
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View in JSmolView Stereo Labels
Synonyms
ValueSource
3-(Hexadecanoyloxy)-4-(trimethylammonio)butanoateChEBI
HexadecanoylcarnitineChEBI
HexadecanoylcarnitinesChEBI
O-HexadecanoylcarnitineChEBI
PalmitoylcarnitineChEBI
3-(Hexadecanoyloxy)-4-(trimethylammonio)butanoic acidGenerator
PalmitylcarnitineHMDB
Chemical FormulaC23H45NO4
Average Molecular Weight399.616
Monoisotopic Molecular Weight399.334858933
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C
InChI Identifier
InChI=1S/C23H45NO4/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/h21H,5-20H2,1-4H3
InChI KeyXOMRRQXKHMYMOC-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.
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]+214.78630932474
DeepCCS[M-H]-210.76630932474
DeepCCS[M-2H]-247.3130932474
DeepCCS[M+Na]+223.60130932474
AllCCS[M+H]+217.232859911
AllCCS[M+H-H2O]+215.232859911
AllCCS[M+NH4]+218.932859911
AllCCS[M+Na]+219.432859911
AllCCS[M-H]-210.032859911
AllCCS[M+Na-2H]-211.632859911
AllCCS[M+HCOO]-213.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
O-PalmitoylcarnitineCCCCCCCCCCCCCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C3048.2Standard polar33892256
O-PalmitoylcarnitineCCCCCCCCCCCCCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C2447.6Standard non polar33892256
O-PalmitoylcarnitineCCCCCCCCCCCCCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C2671.2Semi standard non polar33892256
Spectra

GC-MS Spectra

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

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - O-Palmitoylcarnitine 35V, Positive-QTOFsplash10-0udi-5002900000-528454bf0a9528cdeb362021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - O-Palmitoylcarnitine 35V, Negative-QTOFsplash10-0a4i-0090000000-17674390272db6ddadc62021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Palmitoylcarnitine 10V, Positive-QTOFsplash10-0udi-0000900000-b54b0a7f2164f15f15f22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Palmitoylcarnitine 20V, Positive-QTOFsplash10-0f79-9000500000-d7434e08a3e0942fa2e92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Palmitoylcarnitine 40V, Positive-QTOFsplash10-000i-9000000000-e9262cbaff8cb4ad0ba62021-09-23Wishart 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 ID448
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPalmitoylcarnitine
METLIN IDNot Available
PubChem Compound461
PDB IDNot Available
ChEBI ID73067
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1684361
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Wasant P, Matsumoto I, Naylor E, Liammongkolkul S: Mitochondrial fatty acid oxidation disorders in Thai infants: a report of 3 cases. J Med Assoc Thai. 2002 Aug;85 Suppl 2:S710-9. [PubMed:12403251 ]
  2. Minkler PE, Kerner J, North KN, Hoppel CL: Quantitation of long-chain acylcarnitines by HPLC/fluorescence detection: application to plasma and tissue specimens from patients with carnitine palmitoyltransferase-II deficiency. Clin Chim Acta. 2005 Feb;352(1-2):81-92. [PubMed:15653102 ]
  3. Fingerhut R, Roschinger W, Muntau AC, Dame T, Kreischer J, Arnecke R, Superti-Furga A, Troxler H, Liebl B, Olgemoller B, Roscher AA: Hepatic carnitine palmitoyltransferase I deficiency: acylcarnitine profiles in blood spots are highly specific. Clin Chem. 2001 Oct;47(10):1763-8. [PubMed:11568084 ]
  4. Costa CG, Struys EA, Bootsma A, ten Brink HJ, Dorland L, Tavares de Almeida I, Duran M, Jakobs C: Quantitative analysis of plasma acylcarnitines using gas chromatography chemical ionization mass fragmentography. J Lipid Res. 1997 Jan;38(1):173-82. [PubMed:9034211 ]
  5. Huang HJ, Zhang AY, Cao HC, Lu HF, Wang BH, Xie Q, Xu W, Li LJ: Metabolomic analyses of faeces reveals malabsorption in cirrhotic patients. Dig Liver Dis. 2013 Aug;45(8):677-82. doi: 10.1016/j.dld.2013.01.001. Epub 2013 Feb 4. [PubMed:23384618 ]
  6. Zordoky BN, Sung MM, Ezekowitz J, Mandal R, Han B, Bjorndahl TC, Bouatra S, Anderson T, Oudit GY, Wishart DS, Dyck JR: Metabolomic fingerprint of heart failure with preserved ejection fraction. PLoS One. 2015 May 26;10(5):e0124844. doi: 10.1371/journal.pone.0124844. eCollection 2015. [PubMed:26010610 ]
  7. Zhang X, Zhang C, Chen L, Han X, Ji L: Human serum acylcarnitine profiles in different glucose tolerance states. Diabetes Res Clin Pract. 2014 Jun;104(3):376-82. doi: 10.1016/j.diabres.2014.04.013. Epub 2014 Apr 28. [PubMed:24837145 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  11. 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 ]
  12. 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 ]
  13. 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 ]
  14. Chen Y, Li C, Liu L, Guo F, Li S, Huang L, Sun C, Feng R: Serum metabonomics of NAFLD plus T2DM based on liquid chromatography-mass spectrometry. Clin Biochem. 2016 Sep;49(13-14):962-6. doi: 10.1016/j.clinbiochem.2016.05.016. Epub 2016 May 20. [PubMed:27211699 ]
  15. Chen C, Hou G, Zeng C, Ren Y, Chen X, Peng C: Metabolomic profiling reveals amino acid and carnitine alterations as metabolic signatures in psoriasis. Theranostics. 2021 Jan 1;11(2):754-767. doi: 10.7150/thno.51154. eCollection 2021. [PubMed:33391503 ]
  16. Hunter WG, Kelly JP, McGarrah RW 3rd, Khouri MG, Craig D, Haynes C, Ilkayeva O, Stevens RD, Bain JR, Muehlbauer MJ, Newgard CB, Felker GM, Hernandez AF, Velazquez EJ, Kraus WE, Shah SH: Metabolomic Profiling Identifies Novel Circulating Biomarkers of Mitochondrial Dysfunction Differentially Elevated in Heart Failure With Preserved Versus Reduced Ejection Fraction: Evidence for Shared Metabolic Impairments in Clinical Heart Failure. J Am Heart Assoc. 2016 Jul 29;5(8). pii: JAHA.115.003190. doi: 10.1161/JAHA.115.003190. [PubMed:27473038 ]
  17. Zhang X, Li Y, Liang Y, Sun P, Wu X, Song J, Sun X, Hong M, Gao P, Deng D: Distinguishing Intracerebral Hemorrhage from Acute Cerebral Infarction through Metabolomics. Rev Invest Clin. 2017 Nov-Dec;69(6):319-328. doi: 10.24875/RIC.17002348. [PubMed:29265114 ]
  18. Brittain EL, Talati M, Fessel JP, Zhu H, Penner N, Calcutt MW, West JD, Funke M, Lewis GD, Gerszten RE, Hamid R, Pugh ME, Austin ED, Newman JH, Hemnes AR: Fatty Acid Metabolic Defects and Right Ventricular Lipotoxicity in Human Pulmonary Arterial Hypertension. Circulation. 2016 May 17;133(20):1936-44. doi: 10.1161/CIRCULATIONAHA.115.019351. Epub 2016 Mar 22. [PubMed:27006481 ]
  19. Kalim S, Clish CB, Wenger J, Elmariah S, Yeh RW, Deferio JJ, Pierce K, Deik A, Gerszten RE, Thadhani R, Rhee EP: A plasma long-chain acylcarnitine predicts cardiovascular mortality in incident dialysis patients. J Am Heart Assoc. 2013 Dec 5;2(6):e000542. doi: 10.1161/JAHA.113.000542. [PubMed:24308938 ]
  20. Ueland T, Svardal A, Oie E, Askevold ET, Nymoen SH, Bjorndal B, Dahl CP, Gullestad L, Berge RK, Aukrust P: Disturbed carnitine regulation in chronic heart failure--increased plasma levels of palmitoyl-carnitine are associated with poor prognosis. Int J Cardiol. 2013 Sep 1;167(5):1892-9. doi: 10.1016/j.ijcard.2012.04.150. Epub 2012 May 22. [PubMed:22622056 ]
  21. Yoon DW, Kwon HN, Jin X, Kim JK, Lee SK, Park S, Yun CH, Shin C: Untargeted metabolomics analysis of rat hippocampus subjected to sleep fragmentation. Brain Res Bull. 2019 Nov;153:74-83. doi: 10.1016/j.brainresbull.2019.08.008. Epub 2019 Aug 13. [PubMed:31419538 ]
  22. Qiu G, Zheng Y, Wang H, Sun J, Ma H, Xiao Y, Li Y, Yuan Y, Yang H, Li X, Min X, Zhang C, Xu C, Jiang Y, Zhang X, He M, Yang M, Hu Z, Tang H, Shen H, Hu FB, Pan A, Wu T: Plasma metabolomics identified novel metabolites associated with risk of type 2 diabetes in two prospective cohorts of Chinese adults. Int J Epidemiol. 2016 Oct;45(5):1507-1516. doi: 10.1093/ije/dyw221. Epub 2016 Sep 30. [PubMed:27694567 ]
  23. Mihalik SJ, Goodpaster BH, Kelley DE, Chace DH, Vockley J, Toledo FG, DeLany JP: Increased levels of plasma acylcarnitines in obesity and type 2 diabetes and identification of a marker of glucolipotoxicity. Obesity (Silver Spring). 2010 Sep;18(9):1695-700. doi: 10.1038/oby.2009.510. Epub 2010 Jan 28. [PubMed:20111019 ]
  24. 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 ]