Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2006-10-23 13:16:22 UTC |
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Update Date | 2022-03-07 02:49:25 UTC |
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HMDB ID | HMDB0005066 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Tetradecanoylcarnitine |
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Description | Tetradecanoylcarnitine, also known as myristoylcarnitine, is a member of the class of compounds known as acylcarnitines. Acylcarnitines are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond. Acylcarnitines are useful in the diagnosis of genetic disorders such as fatty acid oxidation disorders and differentiation between biochemical phenotypes of medium-chain acyl-CoA dehydrogenase (MCAD) deficiency disorders (PMID: 12385891 ). Tetradecanoylcarnitine is involved in the beta-oxidation of long-chain fatty acids (PMID: 16425363 ). Tetradecanoylcarnitine is found to be associated with glutaric aciduria II, which is an inborn error of metabolism. |
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Structure | CCCCCCCCCCCCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C InChI=1S/C21H41NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-21(25)26-19(17-20(23)24)18-22(2,3)4/h19H,5-18H2,1-4H3/t19-/m1/s1 |
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Synonyms | Value | Source |
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(-)-Myristoylcarnitine | ChEBI | (-)-Tetradecanoylcarnitine | ChEBI | (R)-Myristoylcarnitine | ChEBI | (R)-Tetradecanoylcarnitine | ChEBI | L-Myristoylcarnitine | ChEBI | Myristoyl-L-(-)-carnitine | ChEBI | Myristoyl-L-carnitine | ChEBI | Myristoylcarnitine | ChEBI | O-Tetradecanoyl-(R)-carnitine | ChEBI | Tetradecanoyl-L-carnitine | ChEBI | C14 Carnitine | HMDB | Tetradecanoylcarnitine | HMDB |
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Chemical Formula | C21H42NO4 |
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Average Molecular Weight | 372.569 |
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Monoisotopic Molecular Weight | 372.310835257 |
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IUPAC Name | (3R)-3-(tetradecanoyloxy)-4-(trimethylazaniumyl)butanoate |
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Traditional Name | (3R)-3-(tetradecanoyloxy)-4-(trimethylammonio)butanoate |
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CAS Registry Number | 25597-07-3 |
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SMILES | CCCCCCCCCCCCCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C |
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InChI Identifier | InChI=1S/C21H41NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-21(25)26-19(17-20(23)24)18-22(2,3)4/h19H,5-18H2,1-4H3/p+1/t19-/m1/s1 |
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InChI Key | PSHXNVGSVNEJBD-LJQANCHMSA-O |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Fatty Acyls |
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Sub Class | Fatty acid esters |
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Direct Parent | Acyl carnitines |
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Alternative Parents | |
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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
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | |
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Disposition | Biological locationRoute of exposureSourceEndogenousExogenousFood- Food (HMDB: HMDB0005066)
Animal originMilk and milk productUnfermented milk- Milk (Cow) (FooDB: FOOD00618)
- Cow milk, pasteurized, vitamin A + D added, 0% fat (FooDB: FOOD00889)
- Cow milk, pasteurized, vitamin A + D added, 1% fat (FooDB: FOOD00890)
- Cow milk, pasteurized, vitamin A + D added, 2% fat (FooDB: FOOD00891)
- Cow milk, pasteurized, vitamin D added, 3.25% fat (FooDB: FOOD00892)
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Process | |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredictor | Adduct Type | CCS Value (Å2) | Reference |
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DeepCCS | [M+H]+ | 206.759 | 30932474 | DeepCCS | [M-H]- | 202.739 | 30932474 | DeepCCS | [M-2H]- | 239.282 | 30932474 | DeepCCS | [M+Na]+ | 215.574 | 30932474 |
Predicted Kovats Retention IndicesUnderivatizedDerivatized |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Tetradecanoylcarnitine GC-MS (Non-derivatized) - 70eV, Positive | splash10-00di-9310000000-80762110d17332491ce0 | 2016-09-22 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Tetradecanoylcarnitine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tetradecanoylcarnitine 10V, Positive-QTOF | splash10-00di-0009000000-ebacd89483d3e5c1fe24 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tetradecanoylcarnitine 20V, Positive-QTOF | splash10-0079-9005000000-55ccdfe0f24295822965 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tetradecanoylcarnitine 40V, Positive-QTOF | splash10-000i-9000000000-e9262cbaff8cb4ad0ba6 | 2021-09-24 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 0.04 +/- 0.01 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 0.030-0.070 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 0.030-0.070 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 0.02 +/- 0.02 uM | Children (1-13 years old) | Both | Normal | | details | Blood | Detected and Quantified | 0.01 +/- 0.01 uM | Children (1-13 years old) | Both | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 0.05(0.01) uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | <0.18 uM | Adolescent (13-18 years old) | Male | Normal | | details | Blood | Detected and Quantified | 0.016 (0.002-0.043) uM | Children (1-13 years old) | Both | Normal | | details | Feces | Detected and Quantified | 0.54 +/- 0.47 nmol/g wet feces | Adult (>18 years old) | Both | Normal | | details | Feces | Detected and Quantified | 0.32 +/- 0.29 nmol/g wet feces | Adult (>18 years old) | Both | Normal | | details | Saliva | Detected and Quantified | 0.056 +/- 0.056 uM | Adult (>18 years old) | Both | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.018 (0.001-0.088) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.01-0.09 umol/mmol creatinine | Newborn (0-30 days old) | Both | Normal | | details | Urine | Detected and Quantified | 0.02(0.01-0.09) umol/mmol creatinine | Newborn (0-30 days old) | Female | Normal | | details | Urine | Detected and Quantified | 0.02(0.01-0.07) umol/mmol creatinine | Newborn (0-30 days old) | Male | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected and Quantified | 0.719 (0.478-0.983) uM | Adult (>18 years old) | Both | Very long-chain acyl-CoA dehydrogenase deficiency (vLCAD) | | details | Blood | Detected and Quantified | 0.02 +/- 0.02 uM | Children (1-13 years old) | Both | Acetaminophen overdose | | details | Blood | Detected and Quantified | 0.05(0.01) uM | Adult (>18 years old) | Both | Heart failure with preserved ejection fraction | | details | Blood | Detected and Quantified | 0.0337 (0.0126) uM | Adult (>18 years old) | Female | Pregnancy with fetus having congenital heart defect | | details | Blood | Detected and Quantified | 0.0403 (0.0065) uM | Adult (>18 years old) | Female | Pregnancy | | details | Blood | Detected and Quantified | 0.043 +/- 0.015 uM | Children (1-13 years old) | Both | Obesity | | details | Blood | Detected and Quantified | 0.047 +/- 0.018 uM | Children (1-13 years old) | Both | Obesity | | details | Blood | Detected and Quantified | 0.3 uM | Adolescent (13-18 years old) | Male | Glutaric aciduria II | | details | Blood | Detected and Quantified | 0.92 uM | Adolescent (13-18 years old) | Male | Glutaric aciduria II | | details |
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Associated Disorders and Diseases |
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Disease References | Very Long Chain Acyl-CoA Dehydrogenase Deficiency |
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- 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 ]
| Pregnancy |
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- Bahado-Singh RO, Ertl R, Mandal R, Bjorndahl TC, Syngelaki A, Han B, Dong E, Liu PB, Alpay-Savasan Z, Wishart DS, Nicolaides KH: Metabolomic prediction of fetal congenital heart defect in the first trimester. Am J Obstet Gynecol. 2014 Sep;211(3):240.e1-240.e14. doi: 10.1016/j.ajog.2014.03.056. Epub 2014 Apr 1. [PubMed:24704061 ]
| Glutaric aciduria II |
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- Prasad M, Hussain S: Glutaric aciduria type II presenting as myopathy and rhabdomyolysis in a teenager. J Child Neurol. 2015 Jan;30(1):96-9. doi: 10.1177/0883073813516676. Epub 2014 Jan 21. [PubMed:24453145 ]
| Obesity |
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- Simone Wahl, Christina Holzapfel, Zhonghao Yu, Michaela Breier, Ivan Kondofersky, Christiane Fuchs, Paula Singmann, Cornelia Prehn, Jerzy Adamski, Harald Grallert, Thomas Illig, Rui Wang-Sattler, Thomas Reinehr (2013). Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children. Metabolomics.
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Associated OMIM IDs | - 201475 (Very Long Chain Acyl-CoA Dehydrogenase Deficiency)
- 231680 (Glutaric aciduria II)
- 601665 (Obesity)
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB023615 |
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KNApSAcK ID | C00052417 |
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Chemspider ID | 30776567 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 53477791 |
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PDB ID | Not Available |
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ChEBI ID | 84634 |
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Food Biomarker Ontology | Not Available |
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VMH ID | M02973 |
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MarkerDB ID | MDB00000468 |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Okun JG, Kolker S, Schulze A, Kohlmuller D, Olgemoller K, Lindner M, Hoffmann GF, Wanders RJ, Mayatepek E: A method for quantitative acylcarnitine profiling in human skin fibroblasts using unlabelled palmitic acid: diagnosis of fatty acid oxidation disorders and differentiation between biochemical phenotypes of MCAD deficiency. Biochim Biophys Acta. 2002 Oct 10;1584(2-3):91-8. [PubMed:12385891 ]
- Bene J, Komlosi K, Gasztonyi B, Juhasz M, Tulassay Z, Melegh B: Plasma carnitine ester profile in adult celiac disease patients maintained on long-term gluten free diet. World J Gastroenterol. 2005 Nov 14;11(42):6671-5. [PubMed:16425363 ]
- Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]
- Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
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