Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2022-10-24 19:44:10 UTC |
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HMDB ID | HMDB0000736 |
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Secondary Accession Numbers | - HMDB0002083
- HMDB0062556
- HMDB0062606
- HMDB00736
- HMDB02083
- HMDB62556
- HMDB62606
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Metabolite Identification |
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Common Name | Isobutyryl-L-carnitine |
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Description | Isobutyryl-L-carnitine is an acylcarnitine. More specifically, it is an isobutyric 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. Isobutyryl-L-carnitine is therefore classified as a short chain AC. As a short-chain acylcarnitine isobutyryl-L-carnitine is a member of the most abundant group of carnitines in the body, comprising more than 50% of all acylcarnitines quantified in tissues and biofluids (PMID: 31920980 ). Some short-chain carnitines have been studied as supplements or treatments for a number of diseases, including neurological disorders and inborn errors of metabolism. In particular isobutyryl-L-carnitine is elevated in the blood or plasma of individuals with isobutyryl-coa dehydrogenase deficiency (PMID: 20591710 ), glutaric aciduria type 2 (PMID: 20591710 ), ethylmalonic encephalopathy (PMID: 20591710 ), and gestational diabetes mellitus (PMID: 29626588 ). It is also decreased in the blood or plasma of individuals with traumatic brain injury (PMID: 23560894 ). Isobutyryl-L-carnitine is elevated in the urine of individuals with glutaric aciduria type 2 (PMID: 2288224 ), multiple acyl-CoA dehydrogenation deficiency (PMID: 3383426 ), and acute coronary syndrome (PMID: 30316136 ). Carnitine acetyltransferase (CrAT, EC:2.3.1.7) is responsible for the synthesis of all short-chain and short branched-chain acylcarnitines (PMID: 23485643 ). 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 ). |
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Structure | CC(C)C(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C InChI=1S/C11H21NO4/c1-8(2)11(15)16-9(6-10(13)14)7-12(3,4)5/h8-9H,6-7H2,1-5H3/t9-/m1/s1 |
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Synonyms | Value | Source |
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(R)-Isobutyrylcarnitine | ChEBI | Iso-butyryl-L(-)-carnitin | ChEBI | Isobutyryl-carnitine | ChEBI | Isobutyryl-L-(-)-carnitine | ChEBI | O-Isobutanoyl-(R)-carnitine | ChEBI | Isobutyryl-1-carnitine | HMDB | Isobutyrylcarnitine | HMDB | O-Isobutyryl-L-carnitine | HMDB | Isobutyryl-L-carnitine | HMDB, ChEBI |
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Chemical Formula | C11H22NO4 |
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Average Molecular Weight | 232.299 |
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Monoisotopic Molecular Weight | 232.154334613 |
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IUPAC Name | (3R)-3-[(2-methylpropanoyl)oxy]-4-(trimethylazaniumyl)butanoate |
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Traditional Name | (3R)-3-[(2-methylpropanoyl)oxy]-4-(trimethylammonio)butanoate |
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CAS Registry Number | 25518-49-4 |
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SMILES | CC(C)C(=O)O[C@H](CC(O)=O)C[N+](C)(C)C |
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InChI Identifier | InChI=1S/C11H21NO4/c1-8(2)11(15)16-9(6-10(13)14)7-12(3,4)5/h8-9H,6-7H2,1-5H3/p+1/t9-/m1/s1 |
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InChI Key | LRCNOZRCYBNMEP-SECBINFHSA-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
- Branched fatty acid
- Dicarboxylic acid or derivatives
- Tetraalkylammonium salt
- Quaternary ammonium salt
- Carboxylic acid ester
- Carboxylic acid salt
- Carboxylic acid derivative
- Carboxylic acid
- Organonitrogen compound
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Organic nitrogen compound
- Carbonyl group
- Organic oxygen compound
- Amine
- Organooxygen compound
- Organic salt
- 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 | |
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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 SectionsPredicted 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 - Isobutyryl-L-carnitine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Isobutyryl-L-carnitine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Isobutyryl-L-carnitine GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Isobutyryl-L-carnitine GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - Isobutyryl-L-carnitine Quattro_QQQ 10V, Positive-QTOF (Annotated) | splash10-001i-5290000000-baab610a0cdc91406add | 2018-05-25 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Isobutyryl-L-carnitine Quattro_QQQ 25V, Positive-QTOF (Annotated) | splash10-001i-9000000000-8d180efb75e39baa17aa | 2018-05-25 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Isobutyryl-L-carnitine Quattro_QQQ 40V, Positive-QTOF (Annotated) | splash10-001i-9000000000-6311075865704b40d294 | 2018-05-25 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isobutyryl-L-carnitine 10V, Positive-QTOF | splash10-001i-0090000000-cf95ec9e05e8b6c1a98f | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isobutyryl-L-carnitine 20V, Positive-QTOF | splash10-0019-9050000000-ebf3a8e1eb1d0ceaaeba | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isobutyryl-L-carnitine 40V, Positive-QTOF | splash10-000i-9000000000-e9262cbaff8cb4ad0ba6 | 2021-09-22 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Experimental 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | 2018-05-25 | 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 | 0.069 (0.015-0.203) 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 | 0.069 (0.015-0.203) uM | Children (1-13 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0 umol/mmol creatinine | Infant (0-1 year old) | Both | Normal | | details | Urine | Detected and Quantified | 0.05-0.33 umol/mmol creatinine | Newborn (0-30 days old) | Both | Normal | | details | Urine | Detected and Quantified | 0.11 +/- 0.06 umol/mmol creatinine | Newborn (0-30 days old) | Female | Normal | | details | Urine | Detected and Quantified | 0.13 +/- 0.07 umol/mmol creatinine | Newborn (0-30 days old) | Male | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected and Quantified | 0.034 (0.009-0.084) uM | Adult (>18 years old) | Both | Very long-chain acyl-CoA dehydrogenase deficiency (vLCAD) | | details | Urine | Detected and Quantified | 0 umol/mmol creatinine | Infant (0-1 year old) | Both | Short chain acyl-CoA dehydrogenase deficiency (SCAD) | | 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 ]
| Short Chain Acyl-Coa Dehydrogenase Deficiency |
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- Bhala A, Willi SM, Rinaldo P, Bennett MJ, Schmidt-Sommerfeld E, Hale DE: Clinical and biochemical characterization of short-chain acyl-coenzyme A dehydrogenase deficiency. J Pediatr. 1995 Jun;126(6):910-5. [PubMed:7776094 ]
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Associated OMIM IDs | - 201475 (Very Long Chain Acyl-CoA Dehydrogenase Deficiency)
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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 | FDB022213 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 147286 |
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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 | 5704 |
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PubChem Compound | 168379 |
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PDB ID | Not Available |
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ChEBI ID | 84838 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | MDB00000241 |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Strack, Erich; Mueller, Detlef M. Preparation of O-acylcarnitines. Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie (1970), 351(1), 95-8. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Sass JO, Sander S, Zschocke J: Isobutyryl-CoA dehydrogenase deficiency: isobutyrylglycinuria and ACAD8 gene mutations in two infants. J Inherit Metab Dis. 2004;27(6):741-5. [PubMed:15505379 ]
- Kidouchi K, Niwa T, Nohara D, Asai K, Sugiyama N, Morishita H, Kobayashi M, Wada Y: Urinary acylcarnitines in a patient with neonatal multiple acyl-CoA dehydrogenation deficiency, quantified by a carboxylic acid analyzer with a reversed-phase column. Clin Chim Acta. 1988 Apr 29;173(3):263-72. [PubMed:3383426 ]
- Minkler PE, Ingalls ST, Hoppel CL: High-performance liquid chromatographic separation of acylcarnitines following derivatization with 4'-bromophenacyl trifluoromethanesulfonate. Anal Biochem. 1990 Feb 15;185(1):29-35. [PubMed:2344045 ]
- Roe CR, Cederbaum SD, Roe DS, Mardach R, Galindo A, Sweetman L: Isolated isobutyryl-CoA dehydrogenase deficiency: an unrecognized defect in human valine metabolism. Mol Genet Metab. 1998 Dec;65(4):264-71. [PubMed:9889013 ]
- Sakuma T, Sugiyama N, Ichiki T, Kobayashi M, Wada Y, Nohara D: Analysis of acylcarnitines in maternal urine for prenatal diagnosis of glutaric aciduria type 2. Prenat Diagn. 1991 Feb;11(2):77-82. [PubMed:2062823 ]
- Vallee L, Fontaine M, Nuyts JP, Ricart G, Krivosic I, Divry P, Vianey-Saban C, Lhermitte M, Vamecq J: Stroke, hemiparesis and deficient mitochondrial beta-oxidation. Eur J Pediatr. 1994 Aug;153(8):598-603. [PubMed:7957409 ]
- Sugiyama N, Kidouchi K, Kobayashi M, Wada Y: Carnitine deficiency in inherited organic acid disorders and Reye syndrome. Acta Paediatr Jpn. 1990 Aug;32(4):410-6. [PubMed:2288224 ]
- Koeberl DD, Young SP, Gregersen NS, Vockley J, Smith WE, Benjamin DK Jr, An Y, Weavil SD, Chaing SH, Bali D, McDonald MT, Kishnani PS, Chen YT, Millington DS: Rare disorders of metabolism with elevated butyryl- and isobutyryl-carnitine detected by tandem mass spectrometry newborn screening. Pediatr Res. 2003 Aug;54(2):219-23. Epub 2003 May 7. [PubMed:12736383 ]
- Fontaine M, Briand G, Largilliere C, Degand P, Divry P, Vianey-Saban C, Mousson B, Vamecq J: Metabolic studies in a patient with severe carnitine palmitoyltransferase type II deficiency. Clin Chim Acta. 1998 May 25;273(2):161-70. [PubMed:9657346 ]
- Matsumoto K, Takahashi M, Takiyama N, Misaki H, Matsuo N, Murano S, Yuki H: Enzyme reactor for urinary acylcarnitines assay by reversed-phase high-performance liquid chromatography. Clin Chim Acta. 1993 Jul 16;216(1-2):135-43. [PubMed:8222264 ]
- Shalev DP, Soffer Y, Lewin LM: Investigations on the motility of human spermatozoa in a defined medium in the presence of metabolic inhibitors and of carnitine. Andrologia. 1986 Jul-Aug;18(4):368-75. [PubMed:3752540 ]
- Fontaine M, Briand G, Ser N, Armelin I, Rolland MO, Degand P, Vamecq J: Metabolic studies in twin brothers with 2-methylacetoacetyl-CoA thiolase deficiency. Clin Chim Acta. 1996 Nov 15;255(1):67-83. [PubMed:8930414 ]
- Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
- Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
- Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
- Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
- Violante S, Ijlst L, Ruiter J, Koster J, van Lenthe H, Duran M, de Almeida IT, Wanders RJ, Houten SM, Ventura FV: Substrate specificity of human carnitine acetyltransferase: Implications for fatty acid and branched-chain amino acid metabolism. Biochim Biophys Acta. 2013 Jun;1832(6):773-9. doi: 10.1016/j.bbadis.2013.02.012. Epub 2013 Feb 24. [PubMed:23485643 ]
- 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 ]
- 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 ]
- Makarova E, Makrecka-Kuka M, Vilks K, Volska K, Sevostjanovs E, Grinberga S, Zarkova-Malkova O, Dambrova M, Liepinsh E: Decreases in Circulating Concentrations of Long-Chain Acylcarnitines and Free Fatty Acids During the Glucose Tolerance Test Represent Tissue-Specific Insulin Sensitivity. Front Endocrinol (Lausanne). 2019 Dec 17;10:870. doi: 10.3389/fendo.2019.00870. eCollection 2019. [PubMed:31920980 ]
- Forni S, Fu X, Palmer SE, Sweetman L: Rapid determination of C4-acylcarnitine and C5-acylcarnitine isomers in plasma and dried blood spots by UPLC-MS/MS as a second tier test following flow-injection MS/MS acylcarnitine profile analysis. Mol Genet Metab. 2010 Sep;101(1):25-32. doi: 10.1016/j.ymgme.2010.05.012. Epub 2010 Jun 10. [PubMed:20591710 ]
- Roy C, Tremblay PY, Anassour-Laouan-Sidi E, Lucas M, Forest JC, Giguere Y, Ayotte P: Risk of gestational diabetes mellitus in relation to plasma concentrations of amino acids and acylcarnitines: A nested case-control study. Diabetes Res Clin Pract. 2018 Jun;140:183-190. doi: 10.1016/j.diabres.2018.03.058. Epub 2018 Apr 4. [PubMed:29626588 ]
- Jeter CB, Hergenroeder GW, Ward NH 3rd, Moore AN, Dash PK: Human mild traumatic brain injury decreases circulating branched-chain amino acids and their metabolite levels. J Neurotrauma. 2013 Apr 15;30(8):671-9. doi: 10.1089/neu.2012.2491. Epub 2013 Apr 6. [PubMed:23560894 ]
- Wang Y, Sun W, Zheng J, Xu C, Wang X, Li T, Tang Y, Li Z: Urinary metabonomic study of patients with acute coronary syndrome using UPLC-QTOF/MS. J Chromatogr B Analyt Technol Biomed Life Sci. 2018 Nov 15;1100-1101:122-130. doi: 10.1016/j.jchromb.2018.10.005. Epub 2018 Oct 7. [PubMed:30316136 ]
- 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 ]
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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