Record Information |
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Version | 5.0 |
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Status | Predicted |
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Creation Date | 2021-03-31 19:23:20 UTC |
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Update Date | 2022-10-24 19:45:15 UTC |
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HMDB ID | HMDB0241624 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | (4E,6E,10Z,13Z,16Z,19Z)-8-Hydroxydocosa-4,6,10,13,16,19-hexaenoylcarnitine |
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Description | (4E,6E,10Z,13Z,16Z,19Z)-8-hydroxydocosa-4,6,10,13,16,19-hexaenoylcarnitine is an acylcarnitine. More specifically, it is an (4E,6E,10Z,13Z,16Z,19Z)-8-hydroxydocosa-4,6,10,13,16,19-hexaenoic 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. (4E,6E,10Z,13Z,16Z,19Z)-8-hydroxydocosa-4,6,10,13,16,19-hexaenoylcarnitine is therefore classified as a very-long chain AC. As a very long-chain acylcarnitine (4E,6E,10Z,13Z,16Z,19Z)-8-hydroxydocosa-4,6,10,13,16,19-hexaenoylcarnitine is generally formed in the cytoplasm from very long acyl groups synthesized by fatty acid synthases or obtained from the diet. Very-long-chain fatty acids are generally too long to be involved in mitochondrial beta-oxidation. As a result peroxisomes are the main organelle where very-long-chain fatty acids are metabolized and their acylcarnitines synthesized (PMID: 18793625 ). Altered levels of very long-chain acylcarnitines can serve as useful markers for inherited disorders of peroxisomal metabolism. 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 | CCC=CCC=CCC=CCC=CCC(O)C=CC=CCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C InChI=1S/C29H45NO5/c1-5-6-7-8-9-10-11-12-13-14-15-18-21-26(31)22-19-16-17-20-23-29(34)35-27(24-28(32)33)25-30(2,3)4/h6-7,9-10,12-13,15-19,22,26-27,31H,5,8,11,14,20-21,23-25H2,1-4H3 |
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Synonyms | Not Available |
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Chemical Formula | C29H45NO5 |
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Average Molecular Weight | 487.681 |
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Monoisotopic Molecular Weight | 487.329773553 |
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IUPAC Name | 3-[(8-hydroxydocosa-4,6,10,13,16,19-hexaenoyl)oxy]-4-(trimethylazaniumyl)butanoate |
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Traditional Name | 3-[(8-hydroxydocosa-4,6,10,13,16,19-hexaenoyl)oxy]-4-(trimethylammonio)butanoate |
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CAS Registry Number | Not Available |
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SMILES | CCC=CCC=CCC=CCC=CCC(O)C=CC=CCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C |
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InChI Identifier | InChI=1S/C29H45NO5/c1-5-6-7-8-9-10-11-12-13-14-15-18-21-26(31)22-19-16-17-20-23-29(34)35-27(24-28(32)33)25-30(2,3)4/h6-7,9-10,12-13,15-19,22,26-27,31H,5,8,11,14,20-21,23-25H2,1-4H3 |
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InChI Key | SIKRBCBTMHIBGN-UHFFFAOYSA-N |
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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
- Secondary alcohol
- Carboxylic acid salt
- Carboxylic acid ester
- Carboxylic acid
- Carboxylic acid derivative
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Organic salt
- Organic zwitterion
- Organooxygen compound
- Organonitrogen compound
- Carbonyl group
- Amine
- Alcohol
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | |
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Disposition | |
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Process | Not Available |
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Role | |
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Physical Properties |
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State | Not Available |
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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]+ | 232.859 | 30932474 | DeepCCS | [M-H]- | 230.384 | 30932474 | DeepCCS | [M-2H]- | 263.853 | 30932474 | DeepCCS | [M+Na]+ | 240.356 | 30932474 |
Predicted Kovats Retention IndicesUnderivatizedMetabolite | SMILES | Kovats RI Value | Column Type | Reference |
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(4E,6E,10Z,13Z,16Z,19Z)-8-Hydroxydocosa-4,6,10,13,16,19-hexaenoylcarnitine | CCC=CCC=CCC=CCC=CCC(O)C=CC=CCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C | 4727.2 | Standard polar | 33892256 | (4E,6E,10Z,13Z,16Z,19Z)-8-Hydroxydocosa-4,6,10,13,16,19-hexaenoylcarnitine | CCC=CCC=CCC=CCC=CCC(O)C=CC=CCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C | 2999.7 | Standard non polar | 33892256 | (4E,6E,10Z,13Z,16Z,19Z)-8-Hydroxydocosa-4,6,10,13,16,19-hexaenoylcarnitine | CCC=CCC=CCC=CCC=CCC(O)C=CC=CCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C | 3430.8 | Semi standard non polar | 33892256 |
DerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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(4E,6E,10Z,13Z,16Z,19Z)-8-Hydroxydocosa-4,6,10,13,16,19-hexaenoylcarnitine,1TMS,isomer #1 | CCC=CCC=CCC=CCC=CCC(C=CC=CCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)O[Si](C)(C)C | 3497.2 | Semi standard non polar | 33892256 | (4E,6E,10Z,13Z,16Z,19Z)-8-Hydroxydocosa-4,6,10,13,16,19-hexaenoylcarnitine,1TBDMS,isomer #1 | CCC=CCC=CCC=CCC=CCC(C=CC=CCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)O[Si](C)(C)C(C)(C)C | 3717.0 | Semi standard non polar | 33892256 |
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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 - (4E,6E,10Z,13Z,16Z,19Z)-8-Hydroxydocosa-4,6,10,13,16,19-hexaenoylcarnitine 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 - (4E,6E,10Z,13Z,16Z,19Z)-8-Hydroxydocosa-4,6,10,13,16,19-hexaenoylcarnitine 10V, Positive-QTOF | Not Available | 2021-04-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (4E,6E,10Z,13Z,16Z,19Z)-8-Hydroxydocosa-4,6,10,13,16,19-hexaenoylcarnitine 20V, Positive-QTOF | Not Available | 2021-04-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (4E,6E,10Z,13Z,16Z,19Z)-8-Hydroxydocosa-4,6,10,13,16,19-hexaenoylcarnitine 40V, Positive-QTOF | Not Available | 2021-04-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (4E,6E,10Z,13Z,16Z,19Z)-8-Hydroxydocosa-4,6,10,13,16,19-hexaenoylcarnitine 10V, Positive-QTOF | splash10-000i-0000900000-ee01cc9607e26ee369d2 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (4E,6E,10Z,13Z,16Z,19Z)-8-Hydroxydocosa-4,6,10,13,16,19-hexaenoylcarnitine 20V, Positive-QTOF | splash10-000i-9000500000-d7223ee2ee4c17687050 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (4E,6E,10Z,13Z,16Z,19Z)-8-Hydroxydocosa-4,6,10,13,16,19-hexaenoylcarnitine 40V, Positive-QTOF | splash10-000i-9000000000-e9262cbaff8cb4ad0ba6 | 2021-09-24 | Wishart Lab | View Spectrum |
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General References | - Blazenovic I, Kind T, Sa MR, Ji J, Vaniya A, Wancewicz B, Roberts BS, Torbasinovic H, Lee T, Mehta SS, Showalter MR, Song H, Kwok J, Jahn D, Kim J, Fiehn O: Structure Annotation of All Mass Spectra in Untargeted Metabolomics. Anal Chem. 2019 Feb 5;91(3):2155-2162. doi: 10.1021/acs.analchem.8b04698. Epub 2019 Jan 16. [PubMed:30608141 ]
- 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 ]
- Duranti G, Boenzi S, Rizzo C, Rava L, Di Ciommo V, Carrozzo R, Meschini MC, Johnson DW, Dionisi-Vici C: Urine acylcarnitine analysis by ESI-MS/MS: a new tool for the diagnosis of peroxisomal biogenesis disorders. Clin Chim Acta. 2008 Dec;398(1-2):86-9. doi: 10.1016/j.cca.2008.08.018. Epub 2008 Aug 28. [PubMed:18793625 ]
- Yu D, Zhou L, Xuan Q, Wang L, Zhao X, Lu X, Xu G: Strategy for Comprehensive Identification of Acylcarnitines Based on Liquid Chromatography-High-Resolution Mass Spectrometry. Anal Chem. 2018 May 1;90(9):5712-5718. doi: 10.1021/acs.analchem.7b05471. Epub 2018 Apr 20. [PubMed:29651844 ]
- Yan X, Markey SP, Marupaka R, Dong Q, Cooper BT, Mirokhin YA, Wallace WE, Stein SE: Mass Spectral Library of Acylcarnitines Derived from Human Urine. Anal Chem. 2020 May 5;92(9):6521-6528. doi: 10.1021/acs.analchem.0c00129. Epub 2020 Apr 23. [PubMed:32271007 ]
- Zuniga A, Li L: Ultra-high performance liquid chromatography tandem mass spectrometry for comprehensive analysis of urinary acylcarnitines. Anal Chim Acta. 2011 Mar 9;689(1):77-84. doi: 10.1016/j.aca.2011.01.018. Epub 2011 Jan 18. [PubMed:21338760 ]
- 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 ]
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