Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2017-09-08 16:20:13 UTC |
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Update Date | 2022-03-07 03:18:04 UTC |
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HMDB ID | HMDB0112099 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | 5-Hexyl-2-furanoctanoic acid |
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Description | 5-Hexyl-2-furanoctanoic acid is a furan fatty acid (F-acid). F-acids are heterocyclic fatty acids containing a central furan moiety with a carboxylalkyl chain (mostly 7, 9, 11, or 13 carbons) in the 2-position and an alkyl chain (mostly 3 or 5 carbons) in the 5-position. Despite being found in low concentrations in food lipids, they are excellent antixoxidants and radical scavengers. This allows them to play an important role in preventing lipid peroxidation and protecting polyunsaturated fatty acids. They are often incorporated into phospholipids and cholesterol esters of fish and other marine organisms. 5-Hexyl-2-furanoctanoic acid, in particular, can be described by the shorthand notation 8F6. This refers to its 8-carbon carboxyalkyl moiety, the non-methylated furan moiety, and its 6-carbon alkyl moiety. It has been identified in carp. |
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Structure | CCCCCCC1=CC=C(CCCCCCCC(O)=O)O1 InChI=1S/C18H30O3/c1-2-3-4-8-11-16-14-15-17(21-16)12-9-6-5-7-10-13-18(19)20/h14-15H,2-13H2,1H3,(H,19,20) |
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Synonyms | Value | Source |
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(9Z,11Z)-9,12-Epoxyoctadeca-9,11-dienoic acid | ChEBI | 8-(5-Hexyl-furan-2-yl)-octanoic acid | ChEBI | 8-(5-Hexyl-furan-2-yl)-octanoate | Kegg | (9Z,11Z)-9,12-Epoxyoctadeca-9,11-dienoate | Generator | 8-(5-Hexylfuran-2-yl)octanoate | Generator | 8F6 | SMPDB, HMDB | 8-(5-hexyl-2-furyl)octanoic acid | SMPDB, HMDB | 5-hexyl-2-furanoctanoic acid | SMPDB | 9,12-epoxy-9,11-octadecadienoic acid | SMPDB, HMDB | 9,12-epoxyoctadeca-9,11-dienoic acid | SMPDB, HMDB | 8-(5-hexylfuran-2-yl)octanoic acid | SMPDB, HMDB | Furocarpate | Generator | 5-Hexyl-2-furanoctanoate | Generator |
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Chemical Formula | C18H30O3 |
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Average Molecular Weight | 294.435 |
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Monoisotopic Molecular Weight | 294.219494826 |
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IUPAC Name | 8-(5-hexylfuran-2-yl)octanoic acid |
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Traditional Name | 8-(5-hexylfuran-2-yl)octanoic acid |
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CAS Registry Number | Not Available |
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SMILES | CCCCCCC1=CC=C(CCCCCCCC(O)=O)O1 |
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InChI Identifier | InChI=1S/C18H30O3/c1-2-3-4-8-11-16-14-15-17(21-16)12-9-6-5-7-10-13-18(19)20/h14-15H,2-13H2,1H3,(H,19,20) |
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InChI Key | SZNVIDWMWMWUCY-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as furanoid fatty acids. These are fatty acids containing a 5-alkylfuran-2-alkanoic acid. |
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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 acids and conjugates |
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Direct Parent | Furanoid fatty acids |
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Alternative Parents | |
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Substituents | - Furanoid fatty acid
- Medium-chain fatty acid
- Heteroaromatic compound
- Furan
- Oxacycle
- Organoheterocyclic compound
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | Not Available |
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Process | Not Available |
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Role | Not Available |
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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 SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatized |
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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 - 5-Hexyl-2-furanoctanoic acid GC-MS (1 TMS) - 70eV, Positive | splash10-00bl-9442000000-4d449297d771cd15710d | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5-Hexyl-2-furanoctanoic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-9570000000-c07b30530c1d91c41507 | 2017-11-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5-Hexyl-2-furanoctanoic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5-Hexyl-2-furanoctanoic acid 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 - 5-Hexyl-2-furanoctanoic acid 10V, Positive-QTOF | splash10-004j-0090000000-60b82ef75902d3cce3e4 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-Hexyl-2-furanoctanoic acid 20V, Positive-QTOF | splash10-00tb-8590000000-82a1d62c8d274866a187 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-Hexyl-2-furanoctanoic acid 40V, Positive-QTOF | splash10-05mo-9310000000-c9dadce3e6d4cf799b90 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-Hexyl-2-furanoctanoic acid 10V, Negative-QTOF | splash10-0006-0090000000-0366179feb6bf43f3296 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-Hexyl-2-furanoctanoic acid 20V, Negative-QTOF | splash10-002g-1290000000-a09d119e825b5f48c758 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-Hexyl-2-furanoctanoic acid 40V, Negative-QTOF | splash10-0a4l-9720000000-dda196963c357a83d31e | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-Hexyl-2-furanoctanoic acid 10V, Positive-QTOF | splash10-056s-1290000000-8f956e2d9ebe35712b04 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-Hexyl-2-furanoctanoic acid 20V, Positive-QTOF | splash10-056r-8490000000-472748ddc91a879cbf44 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-Hexyl-2-furanoctanoic acid 40V, Positive-QTOF | splash10-0a4l-9400000000-3a249313f60bd759479c | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-Hexyl-2-furanoctanoic acid 10V, Negative-QTOF | splash10-0006-0090000000-d703c836b2e7ccf73193 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-Hexyl-2-furanoctanoic acid 20V, Negative-QTOF | splash10-002f-0190000000-aa6d6547fec426b6edc0 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-Hexyl-2-furanoctanoic acid 40V, Negative-QTOF | splash10-0006-8950000000-12821e24deb1e29c6bd3 | 2021-09-24 | Wishart Lab | View Spectrum |
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General References | - 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 ]
- Vetter W, Wendlinger C (2013). Furan fatty acids – valuable minor fatty acids in food. Lipid Technology.
- Vetter W, Ulms K, Wendlinger C, van Rijn J (2016). Novel non-methylated furan fatty acids in fish from a zero discharge aquaculture system. NFS Journal.
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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