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 16:37:59 UTC |
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Update Date | 2022-03-07 03:18:05 UTC |
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HMDB ID | HMDB0112193 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | 6-Hydroxyoctadecanoic acid |
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Description | Dl-6-hydroxy stearic acid belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Dl-6-hydroxy stearic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. |
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Structure | CCCCCCCCCCCCC(O)CCCCC(O)=O InChI=1S/C18H36O3/c1-2-3-4-5-6-7-8-9-10-11-14-17(19)15-12-13-16-18(20)21/h17,19H,2-16H2,1H3,(H,20,21) |
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Synonyms | Value | Source |
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DL-6-Hydroxy stearate | Generator | 18:0(6-OH) | SMPDB, HMDB | 6-hydroxystearic acid | SMPDB, HMDB | 6-DL-hydroxystearic acid | SMPDB, HMDB | 6-hydroxyoctadecanoic acid | SMPDB | 6-Hydroxyoctadecanoate | Generator |
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Chemical Formula | C18H36O3 |
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Average Molecular Weight | 300.483 |
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Monoisotopic Molecular Weight | 300.266445019 |
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IUPAC Name | 6-hydroxyoctadecanoic acid |
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Traditional Name | DL-6-hydroxy stearic acid |
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CAS Registry Number | 3158-47-2 |
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SMILES | CCCCCCCCCCCCC(O)CCCCC(O)=O |
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InChI Identifier | InChI=1S/C18H36O3/c1-2-3-4-5-6-7-8-9-10-11-14-17(19)15-12-13-16-18(20)21/h17,19H,2-16H2,1H3,(H,20,21) |
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InChI Key | LXKCZUOSRQSRHW-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. |
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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 | Long-chain fatty acids |
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Alternative Parents | |
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Substituents | - Long-chain fatty acid
- Hydroxy fatty acid
- Secondary alcohol
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Alcohol
- 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 | 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 IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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6-Hydroxyoctadecanoic acid,1TMS,isomer #1 | CCCCCCCCCCCCC(CCCCC(=O)O)O[Si](C)(C)C | 2416.6 | Semi standard non polar | 33892256 | 6-Hydroxyoctadecanoic acid,1TMS,isomer #2 | CCCCCCCCCCCCC(O)CCCCC(=O)O[Si](C)(C)C | 2413.1 | Semi standard non polar | 33892256 | 6-Hydroxyoctadecanoic acid,2TMS,isomer #1 | CCCCCCCCCCCCC(CCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 2437.4 | Semi standard non polar | 33892256 | 6-Hydroxyoctadecanoic acid,1TBDMS,isomer #1 | CCCCCCCCCCCCC(CCCCC(=O)O)O[Si](C)(C)C(C)(C)C | 2665.8 | Semi standard non polar | 33892256 | 6-Hydroxyoctadecanoic acid,1TBDMS,isomer #2 | CCCCCCCCCCCCC(O)CCCCC(=O)O[Si](C)(C)C(C)(C)C | 2669.7 | Semi standard non polar | 33892256 | 6-Hydroxyoctadecanoic acid,2TBDMS,isomer #1 | CCCCCCCCCCCCC(CCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 2911.1 | 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 - 6-Hydroxyoctadecanoic acid GC-MS (2 TMS) - 70eV, Positive | splash10-00fr-9232100000-014cdb71772611691dd5 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 6-Hydroxyoctadecanoic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-0f8d-4940000000-a383edfe5409865151f3 | 2017-11-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 6-Hydroxyoctadecanoic 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 - 6-Hydroxyoctadecanoic acid 10V, Positive-QTOF | splash10-001i-0091000000-4fc41adda310caf2d06f | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-Hydroxyoctadecanoic acid 20V, Positive-QTOF | splash10-05o0-4490000000-78e85d2bfe60de74acd8 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-Hydroxyoctadecanoic acid 40V, Positive-QTOF | splash10-0006-9420000000-61be65dd3422e18a1083 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-Hydroxyoctadecanoic acid 10V, Negative-QTOF | splash10-0002-0090000000-1a5fe9794ded8214497d | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-Hydroxyoctadecanoic acid 20V, Negative-QTOF | splash10-001j-0190000000-07d730212e67e4605676 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-Hydroxyoctadecanoic acid 40V, Negative-QTOF | splash10-0a4l-9530000000-1a1c81066f33f6b80408 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-Hydroxyoctadecanoic acid 10V, Negative-QTOF | splash10-001j-0090000000-06c6f0fde294ce5e630c | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-Hydroxyoctadecanoic acid 20V, Negative-QTOF | splash10-001j-1190000000-1193b0d507e4503ed6ae | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-Hydroxyoctadecanoic acid 40V, Negative-QTOF | splash10-05cu-9640000000-01cab8548a155b3474d4 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-Hydroxyoctadecanoic acid 10V, Positive-QTOF | splash10-0f89-2293000000-7d13aebc00d7ee0c2e4e | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-Hydroxyoctadecanoic acid 20V, Positive-QTOF | splash10-05o0-9581000000-0daf089d310e7505e6c9 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-Hydroxyoctadecanoic acid 40V, Positive-QTOF | splash10-0a4l-9000000000-cda0efa9fc5b684c974a | 2021-09-25 | Wishart Lab | View Spectrum |
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General References | - Yore MM, Syed I, Moraes-Vieira PM, Zhang T, Herman MA, Homan EA, Patel RT, Lee J, Chen S, Peroni OD, Dhaneshwar AS, Hammarstedt A, Smith U, McGraw TE, Saghatelian A, Kahn BB: Discovery of a class of endogenous mammalian lipids with anti-diabetic and anti-inflammatory effects. Cell. 2014 Oct 9;159(2):318-32. doi: 10.1016/j.cell.2014.09.035. [PubMed:25303528 ]
- Lopez-Bascon MA, Calderon-Santiago M, Priego-Capote F: Confirmatory and quantitative analysis of fatty acid esters of hydroxy fatty acids in serum by solid phase extraction coupled to liquid chromatography tandem mass spectrometry. Anal Chim Acta. 2016 Nov 2;943:82-88. doi: 10.1016/j.aca.2016.09.014. Epub 2016 Sep 20. [PubMed:27769381 ]
- 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 ]
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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