Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2017-03-21 06:15:30 UTC |
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Update Date | 2022-03-07 03:17:54 UTC |
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HMDB ID | HMDB0062408 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid |
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Description | 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid is classified as a member of the Hydroxyeicosapentaenoic acids. Hydroxyeicosapentaenoic acids are eicosanoic acids with an attached hydroxyl group and five CC double bonds. 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid is considered to be practically insoluble (in water) and acidic. 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid is an eicosanoid lipid molecule |
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Structure | [H]\C(CC)=C(/[H])C\C([H])=C(\[H])C\C([H])=C(\[H])C\C([H])=C(\[H])/C(/[H])=C(\[H])[C@@]([H])(O)CCCC(O)=O InChI=1S/C20H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(21)17-15-18-20(22)23/h3-4,6-7,9-10,12-14,16,19,21H,2,5,8,11,15,17-18H2,1H3,(H,22,23)/b4-3-,7-6-,10-9-,13-12-,16-14+/t19-/m1/s1 |
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Synonyms | Value | Source |
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5S-Hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoate | Generator |
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Chemical Formula | C20H30O3 |
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Average Molecular Weight | 318.457 |
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Monoisotopic Molecular Weight | 318.219494826 |
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IUPAC Name | (5S,6E,8Z,11Z,14Z,17Z)-5-hydroxyicosa-6,8,11,14,17-pentaenoic acid |
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Traditional Name | 5S-hepe |
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CAS Registry Number | Not Available |
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SMILES | [H]\C(CC)=C(/[H])C\C([H])=C(\[H])C\C([H])=C(\[H])C\C([H])=C(\[H])/C(/[H])=C(\[H])[C@@]([H])(O)CCCC(O)=O |
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InChI Identifier | InChI=1S/C20H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(21)17-15-18-20(22)23/h3-4,6-7,9-10,12-14,16,19,21H,2,5,8,11,15,17-18H2,1H3,(H,22,23)/b4-3-,7-6-,10-9-,13-12-,16-14+/t19-/m1/s1 |
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InChI Key | FTAGQROYQYQRHF-GHWNLOBHSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as hydroxyeicosapentaenoic acids. These are eicosanoic acids with an attached hydroxyl group and five CC double bonds. |
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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 | Eicosanoids |
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Direct Parent | Hydroxyeicosapentaenoic acids |
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Alternative Parents | |
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Substituents | - Hydroxyeicosapentaenoic acid
- Long-chain fatty acid
- Hydroxy fatty acid
- Fatty acid
- Unsaturated fatty acid
- Secondary alcohol
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Organic oxide
- Organic oxygen compound
- Alcohol
- Hydrocarbon derivative
- Carbonyl group
- Organooxygen compound
- 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 | |
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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 | 0.0029 g/l | ALOGPS | LogP | 5.54 | ALOGPS |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedMetabolite | SMILES | Kovats RI Value | Column Type | Reference |
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5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid | [H]\C(CC)=C(/[H])C\C([H])=C(\[H])C\C([H])=C(\[H])C\C([H])=C(\[H])/C(/[H])=C(\[H])[C@@]([H])(O)CCCC(O)=O | 4276.1 | Standard polar | 33892256 | 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid | [H]\C(CC)=C(/[H])C\C([H])=C(\[H])C\C([H])=C(\[H])C\C([H])=C(\[H])/C(/[H])=C(\[H])[C@@]([H])(O)CCCC(O)=O | 2366.5 | Standard non polar | 33892256 | 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid | [H]\C(CC)=C(/[H])C\C([H])=C(\[H])C\C([H])=C(\[H])C\C([H])=C(\[H])/C(/[H])=C(\[H])[C@@]([H])(O)CCCC(O)=O | 2609.2 | Semi standard non polar | 33892256 |
DerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid,1TMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C | 2767.9 | Semi standard non polar | 33892256 | 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid,1TMS,isomer #2 | CC/C=C\C/C=C\C/C=C\C/C=C\C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C | 2639.4 | Semi standard non polar | 33892256 | 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid,2TMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\C=C\[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 2718.3 | Semi standard non polar | 33892256 | 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid,1TBDMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C | 3014.0 | Semi standard non polar | 33892256 | 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid,1TBDMS,isomer #2 | CC/C=C\C/C=C\C/C=C\C/C=C\C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C | 2889.0 | Semi standard non polar | 33892256 | 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid,2TBDMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\C=C\[C@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3194.1 | Semi standard non polar | 33892256 |
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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 - 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-0udi-5394000000-3c896430e353b0ced0db | 2017-09-20 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid GC-MS (2 TMS) - 70eV, Positive | splash10-0umj-8209200000-58c4694ad173b557f3c5 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic 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 - 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid 10V, Positive-QTOF | splash10-0udi-0149000000-dfe33b6babf270b34752 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid 20V, Positive-QTOF | splash10-0udu-5693000000-fb5c896d30ace0c553d8 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid 40V, Positive-QTOF | splash10-000l-9880000000-5d7665b416fe42c2c371 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid 10V, Negative-QTOF | splash10-014i-0069000000-023fef6c61163c7bc817 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid 20V, Negative-QTOF | splash10-00kb-2093000000-e62551450dc40c949d52 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid 40V, Negative-QTOF | splash10-0a4l-9160000000-b435064b3bb6876f2d7b | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid 10V, Positive-QTOF | splash10-0udi-1559000000-04ab13d626af1b826444 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid 20V, Positive-QTOF | splash10-0kha-4941000000-506babd9193b9c28a976 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid 40V, Positive-QTOF | splash10-00nf-9500000000-1b5d43f5a2984de18947 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid 10V, Negative-QTOF | splash10-014i-0019000000-c5853cf372543090df7d | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid 20V, Negative-QTOF | splash10-066r-5297000000-8a9ce241f524b80527f1 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid 40V, Negative-QTOF | splash10-0a4m-9840000000-d55d013e9ad27e3eb651 | 2021-09-24 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | Not Available |
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Biospecimen Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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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 | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | Not Available |
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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 | 5283193 |
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PDB ID | Not Available |
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ChEBI ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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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 | - 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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