Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2017-03-23 04:41:29 UTC |
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Update Date | 2022-03-07 03:17:57 UTC |
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HMDB ID | HMDB0062614 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 5,20-DiHETE |
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Description | (6E,8E,11E,14E)-5,20-dihydroxyicosa-6,8,11,14-tetraenoic acid belongs to the class of organic compounds known as hydroxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroxyl group and four CC double bonds (6E,8E,11E,14E)-5,20-dihydroxyicosa-6,8,11,14-tetraenoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). |
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Structure | [H]\C(CCCCCO)=C(\[H])C\C([H])=C(/[H])C\C([H])=C(/[H])\C(\[H])=C(/[H])C(O)CCCC(O)=O InChI=1S/C20H32O4/c21-18-13-11-9-7-5-3-1-2-4-6-8-10-12-15-19(22)16-14-17-20(23)24/h2-5,8,10,12,15,19,21-22H,1,6-7,9,11,13-14,16-18H2,(H,23,24)/b4-2+,5-3+,10-8+,15-12+ |
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Synonyms | Value | Source |
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(6E,8E,11E,14E)-5,20-Dihydroxyicosa-6,8,11,14-tetraenoate | Generator | 5,20-Dihydroxy-6,8,11,14-eicosatetraenoic acid | HMDB |
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Chemical Formula | C20H32O4 |
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Average Molecular Weight | 336.472 |
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Monoisotopic Molecular Weight | 336.23005951 |
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IUPAC Name | (6E,8E,11E,14E)-5,20-dihydroxyicosa-6,8,11,14-tetraenoic acid |
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Traditional Name | (6E,8E,11E,14E)-5,20-dihydroxyicosa-6,8,11,14-tetraenoic acid |
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CAS Registry Number | Not Available |
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SMILES | [H]\C(CCCCCO)=C(\[H])C\C([H])=C(/[H])C\C([H])=C(/[H])\C(\[H])=C(/[H])C(O)CCCC(O)=O |
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InChI Identifier | InChI=1S/C20H32O4/c21-18-13-11-9-7-5-3-1-2-4-6-8-10-12-15-19(22)16-14-17-20(23)24/h2-5,8,10,12,15,19,21-22H,1,6-7,9,11,13-14,16-18H2,(H,23,24)/b4-2+,5-3+,10-8+,15-12+ |
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InChI Key | IWYJGYZCHKEPCK-BHCYBMAPSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as hydroxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroxyl group and four 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 | Hydroxyeicosatetraenoic acids |
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Alternative Parents | |
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Substituents | - Hydroxyeicosatetraenoic acid
- Long-chain fatty acid
- Hydroxy fatty acid
- Fatty acid
- Unsaturated fatty acid
- Secondary alcohol
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Alcohol
- Carbonyl group
- Organooxygen compound
- Primary 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 | 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 | 0.013 g/l | ALOGPS | LogP | 5.23 | 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 IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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5,20-DiHETE,1TMS,isomer #1 | C[Si](C)(C)OCCCCC/C=C/C/C=C/C/C=C/C=C/C(O)CCCC(=O)O | 3014.4 | Semi standard non polar | 33892256 | 5,20-DiHETE,1TMS,isomer #2 | C[Si](C)(C)OC(/C=C/C=C/C/C=C/C/C=C/CCCCCO)CCCC(=O)O | 3000.9 | Semi standard non polar | 33892256 | 5,20-DiHETE,1TMS,isomer #3 | C[Si](C)(C)OC(=O)CCCC(O)/C=C/C=C/C/C=C/C/C=C/CCCCCO | 2883.7 | Semi standard non polar | 33892256 | 5,20-DiHETE,2TMS,isomer #1 | C[Si](C)(C)OCCCCC/C=C/C/C=C/C/C=C/C=C/C(CCCC(=O)O)O[Si](C)(C)C | 3067.5 | Semi standard non polar | 33892256 | 5,20-DiHETE,2TMS,isomer #2 | C[Si](C)(C)OCCCCC/C=C/C/C=C/C/C=C/C=C/C(O)CCCC(=O)O[Si](C)(C)C | 2952.3 | Semi standard non polar | 33892256 | 5,20-DiHETE,2TMS,isomer #3 | C[Si](C)(C)OC(=O)CCCC(/C=C/C=C/C/C=C/C/C=C/CCCCCO)O[Si](C)(C)C | 2956.8 | Semi standard non polar | 33892256 | 5,20-DiHETE,3TMS,isomer #1 | C[Si](C)(C)OCCCCC/C=C/C/C=C/C/C=C/C=C/C(CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 2968.0 | Semi standard non polar | 33892256 | 5,20-DiHETE,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OCCCCC/C=C/C/C=C/C/C=C/C=C/C(O)CCCC(=O)O | 3248.3 | Semi standard non polar | 33892256 | 5,20-DiHETE,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(/C=C/C=C/C/C=C/C/C=C/CCCCCO)CCCC(=O)O | 3243.0 | Semi standard non polar | 33892256 | 5,20-DiHETE,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC(=O)CCCC(O)/C=C/C=C/C/C=C/C/C=C/CCCCCO | 3119.5 | Semi standard non polar | 33892256 | 5,20-DiHETE,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OCCCCC/C=C/C/C=C/C/C=C/C=C/C(CCCC(=O)O)O[Si](C)(C)C(C)(C)C | 3514.2 | Semi standard non polar | 33892256 | 5,20-DiHETE,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OCCCCC/C=C/C/C=C/C/C=C/C=C/C(O)CCCC(=O)O[Si](C)(C)C(C)(C)C | 3414.7 | Semi standard non polar | 33892256 | 5,20-DiHETE,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC(=O)CCCC(/C=C/C=C/C/C=C/C/C=C/CCCCCO)O[Si](C)(C)C(C)(C)C | 3420.0 | Semi standard non polar | 33892256 | 5,20-DiHETE,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OCCCCC/C=C/C/C=C/C/C=C/C=C/C(CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3722.1 | 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 - 5,20-DiHETE GC-MS (Non-derivatized) - 70eV, Positive | splash10-014i-3293000000-6bdfcb5d83a0545aa223 | 2017-09-20 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5,20-DiHETE GC-MS (3 TMS) - 70eV, Positive | splash10-007c-9516670000-b06d7cd355593c37aef6 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5,20-DiHETE GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5,20-DiHETE 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 - 5,20-DiHETE 10V, Positive-QTOF | splash10-0gb9-0019000000-21eefe82acbdccaa4f7b | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,20-DiHETE 20V, Positive-QTOF | splash10-0v4i-2197000000-10da2feeb13adcfcd334 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,20-DiHETE 40V, Positive-QTOF | splash10-0a4l-6390000000-8e6673a446aae98113ec | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,20-DiHETE 10V, Negative-QTOF | splash10-00kr-0019000000-963466c70ff34b492aec | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,20-DiHETE 20V, Negative-QTOF | splash10-00kr-1079000000-c0f038ed916d4fa76cc2 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,20-DiHETE 40V, Negative-QTOF | splash10-0a4l-9060000000-8444959d0e34c0289110 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,20-DiHETE 10V, Negative-QTOF | splash10-000i-0009000000-069b6c9f1e0e1ca41bb7 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,20-DiHETE 20V, Negative-QTOF | splash10-00kr-3049000000-ab59dd91669e4a63ebb8 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,20-DiHETE 40V, Negative-QTOF | splash10-0a4u-6291000000-855057a5fd79ba936c44 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,20-DiHETE 10V, Positive-QTOF | splash10-0gb9-0239000000-7873079435d00d5dafbe | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,20-DiHETE 20V, Positive-QTOF | splash10-0gb9-5689000000-fbe570cbdbb0574af89d | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,20-DiHETE 40V, Positive-QTOF | splash10-00lu-6900000000-47bfa4d1dda384aa97de | 2021-09-22 | 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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| Not Available |
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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 | 6439103 |
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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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