Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2008-09-15 09:55:10 UTC |
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Update Date | 2022-09-22 17:43:56 UTC |
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HMDB ID | HMDB0010214 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 19,20-DiHDPA |
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Description | 19,20-DiHDPA is one of the major metabolites produced when Docosahexaenoic acid (DHA) is incubated with NADPH-supplemented rat liver microsomes. Docosahexaenoic acid (DHA) is an essential fatty acid and the most abundant omega-3 fatty acid in neural tissues, especially in the retina and brain. DHA is also slowly metabolized by monkey seminal vesicles to 19,20-DiHDPA. The route of production likely proceeds through cytochrome P450-catalyzed epoxidation at the omega-3 double bond, followed by conversion to the vicinal diols by epoxide hydrolase. (PMID: 1742320 ). |
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Structure | CCC(O)C(O)C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O InChI=1S/C22H34O4/c1-2-20(23)21(24)18-16-14-12-10-8-6-4-3-5-7-9-11-13-15-17-19-22(25)26/h3-4,7-10,13-16,20-21,23-24H,2,5-6,11-12,17-19H2,1H3,(H,25,26)/b4-3-,9-7-,10-8-,15-13-,16-14- |
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Synonyms | Value | Source |
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19,20-DiHDoPE | ChEBI | 19,20-DiHDPE | ChEBI | 19,20-Dihydroxy-4Z,7Z,10Z,13Z,16Z-docosapentaenoic acid | ChEBI | 19,20-Dihydroxy-4Z,7Z,10Z,13Z,16Z-docosapentaenoate | Generator | (+/-)19,20-dihdope | HMDB | 19,20-Dihydroxydocosapentaenoate | HMDB | 19,20-Dihydroxydocosapentaenoic acid | HMDB | 19,20-DiHDPA | MeSH |
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Chemical Formula | C22H34O4 |
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Average Molecular Weight | 362.503 |
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Monoisotopic Molecular Weight | 362.245709576 |
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IUPAC Name | (4Z,7Z,10Z,13Z,16Z)-19,20-dihydroxydocosa-4,7,10,13,16-pentaenoic acid |
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Traditional Name | (4Z,7Z,10Z,13Z,16Z)-19,20-dihydroxydocosa-4,7,10,13,16-pentaenoic acid |
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CAS Registry Number | Not Available |
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SMILES | CCC(O)C(O)C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O |
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InChI Identifier | InChI=1S/C22H34O4/c1-2-20(23)21(24)18-16-14-12-10-8-6-4-3-5-7-9-11-13-15-17-19-22(25)26/h3-4,7-10,13-16,20-21,23-24H,2,5-6,11-12,17-19H2,1H3,(H,25,26)/b4-3-,9-7-,10-8-,15-13-,16-14- |
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InChI Key | FFXKPSNQCPNORO-MBYQGORISA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 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 | Very long-chain fatty acids |
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Alternative Parents | |
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Substituents | - Very long-chain fatty acid
- Hydroxy fatty acid
- Unsaturated fatty acid
- Secondary alcohol
- 1,2-diol
- 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 | |
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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 | Solid |
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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 | | 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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19,20-DiHDPA,1TMS,isomer #1 | CCC(O[Si](C)(C)C)C(O)C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O | 3114.8 | Semi standard non polar | 33892256 | 19,20-DiHDPA,1TMS,isomer #2 | CCC(O)C(C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O)O[Si](C)(C)C | 3120.8 | Semi standard non polar | 33892256 | 19,20-DiHDPA,1TMS,isomer #3 | CCC(O)C(O)C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O[Si](C)(C)C | 2949.1 | Semi standard non polar | 33892256 | 19,20-DiHDPA,2TMS,isomer #1 | CCC(O[Si](C)(C)C)C(C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O)O[Si](C)(C)C | 3032.6 | Semi standard non polar | 33892256 | 19,20-DiHDPA,2TMS,isomer #2 | CCC(O[Si](C)(C)C)C(O)C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O[Si](C)(C)C | 2961.6 | Semi standard non polar | 33892256 | 19,20-DiHDPA,2TMS,isomer #3 | CCC(O)C(C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 2951.0 | Semi standard non polar | 33892256 | 19,20-DiHDPA,3TMS,isomer #1 | CCC(O[Si](C)(C)C)C(C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 2931.0 | Semi standard non polar | 33892256 | 19,20-DiHDPA,1TBDMS,isomer #1 | CCC(O[Si](C)(C)C(C)(C)C)C(O)C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O | 3372.5 | Semi standard non polar | 33892256 | 19,20-DiHDPA,1TBDMS,isomer #2 | CCC(O)C(C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O)O[Si](C)(C)C(C)(C)C | 3368.8 | Semi standard non polar | 33892256 | 19,20-DiHDPA,1TBDMS,isomer #3 | CCC(O)C(O)C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O[Si](C)(C)C(C)(C)C | 3204.5 | Semi standard non polar | 33892256 | 19,20-DiHDPA,2TBDMS,isomer #1 | CCC(O[Si](C)(C)C(C)(C)C)C(C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O)O[Si](C)(C)C(C)(C)C | 3483.0 | Semi standard non polar | 33892256 | 19,20-DiHDPA,2TBDMS,isomer #2 | CCC(O[Si](C)(C)C(C)(C)C)C(O)C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O[Si](C)(C)C(C)(C)C | 3434.5 | Semi standard non polar | 33892256 | 19,20-DiHDPA,2TBDMS,isomer #3 | CCC(O)C(C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3428.8 | Semi standard non polar | 33892256 | 19,20-DiHDPA,3TBDMS,isomer #1 | CCC(O[Si](C)(C)C(C)(C)C)C(C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3639.3 | 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 - 19,20-DiHDPA GC-MS (Non-derivatized) - 70eV, Positive | splash10-0zfu-8249000000-7e742d8fd56a33203bdd | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 19,20-DiHDPA GC-MS (3 TMS) - 70eV, Positive | splash10-03di-3231490000-8e326e4de1b06da54e6a | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 19,20-DiHDPA 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 - 19,20-DiHDPA 10V, Positive-QTOF | splash10-0002-0019000000-29bb8e624c9a8d7dd286 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 19,20-DiHDPA 20V, Positive-QTOF | splash10-056s-2094000000-1749ffa613a37fc785e0 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 19,20-DiHDPA 40V, Positive-QTOF | splash10-01r6-6390000000-fc91fa813229e0592fca | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 19,20-DiHDPA 10V, Negative-QTOF | splash10-03di-0009000000-3d99a1a7ed4531ad8cf6 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 19,20-DiHDPA 20V, Negative-QTOF | splash10-0btc-4039000000-b0d4491c9320a09cc67c | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 19,20-DiHDPA 40V, Negative-QTOF | splash10-0a4i-9011000000-fc9f8b3372dc20645e38 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 19,20-DiHDPA 10V, Negative-QTOF | splash10-03di-0009000000-70804a01cf218984bcbd | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 19,20-DiHDPA 20V, Negative-QTOF | splash10-0a4i-6049000000-bcac3b983044ec809721 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 19,20-DiHDPA 40V, Negative-QTOF | splash10-052r-9073000000-cc0870715c7efeb917a8 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 19,20-DiHDPA 10V, Positive-QTOF | splash10-002b-0029000000-11ea7ffba8e57db6a373 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 19,20-DiHDPA 20V, Positive-QTOF | splash10-004j-2369000000-9d469005a5dce85aa530 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 19,20-DiHDPA 40V, Positive-QTOF | splash10-0159-5920000000-a4e85897e8df32a22287 | 2021-09-22 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | - Membrane (predicted from logP)
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 0.00123 +/- 0.000389 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 0.00664 +/- 0.000469 uM | Adult (>18 years old) | Not Specified | Normal | | details | Blood | Detected and Quantified | 0.000805 +/- 0.00042 uM | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Urine | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Cancer patients undergoing total body irradiation | | details |
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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 | FDB027369 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 17220827 |
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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 | 16061148 |
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PDB ID | Not Available |
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ChEBI ID | 72657 |
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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 | - Oliw EH, Sprecher HW: Metabolism of polyunsaturated (n-3) fatty acids by monkey seminal vesicles: isolation and biosynthesis of omega-3 epoxides. Biochim Biophys Acta. 1991 Nov 27;1086(3):287-94. [PubMed:1742320 ]
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