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 02:10:37 UTC |
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Update Date | 2022-03-07 03:17:55 UTC |
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HMDB ID | HMDB0062486 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid |
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Description | (6E,8E,10E,14E,17E)-5,12-dihydroxyicosa-6,8,10,14,17-pentaenoic acid 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 (6E,8E,10E,14E,17E)-5,12-dihydroxyicosa-6,8,10,14,17-pentaenoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). |
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Structure | [H]\C(CC)=C(\[H])C\C([H])=C(/[H])CC(O)C(\[H])=C(/[H])\C(\[H])=C(/[H])\C(\[H])=C(/[H])C(O)CCCC(O)=O InChI=1S/C20H30O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h3-4,6-11,14-15,18-19,21-22H,2,5,12-13,16-17H2,1H3,(H,23,24)/b4-3+,8-7+,9-6+,14-10+,15-11+ |
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Synonyms | Value | Source |
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(6E,8E,10E,14E,17E)-5,12-Dihydroxyicosa-6,8,10,14,17-pentaenoate | Generator | 5,12-Dihydroxy-6,8,10,14,17-eicosapentaenoate | Generator | Leukotriene b5 | HMDB | LTB 5 | HMDB |
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Chemical Formula | C20H30O4 |
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Average Molecular Weight | 334.456 |
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Monoisotopic Molecular Weight | 334.214409446 |
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IUPAC Name | (6E,8E,10E,14E,17E)-5,12-dihydroxyicosa-6,8,10,14,17-pentaenoic acid |
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Traditional Name | 5,12-DiHEPE |
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CAS Registry Number | Not Available |
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SMILES | [H]\C(CC)=C(\[H])C\C([H])=C(/[H])CC(O)C(\[H])=C(/[H])\C(\[H])=C(/[H])\C(\[H])=C(/[H])C(O)CCCC(O)=O |
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InChI Identifier | InChI=1S/C20H30O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h3-4,6-11,14-15,18-19,21-22H,2,5,12-13,16-17H2,1H3,(H,23,24)/b4-3+,8-7+,9-6+,14-10+,15-11+ |
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InChI Key | BISQPGCQOHLHQK-RUEGXZCXSA-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 | 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 | 0.016 g/l | ALOGPS | LogP | 4.68 | ALOGPS |
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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 IndicesUnderivatizedMetabolite | SMILES | Kovats RI Value | Column Type | Reference |
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5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid | [H]\C(CC)=C(\[H])C\C([H])=C(/[H])CC(O)C(\[H])=C(/[H])\C(\[H])=C(/[H])\C(\[H])=C(/[H])C(O)CCCC(O)=O | 4609.8 | Standard polar | 33892256 | 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid | [H]\C(CC)=C(\[H])C\C([H])=C(/[H])CC(O)C(\[H])=C(/[H])\C(\[H])=C(/[H])\C(\[H])=C(/[H])C(O)CCCC(O)=O | 2386.3 | Standard non polar | 33892256 | 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid | [H]\C(CC)=C(\[H])C\C([H])=C(/[H])CC(O)C(\[H])=C(/[H])\C(\[H])=C(/[H])\C(\[H])=C(/[H])C(O)CCCC(O)=O | 2735.7 | Semi standard non polar | 33892256 |
DerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid,1TMS,isomer #1 | CC/C=C/C/C=C/CC(/C=C/C=C/C=C/C(O)CCCC(=O)O)O[Si](C)(C)C | 2990.2 | Semi standard non polar | 33892256 | 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid,1TMS,isomer #2 | CC/C=C/C/C=C/CC(O)/C=C/C=C/C=C/C(CCCC(=O)O)O[Si](C)(C)C | 2996.0 | Semi standard non polar | 33892256 | 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid,1TMS,isomer #3 | CC/C=C/C/C=C/CC(O)/C=C/C=C/C=C/C(O)CCCC(=O)O[Si](C)(C)C | 2878.9 | Semi standard non polar | 33892256 | 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid,2TMS,isomer #1 | CC/C=C/C/C=C/CC(/C=C/C=C/C=C/C(CCCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C | 3022.2 | Semi standard non polar | 33892256 | 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid,2TMS,isomer #2 | CC/C=C/C/C=C/CC(/C=C/C=C/C=C/C(O)CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 2925.7 | Semi standard non polar | 33892256 | 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid,2TMS,isomer #3 | CC/C=C/C/C=C/CC(O)/C=C/C=C/C=C/C(CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 2932.0 | Semi standard non polar | 33892256 | 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid,3TMS,isomer #1 | CC/C=C/C/C=C/CC(/C=C/C=C/C=C/C(CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C | 2919.5 | Semi standard non polar | 33892256 | 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid,1TBDMS,isomer #1 | CC/C=C/C/C=C/CC(/C=C/C=C/C=C/C(O)CCCC(=O)O)O[Si](C)(C)C(C)(C)C | 3236.8 | Semi standard non polar | 33892256 | 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid,1TBDMS,isomer #2 | CC/C=C/C/C=C/CC(O)/C=C/C=C/C=C/C(CCCC(=O)O)O[Si](C)(C)C(C)(C)C | 3235.7 | Semi standard non polar | 33892256 | 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid,1TBDMS,isomer #3 | CC/C=C/C/C=C/CC(O)/C=C/C=C/C=C/C(O)CCCC(=O)O[Si](C)(C)C(C)(C)C | 3112.2 | Semi standard non polar | 33892256 | 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid,2TBDMS,isomer #1 | CC/C=C/C/C=C/CC(/C=C/C=C/C=C/C(CCCC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3467.2 | Semi standard non polar | 33892256 | 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid,2TBDMS,isomer #2 | CC/C=C/C/C=C/CC(/C=C/C=C/C=C/C(O)CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3392.4 | Semi standard non polar | 33892256 | 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid,2TBDMS,isomer #3 | CC/C=C/C/C=C/CC(O)/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 | 3401.3 | Semi standard non polar | 33892256 | 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid,3TBDMS,isomer #1 | CC/C=C/C/C=C/CC(/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)O[Si](C)(C)C(C)(C)C | 3660.0 | 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 - 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-066r-5976000000-1308051082500b532d7b | 2017-09-20 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid GC-MS (3 TMS) - 70eV, Positive | splash10-002u-9114550000-fb98f8ad419bf0e2f1eb | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5,12-dihydroxy-6,8,10,14,17-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 - 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid 10V, Positive-QTOF | splash10-014j-0089000000-945a81862277ca8ffccd | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid 20V, Positive-QTOF | splash10-00kk-3492000000-1307f5bf34685a04ff67 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid 40V, Positive-QTOF | splash10-0a4u-9550000000-dd3a21bd0ec9a9c3281b | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid 10V, Negative-QTOF | splash10-00lr-0029000000-aea24fc310a30c0083f4 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid 20V, Negative-QTOF | splash10-0159-2359000000-2767c62677c595b5c621 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid 40V, Negative-QTOF | splash10-0a4l-9440000000-c5ad6a89519cdea928ca | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid 10V, Negative-QTOF | splash10-0159-0019000000-ebe312919323a70b435d | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid 20V, Negative-QTOF | splash10-00lr-3449000000-33dea2da13cb74cad0bc | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid 40V, Negative-QTOF | splash10-059l-5391000000-da0f2fad428f71a9a01d | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid 10V, Positive-QTOF | splash10-00kb-0196000000-fb8a4628f13adee8bffa | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid 20V, Positive-QTOF | splash10-0002-1391000000-01dd8cbef267af45ff7a | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid 40V, Positive-QTOF | splash10-0ar0-9610000000-b9ceb4ac3bd3c9071f0a | 2021-09-25 | Wishart Lab | View Spectrum |
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