Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2006-08-14 01:55:43 UTC |
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Update Date | 2022-09-22 17:43:53 UTC |
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HMDB ID | HMDB0004705 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 12,13-DHOME |
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Description | 12,13-DHOME (CAS: 263399-35-5), also known as 12,13-dihydroxy-9-octadecenoic acid or 12,13-DiHOME, is the epoxide hydrolase metabolite of the leukotoxin 12,13-EpOME. 12,13-EpOME acts as a protoxin, with the corresponding epoxide hydrolase 12,13-DHOME specifically exerting toxicity. Both the EpOME and the DHOME are shown to have neutrophil chemotactic activity. 12,13-DHOME suppress the neutrophil respiratory burst by a mechanism distinct from that of respiratory burst inhibitors such as cyclosporin H or lipoxin A4, which inhibit multiple aspects of neutrophil activation. 12,13-DHOME is a derivative of the linoleic acid diol that has been reported to be toxic in human tissue preparations. 12,13-DHOME is a naturally occurring proliferator-activated receptor (PPAR) gamma2 ligand, which stimulates adipocytes and inhibits osteoblast differentiation (PMID: 17435320 , 12021203 , 12127265 ). |
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Structure | CCCCC[C@H](O)[C@@H](O)C\C=C/CCCCCCCC(O)=O InChI=1S/C18H34O4/c1-2-3-10-13-16(19)17(20)14-11-8-6-4-5-7-9-12-15-18(21)22/h8,11,16-17,19-20H,2-7,9-10,12-15H2,1H3,(H,21,22)/b11-8-/t16-,17-/m0/s1 |
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Synonyms | Value | Source |
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12,13-Dihydroxyoleate | HMDB | (-)-Threo-12,13-dihydroxyoleic acid | HMDB | (9Z)-12,13-Dihydroxy-9-octadecenoic acid | HMDB | (9Z,12S,13S)-12,13-Dihydroxy-9-octadecenoic acid | HMDB | 12,13-DiHOME | HMDB | FA(18:1(9Z,12S,13S)) | HMDB | FA(18:1(9Z,12S-OH,13S-OH)) | HMDB | 12,13-DHOME | HMDB |
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Chemical Formula | C18H34O4 |
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Average Molecular Weight | 314.466 |
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Monoisotopic Molecular Weight | 314.245709575 |
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IUPAC Name | (9Z,12S,13S)-12,13-dihydroxyoctadec-9-enoic acid |
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Traditional Name | (9Z,12S,13S)-12,13-dihydroxyoctadec-9-enoic acid |
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CAS Registry Number | 7293-40-5 |
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SMILES | CCCCC[C@H](O)[C@@H](O)C\C=C/CCCCCCCC(O)=O |
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InChI Identifier | InChI=1S/C18H34O4/c1-2-3-10-13-16(19)17(20)14-11-8-6-4-5-7-9-12-15-18(21)22/h8,11,16-17,19-20H,2-7,9-10,12-15H2,1H3,(H,21,22)/b11-8-/t16-,17-/m0/s1 |
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InChI Key | CQSLTKIXAJTQGA-BTDPBSJTSA-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
- 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 | Not Available |
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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 | |
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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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12,13-DHOME,1TMS,isomer #1 | CCCCC[C@H](O[Si](C)(C)C)[C@@H](O)C/C=C\CCCCCCCC(=O)O | 2513.5 | Semi standard non polar | 33892256 | 12,13-DHOME,1TMS,isomer #2 | CCCCC[C@H](O)[C@H](C/C=C\CCCCCCCC(=O)O)O[Si](C)(C)C | 2529.7 | Semi standard non polar | 33892256 | 12,13-DHOME,1TMS,isomer #3 | CCCCC[C@H](O)[C@@H](O)C/C=C\CCCCCCCC(=O)O[Si](C)(C)C | 2537.0 | Semi standard non polar | 33892256 | 12,13-DHOME,2TMS,isomer #1 | CCCCC[C@H](O[Si](C)(C)C)[C@H](C/C=C\CCCCCCCC(=O)O)O[Si](C)(C)C | 2532.7 | Semi standard non polar | 33892256 | 12,13-DHOME,2TMS,isomer #2 | CCCCC[C@H](O[Si](C)(C)C)[C@@H](O)C/C=C\CCCCCCCC(=O)O[Si](C)(C)C | 2545.9 | Semi standard non polar | 33892256 | 12,13-DHOME,2TMS,isomer #3 | CCCCC[C@H](O)[C@H](C/C=C\CCCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 2554.9 | Semi standard non polar | 33892256 | 12,13-DHOME,3TMS,isomer #1 | CCCCC[C@H](O[Si](C)(C)C)[C@H](C/C=C\CCCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 2542.8 | Semi standard non polar | 33892256 | 12,13-DHOME,1TBDMS,isomer #1 | CCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C/C=C\CCCCCCCC(=O)O | 2754.6 | Semi standard non polar | 33892256 | 12,13-DHOME,1TBDMS,isomer #2 | CCCCC[C@H](O)[C@H](C/C=C\CCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C | 2757.4 | Semi standard non polar | 33892256 | 12,13-DHOME,1TBDMS,isomer #3 | CCCCC[C@H](O)[C@@H](O)C/C=C\CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C | 2779.6 | Semi standard non polar | 33892256 | 12,13-DHOME,2TBDMS,isomer #1 | CCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@H](C/C=C\CCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C | 3027.1 | Semi standard non polar | 33892256 | 12,13-DHOME,2TBDMS,isomer #2 | CCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C/C=C\CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C | 3020.1 | Semi standard non polar | 33892256 | 12,13-DHOME,2TBDMS,isomer #3 | CCCCC[C@H](O)[C@H](C/C=C\CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3038.6 | Semi standard non polar | 33892256 | 12,13-DHOME,3TBDMS,isomer #1 | CCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@H](C/C=C\CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3276.0 | 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 - 12,13-DHOME 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 - 12,13-DHOME 10V, Negative-QTOF | splash10-03di-0119000000-4c868de0f3de6c07f549 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 12,13-DHOME 20V, Negative-QTOF | splash10-03dj-3985000000-11f56948c3f5b836b850 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 12,13-DHOME 40V, Negative-QTOF | splash10-0002-9510000000-44b29fc1dc61e8abffec | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 12,13-DHOME 10V, Positive-QTOF | splash10-00mk-0492000000-08dc8525353e9939cf8d | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 12,13-DHOME 20V, Positive-QTOF | splash10-00pj-9650000000-e6462e60e7ab620364b5 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 12,13-DHOME 40V, Positive-QTOF | splash10-0apl-9200000000-bd2c48bf7ac9bd897d4a | 2021-09-25 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum |
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