Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2008-09-16 13:20:24 UTC |
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Update Date | 2022-03-07 02:50:54 UTC |
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HMDB ID | HMDB0010410 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Resolvin E1 |
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Description | Resolvin E1 is a resolvin, a bioactive oxygenated product of EPA (eicosapentaenoic acid). It is a inflammation-resolving lipid mediator. RvE1 reduces neutrophil hyper-function, it also prevents the initiation and progression of tissue destruction (PMID: 16373400 ). RvE1, can also act as a host response modulator in the control of the inflammatory diseases that also involve bone loss such as periodontitis and arthritis. RvE1 has been shown to display specific binding sites on human neutrophils with an apparent Kd of 47 nM (PMID: 15753205 ; 16373400 ). RvE1 is a potent modulator of leukocytes as well as selective platelet responses in blood and platelet-rich plasma (PMID: 18480426 ). |
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Structure | CCC(O)\C=C\C=C/CC(O)\C=C\C=C\C=C/C(O)CCCC(O)=O InChI=1S/C20H30O5/c1-2-17(21)11-8-5-9-14-18(22)12-6-3-4-7-13-19(23)15-10-16-20(24)25/h3-9,11-13,17-19,21-23H,2,10,14-16H2,1H3,(H,24,25)/b4-3+,9-5-,11-8+,12-6+,13-7- |
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Synonyms | Value | Source |
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5S,12R,18R-Trihydroxy-6Z,8E,10E,14Z,16E-epa | HMDB | ResolvinE1 | HMDB | RvE1 | HMDB | 5S,12R,18R-Trihydroxy-6Z,8E,10E,14Z,16E-eicosapentaenoic acid | HMDB | (6Z,8E,10E,14Z,16E)-5,12,18-Trihydroxyicosa-6,8,10,14,16-pentaenoate | HMDB | Resolvin e1 | MeSH |
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Chemical Formula | C20H30O5 |
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Average Molecular Weight | 350.4492 |
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Monoisotopic Molecular Weight | 350.20932407 |
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IUPAC Name | (6Z,8E,10E,14Z,16E)-5,12,18-trihydroxyicosa-6,8,10,14,16-pentaenoic acid |
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Traditional Name | RvE1 |
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CAS Registry Number | Not Available |
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SMILES | CCC(O)\C=C\C=C/CC(O)\C=C\C=C\C=C/C(O)CCCC(O)=O |
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InChI Identifier | InChI=1S/C20H30O5/c1-2-17(21)11-8-5-9-14-18(22)12-6-3-4-7-13-19(23)15-10-16-20(24)25/h3-9,11-13,17-19,21-23H,2,10,14-16H2,1H3,(H,24,25)/b4-3+,9-5-,11-8+,12-6+,13-7- |
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InChI Key | AOPOCGPBAIARAV-WEKRNNBPSA-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
- Polyol
- Organic oxide
- Organic oxygen compound
- Hydrocarbon derivative
- Carbonyl group
- Organooxygen compound
- 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 | | 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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Resolvin E1,1TMS,isomer #1 | CCC(/C=C/C=C\CC(O)/C=C/C=C/C=C\C(O)CCCC(=O)O)O[Si](C)(C)C | 3197.1 | Semi standard non polar | 33892256 | Resolvin E1,1TMS,isomer #2 | CCC(O)/C=C/C=C\CC(/C=C/C=C/C=C\C(O)CCCC(=O)O)O[Si](C)(C)C | 3208.2 | Semi standard non polar | 33892256 | Resolvin E1,1TMS,isomer #3 | CCC(O)/C=C/C=C\CC(O)/C=C/C=C/C=C\C(CCCC(=O)O)O[Si](C)(C)C | 3213.7 | Semi standard non polar | 33892256 | Resolvin E1,1TMS,isomer #4 | CCC(O)/C=C/C=C\CC(O)/C=C/C=C/C=C\C(O)CCCC(=O)O[Si](C)(C)C | 3108.3 | Semi standard non polar | 33892256 | Resolvin E1,2TMS,isomer #1 | CCC(/C=C/C=C\CC(/C=C/C=C/C=C\C(O)CCCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C | 3234.9 | Semi standard non polar | 33892256 | Resolvin E1,2TMS,isomer #2 | CCC(/C=C/C=C\CC(O)/C=C/C=C/C=C\C(CCCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C | 3228.2 | Semi standard non polar | 33892256 | Resolvin E1,2TMS,isomer #3 | CCC(/C=C/C=C\CC(O)/C=C/C=C/C=C\C(O)CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 3129.1 | Semi standard non polar | 33892256 | Resolvin E1,2TMS,isomer #4 | CCC(O)/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 | 3241.4 | Semi standard non polar | 33892256 | Resolvin E1,2TMS,isomer #5 | CCC(O)/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 | 3137.0 | Semi standard non polar | 33892256 | Resolvin E1,2TMS,isomer #6 | CCC(O)/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 | 3140.5 | Semi standard non polar | 33892256 | Resolvin E1,3TMS,isomer #1 | CCC(/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)O[Si](C)(C)C | 3193.6 | Semi standard non polar | 33892256 | Resolvin E1,3TMS,isomer #2 | CCC(/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)O[Si](C)(C)C | 3123.0 | Semi standard non polar | 33892256 | Resolvin E1,3TMS,isomer #3 | CCC(/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)O[Si](C)(C)C | 3117.5 | Semi standard non polar | 33892256 | Resolvin E1,3TMS,isomer #4 | CCC(O)/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 | 3114.3 | Semi standard non polar | 33892256 | Resolvin E1,4TMS,isomer #1 | CCC(/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)O[Si](C)(C)C | 3104.9 | Semi standard non polar | 33892256 | Resolvin E1,1TBDMS,isomer #1 | CCC(/C=C/C=C\CC(O)/C=C/C=C/C=C\C(O)CCCC(=O)O)O[Si](C)(C)C(C)(C)C | 3442.2 | Semi standard non polar | 33892256 | Resolvin E1,1TBDMS,isomer #2 | CCC(O)/C=C/C=C\CC(/C=C/C=C/C=C\C(O)CCCC(=O)O)O[Si](C)(C)C(C)(C)C | 3446.9 | Semi standard non polar | 33892256 | Resolvin E1,1TBDMS,isomer #3 | CCC(O)/C=C/C=C\CC(O)/C=C/C=C/C=C\C(CCCC(=O)O)O[Si](C)(C)C(C)(C)C | 3448.0 | Semi standard non polar | 33892256 | Resolvin E1,1TBDMS,isomer #4 | CCC(O)/C=C/C=C\CC(O)/C=C/C=C/C=C\C(O)CCCC(=O)O[Si](C)(C)C(C)(C)C | 3353.6 | Semi standard non polar | 33892256 | Resolvin E1,2TBDMS,isomer #1 | CCC(/C=C/C=C\CC(/C=C/C=C/C=C\C(O)CCCC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3696.1 | Semi standard non polar | 33892256 | Resolvin E1,2TBDMS,isomer #2 | CCC(/C=C/C=C\CC(O)/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 | 3696.4 | Semi standard non polar | 33892256 | Resolvin E1,2TBDMS,isomer #3 | CCC(/C=C/C=C\CC(O)/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 | 3615.1 | Semi standard non polar | 33892256 | Resolvin E1,2TBDMS,isomer #4 | CCC(O)/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 | 3698.1 | Semi standard non polar | 33892256 | Resolvin E1,2TBDMS,isomer #5 | CCC(O)/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 | 3614.0 | Semi standard non polar | 33892256 | Resolvin E1,2TBDMS,isomer #6 | CCC(O)/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 | 3627.2 | Semi standard non polar | 33892256 | Resolvin E1,3TBDMS,isomer #1 | CCC(/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)O[Si](C)(C)C(C)(C)C | 3936.5 | Semi standard non polar | 33892256 | Resolvin E1,3TBDMS,isomer #2 | CCC(/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)O[Si](C)(C)C(C)(C)C | 3879.7 | Semi standard non polar | 33892256 | Resolvin E1,3TBDMS,isomer #3 | CCC(/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)O[Si](C)(C)C(C)(C)C | 3884.9 | Semi standard non polar | 33892256 | Resolvin E1,3TBDMS,isomer #4 | CCC(O)/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 | 3878.2 | Semi standard non polar | 33892256 | Resolvin E1,4TBDMS,isomer #1 | CCC(/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)O[Si](C)(C)C(C)(C)C | 4083.7 | 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 - Resolvin E1 GC-MS (Non-derivatized) - 70eV, Positive | splash10-001i-5379000000-0d3673588a0031b08acc | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Resolvin E1 GC-MS (4 TMS) - 70eV, Positive | splash10-00bc-8210967000-0976f920f1060120fe1a | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Resolvin E1 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 - Resolvin E1 10V, Positive-QTOF | splash10-0159-0009000000-e252805b2e27bc3c1cab | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Resolvin E1 20V, Positive-QTOF | splash10-014i-1389000000-7a8992692251f6c49531 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Resolvin E1 40V, Positive-QTOF | splash10-00y4-5290000000-d748020e8e502628d78e | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Resolvin E1 10V, Negative-QTOF | splash10-000t-0009000000-ffa4ac439ea8272ee9e1 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Resolvin E1 20V, Negative-QTOF | splash10-001j-1139000000-78e4bddeed4d6e6cde6d | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Resolvin E1 40V, Negative-QTOF | splash10-0a4l-9240000000-efa75cec2a9f54c6c4ed | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Resolvin E1 10V, Negative-QTOF | splash10-0002-0009000000-4c1cea37c93d8f998b31 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Resolvin E1 20V, Negative-QTOF | splash10-0532-3169000000-ffe197b251029c976235 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Resolvin E1 40V, Negative-QTOF | splash10-0mdm-8196000000-4e0efceab5d344aa2cf8 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Resolvin E1 10V, Positive-QTOF | splash10-0159-0029000000-ba12b81c9fae9ddea0db | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Resolvin E1 20V, Positive-QTOF | splash10-014i-0179000000-f204b81647f9fc608b77 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Resolvin E1 40V, Positive-QTOF | splash10-00vi-9760000000-4e6727f754b2e1552a18 | 2021-09-25 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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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 | 0.001 +/- 0.000234 uM | Adult (>18 years old) | Not Specified | Normal | | details | Blood | Detected and Quantified | 0.001 +/- 0.00023 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 0.000521 +/- 0.00098 uM | Adult (>18 years old) | Both | Normal | | details |
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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 | FDB027561 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 35032053 |
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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 | 25063347 |
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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 | - Hasturk H, Kantarci A, Ohira T, Arita M, Ebrahimi N, Chiang N, Petasis NA, Levy BD, Serhan CN, Van Dyke TE: RvE1 protects from local inflammation and osteoclast- mediated bone destruction in periodontitis. FASEB J. 2006 Feb;20(2):401-3. Epub 2005 Dec 22. [PubMed:16373400 ]
- Arita M, Bianchini F, Aliberti J, Sher A, Chiang N, Hong S, Yang R, Petasis NA, Serhan CN: Stereochemical assignment, antiinflammatory properties, and receptor for the omega-3 lipid mediator resolvin E1. J Exp Med. 2005 Mar 7;201(5):713-22. [PubMed:15753205 ]
- Dona M, Fredman G, Schwab JM, Chiang N, Arita M, Goodarzi A, Cheng G, von Andrian UH, Serhan CN: Resolvin E1, an EPA-derived mediator in whole blood, selectively counterregulates leukocytes and platelets. Blood. 2008 Aug 1;112(3):848-55. doi: 10.1182/blood-2007-11-122598. Epub 2008 May 14. [PubMed:18480426 ]
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