Record Information |
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Version | 1.0 |
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Creation date | 2011-09-21 01:50:39 UTC |
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Update date | 2015-07-21 06:59:38 UTC |
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Primary ID | FDB029137 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | 15-Oxo-lipoxin A4 |
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Description | 15-oxo-lipoxin A4 is a lipoxin derivative
Lipoxins (LXs) and aspirin-triggered Lipoxin (ATL) are trihydroxytetraene-containing eicosanoids generated from arachidonic acid that are distinct in structure, formation, and function from the many other proinflammatory lipid-derived mediators. These endogenous eicosanoids have now emerged as founding members of the first class of lipid/chemical mediators involved in the resolution of the inflammatory response. Lipoxin A4 (LXA4), ATL, and their metabolic stable analogs elicit cellular responses and regulate leukocyte trafficking in vivo by activating the specific receptor, ALX. Many of the eicosanoids derived from arachidonic acid (AA2), including prostaglandins (PGs) and leukotrienes (LTs), play important roles as local mediators exerting a wide range of actions relevant in immune hypersensitivity and inflammation. However, recent observations indicate that other agents derived from the lipoxygenase (LO) pathways are formed and play a key role in initiating the resolution of acute inflammation. This phenomenon is an active process that is governed by specific lipid mediators and involves a series of well-orchestrated temporal events. Thus, potent locally released mediators serve as checkpoint controllers of inflammation.
In addition to the well-appreciated ability of aspirin to inhibit PGs, aspirin also acetylates cyclooxygenase (COX)-2, triggering the formation of a 15-epimeric form of lipoxins, termed aspirin-triggered LXA4 (ATL). These eicosanoids (i.e., LXA4 and ATL) with a unique trihydroxytetraene structure function as 'stop signals' in inflammation and actively participate in dampening host responses to bring the inflammation to a close, namely, resolution. LXA4 and ATL elicit the multicellular responses via a specific G protein-coupled receptor (GPCR) termed ALX that has been identified in human. (PMID: 16968948, 11478982) [HMDB] |
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CAS Number | Not Available |
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Structure | |
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Synonyms | |
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Predicted Properties | |
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Chemical Formula | C20H30O5 |
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IUPAC name | (5R,6R,7E,9E,11Z,13E)-5,6-dihydroxy-15-oxoicosa-7,9,11,13-tetraenoic acid |
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InChI Identifier | InChI=1S/C20H30O5/c1-2-3-8-12-17(21)13-9-6-4-5-7-10-14-18(22)19(23)15-11-16-20(24)25/h4-7,9-10,13-14,18-19,22-23H,2-3,8,11-12,15-16H2,1H3,(H,24,25)/b6-4-,7-5+,13-9+,14-10+/t18-,19-/m1/s1 |
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InChI Key | KMQGFEBCBYXSPZ-LGJFVLQCSA-N |
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Isomeric SMILES | CCCCCC(=O)\C=C\C=C/C=C/C=C/[C@@H](O)[C@H](O)CCCC(O)=O |
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Average Molecular Weight | 350.4492 |
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Monoisotopic Molecular Weight | 350.20932407 |
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Classification |
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Description | Belongs to the class of organic compounds known as lipoxins. These are eicosanoids with a trihydroxyicosatetraenoic acid skeleton (a c20-fatty acid, with the chain bearing three hydroxyl groups and four double bonds). Lipoxins have four double bonds, which are all conjugated. In some cases a hydroxyl group is substituted by a C=O group. |
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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 | Lipoxins |
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Alternative Parents | |
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Substituents | - Lipoxin
- Long-chain fatty acid
- Hydroxy fatty acid
- Unsaturated fatty acid
- Fatty acid
- Enone
- Alpha,beta-unsaturated ketone
- Acryloyl-group
- 1,2-diol
- Secondary alcohol
- Ketone
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen 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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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Industrial application: Biological role: |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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Predicted GC-MS | 15-Oxo-lipoxin A4, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-03yi-4952000000-e57e880564517d0afac7 | Spectrum | Predicted GC-MS | 15-Oxo-lipoxin A4, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0zi0-9032750000-584abc8ab27c23b55d06 | Spectrum | Predicted GC-MS | 15-Oxo-lipoxin A4, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00lr-0019000000-bdf2953ec33a91eb4f78 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0lel-9275000000-ead403ea27132e5a759c | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0fdo-9340000000-3337b86d97e463601ca1 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0019000000-91ba750881151b1b6f23 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001j-6389000000-0034ef118b546ce844f3 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-9550000000-6f245915121376d5c49d | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00lr-1219000000-e69d0a06db5c241c2ed7 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-01c9-4944000000-10369ffd650d22eeaa95 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-05fu-8900000000-9a924828e95d842760de | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0009000000-1b702cc7cefe4fbaf422 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-029t-5569000000-f691b66a3738df1c26d8 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-066v-9600000000-3297a139dec81ef654f8 | 2021-09-24 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 30776644 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | Not Available |
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Pubchem Compound ID | 53481477 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB12590 |
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CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | Not Available |
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BIGG ID | Not Available |
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KNApSAcK ID | Not Available |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Not Available |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | |
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