| Record Information |
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| Version | 2.0 |
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| Created at | 2024-09-11 19:27:37 UTC |
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| Updated at | 2024-09-11 19:27:37 UTC |
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| NP-MRD ID | NP0339053 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | 15-Epi-lipoxin A4 |
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| Description | 15-Epi-lipoxin A4, also known as 15-epi-lxa4 or 5,6,15-trihete, 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. These eicosanoids (i.E., 15-Epi-lipoxin A4 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. 15-Epi-lipoxin A4 is an extremely weak basic (essentially neutral) compound (based on its pKa). This phenomenon is an active process that is governed by specific lipid mediators and involves a series of well-orchestrated temporal events. 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. 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. Thus, potent locally released mediators serve as checkpoint controllers of inflammation. 15-Epi-lipoxin A4 and ATL elicit the multicellular responses via a specific G protein-coupled receptor (GPCR) termed ALX that has been identified in human. 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 15-Epi-lipoxin A4 (ATL). 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. |
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| Structure | CCCCC[C@@H](O)\C=C\C=C/C=C/C=C/[C@@H](O)[C@H](O)CCCC(O)=O InChI=1S/C20H32O5/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/h4-7,9-10,13-14,17-19,21-23H,2-3,8,11-12,15-16H2,1H3,(H,24,25)/b6-4-,7-5+,13-9+,14-10+/t17-,18-,19-/m1/s1 |
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| Synonyms | | Value | Source |
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| 15-Epi-lxa(,4) | HMDB | | 5(S),6(R),15(R)-Trihydroxy-7,9,13-trans-11-cis eicosatetraenoate | HMDB | | 5(S),6(R),15(R)-Trihydroxy-7,9,13-trans-11-cis eicosatetraenoic acid | HMDB | | 5(S),6(R),15(R)-Trihydroxy-7,9,13-trans-11-cis eicosatetraenoic acid anion | HMDB | | 5(S),6(R),15(R)-Trihydroxy-7E,9E,11Z,13E-eicosatetraenoate | HMDB | | 5(S),6(R),15(R)-Trihydroxy-7E,9E,11Z,13E-eicosatetraenoic acid | HMDB | | 5(S),6(R),15(R)-Trihydroxy-7E,9E,11Z,13E-eicosatetraenoic acid anion | HMDB | | 15-Epi-lxa4 | HMDB | | 5,6,15-TriHETE | HMDB | | 5,6,15-Trihydroxy-7,9,11,13-eicosatetraenoic acid | HMDB | | 5,6,15-Tri-hete | HMDB | | LXA4 | HMDB | | Lipoxin a4 | HMDB | | (5R,6R,7E,9E,11Z,15R)-5,6,15-Trihydroxyicosa-7,9,11,13-tetraenoate | Generator |
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| Chemical Formula | C20H32O5 |
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| Average Mass | 352.4651 Da |
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| Monoisotopic Mass | 352.22497 Da |
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| IUPAC Name | (5R,6R,7E,9E,11Z,13E,15R)-5,6,15-trihydroxyicosa-7,9,11,13-tetraenoic acid |
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| Traditional Name | (5R,6R,7E,9E,11Z,13E,15R)-5,6,15-trihydroxyicosa-7,9,11,13-tetraenoic acid |
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| CAS Registry Number | Not Available |
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| SMILES | CCCCC[C@@H](O)\C=C\C=C/C=C/C=C/[C@@H](O)[C@H](O)CCCC(O)=O |
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| InChI Identifier | InChI=1S/C20H32O5/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/h4-7,9-10,13-14,17-19,21-23H,2-3,8,11-12,15-16H2,1H3,(H,24,25)/b6-4-,7-5+,13-9+,14-10+/t17-,18-,19-/m1/s1 |
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| InChI Key | IXAQOQZEOGMIQS-BZIKWXEGSA-N |
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| Experimental Spectra |
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| Not Available | | Predicted Spectra |
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| Not Available | | Chemical Shift Submissions |
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| Not Available | | Species |
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| Species of Origin | Not Available |
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| Chemical Taxonomy |
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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
- 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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| Physical Properties |
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| State | Not Available |
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| Experimental 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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| Predicted Properties | |
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