1.0 2011-09-21 01:50:38 UTC 2015-07-21 06:59:38 UTC FDB029136 15-Epi-lipoxin B5 15-epi-lipoxin B5 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] 5(S),14(R),15(S)-trihydroxy-6E,8Z,10E,12E,17Z-eicosapentaenoate 5(S),14(R),15(S)-trihydroxy-6E,8Z,10E,12E,17Z-eicosapentaenoic acid 5(S),14(R),15(S)-trihydroxy-6E,8Z,10E,12E,17Z-eicosapentaenoic acid anion C20H30O5 350.4492 350.20932407 (5R,6E,8Z,10E,12E,14R,15R,17Z)-5,14,15-trihydroxyicosa-6,8,10,12,17-pentaenoic acid (5R,6E,8Z,10E,12E,14R,15R,17Z)-5,14,15-trihydroxyicosa-6,8,10,12,17-pentaenoic acid CC\C=C/C[C@@H](O)[C@H](O)\C=C\C=C\C=C/C=C/[C@H](O)CCCC(O)=O InChI=1S/C20H30O5/c1-2-3-8-14-18(22)19(23)15-10-7-5-4-6-9-12-17(21)13-11-16-20(24)25/h3-10,12,15,17-19,21-23H,2,11,13-14,16H2,1H3,(H,24,25)/b6-4-,7-5+,8-3-,12-9+,15-10+/t17-,18+,19+/m0/s1 VLLDKSJDBRLUOY-XIFXWWOOSA-N 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. Hydroxyeicosapentaenoic acids Organic compounds Lipids and lipid-like molecules Fatty Acyls Eicosanoids Aliphatic acyclic compounds Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Hydroxy fatty acids Long-chain fatty acids Monocarboxylic acids and derivatives Organic oxides Polyols Secondary alcohols Unsaturated fatty acids Alcohol Aliphatic acyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Fatty acid Hydrocarbon derivative Hydroxy fatty acid Hydroxyeicosapentaenoic acid Long-chain fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Polyol Secondary alcohol Unsaturated fatty acid Solid logp 4.32 ALOGPS logs -3.85 ALOGPS solubility 4.93e-02 g/l ALOGPS logp 2.69 ChemAxon pka_strongest_acidic 4.65 ChemAxon pka_strongest_basic -1.5 ChemAxon iupac (5R,6E,8Z,10E,12E,14R,15R,17Z)-5,14,15-trihydroxyicosa-6,8,10,12,17-pentaenoic acid ChemAxon average_mass 350.4492 ChemAxon mono_mass 350.20932407 ChemAxon smiles CC\C=C/C[C@@H](O)[C@H](O)\C=C\C=C\C=C/C=C/[C@H](O)CCCC(O)=O ChemAxon formula C20H30O5 ChemAxon inchi InChI=1S/C20H30O5/c1-2-3-8-14-18(22)19(23)15-10-7-5-4-6-9-12-17(21)13-11-16-20(24)25/h3-10,12,15,17-19,21-23H,2,11,13-14,16H2,1H3,(H,24,25)/b6-4-,7-5+,8-3-,12-9+,15-10+/t17-,18+,19+/m0/s1 ChemAxon inchikey VLLDKSJDBRLUOY-XIFXWWOOSA-N ChemAxon polar_surface_area 97.99 ChemAxon refractivity 105.46 ChemAxon polarizability 39.96 ChemAxon rotatable_bond_count 13 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 9885 Specdb::CMs 39968 Specdb::CMs 160748 Specdb::MsMs 287857 Specdb::MsMs 287858 Specdb::MsMs 287859 Specdb::MsMs 326806 Specdb::MsMs 326807 Specdb::MsMs 326808 Specdb::MsMs 2440963 Specdb::MsMs 2440964 Specdb::MsMs 2440965 Specdb::MsMs 2524371 Specdb::MsMs 2524372 Specdb::MsMs 2524373 HMDB12588 #<Reference:0x000055ce30ffd350> #<Reference:0x000055ce30ffd080>