1.0 2011-09-21 01:50:39 UTC 2015-07-21 06:59:38 UTC FDB029137 15-Oxo-lipoxin A4 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] (5S,6R)-dihydroxy-15-oxo-(7E,9E,11Z,13E)-Eicosatetraenoate (5S,6R)-dihydroxy-15-oxo-(7E,9E,11Z,13E)-Eicosatetraenoic acid 15-oxo-LXA(,4) C20H30O5 350.4492 350.20932407 (5R,6R,7E,9E,11Z,13E)-5,6-dihydroxy-15-oxoicosa-7,9,11,13-tetraenoic acid (5R,6R,7E,9E,11Z,13E)-5,6-dihydroxy-15-oxoicosa-7,9,11,13-tetraenoic acid CCCCCC(=O)\C=C\C=C/C=C/C=C/[C@@H](O)[C@H](O)CCCC(O)=O 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 KMQGFEBCBYXSPZ-LGJFVLQCSA-N 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. Lipoxins Organic compounds Lipids and lipid-like molecules Fatty Acyls Eicosanoids Aliphatic acyclic compounds 1,2-diols Acryloyl compounds Carboxylic acids Enones Hydrocarbon derivatives Hydroxy fatty acids Ketones Long-chain fatty acids Monocarboxylic acids and derivatives Organic oxides Secondary alcohols Unsaturated fatty acids 1,2-diol Acryloyl-group Alcohol Aliphatic acyclic compound Alpha,beta-unsaturated ketone Carbonyl group Carboxylic acid Carboxylic acid derivative Enone Fatty acid Hydrocarbon derivative Hydroxy fatty acid Ketone Lipoxin Long-chain fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Secondary alcohol Unsaturated fatty acid Solid logp 3.58 ALOGPS logs -4.07 ALOGPS solubility 2.98e-02 g/l ALOGPS logp 3.46 ChemAxon pka_strongest_acidic 4.48 ChemAxon pka_strongest_basic -3.2 ChemAxon iupac (5R,6R,7E,9E,11Z,13E)-5,6-dihydroxy-15-oxoicosa-7,9,11,13-tetraenoic acid ChemAxon average_mass 350.4492 ChemAxon mono_mass 350.20932407 ChemAxon smiles CCCCCC(=O)\C=C\C=C/C=C/C=C/[C@@H](O)[C@H](O)CCCC(O)=O ChemAxon formula C20H30O5 ChemAxon inchi 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 ChemAxon inchikey KMQGFEBCBYXSPZ-LGJFVLQCSA-N ChemAxon polar_surface_area 94.83 ChemAxon refractivity 103.45 ChemAxon polarizability 39.93 ChemAxon rotatable_bond_count 14 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 24667 Specdb::CMs 39969 Specdb::CMs 159993 Specdb::MsMs 320623 Specdb::MsMs 320624 Specdb::MsMs 320625 Specdb::MsMs 368038 Specdb::MsMs 368039 Specdb::MsMs 368040 Specdb::MsMs 2785585 Specdb::MsMs 2785586 Specdb::MsMs 2785587 Specdb::MsMs 2924164 Specdb::MsMs 2924165 Specdb::MsMs 2924166 HMDB12590 #<Reference:0x000055ce321a6228> #<Reference:0x000055ce321a6020>