1.0 2011-09-21 00:28:50 UTC 2015-07-21 06:57:39 UTC FDB023370 Lipoxin A4 Lipoxin A4 (LXA4) was first identified in 1984 by Serhan and colleagues as 5-lipoxygenase interaction product of activated leukocytes. Endogenous transcellular biosynthesis of LXA4 occurs via interaction of leukocytes with epithelium, endothelium or platelets. Lipoxins (LXs) or the lipoxygenase interaction products are generated from arachidonic acid via sequential actions of lipoxygenases and subsequent reactions to give specific trihydroxytetraene-containing eicosanoids. These unique structures are formed during cell-cell interactions and appear to act at both temporal and spatially distinct sites from other eicosanoids produced during the course of inflammatory responses and to stimulate natural resolution. Lipoxin A4 (LXA4) and lipoxin B4 (LXB4) are positional isomers that each possesses potent cellular and in vivo actions. These LX structures are conserved across species. The results of numerous studies reviewed in this work now confirm that they are the first recognized eicosanoid chemical mediators that display both potent anti-inflammatory and pro-resolving actions in vivo in disease models that include rabbit, rat, and mouse systems. LXs act at specific GPCRs as agonists to regulate cellular responses of interest in inflammation and resolution. Aspirin has a direct impact in the LX circuit by triggering the biosynthesis of endogenous epimers of LX, termed the aspirin-triggered 15-epi-LX, that share the potent anti-inflammatory actions of LX. (PMID: 16005201, 16613568) [HMDB] (5S,6R,15S)-Trihydroxy-7,9,13-trans-11-cis-eicosatetraenoate (5S,6R,15S)-Trihydroxy-7,9,13-trans-11-cis-eicosatetraenoic acid (5S,6R,7e,9e,11Z,13e,15S)-5,6,15-Trihydroxy-7,9,11,13-eicosatetraenoate (5S,6R,7e,9e,11Z,13e,15S)-5,6,15-Trihydroxy-7,9,11,13-eicosatetraenoic acid (5S,6R,7e,9e,11Z,13e,15S)-5,6,15-Trihydroxyeicosa-7,9,11,13-tetraenoate (5S,6R,7e,9e,11Z,13e,15S)-5,6,15-Trihydroxyeicosa-7,9,11,13-tetraenoic acid (7E,9E,11Z,13E)-(5S,6R,15S)-5,6,15-Trihydroxyicosa-7,9,11,13-tetraenoate (7E,9E,11Z,13E)-(5S,6R,15S)-5,6,15-Trihydroxyicosa-7,9,11,13-tetraenoic acid 5(S),6(R),15(S)-Trihydroxyeicosa-7e,9e,11Z,13e-tetraenoate 5(S),6(R),15(S)-Trihydroxyeicosa-7e,9e,11Z,13e-tetraenoic acid 5S,6R-LipoxinA4 5S,6R,15S-Trihydroxy-7,9,13-trans-11-cis-eicosatetraenoate 5S,6R,15S-Trihydroxy-7,9,13-trans-11-cis-eicosatetraenoic acid 5S,6R,15S-Trihydroxy-7E,9E,11Z,13E-eicosatetraenoate 5S,6R,15S-Trihydroxy-7E,9E,11Z,13E-eicosatetraenoic acid 5S,6S-Lipoxin A4 6R-LXA4 LXA4 C20H32O5 352.4651 352.224974134 (5S,6R,7E,9E,15S)-5,6,15-trihydroxyicosa-7,9,11,13-tetraenoic acid (5S,6R,7E,9E,15S)-5,6,15-trihydroxyicosa-7,9,11,13-tetraenoic acid 89663-86-5 [H][C@](O)(CCCCC)C=CC=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-/m0/s1 IXAQOQZEOGMIQS-WZCAPKNJSA-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 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 Lipoxin Long-chain fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Polyol Secondary alcohol Unsaturated fatty acid Solid logp 4.61 ALOGPS logs -3.90 ALOGPS solubility 4.41e-02 g/l ALOGPS logp 3.05 ChemAxon pka_strongest_acidic 4.48 ChemAxon pka_strongest_basic -1.6 ChemAxon iupac (5S,6R,7E,9E,15S)-5,6,15-trihydroxyicosa-7,9,11,13-tetraenoic acid ChemAxon average_mass 352.4651 ChemAxon mono_mass 352.224974134 ChemAxon smiles [H][C@](O)(CCCCC)C=CC=C\C=C\C=C\[C@@]([H])(O)[C@@]([H])(O)CCCC(O)=O ChemAxon formula C20H32O5 ChemAxon inchi 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-/m0/s1 ChemAxon inchikey IXAQOQZEOGMIQS-WZCAPKNJSA-N ChemAxon polar_surface_area 97.99 ChemAxon refractivity 104.35 ChemAxon polarizability 42.15 ChemAxon rotatable_bond_count 14 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon HMDB04385 6498 #<Reference:0x000055ce331793f8> #<Reference:0x000055ce33179240> #<Reference:0x000055ce33179088> #<Reference:0x000055ce33178ed0> #<Reference:0x000055ce33178d18> #<Reference:0x000055ce33178b60> #<Reference:0x000055ce331789a8> #<Reference:0x000055ce331787c8> #<Reference:0x000055ce331785c0> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823