1.0 2016-09-30 23:09:26 UTC 2020-05-11 20:45:42 UTC BMDB0004385 BMDB04385 Lipoxin A4 (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-eicosatetraenoic acid (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-tetraenoic acid 5(S),6(R),15(S)-Trihydroxyeicosa-7E,9E,11Z,13E-tetraenoic acid 5S,6R,15S-Trihydroxy-7,9,13-trans-11-cis-eicosatetraenoic acid 5S,6R,15S-Trihydroxy-7E,9E,11Z,13E-eicosatetraenoic acid 5S,6R-LipoxinA4 6R-LXA4 LXA4 (5S,6R,15S)-Trihydroxy-7,9,13-trans-11-cis-eicosatetraenoate (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-Trihydroxyeicosa-7,9,11,13-tetraenoate (7E,9E,11Z,13E)-(5S,6R,15S)-5,6,15-Trihydroxyicosa-7,9,11,13-tetraenoate 5(S),6(R),15(S)-Trihydroxyeicosa-7E,9E,11Z,13E-tetraenoate 5S,6R,15S-Trihydroxy-7,9,13-trans-11-cis-eicosatetraenoate 5S,6R,15S-Trihydroxy-7E,9E,11Z,13E-eicosatetraenoate 5S,6S-Lipoxin a4 15-Epi-lxa4 15-Epi-lipoxin a4 5,6,15-Tri-hete 5,6,15-TriHETE 5,6,15-Trihydroxy-7,9,11,13-eicosatetraenoic acid C20H32O5 352.4651 352.224974134 (5S,6R,7E,9E,11Z,13E,15S)-5,6,15-trihydroxyicosa-7,9,11,13-tetraenoic acid lipoxin A4 89663-86-5 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-/m0/s1 IXAQOQZEOGMIQS-SSQFXEBMSA-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. Organic compounds Lipids and lipid-like molecules Fatty Acyls Eicosanoids Lipoxins 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 Aliphatic acyclic compounds Lipoxins Lipoxins hydroxy fatty acid lipoxin long-chain fatty acid polyunsaturated fatty acid Solid logp 4.61 ALOGPS logs -3.90 ALOGPS logp 3.05 ChemAxon pka_strongest_acidic 4.48 ChemAxon pka_strongest_basic -1.6 ChemAxon iupac (5S,6R,7E,9E,11Z,13E,15S)-5,6,15-trihydroxyicosa-7,9,11,13-tetraenoic acid ChemAxon average_mass 352.4651 ChemAxon mono_mass 352.224974134 ChemAxon smiles CCCCC[C@H](O)\C=C\C=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-SSQFXEBMSA-N ChemAxon polar_surface_area 97.99 ChemAxon refractivity 104.35 ChemAxon polarizability 41.54 ChemAxon rotatable_bond_count 14 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Specdb::CMs 11395 Specdb::CMs 38760 Specdb::CMs 157907 Specdb::MsMs 291157 Specdb::MsMs 291158 Specdb::MsMs 291159 Specdb::MsMs 330994 Specdb::MsMs 330995 Specdb::MsMs 330996 Specdb::MsMs 440659 Specdb::MsMs 440665 Specdb::MsMs 2728912 Specdb::MsMs 2728913 Specdb::MsMs 2728914 Specdb::MsMs 2979920 Specdb::MsMs 2979921 Specdb::MsMs 2979922 Epidermis Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Leukocyte Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Platelet Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 FDB023370 5280914 4444429 C06314 6498 Lipoxin 7058 Rodriguez, A.; Nomen, M.; Spur, B. W.; Godfroid, J. J.; Lee, T. H. Total synthesis of lipoxin A4 and lipoxin B4 from butadiene. Tetrahedron Letters (2000), 41(6), 823-826.