1.0 2016-09-30 22:52:30 UTC 2020-05-11 20:52:11 UTC BMDB0002200 BMDB02200 Leukotriene E4 20-Hydroxy-leukotriene e4 20-OH-Leukotriene e4 LTE4 [5S-[5R*,6S*(s*),7E,9E,11Z,14Z]]- 6-[(2-amino-2-carboxyethyl)thio]-5-hydroxy-7,9,11,14-eicosatetraenoate [5S-[5R*,6S*(s*),7E,9E,11Z,14Z]]- 6-[(2-amino-2-carboxyethyl)thio]-5-hydroxy-7,9,11,14-eicosatetraenoic acid C23H37NO5S 439.609 439.239243989 (5S,6R,7E,9E,11Z,14Z)-6-[(2-amino-2-carboxyethyl)sulfanyl]-5-hydroxyicosa-7,9,11,14-tetraenoic acid leukotriene E4 CCCCC\C=C/C\C=C/C=C/C=C/[C@@H](SCC(N)C(O)=O)[C@@H](O)CCCC(O)=O InChI=1S/C23H37NO5S/c1-2-3-4-5-6-7-8-9-10-11-12-13-16-21(30-18-19(24)23(28)29)20(25)15-14-17-22(26)27/h6-7,9-13,16,19-21,25H,2-5,8,14-15,17-18,24H2,1H3,(H,26,27)(H,28,29)/b7-6-,10-9-,12-11+,16-13+/t19?,20-,21+/m0/s1 OTZRAYGBFWZKMX-MPWKMEBCSA-N belongs to the class of organic compounds known as leukotrienes. These are eicosanoids containing a hydroxyl group attached to the aliphatic chain of an arachidonic acid. Leukotrienes have four double bonds, three (and only three) of which are conjugated. Organic compounds Lipids and lipid-like molecules Fatty Acyls Eicosanoids Leukotrienes Alpha amino acids Amino acids Carbonyl compounds Carboxylic acids Cysteine and derivatives Dialkylthioethers Dicarboxylic acids and derivatives Hydrocarbon derivatives Hydroxy fatty acids Hydroxyeicosatetraenoic acids Long-chain fatty acids Monoalkylamines Organic oxides Organopnictogen compounds Secondary alcohols Sulfenyl compounds Thia fatty acids Unsaturated fatty acids Alcohol Aliphatic acyclic compound Alpha-amino acid Alpha-amino acid or derivatives Amine Amino acid Amino acid or derivatives Carbonyl group Carboxylic acid Carboxylic acid derivative Cysteine or derivatives Dialkylthioether Dicarboxylic acid or derivatives Fatty acid Hydrocarbon derivative Hydroxy fatty acid Hydroxyeicosatetraenoic acid Leukotriene Long-chain fatty acid Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Organosulfur compound Primary aliphatic amine Primary amine Secondary alcohol Sulfenyl compound Thia fatty acid Thioether Unsaturated fatty acid Aliphatic acyclic compounds Solid logp 1.57 ALOGPS logs -5.39 ALOGPS logp 2.02 ChemAxon pka_strongest_acidic 2.39 ChemAxon pka_strongest_basic 9.13 ChemAxon iupac (5S,6R,7E,9E,11Z,14Z)-6-[(2-amino-2-carboxyethyl)sulfanyl]-5-hydroxyicosa-7,9,11,14-tetraenoic acid ChemAxon average_mass 439.609 ChemAxon mono_mass 439.239243989 ChemAxon smiles CCCCC\C=C/C\C=C/C=C/C=C/[C@@H](SCC(N)C(O)=O)[C@@H](O)CCCC(O)=O ChemAxon formula C23H37NO5S ChemAxon inchi InChI=1S/C23H37NO5S/c1-2-3-4-5-6-7-8-9-10-11-12-13-16-21(30-18-19(24)23(28)29)20(25)15-14-17-22(26)27/h6-7,9-13,16,19-21,25H,2-5,8,14-15,17-18,24H2,1H3,(H,26,27)(H,28,29)/b7-6-,10-9-,12-11+,16-13+/t19?,20-,21+/m0/s1 ChemAxon inchikey OTZRAYGBFWZKMX-MPWKMEBCSA-N ChemAxon polar_surface_area 120.85 ChemAxon refractivity 127.62 ChemAxon polarizability 50.58 ChemAxon rotatable_bond_count 18 ChemAxon acceptor_count 6 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 13730 Specdb::CMs 38311 Specdb::MsMs 106362 Specdb::MsMs 106363 Specdb::MsMs 106364 Specdb::MsMs 173094 Specdb::MsMs 173095 Specdb::MsMs 173096 Smooth Muscle 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 Leukotriene E4 Rosenberger, Michael; Newkom, Christian; Aig, Edward R. Total synthesis of leukotriene E4, a member of the SRS-A family. Journal of the American Chemical Society (1983), 105(11), 3656-61.