1.0 2016-09-30 22:54:36 UTC 2020-04-22 15:10:48 UTC BMDB0002363 BMDB02363 Levuglandin E2 10,11-Seco-9,11-dioxo-15S-hydroxy-5Z,13E-prostadienoate 10,11-Seco-9,11-dioxo-15S-hydroxy-5Z,13E-prostadienoic acid LGE2 C20H32O5 352.4651 352.224974134 (5Z,8S,9R,10E,12S)-8-acetyl-9-formyl-12-hydroxyheptadeca-5,10-dienoic acid (5Z,8S,9R,10E,12S)-8-acetyl-9-formyl-12-hydroxyheptadeca-5,10-dienoic acid 91712-41-3 CCCCC[C@H](O)\C=C\[C@@H](C=O)[C@H](C\C=C/CCCC(O)=O)C(C)=O InChI=1S/C20H32O5/c1-3-4-7-10-18(23)14-13-17(15-21)19(16(2)22)11-8-5-6-9-12-20(24)25/h5,8,13-15,17-19,23H,3-4,6-7,9-12H2,1-2H3,(H,24,25)/b8-5-,14-13+/t17-,18-,19+/m0/s1 WJWAORNTZNRHBP-LBONXFAWSA-N belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acids and conjugates Long-chain fatty acids Aldehydes Branched fatty acids Carboxylic acids Hydrocarbon derivatives Hydroxy fatty acids Ketones Monocarboxylic acids and derivatives Organic oxides Secondary alcohols Unsaturated fatty acids Alcohol Aldehyde Aliphatic acyclic compound Branched fatty acid Carbonyl group Carboxylic acid Carboxylic acid derivative Hydrocarbon derivative Hydroxy fatty acid Ketone Long-chain fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Secondary alcohol Unsaturated fatty acid Aliphatic acyclic compounds Levuglandins Solid logp 3.52 ALOGPS logs -4.16 ALOGPS logp 3.36 ChemAxon pka_strongest_acidic 4.35 ChemAxon pka_strongest_basic -1.6 ChemAxon iupac (5Z,8S,9R,10E,12S)-8-acetyl-9-formyl-12-hydroxyheptadeca-5,10-dienoic acid ChemAxon average_mass 352.4651 ChemAxon mono_mass 352.224974134 ChemAxon smiles CCCCC[C@H](O)\C=C\[C@@H](C=O)[C@H](C\C=C/CCCC(O)=O)C(C)=O ChemAxon formula C20H32O5 ChemAxon inchi InChI=1S/C20H32O5/c1-3-4-7-10-18(23)14-13-17(15-21)19(16(2)22)11-8-5-6-9-12-20(24)25/h5,8,13-15,17-19,23H,3-4,6-7,9-12H2,1-2H3,(H,24,25)/b8-5-,14-13+/t17-,18-,19+/m0/s1 ChemAxon inchikey WJWAORNTZNRHBP-LBONXFAWSA-N ChemAxon polar_surface_area 91.67 ChemAxon refractivity 100.54 ChemAxon polarizability 40.28 ChemAxon rotatable_bond_count 15 ChemAxon acceptor_count 5 ChemAxon donor_count 2 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 18490 Specdb::CMs 38392 Specdb::CMs 169167 Specdb::MsMs 306985 Specdb::MsMs 306986 Specdb::MsMs 306987 Specdb::MsMs 350812 Specdb::MsMs 350813 Specdb::MsMs 350814 Specdb::MsMs 2296301 Specdb::MsMs 2296302 Specdb::MsMs 2296303 Specdb::MsMs 2643330 Specdb::MsMs 2643331 Specdb::MsMs 2643332 FDB022979 30776554 5282261 C13807 34821 Levuglandin Miller, Donald B.; Raychaudhuri, Swadesh R.; Avasthi, Kamlakar; Lal, Kasturi; Levison, Bruce; Salomon, Robert G. Prostaglandin endoperoxides. 25 Levuglandin E2: enantiocontrolled total synthesis of a biologically active rearrangement product from the prostaglandin endoperoxide PGH2. J. Org. Chem. 1990(55) 3164-3175