1.0 2011-09-21 00:23:01 UTC 2015-07-21 06:57:28 UTC FDB022996 Levuglandin D2 Levuglandin D2 is one of the products of a non-enzymatically rearrangement of prostaglandin H2 (PGH2) to this highly reactive gamma-keto aldehyde. PGH2 markedly accelerates the formation of dimers and higher oligomers of amyloid beta1-42. This evidence implicates cyclooxygenase activity in the pathogenesis of Alzheimer's disease, and is associated with the formation of levuglandin adducts of the peptide. Levuglandins (LGs) and their stereo and structural isomers are extraordinarily reactive &#947;-ketoaldehydes that are generated by rearrangements of prostanoid endoperoxide intermediates of polyene cyclooxygenation. Their rapid adduction with biological nucleophiles results, inter alia, in pathological modifications of proteins and DNA. It also complicates their detection. Cyclooxygenase-promoted lipid oxidation is a pivotal step in the biosynthesis of an array of physiologically active metabolites. COX fosters a highly regio and stereoselective cyclooxygenation of arachidonic acid (AA) to deliver a single, enantiomerically pure endoperoxide, PGH2, that is a branch point in the biosynthesis of numerous hormone-like mediators of cellular activities. Spontaneous rearrangements of PGH2 were known to generate prostaglandins (PG) PGD2 and PGE2. (PMID: 12358806, 15752459, 3317517, 10224068) [HMDB] 9,10-Seco-9,11-dioxo-15S-hydroxy-5Z,13E-prostadienoate 9,10-Seco-9,11-dioxo-15S-hydroxy-5Z,13E-prostadienoic acid LGD2 C20H32O5 352.4651 352.224974134 (8R,9R,12S)-9-acetyl-8-formyl-12-hydroxyheptadeca-5,10-dienoic acid (8R,9R,12S)-9-acetyl-8-formyl-12-hydroxyheptadeca-5,10-dienoic acid [H]C(=C[C@@]([H])(C(C)=O)[C@@]([H])(CC=CCCCC(O)=O)C=O)[C@@]([H])(O)CCCCC InChI=1S/C20H32O5/c1-3-4-7-11-18(23)13-14-19(16(2)22)17(15-21)10-8-5-6-9-12-20(24)25/h5,8,13-15,17-19,23H,3-4,6-7,9-12H2,1-2H3,(H,24,25)/t17-,18-,19-/m0/s1 MLLWPVVMXGUOHD-FHWLQOOXSA-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. Long-chain fatty acids Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acids and conjugates Aliphatic acyclic compounds 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 Solid logp 3.52 ALOGPS logs -4.16 ALOGPS solubility 2.43e-02 g/l ALOGPS logp 3.36 ChemAxon pka_strongest_acidic 4.51 ChemAxon pka_strongest_basic -1.6 ChemAxon iupac (8R,9R,12S)-9-acetyl-8-formyl-12-hydroxyheptadeca-5,10-dienoic acid ChemAxon average_mass 352.4651 ChemAxon mono_mass 352.224974134 ChemAxon smiles [H]C(=C[C@@]([H])(C(C)=O)[C@@]([H])(CC=CCCCC(O)=O)C=O)[C@@]([H])(O)CCCCC ChemAxon formula C20H32O5 ChemAxon inchi InChI=1S/C20H32O5/c1-3-4-7-11-18(23)13-14-19(16(2)22)17(15-21)10-8-5-6-9-12-20(24)25/h5,8,13-15,17-19,23H,3-4,6-7,9-12H2,1-2H3,(H,24,25)/t17-,18-,19-/m0/s1 ChemAxon inchikey MLLWPVVMXGUOHD-FHWLQOOXSA-N ChemAxon polar_surface_area 91.67 ChemAxon refractivity 100.54 ChemAxon polarizability 40.55 ChemAxon rotatable_bond_count 15 ChemAxon acceptor_count 5 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon HMDB02400 34820 #<Reference:0x000055ce332479d8> #<Reference:0x000055ce33247820> #<Reference:0x000055ce33247668> #<Reference:0x000055ce332474b0> 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