1.0 2011-09-21 00:16:32 UTC 2015-07-21 06:57:16 UTC FDB022592 Prostaglandin H2 Prostaglandin H2 (PGH2) is the first intermediate in the biosynthesis of all prostaglandins. Prostaglandins are synthesized from arachidonic acid by the enzyme COX-1 and COX-2, which are also called PGH synthase 1 and 2. These enzymes generate a reactive intermediate PGH2 which has a reasonably long half-life (90-100 s) but is highly lipophilic. PGH2 is converted into the biologically active prostaglandins by prostaglandin isomerases, yielding PGE2, PGD2, and PGF2, or by thromboxane synthase to make TxA2 or by prostacyclin synthase to make PGI2. Most nonsteroidal anti-inflammatory drugs such as aspirin and indomethacin inhibit both PGH synthase 1 and 2. A key feature for eicosanoid transcellular biosynthesis is the export of PGH2 or LTA4 from the donor cell as well as the uptake of these reactive intermediates by the acceptor cell. Very little is known about either process despite the demonstrated importance of both events. In cells, PGH2 rearranges nonenzymatically to LGs even in the presence of enzymes that use PGH2 as a substrate. When platelets form Thromboxane A2 (TXA2) from endogenous arachidonic acid (AA), PGH2 reaches concentrations very similar to those of TXA2 and high enough to produce strong platelet activation. Therefore, platelet activation by TXA2 appears to go along with an activation by PGH2. The agonism of PGH2 is limited by the formation of inhibitory prostaglandins, especially PGD2 at higher concentrations. That is why thromboxane synthase inhibitors in PRP and at a physiological HSA concentration do not augment platelet activation. (PMID: 2798452, 15650407, 16968946) Prostaglandins are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs) and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes) and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signaling pathways. [HMDB] (15S)Hydroxy-9alpha,11alpha-(epoxymethano)prosta-5,13-dienoate (15S)Hydroxy-9alpha,11alpha-(epoxymethano)prosta-5,13-dienoic acid (5Z,13E,15S)-9-alpha,11-alpha-epidioxy-15-hydroxyprosta-5,13-dienoate (5Z,13E,15S)-9-alpha,11-alpha-epidioxy-15-hydroxyprosta-5,13-dienoic acid (5Z,13E,15S)-9a,11a-epidioxy-15-hydroxyprosta-5,13-dienoate (5Z,13E,15S)-9a,11a-epidioxy-15-hydroxyprosta-5,13-dienoic acid (5Z,13e,15S)-9alpha,11alpha-Epidioxy-15-hydroxyprosta-5,13-dienoate (5Z,13e,15S)-9alpha,11alpha-Epidioxy-15-hydroxyprosta-5,13-dienoic acid (5Z,13e,15S)-9α,11α-epidioxy-15-hydroxyprosta-5,13-dienoate (5Z,13e,15S)-9α,11α-epidioxy-15-hydroxyprosta-5,13-dienoic acid (5Z,13E)-(15S)-9-alpha,11-alpha-epidioxy-15-hydroxyprosta-5,13-dienoate (5Z,13E)-(15S)-9-alpha,11-alpha-epidioxy-15-hydroxyprosta-5,13-dienoic acid (5Z,13E)-(15S)-9,11-epidioxy-15-hydroxyprosta-5,13-dienoate (5Z,13E)-(15S)-9,11-epidioxy-15-hydroxyprosta-5,13-dienoic acid (5Z,13e)-(15S)-9a,11a-Epidioxy-15-hydroxyprosta-5,13-dienoate (5Z,13e)-(15S)-9a,11a-Epidioxy-15-hydroxyprosta-5,13-dienoic acid (5Z,13E)-(15S)-9alpha,11alpha-Epidioxy-15-hydroxyprosta-5,13-dienoate (5Z,13E)-(15S)-9alpha,11alpha-Epidioxy-15-hydroxyprosta-5,13-dienoic acid (5Z,13e)-(15S)-9α,11α-epidioxy-15-hydroxyprosta-5,13-dienoate (5Z,13e)-(15S)-9α,11α-epidioxy-15-hydroxyprosta-5,13-dienoic acid (5Z,9a,11a,13E,15S)-9,11-epidioxy-15-hydroxyprosta-5,13-dien-1-oate (5Z,9a,11a,13E,15S)-9,11-epidioxy-15-hydroxyprosta-5,13-dien-1-oic acid (5Z,9alpha,11alpha,13E,15S)-9,11-epidioxy-15-hydroxy-Prosta-5,13-dien-1-oate (5Z,9alpha,11alpha,13E,15S)-9,11-epidioxy-15-hydroxy-Prosta-5,13-dien-1-oic acid (5Z,9alpha,11alpha,13e,15S)-9,11-Epidioxy-15-hydroxyprosta-5,13-dien-1-Oate (5Z,9alpha,11alpha,13e,15S)-9,11-Epidioxy-15-hydroxyprosta-5,13-dien-1-Oic acid (5Z,9α,11α,13e,15S)-9,11-epidioxy-15-hydroxyprosta-5,13-dien-1-Oate (5Z,9α,11α,13e,15S)-9,11-epidioxy-15-hydroxyprosta-5,13-dien-1-Oic acid (5Z)-7-{(1R,4S,5R,6R)-6-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]hept-5-yl}hept-5-enoate (5Z)-7-{(1R,4S,5R,6R)-6-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]hept-5-yl}hept-5-enoic acid 15-Hydroxy-9alpha,11alpha-peroxidoprosta-5,13-dienoate 15-Hydroxy-9alpha,11alpha-peroxidoprosta-5,13-dienoic acid 9,11-Epoxymethano-pgh2 9S,11R-epidioxy-15S-hydroxy-5Z,13E-prostadienoate 9S,11R-epidioxy-15S-hydroxy-5Z,13E-prostadienoic acid Endoperoxide H2 PGH2 Prostaglandin R2 Prostaglandin-H2 C20H32O5 352.4651 352.224974134 7-[(1R,4S,5R,6R)-6-[(3S)-3-hydroxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hept-5-enoic acid 7-[(1R,4S,5R,6R)-6-[(3S)-3-hydroxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hept-5-enoic acid 42935-17-1 [H]C(=C[C@@]1([H])[C@@]2([H])C[C@]([H])(OO2)[C@]1([H])CC=CCCCC(O)=O)[C@@]([H])(O)CCCCC InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18-14-19(17)25-24-18)10-7-4-5-8-11-20(22)23/h4,7,12-13,15-19,21H,2-3,5-6,8-11,14H2,1H3,(H,22,23)/t15-,16+,17+,18-,19+/m0/s1 YIBNHAJFJUQSRA-BRIYLRKRSA-N belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid. Prostaglandins and related compounds Organic compounds Lipids and lipid-like molecules Fatty Acyls Eicosanoids Aliphatic heteropolycyclic compounds 1,2-dioxanes 1,2-dioxolanes Carbonyl compounds Carboxylic acids Dialkyl peroxides Heterocyclic fatty acids Hydrocarbon derivatives Hydroxy fatty acids Long-chain fatty acids Monocarboxylic acids and derivatives Oxacyclic compounds Secondary alcohols Unsaturated fatty acids Alcohol Aliphatic heteropolycyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Dialkyl peroxide Fatty acid Heterocyclic fatty acid Hydrocarbon derivative Hydroxy fatty acid Long-chain fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Ortho-dioxane Ortho-dioxolane Oxacycle Prostaglandin skeleton Secondary alcohol Unsaturated fatty acid Solid logp 4.27 ALOGPS logs -4.02 ALOGPS solubility 3.37e-02 g/l ALOGPS logp 3.96 ChemAxon pka_strongest_acidic 4.36 ChemAxon pka_strongest_basic -1.6 ChemAxon iupac 7-[(1R,4S,5R,6R)-6-[(3S)-3-hydroxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hept-5-enoic acid ChemAxon average_mass 352.4651 ChemAxon mono_mass 352.224974134 ChemAxon smiles [H]C(=C[C@@]1([H])[C@@]2([H])C[C@]([H])(OO2)[C@]1([H])CC=CCCCC(O)=O)[C@@]([H])(O)CCCCC ChemAxon formula C20H32O5 ChemAxon inchi InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18-14-19(17)25-24-18)10-7-4-5-8-11-20(22)23/h4,7,12-13,15-19,21H,2-3,5-6,8-11,14H2,1H3,(H,22,23)/t15-,16+,17+,18-,19+/m0/s1 ChemAxon inchikey YIBNHAJFJUQSRA-BRIYLRKRSA-N ChemAxon polar_surface_area 75.99 ChemAxon refractivity 98.04 ChemAxon polarizability 40.4 ChemAxon rotatable_bond_count 12 ChemAxon acceptor_count 5 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Arachidonic Acid Metabolism SMP00075 map00590 HMDB01381 #<Reference:0x000055ce31e6d9d0> #<Reference:0x000055ce31e6d7f0> #<Reference:0x000055ce31e6d458> #<Reference:0x000055ce31e6d2a0> #<Reference:0x000055ce31e6d0e8> #<Reference:0x000055ce31e6cf30> #<Reference:0x000055ce31e6cd78> #<Reference:0x000055ce31e6cbc0> #<Reference:0x000055ce31e6ca08> #<Reference:0x000055ce31e6c850> #<Reference:0x000055ce31e6c698> #<Reference:0x000055ce31e6c4e0> #<Reference:0x000055ce31e6c1c0> #<Reference:0x000055ce31e6ebc8> #<Reference:0x000055ce31e6f960> #<Reference:0x000055ce31e6be00> #<Reference:0x000055ce31e6bc20> #<Reference:0x000055ce31e6ba68> #<Reference:0x000055ce31e6b8b0> #<Reference:0x000055ce31e6b6f8> #<Reference:0x000055ce31e6b540> Hematopoietic prostaglandin D synthase O60760 HPGDS Prostaglandin E synthase O14684 PTGES Prostaglandin E synthase 2 Q9H7Z7 PTGES2 Prostaglandin E synthase 3 Q15185 PTGES3 Prostaglandin-H2 D-isomerase P41222 PTGDS