459PathwayTenoxicam Action PathwayTenoxicam (also named mobiflex and tilcotil) is a nonsteroidal anti-inflammatory drug (NSAID). It can be used to reduce inflammation, swelling, stiffness, and pain that are associated with various diseases such as tendinitis, bursitis and etc. Tenoxicam can block prostaglandin synthesis by the action of inhibition of prostaglandin G/H synthase 1 and 2. Prostaglandin G/H synthase 1 and 2 catalyze the arachidonic acid to prostaglandin G2, and also catalyze prostaglandin G2 to prostaglandin H2 in the metabolism pathway. Decreased prostaglandin synthesis in many animal model's cell is caused by presence of tenoxicam.Drug ActionPW000683TopPathwayVisualizationContext9377001000#000099PathwayVisualization439459Tenoxicam PathwayTenoxicam (also named mobiflex and tilcotil) is a nonsteroidal anti-inflammatory drug (NSAID). It can be used to reduce inflammation, swelling, stiffness, and pain that are associated with various diseases such as tendinitis, bursitis and etc. Tenoxicam can block prostaglandin synthesis by the action of inhibition of prostaglandin G/H synthase 1 and 2. Prostaglandin G/H synthase 1 and 2 catalyze the arachidonic acid to prostaglandin G2, and also catalyze prostaglandin G2 to prostaglandin H2 in the metabolism pathway. Decreased prostaglandin synthesis in many animal model's cell is caused by presence of tenoxicam.Drug1954Tenoxicam inhibition of Prostaglandin G/H synthase 2InhibitorySubPathway15668974Compound21567184ProteinComplex18955Tenoxicam inhibition of Prostaglandin G/H synthase 1InhibitorySubPathway15688974Compound2156963ProteinComplex1827969310195553Celebioglu B, Eslambouli NR, Olcay E, Atakan S: The effect of tenoxicam on intraperitoneal adhesions and prostaglandin E2 levels in mice. Anesth Analg. 1999 Apr;88(4):939-42.459Pathway1CellCL:00000002Platelet CL:00002335HepatocyteCL:00001823NeuronCL:00005401Homo sapiens9606EukaryoteHuman2Bacteria2ProkaryoteBacteria5Bos taurus9913EukaryoteCattle12Mus musculus10090EukaryoteMouse19Schizosaccharomyces pombe4896Eukaryote4Arabidopsis thaliana3702EukaryoteThale cress18Saccharomyces cerevisiae4932EukaryoteYeast10Drosophila melanogaster7227EukaryoteFruit fly17Rattus norvegicus10116EukaryoteRat6Caenorhabditis elegans6239EukaryoteRoundworm1CytosolGO:00058297Endoplasmic Reticulum MembraneGO:00057895CytoplasmGO:00057374PeroxisomeGO:00057772MitochondrionGO:000573920Endoplasmic Reticulum LumenGO:000578813Endoplasmic ReticulumGO:00057836LysosomeGO:00057648Smooth Endoplasmic Reticulum GO:000579010Cell MembraneGO:00058863Mitochondrial MatrixGO:000575916Lysosomal LumenGO:004320212Mitochondrial Inner MembraneGO:000574315NucleusGO:00056342Endothelium BTO:00003931LiverBTO:00007597296KidneyBTO:00006717182111PW_BS00000216212PW_BS000016101711PW_BS0000108511PW_BS0000085411PW_BS0000053211PW_BS00000349711PW_BS0000493612011PW_BS000036181311PW_BS00001829111PW_BS0000299611PW_BS000009111811PW_BS000011261115PW_BS00002614101PW_BS0000144311PW_BS000004311511PW_BS0000312811611PW_BS000028951721PW_BS0000951231751PW_BS0001231251351PW_BS00012512915121PW_BS00012914117191PW_BS00014178811PW_BS00007811PW_BS000001151141PW_BS0001511601181PW_BS0001601613181PW_BS0001612137181PW_BS0000241985181PW_BS0000242111018PW_BS0000241644PW_BS00016429817101PW_BS00002430013101PW_BS000024171211PW_BS00001729341PW_BS0000242491341PW_BS0000241115121PW_BS00011113013121PW_BS0001303317121PW_BS00002833217121PW_BS0000281151012PW_BS0001153361121PW_BS0000283344121PW_BS0000281333121PW_BS0001331321121PW_BS0001321122121PW_BS00011213412121PW_BS000134405105PW_BS000115408451PW_BS000115407251PW_BS000115383751PW_BS000100429151PW_BS000115124151PW_BS000124122551PW_BS000122406351PW_BS0001153841251PW_BS0001003761017PW_BS00005344717171PW_BS00011513613171PW_BS0001363744171PW_BS0000531192171PW_BS0001193987171PW_BS0001134641171PW_BS0001151181171PW_BS0001181355171PW_BS0001351203171PW_BS00012012112171PW_BS0001214824101PW_BS0001154812101PW_BS0001152991101PW_BS0000242975101PW_BS0000244957101PW_BS0001154793101PW_BS00011548012101PW_BS000115502461PW_BS000115206261PW_BS000024388161PW_BS000112205561PW_BS0000243951361PW_BS000113390761PW_BS000112501361PW_BS0001153911261PW_BS000112818512PW_BS000548231511PW_BS000023711PW_BS00000748113PW_BS0000486361PW_BS0000639312011PW_BS00055984711PW_BS0005498974TenoxicamHMDB0014612Tenoxicam is only found in individuals that have used or taken this drug. It is an antiinflammatory agent with analgesic and antipyretic properties, and is used to treat osteoarthritis and control acute pain.The antiinflammatory effects of tenoxicam may result from the inhibition of the enzyme cycooxygenase and the subsequent peripheral inhibition of prostaglandin synthesis. As prostaglandins sensitize pain receptors, their inhibition accounts for the peripheral analgesic effects of tenoxicam. Antipyresis may occur by central action on the hypothalamus, resulting in peripheral dilation, increased cutaneous blood flow, and subsequent heat loss.59804-37-45530474471584DB00469CN1\C(=C(/O)NC2=CC=CC=N2)C(=O)C2=C(C=CS2)S1(=O)=OC13H11N3O4S2InChI=1S/C13H11N3O4S2/c1-16-10(13(18)15-9-4-2-3-6-14-9)11(17)12-8(5-7-21-12)22(16,19)20/h2-7,18H,1H3,(H,14,15)/b13-10-WZWYJBNHTWCXIM-RAXLEYEMSA-N(3Z)-3-{hydroxy[(pyridin-2-yl)amino]methylidene}-2-methyl-2H,3H,4H-1λ⁶-thieno[2,3-e][1,2]thiazine-1,1,4-trione337.374337.019097235-3.092tenoxicam00Tenoxicamum [inn-latin]PW_C008974Tenoicm513921799HemeHMDB0003178Heme is the color-furnishing portion of hemoglobin. It is found free in tissues and as the prosthetic group in many hemeproteins. A heme or haem is a prosthetic group that consists of an iron atom contained in the center of a large heterocyclic organic ring called a porphyrin. Not all porphyrins contain iron, but a substantial fraction of porphyrin-containing metalloproteins have heme as their prosthetic subunit; these are known as hemoproteins.14875-96-8C0003217627HEME_A24604415DB02577CC1=C(CCC(O)=O)C2=CC3=[N+]4C(=CC5=C(C)C(C=C)=C6C=C7C(C)=C(C=C)C8=[N+]7[Fe--]4(N2C1=C8)N56)C(C)=C3CCC(O)=OC34H32FeN4O4InChI=1S/C34H34N4O4.Fe/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25;/h7-8,13-16H,1-2,9-12H2,3-6H3,(H4,35,36,37,38,39,40,41,42);/q;+2/p-2/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-;KABFMIBPWCXCRK-RGGAHWMASA-L4,20-bis(2-carboxyethyl)-10,15-diethenyl-5,9,14,19-tetramethyl-2lambda5,22,23lambda5,25-tetraaza-1-ferraoctacyclo[11.9.1.1^{1,8}.1^{3,21}.0^{2,6}.0^{16,23}.0^{18,22}.0^{11,25}]pentacosa-2,4,6,8,10,12,14,16(23),17,19,21(24)-undecaene-2,23-bis(ylium)-1,1-diuide616.487616.177297665-5.4824,20-bis(2-carboxyethyl)-10,15-diethenyl-5,9,14,19-tetramethyl-2lambda5,22,23lambda5,25-tetraaza-1-ferraoctacyclo[11.9.1.1^{1,8}.1^{3,21}.0^{2,6}.0^{16,23}.0^{18,22}.0^{11,25}]pentacosa-2,4,6,8,10,12,14,16(23),17,19,21(24)-undecaene-2,23-bis(ylium)-1,1-diuide0-2FDB016272(protoporphyrinato)iron;Ferroheme;Ferroheme b;Ferroprotoheme;Ferroprotoporphyrin;Ferroprotoporphyrin ix;Ferrous protoheme;Ferrous protoheme ix;Haem;Hem;Heme;Iron protoporphyrin;Iron protoporphyrin ix;Iron(ii) protoporphyrin ix;Protoferroheme;Protohaem;Protoheme;Protoheme ix;Reduced hematinPW_C001799Heme247163081032486082766512443135449141336196318280629293893238113367263421143734440433148232851709554721235485125551712958301416246786283165971517044160706016173262131183519811898211120651641300929813021300422781776915293769312497735111177364130773673317739833277517115776293367781333478380133786021327896311279932134120431405120603408120955407121085383121658429121746124121910122122570406122691384123065376123133447123144136123228374123521119123650398124216464124297118124463135125142120125277121125742482125896481126196299126499297126512495126718479126827480127224502127357206127632388128070205128083395128086390128309501128434391913Prostaglandin G/H synthase 2P35354Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
HMDBP00975PTGS21q25.2-q25.3M9010011.14.99.160921856491965183883962487865981511400158181405662314083071409394814258863143341931914Prostaglandin G/H synthase 1P23219May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
HMDBP00976PTGS19q32-q33.3M3181311.14.99.12481661621392491964183882962477811585881395141140014818140829714112584714258963143342931184Prostaglandin G/H synthase 21PW_P000184202913821799263Prostaglandin G/H synthase 11PW_P00006374914237179911184089742157false18525510regular200190118411799189false52526010regular10025118421799189false52548010regular100256303913186false4951958subunitregular160806304914186false4954108subunitregular160805135184439186200630324211184118475Cofactor513663439186201630424221184218478Cofactor18474M385 350 C415 350 465 235 495 235 148false18falsetrueM 187 145 L 187 130 L 187 11518475M550 150 L550 200 L600 150 z10true1818476M495 235 C465 235 367 130 337 130 5true1818477M385 350 C415 350 465 450 495 450 148false18falsetrueM 372 400 L 372 385 L 372 37018478M735 405 L735 455 L785 405 z10true1818479M495 450 C465 450 552 385 522 385 5true18105995443914true1879516regular9911184018474Left629513518476Right106095543914true37235016regular9921184018477Left630513618479Right985664201851.01.0023280360774M83 174 C83 124 133 74 183 74 C347 74 560 74 724 74 C774 74 824 124 824 174 C824 282 824 423 824 531 C824 581 774 631 724 631 C560 631 347 631 183 631 C133 631 83 581 83 531 C83 423 83 282 83 174 1true6741.0557.0CenterPathwayVisualizationContext93847004650#000099PathwayVisualization5474Arachidonic Acid MetabolismThis pathway describes the production and subsequent metabolism of arachidonic acid, an omega-6 fatty acid. In resting cells arachidonic acid is present in the phospholipids (especially phosphatidylethanolamine and phosphatidylcholine) of membranes of the body’s cells, and is particularly abundant in the brain. Typically a receptor-dependent event, requiring a transducing G protein, initiates phospholipid hydrolysis and releases the fatty acid into the intracellular medium. Three enzymes mediate this deacylation reaction including phospholipase A2 (PLA2), phospholipase C (PLC), and phospholipase D (PLD). Once released, free arachidonate has three possible fates: 1) reincorporation into phospholipids, 2) diffusion outside the cell, and 3) metabolism. Arachidonate metabolism is carried out by three distinct enzyme classes: cyclooxygenases, lipoxygenases, and cytochrome P450’s. Specifically, the enzymes cyclooxygenase and peroxidase lead to the synthesis of prostaglandin H2, which in turn is used to produce the prostaglandins, prostacyclin, and thromboxanes. The enzyme 5-lipoxygenase leads to 5-HPETE, which in turn is used to produce the leukotrienes, hydroxyeicosatetraenoic acids (HETEs) and lipoxins. Some arachidonic acid is converted into midchain HETEs, omega-chain HETEs, dihydroxyeicosatrienoic acids (DHETs), and epoxyeicosatrienoic acids (EETs) by cytochrome P450 epoxygenase hydroxylase activity. Several products of these pathways act within neurons to modulate the activities of ion channels, protein kinases, ion pumps, and neurotransmitter uptake systems, affecting processes such as cellular proliferation, inflammation, and hemostasis. The newly formed eicosanoids may also exit the cell of origin and bind to G-protein-coupled receptors present on nearby neurons or glial cells.Metabolic1162Lehninger, A.L. Lehninger principles of biochemistry (4th ed.) (2005). New York: W.H Freeman.74Pathway163Vance, D.E., and Vance, J.E. Biochemistry of lipids, lipoproteins, and membranes (4th ed.) (2002) Amsterdam; Boston: Elsevier.74Pathway164Salway, J.G. Metabolism at a glance (3rd ed.) (2004). Alden, Mass.: Blackwell Pub.74Pathway16512045397Kroetz DL, Zeldin DC: Cytochrome P450 pathways of arachidonic acid metabolism. Curr Opin Lipidol. 2002 Jun;13(3):273-83.74Pathway16611451964Zeldin DC: Epoxygenase pathways of arachidonic acid metabolism. J Biol Chem. 2001 Sep 28;276(39):36059-62. doi: 10.1074/jbc.R100030200. Epub 2001 Jul 12.74Pathway1679588707Ondrey FG: Arachidonic acid metabolism: a primer for head and neck surgeons. Head Neck. 1998 Jul;20(4):334-49.74Pathway1681899973Sigal E: The molecular biology of mammalian arachidonic acid metabolism. Am J Physiol. 1991 Feb;260(2 Pt 1):L13-28. doi: 10.1152/ajplung.1991.260.2.L13.74Pathway1CellCL:00000004CardiomyocyteCL:00007462Platelet CL:00002335HepatocyteCL:00001823NeuronCL:00005407Epithelial CellCL:00000666MyocyteCL:000018712AstrocyteCL:00001278Beta cellCL:00006399Pancreatic Beta CellCL:000016911Colorectal Cancer CellCL:00010641Homo sapiens9606EukaryoteHuman12Mus musculus10090EukaryoteMouse5Bos taurus9913EukaryoteCattle17Rattus norvegicus10116EukaryoteRat3Escherichia coli562Prokaryote24Solanum lycopersicum4081EukaryoteTomato18Saccharomyces cerevisiae4932EukaryoteYeast6Caenorhabditis elegans6239EukaryoteRoundworm4Arabidopsis thaliana3702EukaryoteThale cress23Pseudomonas aeruginosa287Prokaryote10Drosophila melanogaster7227EukaryoteFruit fly49Bathymodiolus platifrons220390EukaryoteDeep sea mussel2Bacteria2ProkaryoteBacteria19Schizosaccharomyces pombe4896Eukaryote21Xenopus laevis8355EukaryoteAfrican clawed frog25Escherichia coli (strain K12)83333Prokaryote60Nitzschia sp.0001EukaryoteNitzschia4157Acinetobacter baumannii 107673Prokaryote13Endoplasmic ReticulumGO:00057837Endoplasmic Reticulum MembraneGO:00057895CytoplasmGO:00057372MitochondrionGO:00057394PeroxisomeGO:00057771CytosolGO:000582910Cell MembraneGO:000588619Sarcoplasmic ReticulumGO:001652935ChloroplastGO:00095073Mitochondrial MatrixGO:000575936MembraneGO:001602032Inner MembraneGO:00702586LysosomeGO:000576416Lysosomal LumenGO:004320211Extracellular SpaceGO:000561518Melanosome MembraneGO:003316214Mitochondrial Outer MembraneGO:000574124Mitochondrial Intermembrane SpaceGO:000575812Mitochondrial Inner MembraneGO:000574325Golgi ApparatusGO:000579420Endoplasmic Reticulum LumenGO:000578821SynapseGO:004520215NucleusGO:000563431Periplasmic SpaceGO:000562053Endoplasmic Reticulum BodyGO:001016834Plant-Type VacuoleGO:000032540PeriplasmGO:00425978Smooth Endoplasmic Reticulum GO:000579027Peroxisome MembraneGO:000577826Golgi Apparatus MembraneGO:000013939Mitochondrial membraneGO:00319661LiverBTO:00007597295cardiocyteBTO:00015392Endothelium BTO:00003934Adrenal MedullaBTO:000004971825IntestineBTO:000064828StomachBTO:0001307155267Nervous SystemBTO:00014848Blood VesselBTO:0001102741111HeartBTO:000056273106KidneyBTO:00006717189MuscleBTO:00008871411824BrainBTO:0000142891618PancreasBTO:000098822BladderBTO:0000123181311PW_BS00001813013121PW_BS0001301251351PW_BS00012513613171PW_BS000136101711PW_BS00001033217121PW_BS0000281231751PW_BS00012344717171PW_BS0001158511PW_BS0000083211PW_BS0000035411PW_BS0000052111PW_BS00000229111PW_BS00002949711PW_BS000049311511PW_BS00003114101PW_BS0000141115121PW_BS00011110813PW_BS0001081471241PW_BS00014715924PW_BS0001593551914PW_BS000035117131PW_BS000117188118PW_BS0000241632181PW_BS000163205561PW_BS0000241601181PW_BS0001602137181PW_BS00002421013181PW_BS00002421217181PW_BS00002417018PW_BS0001702253541PW_BS000024151141PW_BS000151224241PW_BS0000241985181PW_BS0000242111018PW_BS000024222341PW_BS0000241644PW_BS0001642863641PW_BS000024226441PW_BS0000242491341PW_BS000024315123PW_BS0000243221231PW_BS00002429341PW_BS0000241321121PW_BS0001323317121PW_BS0000281122121PW_BS0001121151012PW_BS0001153361121PW_BS0000281192171PW_BS000119943PW_BS000094407251PW_BS000115405105PW_BS000115122551PW_BS000122429151PW_BS000115124151PW_BS000124383751PW_BS0001003761017PW_BS0000531355171PW_BS0001354641171PW_BS0001151181171PW_BS0001183987171PW_BS0001134812101PW_BS0001152975101PW_BS0000242991101PW_BS0000244957101PW_BS000115206261PW_BS000024388161PW_BS000112390761PW_BS000112168321PW_BS0001689611PW_BS00000916212PW_BS0000162811611PW_BS000028204111PW_BS00002015111PW_BS0000154311PW_BS000004331811PW_BS0000332441011PW_BS000024221411PW_BS000022422411PW_BS00004213121PW_BS000013126651PW_BS00012612711651PW_BS0001272164181PW_BS0000242156181PW_BS0000242916491PW_BS0000242924491PW_BS00002429817101PW_BS00002430013101PW_BS0000243016101PW_BS000024302116101PW_BS0000242231241PW_BS000024171211PW_BS0000172941141PW_BS00002413412121PW_BS0001341136121PW_BS0001133344121PW_BS000028337116121PW_BS00002812915121PW_BS00012934141121PW_BS0000281141112PW_BS0001141333121PW_BS00013332914121PW_BS00002834524121PW_BS00002834318121PW_BS000028360410121PW_BS000028408451PW_BS0001154141551PW_BS000115409115PW_BS000115406351PW_BS0001154151851PW_BS00011543441051PW_BS0001153821451PW_BS0001004182451PW_BS0001153841251PW_BS0001003744171PW_BS0000534436171PW_BS000115448116171PW_BS00011545015171PW_BS0001151371117PW_BS0001371203171PW_BS00012045118171PW_BS000115469410171PW_BS00011539914171PW_BS00011345424171PW_BS00011512112171PW_BS0001214824101PW_BS0001154781010PW_BS0001154831110PW_BS0001154793101PW_BS00011548414101PW_BS00011548924101PW_BS00011548012101PW_BS000115502461PW_BS000115207661PW_BS000024209106PW_BS000024208116PW_BS000024501361PW_BS0001155041861PW_BS00011551541061PW_BS0001153891461PW_BS0001123951361PW_BS0001135062461PW_BS0001153911261PW_BS000112541315PW_BS000054432511PW_BS00004360251PW_BS00006046114PW_BS0000467028511PW_BS00007072513PW_BS000072612517PW_BS0000613612011PW_BS0000363772113PW_BS00003793252011PW_BS00009327151PW_BS000027711PW_BS000007971521PW_BS000097100521PW_BS000100103331PW_BS000103105113PW_BS000105110231PW_BS0001106131PW_BS000006140103PW_BS000140101531PW_BS00010114315191PW_BS0001431465191PW_BS000146107313PW_BS000107951721PW_BS0000951553241PW_BS0001551572241PW_BS0001571613181PW_BS00016111PW_BS00000116611PW_BS0001661783211PW_BS0001781802211PW_BS00018015284PW_BS00015221425181PW_BS0000241901118PW_BS00002416212181PW_BS000162261115PW_BS0000262771218PW_BS0000242811251PW_BS0000242851041PW_BS0000242875341PW_BS0000242273441PW_BS00002465111PW_BS0000652905491PW_BS0000243081011PW_BS0000243183123PW_BS000024253541PW_BS0000243331212PW_BS00002834713125PW_BS0000283522512PW_BS00002835325127PW_BS00002835625121PW_BS0000283683601PW_BS0000283702601PW_BS000028228361PW_BS000024232403PW_BS000024412125PW_BS0001154251355PW_BS0001154192551PW_BS000115436255PW_BS0001154461217PW_BS00011546013175PW_BS00011545525171PW_BS0001154712517PW_BS00011547225177PW_BS00011548718101PW_BS00011549025101PW_BS0001155072561PW_BS0001155131761PW_BS0001157906111PW_BS0005248346111PW_BS000549185321PW_BS000024111811PW_BS00001114117191PW_BS00014178811PW_BS0000785181PW_BS000051682512PW_BS000068509516PW_BS00005085241011PW_BS0000851873118PW_BS000024711113PW_BS00007122014PW_BS0000242892491PW_BS0000243201123PW_BS00002434695126PW_BS00002832711125PW_BS0000284239556PW_BS0001154241155PW_BS00011545895176PW_BS00011545911175PW_BS0001158424111PW_BS00008459724112PW_BS000336397113PW_BS000039215114PW_BS000021592711PW_BS000059231511PW_BS000023918511PW_BS000091562611PW_BS0000561041431PW_BS00010419914181PW_BS0000242881441PW_BS00002433527121PW_BS000028184121PW_BS000024372102PW_BS0000284222751PW_BS00011537527171PW_BS00005349127101PW_BS0001155082761PW_BS0001158911421PW_BS000552471914PW_BS0000475811411PW_BS0000586618518PW_BS0000667413PW_BS0000743093911PW_BS00002436139121PW_BS0000283863951PW_BS00010040139171PW_BS000113818512PW_BS0005489731715PW_BS00056969181019PW_BS00006984711PW_BS000549392171PW_BS00017199611315PW_BS0005696361PW_BS0000639312011PW_BS000559913111575PW_BS0005587132210111PW_BS000512801111PW_BS00008048113PW_BS000048116220-Hydroxy-leukotriene B4HMDB000150920-hydroxy- Leukotriene B4 (20-OH-LTB4) is an omega-hydroxylated metabolite of leukotriene B4 in human neutrophils. Elevated urinary concentrations of 20-OH-LTB4 and LTB4 are found in patients with Sjogren-Larsson syndrome (SLS, OMIM 270220), an autosomal recessively inherited neurocutaneous disorder caused by a deficiency of the microsomal enzyme fatty aldehyde dehydrogenase (FALDH), which as an essential role in LTB4 metabolism. Preterm birth seems to be one of the features of the syndrome. The reason for the preterm birth is unclear. It is hypothesized that it relates to the defective LTB4 degradation in SLS. The pathological urinary excretion of LTB4 and 20-OH-LTB4 is a biochemical marker for SLS. Surprisingly, 20-OH-LTB4 concentrations are normal in CSF. Leukotriene B4 is the major metabolite in neutrophil polymorphonuclear leukocytes. Leukotrienes are metabolites of arachidonic acid derived from the action of 5-LO (5-lipoxygenase). The immediate product of 5-LO is LTA4 (leukotriene A4), which is enzymatically converted into either LTB4 (leukotriene B4) by LTA4 hydrolase or LTC4 (leukotriene C4) by LTC4 synthase. The regulation of leukotriene production occurs at various levels, including expression of 5-LO, translocation of 5-LO to the perinuclear region and phosphorylation to either enhance or inhibit the activity of 5-LO. Biologically active LTB4 is metabolized by w-oxidation carried out by specific cytochrome P450s (CYP4F) followed by beta-oxidation from the w-carboxy position and after CoA ester formation. Other specific pathways of leukotriene metabolism include the 12-hydroxydehydrogenase/ 15-oxo-prostaglandin-13-reductase that form a series of conjugated diene metabolites that have been observed to be excreted into human urine. Metabolism of LTC4 occurs by sequential peptide cleavage reactions involving a gamma-glutamyl transpeptidase that forms LTD4 (leukotriene D4) and a membrane-bound dipeptidase that converts LTD4 into LTE4 (leukotriene E4) before w-oxidation. These metabolic transformations of the primary leukotrienes are critical for termination of their biological activity, and defects in expression of participating enzymes may be involved in specific genetic disease. (PMID: 12709426, 9799565, 11408337, 17623009). Leukotrienes 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.79516-82-8C0485352807451564620-OH-LTB44444320OCCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=OC20H32O5InChI=1S/C20H32O5/c21-17-10-6-2-1-3-7-12-18(22)13-8-4-5-9-14-19(23)15-11-16-20(24)25/h3-5,7-9,13-14,18-19,21-23H,1-2,6,10-12,15-17H2,(H,24,25)/b5-4+,7-3-,13-8+,14-9-/t18-,19-/m1/s1PTJFJXLGRSTECQ-PSPARDEHSA-N(5S,6Z,8E,10E,12R,14Z)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoic acid352.4651352.224974134-4.03420-hydroxy-LTB40-1FDB022663(5s,12r)-5,12,20-trihydroxy-(6z,8e,10e,14z)-eicosatetraenoate;(5s,12r)-5,12,20-trihydroxy-(6z,8e,10e,14z)-eicosatetraenoic acid;(5s,6z,8e,10e,12r,14z)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoate;(5s,6z,8e,10e,12r,14z)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoic acid;(6z,8e,10e,14z)-(5s,12r)-5,12,20-trihydroxyeicosa-6,8,10,14-tetraenoate;(6z,8e,10e,14z)-(5s,12r)-5,12,20-trihydroxyeicosa-6,8,10,14-tetraenoic acid;(6z,8e,10e,14z)-(5s,12r)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoate;(6z,8e,10e,14z)-(5s,12r)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoic acid;20-hydroxy ltb4;20-hydroxy-ltb4;20-hydroxy-leukotriene b4;20-hydroxyleukotriene b4;20-oh-5s,12s-dihydroxy-6,10-trans-8,14-cis-eicosatetraenoate;20-oh-5s,12s-dihydroxy-6,10-trans-8,14-cis-eicosatetraenoic acid;20-oh-ltb4;20-oh-leukotriene b4;5,12,20-thete;5,12,20-trihete;5s,12r,20-trihydroxy-6z,8e,10e,14z-eicosatetraenoate;5s,12r,20-trihydroxy-6z,8e,10e,14z-eicosatetraenoic acid;Omega-hydroxy-ltb4;[s-[r*,s*-(e,z,e,z)]]-5,12,20-trihydroxy-6,8,10,14-eicosatetraenoate;[s-[r*,s*-(e,z,e,z)]]-5,12,20-trihydroxy-6,8,10,14-eicosatetraenoic acid;W-hydroxy-ltb4PW_C001162HLeukB413301877391130121061125123625136264420-Carboxy-leukotriene B4HMDB000605920-Carboxyleukotriene B4 is an omega-oxidized metabolite of leukotriene B4 (LTB4). Neutrophil microsomes are known to oxidize 20-hydroxy-LTB4 (20-OH-LTB4) to its 20-oxo and 20-carboxy derivatives in the presence of NADPH. This activity has been ascribed to LTB4 omega-hydroxylase (cytochrome P-450LTB omega). Leukotriene B4 release from polymorphonuclear granulocytes of severely burned patients was reduced as compared to healthy donor cells. This decrease is due to an enhanced conversion of LTB4 into the 20-hydroxy- and 20-carboxy-metabolites and further to a decreased LTB4-synthesis. LTB4 is the major metabolite in neutrophil polymorphonuclear leukocytes. Leukotrienes are metabolites of arachidonic acid derived from the action of 5-LO (5-lipoxygenase). The immediate product of 5-LO is LTA4 (leukotriene A4), which is enzymatically converted into either LTB4 (leukotriene B4) by LTA4 hydrolase or LTC4 (leukotriene C4) by LTC4 synthase. The regulation of leukotriene production occurs at various levels, including expression of 5-LO, translocation of 5-LO to the perinuclear region and phosphorylation to either enhance or inhibit the activity of 5-LO. Biologically active LTB4 is metabolized by w-oxidation carried out by specific cytochrome P450s (CYP4F) followed by beta-oxidation from the w-carboxy position and after CoA ester formation. Other specific pathways of leukotriene metabolism include the 12-hydroxydehydrogenase/ 15-oxo-prostaglandin-13-reductase that form a series of conjugated diene metabolites that have been observed to be excreted into human urine. Metabolism of LTC4 occurs by sequential peptide cleavage reactions involving a gamma-glutamyl transpeptidase that forms LTD4 (leukotriene D4) and a membrane-bound dipeptidase that converts LTD4 into LTE4 (leukotriene E4) before w-oxidation. These metabolic transformations of the primary leukotrienes are critical for termination of their biological activity, and defects in expression of participating enzymes may be involved in specific genetic disease. (PMID 17623009, 7633595, 2155225, 3039534)Leukotrienes 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.80434-82-8C059505280877275624444400O[C@@H](CCCC(O)=O)\C=C/C=C/C=C/[C@H](O)C\C=C/CCCCC(O)=OC20H30O6InChI=1S/C20H30O6/c21-17(11-6-2-1-3-9-15-19(23)24)12-7-4-5-8-13-18(22)14-10-16-20(25)26/h2,4-8,12-13,17-18,21-22H,1,3,9-11,14-16H2,(H,23,24)(H,25,26)/b5-4+,6-2-,12-7+,13-8-/t17-,18-/m1/s1SXWGPVJGNOLNHT-VFLUTPEKSA-N(5S,6Z,8E,10E,12R,14Z)-5,12-dihydroxyicosa-6,8,10,14-tetraenedioic acid366.4486366.204238692-3.91420-cooh-LTB40-2FDB023824(5s,6z,8e,10e,12r,14z)-5,12-dihydroxyicosa-6,8,10,14-tetraenedioate;(5s,6z,8e,10e,12r,14z)-5,12-dihydroxyicosa-6,8,10,14-tetraenedioic acid;(s-(r*,s*-(e,z,e,z)))-5,12-dihydroxy-6,8,10,14-eicosatetraenedioate;(s-(r*,s*-(e,z,e,z)))-5,12-dihydroxy-6,8,10,14-eicosatetraenedioic acid;20-cooh-ltb4;20-cooh-leukotriene b4;20-carboxy-ltb4;20-carboxy-leukotriene- b4;20-carboxyleukotriene b4;20-hydroxy-20-oxo-leukotriene b4;5(s),12(r)-dihydroxy-20-carboxy-6,8,10,14-eicosatetraenoate;5(s),12(r)-dihydroxy-20-carboxy-6,8,10,14-eicosatetraenoic acid;5,12-dihydroxy-delta5,8,11,14-eicosapolyendioate;5,12-dihydroxy-delta5,8,11,14-eicosapolyendioic acid;5s,12r-dihydroxy-6z,8e,10e,14z-eicosatetraene-1,20-dioate;5s,12r-dihydroxy-6z,8e,10e,14z-eicosatetraene-1,20-dioic acid;20-carboxy-leukotriene b4;5,12-dihydroxy-δ5,8,11,14-eicosapolyendioate;5,12-dihydroxy-δ5,8,11,14-eicosapolyendioic acidPW_C00264420CLuB413311877392130121062125123626136853Leukotriene B4HMDB0001085Leukotriene B4 is the major metabolite in neutrophil polymorphonuclear leukocytes. Leukotrienes are metabolites of arachidonic acid derived from the action of 5-LO (5-lipoxygenase). The immediate product of 5-LO is LTA4 (leukotriene A4), which is enzymatically converted into either LTB4 (leukotriene B4) by LTA4 hydrolase or LTC4 (leukotriene C4) by LTC4 synthase. The regulation of leukotriene production occurs at various levels, including expression of 5-LO, translocation of 5-LO to the perinuclear region and phosphorylation to either enhance or inhibit the activity of 5-LO. Biologically active LTB4 is metabolized by w-oxidation carried out by specific cytochrome P450s (CYP4F) followed by b-oxidation from the w-carboxy position and after CoA ester formation. Other specific pathways of leukotriene metabolism include the 12-hydroxydehydrogenase/ 15-oxo-prostaglandin-13-reductase that form a series of conjugated diene metabolites that have been observed to be excreted into human urine. Metabolism of LTC4 occurs by sequential peptide cleavage reactions involving a gamma-glutamyl transpeptidase that forms LTD4 (leukotriene D4) and a membrane-bound dipeptidase that converts LTD4 into LTE4 (leukotriene E4) before w-oxidation. These metabolic transformations of the primary leukotrienes are critical for termination of their biological activity, and defects in expression of participating enzymes may be involved in specific genetic disease. The term leukotriene was coined to indicate the presence of three conjugated double bonds within the 20-carbon structure of arachidonic acid as well as the fact that these compounds were derived from leucocytes such as PMNNs or transformed mast cells. Interestingly, most of the cells known to express 5-LO are of myeloid origin, which includes neutrophils, eosinophils, mast cells, macrophages, basophils and monocytes. Leukotriene biosynthesis begins with the specific oxidation of arachidonic acid by a free radical mechanism as a consequence of interaction with 5-LO. The first enzymatic step involves the abstraction of a hydrogen atom from C-7 of arachidonate followed by the addition of molecular oxygen to form 5-HpETE (5-hydroperoxyeicosatetraenoic acid). A second enzymatic step is also catalysed by 5-LO and involves removal of a hydrogen atom from C-10, resulting in formation of the conjugated triene epoxide LTA4. LTA4 must then be released by 5-LO and encounter either LTA4-H (LTA4 hydrolase) or LTC4-S [LTC4 (leukotriene C4) synthase]. LTA4-H can stereospecifically add water to C-12 while retaining a specific double-bond geometry, leading to LTB4 [leukotriene B4, 5(S),12(R)-dihydroxy-6,8,10,14-(Z,E,E,Z)-eicosatetraenoic acid]. If LTA4 encounters LTC4-S, then the reactive epoxide is opened at C-6 by the thiol anion of glutathione to form the product LTC4 [5(S)-hydroxy-6(R)-S-glutathyionyl-7,9,11,14- (E,E,Z,Z)-eicosatetraenoic acid], essentially a glutathionyl adduct of oxidized arachidonic acid. Both of these terminal leukotrienes are biologically active in that specific GPCRs recognize these chemical structures and receptor recognition initiates complex intracellular signalling cascades. In order for these molecules to serve as lipid mediators, however, they must be released from the biosynthetic cell into the extracellular milieu so that they can encounter the corresponding GPCRs. Surprising features of this cascade include the recognition of the assembly of critical enzymes at the perinuclear region of the cell and even localization of 5-LO within the nucleus of some cells. Under some situations, the budding phagosome has been found to assemble these proteins. Non-enzymatic proteins such as FLAP are now known as critical partners of this protein-machine assembly. An unexpected pathway of leukotriene biosynthesis involves the transfer of the chemically reactive intermediate, LTA4, from the biosynthetic cell followed by conversion into LTB4 or LTC4 by other cells that do not express 5-LO. (PMID 17623009). Leukotrienes 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.71160-24-2C021655280492156476Z8E10E14Z-5S12R-512-DIHYDROXYI4444132CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C\[C@@H](O)CCCC(O)=OC20H32O4InChI=1S/C20H32O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h6-11,14-15,18-19,21-22H,2-5,12-13,16-17H2,1H3,(H,23,24)/b8-7+,9-6-,14-10+,15-11+/t18-,19-/m1/s1VNYSSYRCGWBHLG-UKNWISKWSA-N(5S,6E,8E,10E,12R,14Z)-5,12-dihydroxyicosa-6,8,10,14-tetraenoic acid336.4657336.230059512-4.3436-trans-LTB40-1FDB022416(6z,8e,10e,14z)-(5s,12r)-5,12-dihydroxyicosa-6,8,10,14-tetraenoate;(6z,8e,10e,14z)-(5s,12r)-5,12-dihydroxyicosa-6,8,10,14-tetraenoic acid;5,12-dihete;5,12-dihydroxy-6,10-trans -8,14-cis -eicosatetraenoate;5,12-dihydroxy-6,10-trans -8,14-cis -eicosatetraenoic acid;Leukotriene b4 ethanol solution;(5s,12r,6z,8e,10e,14z)-5,12-dihydroxy-6,8,10,14-eicosatetraenoic acid;(5s,6z,8e,10e,12r,14z)-5,12-dihydroxyeicosa-6,8,10,14-tetraenoic acid;(s-(r*,s*-(e,z,e,z)))-5,12-dihydroxy-6,8,10,14-eicosatetraenoic acid;5(s),12(r)-dihydroxy-6(z),8(e),10(e),14(z)-eicosatetraenoic acid;5(s),12(r)-dihydroxy-6(z),8(e),10(e),14(z)-icosatetraenoic acid;5,12-hete;5s,12r-dihydroxy-6z,8e,10e,14z-eicosatetraenoic acid;Ltb4;(5s,12r,6z,8e,10e,14z)-5,12-dihydroxy-6,8,10,14-eicosatetraenoate;(5s,6z,8e,10e,12r,14z)-5,12-dihydroxyeicosa-6,8,10,14-tetraenoate;(s-(r*,s*-(e,z,e,z)))-5,12-dihydroxy-6,8,10,14-eicosatetraenoate;5(s),12(r)-dihydroxy-6(z),8(e),10(e),14(z)-eicosatetraenoate;5(s),12(r)-dihydroxy-6(z),8(e),10(e),14(z)-icosatetraenoate;5s,12r-dihydroxy-6z,8e,10e,14z-eicosatetraenoatePW_C000853LTB413321077393332121063123123627447146NADPHHMDB0000221Nicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5'-phosphate (NMN) coupled by pyrophosphate linkage to the 5'-phosphate adenosine 2',5'-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed.).53-57-6C000052283351216474NADPH17215925NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1OC21H30N7O17P3InChI=1S/C21H30N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1,3-4,7-8,10-11,13-16,20-21,29-31H,2,5-6H2,(H2,23,32)(H,36,37)(H,38,39)(H2,22,24,25)(H2,33,34,35)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1ACFIXJIJDZMPPO-NNYOXOHSSA-N{[(2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-5-[({[({[(2R,3S,4R,5R)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid745.4209745.091102105-2.149nadph0-4FDB0219092'-(dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-b-d-ribofuranosylnicotinamide;2'-(dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosylnicotinamide;Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-d-ribofuranosyl-3-pyridinecarboxamide;Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosyl-3-pyridinecarboxamide;Dihydrocodehydrogenase ii;Dihydronicotinamide adenine dinucleotide phosphate;Dihydronicotinamide adenine dinucleotide-p;Dihydrotriphosphopyridine nucleotide reduced;Nadp-reduced;Nadph;Nicotinamide-adenine-dinucleotide-phosphorate;Nicotinamide-adenine-dinucleotide-phosphoric acid;Reduced codehydrase ii;Reduced coenzyme ii;Reduced cozymase ii;Reduced triphosphopyridine nucleotide;Triphosphopyridine nucleotide reduced;B-nadph;B-nicotinamide-adenine-dinucleotide-phosphorate;B-nicotinamide-adenine-dinucleotide-phosphoric acid;Beta-nadph;Beta-nicotinamide-adenine-dinucleotide-phosphorate;Beta-nicotinamide-adenine-dinucleotide-phosphoric acid;Nicotinamide adenine dinucleotide phosphate - reducedPW_C000146NADPH185819037781079658211883721609291615494687314793144797145310111578910859721476128159627135677911770681887103163715420572051607315213734521075592127591170819422582191518421224118121981189321112006222121501641224528612596226126482494234331543746322769112937716613277385331773943327746013077504112775111157762333680712119113164941201054071204254051204521221206161231211411251212754291214021241214833831230593761230861351232414471237121361238464641239611181240413981254724811256962971262142991265294951270092061275723881281013901407061681065OxygenHMDB0001377Oxygen is the third most abundant element in the universe after hydrogen and helium and the most abundant element by mass in the Earth's crust. Diatomic oxygen gas constitutes 20.9% of the volume of air. All major classes of structural molecules in living organisms, such as proteins, carbohydrates, and fats, contain oxygen, as do the major inorganic compounds that comprise animal shells, teeth, and bone. Oxygen in the form of O2 is produced from water by cyanobacteria, algae and plants during photosynthesis and is used in cellular respiration for all living organisms. Green algae and cyanobacteria in marine environments provide about 70% of the free oxygen produced on earth and the rest is produced by terrestrial plants. Oxygen is used in mitochondria to help generate adenosine triphosphate (ATP) during oxidative phosphorylation. For animals, a constant supply of oxygen is indispensable for cardiac viability and function. To meet this demand, an adult human, at rest, inhales 1.8 to 2.4 grams of oxygen per minute. This amounts to more than 6 billion tonnes of oxygen inhaled by humanity per year. At a resting pulse rate, the heart consumes approximately 8-15 ml O2/min/100 g tissue. This is significantly more than that consumed by the brain (approximately 3 ml O2/min/100 g tissue) and can increase to more than 70 ml O2/min/100 g myocardial tissue during vigorous exercise. As a general rule, mammalian heart muscle cannot produce enough energy under anaerobic conditions to maintain essential cellular processes; thus, a constant supply of oxygen is indispensable to sustain cardiac function and viability. However, the role of oxygen and oxygen-associated processes in living systems is complex, and they and can be either beneficial or contribute to cardiac dysfunction and death (through reactive oxygen species). Reactive oxygen species (ROS) are a family of oxygen-derived free radicals that are produced in mammalian cells under normal and pathologic conditions. Many ROS, such as the superoxide anion (O2-)and hydrogen peroxide (H2O2), act within blood vessels, altering mechanisms mediating mechanical signal transduction and autoregulation of cerebral blood flow. Reactive oxygen species are believed to be involved in cellular signaling in blood vessels in both normal and pathologic states. The major pathway for the production of ROS is by way of the one-electron reduction of molecular oxygen to form an oxygen radical, the superoxide anion (O2-). Within the vasculature there are several enzymatic sources of O2-, including xanthine oxidase, the mitochondrial electron transport chain, and nitric oxide (NO) synthases. Studies in recent years, however, suggest that the major contributor to O2- levels in vascular cells is the membrane-bound enzyme NADPH-oxidase. Produced O2- can react with other radicals, such as NO, or spontaneously dismutate to produce hydrogen peroxide (H2O2). In cells, the latter reaction is an important pathway for normal O2- breakdown and is usually catalyzed by the enzyme superoxide dismutase (SOD). Once formed, H2O2 can undergo various reactions, both enzymatic and nonenzymatic. The antioxidant enzymes catalase and glutathione peroxidase act to limit ROS accumulation within cells by breaking down H2O2 to H2O. Metabolism of H2O2 can also produce other, more damaging ROS. For example, the endogenous enzyme myeloperoxidase uses H2O2 as a substrate to form the highly reactive compound hypochlorous acid. Alternatively, H2O2 can undergo Fenton or Haber-Weiss chemistry, reacting with Fe2+/Fe3+ ions to form toxic hydroxyl radicals (-.OH). (PMID: 17027622, 15765131).7782-44-7C0000797715379CPD-6641952O=OO2InChI=1S/O2/c1-2MYMOFIZGZYHOMD-UHFFFAOYSA-Ndioxygen31.998831.9898292440singlet oxygen00FDB022589Dioxygen;Molecular oxygen;O2;Oxygen;Oxygen molecule;[oo];Dioxygene;Disauerstoff;E 948;E-948;E948PW_C001065O295911052451650018505854914625286383649106743168820754157634769338362137549201624253122280329426042474713546712354801255493126550812758091085973147612915970061887032163705016073192137533210756021283951511181621611864198118832151189421112057225120631641224728612279226123252491270629112716292130042981301630013026301130383021326022342276174265731576910293770442947721413477350111773631307737733177395332774971137751211577537334776263367772333777736112777471297775634177805114778121337807032978151132783813457880534379111360120047408120383122120426405120542407120553414120594409120601406120883415121045124121104383121605434121656429122117382122573418122689384122798374122822443123027135123060376123128447123139136123163448123176119123187450123219137123226120123459451123609118123669398124163469124214464124669399125145454125275121125425482125706478125731483125737297125740479125884481126100299126272484126522495126721489126825480126964502126986207127198209127214208127219205127222501127305504127345206127557388127574515127835389128081395128095390128312506128432391143NADPHMDB0000217Nicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5-phosphate (NMN) coupled by pyrophosphate linkage to the 5-phosphate adenosine 2,5-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed.) Hydrogen carrier in biochemical redox systems. In the hexose monophosphoric acid system it is reduced to Dihydrocoenzyme II and reoxidation in the presence of flavoproteins (Dictionary of Organic Compounds).53-59-8C00006588618009NAD(P)5675NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP([O-])(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1OC21H28N7O17P3InChI=1S/C21H28N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1-4,7-8,10-11,13-16,20-21,29-31H,5-6H2,(H7-,22,23,24,25,32,33,34,35,36,37,38,39)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1XJLXINKUBYWONI-NNYOXOHSSA-N1-[(2R,3R,4S,5R)-5-{[({[(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl phosphono)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium743.405743.075452041-2.2281-[(2R,3R,4S,5R)-5-[({[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl phosphono}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium0-3FDB021908Adenine-nicotinamide dinucleotide phosphate;Codehydrase ii;Codehydrogenase ii;Coenzyme ii;Cozymase ii;Nad phosphate;Nadp;Nadp+;Nicotinamide adenine dinucleotide phosphate;Nicotinamide-adenine dinucleotide phosphate;Tpn;Triphosphopyridine nucleotide;B-nadp;B-nicotinamide adenine dinucleotide phosphate;B-tpn;Beta-nadp;Beta-nicotinamide adenine dinucleotide phosphate;Beta-tpn;Oxidized nicotinamide-adenine dinucleotide phosphate;B-nicotinamide adenine dinucleotide phosphoric acid;Beta-nicotinamide adenine dinucleotide phosphoric acid;β-nicotinamide adenine dinucleotide phosphate;β-nicotinamide adenine dinucleotide phosphoric acidPW_C000143NADP18381913768578010824188392161129161749468531479614480114530811157901086017147613215962733567781177069188710516371522057206160731721373462107562212758917081972258220151841922411811198118972111200822212152164122492861259722612650249423443154374532276913293771641327738433177396332774611307751511577624336778143347787011280713119113165941201064071204294051204501221206044081206181231211421251212774291214011241214853831230633761230841351232293741232434471237131361238484641239601181240433981254734811256942971257434821262152991265284951270102061272255021275703881281003901407091681420WaterHMDB0002111Water is a chemical substance that is essential to all known forms of life. It appears colorless to the naked eye in small quantities, though it is actually slightly blue in color. It covers 71% of Earth's surface. Current estimates suggest that there are 1.4 billion cubic kilometers (330 million m3) of it available on Earth, and it exists in many forms. It appears mostly in the oceans (saltwater) and polar ice caps, but it is also present as clouds, rain water, rivers, freshwater aquifers, lakes, and sea ice. Water in these bodies perpetually moves through a cycle of evaporation, precipitation, and runoff to the sea. Clean water is essential to human life. In many parts of the world, it is in short supply. From a biological standpoint, water has many distinct properties that are critical for the proliferation of life that set it apart from other substances. It carries out this role by allowing organic compounds to react in ways that ultimately allow replication. All known forms of life depend on water. Water is vital both as a solvent in which many of the body's solutes dissolve and as an essential part of many metabolic processes within the body. Metabolism is the sum total of anabolism and catabolism. In anabolism, water is removed from molecules (through energy requiring enzymatic chemical reactions) in order to grow larger molecules (e.g. starches, triglycerides and proteins for storage of fuels and information). In catabolism, water is used to break bonds in order to generate smaller molecules (e.g. glucose, fatty acids and amino acids to be used for fuels for energy use or other purposes). Water is thus essential and central to these metabolic processes. Water is also central to photosynthesis and respiration. Photosynthetic cells use the sun's energy to split off water's hydrogen from oxygen. Hydrogen is combined with CO2 (absorbed from air or water) to form glucose and release oxygen. All living cells use such fuels and oxidize the hydrogen and carbon to capture the sun's energy and reform water and CO2 in the process (cellular respiration). Water is also central to acid-base neutrality and enzyme function. An acid, a hydrogen ion (H+, that is, a proton) donor, can be neutralized by a base, a proton acceptor such as hydroxide ion (OH-) to form water. Water is considered to be neutral, with a pH (the negative log of the hydrogen ion concentration) of 7. Acids have pH values less than 7 while bases have values greater than 7. Stomach acid (HCl) is useful to digestion. However, its corrosive effect on the esophagus during reflux can temporarily be neutralized by ingestion of a base such as aluminum hydroxide to produce the neutral molecules water and the salt aluminum chloride. Human biochemistry that involves enzymes usually performs optimally around a biologically neutral pH of 7.4. (Wikipedia).7732-18-5C0000196215377937OH2OInChI=1S/H2O/h1H2XLYOFNOQVPJJNP-UHFFFAOYSA-Nwater18.015318.0105646861water00FDB013390Dihydrogen oxide;Steam;[oh2];Acqua;Agua;Aqua;Bound water;Dihydridooxygen;Eau;H2o;Hoh;Hydrogen hydroxide;WasserPW_C001420H2O55894910951394151316214481135261562428652106912077033823188382109431137749146554159043201824253222267860272746277817280529314370316472363461459836472737494193503027515675195975214100522794523610352971055319111534311353551125402110547012354831255492126550712755341305537114554112955911355608118562210856916575914057781015841143585314658771075890955910147594015160321556059157608716161231636133159621516218166647717865071806600152671311768401886888160716220571812077193206721121172282137238214724321572951987350216738821074012127467222749222475001907588170820122582372268414162926526118502771192216412011281122132851225028612264287123272491252022712632651269329012705291127152921300729813019300130253011303730213261223133272941534030842327315426953184369132276914293770192537710213277131133772151347737833177397332774713337751611577536334776283367772233777759341778163437798234778071329782353527824235378270356791133608001436880039370805912288065611993830383947943841105573901106393911158443981198792321199151221199634061200084071200464081201131241203654121204304051204384091206064151207944141211584251212404291213511211213814191216074341221183821223844361227531201227973741228044431230124461230643761230721371231314471231421361231624481232314511233844501237304601238104641239404551241654691246703991249384711249454721253052971253534791253864811254244821254802991256824831257074781257454871260544901262384951262734841267644801268965011269635021270173881271772081271992091272275041275065071275765151278363891280823951281765131406747901406758341407551851799HemeHMDB0003178Heme is the color-furnishing portion of hemoglobin. It is found free in tissues and as the prosthetic group in many hemeproteins. A heme or haem is a prosthetic group that consists of an iron atom contained in the center of a large heterocyclic organic ring called a porphyrin. Not all porphyrins contain iron, but a substantial fraction of porphyrin-containing metalloproteins have heme as their prosthetic subunit; these are known as hemoproteins.14875-96-8C0003217627HEME_A24604415DB02577CC1=C(CCC(O)=O)C2=CC3=[N+]4C(=CC5=C(C)C(C=C)=C6C=C7C(C)=C(C=C)C8=[N+]7[Fe--]4(N2C1=C8)N56)C(C)=C3CCC(O)=OC34H32FeN4O4InChI=1S/C34H34N4O4.Fe/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25;/h7-8,13-16H,1-2,9-12H2,3-6H3,(H4,35,36,37,38,39,40,41,42);/q;+2/p-2/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-;KABFMIBPWCXCRK-RGGAHWMASA-L4,20-bis(2-carboxyethyl)-10,15-diethenyl-5,9,14,19-tetramethyl-2lambda5,22,23lambda5,25-tetraaza-1-ferraoctacyclo[11.9.1.1^{1,8}.1^{3,21}.0^{2,6}.0^{16,23}.0^{18,22}.0^{11,25}]pentacosa-2,4,6,8,10,12,14,16(23),17,19,21(24)-undecaene-2,23-bis(ylium)-1,1-diuide616.487616.177297665-5.4824,20-bis(2-carboxyethyl)-10,15-diethenyl-5,9,14,19-tetramethyl-2lambda5,22,23lambda5,25-tetraaza-1-ferraoctacyclo[11.9.1.1^{1,8}.1^{3,21}.0^{2,6}.0^{16,23}.0^{18,22}.0^{11,25}]pentacosa-2,4,6,8,10,12,14,16(23),17,19,21(24)-undecaene-2,23-bis(ylium)-1,1-diuide0-2FDB016272(protoporphyrinato)iron;Ferroheme;Ferroheme b;Ferroprotoheme;Ferroprotoporphyrin;Ferroprotoporphyrin ix;Ferrous protoheme;Ferrous protoheme ix;Haem;Hem;Heme;Iron protoporphyrin;Iron protoporphyrin ix;Iron(ii) protoporphyrin ix;Protoferroheme;Protohaem;Protoheme;Protoheme ix;Reduced hematinPW_C001799Heme2471630810324860827665124431354491413361963182806292938932381133672634211437344404331482328517095547212354851255517129583014162467862831659715170441607060161732621311835198118982111206516413009298130213004227817769152937693124977351111773641307736733177398332775171157762933677813334783801337860213278963112799321341204314051206034081209554071210853831216584291217461241219101221225704061226913841230653761231334471231441361232283741235211191236503981242164641242971181244631351251421201252771211257424821258964811261962991264992971265124951267184791268274801272245021273572061276323881280702051280833951280863901283095011284343911030Leukotriene A4HMDB0001337Leukotriene A4 (LTA4) is the first metabolite in the series of reactions leading to the synthesis of all leukotrienes. 5-Lipoxygenase (5-LO) catalyzes the two-step conversion of arachidonic acid to LTA4.The first step consists of the oxidation of arachidonic acid to the unstable intermediate 5-hydroperoxyeicosatetraenoic acid (5-HPETE), and the second step is the dehydration of 5-HPETE to form LTA4. Leukotriene A4, an unstable epoxide, is hydrolyzed to leukotriene B4 or conjugated with glutathione to yield leukotriene C4 and its metabolites, leukotriene D4 and leukotriene E4. The leukotrienes participate in host defense reactions and pathophysiological conditions such as immediate hypersensitivity and inflammation. Recent studies also suggest a neuroendocrine role for leukotriene C4 in luteinizing hormone secretion. (PMID: 10591081, 2820055). Leukotrienes 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.72059-45-1C00909528038315651CPD-88924444074CCCCC\C=C/C\C=C/C=C/C=C/[C@@H]1O[C@H]1CCCC(O)=OC20H30O3InChI=1S/C20H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-15-18-19(23-18)16-14-17-20(21)22/h6-7,9-13,15,18-19H,2-5,8,14,16-17H2,1H3,(H,21,22)/b7-6-,10-9-,12-11+,15-13+/t18-,19-/m0/s1UFPQIRYSPUYQHK-WAQVJNLQSA-N4-[(2S,3S)-3-[(1E,3E,5Z,8Z)-tetradeca-1,3,5,8-tetraen-1-yl]oxiran-2-yl]butanoic acid318.4504318.219494826-5.881leukotriene A40-1FDB022561(5s,6s,7e,9e,11z,14z)-5,6-epoxyicosa-7,9,11,14-tetraenoate;(5s,6s,7e,9e,11z,14z)-5,6-epoxyicosa-7,9,11,14-tetraenoic acid;(7e,9e,11z,14z)-(5s,6s)-5,6-epoxyeicosa-7,9,11,14-tetraenoate;(7e,9e,11z,14z)-(5s,6s)-5,6-epoxyeicosa-7,9,11,14-tetraenoic acid;(7e,9e,11z,14z)-(5s,6s)-5,6-epoxyicosa- 7,9,11,14-tetraenoate;(7e,9e,11z,14z)-(5s,6s)-5,6-epoxyicosa- 7,9,11,14-tetraenoic acid;(7e,9e,11z,14z)-(5s,6s)-5,6-epoxyicosa-7,9,11,14-tetrenoioc acid;5s,6s-epoxy-7e,9e,11z,14z-eicosatetraenoate;5s,6s-epoxy-7e,9e,11z,14z-eicosatetraenoic acid;Lta4;(7e,9e,11z,14z)-(5s,6s)-5,6-epoxyicosa-7,9,11,14-tetraenoate;5(s)-5,6-oxido-7,9-trans-11,14-cis-eicosatetraenoic acid;5s,6s-leukotriene a4;(7e,9e,11z,14z)-(5s,6s)-5,6-epoxyicosa-7,9,11,14-tetraenoic acid;5(s)-5,6-oxido-7,9-trans-11,14-cis-eicosatetraenoatePW_C001030LTA413348774001111210641221236291351005Zinc (II) ionHMDB0001303Zinc is an essential element, necessary for sustaining all life.Physiologically, it exists as an ion in the body. It is estimated that 3000 of the hundreds of thousands of proteins in the human body contain zinc prosthetic groups. In addition, there are over a dozen types of cells in the human body that secrete zinc ions, and the roles of these secreted zinc signals in medicine and health are now being actively studied. Intriguingly, brain cells in the mammalian forebrain are one type of cell that secretes zinc, along with its other neuronal messenger substances. Cells in the salivary gland, prostate, immune system and intestine are other types that secrete zinc. Obtaining a sufficient zinc intake during pregnancy and in young children is a problem, especially among those who cannot afford a good and varied diet. Brain development is stunted by zinc deficiency in utero and in youth. Zinc is an activator of certain enzymes, such as carbonic anhydrase. Carbonic anhydrase is important in the transport of carbon dioxide in vertebrate blood. Even though zinc is an essential requirement for a healthy body, too much zinc can be harmful. Excessive absorption of zinc can also suppress copper and iron absorption. The free zinc ion in solution is highly toxic to plants, invertebrates, and even vertebrate fish. The Free Ion Activity Model (FIAM) is well-established in the literature, and shows that just micromolar amounts of the free ion kills some organisms.23713-49-7C000383205129105ZN%2b229723DB01593[Zn++]ZnInChI=1S/Zn/q+2PTFCDOFLOPIGGS-UHFFFAOYSA-Nzinc(2+) ion65.40963.9291465780zinc(2+) ion22FDB003729Zinc;Zinc ion;Dietary zinc;Zinc cation;Zinc, ion (zn2+);Zn(ii);Zn(2+);Zn2+PW_C001005Zinc13238411882711652915295751304468312029314770541011754251035434118545912055601325585133559813574491661178719812466226127242901332115176967225774011117758011477929336804001120020124120035406120060122120441409121257429123075137123827464125398299125413479125438297125685483126938388126953501126976205127180208209812-Keto-leukotriene B4HMDB000423412-Keto-leukotriene B4 is formed when leukotriene B4 (LTB4) is metabolized by beta-oxidation. LTB4 is the major metabolite in neutrophil polymorphonuclear leukocytes. Leukotrienes are metabolites of arachidonic acid derived from the action of 5-LO (5-lipoxygenase). The immediate product of 5-LO is LTA4 (leukotriene A4), which is enzymatically converted into either LTB4 (leukotriene B4) by LTA4 hydrolase or LTC4 (leukotriene C4) by LTC4 synthase. The regulation of leukotriene production occurs at various levels, including expression of 5-LO, translocation of 5-LO to the perinuclear region and phosphorylation to either enhance or inhibit the activity of 5-LO. Biologically active LTB4 is metabolized by w-oxidation carried out by specific cytochrome P450s (CYP4F) followed by beta-oxidation from the w-carboxy position and after CoA ester formation. (PMID: 8632343, 9667737)Leukotrienes 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.136696-10-1C059495280876278144444399CCCCC\C=C/CC(=O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=OC20H30O4InChI=1S/C20H30O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h6-11,14-15,19,22H,2-5,12-13,16-17H2,1H3,(H,23,24)/b8-7+,9-6-,14-10+,15-11-/t19-/m1/s1SJVWVCVZWMJXOK-NOJHDUNKSA-N(5S,6Z,8E,10E,14Z)-5-hydroxy-12-oxoicosa-6,8,10,14-tetraenoic acid334.4498334.214409448-4.64212-oxo-LTB40-1FDB023341(5s,6z,8e,10e,14z)-5-hydroxy-12-oxoicosa-6,8,10,14-tetraenoate;(5s,6z,8e,10e,14z)-5-hydroxy-12-oxoicosa-6,8,10,14-tetraenoic acid;12-dehydro-leukotriene b4;12-keto-ltb4;12-oxo-ltb4;12-oxoleukotriene b4;5-hydroxy-12-oxo-delta5,8,11,14-eicosapolyenoate;5-hydroxy-12-oxo-delta5,8,11,14-eicosapolyenoic acid;5s-hydroxy-12-keto-6z,8e,10e,14z-eicosatetraenoate;5s-hydroxy-12-keto-6z,8e,10e,14z-eicosatetraenoic acid;(5s,6z,8e,10e,14z)-5-hydroxy-12-oxoeicosa-6,8,10,14-tetraenoic acid;12-keto-leukotriene b4;5(s)-hydroxy-12-oxo-6(z),8(e),10(e),14(z)-eicosatetraenoic acid;(5s,6z,8e,10e,14z)-5-hydroxy-12-oxoeicosa-6,8,10,14-tetraenoate;5(s)-hydroxy-12-oxo-6(z),8(e),10(e),14(z)-eicosatetraenoate;5-hydroxy-12-oxo-δ5,8,11,14-eicosapolyenoate;5-hydroxy-12-oxo-δ5,8,11,14-eicosapolyenoic acidPW_C002098KtLeuB41336107740233212106612312363144780GlutathioneHMDB0000125Glutathione is a compound synthesized from cysteine, perhaps the most important member of the body's toxic waste disposal team. Like cysteine, glutathione contains the crucial thiol (-SH) group that makes it an effective antioxidant. There are virtually no living organisms on this planet-animal or plant whose cells don't contain some glutathione. Scientists have speculated that glutathione was essential to the very development of life on earth. glutathione has many roles; in none does it act alone. It is a coenzyme in various enzymatic reactions. The most important of these are redox reactions, in which the thiol grouping on the cysteine portion of cell membranes protects against peroxidation; and conjugation reactions, in which glutathione (especially in the liver) binds with toxic chemicals in order to detoxify them. glutathione is also important in red and white blood cell formation and throughout the immune system. glutathione's clinical uses include the prevention of oxygen toxicity in hyperbaric oxygen therapy, treatment of lead and other heavy metal poisoning, lowering of the toxicity of chemotherapy and radiation in cancer treatments, and reversal of cataracts. (http://www.dcnutrition.com/AminoAcids/) glutathione participates in leukotriene synthesis and is a cofactor for the enzyme glutathione peroxidase. It is also important as a hydrophilic molecule that is added to lipophilic toxins and waste in the liver during biotransformation before they can become part of the bile. glutathione is also needed for the detoxification of methylglyoxal, a toxin produced as a by-product of metabolism. This detoxification reaction is carried out by the glyoxalase system. Glyoxalase I (EC 4.4.1.5) catalyzes the conversion of methylglyoxal and reduced glutathione to S-D-Lactoyl-glutathione. Glyoxalase II (EC 3.1.2.6) catalyzes the hydrolysis of S-D-Lactoyl-glutathione to glutathione and D-lactate. GSH is known as a substrate in both conjugation reactions and reduction reactions, catalyzed by glutathione S-transferase enzymes in cytosol, microsomes, and mitochondria. However, it is also capable of participating in non-enzymatic conjugation with some chemicals, as in the case of n-acetyl-p-benzoquinone imine (NAPQI), the reactive cytochrome P450-reactive metabolite formed by acetaminophen, that becomes toxic when GSH is depleted by an overdose (of acetaminophen). glutathione in this capacity binds to NAPQI as a suicide substrate and in the process detoxifies it, taking the place of cellular protein thiol groups which would otherwise be covalently modified; when all GSH has been spent, NAPQI begins to react with the cellular proteins, killing the cells in the process. The preferred treatment for an overdose of this painkiller is the administration (usually in atomized form) of N-acetylcysteine, which is used by cells to replace spent GSSG and renew the usable GSH pool. (http://en.wikipedia.org/wiki/glutathione).70-18-8C0005112488616856OXIDIZED-GLUTATHIONE111188DB00143N[C@@H](CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O)C(O)=OC10H17N3O6SInChI=1S/C10H17N3O6S/c11-5(10(18)19)1-2-7(14)13-6(4-20)9(17)12-3-8(15)16/h5-6,20H,1-4,11H2,(H,12,17)(H,13,14)(H,15,16)(H,18,19)/t5-,6-/m0/s1RWSXRVCMGQZWBV-WDSKDSINSA-N(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-sulfanylethyl]carbamoyl}butanoic acid307.323307.083805981-2.546glutathione0-1DBMET00487FDB0014985-l-glutamyl-l-cysteinylglycine;Agifutol s;Bakezyme rx;Copren;Deltathione;Gsh;Glutathion;Glutathione;Glutathione red;Glutathione reduced;Glutathione-sh;Glutatiol;Glutatione;Glutide;Glutinal;Isethion;L-glutamyl-l-cysteinylglycine;L-glutathione;L-glutathione reduce;L-g-glutamyl-l-cysteinyl-glycine;L-gamma-glutamyl-l-cysteinyl-glycine;L-gamma-glutamyl-l-cysteinylglycine;Ledac;Neuthion;Red. glutathione;Reduced glutathione;Tathion;Tathione;Triptide;Gamma-glutamylcysteinylglycine;Gamma-l-glutamyl-l-cysteinyl-glycine;Gamma-l-glutamyl-l-cysteinylglycine;N-(n-gamma-l-glutamyl-l-cysteinyl)glycine;G-l-glutamyl-l-cysteinyl-glycine;γ-l-glutamyl-l-cysteinyl-glycine;N-(n-g-l-glutamyl-l-cysteinyl)glycine;N-(n-γ-l-glutamyl-l-cysteinyl)glycinePW_C000080GSH161141998614213371013624948893151939758391438426151774033327740811177424331780151157876113280709135120098405120187122120880124121067123121093383122838376123456118123632447123658398125467478125544297125856299127004209127077205933Leukotriene C4HMDB0001198Leukotriene C4 (LTC4) is a cysteinyl leukotriene (CysLT), a family of potent inflammatory mediators. Eosinophils, one of the principal cell types recruited to and activated at sites of allergic inflammation, is capable of elaborating lipid mediators, including leukotrienes derived from the oxidative metabolism of arachidonic acid (AA). Potentially 'activated' eosinophils may elaborate greater quantities of LTC4, than normal eosinophils. These activated eosinophils thus are 'primed' for enhanced LTC4 generation in response to subsequent stimuli. Some recognized priming stimuli are chemoattractants (e.g., eotaxin, PAF) that may participate in the recruitment of eosinophils to sites of allergic inflammation. The mechanisms by which chemoattractants and other activating cytokines (e.g., interleukin (IL)-5) or extracellular matrix components (e.g., fibronectin) enhance eosinophil eicosanoid formation are pertinent to the functions of these eicosanoids as paracrine mediators of allergic inflammation. Some eosinophil-derived eicosanoids may be active in down-regulating inflammation. It is increasingly likely that eicosanoids synthesized within cells, including eosinophils, may have intracellular (e.g., intracrine) roles in regulating cell functions, in addition to the more recognized activities of eicosanoids as paracrine mediators of inflammation. Acting extracellularly, the cysteinyl leukotrienes (CysLTs) LTC4 and its extracellular derivatives, LTD4 and LTE4 are key paracrine mediators pertinent to asthma and allergic diseases. Based on their receptor-mediated capabilities, they can elicit bronchoconstriction, mucous hypersecretion, bronchial hyperresponsiveness, increased microvascular permeability, and additional eosinophil infiltration. Eosinophils are a major source of CysLTs and have been identified as the principal LTC4 synthase expressing cells in bronchial mucosal biopsies of asthmatic subjects. (PMID: 12895596)Leukotrienes 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.72025-60-6C02166528049316978LEUKOTRIENE-C44444133CCCCC\C=C/C\C=C/C=C/C=C/[C@@H](SC[C@H](NC(=O)CC[C@H](N)C(O)=O)C(=O)NCC(O)=O)[C@@H](O)CCCC(O)=OC30H47N3O9SInChI=1S/C30H47N3O9S/c1-2-3-4-5-6-7-8-9-10-11-12-13-16-25(24(34)15-14-17-27(36)37)43-21-23(29(40)32-20-28(38)39)33-26(35)19-18-22(31)30(41)42/h6-7,9-13,16,22-25,34H,2-5,8,14-15,17-21,31H2,1H3,(H,32,40)(H,33,35)(H,36,37)(H,38,39)(H,41,42)/b7-6-,10-9-,12-11+,16-13+/t22-,23-,24-,25+/m0/s1GWNVDXQDILPJIG-NXOLIXFESA-N(5S,6R,7E,9E,11Z,14Z)-6-{[(2R)-2-[(4S)-4-amino-4-carboxybutanamido]-2-[(carboxymethyl)carbamoyl]ethyl]sulfanyl}-5-hydroxyicosa-7,9,11,14-tetraenoic acid625.774625.303300807-5.397leukotriene C40-2FDB022484(r-(r*,s*-(e,e,z,z)))-n-(s-(1-(4-carboxy-1-hydroxybutyl)-2,4,6,9-pentadecatetraenyl)-n-l-gamma-glutamyl-l-cysteinyl)-glycine;5s,6r-ltc;5s-hydroxy,6r-(s-glutathionyl),7e,9e,11z,14z-eicosatetraenoate;5s-hydroxy,6r-(s-glutathionyl),7e,9e,11z,14z-eicosatetraenoic acid;L-gamma-glutamyl-s-[(1r,2e,4e,6z,9z)-1-[(1s)-4-carboxy-1-hydroxybutyl]-2,4,6,9-pentadecatetraenyl]-l-cysteinyl-glycine;Ltc;Ltc4;Leucotriene c4;Leukotriene c;Leukotriene c1;Leukotriene c4;[r-[r*,s*-(e,e,z,z)]]-n-[s-[1-(4-carboxy-1-hydroxybutyl)-2,4,6,9-pentadecatetraenyl]-n-l-gamma-glutamyl-l-cysteinyl]-glycine 5s,6r-ltc4;(r-(r*,s*-(e,e,z,z)))-n-(s-(1-(4-carboxy-1-hydroxybutyl)-2,4,6,9-pentadecatetraenyl)-n-l-gamma-glutamyl-l-cysteinyl)glycine;5s,6r-ltc(sub 4);Ltc (sub 4);(r-(r*,s*-(e,e,z,z)))-n-(s-(1-(4-carboxy-1-hydroxybutyl)-2,4,6,9-pentadecatetraenyl)-n-l-g-glutamyl-l-cysteinyl)glycine;(r-(r*,s*-(e,e,z,z)))-n-(s-(1-(4-carboxy-1-hydroxybutyl)-2,4,6,9-pentadecatetraenyl)-n-l-γ-glutamyl-l-cysteinyl)glycinePW_C000933LTC413381042482774043321210681231236334471775Leukotriene D4HMDB0003080Leukotriene D4 (LTD4) is a cysteinyl leukotriene. Cysteinyl leukotrienes (CysLTs) are a family of potent inflammatory mediators that appear to contribute to the pathophysiologic features of allergic rhinitis. LTD4 is a pro-inflammatory mediator known to mediate its effects through specific cell-surface receptors belonging to the G-protein-coupled receptor family, namely the high-affinity CysLT1 (cysteinyl leukotriene 1) receptor. LTD4 is present at high levels in many inflammatory conditions, and areas of chronic inflammation have an increased risk for subsequent cancer development. LTD4 is associated with the pathogenesis of several inflammatory disorders, such as asthma and inflammatory bowel disease. Exposure to LTD4 increases survival and proliferation in intestinal epithelial cells. CysLT1 regulator is up-regulated in colon cancer tissue and LTD4 signalling facilitates the survival of cancer cells. LTD4 could reduce apoptosis in non-transformed epithelial cells. LTD4 causes up-regulation of beta-catenin through the CysLT1 receptor, PI3K (phosphoinositide 3-kinase), and GSK-3β (glycogen synthase kinase 3β). LTD4 induces beta-catenin translocation to the nucleus and activation of TCF/LEF family of transcription factors. LTD4 causes accumulation of free beta-catenin in non-transformed intestinal epithelial cells through the CysLT1 receptor, and this accumulation is dependent upon the activation of PI3K as well as GSK-3β inactivation (PMID: 16042577, 12607939). Leukotrienes 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 and are 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.73836-78-9C059515280878286664444401CCCCC\C=C/C\C=C/C=C/C=C/[C@@H](SC[C@H](N)C(=O)NCC(O)=O)[C@@H](O)CCCC(O)=OC25H40N2O6SInChI=1S/C25H40N2O6S/c1-2-3-4-5-6-7-8-9-10-11-12-13-16-22(21(28)15-14-17-23(29)30)34-19-20(26)25(33)27-18-24(31)32/h6-7,9-13,16,20-22,28H,2-5,8,14-15,17-19,26H2,1H3,(H,27,33)(H,29,30)(H,31,32)/b7-6-,10-9-,12-11+,16-13+/t20-,21-,22+/m0/s1YEESKJGWJFYOOK-IJHYULJSSA-N(5S,6R,7E,9E,11Z,14Z)-6-{[(2R)-2-amino-2-[(carboxymethyl)carbamoyl]ethyl]sulfanyl}-5-hydroxyicosa-7,9,11,14-tetraenoic acid496.66496.26070819-5.285leukotriene D40-1FDB023105(R-(R*,s*-(e,e,Z,Z)))-N-(S-(1-(4-carboxy-1-hydroxybutyl)-2,4,6,9-pentadecatetraenyl)-L-cysteinyl)glycine;LTD4;Leukotriene D;Leukotriene D4PW_C001775LTD413408424727740511112107012212363513595L-Glutamic acidHMDB0000148Glutamic acid (Glu), also referred to as glutamate (the anion), is one of the 20 proteinogenic amino acids. It is not among the essential amino acids. Glutamate is a key molecule in cellular metabolism. In humans, dietary proteins are broken down by digestion into amino acids, which serves as metabolic fuel or other functional roles in the body. Glutamate is the most abundant fast excitatory neurotransmitter in the mammalian nervous system. At chemical synapses, glutamate is stored in vesicles. Nerve impulses trigger release of glutamate from the pre-synaptic cell. In the opposing post-synaptic cell, glutamate receptors, such as the NMDA receptor, bind glutamate and are activated. Because of its role in synaptic plasticity, it is believed that glutamic acid is involved in cognitive functions like learning and memory in the brain. Glutamate transporters are found in neuronal and glial membranes. They rapidly remove glutamate from the extracellular space. In brain injury or disease, they can work in reverse and excess glutamate can accumulate outside cells. This process causes calcium ions to enter cells via NMDA receptor channels, leading to neuronal damage and eventual cell death, and is called excitotoxicity. The mechanisms of cell death include: * Damage to mitochondria from excessively high intracellular Ca2+. * Glu/Ca2+-mediated promotion of transcription factors for pro-apoptotic genes, or downregulation of transcription factors for anti-apoptotic genes. Excitotoxicity due to glutamate occurs as part of the ischemic cascade and is associated with stroke and diseases like amyotrophic lateral sclerosis, lathyrism, and Alzheimer's disease. glutamic acid has been implicated in epileptic seizures. Microinjection of glutamic acid into neurons produces spontaneous depolarization around one second apart, and this firing pattern is similar to what is known as paroxysmal depolarizing shift in epileptic attacks. This change in the resting membrane potential at seizure foci could cause spontaneous opening of voltage activated calcium channels, leading to glutamic acid release and further depolarization. (http://en.wikipedia.org/wiki/Glutamic_acid).56-86-0C000253303216015GLT30572DB00142N[C@@H](CCC(O)=O)C(O)=OC5H9NO4InChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m0/s1WHUUTDBJXJRKMK-VKHMYHEASA-N(2S)-2-aminopentanedioic acid147.1293147.053157781-0.263L-glutamic acid0-1FDB012535(2s)-2-aminopentanedioate;(2s)-2-aminopentanedioic acid;(s)-(+)-glutamate;(s)-(+)-glutamic acid;(s)-2-aminopentanedioate;(s)-2-aminopentanedioic acid;(s)-glutamate;(s)-glutamic acid;1-amino-propane-1,3-dicarboxylate;1-amino-propane-1,3-dicarboxylic acid;1-aminopropane-1,3-dicarboxylate;1-aminopropane-1,3-dicarboxylic acid;2-aminoglutarate;2-aminoglutaric acid;2-aminopentanedioate;2-aminopentanedioic acid;Aciglut;Aminoglutarate;Aminoglutaric acid;E;Glt;Glu;Glusate;Glut;Glutacid;Glutamicol;Glutamidex;Glutaminate;Glutaminic acid;Glutaminol;Glutaton;L-(+)-glutamate;L-(+)-glutamic acid;L-glu;L-glutamate;L-glutaminate;L-glutaminic acid;L-a-aminoglutarate;L-a-aminoglutaric acid;L-alpha-aminoglutarate;L-alpha-aminoglutaric acid;A-aminoglutarate;A-aminoglutaric acid;A-glutamate;A-glutamic acid;Alpha-aminoglutarate;Alpha-aminoglutaric acid;Alpha-glutamate;Alpha-glutamic acid;Acide glutamique;Acido glutamico;Acidum glutamicum;Glutamate;Glutamic acid;L-glutaminsaeurePW_C000095Glu1624436581191138416414969911054214485014562614625453231115344113541511754391185565132563110756321085859105600614760711576191946531856838187684418870927270937171652057182207751422475181518208225837322011792198118551611200422212621311268328912697290423483154234931842845320770202537733213377525112779713467797732777981347782913458064913512002312412004012212008640712034740612069212612081641812114742312115342412115742512283311912299712012329944312340145412371945812372545912372946012540129912541829712545748112566747912576930112580248912694138812699520612716250112725750614073884140739597404505,6-EpoxytetraeneHMDB00611115,6-Ep-15S-hete, also known as 5,6-epoxytetraene, belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms. Thus, 5,6-ep-15S-hete is considered to be an eicosanoid lipid molecule. 5,6-Ep-15S-hete is considered to be a practically insoluble (in water) and relatively neutral molecule.C14815119540606409510128355CCCCC[C@H](O)\C=C\C=C/C=C/C=C/[C@@H]1O[C@H]1CCCC(O)=OC20H30O4InChI=1S/C20H30O4/c1-2-3-8-12-17(21)13-9-6-4-5-7-10-14-18-19(24-18)15-11-16-20(22)23/h4-7,9-10,13-14,17-19,21H,2-3,8,11-12,15-16H2,1H3,(H,22,23)/b6-4-,7-5+,13-9+,14-10+/t17-,18-,19-/m0/s1YNHSGCYEQVDEOY-UZDWIPAXSA-N4-[(2S,3S)-3-[(1E,3E,5Z,7E,9S)-9-hydroxytetradeca-1,3,5,7-tetraen-1-yl]oxiran-2-yl]butanoic acid334.4498334.214409448-4.5025,6-epoxytetraene0-1(7e,9e,11z,13e)-(5s,6s,15s)-5,6-epoxy-15-hydroxyeicosa-7,9,11,13-tetraenoic acid;(7e,9e,11z,13e)-(5s,6s,15s)-5,6-epoxy-15-hydroxyicosa-7,9,11,13-tetraenoic acid;5s,6s-epoxy-15s-hydroxy-7e,9e,11z,13e-eicosatetraenoic acid;(7e,9e,11z,13e)-(5s,6s,15s)-5,6-epoxy-15-hydroxyeicosa-7,9,11,13-tetraenoate;(7e,9e,11z,13e)-(5s,6s,15s)-5,6-epoxy-15-hydroxyicosa-7,9,11,13-tetraenoate;5s,6s-epoxy-15s-hydroxy-7e,9e,11z,13e-eicosatetraenoatePW_C04045056Ept13411877406130121072125123637136210615(S)-HPETEHMDB000424415(S)-hydroperoxyeicosatetraenoic acid (15(S)-HPETE) is the corresponding hydroperoxide of 15(S)-HETE and undergoes homolytic decomposition to the DNA-reactive bifunctional electrophile 4-oxo-2(E)-nonenal, a precursor of heptanone-etheno-2'-deoxyguanosine. Reactive oxygen species convert the omega-6 polyunsaturated fatty acid arachidonic acid into (15-HPETE); vitamin C mediates 15(S)-HPETE decomposition. 15(S)-HPETE initiates apoptosis in vascular smooth muscle cells. 15(S)-HPETE is a lipoxygenase metabolite that affects the expression of cell adhesion molecules (CAMs) involved in the adhesion of leukocytes and/or the accumulation of leukocytes in the vascular endothelium, these being the initial events in endothelial cell injury. 15(S)-HPETE induces a loss of cardiomyocytes membrane integrity. 15-(S)HPETE is a hydroperoxide that enhances the activity of the enzymes lipoxygenase [EC 1.13.11.12] and Na+, K+-ATPase [EC 3.6.3.9] of brain microvessels. Lipoxygenase(s) and Na+-K+-ATPase of brain microvessels may play a significant role in the occurrence of ischemic brain edema. (PMID: 15964853, 15723435, 8655602, 8595608, 2662983).70981-96-3C059665280893156284444416CCCCC[C@H](OO)\C=C\C=C/C\C=C/C\C=C/CCCC(O)=OC20H32O4InChI=1S/C20H32O4/c1-2-3-13-16-19(24-23)17-14-11-9-7-5-4-6-8-10-12-15-18-20(21)22/h4-5,8-11,14,17,19,23H,2-3,6-7,12-13,15-16,18H2,1H3,(H,21,22)/b5-4-,10-8-,11-9-,17-14+/t19-/m0/s1BFWYTORDSFIVKP-VAEKSGALSA-N(5Z,8Z,11Z,13E,15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoic acid336.4657336.230059512-5.27215(S)-hpete0-1FDB023349(5z,8z,11z,13e)-(15s)-15-hydroperoxyicosa-5,8,11,13-tetraenoate;(5z,8z,11z,13e)-(15s)-15-hydroperoxyicosa-5,8,11,13-tetraenoic acid;15-hydroperoxyeicosatetraenoate;15-hydroperoxyeicosatetraenoic acid;15-hydroperoxyicosatetraenoate;15-hydroperoxyicosatetraenoic acid;15s-hydroperoxyeicosatetraenoate;15s-hydroperoxyeicosatetraenoic acid;15s-hpete;(5z,8z,11z,13e,15s)-15-hydroperoxyicosa-5,8,11,13-tetraenoatePW_C00210615SHPET13421877407130121073125123638136198615(S)-HETEHMDB000387615(S)-HETE is a hydroxyeicosatetraenoic acid. Hydroxyeicosatetraenoic acids (HETEs) are formed by the 5-, 12- and 15-lipoxygenase (LO) pathways. 5- and 12-LO products are mainly proinflammatory in the skin whereas the main 15-LO product 15-HETE has antiinflammatory capacities. In vitro 15-HETE has been shown to inhibit LTB4 formation, 12-HETE formation and specifically inhibits the neutrophil chemotactic effect of LTB4. The inhibition of LTB4 formation is probably due to modulation of the 5-LO because no changes in PGE2 formation have been determined. In vivo, 15-HETE inhibits LTB4-induced erythema and edema, and reduces LTB4 in the synovial fluid of carragheenan-induced experimental arthritis in dogs. 15-HETE has also some immunomodulatory effects. It inhibits the mixed lymphocyte reaction, induces generation of murine cytotoxic suppressor T cells, and it decreases interferon production by murine lymphoma cells. Furthermore, IL-4 and IL-13 have recently been shown to be potent activators of the 15-LO in mononuclear cells. (PMID: 11104340).54845-95-3C047425280724155584444307CCCCC[C@H](O)\C=C\C=C/C\C=C/C\C=C/CCCC(O)=OC20H32O3InChI=1S/C20H32O3/c1-2-3-13-16-19(21)17-14-11-9-7-5-4-6-8-10-12-15-18-20(22)23/h4-5,8-11,14,17,19,21H,2-3,6-7,12-13,15-16,18H2,1H3,(H,22,23)/b5-4-,10-8-,11-9-,17-14+/t19-/m0/s1JSFATNQSLKRBCI-VAEKSGALSA-N(5Z,8Z,11Z,13E,15S)-15-hydroxyicosa-5,8,11,13-tetraenoic acid320.4663320.23514489-5.22215 hete0-1FDB023242(15s)-15-hydroxy-5,8,11-cis-13-trans-eicosatetraenoate;(15s)-15-hydroxy-5,8,11-cis-13-trans-eicosatetraenoic acid;(15s)-15-hydroxy-5,8,11-cis-13-trans-eicosic acid;(15s)-15-hydroxy-5,8,11-cis-13-trans-icosatetraenoate;(15s)-15-hydroxy-5,8,11-cis-13-trans-icosatetraenoic acid;(15s,5z,8z,11z,13e)-15-hydroxyeicosatetraenoate;(15s,5z,8z,11z,13e)-15-hydroxyeicosatetraenoic acid;(5z,8z,11z,13e)-(15s)-15-hydroxyicosa-5,8,11,13-tetraenoate;(5z,8z,11z,13e)-(15s)-15-hydroxyicosa-5,8,11,13-tetraenoic acid;(s)-15-hete;15 hete;15(s)-hydroxy-(5z,8z,11z,13e)-eicosatetraenoate;15(s)-hydroxy-(5z,8z,11z,13e)-eicosatetraenoic acid;15-hete;15s-hete;15s-hydroxy-5z,8z,11z,13e-eicosatetraenoate;15s-hydroxy-5z,8z,11z,13e-eicosatetraenoic acid;(15s)-hydroxy-(5z,8z,11z,13e)-eicosatetraenoic acid;(15s)-hydroxyeicosa-(5z,8z,11z,13e)-tetraenoic acid;(5z,8z,11z,13e,15s)-15-hydroxy-5,8,11,13-eicosatetraenoic acid;(5z,8z,11z,13e,15s)-15-hydroxyeicosa-5,8,11,13-tetraenoic acid;15(s)-hydroxyeicosatetraenoic acid;Icomucret;(5z,8z,11z,13e,15s)-15-hydroxyicosa-5,8,11,13-tetraenoate;(15s)-hydroxy-(5z,8z,11z,13e)-eicosatetraenoate;(15s)-hydroxyeicosa-(5z,8z,11z,13e)-tetraenoate;(5z,8z,11z,13e,15s)-15-hydroxy-5,8,11,13-eicosatetraenoate;(5z,8z,11z,13e,15s)-15-hydroxyeicosa-5,8,11,13-tetraenoate;15(s)-hydroxyeicosatetraenoatePW_C00198615SHETE13438137449774091111210741221236391351847Oxidized glutathioneHMDB0003337Oxidized glutathione is a glutathione dimer formed by a disulfide bond between the cysteine sulfhydryl side chains during the course of being oxidized. glutathione participates in leukotriene synthesis and is a cofactor for the enzyme glutathione peroxidase. It is also important as a hydrophilic molecule that is added to lipophilic toxins and waste in the liver during biotransformation before they can become part of the bile. glutathione is also needed for the detoxification of methylglyoxal, a toxin produced as a by-product of metabolism. This detoxification reaction is carried out by the glyoxalase system. Glyoxalase I (EC 4.4.1.5) catalyzes the conversion of methylglyoxal and reduced glutathione to S-D-Lactoyl-glutathione. Glyoxalase II (EC 3.1.2.6) catalyzes the hydrolysis of S-D-Lactoyl-glutathione to glutathione and D-lactate.27025-41-8C00127525579617858OXIDIZED-GLUTATHIONE950NC(CCC(=O)NC(CSSCC(NC(=O)CCC(N)C(O)=O)C(=O)NCC(O)=O)C(=O)NCC(O)=O)C(O)=OC20H32N6O12S2InChI=1S/C20H32N6O12S2/c21-9(19(35)36)1-3-13(27)25-11(17(33)23-5-15(29)30)7-39-40-8-12(18(34)24-6-16(31)32)26-14(28)4-2-10(22)20(37)38/h9-12H,1-8,21-22H2,(H,23,33)(H,24,34)(H,25,27)(H,26,28)(H,29,30)(H,31,32)(H,35,36)(H,37,38)YPZRWBKMTBYPTK-UHFFFAOYSA-N2-amino-4-[(2-{[2-(4-amino-4-carboxybutanamido)-2-[(carboxymethyl)carbamoyl]ethyl]disulfanyl}-1-[(carboxymethyl)carbamoyl]ethyl)carbamoyl]butanoic acid612.631612.151961898-3.1810oxiglutatione0-2FDB023147Gssg;Glutathione disulfide;L(-)-glutathione(oxidized);Oxiglutatione;(2s)-2-azaniumyl-4-{[(1r)-2-{[(2r)-2-[(4s)-4-azaniumyl-4-carboxylatobutanamido]-2-[(carboxylatomethyl)carbamoyl]ethyl]disulfanyl}-1-[(carboxylatomethyl)carbamoyl]ethyl]carbamoyl}butanoatePW_C001847GSSG1848487837741011178012112807111191201031221201884071228401351254702971255454811270072051270782062100δ-12-Prostaglandin J2HMDB0004238Delta-12-Prostaglandin J2 (d12-PGJ2) is the ultimate metabolite of Prostaglandin D2 (PGD2). PGD2 is an unstable molecule and undergoes dehydration to form PGJ2 in aqueous solution, and is then converted to d12-PGJ2, in the presence of serum albumin or plasma. d12-PGJ2 forms a conjugate with the thiol of glutathione (GSH) and GSH suppresses the d12-PGJ2-induced HSP synthesis and subsequent inhibition of cell growth (HSPs are a set of proteins synthesized in response to heat shock or to other environmental stresses). d12-PGJ2 has been shown to stimulate alkaline phosphatase activity and calcification of human osteoblastic cells, the potency of the PGs being comparable to that of 1-a,25-dihydroxy vitamin D. d12-PGJ2 enhances the type-1 collagen synthesis in human osteoblasts during calcification. Thus, d12-PGJ2 modulates osteogenesis through induction of the syntheses of multiple proteins related to mineralization. Considering that PGD2 is a major arachidonate metabolite in bone marrow, d12-PGJ2, may be physiologically involved in the modulation of osteogenesis. d12-PGJ2 induces heme oxygenase, HO-l. Heme oxygenase is a key enzyme in heme catabolism, oxidatively clearing heme to yield biliverdin, iron and carbon monoxide. The biological function of this enzyme is the conversion of potentially toxic heme to bile and the recovery of the iron. Furthermore, carbon monoxide produced on the enzymatic degradation of heme has been suggested to function as a neural messenger. Two isozymes of heme oxygenase, HO-l and HO-2, have been identified. HO-2 is constitutively expressed, while HO-l is drastically induced in response to a variety of stresses, including heavy metals, heat shock and UV irradiation. (PMID: 8777585)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.87893-54-7C059585280885281304444408CCCCC[C@H](O)C\C=C1/[C@@H](C\C=C/CCCC(O)=O)C=CC1=OC20H30O4InChI=1S/C20H30O4/c1-2-3-6-10-17(21)13-14-18-16(12-15-19(18)22)9-7-4-5-8-11-20(23)24/h4,7,12,14-17,21H,2-3,5-6,8-11,13H2,1H3,(H,23,24)/b7-4-,18-14+/t16-,17-/m0/s1TUXFWOHFPFBNEJ-GJGHEGAFSA-N(5Z)-7-[(1S,5E)-5-[(3S)-3-hydroxyoctylidene]-4-oxocyclopent-2-en-1-yl]hept-5-enoic acid334.4498334.214409448-4.192delta-12-prostaglandin J20-1FDB023343Prostaglandin j2;Delta-12-pgj2;Delta-12-prostaglandin j2;9-deoxy-9,10-didehydro-12,13-didehydro-13,14-dihydroprostaglandin d2;9-deoxy-delta(9), delta(12)-13,14-dihydroprostaglandin d2;9-deoxy-delta(9,12)-13,14-dihydro pgd2;Dddd-pgd2;Delta(12)-pgj2PW_C00210012-PGln13441877411130121075125123640136239815-Deoxy-d-12,14-PGJ2HMDB000507915-deoxy-PGJ2 (15d-PGJ2) is a metabolite of the PGJ2 prostanoid family that influences multiple signaling pathways by covalently binding with key signaling molecules. Among them, 15d-PGJ2 has displayed highest potency as an inducer of gene expression. Prostanoids are a subclass of the lipid mediator group known as eicosanoids. They derive from C-20 polyunsaturated fatty acids, mainly dihomo-gamma-linoleic (20:3n-6), arachidonic (20:4n-6), and eicosapentaenoic (20:5n-3) acids, through the action of cyclooxygenases-1 and -2 (COX-1 and COX-2). The reaction product of COX is the unstable endoperoxide prostaglandin H (PGH) that is further transformed into the individual prostanoids by a series of specific prostanoid synthases. Prostanoids are local-acting mediators formed and inactivated within the same or neighbouring cells prior to their release into circulation as inactive metabolites (15-keto- and 13,14-dihydroketo metabolites). Non-enzymatic peroxidation of arachidonic acid and other fatty acids in vivo can result in prostaglandin-like substances isomeric to the COX-derived prostaglandins that are termed isoprostanes. Prostanoids take part in many physiological and pathophysiological processes in practically every organ, tissue and cell, including the vascular, renal, gastrointestinal and reproductive systems. Their activities are mediated through prostanoid-specific receptors and intracellular signalling pathways, whilst their biosynthesis and action are blocked by nonsteroidal antiinflammatory drugs (NSAID). Isoprostanes are considered to be reliable markers of oxidant stress status and have been linked to inflammation, ischaemia-reperfusion, diabetes, cardiovascular disease, reproductive disorders and diabetes. (PMID: 16986207, 16857669). 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.87893-55-8C1471753112116077274470730CCCCC\C=C\C=C1/[C@@H](C\C=C/CCCC(O)=O)C=CC1=OC20H28O3InChI=1S/C20H28O3/c1-2-3-4-5-6-10-13-18-17(15-16-19(18)21)12-9-7-8-11-14-20(22)23/h6-7,9-10,13,15-17H,2-5,8,11-12,14H2,1H3,(H,22,23)/b9-7-,10-6+,18-13+/t17-/m0/s1VHRUMKCAEVRUBK-GODQJPCRSA-N(5Z)-7-[(1S,5E)-5-[(2E)-oct-2-en-1-ylidene]-4-oxocyclopent-2-en-1-yl]hept-5-enoic acid316.4345316.203844762-5.021delta12,14-PGJ20-1FDB023619(5z,12e,14e) 11-oxo prosta-5,9,12,14-tetraen-1-oate;(5z,12e,14e) 11-oxo prosta-5,9,12,14-tetraen-1-oic acid;(5z,12e,14e)-11-oxo-prosta-5,9,12,14-tetraen-1-oate;(5z,12e,14e)-11-oxo-prosta-5,9,12,14-tetraen-1-oic acid;11-oxo-5z,9,12,14-prostatetraenoate;11-oxo-5z,9,12,14-prostatetraenoic acid;15-deoxy-pgj2;15-deoxy-delta 12, 14-prostaglandin j2;15-deoxy-delta-12, 14 pgj-2;15-deoxy-delta-12,14-pgj2;15-deoxy-delta-12,14-prostaglandin j2;15-deoxy-delta12,14-pgj2;15-deoxy-delta12,14-prostaglandin;15-deoxy-prostaglandin j2;15d-pgj2;Delta12,14-pgj2;Delta-12,14-15-deoxy-pgj2;15-deoxy-δ-12,14-prostaglandin j2PW_C00239815DPGJ21345187741213012107612512364113617266-Keto-prostaglandin F1aHMDB00028866-keto-Prostaglandin F1a is the physiologically active and stable metabolite of prostacyclin. (A prostaglandin found in nearly all mammalian tissue that is a powerful vasodilator and inhibits platelet aggregation; it is biosynthesized enzymatically from prostaglandin endoperoxides in human vascular tissue; the sodium salt has been also used to treat primary pulmonary hypertension (Hypertension, Pulmonary). A delayed and prolonged increase in 6-keto-PGF1 alpha is reported in animals with septic shock, i.e., those with fecal peritonitis or cecal ligation. 6-keto-Prostaglandin F1a plasma levels has been found increased in patients with epidemic hemorrhagic fever, in patients with acute obstructive suppurative cholangitis, in patients with gynecologic cancer and has significant correlation with the level of high density lipoprotein cholesterol in plasma. (PMID 1976492, 2298410, 2379443, 2111556)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.58962-34-8C059615280888281584444411CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1CC(=O)CCCCC(O)=OC20H34O6InChI=1S/C20H34O6/c1-2-3-4-7-14(21)10-11-16-17(19(24)13-18(16)23)12-15(22)8-5-6-9-20(25)26/h10-11,14,16-19,21,23-24H,2-9,12-13H2,1H3,(H,25,26)/b11-10+/t14-,16+,17+,18+,19-/m0/s1KFGOFTHODYBSGM-ZUNNJUQCSA-N7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]-6-oxoheptanoic acid370.4804370.23553882-2.9146 keto PGF1 α0-1DBMET00557FDB0230776-keto-pgf1a;6-keto-pgf1alpha;6-keto-prostaglandin f1a;6-keto-prostaglandin f1alpha;6-ketoprostaglandin f1 alpha;6-ketoprostaglandin f1alpha;6-oxo-9s,11r,15s-trihydroxy-13e-prostenoate;6-oxo-9s,11r,15s-trihydroxy-13e-prostenoic acid;6-oxo-pgf1a;6-oxo-pgf1alpha;6-oxo-prostaglandin f1alpha;6-oxoprostaglandin f1a;6-oxoprostaglandin f1alpha;6-oxo-prostaglandin f1a;6-oxo-prostaglandin f1α;6-keto-pgf1α;6-keto-prostaglandin f1α;6-ketoprostaglandin f1a;6-ketoprostaglandin f1α;6-oxo-pgf1α;6-oxoprostaglandin f1αPW_C0017266KPgF1a1346187741313012107712512364213621036-Ketoprostaglandin E1HMDB00042416-Ketoprostaglandin E1 (6-keto PGE1) is a biologically active and stable prostacyclin (PGI2) metabolite and a substrate for Adenylate cyclase type III. 6-keto PGE1 is a potent coronary vasodilator. 6-keto PGE1 could be elevated in plasma of patients with primary thrombocythaemia. 6-keto-PGE1 has approximately four times less potent antiplatelet activity than PGI2 on a molar basis in man. The cardiovascular and plasma renin activity (PRA) changes are less prominent for 6-keto-PGE1 than PGI2. Salt loading slightly increases urinary 6-keto PGE1. 6-keto-PGE1 elicits the same biological effects as PGI2 in human platelets and in rabbit aorta and mesenteric artery, being, however, less potent. 6-keto-PGE1 dose-dependently stimulates adenylate cyclase activity in membranes of human platelets and cultured myocytes from rabbit aorta and mesenteric artery. The extent of stimulation of the enzyme by 6-keto-PGE1 is the same as elicited by PGI2, while the apparent affinity is lower than that of prostacyclin, both in platelets and in vascular smooth muscle cells. At the level of platelet membranes, 6-keto-PGE1 interacts with the binding sites labelled by PGI2. However, in platelets as well as in mesenteric artery myocytes, 6-keto-PGE1 interacts with only one class of sites as demonstrated either by binding or by adenylate cyclase studies, whereas PGI2 in the same conditions recognizes two different classes. (PMID: 3186779, 3075239, 3472253, 3912001, 3881881, 6391491)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.67786-53-2C059625280889282694444412CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CC(=O)CCCCC(O)=OC20H32O6InChI=1S/C20H32O6/c1-2-3-4-7-14(21)10-11-16-17(19(24)13-18(16)23)12-15(22)8-5-6-9-20(25)26/h10-11,14,16-18,21,23H,2-9,12-13H2,1H3,(H,25,26)/b11-10+/t14-,16+,17+,18+/m0/s1ROUDCKODIMKLNO-CTBSXBMHSA-N7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]-6-oxoheptanoic acid368.4645368.219888756-3.3236-Keto-PGE10-1FDB0233466,9-dioxo-11r,15s-dihydroxy-13e-prostenoate;6,9-dioxo-11r,15s-dihydroxy-13e-prostenoic acid;6-kpge1;6-keto pge1;6-keto-pge1;6-ketoprostaglandin e1;6-oxo-pge1;6-oxo-prostaglandin e1;6-oxoprostaglandin e1;6-keto-prostaglandin e1PW_C0021036-Kpge11347187741413012107812512364313667735-HETEHMDB00111345-hydroxyeicosatetraenoic acid (5-HETE) is an endogenous eicosanoid. 5-HETE is an intermediate in arachidonic acid metabolism. It is converted from 5(S)-HPETE via the enzyme glutathione peroxidase (EC 1.11.1.9)and then converted to 5-OxoETE. It is also involved in the pathway of leukotriene synthesis. In addition, it is a modulator of tubuloglomerular feedback.70608-72-9C048055280733282094444314CCCCC\C=C/C\C=C/C\C=C/C=C/[C@@H](O)CCCC(O)=OC20H32O3InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(21)17-15-18-20(22)23/h6-7,9-10,12-14,16,19,21H,2-5,8,11,15,17-18H2,1H3,(H,22,23)/b7-6-,10-9-,13-12-,16-14+/t19-/m1/s1KGIJOOYOSFUGPC-JGKLHWIESA-N(5S,6E,8Z,11Z,14Z)-5-hydroxyicosa-6,8,11,14-tetraenoic acid320.4663320.23514489-5.3225-hydroxyeicosatetraenoic acid0-1C048055(s)-hete;5(s)-hydroxy-6-trans-8,11,14-cis-eicosatetraenoate;5(s)-hydroxy-6-trans-8,11,14-cis-eicosatetraenoic acid;5(s)-hydroxyeicosatetraenoate;5(s)-hydroxyeicosatetraenoic acid;5-hete;5-hydroxy-6,8,11,14-eicosatetraenoate;5-hydroxy-6,8,11,14-eicosatetraenoic acid;5-hydroxyeicosatetraenoate;5-hydroxyeicosatetraenoic acid;5-l-hydroxy-6,8,11,14-eicosatetraenoate;5-l-hydroxy-6,8,11,14-eicosatetraenoic acid;5s-hydroxy-6,8,11,14-eicosatetraenoate;5s-hydroxy-6,8,11,14-eicosatetraenoic acid;(5s,6e,8z,11z,14z)-5-hydroxyeicosa-6,8,11,14-tetraenoic acid;(6e,8z,11z,14z)-(5s)-5-hydroxyicosa-6,8,11,14-tetraenoic acid;(s)-(e,z,z,z)-5-hydroxyeicosa-6,8,11,14-tetraenoic acid;5(s)-hydroxy-6(e),8(z),11(z),14(z)-eicosatetraenoic acid;5s-hete;(5s,6e,8z,11z,14z)-5-hydroxyeicosa-6,8,11,14-tetraenoate;(6e,8z,11z,14z)-(5s)-5-hydroxyicosa-6,8,11,14-tetraenoate;(s)-(e,z,z,z)-5-hydroxyeicosa-6,8,11,14-tetraenoate;5(s)-hydroxy-6(e),8(z),11(z),14(z)-eicosatetraenoatePW_C0067735-HETE1348187741513012107912512364413662295-KETEHMDB00102175-oxo-6E,8Z,11Z,14Z-eicosatetraenoic acid (5-oxo-ETE), 5-lipoxygenase product is a potent chemoattractant for neutrophils and eosinophils. Its actions are mediated by the oxoeicosanoid (OXE) receptor, a member of the G protein-coupled receptor family.(PMID:18292294).126432-17-5C147325283159524494446283CCCCC\C=C/C\C=C/C\C=C/C=C/C(=O)CCCC(O)=OC20H30O3InChI=1S/C20H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(21)17-15-18-20(22)23/h6-7,9-10,12-14,16H,2-5,8,11,15,17-18H2,1H3,(H,22,23)/b7-6-,10-9-,13-12-,16-14+MEASLHGILYBXFO-XTDASVJISA-N(6E,8Z,11Z,14Z)-5-oxoicosa-6,8,11,14-tetraenoic acid318.4504318.219494826-5.7115-Oxo-ETE0-1C147325-keto-6,8,11,14-eicosatetraenoate;5-keto-6,8,11,14-eicosatetraenoic acid;5-oxo-6,8,11,14-eicosatetraenoate;5-oxo-6,8,11,14-eicosatetraenoic acid;5-oxo-eicosatetraenoate;5-oxo-eicosatetraenoic acid;5-oxoete;(6e,8z,11z,14z)-5-oxoicosa-6,8,11,14-tetraenoic acid;5-keto-ete;5-ketoeicosatetraenoic acid;5-oxo, 6t,8c,11c,14c-20:4;5-oxo-6(e),8(z),11(z),14(z)-eicosatetraenoic acid;5-oxo-6e,8z,11z,14z-eicosatetraenoic acid;5-oxo-icosa-6,8,11,14-tetraenoic acid;5-oxoeicosatetraenoic acid;5-oxoicosatetraenoic acid;Eicosa-5,8,12,14-tetraenoic acid;(6e,8z,11z,14z)-5-oxoicosa-6,8,11,14-tetraenoate;5-ketoeicosatetraenoate;5-oxo-6(e),8(z),11(z),14(z)-eicosatetraenoate;5-oxo-6e,8z,11z,14z-eicosatetraenoate;5-oxo-icosa-6,8,11,14-tetraenoate;5-oxoeicosatetraenoate;5-oxoicosatetraenoate;Eicosa-5,8,12,14-tetraenoatePW_C0062295-KETE134918774161301210801251236451361687Prostaglandin J2HMDB0002710Prostaglandin J2 (PGJ2) is an endogenous product of inflammation in humans. It induces neuronal death and the accumulation of ubiquitinated proteins into distinct aggregates. It may play a role in neurodegenerative disorders inducing a chain of events that culminates in neuronal cell death. An altered expression of enzymes in PGJ2 synthesis may represent a novel pathogenic mechanism in human obesity. The peroxisome proliferator-activated receptor gamma (PPARγ) has a fundamental role in glucose homeostasis and adipocyte differentiation. Besides linoleate, linolenate and arachidonate, the most notable PPAR ligand is 15-deoxy-delta12-14-prostaglandin J2, a natural derivative of prostaglandin D2 and PGJ2. It is therefore plausible that the production of 15d-PGJ2 within adipose tissue may act as an endogenous mediator of adipocyte differentiation. PGJ2 disrupts the cytoskeleton in neuronal cells. This cyclopentenone prostaglandin triggered endoplasmic reticulum (ER) collapse and the redistribution of ER proteins, such as calnexin and catechol-O-methyltransferase, into a large centrosomal aggregate containing ubiquitinated proteins and alpha-synuclein. The PGJ2-dependent cytoskeletal rearrangement paralleled the development of the large centrosomal aggregate. Supporting a mechanism by which, upon PGJ2 treatment, cytoskeleton/ER collapse coincides with the relocation of ER proteins, other potentially neighboring proteins, and ubiquitinated proteins into centrosomal aggregates. Development of these large perinuclear aggregates is associated with disruption of the microtubule/ER network. This aberrant protein deposition, triggered by a product of inflammation, may be common to other compounds that disrupt microtubules and induce protein aggregation, such as MPP+ and rotenone, found to be associated with neurodegeneration. Many neurodegenerative disorders, such as Parkinson disease, exhibit inclusion bodies containing ubiquitinated proteins. Concentrations of PGJ2 in biofluids have not been established, since this prostaglandin is further metabolized into delta12-PGJ2, and 15-deoxy-delta12,14-PGJ2. (PMID: 16737963, 16842938, 16774923)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.60203-57-8C059575280884274854444407CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)C=CC1=OC20H30O4InChI=1S/C20H30O4/c1-2-3-6-10-17(21)13-14-18-16(12-15-19(18)22)9-7-4-5-8-11-20(23)24/h4,7,12-18,21H,2-3,5-6,8-11H2,1H3,(H,23,24)/b7-4-,14-13+/t16-,17-,18+/m0/s1UQOQENZZLBSFKO-POPPZSFYSA-N(5Z)-7-[(1S,5R)-5-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-4-oxocyclopent-2-en-1-yl]hept-5-enoic acid334.4498334.214409448-4.232prostaglandin J20-1FDB02304911-oxo-15s-hydroxy-5z,8z,13e-prostatrienoate;11-oxo-15s-hydroxy-5z,8z,13e-prostatrienoic acid;9-deoxy-delta-9-pgd2;9-deoxy-delta-9-prostaglandin d2;Pgj2;9-deoxy-δ-9-pgd2;9-deoxy-δ-9-prostaglandin d2PW_C001687PGJ2135018774171301210811251236461361028Prostaglandin I2HMDB0001335Prostaglandin I2 or prostacyclin (or PGI2) is a member of the family of lipid molecules known as eicosanoids. It is produced in endothelial cells from prostaglandin H2 (PGH2) by the action of the enzyme prostacyclin synthase. It is a powerful vasodilator and inhibits platelet aggregation. Prostaglandin I2 is the main prostaglandin synthesized by the blood vessel wall. This suggests that it may play an important role in limiting platelet-mediated thrombosis. In particular, prostacyclin (PGI2) chiefly prevents formation of the platelet plug involved in primary hemostasis (a part of blood clot formation). The sodium salt (known as epoprostenol) has been used to treat primary pulmonary hypertension. Prostacyclin (PGI2) is released by healthy endothelial cells and performs its function through a paracrine signaling cascade that involves G protein-coupled receptors on nearby platelets and endothelial cells. The platelet Gs protein-coupled receptor (prostacyclin receptor) is activated when it binds to PGI2. This activation, in turn, signals adenylyl cyclase to produce cAMP. cAMP goes on to inhibit any undue platelet activation (in order to promote circulation) and also counteracts any increase in cytosolic calcium levels which would result from thromboxane A2 (TXA2) binding (leading to platelet activation and subsequent coagulation). PGI2 also binds to endothelial prostacyclin receptors and in the same manner raise cAMP levels in the cytosol. This cAMP then goes on to activate protein kinase A (PKA). PKA then continues the cascade by inhibiting myosin light-chain kinase which leads to smooth muscle relaxation and vasodilation. Notably, PGI2 and TXA2 work as antagonists. PGI2 is stable in basic buffers (pH=8), but it is rapidly hydrolyzed to 6-keto PGF1alpha in neutral or acidic solutions. The half-life is short both in vivo and in vitro, ranging from 30 seconds to a few minutes. PGI2 is administered by continuous infusion in humans for the treatment of idiopathic pulmonary hypertension.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.35121-78-9C013125282411155525Z13E-15S-69-ALPHA-EPOXY-11-ALPHA4445566CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@@H]2OC(C[C@H]12)=CCCCC(O)=OC20H32O5InChI=1S/C20H32O5/c1-2-3-4-7-14(21)10-11-16-17-12-15(8-5-6-9-20(23)24)25-19(17)13-18(16)22/h8,10-11,14,16-19,21-22H,2-7,9,12-13H2,1H3,(H,23,24)/b11-10+,15-8-/t14-,16+,17+,18+,19-/m0/s1KAQKFAOMNZTLHT-OZUDYXHBSA-N5-[(3aR,4R,5R,6aS)-5-hydroxy-4-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-hexahydro-2H-cyclopenta[b]furan-2-ylidene]pentanoic acid352.4651352.224974134-3.413epoprostenol0-1FDB022560(5z,13e)-(15s)-6,9-alpha-epoxy-11-alpha,15-dihydroxyprosta-5,13-dienoate;(5z,13e)-(15s)-6,9-alpha-epoxy-11-alpha,15-dihydroxyprosta-5,13-dienoic acid;(5z,13e)-(15s)-6,9-epoxy-11,15-dihydroxyprosta-5,13-dienoate;(5z,13e)-(15s)-6,9-epoxy-11,15-dihydroxyprosta-5,13-dienoic acid;(5z,13e)-(15s)-6,9alpha-epoxy-11alpha,15-dihydroxyprosta-5,13-dienoate;(5z,13e)-(15s)-6,9alpha-epoxy-11alpha,15-dihydroxyprosta-5,13-dienoic acid;(5z,13e,15s)-6,9a-epoxy-11a,15-dihydroxyprosta-5,13-dienoate;(5z,13e,15s)-6,9a-epoxy-11a,15-dihydroxyprosta-5,13-dienoic acid;(5z,9a,11a,13e,15s)-6,9-epoxy-11,15-dihydroxyprosta-5,13-dien-1-oate;(5z,9a,11a,13e,15s)-6,9-epoxy-11,15-dihydroxyprosta-5,13-dien-1-oic acid;(5z,9alpha,11alpha,13e,15s)-6,9-epoxy-11,15-dihydroxyprosta-5,13-dien-1-oate;(5z,9alpha,11alpha,13e,15s)-6,9-epoxy-11,15-dihydroxyprosta-5,13-dien-1-oic acid;Epoprostenol;Pgi2;Pgx;Prostacyclin;Prostacycline;Prostaglandin i2;Prostaglandin x;Vasocyclin;Flolan;(5z,13e)-(15s)-6,9a-epoxy-11a,15-dihydroxyprosta-5,13-dienoate;(5z,13e)-(15s)-6,9a-epoxy-11a,15-dihydroxyprosta-5,13-dienoic acid;(5z,13e)-(15s)-6,9α-epoxy-11α,15-dihydroxyprosta-5,13-dienoate;(5z,13e)-(15s)-6,9α-epoxy-11α,15-dihydroxyprosta-5,13-dienoic acid;(5z,9α,11α,13e,15s)-6,9-epoxy-11,15-dihydroxyprosta-5,13-dien-1-oate;(5z,9α,11α,13e,15s)-6,9-epoxy-11,15-dihydroxyprosta-5,13-dien-1-oic acidPW_C001028PrstgI26112135118420015774181301210821251236471361084Prostaglandin D2HMDB0001403Prostaglandin D2 (or PGD2) is a prostaglandin that is actively produced in various organs such as the brain, spleen, thymus, bone marrow, uterus, ovary, oviduct, testis, prostate and epididymis, and is involved in many physiological events. PGD2 binds to the prostaglandin D2 receptor (PTGDR) which is a G-protein-coupled receptor. Its activity is mainly mediated by G-S proteins that stimulate adenylate cyclase resulting in an elevation of intracellular cAMP and Ca2+. PGD2 promotes sleep; regulates body temperature, olfactory function, hormone release, and nociception in the central nervous system; prevents platelet aggregation; and induces vasodilation and bronchoconstriction. PGD2 is also released from mast cells as an allergic and inflammatory mediator. Prostaglandin H2 is an unstable intermediate formed from PGG2 by the action of cyclooxygenase (COX) in the arachidonate cascade. In mammalian systems, it is efficiently converted into more stable arachidonate metabolites, such as PGD2, PGE2, PGF2a by the action of three groups of enzymes, PGD synthases (PGDS), PGE synthases and PGF synthases, respectively. PGDS catalyzes the isomerization of PGH2 to PGD2. Two types of PGD2 synthase are known. Lipocalin-type PGD synthase is present in cerebrospinal fluid, seminal plasma and may play an important role in male reproduction. Another PGD synthase, hematopoietic PGD synthase is present in the spleen, fallopian tube, endometrial gland cells, extravillous trophoblasts and villous trophoblasts, and perhaps plays an important role in female reproduction. Recent studies demonstrate that PGD2 is probably involved in multiple aspects of inflammation through its dual receptor systems, DP and CRTH2. (PMID: 12148545)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.41598-07-6C00696448457155555Z13E-15S-9-ALPHA15-DIHYDROXY-11-O395250DB02056[H][C@](O)(CCCCC)\C=C\[C@@]1([H])C(=O)C[C@]([H])(O)[C@]1([H])C\C=C/CCCC(O)=OC20H32O5InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-18,21-22H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,18-/m0/s1BHMBVRSPMRCCGG-OUTUXVNYSA-N(5Z)-7-[(1R,2R,5S)-5-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-3-oxocyclopentyl]hept-5-enoic acid352.4651352.224974134-3.613prostaglandin D20-1FDB022602(5z,13e)-(15s)-9,15-dihydroxy-11-oxoprosta-5,13-dienoate;(5z,13e)-(15s)-9,15-dihydroxy-11-oxoprosta-5,13-dienoic acid;(5z,13e)-(15s)-9a,15-dihydroxy-11-oxoprosta-5,13-dienoate;(5z,13e)-(15s)-9a,15-dihydroxy-11-oxoprosta-5,13-dienoic acid;(5z,13e)-(15s)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoic acid;(5z,13e)-(15s)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate;(5z,13e,15s)-9-alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate;(5z,13e,15s)-9-alpha,15-dihydroxy-11-oxoprosta-5,13-dienoic acid;(5z,13e,15s)-9a,15-dihydroxy-11-oxoprosta-5,13-dien-1-oate;(5z,13e,15s)-9a,15-dihydroxy-11-oxoprosta-5,13-dien-1-oic acid;(5z,9-alpha,13e,15s)-9,15-dihydroxy-11-oxo-prosta-5,13-dien-1-oate;(5z,9-alpha,13e,15s)-9,15-dihydroxy-11-oxo-prosta-5,13-dien-1-oic acid;(5z,9alpha,13e,15s)-9,15-dihydroxy-11-oxo-prosta-5,13-dien-1-oate;(5z,9alpha,13e,15s)-9,15-dihydroxy-11-oxo-prosta-5,13-dien-1-oic acid;(5z,13e)-(15s)-9-alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate;(5z,13e)-(15s)-9-alpha,15-dihydroxy-11-oxoprosta-5,13-dienoic acid;11-dehydroprostaglandin f2-alpha;11-dehydroprostaglandin f2alpha;9s,15s-dihydroxy-11-oxo-5z,13e-prostadienoate;9s,15s-dihydroxy-11-oxo-5z,13e-prostadienoic acid;Pgd2;Prostaglandin d2;(5z,13e,15s)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate;(5z,13e)-(15s)-9α,15-dihydroxy-11-oxoprosta-5,13-dienoate;(5z,13e)-(15s)-9α,15-dihydroxy-11-oxoprosta-5,13-dienoic acid;(5z,13e,15s)-9a,15-dihydroxy-11-oxoprosta-5,13-dienoate;(5z,13e,15s)-9a,15-dihydroxy-11-oxoprosta-5,13-dienoic acid;(5z,13e,15s)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoic acid;(5z,13e,15s)-9α,15-dihydroxy-11-oxoprosta-5,13-dienoate;(5z,13e,15s)-9α,15-dihydroxy-11-oxoprosta-5,13-dienoic acidPW_C001084ProglD26172135218416515774191301210831251236481361068Prostaglandin H2HMDB0001381Prostaglandin 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 and are 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 signalling pathways.42935-17-1C0042744504915554PROSTAGLANDIN-H2392800CCCCC[C@H](O)\C=C\[C@H]1[C@H]2C[C@H](OO2)[C@@H]1C\C=C/CCCC(O)=OC20H32O5InChI=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)/b7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1YIBNHAJFJUQSRA-YNNPMVKQSA-N(5Z)-7-[(1R,4S,5R,6R)-6-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hept-5-enoic acid352.4651352.224974134-4.022prostaglandin H20-1FDB022592(15s)hydroxy-9alpha,11alpha-(epoxymethano)prosta-5,13-dienoate;(15s)hydroxy-9alpha,11alpha-(epoxymethano)prosta-5,13-dienoic 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;(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)-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)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate;(5z,13e)-(15s)-9alpha,11alpha-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)-9a,11a-epidioxy-15-hydroxyprosta-5,13-dienoate;(5z,13e,15s)-9a,11a-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;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;(5z,13e,15s)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate;(5z,9alpha,11alpha,13e,15s)-9,11-epidioxy-15-hydroxyprosta-5,13-dien-1-oic 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)-9α,11α-epidioxy-15-hydroxyprosta-5,13-dienoate;(5z,13e)-(15s)-9α,11α-epidioxy-15-hydroxyprosta-5,13-dienoic acid;(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,9alpha,11alpha,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-oate;(5z,9α,11α,13e,15s)-9,11-epidioxy-15-hydroxyprosta-5,13-dien-1-oic acidPW_C001068PGH224916610213534977420331121084383123649398677611-Epi-PGF2aHMDB001113711-epi-PGF2alpha is an intermediate in Arachidonic acid metabolism. 11-epi-PGF2alpha is converted from (5Z,13E)-(15S)-9alpha,15-Dihydroxy-11-oxoprosta-5,13-dienoate via the enzyme prostaglandin-F synthase (EC 1.1.1.188).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.C059595348066927595CCCCC[C@H](O)\C=C\[C@H]1[C@@H](O)CC(O)C1C\C=C/CCCC(O)=OC20H34O5InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16?,17+,18?,19-/m0/s1PXGPLTODNUVGFL-BTJIPTOOSA-N(5Z)-7-[(2R,3S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid354.481354.240624198-3.484(5Z)-7-[(2R,3S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid0-1C0595911-epi-pgf2a;11-epi-pgf2alpha;11-epi-prostaglandin f2a;11-epi-prostaglandin f2alphaPW_C006776EiPGF2a13578774211111210881221236531351121Thromboxane A2HMDB0001452Thromboxane A2 is an unstable intermediate between the prostaglandin endoperoxides and thromboxane B2. The compound has a bicyclic oxaneoxetane structure. It is a potent inducer of platelet aggregation and causes vasoconstriction. It is the principal component of rabbit aorta contracting substance (RCS).Thromboxanes 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.57576-52-0C02198528049715627ALPHA11-ALPHA-EPOXY-15-HYDROXYTHROMBA4444137CCCCC[C@H](O)\C=C\[C@H]1O[C@H]2C[C@H](O2)[C@@H]1C\C=C/CCCC(O)=OC20H32O5InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18-14-20(24-17)25-18)10-7-4-5-8-11-19(22)23/h4,7,12-13,15-18,20-21H,2-3,5-6,8-11,14H2,1H3,(H,22,23)/b7-4-,13-12+/t15-,16+,17+,18-,20+/m0/s1DSNBHJFQCNUKMA-SCKDECHMSA-N(5Z)-7-[(1S,3R,4S,5S)-3-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-2,6-dioxabicyclo[3.1.1]heptan-4-yl]hept-5-enoic acid352.4651352.224974134-3.882thromboxane0-1FDB022632(1s-(1alpha,3alpha,3r*),4beta(z),5alpha)-7-(3-(3-hydroxy-1-octenyl)-2,6-dioxabicyclo(3.1.1)hept-4-yl)-5-heptenoate;(1s-(1alpha,3alpha,3r*),4beta(z),5alpha)-7-(3-(3-hydroxy-1-octenyl)-2,6-dioxabicyclo(3.1.1)hept-4-yl)-5-heptenoic acid;(5z)-7-[(1s,3r,4s,5s)-3-[(1e,3s)-3-hydroxy-1-octenyl]-2,6-dioxabicyclo[3.1.1]hept-4-yl]-5-heptenoate;(5z)-7-[(1s,3r,4s,5s)-3-[(1e,3s)-3-hydroxy-1-octenyl]-2,6-dioxabicyclo[3.1.1]hept-4-yl]-5-heptenoic acid;(5z,13e)-(15s)-9,11-epoxy-15-hydroxythromba-5,13-dienoate;(5z,13e)-(15s)-9,11-epoxy-15-hydroxythromba-5,13-dienoic acid;(5z,13e)-(15s)-9-alpha,11-alpha-epoxy-15-hydroxythromboxa-5,13-dienoate;(5z,13e)-(15s)-9-alpha,11-alpha-epoxy-15-hydroxythromboxa-5,13-dienoic acid;(5z,13e)-(15s)-9a,11a-epoxy-15-hydroxythromboxa-5,13-dienoate;(5z,13e)-(15s)-9a,11a-epoxy-15-hydroxythromboxa-5,13-dienoic acid;(5z,13e)-(15s)-9alpha,11alpha-epoxy-15-hydroxythromboxa-5,13-dienoate;(5z,13e)-(15s)-9alpha,11alpha-epoxy-15-hydroxythromboxa-5,13-dienoic acid;(5z,9alpha,11alpha,13e,15s)-9,11-epoxy-15-hydroxythromboxa-5,13-dien-1-oate;(5z,9alpha,11alpha,13e,15s)-9,11-epoxy-15-hydroxythromboxa-5,13-dien-1-oic acid;(5z,9alpha,11alpha,13e,15s)-9,11-epoxy-15-hydroxy-thromboxa-5,13-dien-1-oate;(5z,9alpha,11alpha,13e,15s)-9,11-epoxy-15-hydroxy-thromboxa-5,13-dien-1-oic acid;7-[3-(3-hydroxy-1-octenyl)-2,6-dioxabicyclo[3.1.1]hept-4-yl]-[1s-[1alpha,3alpha(1e,3r*),4beta(z),5alpha]]-5-heptenoate;7-[3-(3-hydroxy-1-octenyl)-2,6-dioxabicyclo[3.1.1]hept-4-yl]-[1s-[1alpha,3alpha(1e,3r*),4beta(z),5alpha]]-5-heptenoic acid;9s,11s-epoxy,15s-hydroxy-thromboxa-5z,13e-dien-1-oate;9s,11s-epoxy,15s-hydroxy-thromboxa-5z,13e-dien-1-oic acid;Cid;Rcs;Rabbit aorta contracting substance;Txa-2;Txa2;(5z,13e)-(15s)-9α,11α-epoxy-15-hydroxythromboxa-5,13-dienoate;(5z,13e)-(15s)-9α,11α-epoxy-15-hydroxythromboxa-5,13-dienoic acid;(5z,9a,11a,13e,15s)-9,11-epoxy-15-hydroxythromboxa-5,13-dien-1-oate;(5z,9a,11a,13e,15s)-9,11-epoxy-15-hydroxythromboxa-5,13-dien-1-oic acid;(5z,9α,11α,13e,15s)-9,11-epoxy-15-hydroxythromboxa-5,13-dien-1-oate;(5z,9α,11α,13e,15s)-9,11-epoxy-15-hydroxythromboxa-5,13-dien-1-oic acidPW_C001121ThrmbA22501662129611510601413594977422331121090383123655398949Prostaglandin E2HMDB0001220The naturally occurring prostaglandin E2 (PGE2) is known in medicine as dinoprostone, and it is the most common and most biologically active of the mammalian prostaglandins. It has important effects during labour and also stimulates osteoblasts to release factors which stimulate bone resorption by osteoclasts (a type of bone cell that removes bone tissue by removing the bone's mineralized matrix). PGE2 is also the prostaglandin that ultimately induces fever. PGE2 has been shown to increase vasodilation and cAMP production, enhance the effects of bradykinin and histamine, and induce uterine contractions and platelet aggregation. PGE2 is also responsible for maintaining the open passageway of the fetal ductus arteriosus, decreasing T-cell proliferation and lymphocyte migration, and activating the secretion of IL-1α and IL-2. PGE2 exhibits both pro- and anti-inflammatory effects, particularly on dendritic cells (DC). Depending on the nature of maturation signals, PGE2 has different and sometimes opposite effects on DC biology. PGE2 exerts an inhibitory action, reducing the maturation of DC and their ability to present antigen. PGE2 has also been shown to stimulate DC and promote IL-12 production when given in combination with TNF-alpha. PGE2 is an environmentally bioactive substance. Its action is prolonged and sustained by other factors especially IL-10. It modulates the activities of professional DC by acting on their differentiation, maturation, and their ability to secrete cytokines. PGE2 is a potent inducer of IL-10 in bone marrow-derived DC (BM-DC). PGE2-induced IL-10 is a key regulator of the BM-DC pro-inflammatory phenotype (PMID: 16978535). 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 and are 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 signalling pathways.363-24-6C005845280360155515Z13E-15S-1115-DIHYDROXY-9-OXOPROS4444059DB00917CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=OC20H32O5InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,19+/m0/s1XEYBRNLFEZDVAW-ARSRFYASSA-N(5Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]hept-5-enoic acid352.4651352.224974134-3.903dinoprostone0-1FDB022498(-)-prostaglandin e2;(5z,13e)-(15s)-11alpha,15-dihydroxy-9-oxoprost-13-enoate;(5z,13e)-(15s)-11alpha,15-dihydroxy-9-oxoprost-13-enoic acid;(5z,13e)-(15s)-11alpha,15-dihydroxy-9-oxoprosta-5,13-dienoate;(5z,13e)-(15s)-11alpha,15-dihydroxy-9-oxoprosta-5,13-dienoic acid;(5z,13e,15s)-11-alpha,15-dihydroxy-9-oxoprost-5,13-dienoate;(5z,13e,15s)-11-alpha,15-dihydroxy-9-oxoprost-5,13-dienoic acid;5-trans-pge2;Dinoprostone;Dinoprostonum;Glandin;L-prostaglandin e2;Minprositin e2;Minprostin e2;Pge2;Prepidil;Prostaglandin e;Prostaglandin e2;Prostaglandin e2alpha;Prostarmon e;Prostin;Prostin e2;(15s)-prostaglandin e2;(5z,11alpha,13e,15s)-11,15-dihydroxy-9-oxoprosta-5,13-dien-1-oic acid;(e,z)-(1r,2r,3r)-7-(3-hydroxy-2-((3s)-(3-hydroxy-1-octenyl))-5-oxocyclopentyl)-5-heptenoic acid;(z)-7-((1r,2r,3r)-3-hydroxy-2-((s,e)-3-hydroxyoct-1-enyl)-5-oxocyclopentyl)hept-5-enoic acid;Dinoproston;Dinoprostona;Propess;(5z,11a,13e,15s)-11,15-dihydroxy-9-oxoprosta-5,13-dien-1-oate;(5z,11a,13e,15s)-11,15-dihydroxy-9-oxoprosta-5,13-dien-1-oic acid;(5z,11alpha,13e,15s)-11,15-dihydroxy-9-oxoprosta-5,13-dien-1-oate;(5z,11α,13e,15s)-11,15-dihydroxy-9-oxoprosta-5,13-dien-1-oate;(5z,11α,13e,15s)-11,15-dihydroxy-9-oxoprosta-5,13-dien-1-oic acid;(5z,13e)-(15s)-11a,15-dihydroxy-9-oxoprost-13-enoate;(5z,13e)-(15s)-11a,15-dihydroxy-9-oxoprost-13-enoic acid;(5z,13e)-(15s)-11α,15-dihydroxy-9-oxoprost-13-enoate;(5z,13e)-(15s)-11α,15-dihydroxy-9-oxoprost-13-enoic acid;(5z,13e)-(15s)-11a,15-dihydroxy-9-oxoprosta-5,13-dienoate;(5z,13e)-(15s)-11a,15-dihydroxy-9-oxoprosta-5,13-dienoic acid;(5z,13e)-(15s)-11α,15-dihydroxy-9-oxoprosta-5,13-dienoate;(5z,13e)-(15s)-11α,15-dihydroxy-9-oxoprosta-5,13-dienoic acid;(e,z)-(1r,2r,3r)-7-(3-hydroxy-2-((3s)-(3-hydroxy-1-octenyl))-5-oxocyclopentyl)-5-heptenoate;(z)-7-((1r,2r,3r)-3-hydroxy-2-((s,e)-3-hydroxyoct-1-enyl)-5-oxocyclopentyl)hept-5-enoatePW_C000949PGE26132136149774233311158838121092383123657398889Prostaglandin F2aHMDB0001139Prostaglandin F2a (PGF2) is one of the earliest discovered and most common prostaglandins. It is actively biosynthesized in various organs of mammals and exhibits a variety of biological activities, including contraction of pulmonary arteries. It is used in medicine to induce labor and as an abortifacient. PGF2a binds to the Prostaglandin F2 receptor (PTGFR) which is a member of the G-protein coupled receptor family. PGF2-alpha mediates luteolysis. Luteolysis is the structural and functional degradation of the corpus luteum (CL) that occurs at the end of the luteal phase of both the estrous and menstrual cycles in the absence of pregnancy. PGF2 may also be involved in modulating intraocular pressure and smooth muscle contraction in the uterus and gastrointestinal tract sphincters. PGF2 is mainly synthesized directly from PGH2 by PGH2 9,11-endoperoxide reductase. A small amount of PGF2 is also produced from PGE2 by PGE2 9-ketoreductase. A PGF2 epimer has been reported to exhibit various biological activities, and its levels are increased in bronchoalveolar lavage fluid, plasma, and urine in patients with mastocytosis and bronchial asthma. PGF2 is synthesized from PGD2 by PGD2 11-ketoreductase. (PMID: 16475787). 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.551-11-1C006395283078155535Z13E-15S-9-ALPHA11-ALPHA15-TRIHY4446204CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C\CCCC(O)=OC20H34O5InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4+,13-12+/t15-,16+,17+,18-,19+/m0/s1PXGPLTODNUVGFL-UAAPODJFSA-N(5E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid354.481354.240624198-3.4845-trans-PGF2α0-1FDB022448(+)-prostaglandin f2a;(5z,13e)-(15s)-9-alpha,11-alpha,15-trihydroxyprosta-5,13-dienoate;(5z,13e)-(15s)-9-alpha,11-alpha,15-trihydroxyprosta-5,13-dienoic acid;(5z,13e,15s)-9a,11a,15-trihydroxyprosta-5,13-dien-1-oate;(5z,13e,15s)-9a,11a,15-trihydroxyprosta-5,13-dien-1-oic acid;(5z,9a,11a,13e,15s)-9,11,15-trihydroxy-prosta-5,13-dien-1-oate;(5z,9a,11a,13e,15s)-9,11,15-trihydroxy-prosta-5,13-dien-1-oic acid;(9alpha,11alpha,15)-trihydroxyprosta-(5z,13e)-dien-1-oate;(9alpha,11alpha,15)-trihydroxyprosta-(5z,13e)-dien-1-oic acid;7-[3,5-dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl]-5-heptenoic acid;7-[3,5-dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl]-5-heptenoate;9,11,15-trihydroxy-(5z,9a,11a,13e,15s)-prosta-5,13-dien-1-oate;9,11,15-trihydroxy-(5z,9a,11a,13e,15s)-prosta-5,13-dien-1-oic acid;9,11,15-trihydroxyprosta-5z,13e-dien-1-oate;9,11,15-trihydroxyprosta-5z,13e-dien-1-oic acid;9a,11a,15(s)-trihydroxy-5-cis-13-trans-prostadienoate;9a,11a,15(s)-trihydroxy-5-cis-13-trans-prostadienoic acid;9a,11a-pgf2;9a,11a-pgf2a;Amoglandin;Cyclosin;Dinifertin;Dinoprost;Enzaprost;Enzaprost f;F2a isoprostane;Glandin n;L-pgf2-alpha;L-prostaglandin f2-alpha;Pgf2a;Panacelan;Prostaglandin f2;Prostaglandin f2a;Prostamate;Prostarmon f;Prostin f 2 alpha;ProtamodinPW_C000889PGF2a619213648774251111210951221236601351699Prostaglandin A2HMDB0002752Produced by the seminal vesicles, prostaglandins are a group of lipid compounds that are derived enzymatically from fatty acids. Technically hormones, the prostanoid class of fatty acid derivatives is a subclass of 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. Prostaglandin A is a cyclopentenone and is an endogenous metabolite derived from arachidonic acid. It exhibits potent cellular anti-proliferative activity in vivo and in vitro. Excess PGA2 causes an accumulation in both S and G2/M, and a marked decrease in G1. There is also an increase in DNA content preceeding the G0/G1 peak (indicative of apoptotic body formation) mediated by changes in expression levels of Bax and Bcl-2.13345-50-1C059535280880278204444403CCCCC[C@H](O)\C=C\[C@H]1C=CC(=O)[C@@H]1C\C=C/CCCC(O)=OC20H30O4InChI=1S/C20H30O4/c1-2-3-6-9-17(21)14-12-16-13-15-19(22)18(16)10-7-4-5-8-11-20(23)24/h4,7,12-18,21H,2-3,5-6,8-11H2,1H3,(H,23,24)/b7-4-,14-12+/t16-,17-,18+/m0/s1MYHXHCUNDDAEOZ-FOSBLDSVSA-N(5Z)-7-[(1R,2S)-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-3-en-1-yl]hept-5-enoic acid334.4498334.214409448-4.212prostaglandin A20-1FDB0230607-[2-(3-hydroxy-1-octenyl)-5-oxo-3-cyclopenten-1-yl]-5-Heptenoic acid;(5Z,13E,15S)-15-Hydroxy-9-oxoprosta-5,10,13-trien-1-oic acid;(+)-Prostaglandin A2;(15S)-PGA2;15(S)-Hydroxy-9-oxo-5-cis-10,13-trans-prostatrienoate;15(S)-Hydroxy-9-oxo-5-cis-10,13-trans-prostatrienoic acid;15(S)-Hydroxy-9-oxo-5-cis-10,13-trans-prostenoate;15(S)-Hydroxy-9-oxo-5-cis-10,13-trans-prostenoic acid;15(S)-Prostaglandin A2;15α-Hydroxy-9-oxo-cis-5,10,trans-13-prostatrienecarboxylate;15α-Hydroxy-9-oxo-cis-5,10,trans-13-prostatrienecarboxylic acid;15α-Hydroxy-9-oxo-cis-5,10,trans-13-prostatrienoate;15α-Hydroxy-9-oxo-cis-5,10,trans-13-prostatrienoic acid;5,6-cis-PGA2;Medullin;NSC 165561;PGA2PW_C001699PGA21367187742613012109812512366313640451Prostaglandin-c2HMDB0060095Prostaglandin-C2, also known as PGC2, 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. Thus, prostaglandin-C2 is considered to be an eicosanoid lipid molecule. Prostaglandin-C2 is considered to be a practically insoluble (in water) and relatively neutral molecule. Prostaglandin-C2 has been primarily detected in urine. Within the cell, prostaglandin-C2 is primarily located in the membrane (predicted from logP) and cytoplasm. In humans, prostaglandin-C2 is involved in the nabumetone action pathway, the antrafenine action pathway, the phenylbutazone action pathway, and the trisalicylate-choline action pathway. Prostaglandin-C2 is also involved in a couple of metabolic disorders, which include leukotriene C4 synthesis deficiency and the tiaprofenic Acid action pathway. This compound belongs to the family of Prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.C059555280882275554444405CCCCC[C@H](O)\C=C\C1=CCC(=O)[C@@H]1C\C=C/CCCC(O)=OC20H30O4InChI=1S/C20H30O4/c1-2-3-6-9-17(21)14-12-16-13-15-19(22)18(16)10-7-4-5-8-11-20(23)24/h4,7,12-14,17-18,21H,2-3,5-6,8-11,15H2,1H3,(H,23,24)/b7-4-,14-12+/t17-,18+/m0/s1CMBOTAQMTNMTBD-KLASNZEFSA-N(5Z)-7-[(1R)-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-2-en-1-yl]hept-5-enoic acid334.4498334.214409448-4.132prostaglandin C20-1Pgc2PW_C040451ProC2136818774271301210991251236641361820Thromboxane B2HMDB0003252Thromboxanes. A stable, physiologically active compound formed in vivo from the prostaglandin endoperoxides. It is important in the platelet-release reaction (release of ADP and serotonin). -- Pubchem. Thromboxanes 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.54397-85-2C059635283137287284446261CCCCC[C@H](O)\C=C\[C@H]1OC(O)C[C@H](O)[C@@H]1C\C=C/CCCC(O)=OC20H34O6InChI=1S/C20H34O6/c1-2-3-6-9-15(21)12-13-18-16(17(22)14-20(25)26-18)10-7-4-5-8-11-19(23)24/h4,7,12-13,15-18,20-22,25H,2-3,5-6,8-11,14H2,1H3,(H,23,24)/b7-4-,13-12+/t15-,16-,17-,18+,20?/m0/s1XNRNNGPBEPRNAR-JQBLCGNGSA-N(5Z)-7-[(2R,3S,4S)-4,6-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]oxan-3-yl]hept-5-enoic acid370.4804370.23553882-3.184thromboxane B20-1FDB023130Txb2PW_C001820TXB2136918774281301211001251236651362099Prostaglandin B2HMDB0004236Prostaglandin B2 (PGB2) is a prostanoid. Prostanoids is a term that collectively describes prostaglandins, prostacyclines and thromboxanes. Prostanoids are a subclass of the lipid mediator group known as eicosanoids. They derive from C-20 polyunsaturated fatty acids, mainly dihomo-gamma-linoleic (20:3n-6), arachidonic (20:4n-6), and eicosapentaenoic (20:5n-3) acids, through the action of cyclooxygenases-1 and -2 (COX-1 and COX-2). The reaction product of COX is the unstable endoperoxide prostaglandin H (PGH) that is further transformed into the individual prostanoids by a series of specific prostanoid synthases. Prostanoids are local-acting mediators formed and inactivated within the same or neighbouring cells prior to their release into circulation as inactive metabolites (15-keto- and 13,14-dihydroketo metabolites). Non-enzymatic peroxidation of arachidonic acid and other fatty acids in vivo can result in prostaglandin-like substances isomeric to the COX-derived prostaglandins that are termed isoprostanes. Prostanoids take part in many physiological and pathophysiological processes in practically every organ, tissue and cell, including the vascular, renal, gastrointestinal and reproductive systems. Their activities are mediated through prostanoid-specific receptors and intracellular signalling pathways, whilst their biosynthesis and action are blocked by nonsteroidal antiinflammatory drugs (NSAID). Isoprostanes are considered to be reliable markers of oxidant stress status and have been linked to inflammation, ischaemia-reperfusion, diabetes, cardiovascular disease, reproductive disorders and diabetes. (PMID: 16986207). 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.13367-85-6C059545288144280994450370CCCCC[C@@H](O)\C=C\C1=C(C\C=C/CCCC(O)=O)C(=O)CC1C20H30O4InChI=1S/C20H30O4/c1-2-3-6-9-17(21)14-12-16-13-15-19(22)18(16)10-7-4-5-8-11-20(23)24/h4,7,12,14,17,21H,2-3,5-6,8-11,13,15H2,1H3,(H,23,24)/b7-4-,14-12+/t17-/m1/s1PRFXRIUZNKLRHM-RYPCXPIFSA-N(5Z)-7-{2-[(1E,3R)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoic acid334.4498334.214409448-4.052(5Z)-7-{2-[(1E,3R)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoic acid0-1FDB023342Pgb2PW_C002099PGB213701877429130121101125123666136210411-Dehydro-thromboxane B2HMDB000424211-Dehydro-thromboxane B2, a stable thromboxane metabolite, is a full agonist of chemoattractant receptor-homologous molecule expressed on TH2 cells (CRTH2) in human eosinophils and basophils. Given its production in the allergic lung, antagonism of the 11-dehydro- thromboxane B2/CRTH2axis may be of therapeutic relevance. (PMID 14668348)Thromboxanes 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.67910-12-7C05964534777812866730776537CCCCC[C@H](O)\C=C\[C@H]1OC(=O)C[C@H](O)[C@@H]1C\C=C\CCCC(O)=OC20H32O6InChI=1S/C20H32O6/c1-2-3-6-9-15(21)12-13-18-16(17(22)14-20(25)26-18)10-7-4-5-8-11-19(23)24/h4,7,12-13,15-18,21-22H,2-3,5-6,8-11,14H2,1H3,(H,23,24)/b7-4+,13-12+/t15-,16-,17-,18+/m0/s1KJYIVXDPWBUJBQ-SOGWKEBJSA-N(5E)-7-[(2R,3S,4S)-4-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-6-oxooxan-3-yl]hept-5-enoic acid368.4645368.219888756-3.553(5E)-7-[(2R,3S,4S)-4-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-6-oxooxan-3-yl]hept-5-enoic acid0-1FDB02334711-dehydro-thromboxane;11-dehydro-txb2;11-dehydrotxb2;11-dehydrothromboxane;11-dehydrothromboxane b2;11-keto-thromboxanePW_C00210411DTB213711877430130121102125123667136821Arachidonic acidHMDB0001043Arachidonic acid is a polyunsaturated, essential fatty acid that has a 20-carbon chain as a backbone and four cis-double bonds at the C5, C8, C11, and C14 positions. It is found in animal and human fat as well as in the liver, brain, and glandular organs, and is a constituent of animal phosphatides. It is synthesized from dietary linoleic acid. Arachidonic acid mediates inflammation and the functioning of several organs and systems either directly or upon its conversion into eicosanoids. Arachidonic acid in cell membrane phospholipids is the substrate for the synthesis of a range of biologically active compounds (eicosanoids) including prostaglandins, thromboxanes, and leukotrienes. These compounds can act as mediators in their own right and can also act as regulators of other processes, such as platelet aggregation, blood clotting, smooth muscle contraction, leukocyte chemotaxis, inflammatory cytokine production, and immune function. Arachidonic acid can be metabolized by cytochrome p450 (CYP450) enzymes into 5,6-, 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acids (EETs), their corresponding dihydroxyeicosatrienoic acids (DHETs), and 20-hydroxyeicosatetraenoic acid (20-HETE). The production of kidney CYP450 arachidonic acid metabolites is altered in diabetes, pregnancy, hepatorenal syndrome, and in various models of hypertension, and it is likely that changes in this system contribute to the abnormalities in renal function that are associated with many of these conditions. Phospholipase A2 (PLA2) catalyzes the hydrolysis of the sn-2 position of membrane glycerophospholipids to liberate arachidonic acid (PMID: 12736897, 12736897, 12700820, 12570747, 12432908).506-32-1C0021944489915843ARACHIDONIC_ACID392692DB04557CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=OC20H32O2InChI=1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-15-YZXBAPSDXZZRGB-DOFZRALJSA-N(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid304.4669304.240230268-6.301arachidonic acid0-1FDB011872(all-z)-5,8,11,14-eicosatetraenoate;(all-z)-5,8,11,14-eicosatetraenoic acid;5,8,11,14-all-cis-eicosatetraenoate;5,8,11,14-all-cis-eicosatetraenoic acid;5,8,11,14-eicosatetraenoate;5,8,11,14-eicosatetraenoic acid;5-cis,8-cis,11-cis,14-cis-eicosatetraenoate;5-cis,8-cis,11-cis,14-cis-eicosatetraenoic acid;5z,8z,11z,14z-eicosatetraenoate;5z,8z,11z,14z-eicosatetraenoic acid;All-cis-5,8,11,14-eicosatetraenoate;All-cis-5,8,11,14-eicosatetraenoic acid;Arachidonic acid;Immunocytophyte;Cis-d5,8,11,14-eicosatetraenoate;Cis-d5,8,11,14-eicosatetraenoic acid;(5z,8z,11z,14z)-5,8,11,14-icosatetraenoic acid;(5z,8z,11z,14z)-icosatetraenoic acid;Aa;Ara;Arachidonate;Arachidonsaeure;Cis-5,8,11,14-eicosatetraenoic acid;Cis-delta(5,8,11,14)-eicosatetraenoic acid;(5z,8z,11z,14z)-5,8,11,14-icosatetraenoate;(5z,8z,11z,14z)-icosatetraenoate;Cis-5,8,11,14-eicosatetraenoate;Cis-delta(5,8,11,14)-eicosatetraenoate;Cis-δ(5,8,11,14)-eicosatetraenoate;Cis-δ(5,8,11,14)-eicosatetraenoic acid;FA(20:4(5Z,8Z,11Z,14Z))PW_C00082120:42441629618600213728772721301202131251228901361255663001270973958133Fe3+HMDB0012943Fe3+, also known as ferric ion or fe(iii), belongs to the class of inorganic compounds known as homogeneous transition metal compounds. These are inorganic compounds containing only metal atoms,with the largest atom being a transition metal atom. Fe3+ exists in all living organisms, ranging from bacteria to humans. 2,3-Dihydroxybenzoylserine and fe3+ can be biosynthesized from ferric enterobactin through its interaction with the enzyme enterochelin esterase. Outside of the human body, fe3+ can be found in a number of food items such as bamboo shoots, catjang pea, chickpea, and orange bell pepper. This makes fe3+ a potential biomarker for the consumption of these food products. The major activity of supplemental iron is in the prevention and treatment of iron deficiency anemia. Iron has putative immune-enhancing, anticarcinogenic and cognition-enhancing activities.20074-52-6C148192993629034CPD-1013427815[Fe+3]FeInChI=1S/Fe/q+3VTLYFUHAOXGGBS-UHFFFAOYSA-Niron(3+) ion55.84555.9349421330iron(3+) ion33C14819Fe(iii);Ferric ion;Iron(3+);Fe (iii) ion;Fe(3+);Ferric iron;Iron, ion (fe(3+))PW_C008133Fe3+123031296814204919972704216311841160126751517743111177450331785991127872113212094940712101312212112738312159312412351511912357813512369639812415111812589048112735120612755938814071818218011H-14,15-EETAHMDB000469311H-14,15-EETA is an epoxyeicosatrienoic acid. Epoxyeicosatrienoic acids (EpETrEs) have been reported recently having vasodilatory effects and a role of P-450-dependent arachidonic acid monooxygenase metabolites is suggested in vasoregulation. The physiological role of this compound has not been totally established, although in other tissues EpETrEs are mainly involved in hormone production and in the vascular and renal systems. Some studies have implicated epoxygenase metabolites of arachidonic acid in the control of steroidogenesis in luteinised granulosa cells. (PMID: 12749593, 12361727, 1650001).219535-29-2C148131195405810128353CCCCCC1OC1\C=C\C(O)C\C=C/C\C=C/CCCC(O)=OC20H32O4InChI=1S/C20H32O4/c1-2-3-9-13-18-19(24-18)16-15-17(21)12-10-7-5-4-6-8-11-14-20(22)23/h4,6-7,10,15-19,21H,2-3,5,8-9,11-14H2,1H3,(H,22,23)/b6-4-,10-7-,16-15+WLMZMBKVRPUYIG-LTCHCNGXSA-N(5Z,8Z,12E)-11-hydroxy-13-(3-pentyloxiran-2-yl)trideca-5,8,12-trienoic acid336.4657336.230059512-4.68211-Hydroxy-14,15-EETA0-1FDB023409(5z,8z,12e)-14,15-epoxy-11-hydroxyeicosa-5,8,12-trienoate;(5z,8z,12e)-14,15-epoxy-11-hydroxyeicosa-5,8,12-trienoic acid;(5z,8z,12e)-14,15-epoxy-11-hydroxyicosa-5,8,12-trienoate;(5z,8z,12e)-14,15-epoxy-11-hydroxyicosa-5,8,12-trienoic acid;11-hydroxy-14,15-eeta;11-hydroxy-14,15-epoxy-5z,8z,12e-eicosatrienoate;11-hydroxy-14,15-epoxy-5z,8z,12e-eicosatrienoic acid;11-hydroxy-14,15-epoxyeicosatrienoate;11-hydroxy-14,15-epoxyeicosatrienoic acid;14(15)-epetre;14,15-ep-11-hetre;(5z,8z,12e)-11-hydroxy-13-(3-pentyloxiran-2-yl)trideca-5,8,12-trienoatePW_C00218011H141513764977432331121105383123670398218111,14,15-THETAHMDB000469411,14,15-trihydroxyeicosatrienoic acid (11,14,15-THETA) is a metabolite of the 15-lipoxygenase (15-LO) pathway of arachidonic acid (AA). Increased amounts of 11,14,15-THETA are synthesized in subacute hypoxia. Prolonged exposure to reduced PO2 activates 15-LO in small pulmonary arteries (PA); activation of 15-LO is associated with translocation of the enzyme from the cytosol to membrane. 11,14,15-THETA is an endothelium-derived relaxing factor. (PMID: 12690037, 9812980, 15388505, 14622984).C148141195405910128354CCCCCC(O)C(O)\C=C\C(O)C\C=C/C\C=C/CCCC(O)=OC20H34O5InChI=1S/C20H34O5/c1-2-3-9-13-18(22)19(23)16-15-17(21)12-10-7-5-4-6-8-11-14-20(24)25/h4,6-7,10,15-19,21-23H,2-3,5,8-9,11-14H2,1H3,(H,24,25)/b6-4-,10-7-,16-15+YCFPVUKKIWMCJK-LTCHCNGXSA-N(5Z,8Z,12E)-11,14,15-trihydroxyicosa-5,8,12-trienoic acid354.481354.240624198-3.824(5Z,8Z,12E)-11,14,15-trihydroxyicosa-5,8,12-trienoic acid0-1FDB023410(5z,8z,12e)-11,14,15-trihydroxyeicosa-5,8,12-trienoate;(5z,8z,12e)-11,14,15-trihydroxyeicosa-5,8,12-trienoic acid;(5z,8z,12e)-11,14,15-trihydroxyicosa-5,8,12-trienoate;(5z,8z,12e)-11,14,15-trihydroxyicosa-5,8,12-trienoic acid;11,14,15-trihydroxy-5z,8z,12e-eicosatrienoate;11,14,15-trihydroxy-5z,8z,12e-eicosatrienoic acid;11,14,15-trihydroxyicosatrienoate;11,14,15-trihydroxyicosatrienoic acidPW_C0021811415THA13794977433331121107383123672398238915H-11,12-EETAHMDB000505015H-11,12-EETA is an epoxyeicosatrienoic acid (EET). The role of EETs in regulation of the cerebral circulation has become more important, since it was realized that EETs are produced in another specialized cell type of the brain, the astrocytes. It has become evident that EETs released from astrocytes may mediate cerebral functional hyperemia. Molecular and pharmacological evidence hve shown that neurotransmitter release and spillover onto astrocytes can generate EETs. Since these EETs may reach the vasculature via astrocyte foot-processes, they have the same potential as their endothelial counterparts to hyperpolarize and dilate cerebral vessels. P450 enzymes contain heme in their catalytic domain and nitric oxide (NO) appears to bind to these heme moieties and block formation of P450 products, including EETs. Thus, there appears to be crosstalk between P450 enzymes and NO/NO synthase. The role of fatty acid metabolites and cerebral blood flow becomes even more complex in light of data demonstrating that cyclooxygenase products can act as substrates for P450 enzymes. (PMID: 17494091, 17468203, 17434916, 17406062, 17361113, 15581597, 11413051, 10519554, 11893556).877878-78-9C147811195404210128337CCCCC[C@H](O)\C=C\C1OC1C\C=C/C\C=C/CCCC(O)=OC20H32O4InChI=1S/C20H32O4/c1-2-3-9-12-17(21)15-16-19-18(24-19)13-10-7-5-4-6-8-11-14-20(22)23/h4,6-7,10,15-19,21H,2-3,5,8-9,11-14H2,1H3,(H,22,23)/b6-4-,10-7-,16-15+/t17-,18?,19?/m0/s1GELFSVXLSDZDHE-YZSNCDGGSA-N(5Z,8Z)-10-{3-[(1E,3S)-3-hydroxyoct-1-en-1-yl]oxiran-2-yl}deca-5,8-dienoic acid336.4657336.230059512-4.472(5Z,8Z)-10-{3-[(1E,3S)-3-hydroxyoct-1-en-1-yl]oxiran-2-yl}deca-5,8-dienoic acid0-1FDB023612(+/-)11,12-ep-15(s)-hetre;(5z,8z,13e)-(15s)-11,12-epoxy-15-hydroxyeicosa-5,8,13-trienoate;(5z,8z,13e)-(15s)-11,12-epoxy-15-hydroxyeicosa-5,8,13-trienoic acid;(5z,8z,13e)-(15s)-11,12-epoxy-15-hydroxyicosa-5,8,13-trienoate;(5z,8z,13e)-(15s)-11,12-epoxy-15-hydroxyicosa-5,8,13-trienoic acid;11,12-epoxy-15s-hydroxy-5z,8z,13e-eicosatrienoate;11,12-epoxy-15s-hydroxy-5z,8z,13e-eicosatrienoic acid;15-hydroxy-11,12-epoxyeicosatrienoate;15-hydroxy-11,12-epoxyeicosatrienoic acidPW_C002389111EETA13804977434331121108383123673398217411,12,15-THETAHMDB000468411,12,15-trihydroxyeicosatrienoic acid (11,12,15-THETA) is a metabolite of the 15-lipoxygenase (15-LO) pathway of arachidonic acid (AA). 11,12,15-THETA is an endothelium-derived relaxing factor. Acetylcholine stimulates AA release from membrane phospholipids of vascular endothelial cells (ECs). AA is released from phosphatidylcholine (PC) and phosphatidylethanolamine (PE) by phospholipase A2 (PLA2), or from phosphatidylinositol (PI) by phospholipase C (PLC) pathway. The diacylglycerol (DAG) lipase can convert DAG into 2-arachidonoylglycerol from which free AA can be released by monoacylglycerol (MAG) lipase or fatty acid amidohydrolase (FAAH). 11,12,15-THETA mediates the acetylcholine-induced vaso-relaxation, via activation of the K+ channels to hyperpolarize the smooth muscle membrane and induce relaxation. (PMID: 12907422, 16024567, 15388505, 14622984).C147821195404310128338CCCCC[C@H](O)\C=C\C(O)C(O)C\C=C/C\C=C/CCCC(O)=OC20H34O5InChI=1S/C20H34O5/c1-2-3-9-12-17(21)15-16-19(23)18(22)13-10-7-5-4-6-8-11-14-20(24)25/h4,6-7,10,15-19,21-23H,2-3,5,8-9,11-14H2,1H3,(H,24,25)/b6-4-,10-7-,16-15+/t17-,18?,19?/m0/s1PRMWQIVYOYCJQC-YZSNCDGGSA-N(5Z,8Z,13E,15S)-11,12,15-trihydroxyicosa-5,8,13-trienoic acid354.481354.240624198-3.834(5Z,8Z,13E,15S)-11,12,15-trihydroxyicosa-5,8,13-trienoic acid0-1FDB02340311,12,15-trihetre;11,12,15-trihydroxyicosatrienoate;11,12,15-trihydroxyicosatrienoic acid;11,12,15s-trihydroxy-5z,8z,13e-eicosatrienoate;11,12,15s-trihydroxy-5z,8z,13e-eicosatrienoic acid;(5z,8z,13e)-(15s)-11,12,15-trihydroxyeicosa-5,8,12-trienoic acid;(5z,8z,13e)-(15s)-11,12,15-trihydroxyicosa-5,8,12-trienoic acid;(5z,8z,13e,15s)-11,12,15-trihydroxyicosa-5,8,13-trienoate;(5z,8z,13e)-(15s)-11,12,15-trihydroxyeicosa-5,8,12-trienoate;(5z,8z,13e)-(15s)-11,12,15-trihydroxyicosa-5,8,12-trienoatePW_C0021741215THA13814977435331121109383123674398217216(R)-HETEHMDB000468016(R)-HETE is a metabolite of arachidonic acid, metabolized by the enzyme Cytochrome P450, family 2, subfamily C [EC:1.14.13.80 1.14.13.48 1.14.13.49]. 16(R)-HETE is an endogenous lipidic inhibitor of human neutrophil inhibitor of adhesion and aggregation activity. Human polymorphonuclear leukocytes (PMNs) produce 16(R)-HETE that modulates their function. HETEs have different biological properties based on sites of production and can be stored in tissue lipids and released in response to hormonal stimuli. Eicosanoids generated during the actions of growth factors and vasoconstrictors can modulate disease processes by affecting vascular homeostasis, inflammation, cellular growth, apoptosis and oxidant stress. In lung, the presence of these eicosanoids in the pulmonary vasculature and airways, including effects on pulmonary vascular and bronchial smooth muscle tone and airway epithelial ion transport. (PMID: 16258232, 14626496, 12681244, 11123211, 14552765, 11126912).C147789548884341627827807CCCC[C@@H](O)\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=OC20H32O3InChI=1S/C20H32O3/c1-2-3-16-19(21)17-14-12-10-8-6-4-5-7-9-11-13-15-18-20(22)23/h4-5,8-11,14,17,19,21H,2-3,6-7,12-13,15-16,18H2,1H3,(H,22,23)/b5-4-,10-8-,11-9-,17-14-/t19-/m1/s1JEKNPVYFNMZRJG-STHMYGMFSA-N(5Z,8Z,11Z,14Z,16R)-16-hydroxyicosa-5,8,11,14-tetraenoic acid320.4663320.23514489-5.21216R-hete0-1FDB02340116-hete;16r-hete;16r-hydroxy-5z,8z,11z,14z-eicosatetraenoate;16r-hydroxy-5z,8z,11z,14z-eicosatetraenoic acid;(16r,5z,8z,11z,14z)-16-hydroxy-5,8,11,14-eicosatetraenoic acid;(5z,8z,11z,14z)-(16r)-16-hydroxyeicosa-5,8,11,14-tetraenoic acid;(5z,8z,11z,14z)-(16r)-16-hydroxyicosa-5,8,11,14-tetraenoic acid;(5z,8z,11z,14z,16r)-16-hydroxyeicosa-5,8,11,14-tetraenoic acid;(all-cis)-16(r)-hydroxy-5,8,11,14-eicosatetraenoic acid;(all-z)-16(r)-hydroxy-5,8,11,14-eicosatetraenoic acid;16(r)-hydroxy-all-cis-5,8,11,14-eicosatetraenoic acid;16(r)-hydroxyeicosa-5(z),8(z),11(z),14(z)-tetraenoic acid;(16r,5z,8z,11z,14z)-16-hydroxy-5,8,11,14-eicosatetraenoate;(5z,8z,11z,14z,16r)-16-hydroxyicosa-5,8,11,14-tetraenoate;(5z,8z,11z,14z)-(16r)-16-hydroxyeicosa-5,8,11,14-tetraenoate;(5z,8z,11z,14z)-(16r)-16-hydroxyicosa-5,8,11,14-tetraenoate;(5z,8z,11z,14z,16r)-16-hydroxyeicosa-5,8,11,14-tetraenoate;(all-cis)-16(r)-hydroxy-5,8,11,14-eicosatetraenoate;(all-z)-16(r)-hydroxy-5,8,11,14-eicosatetraenoate;16(r)-hydroxy-all-cis-5,8,11,14-eicosatetraenoate;16(r)-hydroxyeicosa-5(z),8(z),11(z),14(z)-tetraenoatePW_C00217216-Hete13824977436331121110383123675398211314,15-Epoxy-5,8,11-eicosatrienoic acidHMDB000426414,15-epoxy-5,8,11-eicosatrienoic acid is an epoxyeicosatrienoic acid (EET), a metabolite of arachidonic acid. The P450 eicosanoids epoxyeicosatrienoic acids (EETs) are endogenous lipid mediators produced by P450 epoxygenases and metabolized through multiple pathways including soluble epoxide hydrolase (sEH). The cytochrome P-450 (P450) monooxygenase pathway includes enzymes of the CYP1A, CYP2B, CYP2C, CYP2E, and CYP2J subfamilies that catalyze the formation of four regioisomeric products, 5,6-, 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid. EETs are produced in brain and perform important biological functions, including protection from ischemic injury. Both light flashes and direct glial stimulation produce vasodilatation mediated by EETs. EETs may be involved in the development of hypertension and endothelial dysfunction in DOCA-salt rats, but not in excessive collagen deposition or electrophysiological abnormalities. EETs have vasodilator and natriuretic effect. Blockade of EET formation is associated with salt-sensitive hypertension. Four regioisomeric cis-EET are primary products of arachidonic acid metabolism by cytochrome P450 epoxygenases. Upon hydration by soluble epoxide hydrolase (sEH), EET are metabolized to dihydroxyeicosatrienoic acids (DHET). These hydration products are more stable and less biologically active than EETs. (PMID: 17494091, 17468203, 17434916, 17406062, 17361113, 15581597).81276-03-1C147715283205341574446326CCCCCC1OC1C\C=C/C\C=C/C\C=C/CCCC(O)=OC20H32O3InChI=1S/C20H32O3/c1-2-3-12-15-18-19(23-18)16-13-10-8-6-4-5-7-9-11-14-17-20(21)22/h4,6-7,9-10,13,18-19H,2-3,5,8,11-12,14-17H2,1H3,(H,21,22)/b6-4-,9-7-,13-10-JBSCUHKPLGKXKH-ILYOTBPNSA-N(5Z,8Z,11Z)-13-(3-pentyloxiran-2-yl)trideca-5,8,11-trienoic acid320.4663320.23514489-6.00114,15-epoxyeicosatrienoic acid0-1FDB023356(+/-)14,15-epetre;(5z,8z,11z)-14,15-epoxyeicosa-5.8.11-trienoate;(5z,8z,11z)-14,15-epoxyeicosa-5.8.11-trienoic acid;(5z,8z,11z)-14,15-epoxyicosa-5.8.11-trienoate;(5z,8z,11z)-14,15-epoxyicosa-5.8.11-trienoic acid;14(15)-epetre;14(15)-epetre-ea;14,15-eet;14,15-epetre;14,15-epoxy-5z,8z,11z-eicosatrienoate;14,15-epoxy-5z,8z,11z-eicosatrienoic acid;14,15-epoxy-5z,8z,11z-icosatrienoic acid;All-cis-14,15-epoxyeicosa-5,8,11-trienoic acidPW_C00211311E581E13834977437331121111383123676398152914,15-DiHETrEHMDB000226514,15-DiHETrE is a Cytochrome P450 (P450) eicosanoid. Eicosanoids generated from arachidonic acid metabolism by cytochrome P450 (P450) enzymes are important autocrine and paracrine factors that have diverse biological functions. P450 eicosanoids are involved in the regulation of vascular tone, renal tubular transport, cardiac contractility, cellular proliferation, and inflammation. Regulation of P450 eicosanoid levels is determined by many factors, including the induction or repression of the P450 enzymes responsible for their formation. Fibrate drugs are part of a diverse group of compounds known as peroxisome proliferators, which also include herbicides and phthalate ester plasticizers. Peroxisome proliferators act via peroxisome proliferator-activated receptor (PPAR ). This receptor is a member of the PPAR nuclear receptor family that also consists of the PPAR and PPAR isoforms. PPAR is mainly expressed in the heart, liver, and kidney, whereas the expression of PPAR is predominantly in the adipose tissue. The biological role of PPAR as a lipid sensor has been well established. 14,15-DiHETrE is a potent activators of PPAR and PPAR, shown to induce the binding of PPAR to a peroxisome proliferator response element (PPRE). Furthermore, 14,15-DiHETrE behaves like peroxisome proliferators in that is able to alter apoA-I and apoA-II mRNA expression. 14,15-DiHETrE is the most potent PPARalpha activator in a COS-7 cell expression system producing a 12-fold increase in PPARalpha-mediated luciferase activity. (PMID: 17431031, 16113065).77667-09-5C147755283147639664446271CCCCCC(O)C(O)C\C=C/C\C=C/C\C=C/CCCC(O)=OC20H34O4InChI=1S/C20H34O4/c1-2-3-12-15-18(21)19(22)16-13-10-8-6-4-5-7-9-11-14-17-20(23)24/h4,6-7,9-10,13,18-19,21-22H,2-3,5,8,11-12,14-17H2,1H3,(H,23,24)/b6-4-,9-7-,13-10-SYAWGTIVOGUZMM-ILYOTBPNSA-N(5Z,8Z,11Z)-14,15-dihydroxyicosa-5,8,11-trienoic acid338.4816338.245709576-4.39314,15-DiHETrE0-1FDB022935(+/-)14,15-dihetre;(5z,8z,11z)-14,15-dihydroxyeicosa-5,8,11-trienoate;(5z,8z,11z)-14,15-dihydroxyeicosa-5,8,11-trienoic acid;(5z,8z,11z)-14,15-dihydroxyicosa-5,8,11-trienoate;(5z,8z,11z)-14,15-dihydroxyicosa-5,8,11-trienoic acid;14,15-dhet;14,15-dihydroxy-5z,8z,11z-eicosatrienoate;14,15-dihydroxy-5z,8z,11z-eicosatrienoic acid;14,15-dihydroxyeicosatrienoate;14,15-dihydroxyeicosatrienoic acidPW_C00152914,15DH1385877438111121112122123678135423MagnesiumHMDB0000547Magnesium salts are essential in nutrition, being required for the activity of many enzymes, especially those concerned with oxidative phosphorylation. Physiologically, it exists as an ion in the body. It is a component of both intra- and extracellular fluids and is excreted in the urine and feces. Deficiency causes irritability of the nervous system with tetany, vasodilatation, convulsions, tremors, depression, and psychotic behavior. Magnesium ion in large amounts is an ionic laxative, and magnesium sulfate (Epsom salts) is sometimes used for this purpose. So-called "milk of magnesia" is a water suspension of one of the few insoluble magnesium compounds, magnesium hydroxide; the undissolved particles give rise to its appearance and name. Milk of magnesia is a mild base, and is commonly used as an antacid.22537-22-0C003058881842013-HYDROXY-MAGNESIUM-PROTOPORP865DB01378[Mg++]MgInChI=1S/Mg/q+2JLVVSXFLKOJNIY-UHFFFAOYSA-Nmagnesium(2+) ion24.30523.9850418980magnesium(2+) ion22FDB003518Magnesium;Magnesium ions;Magnesium ion;Magnesium, doubly charged positive ion;Magnesium, ion (mg(2+));Mg(2+);Mg2+PW_C000423Mg2+86822742681647627272681158191888322936399833992211167461483491529431764142124102411592942233126293373745403147749148695449745652531045329111535611253761035906147593415160381556094161625016664841786594164688116069791997170205719420672272137233211725021473102167313198747322211763132118432101231222512324249125132881258122612729290152752851533730877137133772363297793733678393334784173357848911578522331785363567857413080020368800451848004837280623118806541358086515809652538184151938323839490027108596223110559390115687398119974406120070122120247382120702407120981408121181124121265429121319419121924125122086405122408422122759120122921399123307119123546374123835464123889455124477136124637376124978375125447297125598484125669479125777481125921482125947299125973495126000490126243478126553491126753300127125389127164501127380502127407388127451507127804209128125508128347395140773891217011,12-Epoxyeicosatrienoic acidHMDB000467311,12-Epoxyeicosatrienoic acid is an epoxyeicosatrienoic acid (EET). Induction of CYP2C8 in native coronary artery endothelial cells by beta-naphthoflavone enhances the formation of 11,12-epoxyeicosatrienoic acid, as well as endothelium-derived hyperpolarizing factor-mediated hyperpolarization and relaxation. Transfection of coronary arteries with CYP2C8 antisense oligonucleotides resulted in decreased levels of CYP2C and attenuated the endothelium-derived hyperpolarizing factor-mediated vascular responses. Thus, a CYP-epoxygenase product is an essential component of the endothelium-derived hyperpolarizing factor-mediated relaxation in the porcine coronary artery, and CYP2C8 fulfills the criteria for the coronary endothelium-derived hyperpolarization factor synthase. The role of EETs in regulation of the cerebral circulation has become more important, since it was realized that EETs are produced in another specialized cell type of the brain, the astrocytes. It has become evident that EETs released from astrocytes may mediate cerebral functional hyperemia. Molecular and pharmacological evidence hve shown that neurotransmitter release and spillover onto astrocytes can generate EETs. Since these EETs may reach the vasculature via astrocyte foot-processes, they have the same potential as their endothelial counterparts to hyperpolarize and dilate cerebral vessels. P450 enzymes contain heme in their catalytic domain and nitric oxide (NO) appears to bind to these heme moieties and block formation of P450 products, including EETs. Thus, there appears to be crosstalk between P450 enzymes and NO/NO synthase. The role of fatty acid metabolites and cerebral blood flow becomes even more complex in light of data demonstrating that cyclooxygenase products can act as substrates for P450 enzymes. (PMID: 17494091, 17468203, 17434916, 17406062, 17361113, 15581597, 11413051, 10519554).81276-02-0C1477053532694510033CCCCC\C=C/C[C@H]1O[C@H]1C\C=C/C\C=C/CCCC(O)=OC20H32O3InChI=1S/C20H32O3/c1-2-3-4-5-9-12-15-18-19(23-18)16-13-10-7-6-8-11-14-17-20(21)22/h6,8-10,12-13,18-19H,2-5,7,11,14-17H2,1H3,(H,21,22)/b8-6-,12-9-,13-10-/t18-,19+/m1/s1DXOYQVHGIODESM-LZXKBWHHSA-N(5Z,8Z)-10-[(2S,3R)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl]deca-5,8-dienoic acid320.473320.23514489-5.991(5Z,8Z)-10-[(2S,3R)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl]deca-5,8-dienoic acid0-1FDB023399(5z,8z,14z)-11,12-epoxyeicosa-5,8,14-trienoate;(5z,8z,14z)-11,12-epoxyeicosa-5,8,14-trienoic acid;(5z,8z,14z)-11,12-epoxyicosa-5,8,14-trienoate;(5z,8z,14z)-11,12-epoxyicosa-5,8,14-trienoic acid;10-(3-(2-octenyl)oxiranyl)-5,8-decadienoate;10-(3-(2-octenyl)oxiranyl)-5,8-decadienoic acid;11,12-eet;11,12-epoxy-(5z,8z,14z)-eicosatrienoate;11,12-epoxy-(5z,8z,14z)-eicosatrienoic acid;11,12-epoxy-5,8,14-eicosatrienoate;11,12-epoxy-5,8,14-eicosatrienoic acid;11,12-epoxyeicosatrienoate;11,12-epoxyeicosatrienoic acid;11,12-oxido-5,8,14-eicosatrienoate;11,12-oxido-5,8,14-eicosatrienoic acidPW_C00217011EpcA13874977439331121114383123680398156211,12-DiHETrEHMDB000231411,12-DiHETrE is a Cytochrome P450 (P450) eicosanoid. Arachidonic acid may be oxygenated by cytochrome P450 in several ways. Epoxidation of the double bonds leads to the regio- and enantioselective formation of four epoxyeicosatrienoic acids (EETs), which are hydrolyzed by epoxide hydrolase to vicinal diols (DHETs). 11,12-DiHETrE excretion is increased in healthy pregnant women compared with nonpregnant female volunteers, and increased even further in patients with pregnancy-induced hypertension (PIH). The physiological significance of arachidonic acid epoxides has been debated and it is unknown whether they play a role in pregnancy and parturition. Vasodilative effects, inhibition of cyclooxygenase, or inhibition of platelet aggregation by EETs have been observed only at micromolar concentrations. On the other hand, effects on the stimulus-secretion coupling during hormone release have been found in the nanomolar and picomolar range. (PMID: 9440131, 2198572).192461-95-3C147745283146639694446270CCCCC\C=C/CC(O)C(O)C\C=C/C\C=C/CCCC(O)=OC20H34O4InChI=1S/C20H34O4/c1-2-3-4-5-9-12-15-18(21)19(22)16-13-10-7-6-8-11-14-17-20(23)24/h6,8-10,12-13,18-19,21-22H,2-5,7,11,14-17H2,1H3,(H,23,24)/b8-6-,12-9-,13-10-LRPPQRCHCPFBPE-KROJNAHFSA-N(5Z,8Z,14Z)-11,12-dihydroxyicosa-5,8,14-trienoic acid338.4816338.245709576-4.41311,12-DiHETrE0-1FDB022961(+/-)-11,12-dihydroxy-5z,8z,14z,17z-eicosatetraenoate;(+/-)-11,12-dihydroxy-5z,8z,14z,17z-eicosatetraenoic acid;(5z,8z,14z)-11,12-dihydroxyeicosa-5,8,14-trienoate;(5z,8z,14z)-11,12-dihydroxyeicosa-5,8,14-trienoic acid;(5z,8z,14z)-11,12-dihydroxyicosa-5,8,14-trienoate;(5z,8z,14z)-11,12-dihydroxyicosa-5,8,14-trienoic acid;11,12-dhet;11,12-dihydroxy-5z,8z,14z-eicosatrienoate;11,12-dihydroxy-5z,8z,14z-eicosatrienoic acid;11,12-dihydroxyeicosatrienoate;11,12-dihydroxyeicosatrienoic acid;12-dihydroxyicosa-5,8,14-trienoate;12-dihydroxyicosa-5,8,14-trienoic acid;(+/-)11,12-dihetre;11,12-dihetrePW_C00156211,12DH138887744011112111512212368113567745-HPETEHMDB00111355-HPETE, also known as 5(S)-hpete, belongs to the class of organic compounds known as hydroperoxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroperoxyl group and four CC double bonds. Thus, 5-hpete is considered to be an eicosanoid lipid molecule. 5-HPETE is considered to be a practically insoluble (in water) and relatively neutral molecule. 5-HPETE has been primarily detected in urine. Within the cell, 5-hpete is primarily located in the membrane (predicted from logP) and cytoplasm. In humans, 5-hpete is involved in the salicylate-sodium action pathway, the lornoxicam action pathway, the bromfenac action pathway, and the suprofen action pathway. 5-HPETE is also involved in a couple of metabolic disorders, which include the tiaprofenic Acid action pathway and leukotriene C4 synthesis deficiency. Arachidonic acid 5-hydroperoxide (5-hydroperoxyeicosatetraenoic acid, 5-HPETE) is an intermediate in the production of leukotriene A4 from arachidonic acid.74581-83-2C05356 52831714446295CCCCC\C=C/C\C=C/C\C=C/C=C/C(CCCC(O)=O)OOC20H32O4InChI=1S/C20H32O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(24-23)17-15-18-20(21)22/h6-7,9-10,12-14,16,19,23H,2-5,8,11,15,17-18H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-14+JNUUNUQHXIOFDA-XTDASVJISA-N(6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoic acid336.4657336.230059512-5.322(6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoic acid0-1C05356 (5s,6e,8z,11z,14z)-5-hydroperoxyicosa-6,8,11,14-tetraenoate;(5s,6e,8z,11z,14z)-5-hydroperoxyicosa-6,8,11,14-tetraenoic acid;(6e,8z,11z,14z)-(5s)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate;(6e,8z,11z,14z)-(5s)-5-hydroperoxyeicosa-6,8,11,14-tetraenoic acid;5(s)-hpete;5(s)-hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoate;5(s)-hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoic acidPW_C0067745-HPETE1389877441111121116122123682135353CalciumHMDB0000464Calcium is essential for the normal growth and maintenance of bones and teeth, and calcium requirements must be met throughout life. Requirements are greatest during periods of growth, such as childhood, during pregnancy and when breast-feeding. Long-term calcium deficiency can lead to osteoporosis, in which the bone deteriorates and there is an increased risk of fractures. Adults need between 1,000 and 1,300 mg of calcium in their daily diet. Calcium is essential for living organisms, particularly in cell physiology, and is the most common metal in many animals. Physiologically, it exists as an ion in the body. Calcium combines with phosphorus to form calcium phosphate in the bones and teeth. It is essential for the normal functioning of nerves and muscles and plays a role in blood coagulation (as factor IV) and in many enzymatic processes. Calcium is an important component of a healthy diet. A deficit can affect bone and tooth formation, while overretention can cause kidney stones. Vitamin D is needed to absorb calcium. Dairy products, such as milk and cheese, are a well-known source of calcium. However, some individuals are allergic to dairy products and even more people, particularly those of non-European descent, are lactose-intolerant, leaving them unable to consume dairy products. Fortunately, many other good sources of calcium exist. These include: seaweeds such as kelp, wakame and hijiki; nuts and seeds (like almonds and sesame); beans; amaranth; collard greens; okra; rutabaga; broccoli; kale; and fortified products such as orange juice and soy milk. Calcium has also been found to assist in the production of lymphatic fluids.14127-61-8C0007627129108CA%2b2266DB01373[Ca++]CaInChI=1S/Ca/q+2BHPQYMZQTOCNFJ-UHFFFAOYSA-Ncalcium(2+) ion40.07839.9625911550calcium(2+) ion22FDB003513Ca;Calcium element;Ca(2+);Ca2+;Calcium ion;Calcium, doubly charged positive ionPW_C000353Ca2+276163038553146012941159932199735104631163461164471478491491421552432116582138172796182937931597131607239422941866647821048222853401115780101717920572322117258160728119011774213118371981184221012198164122152851528815115350308693361773893317760011578154132782663567852634578724130789081148041374805892288182651120220122120465405121049124121300418121377419121850383121923125122370409122895135123099376123613118123870454123936455124403398124476136124924137125571297125711478125981489126009299126050490126533495127203209127434506127460388127502507128105390140676790140677834140695501814Prostaglandin G2HMDB0003235Prostaglandin G2 (PGG2) is synthesized from arachidonic acid on a cyclooxygenase (COX) metabolic pathway as a primary step; the COX biosynthesis of prostaglandin (PG) begins with the highly specific oxygenation of arachidonic acid in the 11R configuration and ends with a 15S oxygenation to form PGG2. The COX site activity that catalyzes the conversion of arachidonic acid to PGG2 is the target for nonsteroidal antiinflammatory drugs (NSAIDs). The peroxidase site activity catalyzes the two-electron reduction of the hydroperoxide bond of PGG2 to yield the corresponding alcohol prostaglandin H2 (PGH2). The formation of a phenoxyl radical on Tyr385 couples the activities of the two sites. The Tyr385 radical is produced via oxidation by compound I, an oxoferryl porphyrin -cation radical, which is generated by reaction of the hemin resting state with PGG2 or other hydroperoxides. The tyrosyl radical homolytically abstracts the 13proS hydrogen atom of arachidonic acid which initiates a radical cascade that ends with the stereoselective formation of PGG2. PGG2 then migrates from the cyclooxygenase (COX) site to the peroxidase (POX) site where it reacts with the hemin group to generate PGH2 and compound I. The heterolytic oxygen-oxygen bond cleavage is assisted by the conserved distal residues His207 and Gln203, mutation of which has been shown to severely impair enzyme activity. Compound I, upon reaction with Tyr385, gives compound II, which in turn is reduced to the hemin resting state by one-electron oxidation of reducing cosubstrates or undergoes reactions that result in enzyme self-inactivation. Prostaglandin endoperoxide H synthase (PGHS) 1 is a bifunctional membrane enzyme of the endoplasmic reticulum that converts arachidonic acid into prostaglandin H2 (PGH2), the precursor of all prostaglandins, thromboxanes, and prostacyclins. These lipid mediators are intricately involved in normal physiology, namely, in mitogenesis, fever generation, pain response, lymphocyte chemotaxis, fertility, and contradictory stimuli such as vasoconstriction and vasodilatation, as well as platelet aggregation and quiescence. PGHS is implicated in numerous pathologies, including inflammation, cancers of the colon, lung, and breast, Alzheimer's disease, Parkinson's disease, and numerous cardiovascular diseases including atherosclerosis, thrombosis, myocardial infarction, and stroke. (PMID: 14594816, 16552393, 16411757). 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.51982-36-6C059565280883276474444406DB03866[H][C@@](CCCCC)(OO)\C=C\[C@@]1([H])[C@@]2([H])C[C@]([H])(OO2)[C@]1([H])C\C=C/CCCC(O)=OC20H32O6InChI=1S/C20H32O6/c1-2-3-6-9-15(24-23)12-13-17-16(18-14-19(17)26-25-18)10-7-4-5-8-11-20(21)22/h4,7,12-13,15-19,23H,2-3,5-6,8-11,14H2,1H3,(H,21,22)/b7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1SGUKUZOVHSFKPH-YNNPMVKQSA-N(5Z)-7-[(1R,4S,5R,6R)-6-[(1E,3S)-3-hydroperoxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hept-5-enoic acid368.4645368.219888756-4.152prostaglandin G20-1FDB023127(5z)-7-{(1r,4s,5r,6r)-6-[(1e,3s)-3-hydroperoxyoct-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-hydroperoxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]hept-5-yl}hept-5-enoic acid;9,11-epidioxy-15-hydroperoxy-prosta-5,13-dien-1-oate;9,11-epidioxy-15-hydroperoxy-prosta-5,13-dien-1-oic acid;9s,11r-epidioxy-15s-hydroperoxy-5z,13e-prostadienoate;9s,11r-epidioxy-15s-hydroperoxy-5z,13e-prostadienoic acid;Endoperoxide g2;Pgg2PW_C001814PGG22461660721391497744233112111738312368439815118,9-Epoxyeicosatrienoic acidHMDB00022328,9-Epoxyeicosatrienoic acid is an epoxyeicosatrienoic acid eicosanoid, a metabolite of arachidonic acid. The P450 epoxyeicosatrienoic acids (EETs) are endogenous lipid mediators produced by P450 epoxygenases and metabolized through multiple pathways including soluble epoxide hydrolase (sEH). The cytochrome P-450 (P450) monooxygenase pathway includes enzymes of the CYP1A, CYP2B, CYP2C, CYP2E, and CYP2J subfamilies that catalyze the formation of four regioisomeric products, 5,6-, 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid. EETs are produced in brain and perform important biological functions, including protection from ischemic injury. Both light flashes and direct glial stimulation produce vasodilatation mediated by EETs. EETs may be involved in the development of hypertension and endothelial dysfunction in DOCA-salt rats, but not in excessive collagen deposition or electrophysiological abnormalities. EETs have vasodilator and natriuretic effect. Blockade of EET formation is associated with salt-sensitive hypertension. Four regioisomeric cis-EET are primary products of arachidonic acid metabolism by cytochrome P450 epoxygenases. Upon hydration by soluble epoxide hydrolase (sEH), EET are metabolized to dihydroxyeicosatrienoic acids (DHET). These hydration products are more stable and less biologically active than EETs. (PMID: 17494091, 17468203, 17434916, 17406062, 17361113, 15581597).81246-85-7C147695283203344904446324CCCCC\C=C/C\C=C/CC1OC1C\C=C/CCCC(O)=OC20H32O3InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-12-15-18-19(23-18)16-13-10-11-14-17-20(21)22/h6-7,9-10,12-13,18-19H,2-5,8,11,14-17H2,1H3,(H,21,22)/b7-6-,12-9-,13-10-DBWQSCSXHFNTMO-TYAUOURKSA-N(5Z)-7-{3-[(2Z,5Z)-undeca-2,5-dien-1-yl]oxiran-2-yl}hept-5-enoic acid320.4663320.23514489-6.0018,9-epoxyeicosatrienoic acid0-1FDB022920(+/-)8,9-epetre;(5z,11z,14z)-8,9-epoxyeicosa-5,11,14-trienoate;(5z,11z,14z)-8,9-epoxyeicosa-5,11,14-trienoic acid;(5z,11z,14z)-8,9-epoxyicosa-5,11,14-trienoate;(5z,11z,14z)-8,9-epoxyicosa-5,11,14-trienoic acid;8,9-eet;8,9-epoxy-5z,11z,14z-eicosatrienoate;8,9-epoxy-5z,11z,14z-eicosatrienoic acid;8,9-epoxyeicosatrienoate;8,9-epoxyeicosatrienoic acid;8,9-epoxy-5z,11z,14z-icosatrienoic acid;8,9-epoxyicosatrienoic acidPW_C00151189EEsta1393497744333112112038312368739815618,9-DiHETrEHMDB00023118,9-DiHETrE is a Cytochrome P450 (P450) eicosanoid. Eicosanoids generated from arachidonic acid (AA) metabolism by cytochrome P450 (P450) enzymes are important autocrine and paracrine factors that have diverse biological functions. P450 eicosanoids are involved in the regulation of vascular tone, renal tubular transport, cardiac contractility, cellular proliferation, and inflammation. P450converts AA to 8,9- dihydroxyeicosatrienoic acid. This enzymatic pathway was first described in liver; however, it is now clear that AA can be metabolized by P450 in many tissues including the pituitary gland, eye, kidney, adrenal gland, and blood vessels. (PMID: 17431031, 11700990).192461-96-4C147735283144639704446268CCCCC\C=C/C\C=C/CC(O)C(O)C\C=C/CCCC(O)=OC20H34O4InChI=1S/C20H34O4/c1-2-3-4-5-6-7-8-9-12-15-18(21)19(22)16-13-10-11-14-17-20(23)24/h6-7,9-10,12-13,18-19,21-22H,2-5,8,11,14-17H2,1H3,(H,23,24)/b7-6-,12-9-,13-10-DCJBINATHQHPKO-TYAUOURKSA-N(5Z,11Z,14Z)-8,9-dihydroxyicosa-5,11,14-trienoic acid338.4816338.245709576-4.4338,9-DiHETrE0-1FDB022960(+/-)8,9-dihetre;(5z,11z,14z)-8,9-dihydroxyeicosa-5,11,14-trienoate;(5z,11z,14z)-8,9-dihydroxyeicosa-5,11,14-trienoic acid;(5z,11z,14z)-8,9-dihydroxyicosa-5,11,14-trienoate;(5z,11z,14z)-8,9-dihydroxyicosa-5,11,14-trienoic acid;8,9-dhet;8,9-dihydroxy-5z,11z,14z-eicosatrienoate;8,9-dihydroxy-5z,11z,14z-eicosatrienoic acid;8,9-dihydroxyeicosatrienoate;8,9-dihydroxyeicosatrienoic acid;8,9-dihetre;8,9-dihydroxy-5z,11z,14z-icosatrienoic acidPW_C00156189DHET139487744411112112112212368813514775,6-Epoxy-8,11,14-eicosatrienoic acidHMDB00021905,6-Epoxy-8,11,14-eicosatrienoic acid is an Epoxyeicosatrienoic acid (EET), a metabolite of arachidonic acid. The epoxyeicosatrienoic acids (EETs) are endogenous lipid mediators produced by P450 epoxygenases and metabolized through multiple pathways including soluble epoxide hydrolase (sEH). The cytochrome P-450 (P450) monooxygenase pathway includes enzymes of the CYP1A, CYP2B, CYP2C, CYP2E, and CYP2J subfamilies that catalyze the formation of four regioisomeric products, 5,6-, 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid. EETs are produced in brain and perform important biological functions, including protection from ischemic injury. Both light flashes and direct glial stimulation produce vasodilatation mediated by EETs. EETs may be involved in the development of hypertension and endothelial dysfunction in DOCA-salt rats, but not in excessive collagen deposition or electrophysiological abnormalities. EETs have vasodilator and natriuretic effect. Blockade of EET formation is associated with salt-sensitive hypertension. (PMID: 17494091, 17468203, 17434916, 17406062, 17361113).81246-84-6C147685283202344504446323CCCCC\C=C/C\C=C/C\C=C/CC1OC1CCCC(O)=OC20H32O3InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-15-18-19(23-18)16-14-17-20(21)22/h6-7,9-10,12-13,18-19H,2-5,8,11,14-17H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-VBQNSZQZRAGRIX-QNEBEIHSSA-N4-{3-[(2Z,5Z,8Z)-tetradeca-2,5,8-trien-1-yl]oxiran-2-yl}butanoic acid320.4663320.23514489-5.9915(6)epoxyeicosatrienoic acid0-1FDB022895(+/-)5,6-epetre;(8z,11z,14z)-5,6-epoxyeicosa-8,11,14-trienoate;(8z,11z,14z)-5,6-epoxyeicosa-8,11,14-trienoic acid;(8z,11z,14z)-5,6-epoxyicosa-8,11,14-trienoate;(8z,11z,14z)-5,6-epoxyicosa-8,11,14-trienoic acid;5,6-eet;5,6-epetre;5,6-epoxy-8z,11z,14z-eicosatrienoate;5,6-epoxy-8z,11z,14z-eicosatrienoic acid;5,6-epoxy-8,11,14-eicosatrienoic acid;5,6-epoxy-8,11,14-icosatrienoic acid;5,6-epoxy-8z,11z,14z-icosatrienoic acidPW_C00147756EEsta1395497744533112112238312368939815795,6-DHETHMDB00023435,6-DHET is an epoxide intermediate in the oxygenation of arachidonic acid by hepatic monooxygenases pathway. 5,6-DHET is the hydrolysis metabolite of cis-5(6)Epoxy-cis-8,11,14-eicosatrienoic acid by epoxide hydrolases. Many drugs, chemicals, and endogenous compounds are oxygenated in mammalian tissues and in some instances reactive and potentially toxic or carcinogenic epoxides are formed. Naturally occurring olefins may also be oxygenated by mammalian enzymes. The most well known are lipoxygenases and microsomal cytochrome P-450-linked monooxygenases. The epoxides may be chemically labile or may be enzymatically hydrolyzed. When arene or olefinic epoxides are formed by microsomal P-450-linked monooxygenases, they are often rapidly converted to less reactive trans-diols through the action of microsomal epoxide hydrolases. (PMID: 6801052, 6548162).213382-49-1C147725283142639744446266CCCCC\C=C/C\C=C/C\C=C/CC(O)C(O)CCCC(O)=OC20H34O4InChI=1S/C20H34O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-15-18(21)19(22)16-14-17-20(23)24/h6-7,9-10,12-13,18-19,21-22H,2-5,8,11,14-17H2,1H3,(H,23,24)/b7-6-,10-9-,13-12-GFNYAPAJUNPMGH-QNEBEIHSSA-N(8Z,11Z,14Z)-5,6-dihydroxyicosa-8,11,14-trienoic acid338.4816338.245709576-4.4035,6-DiHETrE0-1FDB022971(+/-)5,6-dihetre;(8z,11z,14z)-5,6-dihydroxyeicosa-8,11,14-trienoate;(8z,11z,14z)-5,6-dihydroxyeicosa-8,11,14-trienoic acid;(8z,11z,14z)-5,6-dihydroxyicosa-8,11,14-trienoate;(8z,11z,14z)-5,6-dihydroxyicosa-8,11,14-trienoic acid;5,6-dhet;5,6-dihetre;5,6-dihydroxy-8z,11z,14z-eicosatrienoate;5,6-dihydroxy-8z,11z,14z-eicosatrienoic acid;5,6-dihydroxy-8z,11z,14z-icosatrienoic acidPW_C00157956DHET139687744611112112312212369013521838(S)-HPETEHMDB00046998S-HPETE is metabolized from arachidonic acid by the enzyme 8S-lipoxygenase (8-LOX in mouse, ALOX15 and ALOX15B in human). 8S-HPETE will be readily reduced under physiological circumstances to 8S-hydroxyeicosatetraenoic acid (8S-HETE), a natural agonist of peroxisome proliferator-activated receptor alpha (PPAR alpha). (PMID: 16112079).C148239548880344877827803CCCCC\C=C/C\C=C/C=C/[C@H](C\C=C/CCCC(O)=O)OOC20H32O4InChI=1S/C20H32O4/c1-2-3-4-5-6-7-8-9-10-13-16-19(24-23)17-14-11-12-15-18-20(21)22/h6-7,9-11,13-14,16,19,23H,2-5,8,12,15,17-18H2,1H3,(H,21,22)/b7-6-,10-9-,14-11-,16-13+/t19-/m1/s1QQUFCXFFOZDXLA-VYOQERLCSA-N(5Z,8S,9E,11Z,14Z)-8-hydroperoxyicosa-5,9,11,14-tetraenoic acid336.4657336.230059512-5.3028S-HpETE0-1FDB0234128-peroxy-5z,9e,11z,14z-eicosatetraenoate;8-peroxy-5z,9e,11z,14z-eicosatetraenoic acid;8s-hpete;8s-hydoperoxy-5z,9e,11z,14z-eicosatetraenoate;8s-hydoperoxy-5z,9e,11z,14z-eicosatetraenoic acid;(5z,9e,11z,14z)-(8s)-8-hydroperoxyeicosa-5,9,11,14-tetraenoic acid;(5z,9e,11z,14z)-(8s)-8-hydroperoxyicosa-5,9,11,14-tetraenoic acid;(5z,9e,11z,14z)-(8s)-8-hydroperoxyeicosa-5,9,11,14-tetraenoate;(5z,8s,9e,11z,14z)-8-hydroperoxyicosa-5,9,11,14-tetraenoate;(5z,9e,11z,14z)-(8s)-8-hydroperoxyicosa-5,9,11,14-tetraenoatePW_C0021838SHPETE1399877447111121124122123691135677519(S)-HETEHMDB001113619(S)-HETE, also known as 19-hete, belongs to the class of organic compounds known as hydroxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroxyl group and four CC double bonds. Thus, 19(S)-hete is considered to be an eicosanoid lipid molecule. 19(S)-HETE is considered to be a practically insoluble (in water) and relatively neutral molecule. 19(S)-HETE has been primarily detected in urine. Within the cell, 19(S)-hete is primarily located in the membrane (predicted from logP) and cytoplasm. In humans, 19(S)-hete is involved in the tenoxicam action pathway, the trisalicylate-choline action pathway, the ketoprofen action pathway, and the ketorolac action pathway. 19(S)-HETE is also involved in a couple of metabolic disorders, which include the tiaprofenic Acid action pathway and leukotriene C4 synthesis deficiency. 19(S)-HETE is an intermediate in Arachidonic acid metabolism. 19(S)-HETE is converted from Arachidonic acid via the enzyme CYP2U and Unspecific. Monooxygenase. (EC:1.14.14.1).79551-85-2C147499548883341857827806C[C@H](O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=OC20H32O3InChI=1S/C20H32O3/c1-19(21)17-15-13-11-9-7-5-3-2-4-6-8-10-12-14-16-18-20(22)23/h3-6,9-12,19,21H,2,7-8,13-18H2,1H3,(H,22,23)/b5-3-,6-4-,11-9-,12-10-/t19-/m0/s1XFUXZHQUWPFWPR-DZBJBCEBSA-N(5Z,8Z,11Z,14Z,19S)-19-hydroxyicosa-5,8,11,14-tetraenoic acid320.4663320.23514489-5.25219S-hete0-1C14749(19s)-hydroxy arachidonic acid;(19s)-hydroxyeicosatetraenoate;(19s)-hydroxyeicosatetraenoic acid;(19s)-hydroxyicosatetraenoate;(19s)-hydroxyicosatetraenoic acid;19(s)-hete;(19s,5z,8z,11z,14z)-19-hydroxy-5,8,11,14-eicosatetraenoic acid;(5z,8z,11z,14z)-(19s)-19-hydroxyeicosa-5,8,11,14-tetraenoic acid;(5z,8z,11z,14z,19s)-19-hydroxyeicosa-5,8,11,14-tetraenoic acid;(5z,8z,11z,14z,19s)-19-hydroxyicosa-5,8,11,14-tetraenoic acid;19(s)-hydroxy-all-cis-5,8,11,14-eicosatetraenoic acid;19(s)-hydroxyeicosa-5(z),8(z),11(z),14(z)-tetraenoic acid;(19s)-hydroxy arachidonate;(19s,5z,8z,11z,14z)-19-hydroxy-5,8,11,14-eicosatetraenoate;(5z,8z,11z,14z)-(19s)-19-hydroxyeicosa-5,8,11,14-tetraenoate;(5z,8z,11z,14z,19s)-19-hydroxyeicosa-5,8,11,14-tetraenoate;(5z,8z,11z,14z,19s)-19-hydroxyicosa-5,8,11,14-tetraenoate;19(s)-hydroxy-all-cis-5,8,11,14-eicosatetraenoate;19(s)-hydroxyeicosa-5(z),8(z),11(z),14(z)-tetraenoatePW_C00677519SHETE14164977448331121125383123693398217912(R)-HPETEHMDB000469212(R)-HPETE is a hydroperoxyeicosatetraenoic acid eicosanoid derived from arachidonic acid. The epidermal lipoxygenases 12R-LOX and eLOX3 act in sequence to convert arachidonic acid via 12(R)-HPETE to 12(R)-HETE and the corresponding epoxyalcohol, 8(R)-hydroxy-11(R),12(R)-epoxyeicosatrienoic acid. The epidermal lipoxygenases 12R-LOX and eLOX3 are the gene products of ALOX12B and ALOXE3. Mutations in ALOXE3 or ALOX12B have been found in families with autosomal-recessive congenital ichthyosis (ARCI). ARCI is a clinically and genetically heterogeneous group of severe hereditary keratinization disorders characterized by intense scaling of the whole integument, and differences in color and shape, often associated with erythema. Mutations in ALOXE3 and ALOX12B on chromosome 17p13, which code for two different epidermal lipoxygenases, were found in patients with ichthyosiform erythroderma. Genetic studies indicated that 12R-lipoxygenase (12R-LOX) or epidermal lipoxygenase-3 (eLOX3) was mutated in six families affected by non-bullous congenital ichthyosiform erythroderma (NCIE), one of the main clinical forms of ichthyosis. (PMID: 16116617, 15629692).126873-49-2C148129548885341457827808CCCCC\C=C/C[C@@H](OO)\C=C\C=C/C\C=C/CCCC(O)=OC20H32O4InChI=1S/C20H32O4/c1-2-3-4-5-10-13-16-19(24-23)17-14-11-8-6-7-9-12-15-18-20(21)22/h7-11,13-14,17,19,23H,2-6,12,15-16,18H2,1H3,(H,21,22)/b9-7-,11-8-,13-10-,17-14+/t19-/m1/s1ZIOZYRSDNLNNNJ-ZYBDYUKJSA-N(5Z,8Z,10E,12R,14Z)-12-hydroperoxyicosa-5,8,10,14-tetraenoic acid336.4657336.230059512-5.30212R-HpETE0-1FDB02340812r-hpete;12r-hydroperoxy-5z,8z,10e,14z-eicosatetraenoate;12r-hydroperoxy-5z,8z,10e,14z-eicosatetraenoic acid;12r-hydroperoxyeicosatetraenoate;12r-hydroperoxyeicosatetraenoic acid;(5z,8z,10e,14z)-(12r)-12-hydroperoxyeicosa-5,8,10,14-tetraenoic acid;(5z,8z,10e,14z)-(12r)-12-hydroperoxyicosa-5,8,10,14-tetraenoic acid;(5z,8z,10e,14z)-(12r)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate;(5z,8z,10e,12r,14z)-12-hydroperoxyicosa-5,8,10,14-tetraenoate;(5z,8z,10e,14z)-(12r)-12-hydroperoxyicosa-5,8,10,14-tetraenoatePW_C00217912RHPET1419497744933112112638312369539821718-HETEHMDB00046798(S)-HETE is a naturally occurring hydroxyeicosatetraenoic acid eicosanoid. 8(S)-HETE is a strong activator of peroxisome proliferator-activated receptors (PPARs) alpha and a weak activator of PPAR gamma. PPARs are nuclear hormone receptors that regulate gene transcription in response to peroxisome proliferators and fatty acids. PPARs also play an important role in the regulation of adipocyte differentiation. It is unclear however what naturally occurring compounds activate each of the PPAR subtypes. Additionally, 8(S)-HETE is able to induce differentiation of preadipocytes. (PMID: 7592593, 9113987).98462-03-4C147765283154344864446278CCCCC\C=C/C\C=C/C=C/[C@@H](O)C\C=C/CCCC(O)=OC20H32O3InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-10-13-16-19(21)17-14-11-12-15-18-20(22)23/h6-7,9-11,13-14,16,19,21H,2-5,8,12,15,17-18H2,1H3,(H,22,23)/b7-6-,10-9-,14-11-,16-13+/t19-/m1/s1NLUNAYAEIJYXRB-VYOQERLCSA-N(5Z,8S,9E,11Z,14Z)-8-hydroxyicosa-5,9,11,14-tetraenoic acid320.4663320.23514489-5.2928(S)-hete0-1FDB023400(5z,8s,9e,11z,14z)-8-hydroxyicosa-5,9,11,14-tetraenoate;(5z,8s,9e,11z,14z)-8-hydroxyicosa-5,9,11,14-tetraenoic acid;8(s)-hydroxy-(5z,9e,11z,14z)-eicosatetraenoate;8(s)-hydroxy-(5z,9e,11z,14z)-eicosatetraenoic acid;8s-hete;8s-hydroxy-5z,9e,11z,14z-eicosatetraenoate;8s-hydroxy-5z,9e,11z,14z-eicosatetraenoic acid;(5z,8s,9e,11z,14z)-8-hydroxyeicosa-5,9,11,14-tetraenoic acid;(5z,9e,11z,14z)-(8s)-8-hydroxyeicosa-5,9,11,14-tetraenoic acid;(5z,9e,11z,14z)-(8s)-8-hydroxyicosa-5,9,11,14-tetraenoic acid;(8s)-hydroxy-(5z),(9e),(11z),(14z)-eicosatetraenoic acid;(s)-(z,e,z,z)-8-hydroxyeicosa-5,9,11,14-tetraenoic acid;8(s)-hydroxyeicosatetraenoic acid;(5z,8s,9e,11z,14z)-8-hydroxyeicosa-5,9,11,14-tetraenoate;(5z,9e,11z,14z)-(8s)-8-hydroxyeicosa-5,9,11,14-tetraenoate;(5z,9e,11z,14z)-(8s)-8-hydroxyicosa-5,9,11,14-tetraenoate;(8s)-hydroxy-(5z),(9e),(11z),(14z)-eicosatetraenoate;(s)-(z,e,z,z)-8-hydroxyeicosa-5,9,11,14-tetraenoate;8(s)-hydroxyeicosatetraenoatePW_C0021718-HETE1429187745113012112912512369813621638-IsoprostaneHMDB00046598-isoprostane concentrations are elevated in asthma and increase with the clinical severity and during acute asthma episodes. Isoprostane is formed in the airways of asthmatic patients from peroxidation of poly-unsaturated fatty acids in cell membranes, the effect of reactive oxygen species resulting of the NADPH oxidase of eosinophils, neutrophils and alveolar macrophages, which produces superoxide anion which undergoes dismutation to H2O2. (PMID 16354413). 8-isoprostane is also elevated in Bronchopulmonary dysplasia, which remains an important cause of morbidity and mortality in extremely premature newborn infants receiving intensive care and is the most common contributing factor to severe respiratory morbidity and mortality in early childhood. (PMID 14980283). 8-Isoprostaglandin F(2a) is a marker of oxidative stress in the aqueous humour of patients with exfoliation syndrome (XFS) (PubMed ID 12598453).155976-51-5C138091078733302397008[H][C@@]1(CCCCCCC)CCC[C@]1([H])CCCCCCCCC20H40InChI=1S/C20H40/c1-3-5-7-9-11-13-16-20-18-14-17-19(20)15-12-10-8-6-4-2/h19-20H,3-18H2,1-2H3/t19-,20+/m1/s1UKVVPDHLUHAJNZ-UXHICEINSA-N(1R,2S)-1-heptyl-2-octylcyclopentane280.5316280.31300128-7.5608β-prostane00FDB0233928-isoprostane;8-beta-prostane;(8beta)-prostane;(8b)-prostane;(8β)-prostanePW_C0021638-Isop14341877452130121130125123699136261420-Hydroxyeicosatetraenoic acidHMDB000599820-Hydroxyeicosatetraenoic acid (20-HETE) is a metabolite of arachidonic acid. Cytochrome P450 enzymes of the 4A and 4F families catalyze the omega-hydroxylation of arachidonic acid and produce 20-HETE. 20-HETE is a potent constrictor of renal, cerebral, and mesenteric arteries. The vasoconstrictor response to 20-HETE is associated with activation of protein kinase, Rho kinase, and the mitogen-activated protein (MAP) kinase pathway C. 20-HETE also increases intracellular Ca2+ by causing the depolarization of vascular smooth muscle membrane secondary to blocking the large-conductance Ca2+-activated K+-channels and by a direct effect on L-type Ca channels. Elevations in the production of 20-HETE mediate the myogenic response of skeletal, renal, and cerebral arteries to elevations in transmural pressure. There is an important interaction between nitric oxide (NO) and the formation of 20-HETE production. NO inhibits the formation of 20-HETE formation in renal and cerebral arteries. A fall in levels of 20-HETE contributes to the cyclic GMP-independent dilator effect of NO to activate the large-conductance Ca2+-activated K+-channels and to dilate the cerebral arteries (PMID: 16258232).79551-86-3C147485283157343064446281OCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=OC20H32O3InChI=1S/C20H32O3/c21-19-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18-20(22)23/h1,3-4,6-7,9-10,12,21H,2,5,8,11,13-19H2,(H,22,23)/b3-1-,6-4-,9-7-,12-10-NNDIXBJHNLFJJP-DTLRTWKJSA-N(5Z,8Z,11Z,14Z)-20-hydroxyicosa-5,8,11,14-tetraenoic acid320.4663320.23514489-5.43220-hete0-1FDB023796(5z,8z,11z,14z)-20-hydroxyicosa-5,8,11,14-tetraenoate;(5z,8z,11z,14z)-20-hydroxyicosa-5,8,11,14-tetraenoic acid;(all-z)-20-hydroxy-5,8,11,14-eicosatetraenoate;(all-z)-20-hydroxy-5,8,11,14-eicosatetraenoic acid;20-hete;20-hydroxy arachidonic acid;20-hydroxy-(5z,8z,11z,14z)-eicosatetraenoate;20-hydroxy-(5z,8z,11z,14z)-eicosatetraenoic acid;20-hydroxy-5,8,11,14-eicosatetraenoate;20-hydroxy-5,8,11,14-eicosatetraenoic acid;20-hydroxy-5z,8z,11z,14z-eicosatetraenoate;20-hydroxy-5z,8z,11z,14z-eicosatetraenoic acid;20-hydroxyarachidonic acid;20-hydroxyicosatetraenoate;20-hydroxyicosatetraenoic acid;20-hydroxyeicosatetraenoic acid;20-hydroxy arachidonate;20-hydroxyarachidonate;20-hydroxyeicosatetraenoatePW_C00261420-HETE14384977453331121133383123702398210512(S)-HPETEHMDB000424312-HPETE is one of the six monohydroperoxy fatty acids produced by the non-enzymatic oxidation of arachidonic acid (Leukotrienes). Reduction of the hydroperoxide yields the more stable hydroxyl fatty acid (+/-)12-HETE. A family of biologically active compounds derived from arachidonic acid by oxidative metabolism through the 5-lipoxygenase pathway. They participate in host defense reactions and pathophysiological conditions such as immediate hypersensitivity and inflammation. They have potent actions on many essential organs and systems, including the cardiovascular, pulmonary, and central nervous system as well as the gastrointestinal tract and the immune system.67675-13-2C059655280892156264444415CCCCC\C=C/C[C@H](OO)\C=C\C=C/C\C=C/CCCC(O)=OC20H32O4InChI=1S/C20H32O4/c1-2-3-4-5-10-13-16-19(24-23)17-14-11-8-6-7-9-12-15-18-20(21)22/h7-11,13-14,17,19,23H,2-6,12,15-16,18H2,1H3,(H,21,22)/b9-7-,11-8-,13-10-,17-14+/t19-/m0/s1ZIOZYRSDNLNNNJ-LQWMCKPYSA-N(5Z,8Z,10E,12S,14Z)-12-hydroperoxyicosa-5,8,10,14-tetraenoic acid336.4657336.230059512-5.30212-HpETE0-1FDB023348(5z,8z,10e,14z)-(12s)-12-hydroperoxyicosa-5,8,10,14-tetraenoate;(5z,8z,10e,14z)-(12s)-12-hydroperoxyicosa-5,8,10,14-tetraenoic acid;12-hpete;12-hydroperoxyeicosatetraenoate;12-hydroperoxyeicosatetraenoic acid;12-hydroperoxyicosatetraenoate;12-hydroperoxyicosatetraenoic acid;(5z,8z,10e,14z)-(12s)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate;12-oohete;Arachidonic acid omega-9 hydroperoxide;Omega-9 hpaa;Omega-9-hydroperoxyarachidonic acid;(5z,8z,10e,14z)-(12s)-12-hydroperoxyeicosa-5,8,10,14-tetraenoic acid;(5z,8z,10e,12s,14z)-12-hydroperoxyicosa-5,8,10,14-tetraenoate;Arachidonate omega-9 hydroperoxide;Omega-9-hydroperoxyarachidonatePW_C00210512SHPET13978774541111211351221237041354045312(R)-HETEHMDB006111912R-Hete, also known as 12-R-hete, belongs to the class of organic compounds known as hydroxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroxyl group and four CC double bonds. Thus, 12R-hete is considered to be an eicosanoid lipid molecule. 12R-Hete is considered to be a practically insoluble (in water) and relatively neutral molecule.C148225283156341444446280CCCCC\C=C/C[C@@H](O)\C=C\C=C/C\C=C/CCCC(O)=OC20H32O3InChI=1S/C20H32O3/c1-2-3-4-5-10-13-16-19(21)17-14-11-8-6-7-9-12-15-18-20(22)23/h7-11,13-14,17,19,21H,2-6,12,15-16,18H2,1H3,(H,22,23)/b9-7-,11-8-,13-10-,17-14+/t19-/m1/s1ZNHVWPKMFKADKW-ZYBDYUKJSA-N(5Z,8Z,10E,12R,14Z)-12-hydroxyicosa-5,8,10,14-tetraenoic acid320.4663320.23514489-5.26212R-hete0-1(5z,8z,10e,12r,14z)-12-hydroxy-5,8,10,14-eicosatetraenoic acid;(5z,8z,10e,12r,14z)-12-hydroxyeicosa-5,8,10,14-tetraenoic acid;(5z,8z,10e,14z)-(12r)-12-hydroxyeicosa-5,8,10,14-tetraenoic acid;(5z,8z,10e,14z)-(12r)-12-hydroxyicosa-5,8,10,14-tetraenoic acid;12(r)-hydroxy-5(z),8(z),10(e),14(z)-eicosatetraenoic acid;12(r)-hydroxy-5,8,14-cis-10-trans-eicosatetraenoic acid;12(r)-hydroxyeicosatetraenoic acid;12r-hete;(5z,8z,10e,12r,14z)-12-hydroxy-5,8,10,14-eicosatetraenoate;(5z,8z,10e,12r,14z)-12-hydroxyeicosa-5,8,10,14-tetraenoate;(5z,8z,10e,14z)-(12r)-12-hydroxyeicosa-5,8,10,14-tetraenoate;(5z,8z,10e,14z)-(12r)-12-hydroxyicosa-5,8,10,14-tetraenoate;12(r)-hydroxy-5(z),8(z),10(e),14(z)-eicosatetraenoate;12(r)-hydroxy-5,8,14-cis-10-trans-eicosatetraenoate;12(r)-hydroxyeicosatetraenoatePW_C04045312RHETE14411877455130121136125123706136852412-KETEHMDB001363312-keto-eicosatetraenoic acid is a biologically active eicosanoid in the nervous system of Aplysia.It is a metabolite of 12-HPETE formed by Aplysia nervous tissue. 12-KETE was identified in incubations of the tissue with arachidonic acid using HPLC, UV spectrometry, and gas-chromatography/mass spectrometry. [3H]12-KETE is formed from endogenous lipid stores in nervous tissue, labeled with [3H]arachidonic acid upon stimulation by application of histamine. In L14 and L10 cells, identified neurons in the abdominal ganglion, applications of 12-KETE elicit changes in membrane potential similar to those evoked by histamine.[PMID:2774398].108437-64-5C148075283162341514446286CCCCC\C=C/CC(=O)\C=C\C=C/C\C=C/CCCC(O)=OC20H30O3InChI=1S/C20H30O3/c1-2-3-4-5-10-13-16-19(21)17-14-11-8-6-7-9-12-15-18-20(22)23/h7-11,13-14,17H,2-6,12,15-16,18H2,1H3,(H,22,23)/b9-7-,11-8-,13-10-,17-14+GURBRQGDZZKITB-VXBMJZGYSA-N(5Z,8Z,10E,14Z)-12-oxoicosa-5,8,10,14-tetraenoic acid318.4504318.219494826-5.62112-oxo-ETE0-1C14807(5z,8z,10e,14z)-12-oxoeicosa-5,8,10,14-tetraenoate;(5z,8z,10e,14z)-12-oxoeicosa-5,8,10,14-tetraenoic acid;(5z,8z,10e,14z)-12-oxoicosa-5,8,10,14-tetraenoate;(5z,8z,10e,14z)-12-oxoicosa-5,8,10,14-tetraenoic acid;12-oxo-ete;12-oxoete;12-kete;12-keto-ete;12-ketoeicosatetraenoic acid;12-oxo, 5c,8c,10t,14c-20:4;12-ketoeicosatetraenoatePW_C00852412-KETE144218774561301211371251237071364045212(S)-HETEHMDB006111812S-Hete belongs to the class of organic compounds known as hydroxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroxyl group and four CC double bonds. Thus, 12S-hete is considered to be an eicosanoid lipid molecule. 12S-Hete is considered to be a practically insoluble (in water) and relatively neutral molecule.54397-83-0C147775283155341464446279CCCCC\C=C/C[C@H](O)\C=C\C=C/C\C=C/CCCC(O)=OC20H32O3InChI=1S/C20H32O3/c1-2-3-4-5-10-13-16-19(21)17-14-11-8-6-7-9-12-15-18-20(22)23/h7-11,13-14,17,19,21H,2-6,12,15-16,18H2,1H3,(H,22,23)/b9-7-,11-8-,13-10-,17-14+/t19-/m0/s1ZNHVWPKMFKADKW-LQWMCKPYSA-N(5Z,8Z,10E,12S,14Z)-12-hydroxyicosa-5,8,10,14-tetraenoic acid320.4663320.23514489-5.26212S-hete0-1(12s)-12-hydroxy-5,8,14-cis-10-trans-eicosatetraenoic acid;(5z,8z,10e,12s,14z)-12-hydroxyeicosa-5,8,10,14-tetraenoic acid;(5z,8z,10e,14z)-(12s)-12-hydroxyeicosa-5,8,10,14-tetraenoic acid;(5z,8z,10e,14z)-(12s)-12-hydroxyicosa-5,8,10,14-tetraenoic acid;12(s)-hydroxy-5(z),8(z),10(e),14(z)-eicosatetraenoic acid;12(s)-hydroxy-5,8,14(z),10(e)-eicosatetraenoic acid;12(s)-hydroxyeicosatetraenoic acid;12s-hete;(12s)-12-hydroxy-5,8,14-cis-10-trans-eicosatetraenoate;(5z,8z,10e,12s,14z)-12-hydroxyeicosa-5,8,10,14-tetraenoate;(5z,8z,10e,14z)-(12s)-12-hydroxyeicosa-5,8,10,14-tetraenoate;(5z,8z,10e,14z)-(12s)-12-hydroxyicosa-5,8,10,14-tetraenoate;12(s)-hydroxy-5(z),8(z),10(e),14(z)-eicosatetraenoate;12(s)-hydroxy-5,8,14(z),10(e)-eicosatetraenoate;12(s)-hydroxyeicosatetraenoatePW_C04045212SHETE144318774571301211381251237081363933PC(14:0/20:4(5Z,8Z,11Z,14Z))HMDB0007883PC(14:0/20:4(5Z,8Z,11Z,14Z)) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(14:0/20:4(5Z,8Z,11Z,14Z)), in particular, consists of one chain of myristic acid at the C-1 position and one chain of arachidonic acid at the C-2 position. The myristic acid moiety is derived from nutmeg and butter, while the arachidonic acid moiety is derived from animal fats and eggs. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC.C0015724778634 PHOSPHATIDYLCHOLINE24766559CCCCCCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCCC42H76NO8PInChI=1S/C42H76NO8P/c1-6-8-10-12-14-16-18-19-20-21-22-23-25-27-29-31-33-35-42(45)51-40(39-50-52(46,47)49-37-36-43(3,4)5)38-48-41(44)34-32-30-28-26-24-17-15-13-11-9-7-2/h14,16,19-20,22-23,27,29,40H,6-13,15,17-18,21,24-26,28,30-39H2,1-5H3/b16-14-,20-19-,23-22-,29-27-/t40-/m1/s1SRQSAJRUMDQMMS-NLDJLLEISA-N(2-{[(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-3-(tetradecanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium754.0285753.530854925-7.400lecithin00FDB0250751-myristoyl-2-arachidonoyl-sn-glycero-3-phosphocholine;Gpcho(14:0/20:4);Gpcho(14:0/20:4n6);Gpcho(14:0/20:4w6);Gpcho(34:4);Lecithin;Pc aa c34:4;Pc(14:0/20:4);Pc(14:0/20:4n6);Pc(14:0/20:4w6);Pc(34:4);Phosphatidylcholine(14:0/20:4);Phosphatidylcholine(14:0/20:4n6);Phosphatidylcholine(14:0/20:4w6);Phosphatidylcholine(34:4)PW_C003933PC142041444815532491553330922173187745811189470361894713311052553861052563831162004011162013981211391221237091356388LysoPC(14:0/0:0)HMDB0010379LysoPC(14:0/0:0) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. Lysophosphatidylcholines can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) position. Fatty acids containing 16, 18 and 20 carbons are the most common. LysoPC(14:0/0:0), in particular, consists of one chain of myristic acid at the C-1 position. The myristic acid moiety is derived from nutmeg and butter. Lysophosphatidylcholine is found in small amounts in most tissues. It is formed by hydrolysis of phosphatidylcholine by the enzyme phospholipase A2, as part of the de-acylation/re-acylation cycle that controls its overall molecular species composition. It can also be formed inadvertently during extraction of lipids from tissues if the phospholipase is activated by careless handling. In blood plasma significant amounts of lysophosphatidylcholine are formed by a specific enzyme system, lecithin:cholesterol acyltransferase (LCAT), which is secreted from the liver. The enzyme catalyzes the transfer of the fatty acids of position sn-2 of phosphatidylcholine to the free cholesterol in plasma, with formation of cholesterol esters and lysophosphatidylcholine. Lysophospholipids have a role in lipid signaling by acting on lysophospholipid receptors (LPL-R). LPL-R's are members of the G protein-coupled receptor family of integral membrane proteins.20559-16-4C0423046060464489 PHOSPHATIDYLCHOLINE405289CCCCCCCCCCCCCC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)CC22H46NO7PInChI=1S/C22H46NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-22(25)28-19-21(24)20-30-31(26,27)29-18-17-23(2,3)4/h21,24H,5-20H2,1-4H3/t21-/m1/s1VXUOFDJKYGDUJI-OAQYLSRUSA-N(2-{[(2R)-2-hydroxy-3-(tetradecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium467.5769467.301189343-5.841(2-{[(2R)-2-hydroxy-3-(tetradecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium00C042301-myristoyl-glycero-3-phosphocholine;Lpc(14:0);Lpc(14:0/0:0);Lypc(14:0);Lypc(14:0/0:0);Lysopc(14:0);Lysopc(14:0/0:0);Lysophosphatidylcholine(14:0);Lysophosphatidylcholine(14:0/0:0);Lysopc a c14:0;1-tetradecanoyl-sn-glycero-3-phosphocholine;Pc(14:0/0:0)PW_C006388LPC14:01445875011907502188750816377459111121140122123710135407092,3-Dinor-8iso prostaglandin F1αHMDB00613775-[(1S,2R)-3,5-Dihydroxy-2-[(1E)-3-hydroxyoct-1-en-1-yl]cyclopentyl]pentanoic acid 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. 5-[(1S,2R)-3,5-Dihydroxy-2-[(1E)-3-hydroxyoct-1-en-1-yl]cyclopentyl]pentanoic acid is considered to be a practically insoluble (in water) and relatively neutral molecule.1739579334229CCCCCC(O)\C=C\[C@H]1C(O)CC(O)[C@H]1CCCCC(O)=OC18H32O5InChI=1S/C18H32O5/c1-2-3-4-7-13(19)10-11-15-14(16(20)12-17(15)21)8-5-6-9-18(22)23/h10-11,13-17,19-21H,2-9,12H2,1H3,(H,22,23)/b11-10+/t13?,14-,15+,16?,17?/m0/s1XHHYJZGDOMKLEE-GYKMFVPESA-N5-[(1S,2R)-3,5-dihydroxy-2-[(1E)-3-hydroxyoct-1-en-1-yl]cyclopentyl]pentanoic acid328.4437328.224974134-2.8245-[(1S,2R)-3,5-dihydroxy-2-[(1E)-3-hydroxyoct-1-en-1-yl]cyclopentyl]pentanoic acid0-1PW_C040709DisPF1a47161877462130121143125123715136407082,3-Dinor-8iso prostaglandin F2αHMDB00613785-[(1S,2R)-3,5-Dihydroxy-2-[(1E)-3-hydroxyoct-1-en-1-yl]cyclopentyl]pentanoic acid 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. 5-[(1S,2R)-3,5-Dihydroxy-2-[(1E)-3-hydroxyoct-1-en-1-yl]cyclopentyl]pentanoic acid is considered to be a practically insoluble (in water) and relatively neutral molecule.173957923423021467087CCCCCC(O)\C=C\[C@H]1C(O)CC(O)[C@H]1C\C=C/CC(O)=OC18H30O5InChI=1S/C18H30O5/c1-2-3-4-7-13(19)10-11-15-14(16(20)12-17(15)21)8-5-6-9-18(22)23/h5-6,10-11,13-17,19-21H,2-4,7-9,12H2,1H3,(H,22,23)/b6-5-,11-10+/t13?,14-,15+,16?,17?/m0/s1IDKLJIUIJUVJNR-NEGVKCBZSA-N(3Z)-5-[(1S,2R)-3,5-dihydroxy-2-[(1E)-3-hydroxyoct-1-en-1-yl]cyclopentyl]pent-3-enoic acid326.4278326.20932407-2.974(3Z)-5-[(1S,2R)-3,5-dihydroxy-2-[(1E)-3-hydroxyoct-1-en-1-yl]cyclopentyl]pent-3-enoic acid0-1PW_C040708DisPF2a47171877463130121144125123716136951Leukotriene-B(4) omega-hydroxylase 1P78329Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
HMDBP01013CYP4F219p13.12BC06743911.14.13.194; 1.14.13.-; 1.14.13.30133310953Leukotriene A-4 hydrolaseP09960Epoxide hydrolase that catalyzes the final step in the biosynthesis of the proinflammatory mediator leukotriene B4. Has also aminopeptidase activity.
HMDBP01015LTA4H12q22CH47105413.3.2.613358752Leukotriene C4 synthaseQ16873Catalyzes the conjugation of leukotriene A4 with reduced glutathione to form leukotriene C4.
HMDBP00807LTC4S5q35U6202514.4.1.20133910691Gamma-glutamyltranspeptidase 1P19440Initiates extracellular glutathione (GSH) breakdown, provides cells with a local cysteine supply and contributes to maintain intracellular GSH level. It is part of the cell antioxidant defense mechanism. Catalyzes the transfer of the glutamyl moiety of glutathione to amino acids and dipeptide acceptors. Alternatively, glutathione can be hydrolyzed to give Cys-Gly and gamma glutamate. Isoform 3 seems to be inactive.
HMDBP00730GGT122q11.23BC06950412.3.2.2; 3.4.19.13; 3.4.19.14166142318773Glutathione peroxidase 1P07203Protects the hemoglobin in erythrocytes from oxidative breakdown.
HMDBP00828GPX13p21.3Y0048311.11.1.9189814408641062Prostacyclin synthaseQ16647Catalyzes the isomerization of prostaglandin H2 to prostacyclin (= prostaglandin I2).
HMDBP01129PTGIS20q13.13BC10180915.3.99.461221355491400178181408487141447181464Prostaglandin-H2 D-isomeraseP41222Catalyzes the conversion of PGH2 to PGD2, a prostaglandin involved in smooth muscle contraction/relaxation and a potent inhibitor of platelet aggregation. Involved in a variety of CNS functions, such as sedation, NREM sleep and PGE2-induced allodynia, and may have an anti-apoptotic role in oligodendrocytes. Binds small non-substrate lipophilic molecules, including biliverdin, bilirubin, retinal, retinoic acid and thyroid hormone, and may act as a scavenger for harmful hydrophopic molecules and as a secretory retinoid and thyroid hormone transporter. Possibly involved in development and maintenance of the blood-brain, blood-retina, blood-aqueous humor and blood-testis barrier. It is likely to play important roles in both maturation and maintenance of the central nervous system and male reproductive system.
HMDBP01576PTGDS9q34.2-q34.3BT01992215.3.99.261821356814084971414437814144418353Aldo-keto reductase family 1 member C3P42330Catalyzes the conversion of aldehydes and ketones to alcohols. Catalyzes the reduction of prostaglandin (PG) D2, PGH2 and phenanthrenequinone (PQ) and the oxidation of 9-alpha,11-beta-PGF2 to PGD2. Functions as a bi-directional 3-alpha-, 17-beta- and 20-alpha HSD. Can interconvert active androgens, estrogens and progestins with their cognate inactive metabolites. Preferentially transforms androstenedione (4-dione) to testosterone.
HMDBP00360AKR1C310p15-p14L4383611.-.-.-; 1.1.1.357; 1.1.1.112; 1.1.1.188; 1.1.1.239; 1.1.1.64; 1.3.1.20620213588495731141445181471Thromboxane-A synthaseP24557HMDBP01583TBXAS17q34-q35L3607815.3.99.525116622213604914001681814085371414461876Prostaglandin E synthaseO14684Catalyzes the oxidoreduction of prostaglandin endoperoxide H2 (PGH2) to prostaglandin E2 (PGE2).
HMDBP00079PTGES9q34.3AJ27180315.3.99.3615213634914009881408527141448185706Prostamide/prostaglandin F synthaseQ8TBF2AF42526611.11.1.201365872Carbonyl reductase [NADPH] 1P16152NADPH-dependent reductase with broad substrate specificity. Catalyzes the reduction of a wide variety of carbonyl compounds including quinones, prostaglandins, menadione, plus various xenobiotics. Catalyzes the reduction of the antitumor anthracyclines doxorubicin and daunorubicin to the cardiotoxic compounds doxorubicinol and daunorubicinol. Can convert prostaglandin E2 to prostaglandin F2-alpha. Can bind glutathione, which explains its higher affinity for glutathione-conjugated substrates. Catalyzes the reduction of S-nitrosoglutathione.
HMDBP00075CBR121q22.13BC01564011.1.1.184; 1.1.1.197; 1.1.1.189136681954249553114334826143372973915Arachidonate 15-lipoxygenaseP16050Converts arachidonic acid to 15S-hydroperoxyeicosatetraenoic acid. Also acts on C-12 of arachidonate as well as on linoleic acid.
HMDBP00977ALOX1517p13.3AK29030911.13.11.33; 1.13.11.31137381450Cytochrome P450 2C8P10632Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
HMDBP01562CYP2C810q23.33AK29332811.14.14.113784933592938051040092648091848151813991530013992029814021331141044691410738471427629731441Cytochrome P450 2B6P20813Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
HMDBP01553CYP2B619q13.2M2987411.14.13.-1384493270233572934231434341045801813656836140212311402173921409608471426829731428839961609Bifunctional epoxide hydrolase 2P34913Bifunctional enzyme. The C-terminal domain has epoxide hydrolase activity and acts on epoxides (alkene oxides, oxiranes) and arene oxides. Plays a role in xenobiotic metabolism by degrading potentially toxic epoxides. Also determines steady-state levels of physiological mediators. The N-terminal domain has lipid phosphatase activity, with the highest activity towards threo-9,10-phosphonooxy-hydroxy-octadecanoic acid, followed by erythro-9,10-phosphonooxy-hydroxy-octadecanoic acid, 12-phosphonooxy-octadec-9Z-enoic acid, 12-phosphonooxy-octadec-9E-enoic acid, and p-nitrophenyl phospate.
HMDBP01790EPHX28p21CH47108013.3.2.10; 3.1.3.7613868910Arachidonate 5-lipoxygenaseP09917Catalyzes the first step in leukotriene biosynthesis, and thereby plays a role in inflammatory processes.
HMDBP00972ALOX510q11.2M3819111.13.11.3413908914Prostaglandin G/H synthase 1P23219May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
HMDBP00976PTGS19q32-q33.3M3181311.14.99.12481661621392491964183882962477811585881395141140014818140829714112584714258963143342931911Arachidonate 15-lipoxygenase BO15296Converts arachidonic acid exclusively to 15S-hydroperoxyeicosatetraenoic acid, while linoleic acid is less well metabolized.
HMDBP00973ALOX15B17p13.1CH47110811.13.11.33; 1.13.11.-140081432Cytochrome P450 2E1P05181
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
HMDBP01544CYP2E110q24.3-qterJ0262511.14.13.-;1.14.13.n778110141749360029396426481118481718517195136042313962736139911298139917300141119651411248471419809131427009731429149962262Arachidonate 12-lipoxygenase, 12R-typeO75342Converts arachidonic acid to 12R- hydroperoxyeicosatetraenoic acid (12R-HPETE)HMDBP03129ALOX12B17p13.1AF03846111.13.11.-1421491453Cytochrome P450 2J2P51589This enzyme metabolizes arachidonic acid predominantly via a NADPH-dependent olefin epoxidation to all four regioisomeric cis-epoxyeicosatrienoic acids. One of the predominant enzymes responsible for the epoxidation of endogenous cardiac arachidonic acid pools.
HMDBP01565CYP2J21p31.3-p31.2AY42698511.14.14.11436493854Cytochrome P450 2U1Q7Z449
Catalyzes the hydroxylation of arachidonic acid, docosahexaenoic acid and other long chain fatty acids. May modulate the arachidonic acid signaling pathway and play a role in other fatty acid signaling processes.
HMDBP08638CYP2U14q25BC13276711.14.14.1143749393Cytochrome P450 4A11Q02928Catalyzes the omega- and (omega-1)-hydroxylation of various fatty acids such as laurate, myristate and palmitate. Has little activity toward prostaglandins A1 and E1. Oxidizes arachidonic acid to 20-hydroxyeicosatetraenoic acid (20-HETE).
HMDBP00401CYP4A111p33L0475111.14.15.3143949137849713912Arachidonate 12-lipoxygenase, 12S-typeP18054Oxygenase and 14,15-leukotriene A4 synthase activity.
HMDBP00974ALOX1217p13.1AY52781711.13.11.31; 3.3.2.-139884323Cytosolic phospholipase A2 betaP0C869Calcium-dependent phospholipase A2 that selectively hydrolyzes glycerophospholipids in the sn-2 position with a preference for arachidonoyl phospholipids. Has a much weaker activity than PLA2G4A. Isoform 3 has calcium-dependent activity against palmitoyl-arachidonyl-phosphatidylethanolamine and low level lysophospholipase activity but no activity against phosphatidylcholine. Isoform 5 does have activity against phosphatidylcholine.
HMDBP09120PLA2G4B15q11.2-q21.3AC02065913.1.1.43028150914155921384312111384381601391448014094160913Prostaglandin G/H synthase 2P35354Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
HMDBP00975PTGS21q25.2-q25.3M9010011.14.99.1609218564919651838839624878659815114001581814056623140830714093948142588631433419311452Cytochrome P450 4F8P98187Hydroxylates arachidonic acid (20:4n-6) to (18R)-hydroxyarachidonate. Shows little activity against prostaglandin (PG) D2, PGE1, PGE2, PGF2alpha, and leukotriene B4. Catalyzes omega-2 and omega-3-hydroxylation of PGH1 and PGH2. Catalyzes epoxidation of 4,7,10,13,16,19-(Z)-docosahexaenoic acid (22:6n-3) and 7,10,13,16,19-(Z)-docosapentaenoic acid (22:5n-3) and omega-3-hydroxylation of 4,7,10,13,16-(Z)-docosapentaenoic acid (22:5n-6). Catalyzes hydroxylation of PGI2 and carbaprostacyclin.
HMDBP01564CYP4F819p13.1AF13329811.14.14.1144049471418952Leukotriene-B(4) omega-hydroxylase 2Q08477Cytochromes P450 are a group of heme-thiolate monooxygenases. This enzyme requires molecular oxygen and NADPH for the omega-hydroxylation of LTB4, a potent chemoattractant for polymorphonuclear leukocytes.
HMDBP01014CYP4F319p13.2AB00246111.14.13.199; 1.14.13.-; 1.14.13.30471518377Leukotriene-B(4) omega-hydroxylase 11PW_P000377399951117617991378Leukotriene A-4 hydrolase1PW_P000378400953117710051379Leukotriene C4 synthase1PW_P000379401752347Gamma-glutamyltranspeptidase 11PW_P0000474869111601426Glutathione peroxidase 11PW_P0000262777341178185Prostacyclin synthase1PW_P00018520310628317991187Prostaglandin-H2 D-isomerase1PW_P0001872051464188Aldo-keto reductase family 1 member C31PW_P00018820635365Thromboxane-A synthase 1PW_P0000657914713917991186Prostaglandin E synthase1PW_P00018620476384801380Prostamide/prostaglandin F synthase1PW_P00038040257061381Carbonyl reductase [NADPH] 11PW_P000381403721382Arachidonate 15-lipoxygenase1PW_P000382404915117881331383Cytochrome P450 2C81PW_P0003834051450117917991384Cytochrome P450 2B61PW_P0003844061441118017991385Epoxide hydratase 21PW_P000385407160921814231386Arachidonate 5-lipoxygenase1PW_P000386408910118281331183353263Prostaglandin G/H synthase 11PW_P0000637491423717991388Arachidonate 15-lipoxygenase B1PW_P000388410911118581331226Cytochrome P450 2E11PW_P0002262441432110917991389Arachidonate 12-lipoxygenase, 12R-type1PW_P0003894112262118681331390Cytochrome P450 2J21PW_P0003904121453118717991391Cytochrome P450 2U11PW_P0003914133854118817991392Cytochrome P450 4A111PW_P000392414393118917991387Arachidonate 12-lipoxygenase, 12S-type1PW_P00038740991211848133177Cytosolic phospholipase A2 beta1PW_P00007791432314335313008184Prostaglandin G/H synthase 21PW_P0001842029138217992393Cytochrome P450 4F81PW_P00039341514521190179911102Leukotriene-B(4) omega-hydroxylase 21PW_P0011021263952145917991871truePW_R000871Right353411621Compoundfalse353526441Compoundfalse872falsePW_R000872Right35368531Compoundfalse35371461Compoundtrue353810651Compoundtrue353911621Compoundfalse35401431Compoundtrue354114201Compoundtrue461377376falsePW_R000376Right155710301Compoundfalse155814201Compoundtrue15598531Compoundfalse4623783.3.2.6873truePW_R000873Right35428531Compoundfalse354320981Compoundfalse384falsePW_R000384Right158310301Compoundfalse1584801Compoundtrue15859331Compoundfalse4633794.4.1.20874falsePW_R000874Right35449331Compoundfalse354514201Compoundtrue354617751Compoundfalse3547951Compoundtrue46447875truePW_R000875Right3548404501Compoundfalse354910301Compoundfalse876truePW_R000876Right355021061Compoundfalse3551404501Compoundfalse877falsePW_R000877Right355221061Compoundfalse3553802Compoundtrue355419861Compoundfalse355518471Compoundtrue355614201Compoundtrue465261.11.1.9878truePW_R000878Right355721001Compoundfalse355823981Compoundfalse879truePW_R000879Right355917261Compoundfalse356021031Compoundfalse880truePW_R000880Right356167731Compoundfalse356262291Compoundfalse881truePW_R000881Right356316871Compoundfalse356421001Compoundfalse882truePW_R000882Right356510281Compoundfalse356617261Compoundfalse883truePW_R000883Right356710841Compoundfalse356816871Compoundfalse690falsePW_R000690Right282010681Compoundfalse282110281Compoundfalse1871855.3.99.4694falsePW_R000694Right282810681Compoundfalse282910841Compoundfalse1911875.3.99.2884falsePW_R000884Right356910841Compoundfalse35701461Compoundtrue357167761Compoundfalse35721431Compoundtrue466188533falsePW_R000533Right222610681Compoundfalse222711211Compoundfalse77655.3.99.5691falsePW_R000691Right282210681Compoundfalse28239491Compoundfalse1881865.3.99.3695falsePW_R000695Right283010681Compoundfalse28318891Compoundfalse1923801.11.1.20885falsePW_R000885Right35739491Compoundfalse35741461Compoundtrue35758891Compoundfalse35761431Compoundtrue467381886truePW_R000886Right35779491Compoundfalse357816991Compoundfalse887truePW_R000887Right357916991Compoundfalse3580404511Compoundfalse888truePW_R000888Right358111211Compoundfalse358218201Compoundfalse889truePW_R000889Right3583404511Compoundfalse358420991Compoundfalse890truePW_R000890Right358518201Compoundfalse358621041Compoundfalse378falsePW_R000378Right15638211Compoundfalse156410651Compoundtrue156521061Compoundfalse468382891falsePW_R000891Right358721061Compoundfalse358810651Compoundtrue358921801Compoundfalse359014201Compoundtrue4693831.14.14.1892falsePW_R000892Right359121801Compoundfalse359210651Compoundtrue359321811Compoundfalse359414201Compoundtrue4703831.14.14.1893falsePW_R000893Right359521061Compoundfalse359610651Compoundtrue359723891Compoundfalse359814201Compoundtrue4713831.14.14.1895falsePW_R000895Right360323891Compoundfalse360410651Compoundtrue360521741Compoundfalse360614201Compoundtrue4733831.14.14.1896falsePW_R000896Right36078211Compoundfalse360810651Compoundtrue360921721Compoundfalse361014201Compoundtrue4743831.14.14.1897falsePW_R000897Right36118211Compoundfalse361210651Compoundtrue361321131Compoundfalse361414201Compoundtrue4753841.14.13.-325falsePW_R000325Right135921131Compoundfalse136014201Compoundtrue136115291Compoundfalse476385898falsePW_R000898Right36158211Compoundfalse361610651Compoundtrue361721701Compoundfalse361814201Compoundtrue4773841.14.13.-899falsePW_R000899Right361921701Compoundfalse362014201Compoundtrue362115621Compoundfalse478385900falsePW_R000900Right362267741Compoundfalse362310651Compoundtrue362410301Compoundfalse362514201Compoundtrue4793861.13.11.34901falsePW_R000901Right36268211Compoundfalse362710651Compoundtrue362867741Compoundfalse362914201Compoundtrue4803861.13.11.34902falsePW_R000902Right3630802Compoundtrue363167741Compoundfalse363218471Compoundtrue363367731Compoundfalse363414201Compoundtrue481261.11.1.9595falsePW_R000595Right251418141Compoundfalse251510681Compoundfalse363614201Compoundtrue76631.14.99.14821841.14.99.1454falsePW_R000454Right18878211Compoundfalse188810652Compoundtrue188918141Compoundfalse73631.14.99.17381841.14.99.1903falsePW_R000903Right36378211Compoundfalse363810651Compoundtrue363915111Compoundfalse364014201Compoundtrue4843841.14.13.-326falsePW_R000326Right136215111Compoundfalse136314201Compoundtrue136415611Compoundfalse485385904falsePW_R000904Right36418211Compoundfalse364210651Compoundtrue364314771Compoundfalse364414201Compoundtrue4863841.14.13.-327falsePW_R000327Right136514771Compoundfalse136614201Compoundtrue136715791Compoundfalse487385385falsePW_R000385Right15868211Compoundfalse158710651Compoundtrue158821831Compoundfalse489388906falsePW_R000906Right36488211Compoundfalse364910651Compoundtrue365067751Compoundfalse365114201Compoundtrue4902264933901.14.14.14943911.14.14.1907falsePW_R000907Right36528211Compoundfalse365310651Compoundtrue365421791Compoundfalse4923891.13.11.-908truePW_R000908Right365521831Compoundfalse365621711Compoundfalse910truePW_R000910Right36598211Compoundfalse366021631Compoundfalse913falsePW_R000913Right36678211Compoundfalse366810651Compoundtrue366926141Compoundfalse367014201Compoundtrue4953921.14.15.34963931.14.14.14973911.14.14.1377falsePW_R000377Right15608211Compoundfalse156110651Compoundtrue156221051Compoundfalse491387909truePW_R000909Right365721791Compoundfalse3658404531Compoundfalse914truePW_R000914Right367121051Compoundfalse367285241Compoundfalse915truePW_R000915Right367321051Compoundfalse3674404521Compoundfalse916falsePW_R000916Both367539331Compoundfalse367614201Compoundtrue36778211Compoundfalse367863881Compoundfalse498773.1.1.42296falsePW_R002296Right84558211Compoundfalse84561461Compoundtrue845710651Compoundtrue845826141Compoundfalse84591431Compoundtrue846014201Compoundtrue21921102911truePW_R000911Right366321631Compoundfalse3664407091Compoundfalse912truePW_R000912Right366521631Compoundfalse3666407081Compoundfalse219711621881false415160510regular200190219826441881false415117510regular20019021998531081false413213010regular20019022001461062false358203010regular5030220110651065false599200110regular787822021431061false360185510regular5030220314201049false600183510regular787822041799109false458191519regular1002522051030881false1033213010regular20019022061420849false928229010regular78782207100589false768218010regular10025220820981081false413245510regular2001902209801081false813196010regular20019022109331081false1033159010regular20019022111420849false968146510regular787822121775881false1033106010regular200190221395881false828123510regular2001902214404501881false1033245510regular200190221521061881false1033286510regular200190221680881false868266510regular20019022171986881false418286510regular20019022181847881false593266510regular20019022191420849false643301010regular7878222021001881false1930102510regular200190222123981881false1400102510regular200190222217261881false1930132010regular200190222321031881false1400132010regular200190222467731881false1930162010regular200190222562291881false1400162010regular200190222616871881false2310102510regular200190222710281881false2310148010regular200190222810841881false2840133510regular200190222910684981false2310183510regular20019022301799499false2365171020regular100252231146862false2630130010regular503022326776881false284096010regular2001902233143861false2630114010regular5030223411214981false3235183510regular20019022351799499false2885189010regular1002522369494981false3230139510regular200190223780499false2870159010regular100252238889881false3235163010regular2001902239146862false3605151010regular50302240143861false3610167010regular5030224116991881false3230104010regular2001902242404511881false3730104010regular200190224318201881false3730164510regular200190224420991881false4085104010regular200190224521041881false4085164510regular20019022468211882false1883256210regular30028022471065865false1754257410regular78782248813389false1598265310regular10025225410654965false336318610regular7878225521804981false412352510regular200190225614204949false332339010regular787822571799499false460328020regular10025225810654965false355375610regular7878225921814981false416408010regular200190226014204949false351397010regular787822611799499false459385519regular10025226210654965false976312110regular7878226323894981false1037346510regular200190226414204949false977330510regular787822651799499false1085321019regular10025226610654965false990370110regular7878226721744981false1041402510regular200190226814204949false991389510regular787822691799499false1089380019regular10025227010654965false1581287410regular7878227121724981false1397314310regular200190227214204949false1582305810regular787822731799499false1445296819regular10025227410654965false1581345410regular7878227521134981false1397379810regular200200227614204949false1577363310regular787822771799499false1450354520regular1002522781420849false1737391810regular787822791529881false1397413310regular200190228042389false1617402519regular10025228110654965false1896290410regular7878228221704982false1887328310regular300280228314204949false1897312810regular787822841799499false1985301519regular1002522851420849false1677351310regular787822861562881false1937377810regular200190228742389false1787361019regular1002522886774881false1933212810regular20019022891065865false1789227910regular787822901420849false1543228010regular78782291813389false1648217810regular10025229235389false1648224310regular1002522931065865false1681250410regular787822941420849false1683232310regular78782295813389false1785241020regular10025229635389false1780246519regular10025229780881false1713197810regular20019022981847881false1715177010regular20019022991420849false2095183510regular7878230018144981false2310220510regular200190230114204949false2560199510regular787823021799499false2290208010regular10025230310654965false2456253410regular787823041799499false2280241610regular10025230510654965false2491341910regular7878230615114981false2312379810regular200190230714204949false2492361810regular787823081799499false2360351319regular1002523091420849false2657392810regular787823101561881false2312412810regular200190231142389false2547401319regular10025231210654965false2219298310regular787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