394PathwayRosiglitazone Metabolism PathwayRosiglitazone is an anti-diabetic drug in the thiazolidinedione class of drugs. It is extensively metabolized in the liver by the cytochrome p450 enzymes CYP2C8 and CYP2C9 to para-hydroxy rosiglitazon, ortho-hydroxy rosiglitazone and N-desmethyl rosiglitazone. N-desmethyl rosiglitazone is the major metabolite and is further metabolized to N-desmethyl-p-hydroxyrosiglitazone, N-desmethyl glucuronide rosiglitazone and N-desmethyl-O-hydroxy rosiglitazone. Both para-hydroxy rosiglitazon and ortho-hydroxy rosiglitazone are excreted as sulfated or glucuronidated metabolites.Drug MetabolismPW000629CenterPathwayVisualizationContext74220002200#000099PathwayVisualization376394Rosiglitazone PathwayRosiglitazone is an anti-diabetic drug in the thiazolidinedione class of drugs. It is extensively metabolized in the liver by the cytochrome p450 enzymes CYP2C8 and CYP2C9 to para-hydroxy rosiglitazon, ortho-hydroxy rosiglitazone and N-desmethyl rosiglitazone. N-desmethyl rosiglitazone is the major metabolite and is further metabolized to N-desmethyl-p-hydroxyrosiglitazone, N-desmethyl glucuronide rosiglitazone and N-desmethyl-O-hydroxy rosiglitazone. Both para-hydroxy rosiglitazon and ortho-hydroxy rosiglitazone are excreted as sulfated or glucuronidated metabolites.Drug11780[PharmgKB](http://www.pharmgkb.org/pathway/PA165816969)394Pathway1CellCL:00000002Platelet CL:00002334Cardiomyocyte CL:00007465HepatocyteCL:00001823NeuronCL:00005407Epithelial CellCL:00000661Homo sapiens9606EukaryoteHuman5Bos taurus9913EukaryoteCattle3Escherichia coli562Prokaryote24Solanum lycopersicum4081EukaryoteTomato18Saccharomyces cerevisiae4932EukaryoteYeast4Arabidopsis thaliana3702EukaryoteThale cress49Bathymodiolus platifrons220390EukaryoteDeep sea mussel10Drosophila melanogaster7227EukaryoteFruit fly23Pseudomonas aeruginosa287Prokaryote12Mus musculus10090EukaryoteMouse17Rattus norvegicus10116EukaryoteRat6Caenorhabditis elegans6239EukaryoteRoundworm2Bacteria2ProkaryoteBacteria21Xenopus laevis8355EukaryoteAfrican clawed frog25Escherichia coli (strain K12)83333Prokaryote60Nitzschia sp.0001EukaryoteNitzschia419Schizosaccharomyces pombe4896Eukaryote11Extracellular SpaceGO:00056155CytoplasmGO:00057376LysosomeGO:00057644PeroxisomeGO:000577713Endoplasmic ReticulumGO:000578310Cell MembraneGO:000588616Lysosomal LumenGO:00432022MitochondrionGO:00057397Endoplasmic Reticulum MembraneGO:00057891CytosolGO:00058293Mitochondrial MatrixGO:000575918Melanosome MembraneGO:003316214Mitochondrial Outer MembraneGO:000574124Mitochondrial Intermembrane SpaceGO:000575835ChloroplastGO:000950736MembraneGO:001602012Mitochondrial Inner MembraneGO:000574319sarcoplasmic reticulumGO:001652931Periplasmic SpaceGO:000562053Endoplasmic Reticulum BodyGO:001016834Plant-Type VacuoleGO:000032532Inner MembraneGO:007025825Golgi apparatusGO:000579420Endoplasmic Reticulum LumenGO:000578821SynapseGO:004520215NucleusGO:000563440PeriplasmGO:00425978Smooth Endoplasmic Reticulum GO:000579037Basolateral cell membraneGO:00163231LiverBTO:00007597292Endothelium BTO:00003934Adrenal MedullaBTO:00000497185cardiocyteBTO:000153928StomachBTO:0001307155268Blood VesselBTO:0001102741125IntestineBTO:00006487Nervous SystemBTO:000148411HeartBTO:0000562731029111PW_BS00002915111PW_BS000015311511PW_BS0000319611PW_BS0000095411PW_BS00000516212PW_BS000016181311PW_BS0000188511PW_BS00000814101PW_BS0000142811611PW_BS0000283211PW_BS000003101711PW_BS000010204111PW_BS0000204311PW_BS000004331811PW_BS0000332111PW_BS00000249711PW_BS0000492441011PW_BS000024221411PW_BS000022422411PW_BS00004213121PW_BS0000131231751PW_BS0001231251351PW_BS000125126651PW_BS00012612711651PW_BS00012710813PW_BS0001081471241PW_BS00014715924PW_BS000159188118PW_BS0000241632181PW_BS0001631601181PW_BS0001602137181PW_BS00002421013181PW_BS00002421217181PW_BS000024151141PW_BS0001512164181PW_BS0000241985181PW_BS0000242156181PW_BS0000242111018PW_BS0000242253541PW_BS0000241644PW_BS0001642863641PW_BS000024226441PW_BS0000242491341PW_BS0000242916491PW_BS0000242924491PW_BS00002429817101PW_BS00002430013101PW_BS0000243016101PW_BS000024302116101PW_BS0000242231241PW_BS000024171211PW_BS000017315123PW_BS00002429341PW_BS0000242941141PW_BS00002413412121PW_BS0001341115121PW_BS00011113013121PW_BS0001303317121PW_BS00002833217121PW_BS0000281136121PW_BS0001131151012PW_BS0001153344121PW_BS0000283361121PW_BS000028337116121PW_BS0000281122121PW_BS00011212915121PW_BS00012934141121PW_BS0000281141112PW_BS0001141333121PW_BS00013332914121PW_BS0000281321121PW_BS00013234524121PW_BS00002834318121PW_BS000028360410121PW_BS000028408451PW_BS000115122551PW_BS000122405105PW_BS000115407251PW_BS0001154141551PW_BS000115409115PW_BS000115406351PW_BS0001154151851PW_BS000115124151PW_BS000124383751PW_BS00010043441051PW_BS000115429151PW_BS0001153821451PW_BS0001004182451PW_BS0001153841251PW_BS0001003744171PW_BS0000534436171PW_BS0001151355171PW_BS0001353761017PW_BS00005344717171PW_BS00011513613171PW_BS000136448116171PW_BS0001151192171PW_BS00011945015171PW_BS0001151371117PW_BS0001371203171PW_BS00012045118171PW_BS0001151181171PW_BS0001183987171PW_BS000113469410171PW_BS0001154641171PW_BS00011539914171PW_BS00011345424171PW_BS00011512112171PW_BS0001214824101PW_BS0001154781010PW_BS0001154831110PW_BS0001152975101PW_BS0000244793101PW_BS0001154812101PW_BS0001152991101PW_BS00002448414101PW_BS0001154957101PW_BS00011548924101PW_BS00011548012101PW_BS000115502461PW_BS000115207661PW_BS000024209106PW_BS000024208116PW_BS000024205561PW_BS000024501361PW_BS0001155041861PW_BS000115206261PW_BS000024388161PW_BS00011251541061PW_BS0001153891461PW_BS0001123951361PW_BS000113390761PW_BS0001125062461PW_BS0001153911261PW_BS0001123551914PW_BS000035117131PW_BS00011717018PW_BS000170224241PW_BS000024222341PW_BS0000243221231PW_BS000024943PW_BS000094261115PW_BS000026541315PW_BS0000547028511PW_BS000070103331PW_BS000103107313PW_BS000107100521PW_BS000100105113PW_BS0001051553241PW_BS0001551572241PW_BS0001571613181PW_BS00016116611PW_BS0001661783211PW_BS00017815284PW_BS000152101531PW_BS0001011873118PW_BS000024219314PW_BS00002422014PW_BS00002416212181PW_BS0001621951318PW_BS0000242811251PW_BS0000242851041PW_BS0000242875341PW_BS0000242273441PW_BS0000243081011PW_BS0000243183123PW_BS0000243125231PW_BS0000243201123PW_BS00002432711125PW_BS00002834713125PW_BS0000283683601PW_BS000028310312PW_BS00002430412PW_BS000024109323PW_BS0001094241155PW_BS0001154251355PW_BS00011545911175PW_BS00011546013175PW_BS000115432511PW_BS00004360251PW_BS00006046114PW_BS00004672513PW_BS000072612517PW_BS0000613612011PW_BS0000363772113PW_BS00003793252011PW_BS00009327151PW_BS000027711PW_BS000007971521PW_BS000097110231PW_BS0001106131PW_BS000006140103PW_BS00014014315191PW_BS0001431465191PW_BS000146951721PW_BS00009511PW_BS0000011802211PW_BS00018021425181PW_BS0000241901118PW_BS0000242771218PW_BS00002465111PW_BS0000652905491PW_BS000024253541PW_BS0000243331212PW_BS0000283522512PW_BS00002835325127PW_BS00002835625121PW_BS0000283702601PW_BS000028228361PW_BS000024232403PW_BS000024412125PW_BS0001154192551PW_BS000115436255PW_BS0001154461217PW_BS00011545525171PW_BS0001154712517PW_BS00011547225177PW_BS00011548718101PW_BS00011549025101PW_BS0001155072561PW_BS0001155131761PW_BS000115111811PW_BS00001114117191PW_BS00014178811PW_BS000078229371PW_BS0000245311015PW_BS0000532374RosiglitazoneHMDB0005031Rosiglitazone is an anti-diabetic drug from the thiazolidinedione class. Like other thiazolidinediones, its mechanism of action is by activation of the intracellular receptor class of the peroxisome proliferator-activated receptors (PPARs), specifically PPAR-gamma. Rosiglitazone is a pure ligand of PPAR-gamma, and has no PPAR-alpha-binding action. Apart from its effect on insulin resistance, it appears to have an anti-inflammatory effect: nuclear factor kappa-B (NFκB) levels fall and inhibitor (IκB) levels increase in patients on rosiglitazone (Mohanty et al). It increases glyceroneogenesis and reduces the release of free fatty acids from adipocytes; Rosiglitazone is an anti-diabetic drug from the thiazolidinedione class. It is being marketed as Avandia by the pharmaceutical company GlaxoSmithKline, both as a standalone preparation and in combination with metformin (Avandamet). Another combination drug approved by the FDA is Avandaryl (with glimepiride); Like other thiazolidinediones, its mechanism of action is by activation of the intracellular receptor class of the peroxisome proliferator-activated receptors (PPARs), specifically PPAR-gamma. Rosiglitazone is a pure ligand of PPAR-gamma, and has no PPAR-alpha binding action. Apart from its effect on insulin resistance, it appears to have an anti-inflammatory effect: nuclear factor kappa-B (NFkB) levels fall and inhibitor (IkB) levels increase in patients on rosiglitazone (Mohanty et al). It increases glyceroneogenesis and reduces the release of free fatty acids from adipocytes.122320-73-4779995012270383DB00412CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=CC=CC=N1C18H19N3O3SInChI=1S/C18H19N3O3S/c1-21(16-4-2-3-9-19-16)10-11-24-14-7-5-13(6-8-14)12-15-17(22)20-18(23)25-15/h2-9,15H,10-12H2,1H3,(H,20,22,23)YASAKCUCGLMORW-UHFFFAOYSA-N5-[(4-{2-[methyl(pyridin-2-yl)amino]ethoxy}phenyl)methyl]-1,3-thiazolidine-2,4-dione357.427357.114712179-3.971rosiglitazone0-1FDB023598Avandia;Rosiglitazone maleate;Rosiglizole;5-((4-(2-(methyl-2-pyridinylamino)ethoxy)phenyl)methyl)-2,4-thiazolidinedione;Brl-49653;Rosiglitazona;RosiglitazonumPW_C002374Rosigl40212943241543253140633N-Despyridinyl rosiglitazoneHMDB0060842N-Despyridinyl rosiglitazone is a metabolite of rosiglitazone. Rosiglitazone is an antidiabetic drug in the thiazolidinedione class of drugs. It works as an insulin sensitizer, by binding to the PPAR receptors in fat cells and making the cells more responsive to insulin. It is marketed by the pharmaceutical company GlaxoSmithKline (GSK) as a stand-alone drug (Avandia) and in combination with metformin (Avandamet) or with glimepiride (Avandaryl). Annual sales peaked at approximately $2.5bn in 2006, but declined after reports of adverse effects. (Wikipedia)103563208531772CNCCOC1=CC=C(CC2SC(=O)NC2=O)C=C1C13H16N2O3SInChI=1S/C13H16N2O3S/c1-14-6-7-18-10-4-2-9(3-5-10)8-11-12(16)15-13(17)19-11/h2-5,11,14H,6-8H2,1H3,(H,15,16,17)BPSKNLFJDYBECE-UHFFFAOYSA-N5-({4-[2-(methylamino)ethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione280.343280.088163078-3.3625-({4-[2-(methylamino)ethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione00DBMET00942PW_C040633Ndespr40222940637N-desmethylrosiglitazoneHMDB0060980N-desmethylrosiglitazone is a metabolite of rosiglitazone. Rosiglitazone is an antidiabetic drug in the thiazolidinedione class of drugs. It works as an insulin sensitizer, by binding to the PPAR receptors in fat cells and making the cells more responsive to insulin. It is marketed by the pharmaceutical company GlaxoSmithKline (GSK) as a stand-alone drug (Avandia) and in combination with metformin (Avandamet) or with glimepiride (Avandaryl). Annual sales peaked at approximately $2.5bn in 2006, but declined after reports of adverse effects. (Wikipedia)1200032810172795OC1=NC(=O)SC1CC1=CC=C(OCCNC2=CC=CC=N2)C=C1C17H17N3O3SInChI=1S/C17H17N3O3S/c21-16-14(24-17(22)20-16)11-12-4-6-13(7-5-12)23-10-9-19-15-3-1-2-8-18-15/h1-8,14H,9-11H2,(H,18,19)(H,20,21,22)ZJQTVMXUIGXRMR-UHFFFAOYSA-N4-hydroxy-5-[(4-{2-[(pyridin-2-yl)amino]ethoxy}phenyl)methyl]-2,5-dihydro-1,3-thiazol-2-one343.4343.099062115-3.7324-hydroxy-5-({4-[2-(pyridin-2-ylamino)ethoxy]phenyl}methyl)-5H-1,3-thiazol-2-one0-1DBMET00295PW_C040637Ndes40232940631N-Desmethyl-p-hydroxyrosiglitazoneHMDB0060838N-Desmethyl-p-hydroxyrosiglitazone is a metabolite of rosiglitazone. Rosiglitazone is an antidiabetic drug in the thiazolidinedione class of drugs. It works as an insulin sensitizer, by binding to the PPAR receptors in fat cells and making the cells more responsive to insulin. It is marketed by the pharmaceutical company GlaxoSmithKline (GSK) as a stand-alone drug (Avandia) and in combination with metformin (Avandamet) or with glimepiride (Avandaryl). Annual sales peaked at approximately $2.5bn in 2006, but declined after reports of adverse effects. (Wikipedia)OC1=CC=C(NCCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)N=C1C17H17N3O4SInChI=1S/C17H17N3O4S/c21-12-3-6-15(19-10-12)18-7-8-24-13-4-1-11(2-5-13)9-14-16(22)20-17(23)25-14/h1-6,10,14,21H,7-9H2,(H,18,19)(H,20,22,23)SVUUNTJZVPNZSL-UHFFFAOYSA-N5-[(4-{2-[(5-hydroxypyridin-2-yl)amino]ethoxy}phenyl)methyl]-1,3-thiazolidine-2,4-dione359.4359.093976737-3.7735-[(4-{2-[(5-hydroxypyridin-2-yl)amino]ethoxy}phenyl)methyl]-1,3-thiazolidine-2,4-dione0-1DBMET00938PW_C040631Ndesph40242940629N-Desmethyl-O-hydroxy rosiglitazoneHMDB0060836N-Desmethyl-O-hydroxy rosiglitazone is a metabolite of rosiglitazone. Rosiglitazone is an antidiabetic drug in the thiazolidinedione class of drugs. It works as an insulin sensitizer, by binding to the PPAR receptors in fat cells and making the cells more responsive to insulin. It is marketed by the pharmaceutical company GlaxoSmithKline (GSK) as a stand-alone drug (Avandia) and in combination with metformin (Avandamet) or with glimepiride (Avandaryl). Annual sales peaked at approximately $2.5bn in 2006, but declined after reports of adverse effects. (Wikipedia)8627829832702400OC1=C(NCCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)N=CC=C1C17H17N3O4SInChI=1S/C17H17N3O4S/c21-13-2-1-7-18-15(13)19-8-9-24-12-5-3-11(4-6-12)10-14-16(22)20-17(23)25-14/h1-7,14,21H,8-10H2,(H,18,19)(H,20,22,23)GWVBGLUFILBNNY-UHFFFAOYSA-N5-[(4-{2-[(3-hydroxypyridin-2-yl)amino]ethoxy}phenyl)methyl]-1,3-thiazolidine-2,4-dione359.4359.093976737-3.7335-[(4-{2-[(3-hydroxypyridin-2-yl)amino]ethoxy}phenyl)methyl]-1,3-thiazolidine-2,4-dione00DBMET00936PW_C040629Ndesohr40272940639ortho-hydroxyrosiglitazoneHMDB0061105ortho-hydroxyrosiglitazone is a metabolite of rosiglitazone. Rosiglitazone is an antidiabetic drug in the thiazolidinedione class of drugs. It works as an insulin sensitizer, by binding to the PPAR receptors in fat cells and making the cells more responsive to insulin. It is marketed by the pharmaceutical company GlaxoSmithKline (GSK) as a stand-alone drug (Avandia) and in combination with metformin (Avandamet) or with glimepiride (Avandaryl). Annual sales peaked at approximately $2.5bn in 2006, but declined after reports of adverse effects. (Wikipedia)CN(CCOC1=CC=C(CC2SC(=O)N=C2O)C=C1)C1=C(O)C=CC=N1C18H19N3O4SInChI=1S/C18H19N3O4S/c1-21(16-14(22)3-2-8-19-16)9-10-25-13-6-4-12(5-7-13)11-15-17(23)20-18(24)26-15/h2-8,15,22H,9-11H2,1H3,(H,20,23,24)KQXWMUFVDAFGPU-UHFFFAOYSA-N4-hydroxy-5-[(4-{2-[(3-hydroxypyridin-2-yl)(methyl)amino]ethoxy}phenyl)methyl]-2,5-dihydro-1,3-thiazol-2-one373.426373.109626801-3.4524-hydroxy-5-[(4-{2-[(3-hydroxypyridin-2-yl)(methyl)amino]ethoxy}phenyl)methyl]-5H-1,3-thiazol-2-one00DBMET00470PW_C040639OrthoHl40282940638para-hydroxyrosiglitazoneHMDB0060981para-hydroxyrosiglitazone is a metabolite of rosiglitazone. Rosiglitazone is an antidiabetic drug in the thiazolidinedione class of drugs. It works as an insulin sensitizer, by binding to the PPAR receptors in fat cells and making the cells more responsive to insulin. It is marketed by the pharmaceutical company GlaxoSmithKline (GSK) as a stand-alone drug (Avandia) and in combination with metformin (Avandamet) or with glimepiride (Avandaryl). Annual sales peaked at approximately $2.5bn in 2006, but declined after reports of adverse effects. (Wikipedia)98643168040009CN(CCOC1=CC=C(CC2SC(=O)N=C2O)C=C1)C1=NC=C(O)C=C1C18H19N3O4SInChI=1S/C18H19N3O4S/c1-21(16-7-4-13(22)11-19-16)8-9-25-14-5-2-12(3-6-14)10-15-17(23)20-18(24)26-15/h2-7,11,15,22H,8-10H2,1H3,(H,20,23,24)AGQGGZNSVNKGDU-UHFFFAOYSA-N4-hydroxy-5-[(4-{2-[(5-hydroxypyridin-2-yl)(methyl)amino]ethoxy}phenyl)methyl]-2,5-dihydro-1,3-thiazol-2-one373.426373.109626801-3.4624-hydroxy-5-[(4-{2-[(5-hydroxypyridin-2-yl)(methyl)amino]ethoxy}phenyl)methyl]-5H-1,3-thiazol-2-one0-1DBMET00296PW_C040638PHRZone40292940641p-O-sulfate rosiglitazoneHMDB00612415-Hydroxyrosiglitazone sulfate belongs to the class of organic compounds known as arylsulfates. These are organic compounds containing a sulfate group that carries an aryl group through an ether group. 5-Hydroxyrosiglitazone sulfate is considered to be a practically insoluble (in water) and relatively neutral molecule.98467238022437CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=CC=C(OS(O)(=O)=O)C=N1C18H19N3O7S2InChI=1S/C18H19N3O7S2/c1-21(16-7-6-14(11-19-16)28-30(24,25)26)8-9-27-13-4-2-12(3-5-13)10-15-17(22)20-18(23)29-15/h2-7,11,15H,8-10H2,1H3,(H,20,22,23)(H,24,25,26)WAGUBJKZLRLKGR-UHFFFAOYSA-N{6-[(2-{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy}ethyl)(methyl)amino]pyridin-3-yl}oxidanesulfonic acid453.489453.066441357-4.292{6-[(2-{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy}ethyl)(methyl)amino]pyridin-3-yl}oxidanesulfonic acid0-2DBMET01112PW_C040641POSR40342940632N-Desmethyl-p-O-sulfate rosiglitazoneHMDB0060839N-Desmethyl-p-O-sulfate rosiglitazone is a metabolite of rosiglitazone. Rosiglitazone is an antidiabetic drug in the thiazolidinedione class of drugs. It works as an insulin sensitizer, by binding to the PPAR receptors in fat cells and making the cells more responsive to insulin. It is marketed by the pharmaceutical company GlaxoSmithKline (GSK) as a stand-alone drug (Avandia) and in combination with metformin (Avandamet) or with glimepiride (Avandaryl). Annual sales peaked at approximately $2.5bn in 2006, but declined after reports of adverse effects. (Wikipedia)OS(=O)(=O)OC1=CC=C(NCCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)N=C1C17H17N3O7S2InChI=1S/C17H17N3O7S2/c21-16-14(28-17(22)20-16)9-11-1-3-12(4-2-11)26-8-7-18-15-6-5-13(10-19-15)27-29(23,24)25/h1-6,10,14H,7-9H2,(H,18,19)(H,20,21,22)(H,23,24,25)ULPCBLHRDLQTTD-UHFFFAOYSA-N{6-[(2-{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy}ethyl)amino]pyridin-3-yl}oxidanesulfonic acid439.463439.050791293-4.323{6-[(2-{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy}ethyl)amino]pyridin-3-yl}oxidanesulfonic acid0-2DBMET00939PW_C040632NdesOsr40352940640N-desmethyl glucuronide rosiglitazoneHMDB00612403,4,5-Trihydroxy-6-({2-[(2-{4-[(4-hydroxy-2-oxo-2,5-dihydro-1,3-thiazol-5-yl)methyl]phenoxy}ethyl)amino]pyridin-3-yl}oxy)oxane-2-carboxylic acid belongs to the class of organic compounds known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond. 3,4,5-Trihydroxy-6-({2-[(2-{4-[(4-hydroxy-2-oxo-2,5-dihydro-1,3-thiazol-5-yl)methyl]phenoxy}ethyl)amino]pyridin-3-yl}oxy)oxane-2-carboxylic acid is considered to be a practically insoluble (in water) and relatively neutral molecule.OC1C(OC2=C(NCCOC3=CC=C(CC4SC(=O)N=C4O)C=C3)N=CC=C2)OC(C(O)C1O)C(O)=OC23H25N3O10SInChI=1S/C23H25N3O10S/c27-15-16(28)18(21(31)32)36-22(17(15)29)35-13-2-1-7-24-19(13)25-8-9-34-12-5-3-11(4-6-12)10-14-20(30)26-23(33)37-14/h1-7,14-18,22,27-29H,8-10H2,(H,24,25)(H,31,32)(H,26,30,33)NLGMKXBTZZJJFK-UHFFFAOYSA-N3,4,5-trihydroxy-6-({2-[(2-{4-[(4-hydroxy-2-oxo-2,5-dihydro-1,3-thiazol-5-yl)methyl]phenoxy}ethyl)amino]pyridin-3-yl}oxy)oxane-2-carboxylic acid535.524535.126064725-3.2763,4,5-trihydroxy-6-({2-[(2-{4-[(4-hydroxy-2-oxo-5H-1,3-thiazol-5-yl)methyl]phenoxy}ethyl)amino]pyridin-3-yl}oxy)oxane-2-carboxylic acid0-2DBMET01111PW_C040640Ndesgr40362940630N-Desmethyl-o-O-sulfate rosiglitazoneHMDB0060837N-Desmethyl-o-O-sulfate rosiglitazone is a metabolite of rosiglitazone. Rosiglitazone is an antidiabetic drug in the thiazolidinedione class of drugs. It works as an insulin sensitizer, by binding to the PPAR receptors in fat cells and making the cells more responsive to insulin. It is marketed by the pharmaceutical company GlaxoSmithKline (GSK) as a stand-alone drug (Avandia) and in combination with metformin (Avandamet) or with glimepiride (Avandaryl). Annual sales peaked at approximately $2.5bn in 2006, but declined after reports of adverse effects. (Wikipedia)OS(=O)(=O)OC1=C(NCCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)N=CC=C1C17H17N3O7S2InChI=1S/C17H17N3O7S2/c21-16-14(28-17(22)20-16)10-11-3-5-12(6-4-11)26-9-8-19-15-13(2-1-7-18-15)27-29(23,24)25/h1-7,14H,8-10H2,(H,18,19)(H,20,21,22)(H,23,24,25)HOMPAUSQZJYDFA-UHFFFAOYSA-N{2-[(2-{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy}ethyl)amino]pyridin-3-yl}oxidanesulfonic acid439.463439.050791293-4.253{2-[(2-{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy}ethyl)amino]pyridin-3-yl}oxidanesulfonic acid0-2DBMET00937PW_C040630Ndesoos40372940634o-O-glucuronide rosiglitazoneHMDB0060857o-O-glucuronide rosiglitazone is a metabolite of rosiglitazone. Rosiglitazone is an antidiabetic drug in the thiazolidinedione class of drugs. It works as an insulin sensitizer, by binding to the PPAR receptors in fat cells and making the cells more responsive to insulin. It is marketed by the pharmaceutical company GlaxoSmithKline (GSK) as a stand-alone drug (Avandia) and in combination with metformin (Avandamet) or with glimepiride (Avandaryl). Annual sales peaked at approximately $2.5bn in 2006, but declined after reports of adverse effects. (Wikipedia)CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=C(OC2OC(C(O)C(O)C2O)C(O)=O)C=CC=N1C24H27N3O10SInChI=1S/C24H27N3O10S/c1-27(9-10-35-13-6-4-12(5-7-13)11-15-21(31)26-24(34)38-15)20-14(3-2-8-25-20)36-23-18(30)16(28)17(29)19(37-23)22(32)33/h2-8,15-19,23,28-30H,9-11H2,1H3,(H,32,33)(H,26,31,34)YDRMOALONMVDNG-UHFFFAOYSA-N6-({2-[(2-{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy}ethyl)(methyl)amino]pyridin-3-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid549.55549.141714789-2.7456-({2-[(2-{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy}ethyl)(methyl)amino]pyridin-3-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid0-2DBMET00968PW_C040634oogr40635o-O-sulfate rosiglitazoneHMDB0060858o-O-sulfate rosiglitazone is a metabolite of rosiglitazone. Rosiglitazone is an antidiabetic drug in the thiazolidinedione class of drugs. It works as an insulin sensitizer, by binding to the PPAR receptors in fat cells and making the cells more responsive to insulin. It is marketed by the pharmaceutical company GlaxoSmithKline (GSK) as a stand-alone drug (Avandia) and in combination with metformin (Avandamet) or with glimepiride (Avandaryl). Annual sales peaked at approximately $2.5bn in 2006, but declined after reports of adverse effects. (Wikipedia)CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=C(OS(O)(=O)=O)C=CC=N1C18H19N3O7S2InChI=1S/C18H19N3O7S2/c1-21(16-14(3-2-8-19-16)28-30(24,25)26)9-10-27-13-6-4-12(5-7-13)11-15-17(22)20-18(23)29-15/h2-8,15H,9-11H2,1H3,(H,20,22,23)(H,24,25,26)ZVSPRKOUHTZIGH-UHFFFAOYSA-N{2-[(2-{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy}ethyl)(methyl)amino]pyridin-3-yl}oxidanesulfonic acid453.489453.066441357-4.232{2-[(2-{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy}ethyl)(methyl)amino]pyridin-3-yl}oxidanesulfonic acid0-2DBMET00969PW_C040635oosr40636p-O-glucuronide rosiglitazoneHMDB0060862p-O-glucuronide rosiglitazone is a metabolite of rosiglitazone. Rosiglitazone is an antidiabetic drug in the thiazolidinedione class of drugs. It works as an insulin sensitizer, by binding to the PPAR receptors in fat cells and making the cells more responsive to insulin. It is marketed by the pharmaceutical company GlaxoSmithKline (GSK) as a stand-alone drug (Avandia) and in combination with metformin (Avandamet) or with glimepiride (Avandaryl). Annual sales peaked at approximately $2.5bn in 2006, but declined after reports of adverse effects. (Wikipedia)7806986122547081CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=CC=C(OC2OC(C(O)C(O)C2O)C(O)=O)C=N1C24H27N3O10SInChI=1S/C24H27N3O10S/c1-27(8-9-35-13-4-2-12(3-5-13)10-15-21(31)26-24(34)38-15)16-7-6-14(11-25-16)36-23-19(30)17(28)18(29)20(37-23)22(32)33/h2-7,11,15,17-20,23,28-30H,8-10H2,1H3,(H,32,33)(H,26,31,34)QGESYIGEZXWVIN-UHFFFAOYSA-N6-({6-[(2-{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy}ethyl)(methyl)amino]pyridin-3-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid549.55549.141714789-2.7556-({6-[(2-{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy}ethyl)(methyl)amino]pyridin-3-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid0-2DBMET00981PW_C040636POGR40658Phenoxyacetic acid derivativeHMDB0061357Phenoxyacetic acid is found in cocoa and cocoa products. Phenoxyacetic acid is a flavouring ingredient. Phenoxyacetic acid is present in cocoa beans Phenoxyacetic acid has been shown to exhibit neurotransmitter function. Phenoxyacetic acid belongs to the family of Phenoxyacetic Acid Derivatives. These are compounds containing an anisole where the methane group is linked to an acetic acid or a derivative.OC(=O)COC1=CC=CC=C1C8H8O3InChI=1S/C8H8O3/c9-8(10)6-11-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10)LCPDWSOZIOUXRV-UHFFFAOYSA-N2-phenoxyacetic acid152.1473152.047344122-1.461phenoxyacetic acid0-12-phenoxy-acetic acid;Fema 2872;Glycol acid phenyl ether;Glycolic acid phenyl ether;Glycolic acid, phenyl ether;Glycollic acid phenyl ether;O-phenylglycolic acid;Phenoxy acetic acid;Phenoxy-acetic acid;Phenoxyacetate;Phenoxyethanoic acid;Phenxoyacetic acid;Phenyl ether glycolic acid;PoaPW_C040658Paderiv1065OxygenHMDB0001377Oxygen 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-Noxidanone31.998831.9898292440singlet oxygen00FDB022589Dioxygen;Molecular oxygen;O2;Oxygen;Oxygen molecule;[oo];Dioxygene;Disauerstoff;E 948;E-948;E948PW_C001065O295911052451650018505854914625286383649106743168820754157634769338362137549201624253122280329426042474713546712354801255493126550812758091085973147612915970061887032163705016073192137533210756021283951511181621611864198118832151189421112057225120631641224728612279226123252491270629112716292130042981301630013026301130383021326022342276174265731576910293770442947721413477350111773631307737733177395332774971137751211577537334776263367772333777736112777471297775634177805114778121337807032978151132783813457880534379111360120047408120383122120426405120542407120553414120594409120601406120883415121045124121104383121605434121656429122117382122573418122689384122798374122822443123027135123060376123128447123139136123163448123176119123187450123219137123226120123459451123609118123669398124163469124214464124669399125145454125275121125425482125706478125731483125737297125740479125884481126100299126272484126522495126721489126825480126964502126986207127198209127214208127219205127222501127305504127345206127557388127574515127835389128081395128095390128312506128432391146NADPHHMDB0000221Nicotinamide 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=C(N)N=CN=C23)[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-/m0/s1ACFIXJIJDZMPPO-NCHANQSKSA-N{[(2S,3S,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-[({[({[(2S,3R,4S,5S)-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 acid745.4209745.091102105-2.149[(2S,3S,4S,5S)-2-(6-aminopurin-9-yl)-5-{[({[(2S,3R,4S,5S)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxyphosphonic acid0-4FDB0219092'-(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_C000146NADPH1858190377810796582118837216092916154946873147931447971453101115789108597214761281596271356779117706818871031637154205720516073152137345210755921275911708194225821915184212241181219811893211120062221215016412245286125962261264824942343315437463227691129377166132773853317739433277460130775041127751111577623336807121191131649412010540712042540512045212212061612312114112512127542912140212412148338312305937612308613512324144712371213612384646412396111812404139812547248112569629712621429912652949512700920612757238812810139040034Hydrogen IonHMDB0059597Hydrogen ion is recommended by IUPAC as a general term for all ions of hydrogen and its isotopes. Depending on the charge of the ion, two different classes can be distinguished: positively charged ions and negatively charged ions. Under aqueous conditions found in biochemistry, hydrogen ions exist as the hydrated form hydronium, H3O+, but these are often still referred to as hydrogen ions or even protons by biochemists. [WikiPedia])C000801038153781010[H+]HInChI=1S/p+1GPRLSGONYQIRFK-UHFFFAOYSA-Nhydron1.00791.0078250320hydron10H+;H(+);Hydrogen cation;Hydron;ProtonPW_C040034H+2154670875315788318483111621463261464542231492780174250224254424547104576184694705241103532711153531125626108563910756991005720105574211759631476037155607015760931616130159623216664831786601152669210168431886910187710016371682057191206745321974542207472222752521375322107558212757216075901708195225821815182432268413162842022491391959155249119151641201528112181285122462861226628712521227132572231332529415330308423293154235431842401322424053124245432076912293771361337721013477372331778041147795513277990327779913477837934579929130800193688038731080388304807221199382312494823383110550388112855941132803901155373981155391181158563361162051091199734061201934071205491221205934091211704241211714251225694181226153841226871251227581201231831351232181371237424591237434601251414541251881211252731361253594791255504811257304831257362971258092991265174951267174891267664801268233001269025011272132081283085061283613911284303951420WaterHMDB0002111Water 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_C001420H2O5589491095139415131621448113526156242865210691207703382318838210943113774914655415904320182425322226786027274627781728052931437031647236346145983647273749419350302751567519597521410052279452361035297105531911153431135355112540211054701235483125549212655071275534130553711455411295591135560811856221085691657591405778101584114358531465877107589095591014759401516032155605915760871616123163613315962151621816664771786507180660015267131176840188688816071622057181207719320672112117228213723821472432157295198735021673882107401212746722274922247500190758817082012258237226841416292652611850277119221641201128112213285122502861226428712327249125202271263265126932901270529112715292130072981301930013025301130373021326122313327294153403084232731542695318436913227691429377019253771021327713113377215134773783317739733277471333775161157753633477628336777223377775934177816343779823477807132978235352782423537827035679113360800143688003937080591228806561199383038394794384110557390110639391115844398119879232119915122119963406120008407120046408120113124120365412120430405120438409120606415120794414121158425121240429121351121121381419121607434122118382122384436122753120122797374122804443123012446123064376123072137123131447123142136123162448123231451123384450123730460123810464123940455124165469124670399124938471124945472125305297125353479125386481125424482125480299125682483125707478125745487126054490126238495126273484126764480126896501126963502127017388127177208127199209127227504127506507127576515127836389128082395128176513143NADPHMDB0000217Nicotinamide 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](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1OC21H29N7O17P3InChI=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)/p+1/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1XJLXINKUBYWONI-NNYOXOHSSA-O1-[(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)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium744.4129744.083277073-2.2791-[(2R,3R,4S,5R)-5-{[({[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium1-3FDB021908Adenine-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_C000143NADP18381913768578010824188392161129161749468531479614480114530811157901086017147613215962733567781177069188710516371522057206160731721373462107562212758917081972258220151841922411811198118972111200822212152164122492861259722612650249423443154374532276913293771641327738433177396332774611307751511577624336778143347787011280713119113165941201064071204294051204501221206044081206181231211421251212774291214011241214853831230633761230841351232293741232434471237131361238484641239601181240433981254734811256942971257434821262152991265284951270102061272255021275703881281003901799HemeHMDB0003178Heme 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_C001799Heme2471630810324860827665124431354491413361963182806292938932381133672634211437344404331482328517095547212354851255517129583014162467862831659715170441607060161732621311835198118982111206516413009298130213004227817769152937693124977351111773641307736733177398332775171157762933677813334783801337860213278963112799321341204314051206034081209554071210853831216584291217461241219101221225704061226913841230653761231334471231441361232283741235211191236503981242164641242971181244631351251421201252771211257424821258964811261962991264992971265124951267184791268274801272245021273572061276323881280702051280833951280863901283095011284343911144NADHHMDB0001487NADH is the reduced form of NAD+, and NAD+ is the oxidized form of NADH, A coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). It forms NADP with the addition of a phosphate group to the 2' position of the adenosyl nucleotide through an ester linkage.(Dorland, 27th ed).58-68-4C0000443915316908NADH388299DB00157NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1OC21H29N7O14P2InChI=1S/C21H29N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1,3-4,7-8,10-11,13-16,20-21,29-32H,2,5-6H2,(H2,23,33)(H,34,35)(H,36,37)(H2,22,24,25)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1BOPGDPNILDQYTO-NNYOXOHSSA-N[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4R,5R)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy})phosphinic acid665.441665.124771695-2.358NADH0-2FDB0226491,4-dihydronicotinamide adenine dinucleotide;Dpnh;Dihydrocodehydrogenase i;Dihydrocozymase;Dihydronicotinamide adenine dinucleotide;Dihydronicotinamide mononucleotide;Enada;Nadh;Nadh2;Reduced codehydrogenase i;Reduced diphosphopyridine nucleotide;Reduced nicotinamide adenine diphosphate;Reduced nicotinamide-adenine dinucleotide;B-dpnh;B-nadh;Beta-dpnh;Beta-nadh;Nicotinamide adenine dinucleotide (reduced);Reduced nicotinamide adenine dinucleotidePW_C001144NADH143415334908648101115212755146954223049278117283629310994806184812184821284904649593151699552401035332111535811254661235479125559313556981005737108582914159151475945151602715560791616387164721786771117689316070111887099163717220571952067462222824422683602259086224118091981182121612320249130032981301530013255223424033224261831577107132771231337720813477371331776513367766833477700332777071307791711377986347800093688069111993822124110549388112854941158381181199554061201724071203781221209864081211624251212441261216934291218183831226163841227451201231274471231381361235513741237344601238144431242424641243713981251891211253454791255314811257622971258082991259264821265164951267674801268885011273855021280903901283623911284293951102FormaldehydeHMDB0001426Formaldehyde is a highly reactive aldehyde gas formed by oxidation or incomplete combustion of hydrocarbons. In solution, it has a wide range of uses: in the manufacture of resins and textiles, as a disinfectant, and as a laboratory fixative or preservative. Formaldehyde solution (formalin) is considered a hazardous compound, and its vapor toxic. (From Reynolds, Martindale The Extra Pharmacopoeia, 30th ed, p717) -- Pubchem; The chemical compound formaldehyde (also known as methanal), is a gas with a pungent smell. It is the simplest aldehyde. Its chemical formula is H2CO. Formaldehyde was first synthesized by the Russian chemist Aleksandr Butlerov in 1859 but was conclusively identified by August Wilhelm van Hofmann in 1867. Although formaldehyde is a gas at room temperature, it is readily soluble in water, and it is most commonly sold as a 37% solution in water called by trade names such as formalin or formol. In water, formaldehyde polymerizes, and formalin actually contains very little formaldehyde in the form of H2CO monomer. Usually, these solutions contain a few percent methanol to limit the extent of polymerization. Formaldehyde exhibits most of the general chemical properties of the aldehydes, except that is generally more reactive than other aldehydes. Formaldehyde is a potent electrophile. It can participate in electrophilic aromatic substitution reactions with aromatic compounds and can undergo electrophilic addition reactions with alkenes. In the presence of basic catalysts, formaldehyde undergoes a Cannizaro reaction to produce formic acid and methanol. Because formaldehyde resins are used in many construction materials, including plywood, carpet, and spray-on insulating foams, and because these resins slowly give off formaldehyde over time, formaldehyde is one of the more common indoor air pollutants. At concentrations above 0.1 mg/kg in air, inhaled formaldehyde can irritate the eyes and mucous membranes, resulting in watery eyes, headache, a burning sensation in the throat, and difficulty breathing. -- Wikipedia.50-00-0C0006771216842FORMALDEHYDE692DB03843C=OCH2OInChI=1S/CH2O/c1-2/h1H2WSFSSNUMVMOOMR-UHFFFAOYSA-Nformaldehyde30.02630.0105646860.820formaldehyde00DBMET00531FDB009445Methaldehyde;Methylene glycol;Aldeide formica;Chlodithan;Chlodithane;Fannoform;Formaldehyde;Formalina;Formaline;Formalith;Formic aldehyde;Formol;Methanal;Methylene oxide;Oxomethylene;Paraform;Formaldehyd;Formalin;OxomethanePW_C001102Formol65310255532562445891854711235484125130082981302030077703332777101307808011278083133122126407122129406123132447123143136124678119124681120126283481126286479127846206127849501721NADHMDB0000902NAD (or Nicotinamide adenine dinucleotide) is used extensively in glycolysis and the citric acid cycle of cellular respiration. The reducing potential stored in NADH can be converted to ATP through the electron transport chain or used for anabolic metabolism. ATP "energy" is necessary for an organism to live. Green plants obtain ATP through photosynthesis, while other organisms obtain it by cellular respiration. (wikipedia). Nicotinamide adenine dinucleotide is a A coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). (Dorland, 27th ed).53-84-9C00003589315846NAD5682NC(=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](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1OC21H28N7O14P2InChI=1S/C21H27N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1-4,7-8,10-11,13-16,20-21,29-32H,5-6H2,(H5-,22,23,24,25,33,34,35,36,37)/p+1/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1BAWFJGJZGIEFAR-NNYOXOHSSA-O1-[(2R,3R,4S,5R)-5-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium664.433664.116946663-2.5981-[(2R,3R,4S,5R)-5-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium1-1FDB0223093-carbamoyl-1-d-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate;3-carbamoyl-1-beta-d-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt;3-carbamoyl-1-beta-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt;3-carbamoyl-1-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate;Adenine-nicotinamide dinucleotide;Co-i;Codehydrase i;Codehydrogenase i;Coenzyme i;Cozymase;Cozymase i;Diphosphopyridine nucleotide;Diphosphopyridine nucleotide oxidized;Endopride;Nad trihydrate;Nad-oxidized;Nicotinamide adenine dinucleotide;Nicotinamide adenine dinucleotide oxidized;Nicotinamide dinucleotide;Nicotineamide adenine dinucleotide;Oxidized diphosphopyridine nucleotide;Pyridine nucleotide diphosphate;[(3s,2r,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[(3s,2r,4r,5r)-5-(3-carbamoylpyridyl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxyphosphoryl) hydrogen phosphate;[adenylate-32-p]-nad;Beta-diphosphopyridine nucleotide;Beta-nad;Beta-nicotinamide adenine dinucleotide;Beta-nicotinamide adenine dinucleotide trihydrate;Dpn;Nad;Nad+;Nadide;B-nad;β-nadPW_C000721NAD14041503353865110111421134431273514665422294927791728352931079480718481318481928490264960315167955238103533411153601125469123548212555901355610118569610057381085827141591214759421516024155607215760761616385164691786772117689016070121887097163717420571972067405198745922282412268359225908522411819216123222491300629813018300132562234240432242619315771041327712013377209134773703317765033677667334777023327770913077915113779833477840635680006368806901199382512411055238811275016611285394119929122119952406120171407120834419120984408121159425121242126121259429121817383122614384122742120123130447123141136123419455123549374123731460123812443123829464124370398125187121125319297125342479125530481125806299125825490125924482126515495126765480126885501127278507127383502128089390128360391128428395440Solute carrier organic anion transporter family member 1B1Q9Y6L6Mediates the Na(+)-independent transport of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. May play an important role in the clearance of bile acids and organic anions from the liverHMDBP00454SLCO1B112pAK312970184812291450Cytochrome 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).
HMDBP01562CYP2C810q23.33AK29332811.14.14.1137849335929380510400926480918481518973Cytochrome P450 2C9P11712Cytochromes 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. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
HMDBP01036CYP2C910q24AY34124811.14.13.-; 1.14.13.80; 1.14.13.48; 1.14.13.4933562934351038462404631481018481618930Solute carrier organic anion transporter family member 1B11PW_P00093010554401383Cytochrome P450 2C81PW_P0003834051450117917991820Cytochrome P450 2C91PW_P0008209449731351179912047falsePW_R002047Right732323741Compoundfalse7324406331Compoundfalse2048falsePW_R002048Right7325406371Compoundfalse7326406311Compoundfalse2051falsePW_R002051Right7335406371Compoundfalse7336406291Compoundfalse2052falsePW_R002052Right7337406391Compoundfalse7338406291Compoundfalse2055falsePW_R002055Right7344406381Compoundfalse7345406411Compoundfalse2057falsePW_R002057Right7348406381Compoundfalse7349406311Compoundfalse2058falsePW_R002058Right7350406311Compoundfalse7351406321Compoundfalse2059falsePW_R002059Right7352406371Compoundfalse7353406401Compoundfalse2061falsePW_R002061Right7357406291Compoundfalse7358406301Compoundfalse2063falsePW_R002063Right7362406391Compoundfalse7363406341Compoundfalse19323831.14.14.119338202086falsePW_R002086Right7421406381Compoundfalse7422406361Compoundfalse2088falsePW_R002088Right742523741Compoundfalse7426406581Compoundfalse2065falsePW_R002065Right736923741Compoundfalse892110651Compoundtrue89221461Compoundtrue8923400341Compoundtrue7370406391Compoundfalse892414201Compoundtrue89251431Compoundtrue19343831.14.14.119358202049falsePW_R002049Right732723741Compoundfalse892610651Compoundtrue892711441Compoundtrue7328406371Compoundfalse892811021Compoundtrue89297211Compoundtrue893014201Compoundtrue19213831.14.14.119228202053falsePW_R002053Right733923741Compoundfalse893110651Compoundtrue89321461Compoundtrue8933400341Compoundtrue7340406381Compoundfalse893414201Compoundtrue89351431Compoundtrue19243831.14.14.11925820224PW_T00022426123741Compound1531Right1849302013-09-20T13:57:52-06:002013-09-20T13:57:52-06:00538087237429157false54039510regular20019080884063329157false18558010regular20019080934063729157false1065117010regular20019080944063129157false700116510regular20020081034062929157false1510116510regular20020081044063929157false150071010regular200190810540629293true0010regular10012081064063829157false300117010regular20019081134064129157false530163510regular200190811740631293true0010regular10012081194063229157false825162510regular20020081204064029157false1165162510regular20020081224063029157false1510162510regular200200812440634157false179571010regular200190812540635157false1795107510regular200190824140636157false190163510regular200190824440658157false142039510regular2001908856237415157true0010regular2001908857237431157false8353010regular2001901130910651065false108651510regular7878113101461062false102570710regular503011311400341055false93161810regular78781131214201049false137061510regular7878113131431061false132081010regular5030113141799109false121060410regular10025113151799109false113574910regular100251131610651065false94174810regular78781131711441060false75584010regular5030113181102103false113096510regular100100113197211059false880103010regular50301132014201049false970108010regular7878113211799109false98287210regular10025113221799109false81095510regular100251132310651065false46070610regular7878113241461062false39282510regular503011325400341055false60378610regular78781132614201049false540103510regular7878113271431061false340102010regular5030113281799109false35988710regular10025113291799109false52995210regular10025483144022976false5652708subunitregular1507059441450102false11856148subunitregular150705945973102false11106948subunitregular1507059461450102false7879028subunitregular150705947973102false9608808subunitregular1507059481450102false3348978subunitregular150705949973102false5048978subunitregular150704004930376480448314895383376105915594423261131417684Cofactor4896820376105916594523271131517685Cofactor4897383376105917594623281132117693Cofactor4898820376105918594723291132217694Cofactor4899383376105919594823301132817702Cofactor4900820376105920594923311132917703Cofactor12142M540 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13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false12184M500 1265 C530 1265 211 623 235 640 5true1812185M630 1635 C630 1598 400 1396 400 1360 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false12190M500 1265 C538 1266 669 1263 700 1265 5false18trueM 353.06440098298674 615.6115180941069 L 368 617 L 361.73466109469183 603.3711508775821false12191M11 12 C34 28 74 55 98 72 5true18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false12196M900 1265 C930 1265 496 683 520 700 5true1812197M925 1625 C922 1585 804 1395 800 1365 5false18trueM 480.0096189432334 923.5 L 493 916 L 480.0096189432334 908.5false12198M1165 1360 C1165 1390 1266 1601 1265 1625 5false18trueM 646.0644009829867 922.6115180941069 L 661 924 L 654.7346610946918 910.3711508775821falsefalsefalse12199M1165 1725 C1135 1725 681 383 705 400 5true18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false12204M1710 1265 C1740 1265 941 713 965 730 5true1812205M1610 1625 C1610 1602 1611 1384 1610 1365 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false12209M1700 805 C1730 805 1076 388 1100 405 5true1812210M1795 805 C1765 805 1720 805 1700 805 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false12211M1795 1170 C1765 1170 1603 974 1600 900 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false12408M400 1360 C401 1381 289 1591 290 1635 5false18trueM 155.06440098298674 923.6115180941069 L 170 925 L 163.73466109469183 911.3711508775821falsefalsefalse12409M190 1730 C160 1730 451 868 475 885 5true18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false12416M740 490 C767 489 1392 490 1420 490 5false18trueM 631.0096189432334 311.5 L 644 304 L 631.0096189432334 296.5false12417M1420 490 C1390 490 446 298 470 315 5true18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false13782M640 395 C639 375 640 359 640 340 83false18trueM 386.86064878524815 262.40035866371915 L 395 275 L 401.8419338684158 261.65129440956076false13783M835 125 C782 126 639 219 640 270 83false1817677M740 490 C770 490 961 212 985 229 5true1817678M1125 593 C1126 613 1161 662 1213 686 5false1817679M1050 707 C1049 684 1196 672 1220 689 5false1817680M1009 657 C1039 657 1178 664 1202 681 5false1817681M1500 805 C1470 805 784 489 740 490 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false17682M1409 693 C1411 720 1277 715 1227 692 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false17683M1345 810 C1343 782 1287 718 1236 695 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false17684M150 150 L150 200 L200 150 z10true1817685M150 150 L150 200 L200 150 z10true1817686M740 490 C770 490 823.5 300 847.5 317 5true1817687M941 787 C922 786 913.5 892 945.5 926 5false1817688M805 855 C835 855 886.5 861 945.5 925 5false1817689M1165 1170 C1163 1127 640 632 640 585 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false17690M1130 1015 C1100 1015 998.5 977 951.5 931 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false17691M930 1045 C950 1046 967.5 947 940.5 919 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false17692M1009 1080 C1008 1057 973.5 952 949.5 928 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false17693M150 150 L150 200 L200 150 z10true1817694M150 150 L150 200 L200 150 z10true1817695M640 585 C640 615 330 800.5 354 817.5 5true1817696M499 784 C499 814 512 892.5 495 934.5 5false1817697M442 840 C462 838 509 905.5 491 943.5 5false1817698M603 825 C581 827 511 896.5 494 936.5 5false1817699M400 1170 C400 1140 640 606 640 585 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false17700M540 1074 C519 1075 475 981.5 493 938.5 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false17701M390 1035 C411 1035 478 972 494 935 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false17702M150 150 L150 200 L200 150 z10true1817703M150 150 L150 200 L200 150 z10true1823783762047297877808712142Left7878808812143Right23813762048297882809312158Left7883809412159Right23843762051297889809312170Left7890810312171Right23853762052297891810412172Left7892810512173Right23883762055297896810612184Left7897811312185Right23903762057297898810612190Left7899811712191Right23923762058297900809412196Left7901811912197Right23933762059297902809312198Left7903812012199Right23953762061297905810312204Left7906812212205Right239737620637908810412209Left7909812412210Right7910812512211Right243437620867967810612408Left7968824112409Right243637620887969808712416Left7970824412417Right325537620651010713808717677Left107141130917678Left107151131017679Left107161131117680Left10717810417681Right107181131217682Right107191131317683Right342519344895342619354896325637620491010720808717686Left107211131617687Left107221131717688Left10723809317689Right107241131817690Right107251131917691Right107261132017692Right342719214897342819224898325737620531010727808717695Left107281132317696Left107291132417697Left107301132517698Left10731810617699Right107321132617700Right107331132717701Right342919244899343019254900354224376793885613782Left794885713783Right23340041845687225101.01.002920014589166174014150.80.8023280360601M95 405 C95 355 145 305 195 305 C740 305 1447 305 1992 305 C2042 305 2092 355 2092 405 C2092 828 2092 1379 2092 1802 C2092 1852 2042 1902 1992 1902 C1447 1902 740 1902 195 1902 C145 1902 95 1852 95 1802 C95 1379 95 828 95 405 1true61997.01597.02869010035250215519604421201710450187215051523632032140241#FFEEDE418801039