382PathwayNevirapine Metabolism PathwayNevirapine is used in the treatment of human immunodeficiency virus (HIV) type 1 (HIV-1) infection. It is a non-nucleoside reverse transcriptase inhibitor (NNRTI) that binds to the tyrosines at amino acid residues 181 and 188 of HIV-1 reverse transcriptase. Nevirapine is metabolized in the liver to 2-, 3-, 8-, and 12-hydroxynevirapine by the induction of CYP enzymes, mainly CYP3A4 and CYP2B6. 12-hydroxynevirapine may be further oxidated by ALDH to form 4-carboxynevirapine. These hydroxyl metabolites are glucuronidated by UDP glucuronosyl transferases (UGTs), then exit the cell via the adenosine triphosphate-binding cassette gene ABCC10 for urinary excretion.Drug MetabolismPW000618CenterPathwayVisualizationContext68825002360#000099PathwayVisualization375382Nevirapine PathwayNevirapine is used in the treatment of human immunodeficiency virus (HIV) type 1 (HIV-1) infection. It is a non-nucleoside reverse transcriptase inhibitor (NNRTI) that binds to the tyrosines at amino acid residues 181 and 188 of HIV-1 reverse transcriptase. Nevirapine is metabolized in the liver to 2-, 3-, 8-, and 12-hydroxynevirapine by the induction of CYP enzymes, mainly CYP3A4 and CYP2B6. 12-hydroxynevirapine may be further oxidated by ALDH to form 4-carboxynevirapine. These hydroxyl metabolites are glucuronidated by UDP glucuronosyl transferases (UGTs), then exit the cell via the adenosine triphosphate-binding cassette gene ABCC10 for urinary excretion.Drug1669HIV Reverse TranscriptaseInhibitorySubPathway1768[PharmgKB](http://www.pharmgkb.org/pathway/PA165950411)382Pathway188519364830Wen B, Chen Y, Fitch WL: Metabolic activation of nevirapine in human liver microsomes: dehydrogenation and inactivation of cytochrome P450 3A4. Drug Metab Dispos. 2009 Jul;37(7):1557-62. doi: 10.1124/dmd.108.024851. Epub 2009 Apr 13.382Pathway188618729332Chen J, Mannargudi BM, Xu L, Uetrecht J: Demonstration of the metabolic pathway responsible for nevirapine-induced skin rash. Chem Res Toxicol. 2008 Sep;21(9):1862-70. doi: 10.1021/tx800177k. Epub 2008 Aug 26.382Pathway188710421616Riska P, Lamson M, MacGregor T, Sabo J, Hattox S, Pav J, Keirns J: Disposition and biotransformation of the antiretroviral drug nevirapine in humans. Drug Metab Dispos. 1999 Aug;27(8):895-901.382Pathway188822082652Liptrott NJ, Pushpakom S, Wyen C, Fatkenheuer G, Hoffmann C, Mauss S, Knechten H, Brockmeyer NH, Hopper-Borge E, Siccardi M, Back DJ, Khoo SH, Pirmohamed M, Owen A: Association of ABCC10 polymorphisms with nevirapine plasma concentrations in the German Competence Network for HIV/AIDS. Pharmacogenet Genomics. 2012 Jan;22(1):10-9. doi: 10.1097/FPC.0b013e32834dd82e.382Pathway18908452345Cheeseman SH, Hattox SE, McLaughlin MM, Koup RA, Andrews C, Bova CA, Pav JW, Roy T, Sullivan JL, Keirns JJ: Pharmacokinetics of nevirapine: initial single-rising-dose study in humans. Antimicrob Agents Chemother. 1993 Feb;37(2):178-82.382Pathway18917533197Havlir D, Cheeseman SH, McLaughlin M, Murphy R, Erice A, Spector SA, Greenough TC, Sullivan JL, Hall D, Myers M, et al.: High-dose nevirapine: safety, pharmacokinetics, and antiviral effect in patients with human immunodeficiency virus infection. J Infect Dis. 1995 Mar;171(3):537-45.382Pathway1CellCL:00000002Platelet CL:00002334Cardiomyocyte CL:00007465HepatocyteCL:00001823NeuronCL:00005407Epithelial CellCL:00000668Beta cellCL:00006391Homo 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 pombe4896Eukaryote29Saccharomyces cerevisiae (strain ATCC 204508 / S288c)559292EukaryoteBaker's yeast15Plasmodium falciparum5833Eukaryote5CytoplasmGO:00057371CytosolGO:000582920Endoplasmic Reticulum LumenGO:00057886LysosomeGO:00057644PeroxisomeGO:000577713Endoplasmic ReticulumGO:000578310Cell MembraneGO:000588616Lysosomal LumenGO:00432022MitochondrionGO:00057397Endoplasmic Reticulum MembraneGO:000578911Extracellular SpaceGO:00056153Mitochondrial 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:000579421SynapseGO:004520215NucleusGO:000563440PeriplasmGO:00425978Smooth Endoplasmic Reticulum GO:000579027Peroxisome MembraneGO:00057781LiverBTO:00007597292Endothelium BTO:00003934Adrenal MedullaBTO:00000497185cardiocyteBTO:000153928StomachBTO:0001307155268Blood 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is only found in individuals that have used or taken this drug. It is a potent, non-nucleoside reverse transcriptase inhibitor used in combination with nucleoside analogues for treatment of HIV infection and AIDS. [PubChem]Nevirapine binds directly to reverse transcriptase (RT) and blocks the RNA-dependent and DNA-dependent DNA polymerase activities by causing a disruption of the enzyme's catalytic site. The activity of nevirapine does not compete with template or nucleoside triphosphates.129618-40-2C072634463636134308DB00238CC1=C2NC(=O)C3=C(N=CC=C3)N(C3CC3)C2=NC=C1C15H14N4OInChI=1S/C15H14N4O/c1-9-6-8-17-14-12(9)18-15(20)11-3-2-7-16-13(11)19(14)10-4-5-10/h2-3,6-8,10H,4-5H2,1H3,(H,18,20)NQDJXKOVJZTUJA-UHFFFAOYSA-N2-cyclopropyl-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,12,14-hexaen-10-one266.2979266.11676109-3.411nevirapine00Nev;Nvp;11-cyclopropyl-5,11-dihydro-4-methyl-6h-dipyrido(3,2-b:2',3'-e)(1,4)diazepin-6-one;ViramunePW_C008780Nevi38612986493-HydroxynevirapineHMDB00139143-Hydroxynevirapine is only found in individuals that have used or taken Nevirapine. 3-Hydroxynevirapine is a metabolite of Nevirapine. 3-hydroxynevirapine belongs to the family of 1,4-Diazepines. These are organic compounds containing 1,4-diazepine, a seven-member heterocyclic ring with two nitrogen atoms in positions 1 and 4.109789079154108CC1=C2NC(=O)C3=C(N=CC=C3)N(C3CC3)C2=NC=C1OC15H14N4O2InChI=1S/C15H14N4O2/c1-8-11(20)7-17-14-12(8)18-15(21)10-3-2-6-16-13(10)19(14)9-4-5-9/h2-3,6-7,9,20H,4-5H2,1H3,(H,18,21)DANIONWINZEYME-UHFFFAOYSA-N2-cyclopropyl-6-hydroxy-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,12,14-hexaen-10-one282.2973282.111675712-2.7822-cyclopropyl-6-hydroxy-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,12,14-hexaen-10-one00DBMET00077PW_C0086493-HNevp38622986488-HydroxynevirapineHMDB00139138-Hydroxynevirapine is only found in individuals that have used or taken Nevirapine. 8-Hydroxynevirapine is a metabolite of Nevirapine. 8-hydroxynevirapine belongs to the family of 1,4-Diazepines. These are organic compounds containing 1,4-diazepine, a seven-member heterocyclic ring with two nitrogen atoms in positions 1 and 4.107553258930647CC1=C2NC(=O)C3=C(N=CC(O)=C3)N(C3CC3)C2=NC=C1C15H14N4O2InChI=1S/C15H14N4O2/c1-8-4-5-16-14-12(8)18-15(21)11-6-10(20)7-17-13(11)19(14)9-2-3-9/h4-7,9,20H,2-3H2,1H3,(H,18,21)DZPVEPLRIKDBFC-UHFFFAOYSA-N2-cyclopropyl-13-hydroxy-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,12,14-hexaen-10-one282.2973282.111675712-2.8522-cyclopropyl-13-hydroxy-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,12,14-hexaen-10-one00DBMET00076PW_C0086488Hn38642986472-HydroxynevirapineHMDB00139122-Hydroxynevirapine is only found in individuals that have used or taken Nevirapine. 2-Hydroxynevirapine is a metabolite of Nevirapine. 2-hydroxynevirapine belongs to the family of Pyridinones. These are compounds containing a pyridine ring, which bears a ketone.108504619025755CC1=C2NC(=O)C3=C(N=CC=C3)N(C3CC3)C2=NC(O)=C1C15H14N4O2InChI=1S/C15H14N4O2/c1-8-7-11(20)17-14-12(8)18-15(21)10-3-2-6-16-13(10)19(14)9-4-5-9/h2-3,6-7,9H,4-5H2,1H3,(H,17,20)(H,18,21)LFZSOJABLBVGRJ-UHFFFAOYSA-N2-cyclopropyl-5-hydroxy-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,12,14-hexaen-10-one282.2973282.111675712-2.8022-cyclopropyl-5-hydroxy-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,12,14-hexaen-10-one00DBMET00075PW_C0086472HN388029864612-HydroxynevirapineHMDB001391112-Hydroxynevirapine is only found in individuals that have used or taken Nevirapine. 12-Hydroxynevirapine is a metabolite of Nevirapine. 12-hydroxynevirapine belongs to the family of 1,4-Diazepines. These are organic compounds containing 1,4-diazepine, a seven-member heterocyclic ring with two nitrogen atoms in positions 1 and 4.453338155605399285OCC1=C2NC(=O)C3=C(N=CC=C3)N(C3CC3)C2=NC=C1C15H14N4O2InChI=1S/C15H14N4O2/c20-8-9-5-7-17-14-12(9)18-15(21)11-2-1-6-16-13(11)19(14)10-3-4-10/h1-2,5-7,10,20H,3-4,8H2,(H,18,21)SEBABOMFNCVZGF-UHFFFAOYSA-N2-cyclopropyl-7-(hydroxymethyl)-2,4,9,15-tetraazatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,12,14-hexaen-10-one282.2973282.111675712-2.6122-cyclopropyl-7-(hydroxymethyl)-2,4,9,15-tetraazatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,12,14-hexaen-10-one00DBMET00074PW_C00864612-Hnvp388129406083-Hydroxynevirapine glucuronideHMDB00607433-Hydroxynevirapine glucuronide is a metabolite of nevirapine. Nevirapine, also marketed under the trade name Viramune, is a non-nucleoside reverse transcriptase inhibitor (NNRTI) used to treat HIV-1 infection and AIDS. As with other antiretroviral drugs, HIV rapidly develops resistance if nevirapine is used alone, so recommended therapy consists of combinations of three or more antiretrovirals. (Wikipedia)CC1=C2N=C(OC3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)C3=C(N=CC=C3)N(C3CC3)C2=NC=C1OC21H22N4O8InChI=1S/C21H22N4O8/c1-8-11(26)7-23-18-12(8)24-19(10-3-2-6-22-17(10)25(18)9-4-5-9)33-21-15(29)13(27)14(28)16(32-21)20(30)31/h2-3,6-7,9,13-16,21,26-29H,4-5H2,1H3,(H,30,31)/t13-,14-,15+,16-,21?/m0/s1GDAAYOYNGMRKSI-IQSUWLOCSA-N(2S,3S,4S,5R)-6-({2-cyclopropyl-6-hydroxy-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,9,12,14-heptaen-10-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid458.4214458.1437637-2.515(2S,3S,4S,5R)-6-({2-cyclopropyl-6-hydroxy-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,9,12,14-heptaen-10-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid0-1DBMET00712PW_C0406083HnpGlu38852939203139212484536406108-Hydroxynevirapine glucuronideHMDB00611308-Hydroxynevirapine glucuronide is a metabolite of nevirapine. Nevirapine, also marketed under the trade name Viramune, is a non-nucleoside reverse transcriptase inhibitor (NNRTI) used to treat HIV-1 infection and AIDS. As with other antiretroviral drugs, HIV rapidly develops resistance if nevirapine is used alone, so recommended therapy consists of combinations of three or more antiretrovirals. (Wikipedia)30778632CC1=CC=NC2=C1NC(=O)C1=C(N=CC(O[C@H]3O[C@H]([C@H](O)[C@@H](O)[C@@H]3O)C(O)=O)=C1)N2C1CC1C21H22N4O8InChI=1S/C21H22N4O8/c1-8-4-5-22-18-12(8)24-19(29)11-6-10(7-23-17(11)25(18)9-2-3-9)32-21-15(28)13(26)14(27)16(33-21)20(30)31/h4-7,9,13-16,21,26-28H,2-3H2,1H3,(H,24,29)(H,30,31)/t13-,14-,15+,16-,21+/m1/s1IVZWGLRSSHUFTI-WCYOCWRHSA-N(2R,3R,4R,5S,6R)-6-({2-cyclopropyl-7-methyl-10-oxo-2,4,9,15-tetraazatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,12,14-hexaen-13-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid458.4214458.1437637-2.095(2R,3R,4R,5S,6R)-6-({2-cyclopropyl-7-methyl-10-oxo-2,4,9,15-tetraazatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,12,14-hexaen-13-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid0-1DBMET00779PW_C0406108HnG39042939223139232484836406072-Hydroxynevirapine glucuronideHMDB00607202-Hydroxynevirapine glucuronide is a metabolite of nevirapine. Nevirapine, also marketed under the trade name Viramune, is a non-nucleoside reverse transcriptase inhibitor (NNRTI) used to treat HIV-1 infection and AIDS. As with other antiretroviral drugs, HIV rapidly develops resistance if nevirapine is used alone, so recommended therapy consists of combinations of three or more antiretrovirals. (Wikipedia)30778582CC1=CC(O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)=NC2=C1N=C(O)C1=C(N=CC=C1)N2C1CC1C21H22N4O8InChI=1S/C21H22N4O8/c1-8-7-11(32-21-15(28)13(26)14(27)16(33-21)20(30)31)23-18-12(8)24-19(29)10-3-2-6-22-17(10)25(18)9-4-5-9/h2-3,6-7,9,13-16,21,26-28H,4-5H2,1H3,(H,24,29)(H,30,31)/t13-,14-,15+,16-,21+/m0/s1RNMZKTLILDCQOC-KUSYAZKWSA-N(2S,3S,4S,5R,6S)-6-({2-cyclopropyl-10-hydroxy-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-5-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid458.4214458.1437637-2.525(2S,3S,4S,5R,6S)-6-({2-cyclopropyl-10-hydroxy-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-5-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid0-1DBMET00685PW_C0406072hng390729392431392524849364060612-Hydroxynevirapine glucuronideHMDB006070512-Hydroxynevirapine glucuronide is a metabolite of nevirapine. Nevirapine, also marketed under the trade name Viramune, is a non-nucleoside reverse transcriptase inhibitor (NNRTI) used to treat HIV-1 infection and AIDS. As with other antiretroviral drugs, HIV rapidly develops resistance if nevirapine is used alone, so recommended therapy consists of combinations of three or more antiretrovirals. (Wikipedia)CC1=C2N=C(OC3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)C3=C(N=CC=C3)N(C3CC3O)C2=NC=C1C21H22N4O8InChI=1S/C21H22N4O8/c1-8-4-6-23-18-12(8)24-19(9-3-2-5-22-17(9)25(18)10-7-11(10)26)33-21-15(29)13(27)14(28)16(32-21)20(30)31/h2-6,10-11,13-16,21,26-29H,7H2,1H3,(H,30,31)/t10?,11?,13-,14-,15+,16-,21?/m0/s1UVZMQJUCOZEMQZ-RDPCRGLVSA-N(2S,3S,4S,5R)-3,4,5-trihydroxy-6-{[2-(2-hydroxycyclopropyl)-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,9,12,14-heptaen-10-yl]oxy}oxane-2-carboxylic acid458.4214458.1437637-2.505(2S,3S,4S,5R)-3,4,5-trihydroxy-6-{[2-(2-hydroxycyclopropyl)-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,9,12,14-heptaen-10-yl]oxy}oxane-2-carboxylic acid0-1DBMET00669PW_C04060612HG390829392631392724850361065OxygenHMDB0001377Oxygen 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_C001799Heme247163081032486082766512443135449141336196318280629293893238113367263421143734440433148232851709554721235485125551712958301416246786283165971517044160706016173262131183519811898211120651641300929813021300422781776915293769312497735111177364130773673317739833277517115776293367781333478380133786021327896311279932134120431405120603408120955407121085383121658429121746124121910122122570406122691384123065376123133447123144136123228374123521119123650398124216464124297118124463135125142120125277121125742482125896481126196299126499297126512495126718479126827480127224502127357206127632388128070205128083395128086390128309501128434391746Uridine diphosphate glucuronic acidHMDB0000935Uridine diphosphate glucuronic acid is a nucleoside diphosphate sugar which serves as a source of glucuronic acid for polysaccharide biosynthesis. It may also be epimerized to UDP Iduronic acid, which donates Iduronic acid to polysaccharides. In animals, UDP glucuronic acid is used for formation of many glucosiduronides with various aglycones. The transfer of glucuronic acid from UDP-alpha-D-glucuronic acid onto a terminal galactose residue is done by beta1,3-glucuronosyltransferases, responsible for the completion of the protein-glycosaminoglycan linkage region of proteoglycans and of the HNK1 epitope of glycoproteins and glycolipids. In humans the enzyme galactose-beta-1,3-glucuronosyltransferase I completes the synthesis of the common linker region of glycosaminoglycans (GAGs) by transferring glucuronic acid (GlcA) onto the terminal galactose of the glycopeptide primer of proteoglycans. The GAG chains of proteoglycans regulate major biological processes such as cell proliferation and recognition, extracellular matrix deposition, and morphogenesis. (PMID: 16815917).2616-64-0C001671747317200UDP-GLUCURONATE16522O[C@@H]1[C@@H](COP(O)(=O)OP(O)(=O)O[C@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)O[C@H]([C@@H]1O)N1C=CC(=O)NC1=OC15H22N2O18P2InChI=1S/C15H22N2O18P2/c18-5-1-2-17(15(26)16-5)12-9(22)6(19)4(32-12)3-31-36(27,28)35-37(29,30)34-14-10(23)7(20)8(21)11(33-14)13(24)25/h1-2,4,6-12,14,19-23H,3H2,(H,24,25)(H,27,28)(H,29,30)(H,16,18,26)/t4-,6-,7+,8+,9-,10-,11+,12-,14-/m1/s1HDYANYHVCAPMJV-LXQIFKJMSA-N(2S,3S,4S,5R,6R)-6-({[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid580.2853580.034284934-1.519udp-α-D-glucuronic acid0-3FDB022325Glucopyranuronic acid 1-ester with uridine 5'-pyrophosphate;Udp glucuronate;Udp glucuronic acid;Udp-d-glucuronate;Udp-d-glucuronic acid;Udp-glcua;Udp-glucuronate;Udp-glucuronic acid;Udp-alpha-d-glucuronate;Udp-alpha-delta-glucuronate;Udp-delta-glucuronate;Udp-delta-glucuronic acid;Udpga;Udpglucuronate;Uga;Uridine 5'-[3-(d-glucopyranosyloxyuronic acid) dihydrogen diphosphate];Uridine 5'-diphospho-a-d-glucuronate;Uridine 5'-diphospho-a-d-glucuronic acid;Uridine 5'-diphospho-alpha-delta-glucuronate;Uridine 5'-diphospho-alpha-delta-glucuronic acid;Uridine 5'-diphospho-glucuronic acid;Uridine 5'-diphosphoglucuronate;Uridine 5'-diphosphoglucuronic acid;Uridine diphosphate glucuronate;Uridine diphosphate glucuronic acid;Uridine diphosphate-glucuronate;Uridine diphospho-d-glucuronate;Uridine diphospho-d-glucuronic acid;Uridine diphospho-delta-glucuronate;Uridine diphospho-delta-glucuronic acid;Uridine diphosphoglucuronate;Uridine diphosphoglucuronic acid;Uridine pyrophosphoglucuronate;Uridine pyrophosphoglucuronic acid;Uridinediphosphoglucuronic acid;A-d-glucopyranuronic acid 1->5'-ester with uridine 5'-(trihydrogen pyrophosphate);A-d-glucopyranuronic acid ester with uridine 5'-pyrophosphate;Alpha-d-glucopyranuronic acid 1-p'-ester with uridine 5'-(trihydrogen diphosphate);Alpha-delta-glucopyranuronic acid 1->5'-ester with uridine 5'-(trihydrogen pyrophosphate);Alpha-delta-glucopyranuronic acid 1-p'-ester with uridine 5'-(trihydrogen diphosphate);Alpha-delta-glucopyranuronic acid ester with uridine 5'-pyrophosphate;Uridine-5'-diphosphate-glucuronic acid;Udp-a-d-glucuronate;Udp-a-d-glucuronic acid;Udp-α-d-glucuronate;Udp-α-d-glucuronic acid;Udpglucuronic acid;Uridine diphosphoric acid glucuronic acid;Uridine-5'-diphosphate-glucuronate;Uridine-5'-diphosphoric acid-glucuronic acidPW_C000746UDPGlcA112982219492303223519447918451610484436494492517695552513058321417055160773583317840311178615132120830122122049124122338383123415135124603118124889398125821297126201299126506495127274205128078390201Uridine 5'-diphosphateHMDB0000295Uridine 5'-diphosphate is a uracil nucleotide containing a pyrophosphate group esterified to C5 of the sugar moiety. UDP is an important extracellular pyrimidine signaling molecule that mediates diverse biological effects via P1 and P2 purinergic receptors, such as the uptake of thymidine and proliferation of gliomas. (PMID: 14558596). UDP induces intracellular Ca(2+) responses and oscillations in HeLa cells, due to the activation of P2Ys (G-protein coupled ATP receptors). (PMID: 1257952).58-98-0C00015603117659UDP5809DB03435O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(=O)OP(O)(O)=O)N1C=CC(=O)NC1=OC9H14N2O12P2InChI=1S/C9H14N2O12P2/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(22-8)3-21-25(19,20)23-24(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1XCCTYIAWTASOJW-XVFCMESISA-N[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid404.1612404.002196946-1.666UDP0-2FDB0075095'-udp;Udp;Uridine 5'-diphosphate;Uridine 5'-pyrophosphate;Uridine 5'-pyrophosphorate;Uridine 5'-pyrophosphoric acid;Uridine diphosphate;Uridine pyrophosphate;Uridine 5'-diphosphoric acid;Uridine diphosphoric acidPW_C000201UDP41081517215454321974923529311529446318451810484636494692517895552713058341417057160724621372482147287210843315111913164126152257730411177360331779243367825513278264356120315122121252429121365124121375419122101383122378125122970135123822464123924118123934455124652398124932136125643297126038299126048490126257495127490388127500507127820390406094-CarboxynevirapineHMDB00607594-Carboxynevirapine is a metabolite of nevirapine. Nevirapine, also marketed under the trade name Viramune, is a non-nucleoside reverse transcriptase inhibitor (NNRTI) used to treat HIV-1 infection and AIDS. As with other antiretroviral drugs, HIV rapidly develops resistance if nevirapine is used alone, so recommended therapy consists of combinations of three or more antiretrovirals. (Wikipedia)107090358884376OC(=O)C1=CC=NC2=C1NC(=O)C1=CC=CN=C1N2C1CC1C15H12N4O3InChI=1S/C15H12N4O3/c20-14-10-2-1-6-16-12(10)19(8-3-4-8)13-11(18-14)9(15(21)22)5-7-17-13/h1-2,5-8H,3-4H2,(H,18,20)(H,21,22)WDXCMIDQWGYHIN-UHFFFAOYSA-N2-cyclopropyl-10-oxo-2,4,9,15-tetraazatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaene-7-carboxylic acid296.2808296.09094027-2.7622-cyclopropyl-10-oxo-2,4,9,15-tetraazatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaene-7-carboxylic acid0-1DBMET00727PW_C0406094-Cnevp3909294851311783Hydrogen peroxideHMDB0003125Hydrogen peroxide (H2O2) is a very pale blue liquid which appears colourless in a dilute solution, slightly more viscous than water. It is a weak acid. It has strong oxidizing properties and is therefore a powerful bleaching agent that is mostly used for bleaching paper, but has also found use as a disinfectant and as an oxidizer. Hydrogen peroxide in the form of carbamide peroxide is widely used for tooth whitening (bleaching), both in professionally- and in self-administered products. Hydrogen peroxide (H2O2) is a well-documented component of living cells. It plays important roles in host defense and oxidative biosynthetic reactions. In addition there is growing evidence that at low levels, H2O2 also functions as a signaling agent, particularly in higher organisms. H2O2 has increasingly been viewed as an important cellular signaling agent in its own right, capable of modulating both contractile and growth-promoting pathways with more far-reaching effects. Due to the accumulation of hydrogen peroxide in the skin of patients with the depigmentation disorder vitiligo, the human epidermis cannot have the normal capacity for autocrine synthesis, transport and degradation of acetylcholine as well as the muscarinic (m1-m5) and nicotinic signal transduction in keratinocytes and melanocytes. Accumulating evidence suggests that hydrogen peroxide (H(2)O(2)) plays an important role in cancer development. Experimental data have shown that cancer cells produce high amounts of H(2)O(2). An increase in the cellular levels of H(2)O(2) has been linked to several key alterations in cancer, including DNA alterations, cell proliferation, apoptosis resistance, metastasis, angiogenesis and hypoxia-inducible factor 1 (HIF-1) activation. (PMID: 17150302, 17335854, 16677071, 16607324, 16514169).7722-84-1C0002778416240HYDROGEN-PEROXIDE763OOH2O2InChI=1S/H2O2/c1-2/h1-2HMHAJPDPJQMAIIY-UHFFFAOYSA-Nperoxol34.014734.0054793082hydrogen peroxide00FDB014562Adeka super el;Albone;Albone 35;Albone ds;Anti-keim 50;Asepticper;Baquashock;Cix;Clarigel gold;Crestal whitestrips;Crystacide;Dentasept;Deslime lp;Hioxyl;Hipox;Hybrite;Hydrogen dioxide;Hydrogen peroxide;Inhibine;Lase peroxide;Lensan a;Magic bleaching;Metrokur;Mirasept;Nite white excel 2;Odosat d;Opalescence xtra;Oxigenal;Oxydol;Oxyfull;Oxysept;Oxysept i;Pegasyl;Perhydrol;Perone;Peroxaan;Peroxclean;Quasar brite;Select bleach;Superoxol;T-stuff;Whiteness hp;Whitespeed;Xtra white;[oh(oh)];Dihydrogen dioxide;H2o2;HoohPW_C001783H2O29891135188855114627287551512433169121749512534223818104749134752315495126550212355101275810108600514770381638396151118172161188621512461226127092911271929213028301130352981304030213405222426583157702222577047294770792937750011377540334775981157772033277725337778061147781011177819326780733297815213278598112120050408120102122120463405120595409120609416120954407121047124122120382122801374122814443122839135123097376123157447123165448123220137123234452123520119123611118124672399125428482125469297125709478125732483125748488125895481126103299126275484126967502126978207127006205127201209127215208127230505127356206127601388127838389414Adenosine triphosphateHMDB0000538Adenosine triphosphate (ATP) is a nucleotide consisting of a purine base (adenine) attached to the first carbon atom of ribose (a pentose sugar). Three phosphate groups are esterified at the fifth carbon atom of the ribose. ATP is incorporated into nucleic acids by polymerases in the processes of DNA replication and transcription. ATP contributes to cellular energy charge and participates in overall energy balance, maintaining cellular homeostasis. ATP can act as an extracellular signaling molecule via interactions with specific purinergic receptors to mediate a wide variety of processes as diverse as neurotransmission, inflammation, apoptosis, and bone remodelling. Extracellular ATP and its metabolite adenosine have also been shown to exert a variety of effects on nearly every cell type in human skin, and ATP seems to play a direct role in triggering skin inflammatory, regenerative, and fibrotic responses to mechanical injury, an indirect role in melanocyte proliferation and apoptosis, and a complex role in Langerhans cell-directed adaptive immunity. During exercise, intracellular homeostasis depends on the matching of adenosine triphosphate (ATP) supply and ATP demand. Metabolites play a useful role in communicating the extent of ATP demand to the metabolic supply pathways. Effects as different as proliferation or differentiation, chemotaxis, release of cytokines or lysosomal constituents, and generation of reactive oxygen or nitrogen species are elicited upon stimulation of blood cells with extracellular ATP. The increased concentration of adenosine triphosphate (ATP) in erythrocytes from patients with chronic renal failure (CRF) has been observed in many studies but the mechanism leading to these abnormalities still is controversial. (PMID: 15490415, 15129319, 14707763, 14696970, 11157473).56-65-5C00002595715422ATP5742DB00171NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1OC10H16N5O13P3InChI=1S/C10H16N5O13P3/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(26-10)1-25-30(21,22)28-31(23,24)27-29(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H,23,24)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1ZKHQWZAMYRWXGA-KQYNXXCUSA-N({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid507.181506.995745159-2.057adenosine triphosphate0-3FDB0218135'-(tetrahydrogen triphosphate) adenosine;5'-atp;Atp;Adenosine 5'-triphosphate;Adenosine 5'-triphosphorate;Adenosine 5'-triphosphoric acid;Adenosine triphosphate;Adenylpyrophosphorate;Adenylpyrophosphoric acid;Adephos;Adetol;Adynol;Atipi;Atriphos;Cardenosine;Fosfobion;Glucobasin;Myotriphos;Phosphobion;Striadyne;Triadenyl;Triphosphaden;Triphosphoric acid adenosine ester;Adenosine-5'-triphosphate;H4atp;Adenosine triphosphoric acid;Adenosine-5'-triphosphoric acidPW_C000414ATP922146082661641422478137333279959343997632105182112102146492156142160582405592434272726462812293029663163723616613617514399234474314768914864545032895035265155752059752151005250104529110153131115346112539010354061175430118544312055421295556132556913356031355621108584614358541465876107589714759241516048155610916162301666493178683918868701606976199715720571842067209210722521372292117298198730221673902177408218743216374812227499190818622511847277119031701201028112039164121782851257822612691290132642231532730842326315426213224269431877028253772181347723332977468333776323367803733278041350781681287821435178240353784113357849411578850130788653317891933480028368800461848067411985629194826124113234941132823881162801091199141221199924061201544071202453821203624121212464291213921231213974331214714081219744101220651251220793831220834051224024221224444351229193991230094461238164641239514471239564681240293741245274441246161361246303981246343761249434721249723751250114701253042971253714791253922991255154811255954841261234851262203001262344951262404781265474911265964991269135011271233891277315161277813951277963901278012091281195081281675171034Adenosine diphosphateHMDB0001341Adenosine diphosphate, abbreviated ADP, is a nucleotide. It is an ester of pyrophosphoric acid with the nucleotide adenine. ADP consists of the pyrophosphate group, the pentose sugar ribose, and the nucleobase adenine. ADP is the product of ATP dephosphorylation by ATPases. ADP is converted back to ATP by ATP synthases.58-64-0C00008602216761ADP5800NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1OC10H15N5O10P2InChI=1S/C10H15N5O10P2/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(24-10)1-23-27(21,22)25-26(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1XTWYTFMLZFPYCI-KQYNXXCUSA-N[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid427.2011427.029414749-2.126adenosine-diphosphate0-2FDB021817Adp;Adenosindiphosphorsaeure;Adenosine 5'-pyrophosphate;Adenosine diphosphate;Adenosine pyrophosphate;Adenosine-5'-diphosphate;Adenosine-5-diphosphate;Adenosine-diphosphate;5'-adenylphosphoric acid;Adenosine 5'-diphosphate;H3adp;5'-adenylphosphate;Adenosine 5'-diphosphoric acid;Adenosine-5'-diphosphoric acidPW_C001034ADP2341348415224821380159631597831061141518219014921041821131021615824085924352727284727364628552931657236356144002344763147709150362651577520897521710053151115349112539210354461205544129557213356241085741117576410158491435856146587810758991475926151605015561111616231166649517867009468411886872160715920571872067208210722621372312117300198730321673912177410218743316374832228187225118512771190517012013281121802851326222315329308423283154239831342622322426963187702925377087132772161347730632977472333776633367803933278043350781701287821535178244353784143357849511578705331788491307892033480030368806221188065113580676119948271241132833881162041091199441221199944061201564071203183821203664121212484291213941231213994331214724081218993831219764101220641251220854051224054221224454351229733991230134461238184641239534471239584681240303741244523981245294441246151361246363761249474721249753751250124701253342971253734791254922991255174811256454841261254851262193001262354951262424781265504911265974991269155011277335161277803951277973901278032091281225081281685171283133891104PhosphateHMDB0001429Phosphate is a salt of phosphoric acid. In organic chemistry, a phosphate, or organophosphate, is an ester of phosphoric acid. Organic phosphates are important in biochemistry, biogeochemistry and ecology. Phosphate (Pi) is an essential component of life. In biological systems, phosphorus is found as a free phosphate ion in solution and is called inorganic phosphate, to distinguish it from phosphates bound in various phosphate esters. Inorganic phosphate is generally denoted Pi and at physiological (neutral) pH primarily consists of a mixture of HPO<sup>2-</sup><sub>4</sub> and H<sub>2</sub>PO<sup>-</sup><sub>4</sub> ions. phosphates are most commonly found in the form of adenosine phosphates, (AMP, ADP and ATP) and in DNA and RNA and can be released by the hydrolysis of ATP or ADP. Similar reactions exist for the other nucleoside diphosphates and triphosphates. Phosphoanhydride bonds in ADP and ATP, or other nucleoside diphosphates and triphosphates, contain high amounts of energy which give them their vital role in all living organisms. Phosphate must be actively transported into cells against its electrochemical gradient. In vertebrates, two unrelated families of Na+-dependent Pi transporters carry out this task. Remarkably, the two families transport different Pi species: whereas type II Na+/Pi cotransporters (SCL34) prefer divalent HPO4(2), type III Na+/Pi cotransporters (SLC20) transport monovalent H2PO4. The SCL34 family comprises both electrogenic and electroneutral members that are expressed in various epithelia and other polarized cells. Through regulated activity in apical membranes of the gut and kidney, they maintain body Pi homeostasis, and in salivary and mammary glands, liver, and testes they play a role in modulating the Pi content of luminal fluids. Phosphate levels in the blood play an important role in hormone signaling and in bone homeostasis. In classical endocrine regulation, low serum phosphate induces the renal production of the seco-steroid hormone 1,25-dihydroxyvitamin D3 (1,25(OH)2D3).This active metabolite of vitamin D acts to restore circulating mineral (i.e. phosphate and calcium) levels by increasing absorption in the intestine, reabsorption in the kidney, and mobilization of calcium and phosphate from bone. Thus, chronic renal failure is associated with hyperparathyroidism, which in turn contributes to osteomalacia (softening of the bones). Another complication of chronic renal failure is hyperphosphatemia (low levels of phosphate in the blood). Hyperphosphatemia (excess levels of phosphate in the blood) is a prevalent condition in kidney dialysis patients and is associated with increased risk of mortality. Hypophosphatemia (hungry bone syndrome) has been associated to postoperative electrolyte aberrations and after parathyroidectomy. (PMID: 17581921, 11169009, 11039261, 9159312, 17625581)Fibroblast growth factor 23 (FGF-23) has recently been recognized as a key mediator of phosphate homeostasis, its most notable effect being promotion of phosphate excretion. FGF-23 was discovered to be involved in diseases such as autosomal dominant hypophosphatemic rickets, X-linked hypophosphatemia, and tumor-induced osteomalacia in which phosphate wasting was coupled to inappropriately low levels of 1,25(OH)2D3. FGF-23 is regulated by dietary phosphate in humans. In particular it was found that phosphate restriction decreased FGF-23, and phosphate loading increased FGF-23.14265-44-2C00009106118367CPD-85871032[O-]P([O-])([O-])=OO4PInChI=1S/H3O4P/c1-5(2,3)4/h(H3,1,2,3,4)/p-3NBIIXXVUZAFLBC-UHFFFAOYSA-Kphosphoric acid94.971494.953423phosphoric acid0-2DBMET00532FDB022617Nfb orthophosphate;O-phosphoric acid;Ortho-phosphate;Orthophosphate (po43-);Orthophosphate(3-);Phosphate;Phosphate (po43-);Phosphate anion(3-);Phosphate ion (po43-);Phosphate ion(3-);Phosphate trianion;Phosphate(3-);Phosphoric acid ion(3-);Pi;[po4](3-);Orthophosphate;Phosphate ion;Po4(3-);Phosphoric acid;Orthophosphoric acid;Phosphoric acid ionPW_C001104Pi24484881458181883129803176314176749250010272947273746312929316672363661385123424922447531503127515875207975216100531711153511125381103544712055431295573133560513556251085693658481435855146591114759411516040155610016162941076487178669110167141176842188688916071612057189206721221173061987389210740221274361637475222819622582582271011824110134257117481321176111511773213119041701192716412014281127282901326322334819174225530442350315424353184369232277018253771942937721713477940336779661307804833278057329782453537866933180022368892793089383138394796384110558390110640391113235941158453981162061091199824061200691221206994071210571241212161251212684291213521211214091231214233821218524051233041191236211181237861361238384641239684471239813991244053761249484721253624791254462971257744811259542991262214781265943001266042981267234841269045011274133881277832091281663951281775131283153895730Multidrug resistance-associated protein 7Q5T3U5
ATP-dependent transporter probably involved in cellular detoxification through lipophilic anion extrusion.
ABCC10AY03259913141141441Cytochrome 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.-1384493270233572934231434341045801813656836956Cytochrome P450 3A4P08684Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
HMDBP01018CYP3A47q21.1M1890711.14.13.-; 1.14.13.157; 1.14.13.32; 1.14.13.67; 1.14.13.9729332932722329010336826404531457718517495135698615136000332136017491360183311436Cytochrome P450 2D6P10635Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
HMDBP01548CYP2D622q13.1DQ28214411.14.14.132391134162636252938002404831405110457918517395628411442Cytochrome P450 3A5P20815Cytochromes 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.
HMDBP01554CYP3A57q21.1CH23695611.14.14.1293429327323369263436104044314590184339549135699615136001332973Cytochrome 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; 1.14.13.4933562934351038462404631481018481618469UDP-glucuronosyltransferase 1-10Q9HAW8UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
HMDBP00487UGT1A102q37U8950812.4.1.17365629397977406331427410444960448018484736194Retinal dehydrogenase 1P00352Binds free retinal and cellular retinol-binding protein-bound retinal. Can convert/oxidize retinaldehyde to retinoic acid (By similarity).
HMDBP00199ALDH1A19q21.13M3198211.2.1.36324423398834017375829485231764Multidrug resistance-associated protein 71PW_P00076486157301384Cytochrome P450 2B61PW_P0003844061441118017991730Cytochrome P450 3A41PW_P000730824956132517991292910802Cytochrome P450 2D61PW_P0008029071436134417991731Cytochrome P450 3A51PW_P0007318251442132617991293010820Cytochrome P450 2C91PW_P000820944973135117991890UDP-glucuronosyltransferase 1-101PW_P00089010154691803Retinal dehydrogenase 11PW_P00080390819441984falsePW_R001984Right718187801Compoundfalse867010651Compoundtrue86711461Compoundtrue8672400341Compoundtrue718286491Compoundfalse867314201Compoundtrue86741431Compoundtrue18283841.14.13.-1983falsePW_R001983Right717987801Compoundfalse867510651Compoundtrue86761461Compoundtrue8677400341Compoundtrue718086481Compoundfalse867814201Compoundtrue86791431Compoundtrue182573018263841.14.13.-18278021.14.14.11982falsePW_R001982Right717787801Compoundfalse868010651Compoundtrue86811461Compoundtrue8682400341Compoundtrue717886471Compoundfalse868314201Compoundtrue86841431Compoundtrue182373018247311.14.14.11981falsePW_R001981Right717587801Compoundfalse868510651Compoundtrue86861461Compoundtrue8687400341Compoundtrue717686461Compoundfalse868814201Compoundtrue86891431Compoundtrue181973018207311.14.14.1182182018228021.14.14.11985falsePW_R001985Right718386491Compoundfalse86907461Compoundtrue7184406081Compoundfalse86912011Compoundtrue18558902.4.1.171986falsePW_R001986Right718586481Compoundfalse86927461Compoundtrue7186406101Compoundfalse86932011Compoundtrue18568902.4.1.171987falsePW_R001987Right718786471Compoundfalse86947461Compoundtrue7188406071Compoundfalse86952011Compoundtrue18588902.4.1.171988falsePW_R001988Right718986461Compoundfalse86967461Compoundtrue7190406061Compoundfalse86972011Compoundtrue18578902.4.1.171989falsePW_R001989Right719186461Compoundfalse869814201Compoundtrue869910651Compoundtrue7192406091Compoundfalse870017831Compoundtrue18338031.2.1.3659PW_RCT000059Right3495940610Compound13135059414Compound131351591420Compound1313525940610Compound115353591034Compound131354591104Compound1315960PW_RCT000060Right3556040608Compound13135660414Compound131357601420Compound1313586040608Compound115359601034Compound131360601104Compound1316058PW_RCT000058Right3435840607Compound13134458414Compound131345581420Compound1313465840607Compound115347581034Compound131348581104Compound1315857PW_RCT000057Right3375740606Compound13133857414Compound131339571420Compound1313405740606Compound115341571034Compound131342571104Compound13157184PW_T000184216406081Compound312Right1397642013-09-11T16:27:47-06:002013-09-11T16:27:47-06:0053186PW_T000186218406101Compound312Right1417642013-09-11T16:30:16-06:002013-09-11T16:30:16-06:0053183PW_T000183215406071Compound312Right1387642013-09-11T16:25:01-06:002013-09-11T16:25:01-06:0053185PW_T000185217406061Compound312Right1407642013-09-11T16:29:40-06:002013-09-11T16:29:40-06:00537819878029157false82531010regular2001907820864929157false240106510regular2001907828864829157false605106510regular2001907837864729157false1065105510regular2001907840864629157false1465105510regular20019078874060831157true255116510regular2002007888406082157false245220510regular200200789540610313true0010regular1001207896406102157false605220510regular200200789740607313true0010regular1001207898406072157false1065220510regular200200790140606313true0010regular1001207902406062157false1470220010regular2002001075110651065false42061610regular7878107521461062false19771010regular503010753400341055false18361610regular78781075414201049false18589510regular7878107551431061false41591510regular5030107561799109false22977510regular100251076010651065false78061610regular7878107611461062false55771510regular503010762400341055false54361610regular78781076314201049false78589510regular7878107641431061false56091510regular5030107651799109false59478010regular10025107661799109false46982510regular10025107671799109false83473010regular100251077110651065false123061610regular7878107721461062false101771010regular503010773400341055false100361610regular78781077414201049false123089510regular7878107751431061false102092510regular5030107761799109false96977510regular10025107771799109false125477510regular100251077810651065false139061610regular7878107791461062false166767510regular503010780400341055false165358610regular78781078114201049false165592010regular7878107821431061false141593010regular5030107831799109false136973210regular10025107841799109false165472710regular10025107851799109false136987210regular10025107861799109false165487210regular1002510787746363false155128010regular100130107884060836157false245164510regular20020010789201363false155151510regular10011010790746363false525128010regular100130107914061036157false605164510regular20020010792201363false525151510regular10011010793746363false980128010regular100130107944060736157false1065164510regular20020010795201363false985151510regular10011010796746363false1385128010regular100130107974060636157false1470164510regular20020010798201363false1390151510regular1001101079914203149false1922122010regular78781080010653165false2058130110regular7878108014060931157false1862164510regular2001901080217833156false2063152610regular7878108064143142false560192510regular50301080714203149false790190010regular78781080810343143false561213010regular50301080911043146false804211810regular4443108104143142false195192510regular50301081114203149false435190010regular78781081210343143false196213010regular50301081311043146false444211810regular4443108144143142f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1845 C345 1875 345 1975 345 2005 83false1811836M345 2205 C345 2175 345 2105 345 2075 83false18trueM 297.5 1582.0096189432334 L 305 1595 L 312.5 1582.0096189432334false11847M705 2075 C706 2091 704 2186 705 2205 83false18trueM 696.8276070098425 1582.4217651153103 L 705 1595 L 711.8068744498302 1581.6333826184689false11848M705 1845 C706 1863 705 1989 705 2005 83false1811849M1165 2075 C1166 2094 1165 2184 1165 2205 83false18trueM 1182.5 1577.0096189432334 L 1190 1590 L 1197.5 1577.0096189432334false11850M1165 1845 C1166 1863 1165 1986 1165 2005 83false1811851M1570 2075 C1570 2095 1571 2182 1570 2200 83false18trueM 1348.2321240430822 1571.613594394619 L 1355 1585 L 1363.2090293411634 1572.445644688957false11852M1570 1845 C1570 1864 1570 1986 1570 2005 83false1811938M1025 405 C1044 405 1306 405 1325 405 148false18falsetrueM 1085 410 L 1085 395 L 1085 38016890M825 405 C755 408 333 569 339 780 5false1816891M420 655 C393 656 338 750 339 780 5false1816892M247 725 C269 725 339 750 339 780 5false1816893M261 655 C293 656 339 750 339 780 5false1816894M340 1065 C340 1035 339 880 339 850 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false16895M263 934 C294 933 339 880 339 850 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false16896M415 930 C387 930 339 880 339 850 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false16897M150 150 L150 200 L200 150 z10true1816902M825 405 C800 405 702 541 704 785 5false1816903M780 655 C750 656 704 755 704 785 5false1816904M607 730 C636 729 704 755 704 785 5false1816905M621 655 C646 655 704 755 704 785 5false1816906M705 1065 C705 1035 704 885 704 855 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false16907M785 934 C754 933 704 885 704 855 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false16908M610 930 C639 928 704 885 704 855 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false16909M150 150 L150 200 L200 150 z10true1816910M150 150 L150 200 L200 150 z10true1816911M150 150 L150 200 L200 150 z10true1816916M1025 405 C1057 404 1155 544 1161 813 5false1816917M1230 655 C1200 655 1161 772 1161 815 5false1816918M1067 725 C1092 724 1159 755 1161 814 5false1816919M1081 655 C1108 655 1161 787 1161 814 5false1816920M1165 1055 C1165 1025 1164 842 1161 815 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false16921M1230 934 C1197 933 1162 858 1161 815 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false16922M1070 940 C1096 939 1162 859 1161 815 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false16923M150 150 L150 200 L200 150 z10true1816924M150 150 L150 200 L200 150 z10true1816925M1025 405 C1198 407 1555 500.5 1561 812.5 5false1816926M1468 655 C1529 655 1557 730.5 1562 810.5 5false1816927M1667 690 C1645 689 1559 679.5 1561 812.5 5false1816928M1653 625 C1627 625 1560 681.5 1561 812.5 5false1816929M1565 1055 C1565 1025 1560 830.5 1561 811.5 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false16930M1655 959 C1606 953 1564 918.5 1561 812.5 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false16931M1465 945 C1509 943 1564 917.5 1561 813.5 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false16932M150 150 L150 200 L200 150 z10true1816933M150 150 L150 200 L200 150 z10true1816934M150 150 L150 200 L200 150 z10true1816935M150 150 L150 200 L200 150 z10true1816936M340 1255 C340 1285 345 1395 345 1425 5false1816937M255 1345 C286 1346 345 1395 345 1425 5false1816938M345 1645 C345 1615 345 1525 345 1495 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false16939M255 1570 C288 1568 345 1525 345 1495 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false16940M705 1255 C705 1285 705 1395 705 1425 5false1816941M625 1345 C650 1345 705 1395 705 1425 5false1816942M705 1645 C705 1615 705 1525 705 1495 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false16943M625 1570 C652 1569 705 1525 705 1495 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false16944M1165 1245 C1165 1275 1165 1395 1165 1425 5false1816945M1080 1345 C1106 1345 1165 1395 1165 1425 5false1816946M1165 1645 C1165 1615 1165 1525 1165 1495 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false16947M1085 1570 C1110 1570 1165 1525 1165 1495 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false16948M1565 1245 C1565 1275 1570 1395 1570 1425 5false1816949M1485 1345 C1511 1346 1570 1395 1570 1425 5false1816950M1570 1645 C1570 1615 1570 1525 1570 1495 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false16951M1490 1570 C1516 1569 1570 1525 1570 1495 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false16952M1565 1245 C1565 1275 1962 1395 1962 1425 5false1816953M1961 1298 C1961 1328 1962 1395 1962 1425 5false1816954M2058 1340 C2025 1339 1962 1395 1962 1425 5false1816955M1962 1645 C1962 1615 1962 1525 1962 1495 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false16956M2063 1565 C2034 1565 1962 1525 1962 1495 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false16961M705 1845 C705 1875 705 1975 705 2005 5true1816962M610 1940 C641 1940 705 1975 705 2005 5false1816963M790 1939 C762 1939 705 1975 705 2005 5false1816964M761 1977 C784 1993 824 2020 848 2037 5true18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false16965M611 2145 C638 2144 705 2105 705 2075 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false16966M804 2139.5 C780 2139.5 705 2105 705 2075 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false16967M345 1845 C345 1875 345 1975 345 2005 5true1816968M245 1940 C273 1941 345 1975 345 2005 5false1816969M435 1939 C402 1940 345 1975 345 2005 5false1816970M345 2205 C345 2175 345 2105 345 2075 5true18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false16971M246 2145 C272 2143 345 2105 345 2075 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false16972M444 2139.5 C410 2138.5 345 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