113342PathwayMEP/DOXP PathwayThe DOXP/MEP pathway, also known as the non-mevalonate pathway, plays an essential role in creating the chemicals needed for many plants to function. This pathway, combined with the MEP/DOXP pathway give many plants their scents, such as cinnamon and ginger, and are responsible for the red colour in tomatoes. Terpenoids, also called isoprenoids, are a substantial yet varied class of organic chemicals that occur naturally. Plant terpenoids have aromatic qualities and are used for this and their role in traditional herbal remedies. The pathway begins with D-glyceraldehyde 3-phosphate, which is produced through glycolysis. Together with pyruvic acid and the enzyme 1-deoxy-D-xylulose 5-phosphate synthase 1, these are catalyzed into 1-deoxy-xylulose 5-phosphate. From there, 1-deoxy-xylulose 5-phosphate teams up with 1-deoxy-D-xylulose 5-phosphate reductoisomerase to create 2-c-methyl-D-erythritol 4-phosphate. Moving along in the chloroplast, after being produced through 2-c-methyl-D-erythritol 4-phosphate and the enzyme 2-c-methyl-D-erythritol 4-phosphate cytidyltransferase,4-cytidine 5'-diphospho)-2-C-methyl-D-erythritol is catalyzed by 4-diphosphocytidyl-2-c-methyl-D-erythritol kinase to create 2-phospho-4-(cytidine 5'-diphospho)-2-c-methyl-D-erythritol. After that, 2-c-methyl-D-erythritol 2,4-cyclodiphosphate synthase uses the newly produced 2-phospho-4-(cytidine 5'-diphospho)-2-c-methyl-D-erythritol to create 2-c-methyl-D-erythritol-2,4-cyclodiphosphate. This compound is then joined with 4-hydroxy-3-methylbut-2-en-1-yl diphosphate synthase to become 1-hydroxy-2-methyl-2-butenyl 4-diphosphate. This compound gets busy soon after its inception, branching off into two separate reactions: first reacting with 4-hydroxy-3-methylbut-2-enyl diphosphate reductase to create isopentenyl pyrophosphate, then reacting with the same enzyme to create dimethylallylpyrophosphate. Dimethylallylpyrophosphate is then looped into another reaction with isopentenyl-diphosphate delta-isomerase II, recreating isopentenyl pyrophosphate. It also reacts with geranylgeranyl pyrophosphate synthase 6, bringing the pathway into the mitochondrion to create geranyl pyrophosphate. This is later followed by a monoterpenoid biosynthesis pathway.MetabolicPW122502CenterPathwayVisualizationContext12277816982650#000099PathwayVisualization113205113342MEP/DOXP PathwayThe DOXP/MEP pathway, also known as the non-mevalonate pathway, plays an essential role in creating the chemicals needed for many plants to function. This pathway, combined with the MEP/DOXP pathway give many plants their scents, such as cinnamon and ginger, and are responsible for the red colour in tomatoes. Terpenoids, also called isoprenoids, are a substantial yet varied class of organic chemicals that occur naturally. Plant terpenoids have aromatic qualities and are used for this and their role in traditional herbal remedies. The pathway begins with D-glyceraldehyde 3-phosphate, which is produced through glycolysis. Together with pyruvic acid and the enzyme 1-deoxy-D-xylulose 5-phosphate synthase 1, these are catalyzed into 1-deoxy-xylulose 5-phosphate. From there, 1-deoxy-xylulose 5-phosphate teams up with 1-deoxy-D-xylulose 5-phosphate reductoisomerase to create 2-c-methyl-D-erythritol 4-phosphate. Moving along in the chloroplast, after being produced through 2-c-methyl-D-erythritol 4-phosphate and the enzyme 2-c-methyl-D-erythritol 4-phosphate cytidyltransferase,4-cytidine 5'-diphospho)-2-C-methyl-D-erythritol is catalyzed by 4-diphosphocytidyl-2-c-methyl-D-erythritol kinase to create 2-phospho-4-(cytidine 5'-diphospho)-2-c-methyl-D-erythritol. After that, 2-c-methyl-D-erythritol 2,4-cyclodiphosphate synthase uses the newly produced 2-phospho-4-(cytidine 5'-diphospho)-2-c-methyl-D-erythritol to create 2-c-methyl-D-erythritol-2,4-cyclodiphosphate. This compound is then joined with 4-hydroxy-3-methylbut-2-en-1-yl diphosphate synthase to become 1-hydroxy-2-methyl-2-butenyl 4-diphosphate. This compound gets busy soon after its inception, branching off into two separate reactions: first reacting with 4-hydroxy-3-methylbut-2-enyl diphosphate reductase to create isopentenyl pyrophosphate, then reacting with the same enzyme to create dimethylallylpyrophosphate. Dimethylallylpyrophosphate is then looped into another reaction with isopentenyl-diphosphate delta-isomerase II, recreating isopentenyl pyrophosphate. It also reacts with geranylgeranyl pyrophosphate synthase 6, bringing the pathway into the mitochondrion to create geranyl pyrophosphate. This is later followed by a monoterpenoid biosynthesis pathway.Metabolic4110199603SubPathway110200603SubPathway109806869Compound11020114875SubPathway109807993Compound22428017611833775Wanke M, Skorupinska-Tudek K, Swiezewska E: Isoprenoid biosynthesis via 1-deoxy-D-xylulose 5-phosphate/2-C-methyl-D-erythritol 4-phosphate (DOXP/MEP) pathway. Acta Biochim Pol. 2001;48(3):663-72.113342Pathway280177Hunter, W. (2007). The Non-mevalonate Pathway of Isoprenoid Precursor Biosynthesis. Journal Of Biological Chemistry, 282(30), 21573-21577. doi: 10.1074/jbc.r700005200113342Pathway1CellCL:00000006MyocyteCL:00001875HepatocyteCL:00001824Cardiomyocyte CL:00007463NeuronCL:00005407Epithelial CellCL:00000662Platelet CL:00002338Beta cellCL:00006391Homo sapiens9606EukaryoteHuman24Solanum lycopersicum4081EukaryoteTomato4Arabidopsis thaliana3702EukaryoteThale cress18Saccharomyces cerevisiae4932EukaryoteYeast12Mus musculus10090EukaryoteMouse5Bos taurus9913EukaryoteCattle17Rattus norvegicus10116EukaryoteRat10Drosophila melanogaster7227EukaryoteFruit fly6Caenorhabditis elegans6239EukaryoteRoundworm3Escherichia coli562Prokaryote2Bacteria2ProkaryoteBacteria21Xenopus laevis8355EukaryoteAfrican clawed frog60Nitzschia sp.0001EukaryoteNitzschia423Pseudomonas aeruginosa287Prokaryote25Escherichia coli (strain K12)83333Prokaryote49Bathymodiolus platifrons220390EukaryoteDeep sea mussel51Picea sitchensis3332EukaryoteSitka spruce19Schizosaccharomyces pombe4896Eukaryote5CytoplasmGO:00057371CytosolGO:000582935ChloroplastGO:00095073Mitochondrial MatrixGO:00057592MitochondrionGO:00057397Endoplasmic Reticulum MembraneGO:000578912Mitochondrial Inner MembraneGO:000574310Cell MembraneGO:000588613Endoplasmic ReticulumGO:000578315NucleusGO:000563414Mitochondrial Outer MembraneGO:000574111Extracellular SpaceGO:000561524Mitochondrial Intermembrane SpaceGO:000575831Periplasmic SpaceGO:00056204PeroxisomeGO:000577736MembraneGO:001602053Endoplasmic Reticulum BodyGO:001016834Plant-Type VacuoleGO:000032532Inner MembraneGO:007025827Peroxisome MembraneGO:000577819sarcoplasmic reticulumGO:001652926Golgi apparatus membraneGO:00001396LysosomeGO:000576416Lysosomal LumenGO:004320218Melanosome MembraneGO:003316225Golgi apparatusGO:000579420Endoplasmic Reticulum LumenGO:000578821SynapseGO:004520240PeriplasmGO:00425979MuscleBTO:0000887141181LiverBTO:000075972924BrainBTO:0000142891628StomachBTO:0001307155268Blood VesselBTO:000110274115cardiocyteBTO:000153925IntestineBTO:00006482Endothelium BTO:00003937Nervous SystemBTO:000148418PancreasBTO:00009884Adrenal MedullaBTO:000004971811HeartBTO:000056273108511PW_BS0000082111PW_BS0000021471241PW_BS000147151141PW_BS0001511601181PW_BS0001602253541PW_BS000024253541PW_BS0000241321121PW_BS0001321115121PW_BS000111122551PW_BS000122124151PW_BS0001241355171PW_BS0001351181171PW_BS0001182975101PW_BS0000242991101PW_BS000024205561PW_BS000024388161PW_BS0001124311PW_BS0000043211PW_BS000003509516PW_BS000050261115PW_BS000026103331PW_BS000103117131PW_BS0001171203171PW_BS0001201333121PW_BS000133951721PW_BS0000951553241PW_BS00015515612241PW_BS0001561613181PW_BS00016111PW_BS0000011783211PW_BS0001781771211PW_BS00017785241011PW_BS000085222341PW_BS00002422014PW_BS000024311511PW_BS0000312491341PW_BS000024181311PW_BS00001834695126PW_BS00002832711125PW_BS0000281122121PW_BS0001123683601PW_BS0000283671601PW_BS000028943PW_BS00009412112171PW_BS000121406351PW_BS000115407251PW_BS0001154239556PW_BS0001154241155PW_BS0001151192171PW_BS00011945895176PW_BS00011545911175PW_BS0001154793101PW_BS0001154812101PW_BS000115501361PW_BS000115206261PW_BS000024231511PW_BS000023101531PW_BS00010110813PW_BS000108188118PW_BS0000241951318PW_BS0000242137181PW_BS0000241644PW_BS0001642881441PW_BS000024221411PW_BS000022171211PW_BS000017315123PW_BS00002412815121PW_BS00012813412121PW_BS00013413013121PW_BS00013032914121PW_BS00002817018PW_BS0001703841251PW_BS0001001251351PW_BS0001253821451PW_BS0001002231241PW_BS0000243911261PW_BS0001123951361PW_BS0001133891461PW_BS00011213613171PW_BS00013639914171PW_BS0001134101551PW_BS00011544415171PW_BS00011548515101PW_BS00011515111PW_BS000015541315PW_BS00005449711PW_BS000049422411PW_BS000042101711PW_BS0000107028511PW_BS000070107313PW_BS000107100521PW_BS000100105113PW_BS0001051572241PW_BS00015715924PW_BS00015916611PW_BS00016615284PW_BS0001521873118PW_BS0000241632181PW_BS000163219314PW_BS00002421013181PW_BS00002421217181PW_BS000024226441PW_BS00002416212181PW_BS000162224241PW_BS0000242811251PW_BS0000242851041PW_BS0000242863641PW_BS0000242875341PW_BS0000242273441PW_BS0000242941141PW_BS0000243081011PW_BS0000243183123PW_BS0000243221231PW_BS0000243125231PW_BS0000243201123PW_BS00002429341PW_BS0000243317121PW_BS0000281141112PW_BS00011434713125PW_BS00002834524121PW_BS000028310312PW_BS00002430412PW_BS000024383751PW_BS000100390761PW_BS0001123987171PW_BS0001133361121PW_BS000028109323PW_BS000109409115PW_BS0001154251355PW_BS0001154182451PW_BS0001151371117PW_BS00013746013175PW_BS00011545424171PW_BS0001154831110PW_BS0001154957101PW_BS00011548924101PW_BS00011548012101PW_BS00011530013101PW_BS000024208116PW_BS0000245062461PW_BS0001153211515PW_BS000032592711PW_BS00005929111PW_BS00002914101PW_BS000014892PW_BS0000891041431PW_BS00010419914181PW_BS0000241985181PW_BS0000242905491PW_BS00002430635511PW_BS00002433527121PW_BS000028372102PW_BS000028429151PW_BS0001154222751PW_BS0001154641171PW_BS00011537527171PW_BS00005348414101PW_BS00011549127101PW_BS0001155082761PW_BS0001155411PW_BS0000053551914PW_BS0000352111018PW_BS00002433217121PW_BS0000281151012PW_BS000115405105PW_BS0001151231751PW_BS0001233761017PW_BS00005344717171PW_BS0001153344121PW_BS000028408451PW_BS0001153744171PW_BS0000534824101PW_BS000115502461PW_BS00011513121PW_BS0000135811411PW_BS00005827151PW_BS000027471914PW_BS00004746114PW_BS00004672513PW_BS000072612517PW_BS000061918511PW_BS000091711PW_BS000007971521PW_BS00009712915121PW_BS00012914315191PW_BS0001431465191PW_BS0001462164181PW_BS0000242171518PW_BS00002421815181PW_BS0000242771218PW_BS00002431323PW_BS0000243331212PW_BS000028350114121PW_BS0000283511512PW_BS00002835325127PW_BS000028412125PW_BS00011543311451PW_BS000115435155PW_BS0001154461217PW_BS000115468114171PW_BS00011547225177PW_BS0001154701517PW_BS0001154781010PW_BS0001154991510PW_BS0001155161561PW_BS000115209106PW_BS000024517156PW_BS00011516212PW_BS000016397113PW_BS0000396618518PW_BS0000665181PW_BS0000511901118PW_BS000024184121PW_BS000024562611PW_BS0000569611PW_BS0000092811611PW_BS000028126651PW_BS00012612711651PW_BS0001273016101PW_BS000024302116101PW_BS0000241136121PW_BS000113337116121PW_BS0000284436171PW_BS000115448116171PW_BS000115204111PW_BS000020331811PW_BS000033432511PW_BS0000432441011PW_BS00002460251PW_BS0000603612011PW_BS0000363772113PW_BS00003793252011PW_BS000093110231PW_BS0001106131PW_BS000006140103PW_BS0001401802211PW_BS000180207661PW_BS00002421425181PW_BS0000242156181PW_BS00002465111PW_BS0000652916491PW_BS0000242924491PW_BS00002429817101PW_BS00002434141121PW_BS00002834318121PW_BS0000283522512PW_BS00002835625121PW_BS000028360410121PW_BS0000283702601PW_BS000028228361PW_BS000024232403PW_BS0000244151851PW_BS0001154141551PW_BS0001154192551PW_BS00011543441051PW_BS000115436255PW_BS00011545118171PW_BS00011545015171PW_BS00011545525171PW_BS000115469410171PW_BS0001154712517PW_BS00011548718101PW_BS00011549025101PW_BS0001155041861PW_BS0001155072561PW_BS00011551541061PW_BS0001155131761PW_BS000115869D-Glyceraldehyde 3-phosphateHMDB0001112Glyceraldehyde 3-phosphate (G3P) or triose phosphate is an aldotriose, an important metabolic intermediate in both glycolysis and gluconeogenesis, and in tryptophan biosynthesis. G3P is formed from Fructose-1,6-bisphosphate, Dihydroxyacetone phosphate (DHAP),and 1,3-bisphosphoglycerate, (1,3BPG), and this is how glycerol (as DHAP) enters the glycolytic and gluconeogenesis pathways.591-59-3C0066172917138GAP709DB02263OC(COP(O)(O)=O)C=OC3H7O6PInChI=1S/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h1,3,5H,2H2,(H2,6,7,8)LXJXRIRHZLFYRP-UHFFFAOYSA-N(2-hydroxy-3-oxopropoxy)phosphonic acid170.0578169.998024468-0.923glyceraldehyde 3 phosphate0-2FDB0016192-hydroxy-3-(phosphonooxy)-propanal;3-phosphoglyceraldehyde;D-glyceraldehyde 3-phosphate;D-glyceraldehyde-3-p;Dl-glyceraldehyde 3-phosphate;Gap;Glyceraldehyde-3-p;Glyceraldehyde-3-phosphate;Glyceraldehyde-p;Glyceraldehyde-phosphate;2-hydroxy-3-(phosphonooxy)propanal;Gliceraldehido-3-fosfato;Glyceraldehyde 3-(dihydrogen phosphate);Glycerinaldehyd-3-phosphat;Glyzerinaldehyd-3-phosphat;(2-hydroxy-3-oxopropyl) dihydrogen phosphoric acid;Glyceraldehyde 3-(dihydrogen phosphoric acid);Glyceraldehyde-3-phosphoric acidPW_C000869Glyc3P102781781259071475935151688316012800225770142537709713277935111120734122121183124123334135123754118125784297125949299127239205127409388164Pyruvic acidHMDB0000243Pyruvic acid is an intermediate compound in the metabolism of carbohydrates, proteins, and fats. In thiamine deficiency, its oxidation is retarded and it accumulates in the tissues, especially in nervous structures. (From Stedman, 26th ed.) Biological Source: Intermediate in primary metabolism including fermentation processes. Present in muscle in redox equilibrium with Lactic acid. A common constituent, as a chiral cyclic acetal linked to saccharide residues, of bacterial polysaccharides. Isolated from cane sugar fermentation broth and peppermint. Constituent of Bauhinia purpurea, Cicer arietinum (chickpea), Delonix regia, Pisum sativum (pea) and Trigonella caerulea (sweet trefoil) Use/Importance: Reagent for regeneration of carbonyl compdounds from semicarbazones, phenylhydrazones and oximes. Flavoring ingredient (Dictionary of Organic Compounds).127-17-3C00022106032816PYRUVATE1031DB00119CC(=O)C(O)=OC3H4O3InChI=1S/C3H4O3/c1-2(4)3(5)6/h1H3,(H,5,6)LCTONWCANYUPML-UHFFFAOYSA-N2-oxopropanoic acid88.062188.0160439940.181pyruvic acid0-1FDB0082932-oxopropanoate;2-oxopropanoic acid;2-oxopropionate;2-oxopropionic acid;Acetylformate;Acetylformic acid;Bts;Pyroracemate;Pyroracemic acid;Pyruvate;A-ketopropionate;A-ketopropionic acid;Alpha-ketopropionate;Alpha-ketopropionic acid;2-ketopropionic acid;2-oxopropansaeure;2-oxopropionsaeure;Acide pyruvique;Alpha-oxopropionsaeure;Brenztraubensaeure;Ch3cocooh;2-ketopropionate;α-ketopropionate;α-ketopropionic acid;A-oxopropionsaeure;α-oxopropionsaeurePW_C000164Pyr1722044228118131449501457265365103540511754401185444120556613255701335893955920147595115160221556067156607416161261606383164671786510177653285745722274952208200225126223115292249153491877310111779723467797832778090112800043688004236780695135112879941156831211199504061200111241201751221208784071211484231211544241234541191237204581237264591253404791253902991255342971258544811268835011269313881270672051278582069441-Deoxy-D-xylulose 5-phosphateHMDB00012131-Deoxy-D-xylulose 5-phosphate belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups. 1-Deoxy-D-xylulose 5-phosphate is soluble (in water) and a moderately acidic compound (based on its pKa). Within the cell, 1-deoxy-D-xylulose 5-phosphate is primarily located in the cytoplasm. 1-Deoxy-D-xylulose 5-phosphate exists in all living organisms, ranging from bacteria to humans. 1-Deoxy-D-xylulose 5-phosphate participates in a number of enzymatic reactions. In particular, 1-Deoxy-D-xylulose 5-phosphate can be biosynthesized from D-glyceraldehyde 3-phosphate through its interaction with the enzyme 1-deoxyxylulose-5-phosphate synthase. Furthermore, 1-Deoxy-D-xylulose 5-phosphate can be converted into 2-C-methyl-D-erythritol 4-phosphate through the action of the enzyme 1-deoxy-D-xylulose 5-phosphate reductoisomerase. Furthermore, 1-Deoxy-D-xylulose 5-phosphate can be biosynthesized from D-glyceraldehyde 3-phosphate; which is mediated by the enzyme 1-deoxyxylulose-5-phosphate synthase. Furthermore, 1-Deoxy-D-xylulose 5-phosphate can be converted into 2-C-methyl-D-erythritol 4-phosphate through its interaction with the enzyme 1-deoxy-D-xylulose 5-phosphate reductoisomerase. Furthermore, 1-Deoxy-D-xylulose 5-phosphate and 2-amino-3-phosphonopropionic acid can be converted into pyridoxine 5'-phosphate through its interaction with the enzyme pyridoxine 5'-phosphate synthase. Finally, 1-Deoxy-D-xylulose 5-phosphate can be biosynthesized from D-glyceraldehyde 3-phosphate and pyruvic acid through the action of the enzyme 1-deoxyxylulose-5-phosphate synthase. Outside of the human body, 1-deoxy-D-xylulose 5-phosphate can be found in a number of food items such as rowanberry, scarlet bean, hickory nut, and other soy product. This makes 1-deoxy-D-xylulose 5-phosphate a potential biomarker for the consumption of these food products. 1-Deoxy-D-xylulose 5-phosphate is a substrate for 2,4-dienoyl-CoA reductase (mitochondrial).190079-18-6C1143744320116493DEOXYXYLULOSE-5P391473DB02496CC(=O)[C@@H](O)[C@H](O)COP(O)(O)=OC5H11O7PInChI=1S/C5H11O7P/c1-3(6)5(8)4(7)2-12-13(9,10)11/h4-5,7-8H,2H2,1H3,(H2,9,10,11)/t4-,5-/m1/s1AJPADPZSRRUGHI-RFZPGFLSSA-N{[(2R,3S)-2,3-dihydroxy-4-oxopentyl]oxy}phosphonic acid214.1104214.024239218-0.8941-deoxy-D-xylulose-5-phosphate0-2FDB0224941-deoxy-d-threo-pentulose 5-phosphate;1-deoxy-d-xylulose 5-phosphate;D-1-deoxyxylulose-5-p;Doxp;Dxp;Deoxyxylulose-5-phosphatePW_C000944DDXP426092-C-methyl-D-erythritol 4-phosphate2-c-Methyl-D-erythritol-4-phosphate belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain. 2-c-Methyl-D-erythritol-4-phosphate is soluble (in water) and a moderately acidic compound (based on its pKa). Outside of the human body, 2-c-methyl-D-erythritol-4-phosphate can be found in a number of food items such as cowpea, capers, shallot, and horseradish tree. This makes 2-c-methyl-D-erythritol-4-phosphate a potential biomarker for the consumption of these food products.[H][C@@](O)(COP(O)(O)=O)[C@@](C)(O)COC5H13O7PInChI=1S/C5H13O7P/c1-5(8,3-6)4(7)2-12-13(9,10)11/h4,6-8H,2-3H2,1H3,(H2,9,10,11)/t4-,5+/m1/s1XMWHRVNVKDKBRG-UHNVWZDZSA-N[(2R,3S)-2,3,4-trihydroxy-3-methylbutoxy]phosphonic acid216.1263216.039889282-0.845(2R,3S)-2,3,4-trihydroxy-3-methylbutoxyphosphonic acid0-2PW_C0426092CmDe4p57Cytidine triphosphateHMDB0000082Cytidine 5'-(tetrahydrogen triphosphate) or CTP is a cytosine nucleotide containing three phosphate groups esterified to a ribose moiety at the 5' position. CTP is integral to the synthesis or mRNA, rRNA and tRNA through RNA polymerases. Cytidine triphosphate (CTP) is also critical to the synthesis of phosphatidylcholine via the enzyme CTP: phosphocholine cytidyltransferase. This reaction is the rate-limiting step in the synthesis of phosphatidylcholine.65-47-4C00063617617677CTP5941DB02431NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1OC9H16N3O14P3InChI=1S/C9H16N3O14P3/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(24-8)3-23-28(19,20)26-29(21,22)25-27(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H,21,22)(H2,10,11,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1PCDQPRRSZKQHHS-XVFCMESISA-N({[({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid483.1563482.984511771-1.647CTP0-3FDB0128335'-(tetrahydrogen triphosphate) cytidine;5'-ctp;Ctp;Cytidine 3'-triphosphate;Cytidine 5'-(tetrahydrogen triphosphate);Cytidine 5'-triphosphate;Cytidine 5'-triphosphoric acid;Cytidine 5-prime-triphosphate;Cytidine triphosphate;Cytidine mono;Cytidine mono(tetrahydrogen triphosphate) (ester);Cytidine-5'-triphosphate;Deoxycytosine triphosphate;H4ctpPW_C000057CTP4272311508271825766101580010870771887593160913719591422131219416412510288152851511531724915342221537418347591742650315773151287844811178733132799491347995713079964329804161709478438494812125948173829867722311063339111326839511327338911552513611553039912032841012085412212134012112221212412298344412343413512476411812565448512584029712637429912729220512793538840034Hydrogen 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+215467087531578831848311162146326146454223149278017425022425442454710457618469470524110353271115353112562610856391075699100572010557421175963147603715560701576093161613015962321666483178660115266921016843188691018771001637168205719120674532197454220747222275252137532210755821275721607590170819522582181518243226841316284202249139195915524911915164120152811218128512246286122662871252122713257223133252941533030842329315423543184240132242405312424543207691229377136133772101347737233177804114779551327799032777991347783793457992913080019368803873108038830480722119938231249482338311055038811285594113280390115537398115539118115856336116205109119973406120193407120549122120593409121170424121171425122569418122615384122687125122758120123183135123218137123742459123743460125141454125188121125273136125359479125550481125730483125736297125809299126517495126717489126766480126823300126902501127213208128308506128361391128430395429374-(cytidine 5'-diphospho)-2-C-methyl-D-erythritolCDP-ME, also known as 4-dpcme, belongs to the class of organic compounds known as pyrimidine ribonucleoside diphosphates. These are pyrimidine ribonucleotides with diphosphate group linked to the ribose moiety. CDP-ME is soluble (in water) and a moderately acidic compound (based on its pKa).57823[H][C@@](O)(COP(O)(=O)OP([O-])(=O)OC[C@@]1([H])O[C@@]([H])(N2C=CC(=N)N=C2[O-])[C@]([H])(O)[C@]1([H])O)[C@@](C)(O)COC14H23N3O14P2InChI=1S/C14H25N3O14P2/c1-14(23,6-18)8(19)5-29-33(26,27)31-32(24,25)28-4-7-10(20)11(21)12(30-7)17-3-2-9(15)16-13(17)22/h2-3,7-8,10-12,18-21,23H,4-6H2,1H3,(H,24,25)(H,26,27)(H2,15,16,22)/p-2/t7-,8-,10-,11-,12-,14+/m1/s1YFAUKWZNPVBCFF-XHIBXCGHSA-L1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[({hydroxy[(2R,3S)-2,3,4-trihydroxy-3-methylbutoxy]phosphoryl phosphonato}oxy)methyl]oxolan-2-yl]-4-imino-1,4-dihydropyrimidin-2-olate519.294519.066623588-1.3471-[(2R,3R,4S,5R)-3,4-dihydroxy-5-({[hydroxy(2R,3S)-2,3,4-trihydroxy-3-methylbutoxyphosphoryl phosphonato]oxy}methyl)oxolan-2-yl]-4-iminopyrimidin-2-olate-2-2Cdp-me, cdp-methyl-d-erythritol, 4-diphosphocytidyl-2c-methyl-d-erythritol, 4-diphosphocytidyl-2-c-methylerythritolPW_C0429374C5D2CM170PyrophosphateHMDB0000250The anion, the salts, and the esters of pyrophosphoric acid are called pyrophosphates. The pyrophosphate anion is abbreviated PPi and is formed by the hydrolysis of ATP into AMP in cells. This hydrolysis is called pyrophosphorolysis. The pyrophosphate anion has the structure P2O74-, and is an acid anhydride of phosphate. It is unstable in aqueous solution and rapidly hydrolyzes into inorganic phosphate. Pyrophosphate is an osteotoxin (arrests bone development) and an arthritogen (promotes arthritis). It is also a metabotoxin (an endogenously produced metabolite that causes adverse health affects at chronically high levels). Chronically high levels of pyrophosphate are associated with hypophosphatasia. Hypophosphatasia (also called deficiency of alkaline phosphatase or phosphoethanolaminuria) is a rare, and sometimes fatal, metabolic bone disease. Hypophosphatasia is associated with a molecular defect in the gene encoding tissue non-specific alkaline phosphatase (TNSALP). TNSALP is an enzyme that is tethered to the outer surface of osteoblasts and chondrocytes. TNSALP hydrolyzes several substances, including inorganic pyrophosphate (PPi) and pyridoxal 5'-phosphate (PLP), a major form of vitamin B6. When TSNALP is low, inorganic pyrophosphate (PPi) accumulates outside of cells and inhibits the formation of hydroxyapatite, one of the main components of bone, causing rickets in infants and children and osteomalacia (soft bones) in adults. Vitamin B6 must be dephosphorylated by TNSALP before it can cross the cell membrane. Vitamin B6 deficiency in the brain impairs synthesis of neurotransmitters which can cause seizures. In some cases, a build-up of calcium pyrophosphate dihydrate crystals in the joints can cause pseudogout.14000-31-8C0001364410218361PPI559142DB04160[O-]P([O-])(=O)OP([O-])([O-])=OO7P2InChI=1S/H4O7P2/c1-8(2,3)7-9(4,5)6/h(H2,1,2,3)(H2,4,5,6)/p-4XPPKVPWEQAFLFU-UHFFFAOYSA-J(phosphonooxy)phosphonic acid173.9433173.9119253784pyrophosphoric acid0-3FDB021918(4-)diphosphoric acid ion;(p2o74-)diphosphate;Diphosphate;Diphosphoric acid;Ppi;Pyrometaphosphate;Pyrophosphate;Pyrophosphate tetraanion;Pyrophosphate(4-) ion;[o3popo3](4-);Diphosphat;P2o7(4-);Pyrophosphat;Pyrophosphate ion;Phosphonato phosphoric acid;Pyrophosphoric acid;Pyrophosphoric acid ionPW_C000170Ppi122354638429237353288222121731620492410592815294175144868545034895252104529410154091175424103543311854581205548111555913255841335606135565510858791076239166697819970731887134163727216073121987318213827515182832101186916112002222120411641231522512323249125122881257922612695290152193061537518347601742561315426973187723532977317128776353367841633578928331791531127995013479958130800473728041717085630194786384948141259481938298678223110634391113270395113275389115527136115532399119934122120017124120032406120330410120936407121261429121341121121486383122407422122985444123502119123831464124044398124977375125324297125395299125410479125597484125656485125876481126552491126869205126935388126950501127337206128124508146NADPHHMDB0000221Nicotinamide 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_C000146NADPH18581903778107965821188372160929161549468731479314479714531011157891085972147612815962713567791177068188710316371542057205160731521373452107559212759117081942258219151842122411812198118932111200622212150164122452861259622612648249423433154374632276911293771661327738533177394332774601307750411277511115776233368071211911316494120105407120425405120452122120616123121141125121275429121402124121483383123059376123086135123241447123712136123846464123961118124041398125472481125696297126214299126529495127009206127572388128101390143NADPHMDB0000217Nicotinamide 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_C000143NADP18381913768578010824188392161129161749468531479614480114530811157901086017147613215962733567781177069188710516371522057206160731721373462107562212758917081972258220151841922411811198118972111200822212152164122492861259722612650249423443154374532276913293771641327738433177396332774611307751511577624336778143347787011280713119113165941201064071204294051204501221206044081206181231211421251212774291214011241214853831230633761230841351232293741232434471237131361238484641239601181240433981254734811256942971257434821262152991265284951270102061272255021275703881281003901034Adenosine 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_C001034ADP234134841522482138015963159783106114151821901492104182113102161582408592435272728472736462855293165723635614400234476314770915036265157752089752171005315111534911253921035446120554412955721335624108574111757641015849143585614658781075899147592615160501556111161623116664951786700946841188687216071592057187206720821072262137231211730019873032167391217741021874331637483222818722511851277119051701201328112180285132622231532930842328315423983134262232242696318770292537708713277216134773063297747233377663336780393327804335078170128782153517824435378414335784951157870533178849130789203348003036880622118806511358067611994827124113283388116204109119944122119994406120156407120318382120366412121248429121394123121399433121472408121899383121976410122064125122085405122405422122445435122973399123013446123818464123953447123958468124030374124452398124529444124615136124636376124947472124975375125012470125334297125373479125492299125517481125645484126125485126219300126235495126242478126550491126597499126915501127733516127780395127797390127803209128122508128168517128313389429382-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritolCDP-ME-2P belongs to the class of organic compounds known as pyrimidine ribonucleoside diphosphates. These are pyrimidine ribonucleotides with diphosphate group linked to the ribose moiety. CDP-ME-2P is soluble (in water) and a moderately acidic compound (based on its pKa).57919[H][C@@](O)(COP(O)(=O)OP([O-])(=O)OC[C@@]1([H])O[C@@]([H])(N2C=CC(=N)N=C2[O-])[C@]([H])(O)[C@]1([H])O)[C@](C)(CO)OP([O-])([O-])=OC14H22N3O17P3InChI=1S/C14H26N3O17P3/c1-14(6-18,33-35(23,24)25)8(19)5-31-37(28,29)34-36(26,27)30-4-7-10(20)11(21)12(32-7)17-3-2-9(15)16-13(17)22/h2-3,7-8,10-12,18-21H,4-6H2,1H3,(H,26,27)(H,28,29)(H2,15,16,22)(H2,23,24,25)/p-4/t7-,8-,10-,11-,12-,14+/m1/s1HTJXTKBIUVFUAR-XHIBXCGHSA-J1-[(2R,3R,4S,5R)-5-[({[(2R,3S)-2,4-dihydroxy-3-methyl-3-(phosphonatooxy)butoxy](hydroxy)phosphoryl phosphonato}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-4-imino-1,4-dihydropyrimidin-2-olate597.257597.018401574-1.2761-[(2R,3R,4S,5R)-5-({[(2R,3S)-2,4-dihydroxy-3-methyl-3-(phosphonatooxy)butoxy(hydroxy)phosphoryl phosphonato]oxy}methyl)-3,4-dihydroxyoxolan-2-yl]-4-iminopyrimidin-2-olate-4-5Cdp-me-2p, cdp-methyl-d-erylthritol 2-phosphate, 4-diphosphocytidyl-2c-methyl-d-erythritol 2-phosphate, 4-diphosphocytidyl-2-c-methylerythritol 2-phosphatePW_C042938pcdCmDe414Adenosine 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_C000414ATP9221460826616414224781373332799593439976321051821121021464921561421605824055924342727264628122930296631637236166136175143992344743147689148645450328950352651557520597521510052501045291101531311153461125390103540611754301185443120554212955561325569133560313556211085846143585414658761075897147592415160481556109161623016664931786839188687016069761997157205718420672092107225213722921172981987302216739021774082187432163748122274991908186225118472771190317012010281120391641217828512578226126912901326422315327308423263154262132242694318770282537721813477233329774683337763233678037332780413507816812878214351782403537841133578494115788501307886533178919334800283688004618480674119856291948261241132349411328238811628010911991412211999240612015440712024538212036241212124642912139212312139743312147140812197441012206512512207938312208340512240242212244443512291939912300944612381646412395144712395646812402937412452744412461613612463039812463437612494347212497237512501147012530429712537147912539229912551548112559548412612348512622030012623449512624047812654749112659649912691350112712338912773151612778139512779639012780120912811950812816751764Cytidine monophosphateHMDB0000095Cytidine monophosphate, also known as 5'-cytidylic acid and abbreviated CMP, is a nucleotide. It is an ester of phosphoric acid with the nucleoside cytidine. CMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase cytosine. Cytidine monophosphate (CMP) is derived from cytidine triphosphate (CTP) with subsequent loss of two phosphates. The synthesis of the pyrimidines CTP and UTP occurs in the cytoplasm and starts with the formation of carbamoyl phosphate from glutamine and CO2. Next, aspartate undergoes a condensation reaction with carbamoyl-phosphate to form orotic acid. In a subsequent cyclization reaction, the enzyme Aspartate carbamoyltransferase forms N-carbamoyl-aspartate which is converted into dihydroorotic acid by Dihydroorotase. The latter is converted to orotate by Dihydroorotate oxidase. Orotate is covalently linked with a phosphorylated ribosyl unit with Orotate phosphoribosyltransferase (aka "PRPP transferase") catalyzing reaction, yielding orotidine monophosphate (OMP). Orotidine-5-phosphate is decarboxylated by Orotidine-5'-phosphate decarboxylase to form uridine monophosphate (UMP). UMP is phosphorylated by two kinases to uridine triphosphate (UTP) via two sequential reactions with ATP. CTP is subsequently formed by amination of UTP by the catalytic activity of CTP synthetase. Cytosine monophosphate (CMP) and uridine monophosphate (UMP) have been prescribed for the treatment of neuromuscular affections in humans. Patients treated with CMP/UMP recover from altered neurological functions. Additionally, the administration of CMP/UMP appears to favour the entry of glucose in the muscle and CMP/UMP may be important in maintaining the level of hepatic glycogen constant during exercise. [PMID:18663991].63-37-6C00055613117361CMP5901NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1OC9H14N3O8PInChI=1S/C9H14N3O8P/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H2,10,11,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1IERHLVCPSMICTF-XVFCMESISA-N{[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid323.1965323.051850951-1.305cytidine monophosphate0-2FDB0118825'-cmp;5-cytidylate;5-cytidylic acid;Cmp;Cytidine 5'-monophosphate;Cytidine 5'-monophosphorate;Cytidine 5'-monophosphoric acid;Cytidine 5'-phosphate;Cytidine 5'-phosphorate;Cytidine 5'-phosphoric acid;Cytidine mono(dihydrogen phosphate);Cytidine monophosphate;Cytidylate;Cytidylic acid;Cytidine-5'-monophosphate;Pc;Cytidine-5'-monophosphoric acidPW_C000064CMP115182512142734233861849725657681015802108707918875951609147249915122492571951219616412210151152742851533630815373493481517426523157844911178488115785731307873613279953134799693318042117094791384948213839868022311063739111327739011553539812085512212134612112221612412248740512260512512343513512476811812505337612517713612584129712637829912664147812675230012729320512794038812821720912834639542939 2-C-Methyl-D-erythritol-2,4-cyclodiphosphate2-c-Methyl-D-erythritol-2,4-cyclodiphosphate, also known as me-2,4cpp, belongs to the class of organic compounds known as organic pyrophosphates. These are organic compounds containing the pyrophosphate oxoanion, with the structure OP([O-])(=O)OP(O)([O-])=O. 2-c-Methyl-D-erythritol-2,4-cyclodiphosphate is soluble (in water) and a moderately acidic compound (based on its pKa). 2-c-Methyl-D-erythritol-2,4-cyclodiphosphate may be a unique E.coli metabolite.58483[H][C@@]1(O)COP([O-])(=O)OP([O-])(=O)O[C@@]1(C)COC5H10O9P2InChI=1S/C5H12O9P2/c1-5(3-6)4(7)2-12-15(8,9)14-16(10,11)13-5/h4,6-7H,2-3H2,1H3,(H,8,9)(H,10,11)/p-2/t4-,5+/m1/s1SFRQRNJMIIUYDI-UHNVWZDZSA-L(6S,7R)-7-hydroxy-6-(hydroxymethyl)-6-methyl-2,4-dioxo-1,3,5,2λ⁵,4λ⁵-trioxadiphosphocane-2,4-bis(olate)276.075275.980004942-0.762(6S,7R)-7-hydroxy-6-(hydroxymethyl)-6-methyl-2,4-dioxo-1,3,5,2λ⁵,4λ⁵-trioxadiphosphocane-2,4-bis(olate)-2-2Me-2,4cpp;2-c-methyl-d-erythritol 2,4-cyclodiphosphate;2-c-methyl-d-erythritol-2,4-cyclodiphosphatePW_C042939ME24CPP65991521261616480145293411521-Hydroxy-2-methyl-2-butenyl 4-diphosphate1-Hydroxy-2-methyl-2-butenyl 4-diphosphate has the chemical formula C6H14O7P2, and an average molecular weight of 260.119. 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate is involved in the MEP/DOXP Pathway.78615664C\C(CO)=C/COP(O)(=O)CP(O)(O)=OC6H14O7P2InChI=1S/C6H14O7P2/c1-6(4-7)2-3-13-15(11,12)5-14(8,9)10/h2,7H,3-5H2,1H3,(H,11,12)(H2,8,9,10)/b6-2+MWPLXVJYALXWPR-QHHAFSJGSA-N{[hydroxy({[(2E)-4-hydroxy-3-methylbut-2-en-1-yl]oxy})phosphoryl]methyl}phosphonic acid260.119260.021476787-1.314{hydroxy[(2E)-4-hydroxy-3-methylbut-2-en-1-yl]oxyphosphoryl}methylphosphonic acid0-2(<i>e</i>)-4-hydroxy-3-methylbut 2-en-1-yl diphosphate;(<i>e</i>)-4-hydroxy-3-methylbut-2-en-1-yl diphosphate;(e)-4-hydroxy-3-methylbut 2-en-1-yl diphosphate;(e)-4-hydroxy-3-methylbut-2-en-1-yl diphosphate;Hmbdp;HmebuppPW_C0411521H2M2B4405582Fe-2SHMDB0061344Bis(λ²-iron(2+) ion) disulfane tetrasulfanide belongs to the class of inorganic compounds known as transition metal sulfides. These are inorganic compounds containing a sulfur atom of an oxidation state of -2, in which the heaviest atom bonded to the oxygen is a transition metal.S[Fe]1(S)S[Fe](S)(S)S1Fe2H4S6InChI=1S/2Fe.4H2S.2S/h;;4*1H2;;/q2*+2;;;;;;/p-4TUVRTRPESCSNGS-UHFFFAOYSA-Jbis(lambda2-iron(2+) ion) disulfane tetrasulfanide308.112307.7336085340bis(lambda2-iron(2+) ion) disulfane tetrasulfanide02PW_C0405582Fe2S374224012842571743893462654754314829948372850564549712655121277046160130303011304230277715113777273377837713478386132792071121178111331215864071217951241225673841226644061231524431231674481241441191243461181251401211252391201261892991267154801267964791276803881283063911283945011420WaterHMDB0002111Water 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_C001420H2O558949109513941513162144811352615624286521069120770338231883821094311377491465541590432018242532222678602727462778172805293143703164723634614598364727374941935030275156751959752141005227945236103529710553191115343113535511254021105470123548312554921265507127553413055371145541129559113556081185622108569165759140577810158411435853146587710758909559101475940151603215560591576087161612316361331596215162181666477178650718066001526713117684018868881607162205718120771932067211211722821372382147243215729519873502167388210740121274672227492224750019075881708201225823722684141629265261185027711922164120112811221328512250286122642871232724912520227126326512693290127052911271529213007298130193001302530113037302132612231332729415340308423273154269531843691322769142937701925377102132771311337721513477378331773973327747133377516115775363347762833677722337777593417781634377982347780713297823535278242353782703567911336080014368800393708059122880656119938303839479438411055739011063939111584439811987923211991512211996340612000840712004640812011312412036541212043040512043840912060641512079441412115842512124042912135112112138141912160743412211838212238443612275312012279737412280444312301244612306437612307213712313144712314213612316244812323145112338445012373046012381046412394045512416546912467039912493847112494547212530529712535347912538648112542448212548029912568248312570747812574548712605449012623849512627348412676448012689650112696350212701738812717720812719920912722750412750650712757651512783638912808239512817651341102Reduced ferredoxinReduced ferredoxin is involved in the MEP/DOXP Pathway.C0013817513PW_C041102RedFed1039Isopentenyl pyrophosphateHMDB0001347Isopentenyl pyrophosphate, IPP or isopentenyl diphosphate, is an intermediate in the HMG-CoA reductase pathway used by organisms in the biosynthesis of terpenes and terpenoids. IPP is formed from Mevalonate-5-pyrophosphate, in a reaction catalyzed by the enzyme mevalonate-5-pyrophosphate decarboxylase. (wikipedia).358-71-4C001291195165841158DB04714CC(=C)CCOP(O)(=O)OP(O)(O)=OC5H12O7P2InChI=1S/C5H12O7P2/c1-5(2)3-4-11-14(9,10)12-13(6,7)8/h1,3-4H2,2H3,(H,9,10)(H2,6,7,8)NUHSROFQTUXZQQ-UHFFFAOYSA-N({hydroxy[(3-methylbut-3-en-1-yl)oxy]phosphoryl}oxy)phosphonic acid246.0921246.005825762-1.573isopentenyl-diphosphate0-2FDB0225693-methyl-3-butenyl pyrophosphate;Delta3-isopentenyl diphosphate;Delta3-methyl-3-butenyl diphosphate;Diphosphoric acid mono(3-methyl-3-butenyl) ester;Ipp;Ipr;Isopentenyl diphosphate;Isopentenyl pyrophosphate;Isopentenyl-pp;Mono(3-methyl-3-butenyl) diphosphate;Delta(3)-isopentenyl-pp;Delta-3-isopentenyl pyrophosphat;3-methylbut-3-en-1-yl trihydrogen diphosphate;3-methylbut-3-enyl phosphono hydrogen phosphate;Delta-3-isopentenyl pyrophosphate;Ippp;3-methyl-3-butenyl pyrophosphoric acid;Isopentenyl diphosphoric acid;3-methylbut-3-en-1-yl trihydrogen diphosphoric acid;3-methylbut-3-enyl phosphono hydrogen phosphoric acid;Delta-3-isopentenyl pyrophosphoric acid;δ-3-isopentenyl pyrophosphate;δ-3-isopentenyl pyrophosphoric acid;Delta3-isopentenyl diphosphoric acid;δ3-isopentenyl diphosphate;δ3-isopentenyl diphosphoric acid;Delta3-methyl-3-butenyl diphosphoric acid;δ3-methyl-3-butenyl diphosphate;δ3-methyl-3-butenyl diphosphoric acid;Diphosphate mono(3-methyl-3-butenyl) ester;Isopentenyl pyrophosphoric acid;Mono(3-methyl-3-butenyl) diphosphoric acidPW_C001039IsopPyr805583021549873071987606160828121012310225123522497892311112147512212403313541101Oxidized ferredoxinOxidized ferredoxin is involved in the MEP/DOXP Pathway.C0013917908PW_C041101OxidFer874DimethylallylpyrophosphateHMDB0001120Dimethylallylpyrophosphate, also known as 2-isopentenyl diphosphate or delta-prenyl diphosphate, belongs to the class of organic compounds known as isoprenoid phosphates. These are prenol lipids containing a phosphate group linked to an isoprene (2-methylbuta-1,3-diene) unit. Dimethylallylpyrophosphate exists as a solid, slightly soluble (in water), and a moderately acidic compound (based on its pKa). Dimethylallylpyrophosphate has been found in human muscle tissue. Within the cell, dimethylallylpyrophosphate is primarily located in the peroxisome, cytoplasm and mitochondria. Dimethylallylpyrophosphate exists in all living organisms, ranging from bacteria to humans. In humans, dimethylallylpyrophosphate is involved in the lovastatin action pathway, the desmosterolosis pathway, the risedronate action pathway, and the ibandronate action pathway. Dimethylallylpyrophosphate is also involved in several metabolic disorders, some of which include the wolman disease pathway, the chondrodysplasia punctata II, X linked dominant (CDPX2) pathway, the mevalonic aciduria pathway, and the child syndrome pathway. Outside of the human body, dimethylallylpyrophosphate can be found in a number of food items such as ucuhuba, yellow wax bean, white cabbage, and european plum. This makes dimethylallylpyrophosphate a potential biomarker for the consumption of these food products. Dimethylallyl pyrophosphate (or -diphosphate) (DMAPP) is an intermediate product of both mevalonic acid (MVA) pathway and DOXP/MEP pathway. It is an isomer of isopentenyl pyrophosphate (IPP) and exists in virtually all life forms. (wikipedia).358-72-5C0023564716057CPD-4211627DB01785CC(C)=CCO[P@](O)(=O)OP(O)(O)=OC5H12O7P2InChI=1S/C5H12O7P2/c1-5(2)3-4-11-14(9,10)12-13(6,7)8/h3H,4H2,1-2H3,(H,9,10)(H2,6,7,8)CBIDRCWHNCKSTO-UHFFFAOYSA-N({hydroxy[(3-methylbut-2-en-1-yl)oxy]phosphoryl}oxy)phosphonic acid246.0921246.005825762-1.583dimethylallyl diphosphate0-2FDB0224341,1-dimethyl-4-phenylpiperazinium iodide;2-isopentenyl diphosphate;3,3-dimethylallyl pyrophosphate;3-methyl-2-buten-1-ol pyrophosphate;3-methyl-2-buten-1-ol trihydrogen pyrophosphate;3-methyl-2-butenyl pyrophosphate;3-methylbut-2-enyl pyrophosphate;Dmapp;Dmpp;Delta2-isopentenyl diphosphate;Delta2-isopentenyl-diphosphate;Dimethylallyl diphosphate;Dimethylallyl pyrophosphate;Dimethylallyl-pp;Dimethylallyl-ppi;Dimethylallyl-diphosphate;Dimethylallyl-pyrophosphate;Dimethylallylpyrophosphate;Diphosphoric acid mono(3-methyl-2-butenyl) ester;Ipe;Prenyl diphosphate;Prenyl-diphosphate;Delta-prenyl diphosphate;Monoprenyl diphosphate;2-isopentenyl diphosphoric acid;Dimethylallylpyrophosphoric acid;Delta2-isopentenyl diphosphoric acid;δ2-isopentenyl diphosphate;δ2-isopentenyl diphosphoric acid;Dimethylallyl pyrophosphoric acid;Monoprenyl diphosphoric acid;Prenyl diphosphoric acidPW_C000874Ipe81057309216123112251248815178924334121477408124035374993Geranyl-PPHMDB0001285Geranyl diphosphate is the precursor of monoterpenes, a large family of natural occurring C10 compounds predominately found in plants and animals. Geranyl diphosphate is regarded as a key intermediate in the steroid, isoprene and terpene biosynthesis pathways and is used by organisms in the biosynthesis of farnesyl pyrophosphate, geranylgeranyl pyrophosphate, cholesterol, terpenes and terpenoids. (wikipedia). In humans, geranyl diphosphate synthase (GPPS) catalyzes the condensation of dimethylallyl diphosphate (DMAPP) and isopentenyl diphosphate (IPP) to form geranyl diphosphate. Animals produce IPP through the mevalonate (MVA) pathway. Isoprenoid compounds have been implicated in several human disease states including coronary heart disease, blindness, infectious hepatitis and cancer. Geranyl pyrophosphate is an intermediate in the HMG-CoA reductase pathway used by organisms in the biosynthesis of terpenes and terpenoids. -- Wikipedia.763-10-0C0034144599517211GERANYL-PP393471DB02552CC(C)=CCC\C(C)=C\CO[P@@](=O)(O)OP(=O)(O)OC10H20O7P2InChI=1S/C10H20O7P2/c1-9(2)5-4-6-10(3)7-8-16-19(14,15)17-18(11,12)13/h5,7H,4,6,8H2,1-3H3,(H,14,15)(H2,11,12,13)/b10-7+GVVPGTZRZFNKDS-JXMROGBWSA-N[({[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid314.2091314.068426018-2.543geranyl diphosphate0-2FDB001463(2e)-3,7-dimethylocta-2,6-dien-1-yl trihydrogen diphosphate;Geranyl diphosphate;Geranyl-pp;Geranyl-diphosphate;Geranyl-pyrophosphate;Monoterpenyl diphosphate;Neryl diphosphate;Trans-geranyl pyrophosphate;Polyisopentenylpyrophosphate;Polyisopentenyldiphosphate;Trans-polyisopentenyldiphosphate;Polyprenyl diphosphate;Polyisopentenylpyrophosphoric acid;Polyisopentenyldiphosphoric acid;Trans-polyisopentenyldiphosphoric acid;Polyprenyl diphosphoric acidPW_C000993Gryl-PP808515988731119876091608282210123142251521830678925111121479122124037135228331-deoxy-D-xylulose 5-phosphate synthase 1A0A1I9LTC7DXPS14136644225228341-deoxy-D-xylulose 5-phosphate reductoisomerase, chloroplasticQ9XFS9
Enzyme of the plastid non-mevalonate pathway for isoprenoid biosynthesis that catalyzes the NADP-dependent rearrangement and reduction of 1-deoxy-D-xylulose-5-phosphate (DXP) to 2-C-methyl-D-erythritol 4-phosphate (MEP). Required for chloroplast development.
DXR41.1.1.267136646225228352-C-methyl-D-erythritol 4-phosphate cytidylyltransferase, chloroplasticP69834
Enzyme of the plastid non-mevalonate pathway for isoprenoid biosynthesis that catalyzes the formation of 4-diphosphocytidyl-2-C-methyl-D-erythritol from CTP and 2-C-methyl-D-erythritol 4-phosphate (MEP). Is essential for chloroplast development and required for pigments and gibberellins biosynthesis.
ISPD42.7.7.60136648225228364-diphosphocytidyl-2-C-methyl-D-erythritol kinase, chloroplasticO81014
Enzyme of the plastid non-mevalonate pathway for isoprenoid biosynthesis that catalyzes the phosphorylation of the position 2 hydroxy group of 4-diphosphocytidyl-2C-methyl-D-erythritol. Is essential for chloroplast development.
ISPE42.7.1.148136650225228372-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase, chloroplasticQ9CAK8
Enzyme of the plastid non-mevalonate pathway for isoprenoid biosynthesis that converts 4-diphosphocytidyl-2C-methyl-D-erythritol 2-phosphate into 2C-methyl-D-erythritol 2,4-cyclodiphosphate and CMP. Also converts 4-diphosphocytidyl-2C-methyl-D-erythritol into 2C-methyl-D-erythritol 3,4-cyclophosphate and CMP. Is essential for chloroplast development.
ISPF44.6.1.12136652225228384-hydroxy-3-methylbut-2-en-1-yl diphosphate synthase (ferredoxin), chloroplasticF4K0E8
Enzyme of the plastid non-mevalonate pathway for isoprenoid biosynthesis that converts 2-C-methyl-D-erythritol 2,4-cyclodiphosphate (ME-2,4cPP) into 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate. Is essential for chloroplast development and required for the salicylic acid (SA)-mediated disease resistance to biotrophic pathogens.
ISPG41.17.7.1136654225228394-hydroxy-3-methylbut-2-enyl diphosphate reductase, chloroplasticQ94B35
Enzyme of the plastid non-mevalonate pathway for isoprenoid biosynthesis that converts 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate into isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP). Is essential for chloroplast development.
ISPH41.17.7.413665622522840Geranylgeranyl pyrophosphate synthase 6, mitochondrialO22043
Catalyzes the trans-addition of the three molecules of IPP onto DMAPP to form geranylgeranyl pyrophosphate.
GGPP642.5.1.-, 2.5.1.1, 2.5.1.29, 2.5.1.1013665822422841Isopentenyl-diphosphate Delta-isomerase II, chloroplasticQ42553
Catalyzes the 1,3-allylic rearrangement of the homoallylic substrate isopentenyl (IPP) to its highly electrophilic allylic isomer, dimethylallyl diphosphate (DMAPP).
IPP245.3.3.2136660225133901-Deoxy-D-xylulose 5-phosphate synthase 14PW_P01339023234228331136645225133911-Deoxy-D-xylulose 5-phosphate reductoisomerase, chloroplastic4PW_P01339123235228341136647225133922-C-methyl-D-erythritol 4-phosphate cytidylyltransferase, chloroplastic4PW_P01339223236228351136649225133934-diphosphocytidyl-2-C-methyl-D-erythritol kinase, chloroplastic4PW_P01339323237228361136651225133942-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase, chloroplastic4PW_P01339423238228371136653225133954-hydroxy-3-methylbut-2-en-1-yl diphosphate synthase (ferredoxin), chloroplastic4PW_P01339523239228381136655225133964-Hydroxy-3-methylbut-2-enyl diphosphate reductase, chloroplastic4PW_P0133962324022839113665722513397Geranylgeranyl pyrophosphate synthase 6, mitochondrial4PW_P0133972324122840113665922413398Isopentenyl-diphosphate Delta-isomerase II, chloroplastic4PW_P01339823242228411136661225180089PW_R180089Right6797998691Compoundfalse6798001641Compoundfalse6798019441Compoundfalse16994413390180091PW_R180091Right679804426091Compoundfalse679805571Compoundfalse679806400341Compoundfalse679807429371Compoundfalse6798081701Compoundfalse169946133922.7.7.60180092PW_R180092Right6798099441Compoundfalse6798101461Compoundfalse679811400341Compoundfalse679812426091Compoundfalse6798131431Compoundfalse16994713391180093PW_R180093Right679814429371Compoundfalse67981510341Compoundfalse679816400341Compoundfalse679817429381Compoundfalse6798184141Compoundfalse169948133932.7.1.148180094PW_R180094Right679819429381Compoundfalse679820641Compoundfalse679821429391Compoundfalse169949133944.6.1.12180095PW_R180095Right679822429391Compoundfalse679823400341Compoundfalse679824411521Compoundfalse679825405582Compoundfalse67982614201Compoundfalse169950133951.17.7.1180096PW_R180096Right679827411521Compoundfalse679828400342Compoundfalse679829411022Compoundfalse67983010391Compoundfalse67983114201Compoundfalse679832411012Compoundfalse169951133961.17.7.4180097PW_R180097Right67983310391Compoundfalse6798348741Compoundfalse6798359931Compoundfalse6798361701Compoundfalse169952133972.5.1.-,2.5.1.1, 2.5.1.29, 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