2.02012-05-31 13:50:54 -06002015-09-13 15:15:23 -0600ECMDB01366M2MDB000356PurinePurine is a member of the chemical class known as Purines and Purine Derivatives. These are aromatic heterocyclic compounds containing a purine moiety, which is formed a pyrimidine-ring ring fused to an imidazole ring. A purine is a heterocyclic aromatic organic compound, consisting of a pyrimidine ring fused to an imidazole ring. Purines, including substituted purines and their tautomers, are the most widely distributed kind of nitrogen-containing heterocycle in nature. Purines and pyrimidines make up the two groups of nitrogenous bases, including the two groups of nucleotide bases. Two of the four deoxyribonucleotides and two of the four ribonucleotides, the respective building-blocks of DNA and RNA, are purines. Purine is invovled in microbial metabolism in diverse environments.1,3,7-Trimethyl-2,6-dioxopurine1,3,7-Trimethylxanthine1H-Purine3,5, 7-Triazaindole3,7-Dihydro-1,3,7-trimethyl-1H-Purine-2,6-dione6H-Imidazo[4,5-D]pyrimidine7-Methyltheophylline7H-Imidazo(4,5-D)pyrimidine7H-Purine9H-Purine9H-Purine (VAN)Alert-Pepb-PurineBeta-PurineCafeinaCaffedrineCaffeinCaffeineCafipelCFFCoffeineDasinDexitacDHCplusDiurexDurvitanGuaranineHycomineImidazo(4,5-D)pyrimidineIsopurineKoffeinMateinaMethyltheobromineMiudolNo-DozPhensalPropoxyphene Compound 65PurineRefresh'NSK 65 CompoundThein{6H-Imidazo[4,5-D]pyrimidine}{7H-Imidazo[4,} 5-D]pyrimidine{Imidazo[4,5-D]pyrimidine}β-PurineC5H4N4120.1121120.0435961487H-purinepurine120-73-0N1C=NC2=C1C=NC=N2InChI=1S/C5H4N4/c1-4-5(8-2-6-1)9-3-7-4/h1-3H,(H,6,7,8,9)KDCGOANMDULRCW-UHFFFAOYSA-NSolidCytoplasmPeriplasmlogp-0.19logs-0.35solubility5.35e+01 g/lmelting_point214 oClogp-0.34pka_strongest_acidic9.31pka_strongest_basic2.76iupac7H-purineaverage_mass120.1121mono_mass120.043596148smilesN1C=NC2=C1C=NC=N2formulaC5H4N4inchiInChI=1S/C5H4N4/c1-4-5(8-2-6-1)9-3-7-4/h1-3H,(H,6,7,8,9)inchikeyKDCGOANMDULRCW-UHFFFAOYSA-Npolar_surface_area54.46refractivity33.21polarizability10.9rotatable_bond_count0acceptor_count3donor_count1physiological_charge0formal_charge0Purine metabolismec00230Pyrimidine metabolismThe metabolism of pyrimidines begins with L-glutamine interacting with water molecule and a hydrogen carbonate through an ATP driven carbamoyl phosphate synthetase resulting in a hydrogen ion, an ADP, a phosphate, an L-glutamic acid and a carbamoyl phosphate. The latter compound interacts with an L-aspartic acid through a aspartate transcarbamylase resulting in a phosphate, a hydrogen ion and a N-carbamoyl-L-aspartate. The latter compound interacts with a hydrogen ion through a dihydroorotase resulting in the release of a water molecule and a 4,5-dihydroorotic acid. This compound interacts with an ubiquinone-1 through a dihydroorotate dehydrogenase, type 2 resulting in a release of an ubiquinol-1 and an orotic acid. The orotic acid then interacts with a phosphoribosyl pyrophosphate through a orotate phosphoribosyltransferase resulting in a pyrophosphate and an orotidylic acid. The latter compound then interacts with a hydrogen ion through an orotidine-5 '-phosphate decarboxylase, resulting in an release of carbon dioxide and an Uridine 5' monophosphate. The Uridine 5' monophosphate process to get phosphorylated by an ATP driven UMP kinase resulting in the release of an ADP and an Uridine 5--diphosphate.
Uridine 5-diphosphate can be metabolized in multiple ways in order to produce a Deoxyuridine triphosphate.
1.-Uridine 5-diphosphate interacts with a reduced thioredoxin through a ribonucleoside diphosphate reductase 1 resulting in the release of a water molecule and an oxidized thioredoxin and an dUDP. The dUDP is then phosphorylated by an ATP through a nucleoside diphosphate kinase resulting in the release of an ADP and a DeoxyUridine triphosphate.
2.-Uridine 5-diphosphate interacts with a reduced NrdH glutaredoxin-like protein through a Ribonucleoside-diphosphate reductase 1 resulting in a release of a water molecule, an oxidized NrdH glutaredoxin-like protein and a dUDP. The dUDP is then phosphorylated by an ATP through a nucleoside diphosphate kinase resulting in the release of an ADP and a DeoxyUridine triphosphate.
3.-Uridine 5-diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and an Uridinetriphosphate. The latter compound interacts with a reduced flavodoxin through ribonucleoside-triphosphate reductase resulting in the release of an oxidized flavodoxin, a water molecule and a Deoxyuridine triphosphate
4.-Uridine 5-diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and an Uridinetriphosphate The uridine triphosphate interacts with a L-glutamine and a water molecule through an ATP driven CTP synthase resulting in an ADP, a phosphate, a hydrogen ion, an L-glutamic acid and a cytidine triphosphate. The cytidine triphosphate interacts with a reduced flavodoxin through a ribonucleoside-triphosphate reductase resulting in the release of a water molecule, an oxidized flavodoxin and a dCTP. The dCTP interacts with a water molecule and a hydrogen ion through a dCTP deaminase resulting in a release of an ammonium molecule and a Deoxyuridine triphosphate.
5.-Uridine 5-diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and an Uridinetriphosphate The uridine triphosphate interacts with a L-glutamine and a water molecule through an ATP driven CTP synthase resulting in an ADP, a phosphate, a hydrogen ion, an L-glutamic acid and a cytidine triphosphate. The cytidine triphosphate then interacts spontaneously with a water molecule resulting in the release of a phosphate, a hydrogen ion and a CDP. The CDP then interacts with a reduced NrdH glutaredoxin-like protein through a ribonucleoside-diphosphate reductase 2 resulting in the release of a water molecule, an oxidized NrdH glutaredoxin-like protein and a dCDP. The dCDP is then phosphorylated through an ATP driven nucleoside diphosphate kinase resulting in an ADP and a dCTP. The dCTP interacts with a water molecule and a hydrogen ion through a dCTP deaminase resulting in a release of an ammonium molecule and a Deoxyuridine triphosphate.
6.-Uridine 5-diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and an Uridinetriphosphate The uridine triphosphate interacts with a L-glutamine and a water molecule through an ATP driven CTP synthase resulting in an ADP, a phosphate, a hydrogen ion, an L-glutamic acid and a cytidine triphosphate. The cytidine triphosphate then interacts spontaneously with a water molecule resulting in the release of a phosphate, a hydrogen ion and a CDP. The CDP interacts with a reduced thioredoxin through a ribonucleoside diphosphate reductase 1 resulting in a release of a water molecule, an oxidized thioredoxin and a dCDP. The dCDP is then phosphorylated through an ATP driven nucleoside diphosphate kinase resulting in an ADP and a dCTP. The dCTP interacts with a water molecule and a hydrogen ion through a dCTP deaminase resulting in a release of an ammonium molecule and a Deoxyuridine triphosphate.
The deoxyuridine triphosphate then interacts with a water molecule through a nucleoside triphosphate pyrophosphohydrolase resulting in a release of a hydrogen ion, a phosphate and a dUMP. The dUMP then interacts with a methenyltetrahydrofolate through a thymidylate synthase resulting in a dihydrofolic acid and a 5-thymidylic acid. Then 5-thymidylic acid is then phosphorylated through a nucleoside diphosphate kinase resulting in the release of an ADP and thymidine 5'-triphosphate.PW000942ec00240MetabolicNicotinate and nicotinamide metabolismec00760Metabolic pathwayseco01100Specdb::CMs1197Specdb::CMs1224Specdb::CMs3190Specdb::CMs31316Specdb::CMs31317Specdb::CMs134283Specdb::CMs142017Specdb::NmrOneD1295Specdb::NmrOneD1688Specdb::NmrOneD4669Specdb::NmrOneD4692Specdb::NmrOneD4734Specdb::NmrOneD4735Specdb::NmrOneD87852Specdb::NmrOneD87853Specdb::NmrOneD87854Specdb::NmrOneD87855Specdb::NmrOneD87856Specdb::NmrOneD87857Specdb::NmrOneD87858Specdb::NmrOneD87859Specdb::NmrOneD87860Specdb::NmrOneD87861Specdb::NmrOneD87862Specdb::NmrOneD87863Specdb::NmrOneD87864Specdb::NmrOneD87865Specdb::NmrOneD87866Specdb::NmrOneD87867Specdb::NmrOneD87868Specdb::NmrOneD87869Specdb::NmrOneD87870Specdb::MsMs1531Specdb::MsMs1532Specdb::MsMs1533Specdb::MsMs5203Specdb::MsMs5204Specdb::MsMs5205Specdb::MsMs5206Specdb::MsMs5207Specdb::MsMs19952Specdb::MsMs19953Specdb::MsMs19954Specdb::MsMs21503Specdb::MsMs21504Specdb::MsMs21505Specdb::MsMs440018Specdb::MsMs446762Specdb::MsMs446763Specdb::MsMs446764Specdb::MsMs446765Specdb::MsMs446766Specdb::MsMs451865Specdb::MsMs2227027Specdb::MsMs2227673Specdb::MsMs2229390Specdb::MsMs2230095Specdb::NmrTwoD1629HMDB013661015C1558717258PURINE-RINGPurineKeseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590.21097882Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114.22080510Gudbjornsson B, Zak A, Niklasson F, Hallgren R: Hypoxanthine, xanthine, and urate in synovial fluid from patients with inflammatory arthritides. Ann Rheum Dis. 1991 Oct;50(10):669-72.1958086Yamamoto T, Moriwaki Y, Cheng J, Takahashi S, Tsutsumi Z, Ka T, Hada T: Effect of inosine on the plasma concentration of uridine and purine bases. Metabolism. 2002 Apr;51(4):438-42.11912550van Os S, de Abreu R, Hopman J, Wethly K, Liem D, van de Bor M: Purine and pyrimidine metabolism and electrocortical brain activity during hypoxemia in near-term lambs. Pediatr Res. 2004 Jun;55(6):1018-25. Epub 2004 Mar 17.15028845Yegutkin GG, Samburski SS, Jalkanen S: Soluble purine-converting enzymes circulate in human blood and regulate extracellular ATP level via counteracting pyrophosphatase and phosphotransfer reactions. FASEB J. 2003 Jul;17(10):1328-30. Epub 2003 May 20.12759341Nakashima K, Inoue K, Mayahara K, Kuroda N, Hamachi Y, Akiyama S: Use of 3-(1,8-naphthalimido)propyl-modified silyl silica gel as a stationary phase for the high-performance liquid chromatographic separation of purine derivatives. J Chromatogr A. 1996 Jan 26;722(1-2):107-13.9019292Schmidt H, Siems WG, Grune T, Grauel EL: Concentration of purine compounds in the cerebrospinal fluid of infants suffering from sepsis, convulsions and hydrocephalus. J Perinat Med. 1995;23(3):167-74.8568608Lyoo IK, Demopulos CM, Hirashima F, Ahn KH, Renshaw PF: Oral choline decreases brain purine levels in lithium-treated subjects with rapid-cycling bipolar disorder: a double-blind trial using proton and lithium magnetic resonance spectroscopy. Bipolar Disord. 2003 Aug;5(4):300-6.12895208Burnstock G: Purine-mediated signalling in pain and visceral perception. Trends Pharmacol Sci. 2001 Apr;22(4):182-8.11282418Witte DP, Wiginton DA, Hutton JJ, Aronow BJ: Coordinate developmental regulation of purine catabolic enzyme expression in gastrointestinal and postimplantation reproductive tracts. J Cell Biol. 1991 Oct;115(1):179-90.1918135Shore PM, Jackson EK, Wisniewski SR, Clark RS, Adelson PD, Kochanek PM: Vascular endothelial growth factor is increased in cerebrospinal fluid after traumatic brain injury in infants and children. Neurosurgery. 2004 Mar;54(3):605-11; discussion 611-2.15028134Beaman, Alden G. New synthesis of purine. Journal of the American Chemical Society (1954), 76 5633-6.Purine nucleoside phosphorylase deoD-typeP0ABP8DEOD_ECOLIdeoDhttp://ecmdb.ca/proteins/P0ABP8.xmlPutative purine permease ybbYP77328YBBY_ECOLIybbYhttp://ecmdb.ca/proteins/P77328.xmlPutative purine permease ygfUQ46821YGFU_ECOLIygfUhttp://ecmdb.ca/proteins/Q46821.xmlPurine nucleoside + Inorganic phosphate > Purine + Ribose-1-phosphatePurine nucleoside + Phosphate + Purine deoxyribonucleoside <> Purine + Ribose-1-phosphate + Deoxyribose 1-phosphateR08368