2.02012-05-31 10:23:32 -06002015-09-13 12:56:06 -0600ECMDB00195M2MDB000082InosineInosine is purine nucleoside that has hypoxanthine linked by the N9 nitrogen to the C1 carbon of ribose. It is an intermediate in the degradation of purines and purine nucleosides to uric acid and in pathways of purine salvage. It also occurs in the anticodon of certain transfer RNA molecules. (Dorland, 28th ed)(-)-Inosine1,9-Dihydro-9-b-D-ribofuranosyl-6H-Purin-6-one1,9-dihydro-9-b-delta-Ribofuranosyl-6H-purin-6-one1,9-dihydro-9-b-δ-Ribofuranosyl-6H-purin-6-one1,9-Dihydro-9-beta-D-ribofuranosyl-6H-purin-6-one1,9-Dihydro-9-beta-delta-ribofuranosyl-6H-purin-6-one1,9-dihydro-9-β-D-Ribofuranosyl-6H-purin-6-one1,9-dihydro-9-β-δ-Ribofuranosyl-6H-purin-6-one9-b-D-Ribofuranosyl-Hypoxanthine9-b-D-Ribofuranosylhypoxanthine9-b-delta-Ribofuranosyl-hypoxanthine9-b-delta-Ribofuranosylhypoxanthine9-b-δ-Ribofuranosyl-hypoxanthine9-b-δ-Ribofuranosylhypoxanthine9-beta-D-Ribofuranosyl-Hypoxanthine9-beta-D-Ribofuranosylhypoxanthine9-beta-delta-Ribofuranosyl-Hypoxanthine9-beta-delta-Ribofuranosylhypoxanthine9-β-D-Ribofuranosyl-hypoxanthine9-β-D-Ribofuranosylhypoxanthine9-β-δ-Ribofuranosyl-hypoxanthine9-β-δ-Ribofuranosylhypoxanthine9b-D-Ribofuranosylhypoxanthine9b-delta-Ribofuranosylhypoxanthine9b-δ-Ribofuranosylhypoxanthine9beta-D-Ribofuranosylhypoxanthine9beta-delta-Ribofuranosylhypoxanthine9β-D-Ribofuranosylhypoxanthine9β-δ-RibofuranosylhypoxanthineAtorelb-D-Ribofuranoside hypoxanthine-9b-delta-Ribofuranoside hypoxanthine-9b-Inosineb-δ-Ribofuranoside hypoxanthine-9Beta-D-Ribofuranoside hypoxanthine-9Beta-delta-Ribofuranoside hypoxanthine-9Beta-InosineHXRHypoxanthine 9-b-D-ribofuranosideHypoxanthine 9-b-delta-ribofuranosideHypoxanthine 9-b-δ-ribofuranosideHypoxanthine 9-beta-D-ribofuranosideHypoxanthine 9-beta-delta-ribofuranosideHypoxanthine 9-β-D-ribofuranosideHypoxanthine 9-β-δ-ribofuranosideHypoxanthine D-ribosideHypoxanthine nucleosideHypoxanthine ribonucleosideHypoxanthine ribosideHypoxanthine-9 b-D-ribofuranosideHypoxanthine-9 b-delta-ribofuranosideHypoxanthine-9 b-δ-ribofuranosideHypoxanthine-9 beta-D-RibofuranosideHypoxanthine-9 beta-delta-RibofuranosideHypoxanthine-9 β-D-ribofuranosideHypoxanthine-9 β-δ-ribofuranosideHypoxanthine-9-b-D-ribofuranosideHypoxanthine-9-b-delta-ribofuranosideHypoxanthine-9-b-δ-ribofuranosideHypoxanthine-9-beta-D-ribofuranosideHypoxanthine-9-beta-delta-ribofuranosideHypoxanthine-9-D-ribofuranosideHypoxanthine-9-delta-ribofuranosideHypoxanthine-9-β-D-ribofuranosideHypoxanthine-9-β-δ-ribofuranosideHypoxanthine-9-δ-ribofuranosideHypoxanthine-riboseHypoxanthosineIndole-3-carboxaldehydeInoInosieIso-prinosineOxiaminPanholic-LPantholic-LRibonosineRiboxineSelferTrophicardylβ-D-Ribofuranoside hypoxanthine-9β-Inosineβ-δ-Ribofuranoside hypoxanthine-9C10H12N4O5268.2261268.0807695149-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-3H-purin-6-oneinosine58-63-9OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1NC=NC2=OInChI=1S/C10H12N4O5/c15-1-4-6(16)7(17)10(19-4)14-3-13-5-8(14)11-2-12-9(5)18/h2-4,6-7,10,15-17H,1H2,(H,11,12,18)/t4-,6-,7-,10-/m1/s1UGQMRVRMYYASKQ-KQYNXXCUSA-NSolidCytosolExtra-organismPeriplasmmelting_point218 oClogp-2pka_strongest_acidic6.94pka_strongest_basic2.74iupac9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-3H-purin-6-oneaverage_mass268.2261mono_mass268.080769514smilesOC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1NC=NC2=OformulaC10H12N4O5inchiInChI=1S/C10H12N4O5/c15-1-4-6(16)7(17)10(19-4)14-3-13-5-8(14)11-2-12-9(5)18/h2-4,6-7,10,15-17H,1H2,(H,11,12,18)/t4-,6-,7-,10-/m1/s1inchikeyUGQMRVRMYYASKQ-KQYNXXCUSA-Npolar_surface_area129.2refractivity60.9polarizability24.6rotatable_bond_count2acceptor_count8donor_count4physiological_charge0formal_charge0Purine metabolismec00230Metabolic pathwayseco01100adenine and adenosine salvage IThe salvage of adenine begins with adenine being transporter into the cytosol through a adeP hydrogen symporter. Once in the cytosol adenine is degraded by reacting with a ribose-1-phosphate through an adenosine phosphorylase resulting in the release of a phosphate and adenosine. Adenosine is then deaminated by reacting with water, a hydrogen ion and an adenosine deaminase resulting in the release of an ammonium and a inosine . Inosine then reacts with a phosphate through a inosine phosphorylase resulting in the release of a ribose 1-phosphate and a hypoxanthine. Hypoxanthine reacts with a PRPP through a hypoxanthine phosphoribosyltransferase resulting in the release of a pyrophosphate and a IMP molecule.PW002069Metabolicadenine and adenosine salvage IIThe salvage of adenine begins with adenine being transporter into the cytosol through a adeP hydrogen symporter. Once in the cytosol adenine is degraded by reacting with a ribose-1-phosphate through an adenosine phosphorylase resulting in the release of a phosphate and adenosine. Adenosine is then deaminated by reacting with water, a hydrogen ion and an adenosine deaminase resulting in the release of an ammonium and a inosine . Inosine can then be phosphorylated through an ATP driven inosine kinase resulting in the release of an ADP, a hydrogen ion and a IMPPW002071Metabolicpurine ribonucleosides degradationPurine ribonucleoside degradation leads to the production of alpha-D-ribose-1-phosphate.
Xanthosine is transported into the cytosol through a xapB. Once in the cytosol xanthosine interacts with phosphate through a xanthosine phosphorylase resulting in the release of a xanthine and a alpha-D-ribose-1-phosphate.
Adenosine is transported through a nupC or a nupG transporter, once inside the cytosol it can either react with a phosphate through a adenosine phosphorylase resultin in the release of a adenine and an alpha-D-ribose-1-phosphate. Adenosine reacts with water and hydrogen ion through a adenosine deaminase resulting in the release of ammonium and inosine. Inosine reacts with phosphate through a inosine phosphorylase resulting in the release of a hypoxanthine and an alpha-D-ribose-1-phosphate.
Guanosine reacts with a phosphate through a guanosine phosphorylase resulting in the release of a guanine and a alpha-D-ribose-1-phosphate.PW002076Metabolicadenosine nucleotides degradationThe degradation of of adenosine nucleotides starts with AMP reacting with water through a nucleoside monophosphate phosphatase results in the release of phosphate and a adenosine. Adenosine reacts with water and hydrogen ion through an adenosine deaminase resulting in the release of ammonium and a inosine. Inosine reacts with phosphate through a inosine phosphorylase resulting in the release of an alpha-D-ribose-1-phosphate and an hypoxanthine. Hypoxanthine reacts with a water molecule and a NAD molecule through an hypoxanthine hydroxylase resulting in the release of an hydrogen ion, an NADH and a xanthine. Xanthine in turn is degraded by reacting with a water molecule and a NAD through xanthine NAD oxidoreductase resulting in the release of NADH, a hydrogen ion and urate.PW002091Metabolicadenine and adenosine salvage IIIPWY-6609adenine and adenosine salvage VPWY-6611purine ribonucleosides degradation to ribose-1-phosphatePWY0-1296adenosine nucleotides degradation IISALVADEHYPOX-PWYSpecdb::CMs448Specdb::CMs449Specdb::CMs2029Specdb::CMs22590Specdb::CMs30576Specdb::CMs30880Specdb::CMs31063Specdb::CMs37351Specdb::CMs163703Specdb::CMs1053958Specdb::CMs1053960Specdb::CMs1053962Specdb::CMs1053964Specdb::CMs1053965Specdb::CMs1053967Specdb::CMs1053969Specdb::CMs1053971Specdb::CMs1053973Specdb::CMs1053975Specdb::CMs1053977Specdb::CMs1053979Specdb::CMs1053981Specdb::CMs1053983Specdb::CMs1053985Specdb::CMs1053986Specdb::NmrOneD1174Specdb::NmrOneD4906Specdb::NmrOneD142810Specdb::NmrOneD142811Specdb::NmrOneD142812Specdb::NmrOneD142813Specdb::NmrOneD142814Specdb::NmrOneD142815Specdb::NmrOneD142816Specdb::NmrOneD142817Specdb::NmrOneD142818Specdb::NmrOneD142819Specdb::NmrOneD142820Specdb::NmrOneD142821Specdb::NmrOneD142822Specdb::NmrOneD142823Specdb::NmrOneD142824Specdb::NmrOneD142825Specdb::NmrOneD142826Specdb::NmrOneD142827Specdb::NmrOneD142828Specdb::NmrOneD142829Specdb::MsMs3551Specdb::MsMs3552Specdb::MsMs3553Specdb::MsMs3554Specdb::MsMs3555Specdb::MsMs3556Specdb::MsMs3557Specdb::MsMs3558Specdb::MsMs3559Specdb::MsMs3560Specdb::MsMs3561Specdb::MsMs3562Specdb::MsMs3563Specdb::MsMs3568Specdb::MsMs437935Specdb::MsMs437936Specdb::MsMs437937Specdb::MsMs437938Specdb::MsMs437939Specdb::MsMs438696Specdb::MsMs438808Specdb::MsMs438809Specdb::MsMs438857Specdb::MsMs438858Specdb::MsMs439079Specdb::NmrTwoD992Specdb::NmrTwoD1200HMDB0019560215799C0029417596INOSINENOSInosineKeseler, 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-D114.22080510van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25.17765195Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948.18331064Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597.17379776Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4.19212411Eells JT, Spector R: Purine and pyrimidine base and nucleoside concentrations in human cerebrospinal fluid and plasma. Neurochem Res. 1983 Nov;8(11):1451-7.6656991Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2(1):18.15882454Chantin C, Bonin B, Boulieu R, Bory C: Liquid-chromatographic study of purine metabolism abnormalities in purine nucleoside phosphorylase deficiency. Clin Chem. 1996 Feb;42(2):326-8.8595732Castro-Gago M, Cid E, Trabazo S, Pavon P, Camina F, Rodriguez-Segade S, Einis Punal J, Rodriguez-Nunez A: Cerebrospinal fluid purine metabolites and pyrimidine bases after brief febrile convulsions. Epilepsia. 1995 May;36(5):471-4.7614924Rodriguez-Nunez A, Camina F, Lojo S, Rodriguez-Segade S, Castro-Gago M: Concentrations of nucleotides, nucleosides, purine bases and urate in cerebrospinal fluid of children with meningitis. Acta Paediatr. 1993 Oct;82(10):849-52.8241644Scott GS, Spitsin SV, Kean RB, Mikheeva T, Koprowski H, Hooper DC: Therapeutic intervention in experimental allergic encephalomyelitis by administration of uric acid precursors. Proc Natl Acad Sci U S A. 2002 Dec 10;99(25):16303-8. Epub 2002 Nov 25.12451183Nakao T, Nagai F, Nakao M: Posttransfusion viability of rabbit erythrocytes preserved in a medium containing inosine, adenine, and isoosmotic sucrose. Vox Sang. 1982;42(4):217-22.7090336Harkness RA, Lund RJ: Cerebrospinal fluid concentrations of hypoxanthine, xanthine, uridine and inosine: high concentrations of the ATP metabolite, hypoxanthine, after hypoxia. J Clin Pathol. 1983 Jan;36(1):1-8.6681617Hsiao G, Lin KH, Chang Y, Chen TL, Tzu NH, Chou DS, Sheu JR: Protective mechanisms of inosine in platelet activation and cerebral ischemic damage. Arterioscler Thromb Vasc Biol. 2005 Sep;25(9):1998-2004. Epub 2005 Jun 23.15976325Jabs CM, Sigurdsson GH, Neglen P: Plasma levels of high-energy compounds compared with severity of illness in critically ill patients in the intensive care unit. Surgery. 1998 Jul;124(1):65-72.9663253Fazekas L, Horkay F, Kekesi V, Huszar E, Barat E, Fazekas R, Szabo T, Juhasz-Nagy A, Naszlady A: Enhanced accumulation of pericardial fluid adenosine and inosine in patients with coronary artery disease. Life Sci. 1999;65(10):1005-12.10499868Mattle HP, Lienert C, Greeve I: [Uric acid and multiple sclerosis] Ther Umsch. 2004 Sep;61(9):553-5.15493114Fukumori Y, Takeda H, Fujisawa T, Ushijima K, Onodera S, Shiomi N: Blood glucose and insulin concentrations are reduced in humans administered sucrose with inosine or adenosine. J Nutr. 2000 Aug;130(8):1946-9.10917906Burger DM, Kraayeveld CL, Meenhorst PL, Mulder JW, Hoetelmans RM, Koks CH, Beijnen JH: Study on didanosine concentrations in cerebrospinal fluid. Implications for the treatment and prevention of AIDS dementia complex. Pharm World Sci. 1995 Nov 24;17(6):218-21.8597780Mabley JG, Rabinovitch A, Suarez-Pinzon W, Hasko G, Pacher P, Power R, Southan G, Salzman A, Szabo C: Inosine protects against the development of diabetes in multiple-low-dose streptozotocin and nonobese diabetic mouse models of type 1 diabetes. Mol Med. 2003 Mar-Apr;9(3-4):96-104.12865945Yamamoto 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):438-42.11912550Kurtz TW, Kabra PM, Booth BE, Al-Bander HA, Portale AA, Serena BG, Tsai HC, Morris RC Jr: Liquid-chromatographic measurements of inosine, hypoxanthine, and xanthine in studies of fructose-induced degradation of adenine nucleotides in humans and rats. Clin Chem. 1986 May;32(5):782-6.3698269Niwa T, Takeda N, Yoshizumi H: RNA metabolism in uremic patients: accumulation of modified ribonucleosides in uremic serum. Technical note. Kidney Int. 1998 Jun;53(6):1801-6.9607216Osborne WR, Hammond WP, Dale DC: Human cyclic hematopoiesis is associated with aberrant purine metabolism. J Lab Clin Med. 1985 Apr;105(4):403-9.3981053Shi, Qingshan; Qiu, Yutang; Li, Liangqiu; Lin, Xiaoping. New inosine-producing bacterium and method for producing inosine. Faming Zhuanli Shenqing Gongkai Shuomingshu (2003), 6 pp. http://hmdb.ca/system/metabolites/msds/000/000/138/original/HMDB00195.pdf?1358894588Protein ushAP07024USHA_ECOLIushAhttp://ecmdb.ca/proteins/P07024.xmlMultifunctional protein surEP0A840SURE_ECOLIsurEhttp://ecmdb.ca/proteins/P0A840.xml5'-nucleotidase yjjGP0A8Y1YJJG_ECOLIyjjGhttp://ecmdb.ca/proteins/P0A8Y1.xmlPurine nucleoside phosphorylase deoD-typeP0ABP8DEOD_ECOLIdeoDhttp://ecmdb.ca/proteins/P0ABP8.xmlClass B acid phosphataseP0AE22APHA_ECOLIaphAhttp://ecmdb.ca/proteins/P0AE22.xmlInosine-guanosine kinaseP0AEW6INGK_ECOLIgskhttp://ecmdb.ca/proteins/P0AEW6.xmlAdenosine deaminaseP22333ADD_ECOLIaddhttp://ecmdb.ca/proteins/P22333.xmlNon-specific ribonucleoside hydrolase rihCP22564RIHC_ECOLIrihChttp://ecmdb.ca/proteins/P22564.xmlPyrimidine-specific ribonucleoside hydrolase rihBP33022RIHB_ECOLIrihBhttp://ecmdb.ca/proteins/P33022.xml5'-nucleotidase yfbRP76491YFBR_ECOLIyfbRhttp://ecmdb.ca/proteins/P76491.xmlXanthosine phosphorylaseP45563XAPA_ECOLIxapAhttp://ecmdb.ca/proteins/P45563.xmltRNA-specific adenosine deaminaseP68398TADA_ECOLItadAhttp://ecmdb.ca/proteins/P68398.xmlXanthosine permeaseP45562XAPB_ECOLIxapBhttp://ecmdb.ca/proteins/P45562.xmlNucleoside permease nupCP0AFF2NUPC_ECOLInupChttp://ecmdb.ca/proteins/P0AFF2.xmlNucleoside permease nupGP0AFF4NUPG_ECOLInupGhttp://ecmdb.ca/proteins/P0AFF4.xmlNucleoside-specific channel-forming protein tsxP0A927TSX_ECOLItsxhttp://ecmdb.ca/proteins/P0A927.xmlWater + Inosinic acid > Inosine + PhosphateInosine + Phosphate <> Hypoxanthine + Ribose-1-phosphateINOPHOSPHOR-RXNWater + Inosine > Hypoxanthine + RiboseR01770Adenosine triphosphate + Inosine <> ADP + Hydrogen ion + Inosinic acidR01131INOSINEKIN-RXNAdenosine + Hydrogen ion + Water > Inosine + AmmoniumInosinic acid + Water <> Inosine + PhosphateR01126Adenosine triphosphate + Inosine <> ADP + Inosinic acidR01131Adenosine + Water <> Inosine + AmmoniaR01560Inosine + Water <> Hypoxanthine + RiboseR01770Inosine + Phosphate <> Hypoxanthine + alpha-D-Ribose 1-phosphateR01863Water + Adenosine > Ammonia + InosineR01560ADENODEAMIN-RXNInosine + Water > D-ribose + HypoxanthineINOSINE-NUCLEOSIDASE-RXNInosine + Adenosine triphosphate > Hydrogen ion + Inosinic acid + ADPINOSINEKIN-RXNAdenosine triphosphate + Inosine > ADP + Inosinic acidInosine + Phosphate > Ribose-1-phosphate + HypoxanthinePW_R006050Water + Adenosine > Ammonia + Inosine48 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L GlucoBioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h31.1uM0.037 oCBW25113Stationary Phase, glucose limited1244000Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597.17379776