2.02012-05-31 10:25:46 -06002015-09-13 12:56:07 -0600ECMDB00292M2MDB000121XanthineXanthine is an intermediate in the degradation of adenosine monophosphate to uric acid, being formed by oxidation of hypoxanthine. The methylated xanthine compounds caffeine, theobromine, and theophylline and their derivatives are used in medicine for their bronchodilator effects. (Dorland, 28th ed.)1H-Purine-2,6-diol2,6(1,3)-Purinedion2,6-Dihydroxypurine2,6-Dioxopurine3,7-Dihydro-1H-purine-2,6-dione3,7-Dihydropurine-2,6-dione9H-Purine-2,6(1H,3H)-dione9H-Purine-2,6-diolDioxopurineIsoxanthinePseudoxanthinePurine-2,6(1H,3H)-dionePurine-2,6-diolXanthic oxideXanthinXanthineC5H4N4O2152.1109152.0334253922,3,6,7-tetrahydro-1H-purine-2,6-dionexanthine69-89-6O=C1NC2=C(NC=N2)C(=O)N1InChI=1S/C5H4N4O2/c10-4-2-3(7-1-6-2)8-5(11)9-4/h1H,(H3,6,7,8,9,10,11)LRFVTYWOQMYALW-UHFFFAOYSA-NSolidCytosolExtra-organismPeriplasmlogp-0.65logs-1.49solubility4.91e+00 g/lmelting_point>300 oClogp-0.21pka_strongest_acidic7.95pka_strongest_basic-0.7iupac2,3,6,7-tetrahydro-1H-purine-2,6-dioneaverage_mass152.1109mono_mass152.033425392smilesO=C1NC2=C(NC=N2)C(=O)N1formulaC5H4N4O2inchiInChI=1S/C5H4N4O2/c10-4-2-3(7-1-6-2)8-5(11)9-4/h1H,(H3,6,7,8,9,10,11)inchikeyLRFVTYWOQMYALW-UHFFFAOYSA-Npolar_surface_area86.88refractivity36.92polarizability12.7rotatable_bond_count0acceptor_count3donor_count3physiological_charge0formal_charge0Purine metabolismec00230Microbial metabolism in diverse environmentsec01120Metabolic pathwayseco01100purine 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.PW002091Metabolicpurine ribonucleosides degradation to ribose-1-phosphatePWY0-1296adenosine nucleotides degradation IISALVADEHYPOX-PWYguanosine nucleotides degradation IIIPWY-6608xanthine and xanthosine salvageSALVPURINE2-PWYSpecdb::CMs522Specdb::CMs2708Specdb::CMs30712Specdb::CMs32321Specdb::CMs146604Specdb::EiMs412Specdb::NmrOneD1316Specdb::NmrOneD3280Specdb::NmrOneD4815Specdb::NmrOneD4816Specdb::NmrOneD143350Specdb::NmrOneD143351Specdb::NmrOneD143352Specdb::NmrOneD143353Specdb::NmrOneD143354Specdb::NmrOneD143355Specdb::NmrOneD143356Specdb::NmrOneD143357Specdb::NmrOneD143358Specdb::NmrOneD143359Specdb::NmrOneD143360Specdb::NmrOneD143361Specdb::NmrOneD143362Specdb::NmrOneD143363Specdb::NmrOneD143364Specdb::NmrOneD143365Specdb::NmrOneD143366Specdb::NmrOneD143367Specdb::NmrOneD143368Specdb::NmrOneD143369Specdb::MsMs495Specdb::MsMs496Specdb::MsMs497Specdb::MsMs3930Specdb::MsMs20087Specdb::MsMs20088Specdb::MsMs20089Specdb::MsMs21638Specdb::MsMs21639Specdb::MsMs21640Specdb::MsMs439121Specdb::MsMs440035Specdb::MsMs447350Specdb::MsMs2236517Specdb::MsMs2236881Specdb::MsMs2238648Specdb::MsMs2240648Specdb::MsMs2241065Specdb::MsMs2242679Specdb::MsMs2242921Specdb::MsMs2242940Specdb::MsMs2243142Specdb::MsMs2245016Specdb::MsMs2245116Specdb::MsMs2247120Specdb::NmrTwoD1014Specdb::NmrTwoD1259HMDB0029211881151C0038517712XANTHINEXANXanthineKeseler, I. 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J Chromatogr. 1990 Nov 30;533:73-86.2081781Ginsburg I: Could synergistic interactions among reactive oxygen species, proteinases, membrane-perforating enzymes, hydrolases, microbial hemolysins and cytokines be the main cause of tissue damage in infectious and inflammatory conditions? Med Hypotheses. 1998 Oct;51(4):337-46.9824842Procedure for the production of xanthine and xanthine-like materials. Fr. (1967), 4 pp.http://hmdb.ca/system/metabolites/msds/000/000/213/original/HMDB00292.pdf?1358896206Hypoxanthine phosphoribosyltransferaseP0A9M2HPRT_ECOLIhpthttp://ecmdb.ca/proteins/P0A9M2.xmlXanthine phosphoribosyltransferaseP0A9M5XGPT_ECOLIgpthttp://ecmdb.ca/proteins/P0A9M5.xmlPurine nucleoside phosphorylase deoD-typeP0ABP8DEOD_ECOLIdeoDhttp://ecmdb.ca/proteins/P0ABP8.xmlNon-specific ribonucleoside hydrolase rihCP22564RIHC_ECOLIrihChttp://ecmdb.ca/proteins/P22564.xmlGuanine deaminaseP76641GUAD_ECOLIguaDhttp://ecmdb.ca/proteins/P76641.xmlPutative xanthine dehydrogenase yagS FAD-binding subunitP77324YAGS_ECOLIyagShttp://ecmdb.ca/proteins/P77324.xmlPutative xanthine dehydrogenase yagR molybdenum-binding subunitP77489YAGR_ECOLIyagRhttp://ecmdb.ca/proteins/P77489.xmlXanthine dehydrogenase molybdenum-binding subunitQ46799XDHA_ECOLIxdhAhttp://ecmdb.ca/proteins/Q46799.xmlXanthine dehydrogenase FAD-binding subunitQ46800XDHB_ECOLIxdhBhttp://ecmdb.ca/proteins/Q46800.xmlXanthine dehydrogenase iron-sulfur-binding subunitQ46801XDHC_ECOLIxdhChttp://ecmdb.ca/proteins/Q46801.xmlXanthosine phosphorylaseP45563XAPA_ECOLIxapAhttp://ecmdb.ca/proteins/P45563.xmlPaoABC aldehyde oxidoreductase, 2Fe-2S subunitP77165paoAhttp://ecmdb.ca/proteins/P77165.xmlXanthine permease XanPP0AGM9XANP_ECOLIxanPhttp://ecmdb.ca/proteins/P0AGM9.xmlXanthine permease XanQP67444XANQ_ECOLIxanQhttp://ecmdb.ca/proteins/P67444.xmlOuter membrane protein NP77747OMPN_ECOLIompNhttp://ecmdb.ca/proteins/P77747.xmlOuter membrane pore protein EP02932PHOE_ECOLIphoEhttp://ecmdb.ca/proteins/P02932.xmlOuter membrane protein FP02931OMPF_ECOLIompFhttp://ecmdb.ca/proteins/P02931.xmlOuter membrane protein CP06996OMPC_ECOLIompChttp://ecmdb.ca/proteins/P06996.xmlWater + Hypoxanthine + NAD > Hydrogen ion + NADH + XanthineR01768RXN-7682Water + NAD + Xanthine <> Hydrogen ion + NADH + Uric acidR02103RXN0-901Water + Xanthosine > Ribose + XanthinePhosphoribosyl pyrophosphate + Xanthine <> Pyrophosphate + Xanthylic acidR02142XANPRIBOSYLTRAN-RXNPhosphate + Xanthosine <> Ribose-1-phosphate + XanthineXANTHOSINEPHOSPHORY-RXNGuanine + Hydrogen ion + Water > Ammonium + XanthineGuanine + Water <> Xanthine + AmmoniaR01676GUANINE-DEAMINASE-RXNHypoxanthine + NAD + Water <> Xanthine + NADH + Hydrogen ionR01768Xanthylic acid + Pyrophosphate <> Xanthine + Phosphoribosyl pyrophosphateR02142Xanthosine + Phosphate <> Xanthine + alpha-D-Ribose 1-phosphateR02297isoguanine + Water > Xanthine + AmmoniaRXN0-6708Water + Guanine > Ammonia + XanthineGUANINE-DEAMINASE-RXNXanthosine + Water > D-ribose + XanthineRXN0-363Xanthine + NAD + Water > Uric acid + NADH + Hydrogen ionRXN0-901Xanthylic acid + Pyrophosphate < Xanthine + Phosphoribosyl pyrophosphateR02142XANPRIBOSYLTRAN-RXNXanthosine + Phosphate > Ribose-1-phosphate + XanthineXANTHOSINEPHOSPHORY-RXNXanthine + NAD + Water > Uric acid + NADHHypoxanthine + NAD + Water > Xanthine + NADHXanthylic acid + Pyrophosphate > Phosphoribosyl pyrophosphate + XanthineXanthine + Phosphoribosyl pyrophosphate > Xanthylic acid + PyrophosphatePW_R006088Guanine + Water <> Xanthine + AmmoniaWater + Hypoxanthine + NAD > Hydrogen ion + NADH + XanthineWater + Hypoxanthine + NAD > Hydrogen ion + NADH + XanthineWater + Hypoxanthine + NAD > Hydrogen ion + NADH + Xanthine