2.0 2012-05-31 10:25:46 -0600 2015-09-13 12:56:07 -0600 ECMDB00292 M2MDB000121 Xanthine Xanthine 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-diol 2,6(1,3)-Purinedion 2,6-Dihydroxypurine 2,6-Dioxopurine 3,7-Dihydro-1H-purine-2,6-dione 3,7-Dihydropurine-2,6-dione 9H-Purine-2,6(1H,3H)-dione 9H-Purine-2,6-diol Dioxopurine Isoxanthine Pseudoxanthine Purine-2,6(1H,3H)-dione Purine-2,6-diol Xanthic oxide Xanthin Xanthine C5H4N4O2 152.1109 152.033425392 2,3,6,7-tetrahydro-1H-purine-2,6-dione xanthine 69-89-6 O=C1NC2=C(NC=N2)C(=O)N1 InChI=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-N Solid Cytosol Extra-organism Periplasm logp -0.65 ALOGPS logs -1.49 ALOGPS solubility 4.91e+00 g/l ALOGPS melting_point >300 oC logp -0.21 ChemAxon pka_strongest_acidic 7.95 ChemAxon pka_strongest_basic -0.7 ChemAxon iupac 2,3,6,7-tetrahydro-1H-purine-2,6-dione ChemAxon average_mass 152.1109 ChemAxon mono_mass 152.033425392 ChemAxon smiles O=C1NC2=C(NC=N2)C(=O)N1 ChemAxon formula C5H4N4O2 ChemAxon inchi InChI=1S/C5H4N4O2/c10-4-2-3(7-1-6-2)8-5(11)9-4/h1H,(H3,6,7,8,9,10,11) ChemAxon inchikey LRFVTYWOQMYALW-UHFFFAOYSA-N ChemAxon polar_surface_area 86.88 ChemAxon refractivity 36.92 ChemAxon polarizability 12.7 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 3 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Purine metabolism ec00230 Microbial metabolism in diverse environments ec01120 Metabolic pathways eco01100 purine ribonucleosides degradation Purine 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. PW002076 Metabolic adenosine nucleotides degradation The 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. PW002091 Metabolic purine ribonucleosides degradation to ribose-1-phosphate PWY0-1296 adenosine nucleotides degradation II SALVADEHYPOX-PWY guanosine nucleotides degradation III PWY-6608 xanthine and xanthosine salvage SALVPURINE2-PWY Specdb::CMs 522 Specdb::CMs 2708 Specdb::CMs 30712 Specdb::CMs 32321 Specdb::CMs 146604 Specdb::EiMs 412 Specdb::NmrOneD 1316 Specdb::NmrOneD 3280 Specdb::NmrOneD 4815 Specdb::NmrOneD 4816 Specdb::NmrOneD 143350 Specdb::NmrOneD 143351 Specdb::NmrOneD 143352 Specdb::NmrOneD 143353 Specdb::NmrOneD 143354 Specdb::NmrOneD 143355 Specdb::NmrOneD 143356 Specdb::NmrOneD 143357 Specdb::NmrOneD 143358 Specdb::NmrOneD 143359 Specdb::NmrOneD 143360 Specdb::NmrOneD 143361 Specdb::NmrOneD 143362 Specdb::NmrOneD 143363 Specdb::NmrOneD 143364 Specdb::NmrOneD 143365 Specdb::NmrOneD 143366 Specdb::NmrOneD 143367 Specdb::NmrOneD 143368 Specdb::NmrOneD 143369 Specdb::MsMs 495 Specdb::MsMs 496 Specdb::MsMs 497 Specdb::MsMs 3930 Specdb::MsMs 20087 Specdb::MsMs 20088 Specdb::MsMs 20089 Specdb::MsMs 21638 Specdb::MsMs 21639 Specdb::MsMs 21640 Specdb::MsMs 439121 Specdb::MsMs 440035 Specdb::MsMs 447350 Specdb::MsMs 2236517 Specdb::MsMs 2236881 Specdb::MsMs 2238648 Specdb::MsMs 2240648 Specdb::MsMs 2241065 Specdb::MsMs 2242679 Specdb::MsMs 2242921 Specdb::MsMs 2242940 Specdb::MsMs 2243142 Specdb::MsMs 2245016 Specdb::MsMs 2245116 Specdb::MsMs 2247120 Specdb::NmrTwoD 1014 Specdb::NmrTwoD 1259 HMDB00292 1188 1151 C00385 17712 XANTHINE XAN Xanthine Keseler, I. 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(1967), 4 pp. http://hmdb.ca/system/metabolites/msds/000/000/213/original/HMDB00292.pdf?1358896206 Hypoxanthine phosphoribosyltransferase P0A9M2 HPRT_ECOLI hpt http://ecmdb.ca/proteins/P0A9M2.xml Xanthine phosphoribosyltransferase P0A9M5 XGPT_ECOLI gpt http://ecmdb.ca/proteins/P0A9M5.xml Purine nucleoside phosphorylase deoD-type P0ABP8 DEOD_ECOLI deoD http://ecmdb.ca/proteins/P0ABP8.xml Non-specific ribonucleoside hydrolase rihC P22564 RIHC_ECOLI rihC http://ecmdb.ca/proteins/P22564.xml Guanine deaminase P76641 GUAD_ECOLI guaD http://ecmdb.ca/proteins/P76641.xml Putative xanthine dehydrogenase yagS FAD-binding subunit P77324 YAGS_ECOLI yagS http://ecmdb.ca/proteins/P77324.xml Putative xanthine dehydrogenase yagR molybdenum-binding subunit P77489 YAGR_ECOLI yagR http://ecmdb.ca/proteins/P77489.xml Xanthine dehydrogenase molybdenum-binding subunit Q46799 XDHA_ECOLI xdhA http://ecmdb.ca/proteins/Q46799.xml Xanthine dehydrogenase FAD-binding subunit Q46800 XDHB_ECOLI xdhB http://ecmdb.ca/proteins/Q46800.xml Xanthine dehydrogenase iron-sulfur-binding subunit Q46801 XDHC_ECOLI xdhC http://ecmdb.ca/proteins/Q46801.xml Xanthosine phosphorylase P45563 XAPA_ECOLI xapA http://ecmdb.ca/proteins/P45563.xml PaoABC aldehyde oxidoreductase, 2Fe-2S subunit P77165 paoA http://ecmdb.ca/proteins/P77165.xml Xanthine permease XanP P0AGM9 XANP_ECOLI xanP http://ecmdb.ca/proteins/P0AGM9.xml Xanthine permease XanQ P67444 XANQ_ECOLI xanQ http://ecmdb.ca/proteins/P67444.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml Water + Hypoxanthine + NAD > Hydrogen ion + NADH + Xanthine R01768 RXN-7682 Water + NAD + Xanthine <> Hydrogen ion + NADH + Uric acid R02103 RXN0-901 Water + Xanthosine > Ribose + Xanthine Phosphoribosyl pyrophosphate + Xanthine <> Pyrophosphate + Xanthylic acid R02142 XANPRIBOSYLTRAN-RXN Phosphate + Xanthosine <> Ribose-1-phosphate + Xanthine XANTHOSINEPHOSPHORY-RXN Guanine + Hydrogen ion + Water > Ammonium + Xanthine Guanine + Water <> Xanthine + Ammonia R01676 GUANINE-DEAMINASE-RXN Hypoxanthine + NAD + Water <> Xanthine + NADH + Hydrogen ion R01768 Xanthylic acid + Pyrophosphate <> Xanthine + Phosphoribosyl pyrophosphate R02142 Xanthosine + Phosphate <> Xanthine + alpha-D-Ribose 1-phosphate R02297 isoguanine + Water > Xanthine + Ammonia RXN0-6708 Water + Guanine > Ammonia + Xanthine GUANINE-DEAMINASE-RXN Xanthosine + Water > D-ribose + Xanthine RXN0-363 Xanthine + NAD + Water > Uric acid + NADH + Hydrogen ion RXN0-901 Xanthylic acid + Pyrophosphate < Xanthine + Phosphoribosyl pyrophosphate R02142 XANPRIBOSYLTRAN-RXN Xanthosine + Phosphate > Ribose-1-phosphate + Xanthine XANTHOSINEPHOSPHORY-RXN Xanthine + NAD + Water > Uric acid + NADH Hypoxanthine + NAD + Water > Xanthine + NADH Xanthylic acid + Pyrophosphate > Phosphoribosyl pyrophosphate + Xanthine Xanthine + Phosphoribosyl pyrophosphate > Xanthylic acid + Pyrophosphate PW_R006088 Guanine + Water <> Xanthine + Ammonia Water + Hypoxanthine + NAD > Hydrogen ion + NADH + Xanthine Water + Hypoxanthine + NAD > Hydrogen ion + NADH + Xanthine Water + Hypoxanthine + NAD > Hydrogen ion + NADH + Xanthine