2.0 2012-05-31 10:22:08 -0600 2015-06-03 15:53:19 -0600 ECMDB00157 M2MDB000059 Hypoxanthine Hypoxanthine is a naturally occurring purine derivative and a reaction intermediate in the metabolism of adenosine and in the formation of nucleic acids by the salvage pathway. Hypoxanthine is also a spontaneous deamination product of adenine. 1,7-Dihydro-6H-purin-6-one 1,7-Dihydro-6H-purine-6-one 1H,7H-Hypoxanthine 3H-Purin-6-ol 4-Hydroxy-1H-purine 6(1H)-Purinone 6-Hydroxy-1H-purine 6-Hydroxypurine 6-Oxopurine 7H-Purin-6-ol 9H-Purin-6(1H)-one 9H-Purin-6-ol Hypoxanthine enol Purin-6(1H)-one Purin-6(3H)-one Purin-6-ol Purine-6-ol Sarcine Sarkin Sarkine C5H4N4O 136.1115 136.03851077 7H-purin-6-ol 6-hydroxypurine 68-94-0 OC1=NC=NC2=C1NC=N2 InChI=1S/C5H4N4O/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10) FDGQSTZJBFJUBT-UHFFFAOYSA-N Solid Cytosol Extra-organism Periplasm logp -0.55 ALOGPS logs -1.02 ALOGPS solubility 1.30e+01 g/l ALOGPS melting_point 150 oC logp -0.048 ChemAxon pka_strongest_acidic 8.72 ChemAxon pka_strongest_basic 1.73 ChemAxon iupac 7H-purin-6-ol ChemAxon average_mass 136.1115 ChemAxon mono_mass 136.03851077 ChemAxon smiles OC1=NC=NC2=C1NC=N2 ChemAxon formula C5H4N4O ChemAxon inchi InChI=1S/C5H4N4O/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10) ChemAxon inchikey FDGQSTZJBFJUBT-UHFFFAOYSA-N ChemAxon polar_surface_area 74.69 ChemAxon refractivity 35.5 ChemAxon polarizability 11.82 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Purine metabolism ec00230 Drug metabolism - other enzymes ec00983 Metabolic pathways eco01100 adenine and adenosine salvage I The 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. PW002069 Metabolic purine deoxyribonucleosides degradation PW002077 Metabolic 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 adenine and adenosine salvage III PWY-6609 purine ribonucleosides degradation to ribose-1-phosphate PWY0-1296 purine deoxyribonucleosides degradation PWY0-1297 adenosine nucleotides degradation II SALVADEHYPOX-PWY Specdb::CMs 380 Specdb::CMs 381 Specdb::CMs 382 Specdb::CMs 1487 Specdb::CMs 2948 Specdb::CMs 29560 Specdb::CMs 30193 Specdb::CMs 30574 Specdb::CMs 30876 Specdb::CMs 31029 Specdb::CMs 31967 Specdb::CMs 31968 Specdb::CMs 37327 Specdb::CMs 169563 Specdb::CMs 1051726 Specdb::CMs 1051727 Specdb::CMs 1051729 Specdb::EiMs 325 Specdb::NmrOneD 1116 Specdb::NmrOneD 2582 Specdb::NmrOneD 3276 Specdb::NmrOneD 4910 Specdb::NmrOneD 4911 Specdb::NmrOneD 5892 Specdb::NmrOneD 5893 Specdb::NmrOneD 5894 Specdb::NmrOneD 5895 Specdb::NmrOneD 5896 Specdb::NmrOneD 5897 Specdb::NmrOneD 5898 Specdb::NmrOneD 5899 Specdb::NmrOneD 5900 Specdb::NmrOneD 5901 Specdb::NmrOneD 5902 Specdb::NmrOneD 5903 Specdb::NmrOneD 5904 Specdb::NmrOneD 5905 Specdb::NmrOneD 5906 Specdb::NmrOneD 5907 Specdb::NmrOneD 5908 Specdb::NmrOneD 5909 Specdb::NmrOneD 5910 Specdb::NmrOneD 5911 Specdb::MsMs 242 Specdb::MsMs 243 Specdb::MsMs 244 Specdb::MsMs 3130 Specdb::MsMs 3131 Specdb::MsMs 3132 Specdb::MsMs 3133 Specdb::MsMs 3134 Specdb::MsMs 3135 Specdb::MsMs 3136 Specdb::MsMs 3137 Specdb::MsMs 3138 Specdb::MsMs 3139 Specdb::MsMs 3140 Specdb::MsMs 3141 Specdb::MsMs 3142 Specdb::MsMs 3143 Specdb::MsMs 3144 Specdb::MsMs 3145 Specdb::MsMs 3146 Specdb::MsMs 3147 Specdb::MsMs 3148 Specdb::MsMs 3149 Specdb::MsMs 3150 Specdb::MsMs 3151 Specdb::NmrTwoD 973 Specdb::NmrTwoD 1175 HMDB00157 790 768 C00262 17368 HYPOXANTHINE HPA Hypoxanthine Keseler, I. 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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 Adenine deaminase P31441 ADEC_ECOLI ade http://ecmdb.ca/proteins/P31441.xml Pyrimidine-specific ribonucleoside hydrolase rihB P33022 RIHB_ECOLI rihB http://ecmdb.ca/proteins/P33022.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 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 Hypoxanthine + Phosphoribosyl pyrophosphate <> Inosinic acid + Pyrophosphate R01132 HYPOXANPRIBOSYLTRAN-RXN Deoxyinosine + Phosphate <> Deoxyribose 1-phosphate + Hypoxanthine R02748 Inosine + Phosphate <> Hypoxanthine + Ribose-1-phosphate INOPHOSPHOR-RXN Water + Hypoxanthine + NAD > Hydrogen ion + NADH + Xanthine R01768 RXN-7682 Water + Inosine > Hypoxanthine + Ribose R01770 Adenine + Hydrogen ion + Water > Hypoxanthine + Ammonium Inosinic acid + Pyrophosphate <> Hypoxanthine + Phosphoribosyl pyrophosphate R01132 Adenine + Water <> Hypoxanthine + Ammonia R01244 Hypoxanthine + NAD + Water <> Xanthine + NADH + Hydrogen ion R01768 Inosine + Water <> Hypoxanthine + Ribose R01770 Inosine + Phosphate <> Hypoxanthine + alpha-D-Ribose 1-phosphate R01863 Water + Adenine > Ammonia + Hypoxanthine R01244 ADENINE-DEAMINASE-RXN Deoxyinosine + Phosphate <> deoxyribose-1-phosphate + Hypoxanthine DEOXYINOPHOSPHOR-RXN Pyrophosphate + Inosinic acid < Phosphoribosyl pyrophosphate + Hypoxanthine HYPOXANPRIBOSYLTRAN-RXN Inosine + Water > D-ribose + Hypoxanthine INOSINE-NUCLEOSIDASE-RXN Inosinic acid + Pyrophosphate > Hypoxanthine + Phosphoribosyl pyrophosphate Hypoxanthine + NAD + Water > Xanthine + NADH Inosine + Phosphate > Ribose-1-phosphate + Hypoxanthine PW_R006050 Hypoxanthine + Phosphoribosyl pyrophosphate > Inosinic acid + Pyrophosphate PW_R006052 Water + Hypoxanthine + NAD > Hydrogen ion + NADH + Xanthine Water + Hypoxanthine + NAD > Hydrogen ion + NADH + Xanthine Water + Hypoxanthine + NAD > Hydrogen ion + NADH + Xanthine 48 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 Gluco Bioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h 277.0 uM 0.0 37 oC BW25113 Stationary Phase, glucose limited 1108000 0 Ishii, 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