2.0 2012-05-31 10:23:32 -0600 2015-09-13 12:56:06 -0600 ECMDB00195 M2MDB000082 Inosine Inosine 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) (-)-Inosine 1,9-Dihydro-9-b-D-ribofuranosyl-6H-Purin-6-one 1,9-dihydro-9-b-delta-Ribofuranosyl-6H-purin-6-one 1,9-dihydro-9-b-δ-Ribofuranosyl-6H-purin-6-one 1,9-Dihydro-9-beta-D-ribofuranosyl-6H-purin-6-one 1,9-Dihydro-9-beta-delta-ribofuranosyl-6H-purin-6-one 1,9-dihydro-9-β-D-Ribofuranosyl-6H-purin-6-one 1,9-dihydro-9-β-δ-Ribofuranosyl-6H-purin-6-one 9-b-D-Ribofuranosyl-Hypoxanthine 9-b-D-Ribofuranosylhypoxanthine 9-b-delta-Ribofuranosyl-hypoxanthine 9-b-delta-Ribofuranosylhypoxanthine 9-b-δ-Ribofuranosyl-hypoxanthine 9-b-δ-Ribofuranosylhypoxanthine 9-beta-D-Ribofuranosyl-Hypoxanthine 9-beta-D-Ribofuranosylhypoxanthine 9-beta-delta-Ribofuranosyl-Hypoxanthine 9-beta-delta-Ribofuranosylhypoxanthine 9-β-D-Ribofuranosyl-hypoxanthine 9-β-D-Ribofuranosylhypoxanthine 9-β-δ-Ribofuranosyl-hypoxanthine 9-β-δ-Ribofuranosylhypoxanthine 9b-D-Ribofuranosylhypoxanthine 9b-delta-Ribofuranosylhypoxanthine 9b-δ-Ribofuranosylhypoxanthine 9beta-D-Ribofuranosylhypoxanthine 9beta-delta-Ribofuranosylhypoxanthine 9β-D-Ribofuranosylhypoxanthine 9β-δ-Ribofuranosylhypoxanthine Atorel b-D-Ribofuranoside hypoxanthine-9 b-delta-Ribofuranoside hypoxanthine-9 b-Inosine b-δ-Ribofuranoside hypoxanthine-9 Beta-D-Ribofuranoside hypoxanthine-9 Beta-delta-Ribofuranoside hypoxanthine-9 Beta-Inosine HXR Hypoxanthine 9-b-D-ribofuranoside Hypoxanthine 9-b-delta-ribofuranoside Hypoxanthine 9-b-δ-ribofuranoside Hypoxanthine 9-beta-D-ribofuranoside Hypoxanthine 9-beta-delta-ribofuranoside Hypoxanthine 9-β-D-ribofuranoside Hypoxanthine 9-β-δ-ribofuranoside Hypoxanthine D-riboside Hypoxanthine nucleoside Hypoxanthine ribonucleoside Hypoxanthine riboside Hypoxanthine-9 b-D-ribofuranoside Hypoxanthine-9 b-delta-ribofuranoside Hypoxanthine-9 b-δ-ribofuranoside Hypoxanthine-9 beta-D-Ribofuranoside Hypoxanthine-9 beta-delta-Ribofuranoside Hypoxanthine-9 β-D-ribofuranoside Hypoxanthine-9 β-δ-ribofuranoside Hypoxanthine-9-b-D-ribofuranoside Hypoxanthine-9-b-delta-ribofuranoside Hypoxanthine-9-b-δ-ribofuranoside Hypoxanthine-9-beta-D-ribofuranoside Hypoxanthine-9-beta-delta-ribofuranoside Hypoxanthine-9-D-ribofuranoside Hypoxanthine-9-delta-ribofuranoside Hypoxanthine-9-β-D-ribofuranoside Hypoxanthine-9-β-δ-ribofuranoside Hypoxanthine-9-δ-ribofuranoside Hypoxanthine-ribose Hypoxanthosine Indole-3-carboxaldehyde Ino Inosie Iso-prinosine Oxiamin Panholic-L Pantholic-L Ribonosine Riboxine Selfer Trophicardyl β-D-Ribofuranoside hypoxanthine-9 β-Inosine β-δ-Ribofuranoside hypoxanthine-9 C10H12N4O5 268.2261 268.080769514 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-3H-purin-6-one inosine 58-63-9 OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1NC=NC2=O InChI=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/s1 UGQMRVRMYYASKQ-KQYNXXCUSA-N Solid Cytosol Extra-organism Periplasm melting_point 218 oC logp -2 ChemAxon pka_strongest_acidic 6.94 ChemAxon pka_strongest_basic 2.74 ChemAxon iupac 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-3H-purin-6-one ChemAxon average_mass 268.2261 ChemAxon mono_mass 268.080769514 ChemAxon smiles OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1NC=NC2=O ChemAxon formula C10H12N4O5 ChemAxon inchi InChI=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/s1 ChemAxon inchikey UGQMRVRMYYASKQ-KQYNXXCUSA-N ChemAxon polar_surface_area 129.2 ChemAxon refractivity 60.9 ChemAxon polarizability 24.6 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 8 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Purine metabolism ec00230 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 adenine and adenosine salvage II 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 can then be phosphorylated through an ATP driven inosine kinase resulting in the release of an ADP, a hydrogen ion and a IMP PW002071 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 adenine and adenosine salvage V PWY-6611 purine ribonucleosides degradation to ribose-1-phosphate PWY0-1296 adenosine nucleotides degradation II SALVADEHYPOX-PWY Specdb::CMs 448 Specdb::CMs 449 Specdb::CMs 2029 Specdb::CMs 22590 Specdb::CMs 30576 Specdb::CMs 30880 Specdb::CMs 31063 Specdb::CMs 37351 Specdb::CMs 163703 Specdb::CMs 1053958 Specdb::CMs 1053960 Specdb::CMs 1053962 Specdb::CMs 1053964 Specdb::CMs 1053965 Specdb::CMs 1053967 Specdb::CMs 1053969 Specdb::CMs 1053971 Specdb::CMs 1053973 Specdb::CMs 1053975 Specdb::CMs 1053977 Specdb::CMs 1053979 Specdb::CMs 1053981 Specdb::CMs 1053983 Specdb::CMs 1053985 Specdb::CMs 1053986 Specdb::NmrOneD 1174 Specdb::NmrOneD 4906 Specdb::NmrOneD 142810 Specdb::NmrOneD 142811 Specdb::NmrOneD 142812 Specdb::NmrOneD 142813 Specdb::NmrOneD 142814 Specdb::NmrOneD 142815 Specdb::NmrOneD 142816 Specdb::NmrOneD 142817 Specdb::NmrOneD 142818 Specdb::NmrOneD 142819 Specdb::NmrOneD 142820 Specdb::NmrOneD 142821 Specdb::NmrOneD 142822 Specdb::NmrOneD 142823 Specdb::NmrOneD 142824 Specdb::NmrOneD 142825 Specdb::NmrOneD 142826 Specdb::NmrOneD 142827 Specdb::NmrOneD 142828 Specdb::NmrOneD 142829 Specdb::MsMs 316 Specdb::MsMs 317 Specdb::MsMs 318 Specdb::MsMs 3543 Specdb::MsMs 3544 Specdb::MsMs 3545 Specdb::MsMs 3546 Specdb::MsMs 3547 Specdb::MsMs 3548 Specdb::MsMs 3549 Specdb::MsMs 3550 Specdb::MsMs 3551 Specdb::MsMs 3552 Specdb::MsMs 3553 Specdb::MsMs 3554 Specdb::MsMs 3555 Specdb::MsMs 3556 Specdb::MsMs 3557 Specdb::MsMs 3558 Specdb::MsMs 3559 Specdb::MsMs 3560 Specdb::MsMs 3561 Specdb::MsMs 3562 Specdb::MsMs 3563 Specdb::MsMs 3566 Specdb::NmrTwoD 992 Specdb::NmrTwoD 1200 HMDB00195 6021 5799 C00294 17596 INOSINE NOS Inosine Keseler, I. 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Faming Zhuanli Shenqing Gongkai Shuomingshu (2003), 6 pp. http://hmdb.ca/system/metabolites/msds/000/000/138/original/HMDB00195.pdf?1358894588 Protein ushA P07024 USHA_ECOLI ushA http://ecmdb.ca/proteins/P07024.xml Multifunctional protein surE P0A840 SURE_ECOLI surE http://ecmdb.ca/proteins/P0A840.xml 5'-nucleotidase yjjG P0A8Y1 YJJG_ECOLI yjjG http://ecmdb.ca/proteins/P0A8Y1.xml Purine nucleoside phosphorylase deoD-type P0ABP8 DEOD_ECOLI deoD http://ecmdb.ca/proteins/P0ABP8.xml Class B acid phosphatase P0AE22 APHA_ECOLI aphA http://ecmdb.ca/proteins/P0AE22.xml Inosine-guanosine kinase P0AEW6 INGK_ECOLI gsk http://ecmdb.ca/proteins/P0AEW6.xml Adenosine deaminase P22333 ADD_ECOLI add http://ecmdb.ca/proteins/P22333.xml Non-specific ribonucleoside hydrolase rihC P22564 RIHC_ECOLI rihC http://ecmdb.ca/proteins/P22564.xml Pyrimidine-specific ribonucleoside hydrolase rihB P33022 RIHB_ECOLI rihB http://ecmdb.ca/proteins/P33022.xml 5'-nucleotidase yfbR P76491 YFBR_ECOLI yfbR http://ecmdb.ca/proteins/P76491.xml Xanthosine phosphorylase P45563 XAPA_ECOLI xapA http://ecmdb.ca/proteins/P45563.xml tRNA-specific adenosine deaminase P68398 TADA_ECOLI tadA http://ecmdb.ca/proteins/P68398.xml Xanthosine permease P45562 XAPB_ECOLI xapB http://ecmdb.ca/proteins/P45562.xml Nucleoside permease nupC P0AFF2 NUPC_ECOLI nupC http://ecmdb.ca/proteins/P0AFF2.xml Nucleoside permease nupG P0AFF4 NUPG_ECOLI nupG http://ecmdb.ca/proteins/P0AFF4.xml Nucleoside-specific channel-forming protein tsx P0A927 TSX_ECOLI tsx http://ecmdb.ca/proteins/P0A927.xml Water + Inosinic acid > Inosine + Phosphate Inosine + Phosphate <> Hypoxanthine + Ribose-1-phosphate INOPHOSPHOR-RXN Water + Inosine > Hypoxanthine + Ribose R01770 Adenosine triphosphate + Inosine <> ADP + Hydrogen ion + Inosinic acid R01131 INOSINEKIN-RXN Adenosine + Hydrogen ion + Water > Inosine + Ammonium Inosinic acid + Water <> Inosine + Phosphate R01126 Adenosine triphosphate + Inosine <> ADP + Inosinic acid R01131 Adenosine + Water <> Inosine + Ammonia R01560 Inosine + Water <> Hypoxanthine + Ribose R01770 Inosine + Phosphate <> Hypoxanthine + alpha-D-Ribose 1-phosphate R01863 Water + Adenosine > Ammonia + Inosine R01560 ADENODEAMIN-RXN Inosine + Water > D-ribose + Hypoxanthine INOSINE-NUCLEOSIDASE-RXN Inosine + Adenosine triphosphate > Hydrogen ion + Inosinic acid + ADP INOSINEKIN-RXN Adenosine triphosphate + Inosine > ADP + Inosinic acid Inosine + Phosphate > Ribose-1-phosphate + Hypoxanthine PW_R006050 Water + Adenosine > Ammonia + Inosine 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 31.1 uM 0.0 37 oC BW25113 Stationary Phase, glucose limited 124400 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