2.0 2012-05-31 09:56:05 -0600 2015-09-13 15:15:16 -0600 ECMDB00050 M2MDB000016 Adenosine Adenosine is nucleoside that is composed of adenine and d-ribose. Adenosine or adenosine derivatives play many important biological roles in addition to being components of DNA and RNA. Adenosine itself is a neurotransmitter. 1-(6-amino-9H-Purin-9-yl)-1-deoxy-b-D-ribofuranose 1-(6-amino-9H-Purin-9-yl)-1-deoxy-b-delta-ribofuranose 1-(6-amino-9H-Purin-9-yl)-1-deoxy-b-δ-ribofuranose 1-(6-Amino-9H-purin-9-yl)-1-deoxy-beta-D-Ribofuranose 1-(6-amino-9H-purin-9-yl)-1-deoxy-beta-delta-Ribofuranose 1-(6-amino-9H-Purin-9-yl)-1-deoxy-β-D-ribofuranose 1-(6-amino-9H-Purin-9-yl)-1-deoxy-β-δ-ribofuranose 6-amino-9b-D-Ribofuranosyl-9H-purine 6-amino-9b-delta-Ribofuranosyl-9H-purine 6-amino-9b-δ-Ribofuranosyl-9H-purine 6-Amino-9beta-D-ribofuranosyl-9H-purine 6-Amino-9beta-delta-ribofuranosyl-9H-purine 6-amino-9β-D-Ribofuranosyl-9H-purine 6-amino-9β-δ-Ribofuranosyl-9H-purine 9-b-D-Arabinofuranosyladenine 9-b-D-Ribofuranosidoadenine 9-b-D-Ribofuranosyl-9H-purin-6-amine 9-b-D-Ribofuranosyladenine 9-b-delta-Arabinofuranosyladenine 9-b-delta-Ribofuranosidoadenine 9-b-delta-Ribofuranosyl-9H-purin-6-amine 9-b-delta-Ribofuranosyladenine 9-b-δ-Arabinofuranosyladenine 9-b-δ-Ribofuranosidoadenine 9-b-δ-Ribofuranosyl-9H-purin-6-amine 9-b-δ-Ribofuranosyladenine 9-beta-D-Arabinofuranosyladenine 9-beta-D-Ribofuranosidoadenine 9-beta-D-Ribofuranosyl-9H-purin-6-amine 9-beta-D-Ribofuranosyladenine 9-beta-delta-Arabinofuranosyladenine 9-beta-delta-Ribofuranosidoadenine 9-beta-delta-Ribofuranosyl-9H-purin-6-amine 9-beta-delta-Ribofuranosyladenine 9-β-D-Arabinofuranosyladenine 9-β-D-Ribofuranosidoadenine 9-β-D-Ribofuranosyl-9H-purin-6-amine 9-β-D-Ribofuranosyladenine 9-β-δ-Arabinofuranosyladenine 9-β-δ-Ribofuranosidoadenine 9-β-δ-Ribofuranosyl-9H-purin-6-amine 9-β-δ-Ribofuranosyladenine 9b-D-Ribofuranosyl-9H-purin-6-amine 9b-D-Ribofuranosyladenine 9b-delta-Ribofuranosyl-9H-purin-6-amine 9b-delta-Ribofuranosyladenine 9b-δ-Ribofuranosyl-9H-purin-6-amine 9b-δ-Ribofuranosyladenine 9beta-D-ribofuranosyl-9H-Purin-6-amine 9beta-D-Ribofuranosyladenine 9beta-delta-ribofuranosyl-9H-Purin-6-amine 9beta-delta-Ribofuranosyladenine 9β-D-Ribofuranosyl-9H-purin-6-amine 9β-D-Ribofuranosyladenine 9β-δ-Ribofuranosyl-9H-purin-6-amine 9β-δ-Ribofuranosyladenine Adenine nucleoside Adenine riboside Adenine-9b-D-ribofuranoside Adenine-9b-delta-ribofuranoside Adenine-9b-δ-ribofuranoside Adenine-9beta-D-Ribofuranoside Adenine-9beta-delta-Ribofuranoside Adenine-9β-D-ribofuranoside Adenine-9β-δ-ribofuranoside Adenine-D-ribose Adenocard Adenocor Adenoscan Adenosin b-Adenosine B-D-Adenosine b-delta-Adenosine b-δ-Adenosine Beta-Adenosine Beta-D-Adenosine Beta-delta-Adenosine Boniton Myocol Nucleocardyl Sandesin β-Adenosine β-D-Adenosine β-δ-Adenosine C10H13N5O4 267.2413 267.096753929 (2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol adenosine 58-61-7 NC1=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C2=NC=N1 InChI=1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7-,10-/m1/s1 OIRDTQYFTABQOQ-KQYNXXCUSA-N Solid Cytosol Extra-organism Periplasm logp -1.21 ALOGPS logs -1.28 ALOGPS solubility 1.40e+01 g/l ALOGPS melting_point 235.5 oC logp -2.1 ChemAxon pka_strongest_acidic 12.45 ChemAxon pka_strongest_basic 3.92 ChemAxon iupac (2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol ChemAxon average_mass 267.2413 ChemAxon mono_mass 267.096753929 ChemAxon smiles NC1=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C2=NC=N1 ChemAxon formula C10H13N5O4 ChemAxon inchi InChI=1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7-,10-/m1/s1 ChemAxon inchikey OIRDTQYFTABQOQ-KQYNXXCUSA-N ChemAxon polar_surface_area 139.54 ChemAxon refractivity 63.2 ChemAxon polarizability 25.28 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 adenine and adenosine salvage III Adenosine is first incorporated into the cytosol through either a nupG or a nupC transporter. Once in the cytosol, adenosine is degraded into adenine by reacting with a water and a adenosine nucleosidase, releasing a D-ribofuranose and a adenine. The adenine then reacts with a PRPP through a adenine phosphoribosyltransferase resulting in the release of a pyrophosphate and an AMP PW002072 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 adenine and adenosine salvage II PWY-6605 adenosine nucleotides degradation II SALVADEHYPOX-PWY Specdb::CMs 297 Specdb::CMs 298 Specdb::CMs 299 Specdb::CMs 300 Specdb::CMs 2034 Specdb::CMs 2087 Specdb::CMs 3195 Specdb::CMs 30173 Specdb::CMs 30263 Specdb::CMs 30473 Specdb::CMs 30822 Specdb::CMs 30969 Specdb::CMs 30970 Specdb::CMs 37266 Specdb::CMs 164828 Specdb::CMs 1048288 Specdb::CMs 1048290 Specdb::CMs 1048291 Specdb::CMs 1048293 Specdb::CMs 1048295 Specdb::CMs 1048297 Specdb::CMs 1048299 Specdb::CMs 1048301 Specdb::CMs 1048302 Specdb::CMs 1048304 Specdb::NmrOneD 1053 Specdb::NmrOneD 1131 Specdb::NmrOneD 141970 Specdb::NmrOneD 141971 Specdb::NmrOneD 141972 Specdb::NmrOneD 141973 Specdb::NmrOneD 141974 Specdb::NmrOneD 141975 Specdb::NmrOneD 141976 Specdb::NmrOneD 141977 Specdb::NmrOneD 141978 Specdb::NmrOneD 141979 Specdb::NmrOneD 141980 Specdb::NmrOneD 141981 Specdb::NmrOneD 141982 Specdb::NmrOneD 141983 Specdb::NmrOneD 141984 Specdb::NmrOneD 141985 Specdb::NmrOneD 141986 Specdb::NmrOneD 141987 Specdb::NmrOneD 141988 Specdb::NmrOneD 141989 Specdb::NmrOneD 166516 Specdb::MsMs 81 Specdb::MsMs 82 Specdb::MsMs 83 Specdb::MsMs 2654 Specdb::MsMs 2655 Specdb::MsMs 2656 Specdb::MsMs 2657 Specdb::MsMs 2658 Specdb::MsMs 2659 Specdb::MsMs 2660 Specdb::MsMs 2661 Specdb::MsMs 2662 Specdb::MsMs 2663 Specdb::MsMs 2664 Specdb::MsMs 2665 Specdb::MsMs 2666 Specdb::MsMs 2667 Specdb::MsMs 2668 Specdb::MsMs 2669 Specdb::MsMs 2674 Specdb::MsMs 2675 Specdb::MsMs 2676 Specdb::MsMs 2677 Specdb::MsMs 179655 Specdb::MsMs 179656 Specdb::NmrTwoD 943 Specdb::NmrTwoD 1111 HMDB00050 54923 C00212 16335 ADENOSINE ADN Adenosine Keseler, I. 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Synthesis of adenosine from inosine. Huaxue Shiji (2006), 28(10), 633-634. http://hmdb.ca/system/metabolites/msds/000/000/035/original/HMDB00050.pdf?1358893299 Alkaline phosphatase P00634 PPB_ECOLI phoA http://ecmdb.ca/proteins/P00634.xml Protein ushA P07024 USHA_ECOLI ushA http://ecmdb.ca/proteins/P07024.xml 2',3'-cyclic-nucleotide 2'-phosphodiesterase/3'-nucleotidase P08331 CPDB_ECOLI cpdB http://ecmdb.ca/proteins/P08331.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 Riboflavin synthase alpha chain P0AFU8 RISA_ECOLI ribE http://ecmdb.ca/proteins/P0AFU8.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 Adenylate kinase P69441 KAD_ECOLI adk http://ecmdb.ca/proteins/P69441.xml 5'-nucleotidase yfbR P76491 YFBR_ECOLI yfbR http://ecmdb.ca/proteins/P76491.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 permease nupX P33021 NUPX_ECOLI nupX http://ecmdb.ca/proteins/P33021.xml Nucleoside-specific channel-forming protein tsx P0A927 TSX_ECOLI tsx http://ecmdb.ca/proteins/P0A927.xml Adenosine monophosphate + Water > Adenosine + Phosphate Adenosine + Water > Adenine + Ribose R01245 Adenosine + Adenosine triphosphate > ADP + Adenosine monophosphate + Hydrogen ion Adenosine + Hydrogen ion + Water > Inosine + Ammonium 3'-AMP + Water > Adenosine + Phosphate Adenosine + Phosphate <> Adenine + Ribose-1-phosphate ADENPHOSPHOR-RXN Adenosine monophosphate + Water <> Adenosine + Phosphate R00183 Adenosine + Water <> Adenine + Ribose R01245 Adenosine + Water <> Inosine + Ammonia R01560 Adenosine + Phosphate <> Adenine + alpha-D-Ribose 1-phosphate R01561 Water + Adenosine > Ammonia + Inosine R01560 ADENODEAMIN-RXN Adenosine + Water > D-ribose + Adenine ADENOSINE-NUCLEOSIDASE-RXN Adenosine monophosphate + Water > Adenosine + Phosphate AMP-DEPHOSPHORYLATION-RXN Adenosine + Water > beta-D-ribofuranose + Adenine PW_R006054 Adenine + Ribose-1-phosphate > Phosphate + Adenosine PW_R006047 Adenosine + Phosphate > Adenine + Ribose-1-phosphate PW_R006066 Water + Adenosine > Ammonia + Inosine Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucose Shake flask and filter culture 0.13 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 520 0 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. 19561621 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 62.2 uM 0.0 37 oC BW25113 Stationary Phase, glucose limited 248800 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