2.02012-05-31 09:56:05 -06002015-09-13 15:15:16 -0600ECMDB00050M2MDB000016AdenosineAdenosine 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-ribofuranose1-(6-amino-9H-Purin-9-yl)-1-deoxy-b-delta-ribofuranose1-(6-amino-9H-Purin-9-yl)-1-deoxy-b-δ-ribofuranose1-(6-Amino-9H-purin-9-yl)-1-deoxy-beta-D-Ribofuranose1-(6-amino-9H-purin-9-yl)-1-deoxy-beta-delta-Ribofuranose1-(6-amino-9H-Purin-9-yl)-1-deoxy-β-D-ribofuranose1-(6-amino-9H-Purin-9-yl)-1-deoxy-β-δ-ribofuranose6-amino-9b-D-Ribofuranosyl-9H-purine6-amino-9b-delta-Ribofuranosyl-9H-purine6-amino-9b-δ-Ribofuranosyl-9H-purine6-Amino-9beta-D-ribofuranosyl-9H-purine6-Amino-9beta-delta-ribofuranosyl-9H-purine6-amino-9β-D-Ribofuranosyl-9H-purine6-amino-9β-δ-Ribofuranosyl-9H-purine9-b-D-Arabinofuranosyladenine9-b-D-Ribofuranosidoadenine9-b-D-Ribofuranosyl-9H-purin-6-amine9-b-D-Ribofuranosyladenine9-b-delta-Arabinofuranosyladenine9-b-delta-Ribofuranosidoadenine9-b-delta-Ribofuranosyl-9H-purin-6-amine9-b-delta-Ribofuranosyladenine9-b-δ-Arabinofuranosyladenine9-b-δ-Ribofuranosidoadenine9-b-δ-Ribofuranosyl-9H-purin-6-amine9-b-δ-Ribofuranosyladenine9-beta-D-Arabinofuranosyladenine9-beta-D-Ribofuranosidoadenine9-beta-D-Ribofuranosyl-9H-purin-6-amine9-beta-D-Ribofuranosyladenine9-beta-delta-Arabinofuranosyladenine9-beta-delta-Ribofuranosidoadenine9-beta-delta-Ribofuranosyl-9H-purin-6-amine9-beta-delta-Ribofuranosyladenine9-β-D-Arabinofuranosyladenine9-β-D-Ribofuranosidoadenine9-β-D-Ribofuranosyl-9H-purin-6-amine9-β-D-Ribofuranosyladenine9-β-δ-Arabinofuranosyladenine9-β-δ-Ribofuranosidoadenine9-β-δ-Ribofuranosyl-9H-purin-6-amine9-β-δ-Ribofuranosyladenine9b-D-Ribofuranosyl-9H-purin-6-amine9b-D-Ribofuranosyladenine9b-delta-Ribofuranosyl-9H-purin-6-amine9b-delta-Ribofuranosyladenine9b-δ-Ribofuranosyl-9H-purin-6-amine9b-δ-Ribofuranosyladenine9beta-D-ribofuranosyl-9H-Purin-6-amine9beta-D-Ribofuranosyladenine9beta-delta-ribofuranosyl-9H-Purin-6-amine9beta-delta-Ribofuranosyladenine9β-D-Ribofuranosyl-9H-purin-6-amine9β-D-Ribofuranosyladenine9β-δ-Ribofuranosyl-9H-purin-6-amine9β-δ-RibofuranosyladenineAdenine nucleosideAdenine ribosideAdenine-9b-D-ribofuranosideAdenine-9b-delta-ribofuranosideAdenine-9b-δ-ribofuranosideAdenine-9beta-D-RibofuranosideAdenine-9beta-delta-RibofuranosideAdenine-9β-D-ribofuranosideAdenine-9β-δ-ribofuranosideAdenine-D-riboseAdenocardAdenocorAdenoscanAdenosinb-AdenosineB-D-Adenosineb-delta-Adenosineb-δ-AdenosineBeta-AdenosineBeta-D-AdenosineBeta-delta-AdenosineBonitonMyocolNucleocardylSandesinβ-Adenosineβ-D-Adenosineβ-δ-AdenosineC10H13N5O4267.2413267.096753929(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-dioladenosine58-61-7NC1=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C2=NC=N1InChI=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/s1OIRDTQYFTABQOQ-KQYNXXCUSA-NSolidCytosolExtra-organismPeriplasmlogp-1.21logs-1.28solubility1.40e+01 g/lmelting_point235.5 oClogp-2.1pka_strongest_acidic12.45pka_strongest_basic3.92iupac(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diolaverage_mass267.2413mono_mass267.096753929smilesNC1=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C2=NC=N1formulaC10H13N5O4inchiInChI=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/s1inchikeyOIRDTQYFTABQOQ-KQYNXXCUSA-Npolar_surface_area139.54refractivity63.2polarizability25.28rotatable_bond_count2acceptor_count8donor_count4physiological_charge0formal_charge0Purine metabolismec00230Metabolic pathwayseco01100adenine and adenosine salvage IThe 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.PW002069Metabolicadenine and adenosine salvage IIThe 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 IMPPW002071Metabolicadenine and adenosine salvage IIIAdenosine 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 AMPPW002072Metabolicpurine 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.PW002091Metabolicadenine and adenosine salvage IIIPWY-6609adenine and adenosine salvage VPWY-6611purine ribonucleosides degradation to ribose-1-phosphatePWY0-1296adenine and adenosine salvage IIPWY-6605adenosine nucleotides degradation IISALVADEHYPOX-PWYSpecdb::CMs297Specdb::CMs298Specdb::CMs299Specdb::CMs300Specdb::CMs2034Specdb::CMs2087Specdb::CMs3195Specdb::CMs30173Specdb::CMs30263Specdb::CMs30473Specdb::CMs30822Specdb::CMs30969Specdb::CMs30970Specdb::CMs37266Specdb::CMs164828Specdb::CMs1048288Specdb::CMs1048290Specdb::CMs1048291Specdb::CMs1048293Specdb::CMs1048295Specdb::CMs1048297Specdb::CMs1048299Specdb::CMs1048301Specdb::CMs1048302Specdb::CMs1048304Specdb::NmrOneD1053Specdb::NmrOneD1131Specdb::NmrOneD141970Specdb::NmrOneD141971Specdb::NmrOneD141972Specdb::NmrOneD141973Specdb::NmrOneD141974Specdb::NmrOneD141975Specdb::NmrOneD141976Specdb::NmrOneD141977Specdb::NmrOneD141978Specdb::NmrOneD141979Specdb::NmrOneD141980Specdb::NmrOneD141981Specdb::NmrOneD141982Specdb::NmrOneD141983Specdb::NmrOneD141984Specdb::NmrOneD141985Specdb::NmrOneD141986Specdb::NmrOneD141987Specdb::NmrOneD141988Specdb::NmrOneD141989Specdb::NmrOneD166516Specdb::MsMs81Specdb::MsMs82Specdb::MsMs83Specdb::MsMs2654Specdb::MsMs2655Specdb::MsMs2656Specdb::MsMs2657Specdb::MsMs2658Specdb::MsMs2659Specdb::MsMs2660Specdb::MsMs2661Specdb::MsMs2662Specdb::MsMs2663Specdb::MsMs2664Specdb::MsMs2665Specdb::MsMs2666Specdb::MsMs2667Specdb::MsMs2668Specdb::MsMs2669Specdb::MsMs2674Specdb::MsMs2675Specdb::MsMs2676Specdb::MsMs2677Specdb::MsMs179655Specdb::MsMs179656Specdb::NmrTwoD943Specdb::NmrTwoD1111HMDB0005054923C0021216335ADENOSINEADNAdenosineKeseler, I. 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Huaxue Shiji (2006), 28(10), 633-634.http://hmdb.ca/system/metabolites/msds/000/000/035/original/HMDB00050.pdf?1358893299Alkaline phosphataseP00634PPB_ECOLIphoAhttp://ecmdb.ca/proteins/P00634.xmlProtein ushAP07024USHA_ECOLIushAhttp://ecmdb.ca/proteins/P07024.xml2',3'-cyclic-nucleotide 2'-phosphodiesterase/3'-nucleotidaseP08331CPDB_ECOLIcpdBhttp://ecmdb.ca/proteins/P08331.xmlMultifunctional protein surEP0A840SURE_ECOLIsurEhttp://ecmdb.ca/proteins/P0A840.xml5'-nucleotidase yjjGP0A8Y1YJJG_ECOLIyjjGhttp://ecmdb.ca/proteins/P0A8Y1.xmlPurine nucleoside phosphorylase deoD-typeP0ABP8DEOD_ECOLIdeoDhttp://ecmdb.ca/proteins/P0ABP8.xmlClass B acid phosphataseP0AE22APHA_ECOLIaphAhttp://ecmdb.ca/proteins/P0AE22.xmlRiboflavin synthase alpha chainP0AFU8RISA_ECOLIribEhttp://ecmdb.ca/proteins/P0AFU8.xmlAdenosine deaminaseP22333ADD_ECOLIaddhttp://ecmdb.ca/proteins/P22333.xmlNon-specific ribonucleoside hydrolase rihCP22564RIHC_ECOLIrihChttp://ecmdb.ca/proteins/P22564.xmlPyrimidine-specific ribonucleoside hydrolase rihBP33022RIHB_ECOLIrihBhttp://ecmdb.ca/proteins/P33022.xmlAdenylate kinaseP69441KAD_ECOLIadkhttp://ecmdb.ca/proteins/P69441.xml5'-nucleotidase yfbRP76491YFBR_ECOLIyfbRhttp://ecmdb.ca/proteins/P76491.xmltRNA-specific adenosine deaminaseP68398TADA_ECOLItadAhttp://ecmdb.ca/proteins/P68398.xmlXanthosine permeaseP45562XAPB_ECOLIxapBhttp://ecmdb.ca/proteins/P45562.xmlNucleoside permease nupCP0AFF2NUPC_ECOLInupChttp://ecmdb.ca/proteins/P0AFF2.xmlNucleoside permease nupGP0AFF4NUPG_ECOLInupGhttp://ecmdb.ca/proteins/P0AFF4.xmlNucleoside permease nupXP33021NUPX_ECOLInupXhttp://ecmdb.ca/proteins/P33021.xmlNucleoside-specific channel-forming protein tsxP0A927TSX_ECOLItsxhttp://ecmdb.ca/proteins/P0A927.xmlAdenosine monophosphate + Water > Adenosine + PhosphateAdenosine + Water > Adenine + RiboseR01245Adenosine + Adenosine triphosphate > ADP + Adenosine monophosphate + Hydrogen ionAdenosine + Hydrogen ion + Water > Inosine + Ammonium3'-AMP + Water > Adenosine + PhosphateAdenosine + Phosphate <> Adenine + Ribose-1-phosphateADENPHOSPHOR-RXNAdenosine monophosphate + Water <> Adenosine + PhosphateR00183Adenosine + Water <> Adenine + RiboseR01245Adenosine + Water <> Inosine + AmmoniaR01560Adenosine + Phosphate <> Adenine + alpha-D-Ribose 1-phosphateR01561Water + Adenosine > Ammonia + InosineR01560ADENODEAMIN-RXNAdenosine + Water > D-ribose + AdenineADENOSINE-NUCLEOSIDASE-RXNAdenosine monophosphate + Water > Adenosine + PhosphateAMP-DEPHOSPHORYLATION-RXNAdenosine + Water > beta-D-ribofuranose + AdeninePW_R006054Adenine + Ribose-1-phosphate > Phosphate + AdenosinePW_R006047Adenosine + Phosphate > Adenine + Ribose-1-phosphatePW_R006066Water + Adenosine > Ammonia + InosineGutnick 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 glucoseShake flask and filter culture0.13uM0.037 oCK12 NCM3722Mid-Log Phase5200Bennett, 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 5:593-599.1956162148 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 GlucoBioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h62.2uM0.037 oCBW25113Stationary Phase, glucose limited2488000Ishii, 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