2.0 2012-05-31 09:57:24 -0600 2015-09-13 15:15:17 -0600 ECMDB00101 M2MDB000039 Deoxyadenosine Deoxyadenosine is a member of the chemical class known as Purine 2'-deoxyribonucleosides and Analogues. These are compounds consisting of a purine linked to a ribose which lacks an hydroxyl group at position 2. Deoxyadenosine is a deoxyribonucleoside. It is a derivative of the nucleoside adenosine, differing from the latter by the replacement of a hydroxyl group (-OH) by hydrogen (-H) at the 2' position of its ribose sugar moiety. Deoxyadenosine is the DNA nucleoside A, which pairs with deoxythymidine (T) in double-stranded DNA. 1-(6-Amino-9H-purin-9-yl)-1,2-dideoxy-b-D-Ribofuranose 1-(6-amino-9H-Purin-9-yl)-1,2-dideoxy-b-delta-ribofuranose 1-(6-amino-9H-Purin-9-yl)-1,2-dideoxy-b-δ-ribofuranose 1-(6-amino-9H-purin-9-yl)-1,2-dideoxy-beta-D-Ribofuranose 1-(6-amino-9H-purin-9-yl)-1,2-dideoxy-beta-delta-Ribofuranose 1-(6-amino-9H-Purin-9-yl)-1,2-dideoxy-β-D-ribofuranose 1-(6-amino-9H-Purin-9-yl)-1,2-dideoxy-β-δ-ribofuranose 2'-Deoxyadenosine 2-Deoxy-adenosine 2-Deoxyadenosine 9-(2-Deoxy-b-D-erythro-pentofuranosyl)-9H-Purin-6-amine 9-(2-Deoxy-b-D-erythro-pentofuranosyl)adenine 9-(2-Deoxy-b-D-ribofuranosyl)-9H-Purin-6-amine 9-(2-Deoxy-b-delta-erythro-pentofuranosyl)-9H-purin-6-amine 9-(2-Deoxy-b-delta-erythro-pentofuranosyl)adenine 9-(2-Deoxy-b-delta-ribofuranosyl)-9H-purin-6-amine 9-(2-Deoxy-b-δ-erythro-pentofuranosyl)-9H-purin-6-amine 9-(2-Deoxy-b-δ-erythro-pentofuranosyl)adenine 9-(2-Deoxy-b-δ-ribofuranosyl)-9H-purin-6-amine 9-(2-deoxy-beta-D-erythro-pentofuranosyl)-9H-Purin-6-amine 9-(2-Deoxy-beta-D-erythro-pentofuranosyl)adenine 9-(2-deoxy-beta-D-ribofuranosyl)-9H-Purin-6-amine 9-(2-deoxy-beta-delta-erythro-pentofuranosyl)-9H-Purin-6-amine 9-(2-Deoxy-beta-delta-erythro-pentofuranosyl)adenine 9-(2-deoxy-beta-delta-ribofuranosyl)-9H-Purin-6-amine 9-(2-Deoxy-β-D-erythro-pentofuranosyl)-9H-purin-6-amine 9-(2-Deoxy-β-D-erythro-pentofuranosyl)adenine 9-(2-Deoxy-β-D-ribofuranosyl)-9H-purin-6-amine 9-(2-Deoxy-β-δ-erythro-pentofuranosyl)-9H-purin-6-amine 9-(2-Deoxy-β-δ-erythro-pentofuranosyl)adenine 9-(2-Deoxy-β-δ-ribofuranosyl)-9H-purin-6-amine Adenine deoxyribonucleoside Adenine deoxyribose Adenine-9 2-deoxy-b-D-erythro-Pentofuranoside Adenine-9 2-deoxy-b-delta-erythro-pentofuranoside Adenine-9 2-deoxy-b-δ-erythro-pentofuranoside Adenine-9 2-deoxy-beta-D-erythro-Pentofuranoside Adenine-9 2-deoxy-beta-delta-erythro-Pentofuranoside Adenine-9 2-deoxy-β-D-erythro-pentofuranoside Adenine-9 2-deoxy-β-δ-erythro-pentofuranoside Adenyldeoxyriboside DA DAdenosine Deoxyadenosine Desoxyadenosine C10H13N5O3 251.2419 251.101839307 (2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)oxolan-3-ol 2-deoxyadenosine 958-09-8 NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](CO)O1 InChI=1S/C10H13N5O3/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(17)6(2-16)18-7/h3-7,16-17H,1-2H2,(H2,11,12,13)/t5-,6+,7+/m0/s1 OLXZPDWKRNYJJZ-RRKCRQDMSA-N Solid Cytosol Extra-organism Periplasm logp -0.95 ALOGPS logs -1.37 ALOGPS solubility 1.07e+01 g/l ALOGPS melting_point 189 logp -1.2 ChemAxon pka_strongest_acidic 13.89 ChemAxon pka_strongest_basic 3.94 ChemAxon iupac (2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)oxolan-3-ol ChemAxon average_mass 251.2419 ChemAxon mono_mass 251.101839307 ChemAxon smiles NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](CO)O1 ChemAxon formula C10H13N5O3 ChemAxon inchi InChI=1S/C10H13N5O3/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(17)6(2-16)18-7/h3-7,16-17H,1-2H2,(H2,11,12,13)/t5-,6+,7+/m0/s1 ChemAxon inchikey OLXZPDWKRNYJJZ-RRKCRQDMSA-N ChemAxon polar_surface_area 119.31 ChemAxon refractivity 61.68 ChemAxon polarizability 24.24 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 7 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Purine metabolism ec00230 purine deoxyribonucleosides degradation PW002077 Metabolic purine deoxyribonucleosides degradation PWY0-1297 Specdb::CMs 859 Specdb::CMs 860 Specdb::CMs 2044 Specdb::CMs 3299 Specdb::CMs 30164 Specdb::CMs 30843 Specdb::CMs 30998 Specdb::CMs 37295 Specdb::CMs 130885 Specdb::CMs 138619 Specdb::CMs 1050048 Specdb::CMs 1050050 Specdb::CMs 1050052 Specdb::CMs 1050054 Specdb::CMs 1050056 Specdb::CMs 1050058 Specdb::CMs 1050060 Specdb::CMs 1050062 Specdb::CMs 1050064 Specdb::CMs 1050066 Specdb::CMs 1050067 Specdb::CMs 1050069 Specdb::CMs 1050071 Specdb::NmrOneD 1085 Specdb::NmrOneD 142210 Specdb::NmrOneD 142211 Specdb::NmrOneD 142212 Specdb::NmrOneD 142213 Specdb::NmrOneD 142214 Specdb::NmrOneD 142215 Specdb::NmrOneD 142216 Specdb::NmrOneD 142217 Specdb::NmrOneD 142218 Specdb::NmrOneD 142219 Specdb::NmrOneD 142220 Specdb::NmrOneD 142221 Specdb::NmrOneD 142222 Specdb::NmrOneD 142223 Specdb::NmrOneD 142224 Specdb::NmrOneD 142225 Specdb::NmrOneD 142226 Specdb::NmrOneD 142227 Specdb::NmrOneD 142228 Specdb::NmrOneD 142229 Specdb::MsMs 6213 Specdb::MsMs 6214 Specdb::MsMs 6215 Specdb::MsMs 6216 Specdb::MsMs 6217 Specdb::MsMs 6218 Specdb::MsMs 6221 Specdb::MsMs 6222 Specdb::MsMs 179856 Specdb::MsMs 179857 Specdb::MsMs 179858 Specdb::MsMs 182190 Specdb::MsMs 182191 Specdb::MsMs 182192 Specdb::MsMs 439816 Specdb::MsMs 439817 Specdb::MsMs 446029 Specdb::MsMs 446030 Specdb::MsMs 446031 Specdb::MsMs 446032 Specdb::MsMs 446033 Specdb::MsMs 447223 Specdb::MsMs 447968 Specdb::MsMs 447969 Specdb::MsMs 449648 Specdb::NmrTwoD 1143 HMDB00101 13135 C00559 DEOXYADENOSINE 3D1 Deoxyadenosine Keseler, I. 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Potential anticancer agents. XIX. Synthesis of 2-deoxyadenosine. Journal of the American Chemical Society (1959), 81 3967-74. http://hmdb.ca/system/metabolites/msds/000/000/070/original/HMDB00101.pdf?1358462218 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 Adenosine deaminase P22333 ADD_ECOLI add http://ecmdb.ca/proteins/P22333.xml 5'-nucleotidase yfbR P76491 YFBR_ECOLI yfbR http://ecmdb.ca/proteins/P76491.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 Deoxyadenosine monophosphate + Water > Deoxyadenosine + Phosphate Deoxyadenosine + Hydrogen ion + Water > Deoxyinosine + Ammonium Deoxyadenosine + Phosphate <> Deoxyribose 1-phosphate + Adenine R02557 Deoxyadenosine monophosphate + Water <> Deoxyadenosine + Phosphate R02088 Deoxyadenosine + Water <> Deoxyinosine + Ammonia R02556 Water + Deoxyadenosine > Ammonia + Deoxyinosine R02556 ADDALT-RXN Deoxyadenosine + Phosphate <> Adenine + deoxyribose-1-phosphate DEOXYADENPHOSPHOR-RXN Deoxyadenosine + Phosphate > Adenine + Deoxyribose 1-phosphate PW_R006069 Deoxyinosine + Ammonium < Water + Hydrogen ion + Deoxyadenosine PW_R006068 Deoxyadenosine monophosphate + Water > Deoxyadenosine + Phosphate 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 2.82 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 11280 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