2.0 2012-05-31 14:40:04 -0600 2015-07-07 11:22:39 -0600 ECMDB20343 M2MDB001172 beta-D-ribofuranose Beta-D-ribofuranose is the cyclic form of D-ribose. Ribose, primarily occurring as D-ribose, is an organic compound that occurs widely in nature. It is an aldopentose, a monosaccharide containing five carbon atoms that in its acyclic form has an aldehyde functional group at one end. Typically, ribose exists in the cyclic form. It comprises the backbone of RNA, a biopolymer that is the basis of genetic transcription. It is related to deoxyribose, as found in DNA, by the removal of one hydroxy group. Once phosphorylated, ribose can become a subunit of ATP, NADH, and several other compounds that are critical to metabolism. a D-Ribose a-D-Ribofuranose a-D-Ribose a-D-Ribose-5 a-delta-Ribose a-delta-Ribose-5 a-δ-Ribose a-δ-Ribose-5 Alpha D-Ribose Alpha-D-Ribofuranose Alpha-D-Ribose Alpha-D-Ribose-5 Alpha-delta-Ribose Alpha-delta-Ribose-5 b-D-Rib b-D-Ribofuranose b-D-Ribofuranosyl b-D-Ribopyranose b-D-Ribose BDR Beta-D-Rib Beta-D-Ribofuranose Beta-D-Ribofuranosyl Beta-D-Ribopyranose Beta-D-Ribose D-(-)-Ribose D-Ribo-2,3,4,5-tetrahydroxyvaleraldehyde D-Ribose Delta-(-)-Ribose Delta-Ribo-2,3,4,5-tetrahydroxyvaleraldehyde Delta-Ribose Pentose RIB Ribose α D-Ribose α-D-Ribofuranose α-D-Ribose α-D-Ribose-5 α-δ-Ribose α-δ-Ribose-5 β-D-Rib β-D-Ribofuranose β-D-Ribofuranosyl β-D-Ribopyranose β-D-Ribose δ-(-)-Ribose δ-ribo-2,3,4,5-Tetrahydroxyvaleraldehyde δ-Ribose C5H10O5 150.1299 150.05282343 (2R,3R,4S,5R)-5-(hydroxymethyl)oxolane-2,3,4-triol β-D-ribofuranoside 50-69-1 [H][C@@]1(O)O[C@]([H])(CO)[C@@]([H])(O)[C@@]1([H])O InChI=1S/C5H10O5/c6-1-2-3(7)4(8)5(9)10-2/h2-9H,1H2/t2-,3-,4-,5-/m1/s1 HMFHBZSHGGEWLO-TXICZTDVSA-N Solid Cytoplasm Periplasm logp -2.65 ALOGPS logs 0.85 ALOGPS solubility 1.07e+03 g/l ALOGPS melting_point 95 oC logp -2.3 ChemAxon pka_strongest_acidic 11.31 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2R,3R,4S,5R)-5-(hydroxymethyl)oxolane-2,3,4-triol ChemAxon average_mass 150.1299 ChemAxon mono_mass 150.05282343 ChemAxon smiles [H][C@@]1(O)O[C@]([H])(CO)[C@@]([H])(O)[C@@]1([H])O ChemAxon formula C5H10O5 ChemAxon inchi InChI=1S/C5H10O5/c6-1-2-3(7)4(8)5(9)10-2/h2-9H,1H2/t2-,3-,4-,5-/m1/s1 ChemAxon inchikey HMFHBZSHGGEWLO-TXICZTDVSA-N ChemAxon polar_surface_area 90.15 ChemAxon refractivity 29.96 ChemAxon polarizability 13.62 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon ABC transporters ec02010 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 Ribose Degradation D-ribose, which can serve as a total source of carbon and energy for E. coli, enters the cell via a high-affinity ABC transport system and hence in unphosphorylated form. The crystal structure of the periplasmic ribose binding protein of the ribose ABC transporter showed it to bind (and thus presumably to facilitate transport of) β-D-ribopyranose. ribose pyranase accelerates the conversion between the pyranose and furanose forms of β-D-ribose. Interconversion of the α- and β-anomers of D-ribofuranose is fast and spontaneous. ribokinase then converts it to D-ribose 5-phosphate, an intermediate of the pentose phosphate pathway, and hence it flows through the pathways of central metabolism to satisfy the cell's need for precursor metabolites, reducing power, and metabolic energy. (EcoCyc) PW002102 Metabolic ribose degradation RIBOKIN-PWY Specdb::CMs 1085932 Specdb::NmrOneD 257108 Specdb::NmrOneD 257109 Specdb::NmrOneD 257110 Specdb::NmrOneD 257111 Specdb::NmrOneD 257112 Specdb::NmrOneD 257113 Specdb::NmrOneD 257114 Specdb::NmrOneD 257115 Specdb::NmrOneD 257116 Specdb::NmrOneD 257117 Specdb::NmrOneD 257118 Specdb::NmrOneD 257119 Specdb::NmrOneD 257120 Specdb::NmrOneD 257121 Specdb::NmrOneD 257122 Specdb::NmrOneD 257123 Specdb::NmrOneD 257124 Specdb::NmrOneD 257125 Specdb::NmrOneD 257126 Specdb::NmrOneD 257127 Specdb::MsMs 29750 Specdb::MsMs 29751 Specdb::MsMs 29752 Specdb::MsMs 36308 Specdb::MsMs 36309 Specdb::MsMs 36310 447347 C16639 47002 CPD0-1108 HSU Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 Riboflavin synthase alpha chain P0AFU8 RISA_ECOLI ribE http://ecmdb.ca/proteins/P0AFU8.xml D-ribose pyranase P04982 RBSD_ECOLI rbsD http://ecmdb.ca/proteins/P04982.xml Sugar efflux transporter C P31436 SETC_ECOLI setC http://ecmdb.ca/proteins/P31436.xml beta-D-Ribopyranose <> beta-D-ribofuranose R08247 RXN0-5304 beta-D-ribofuranose <> D-ribose RXN0-5305 beta-D-ribofuranose <> beta-D-Ribopyranose RXN0-5304 beta-D-Ribopyranose > beta-D-ribofuranose Adenosine + Water > beta-D-ribofuranose + Adenine PW_R006054