2.0 2015-09-08 17:50:06 -0600 2015-09-14 16:46:35 -0600 ECMDB24214 M2MDB006331 D-ribofuranose 5-phosphate D-ribofuranose 5-phosphate is an intermediate in several pathways in E. coli., adenosine nucleotides degradation III, NAD salvage pathway I and D-ribofuranose 5-phosphate pathway. In adenosine nucleotides degradation III pathway, it is a product for enzyme AMP nucleosidase which catalyzes the reaction AMP + H2O -> D-ribofuranose 5-phosphate + adenine. It is also a product for enzyme NMN nucleosidase that catalyzes the reaction beta-nicotinamide D-ribonucleotide + H2O -> D-ribofuranose 5-phosphate + nicotinamide + H+ in pathway NAD salvage pathway I. It is a substrate for enzyme pseudouridine 5'-phosphate glycosidase that catalyzes the reaction D-ribofuranose 5-phosphate + uracil -> pseudouridine 5'-phosphate + H2O in pseudouridine degradation pathway (BioCyc compound: CPD-15317). D-Ribofuranose 5-phosphoric acid C5H9O8P 228.094 228.004601408 (3,4,5-trihydroxyoxolan-2-yl)methyl phosphate (3,4,5-trihydroxyoxolan-2-yl)methyl phosphate OC1OC(COP([O-])([O-])=O)C(O)C1O InChI=1S/C5H11O8P/c6-3-2(1-12-14(9,10)11)13-5(8)4(3)7/h2-8H,1H2,(H2,9,10,11)/p-2 KTVPXOYAKDPRHY-UHFFFAOYSA-L logp -2.04 ALOGPS logs -0.46 ALOGPS solubility 9.15e+01 g/l ALOGPS logp -2.4 ChemAxon pka_strongest_acidic 1.22 ChemAxon pka_strongest_basic -3.7 ChemAxon iupac (3,4,5-trihydroxyoxolan-2-yl)methyl phosphate ChemAxon average_mass 228.094 ChemAxon mono_mass 228.004601408 ChemAxon smiles OC1OC(COP([O-])([O-])=O)C(O)C1O ChemAxon formula C5H9O8P ChemAxon inchi InChI=1S/C5H11O8P/c6-3-2(1-12-14(9,10)11)13-5(8)4(3)7/h2-8H,1H2,(H2,9,10,11)/p-2 ChemAxon inchikey KTVPXOYAKDPRHY-UHFFFAOYSA-L ChemAxon polar_surface_area 142.34 ChemAxon refractivity 38.59 ChemAxon polarizability 17.71 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 7 ChemAxon donor_count 3 ChemAxon physiological_charge -2 ChemAxon formal_charge -2 ChemAxon NAD salvage Even though NAD molecules are not consumed during oxidation reactions, they have a relatively short half-life. For example, in E. coli the NAD+ half-life is 90 minutes. Once enzymatically degraded, the pyrimidine moiety of the molecule can be recouped via the NAD salvage cycles. This pathway is used for two purposes: it recycles the internally degraded NAD products nicotinamide D-ribonucleotide (also known as nicotinamide mononucleotide, or NMN) and nicotinamide, and it is used for the assimilation of exogenous NAD+. NAD reacts spontaneously with water resulting in the release of hydrogen ion, AMP and beta-nicotinamide D-ribonucleotide. This enzyme can either interact spontaneously with water resulting in the release of D-ribofuranose 5-phosphate, hydrogen ion and Nacinamide. On the other hand beta-nicotinamide D-ribonucleotide can also react with water through NMN amidohydrolase resulting in ammonium, and Nicotinate beta-D-ribonucleotide. Also it can interact with water spontaneously resulting in the release of phosphate resulting in a Nicotinamide riboside. Niacinamide interacts with water through a nicotinamidase resulting in a release of ammonium and nicotinic acid. This compound interacts with water and phosphoribosyl pyrophosphate through an ATP driven nicotinate phosphoribosyltransferase resulting in the release of ADP, pyrophosphate and phosphate and nicotinate beta-D-ribonucleotide. Nicotinamide riboside interacts with an ATP driven NadR DNA-binding transcriptional repressor and NMN adenylyltransferase (Escherichia coli) resulting in a ADP, hydrogen ion and beta-nicotinamide D-ribonucleotide. This compound interacts with ATP and hydrogen ion through NadR DNA-binding transcriptional repressor and NMN adenylyltransferase resulting in pyrophosphate and NAD. Nicotinate beta-D-ribonucleotide is adenylated through the interaction with ATP and a hydrogen ion through a nicotinate-mononucleotide adenylyltransferase resulting in pyrophosphate and Nicotinic acid adenine dinucleotide. Nicotinic acid adenine dinucleotide interacts with L-glutamine and water through an ATP driven NAD synthetase, NH3-dependent resulting in AMP, pyrophosphate, hydrogen ion, L-glutamic acid and NAD. PW000830 Metabolic Purine degradation Pseudouridine is phosphorylated by interacting with atp and a psuK resulting in the release of an ADP, a hydrogen ion and a pseudouridine 5'-phosphate. The latter compound then reacts with water through a pseudouridine 5'-phosphate glycosidase resulting in the release of a uracil and D-ribofuranose 5-phosphate PW001887 Metabolic Specdb::NmrOneD 330522 Specdb::NmrOneD 330523 Specdb::NmrOneD 330524 Specdb::NmrOneD 330525 Specdb::NmrOneD 330526 Specdb::NmrOneD 330527 Specdb::NmrOneD 330528 Specdb::NmrOneD 330529 Specdb::NmrOneD 330530 Specdb::NmrOneD 330531 Specdb::NmrOneD 330532 Specdb::NmrOneD 330533 Specdb::NmrOneD 330534 Specdb::NmrOneD 330535 Specdb::NmrOneD 330536 Specdb::NmrOneD 330537 Specdb::NmrOneD 330538 Specdb::NmrOneD 330539 Specdb::NmrOneD 330540 Specdb::NmrOneD 330541 Specdb::MsMs 24671 Specdb::MsMs 24672 Specdb::MsMs 24673 Specdb::MsMs 31229 Specdb::MsMs 31230 Specdb::MsMs 31231 Pseudouridine 5'-phosphate + Water > Uracil + D-ribofuranose 5-phosphate + D-ribofuranose 5-phosphate PW_R005151