2.0 2012-05-31 14:20:33 -0600 2015-09-17 15:41:45 -0600 ECMDB11688 M2MDB000819 Ribose 1,5-bisphosphate Ribose 1,5-bisphosphate (Rib-1,5-P2), a newly discovered activator of phosphofructokinase. It forms rapidly during the initiation of glycolytic flux and disappears within 20 s/ Ribose 1,5-bisphosphate is a potent regulator of the fructose 6-phosphate/fructose 1,6-bisphosphate cycle. Ribose 1,5-bisphosphate is a substrate for Ribose 1,5-bisphosphate phosphokinase (EC 2.7.4.23), an enzyme that catalyzes the chemical reaction. D-Ribose 1,5-bisphosphate D-Ribose 1,5-bisphosphoric acid D-Ribose 1,5-diphosphate D-Ribose 1,5-diphosphoric acid R1,5P Rib-1,5-P2 Ribose 1,5-bisphosphoric acid C5H12O11P2 310.0897 309.98548425 {[(3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]oxy}phosphonic acid ribose 1,5-bisphosphate 14689-84-0 O[C@H]1[C@@H](O)[C@@H](OP(O)(O)=O)O[C@@H]1COP(O)(O)=O InChI=1S/C5H12O11P2/c6-3-2(1-14-17(8,9)10)15-5(4(3)7)16-18(11,12)13/h2-7H,1H2,(H2,8,9,10)(H2,11,12,13)/t2-,3-,4-,5-/m1/s1 AAAFZMYJJHWUPN-TXICZTDVSA-N Solid Cytosol logp -1.44 ALOGPS logs -1.30 ALOGPS solubility 1.56e+01 g/l ALOGPS logp -2.5 ChemAxon pka_strongest_acidic 0.89 ChemAxon pka_strongest_basic -3.7 ChemAxon iupac {[(3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]oxy}phosphonic acid ChemAxon average_mass 310.0897 ChemAxon mono_mass 309.98548425 ChemAxon smiles O[C@H]1[C@@H](O)[C@@H](OP(O)(O)=O)O[C@@H]1COP(O)(O)=O ChemAxon formula C5H12O11P2 ChemAxon inchi InChI=1S/C5H12O11P2/c6-3-2(1-14-17(8,9)10)15-5(4(3)7)16-18(11,12)13/h2-7H,1H2,(H2,8,9,10)(H2,11,12,13)/t2-,3-,4-,5-/m1/s1 ChemAxon inchikey AAAFZMYJJHWUPN-TXICZTDVSA-N ChemAxon polar_surface_area 183.21 ChemAxon refractivity 51.71 ChemAxon polarizability 22.81 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 9 ChemAxon donor_count 6 ChemAxon physiological_charge -4 ChemAxon formal_charge 0 ChemAxon Pentose phosphate pathway ec00030 Phosphonate and phosphinate metabolism ec00440 PRPP Biosynthesis The biosynthesis of phosphoribosyl pyrophosphate begins with a product of the pentose phosphate, D-ribose 5-phosphate interact with a phosphopentomutase resulting in a Ribose 1-phosphate or it can be phosphorylated through an ATP driven ribose-phosphate diphosphokinase resulting in a release of a hydrogen ion, an AMP and a phosphoribosyl pyrophosphate. The latter compound is then involved in the purine nucleotides de novo biosynthesis pathway. Ribose 1-phosphate can interact spontaneously with ATP resulting in a release of hydrogen ion, ADP and a ribose 1,5-biphosphate. The latter compound is then phosphorylated through a ribose 1,5-bisphosphokinase resulting in the release of ADP and phosphoribosyl pyrophosphate. The latter compound is then involved in the purine nucleotides de novo biosynthesis pathway. PW000909 Metabolic methylphosphonate degradation I The pathway of methylphosphonate degradation starts with methylphosphonate being degrade by an ATP driven methylphosphonate degradation complex resulting in a alpha-D-ribose-1-methylphosphonate-5-triphosphate. This compound in turn is degraded by a water driven RPnTP hydrolase resulting in the release of a hydrogen ion, a pyrophosphate and a alpha-Dribose-1-methylphosphonate 5-phosphate. The latter compound is then involved with a carbon-phosphorous lyase resulting in the release of a methane and a 5-phospho-alpha-D-ribose 1,2-cyclic phosphate. This compound in turn gets degraded by a water driven 5-phospho-alpha-D-ribosyl 1,2-cyclic phosphate phosphodiesterase resulting in the release of a hydrogen ion and a alpha-D-ribose 1,5-biphosphate. PW002065 Metabolic methylphosphonate degradation PWY0-1533 PRPP biosynthesis II PWY0-661 Specdb::MsMs 29051 Specdb::MsMs 29052 Specdb::MsMs 29053 Specdb::MsMs 35609 Specdb::MsMs 35610 Specdb::MsMs 35611 HMDB11688 3036640 26328792 C01151 17994 RIBOSE-15-BISPHOSPHATE 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 Phosphopentomutase P0A6K6 DEOB_ECOLI deoB http://ecmdb.ca/proteins/P0A6K6.xml ATP-binding protein phnN P16690 PHNN_ECOLI phnN http://ecmdb.ca/proteins/P16690.xml Phosphoglucomutase P36938 PGM_ECOLI pgm http://ecmdb.ca/proteins/P36938.xml Phosphoribosyl 1,2-cyclic phosphodiesterase P16692 PHNP_ECOLI phnP http://ecmdb.ca/proteins/P16692.xml Adenosine triphosphate + Ribose 1,5-bisphosphate <> ADP + Phosphoribosyl pyrophosphate R06836 RXN0-1401 Ribose-1-phosphate + Adenosine triphosphate > Hydrogen ion + Ribose 1,5-bisphosphate + ADP RXN0-1402 α-D-ribose-1,2-cyclic-phosphate-5-phosphate + Water > Hydrogen ion + Ribose 1,5-bisphosphate RXN0-6710 Ribose 1,5-bisphosphate + Adenosine triphosphate > Phosphoribosyl pyrophosphate + ADP R06836 RXN0-1401 Water <> Ribose 1,5-bisphosphate R10205 Ribose 1,5-bisphosphate + Adenosine triphosphate + Ribose 1,5-bisphosphate > Adenosine diphosphate + Phosphoribosyl pyrophosphate + ADP PW_R003409 alpha-D-Ribose 1,2-cyclic phosphate 5-phosphate + Water > Hydrogen ion + Ribose 1,5-bisphosphate PW_R006038