2.02012-05-31 13:03:42 -06002015-10-15 16:13:48 -0600ECMDB01031M2MDB000230Deoxyribose 5-phosphateDeoxyribose 5-phosphate is a a metabolite in the pentose phosphate pathway. It can be generated from D-glyceraldehdye-3 phosphate via the enzyme 2-Deoxyribose 5-phosphate aldolase (DERA). Alternately Deoxyribose 5-phosphate can be converted to D-glyceraldehyde-3 phosphate that can then feed into the pentose phosphate pathway. Deoxyribose 5-phosphate can also be generated from 2-Deoxy-D-ribose via the enzyme Ribokinase (EC 2.7.1.15). It has been shown in a number of organisms that deoxynucleosides or deoxyriboses cause the induction of aldolases (such as DERA) involved in their catabolism, leading to the utilisation of the pentose moiety as carbon and energy source.2-Deoxy-a-D-ribose 5-phosphate2-Deoxy-a-D-ribose 5-phosphoric acid2-Deoxy-a-delta-ribose 5-phosphate2-Deoxy-a-delta-ribose 5-phosphoric acid2-Deoxy-a-δ-ribose 5-phosphate2-Deoxy-a-δ-ribose 5-phosphoric acid2-Deoxy-alpha-D-ribose 5-phosphate2-Deoxy-alpha-D-ribose 5-phosphoric acid2-Deoxy-alpha-delta-ribose 5-phosphate2-Deoxy-alpha-delta-ribose 5-phosphoric acid2-Deoxy-D-ribose 5-phosphate2-Deoxy-D-ribose 5-phosphoric acid2-Deoxy-D-ribose-5-phosphate2-Deoxy-D-ribose-5-phosphoric acid2-Deoxy-α-D-ribose 5-phosphate2-Deoxy-α-D-ribose 5-phosphoric acid2-Deoxy-α-δ-ribose 5-phosphate2-Deoxy-α-δ-ribose 5-phosphoric acid2-Deoxyribose 5-phosphate2-Deoxyribose 5-phosphoric acid2-Deoxyribose-5-p2-Deoxyribose-5-phosphate2-Deoxyribose-5-phosphoric acidDeoxy-ribose-5pDeoxyribose 5-phosphateDeoxyribose 5-phosphoric acidDeoxyribose-5-pDeoxyribose-5-phosphateDeoxyribose-5-phosphoric acidDR5PC5H11O7P214.1104214.024239218{[(2R,3S)-3,5-dihydroxyoxolan-2-yl]methoxy}phosphonic acid[(2R,3S)-3,5-dihydroxyoxolan-2-yl]methoxyphosphonic acid102916-66-5O[C@H]1C[C@H](O)[C@@H](COP(O)(O)=O)O1InChI=1S/C5H11O7P/c6-3-1-5(7)12-4(3)2-11-13(8,9)10/h3-7H,1-2H2,(H2,8,9,10)/t3-,4+,5+/m0/s1KKZFLSZAWCYPOC-VPENINKCSA-NSolidCytosollogp-2.14logs-0.76solubility3.75e+01 g/llogp-1.5pka_strongest_acidic1.23pka_strongest_basic-3.3iupac{[(2R,3S)-3,5-dihydroxyoxolan-2-yl]methoxy}phosphonic acidaverage_mass214.1104mono_mass214.024239218smilesO[C@H]1C[C@H](O)[C@@H](COP(O)(O)=O)O1formulaC5H11O7PinchiInChI=1S/C5H11O7P/c6-3-1-5(7)12-4(3)2-11-13(8,9)10/h3-7H,1-2H2,(H2,8,9,10)/t3-,4+,5+/m0/s1inchikeyKKZFLSZAWCYPOC-VPENINKCSA-Npolar_surface_area116.45refractivity39.32polarizability17.2rotatable_bond_count3acceptor_count6donor_count4physiological_charge-2formal_charge0Pentose phosphate pathwayec00030pyrimidine deoxyribonucleosides degradationPWY0-1298purine deoxyribonucleosides degradationPWY0-1297Specdb::MsMs24929Specdb::MsMs24930Specdb::MsMs24931Specdb::MsMs31487Specdb::MsMs31488Specdb::MsMs31489HMDB0103163525057464C0067316132DEOXY-RIBOSE-5PKeseler, 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-D590.21097882Kanehisa, 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-D114.22080510van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25.17765195Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948.18331064Bennett, 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 5:593-599.19561621Method of preparing 2-deoxyribose 5-phosphate US Patent http://hmdb.ca/system/metabolites/msds/000/000/926/original/HMDB01031.pdf?1358463351PhosphopentomutaseP0A6K6DEOB_ECOLIdeoBhttp://ecmdb.ca/proteins/P0A6K6.xmlDeoxyribose-phosphate aldolaseP0A6L0DEOC_ECOLIdeoChttp://ecmdb.ca/proteins/P0A6L0.xmlRibokinaseP0A9J6RBSK_ECOLIrbsKhttp://ecmdb.ca/proteins/P0A9J6.xmlDeoxyribose 5-phosphate <> Acetaldehyde + D-Glyceraldehyde 3-phosphateR01066DEOXYRIBOSE-P-ALD-RXNDeoxyribose 1-phosphate <> Deoxyribose 5-phosphateR02749D-PPENTOMUT-RXNDeoxyribose 5-phosphate + ADP <> Deoxyribose + Adenosine triphosphateR027502-deoxy-alpha-D-ribose 1-phosphate > Deoxyribose 5-phosphateDeoxyribose 5-phosphate > D-Glyceraldehyde 3-phosphate + AcetaldehydeGutnick 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 culture303.0uM0.037 oCK12 NCM3722Mid-Log Phase12120000Bennett, 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