2.02012-05-31 10:28:15 -06002015-09-13 12:56:08 -0600ECMDB00654M2MDB000165D-XyluloseD-xylulose is a monosaccharide containing five carbon atoms. D-xylulose is converted from xylitol by the enzyme NAD+-linked xylitol dehydrogenase (EC 1.1.1.9) in the glucuronate pathway. Most likely, D-xylulose (as well as D-arabinose or D-ribulose) is a precursor of the pentiol D-arabitol, since pentitols are derived from their corresponding pentose phosphate precursors via pentoses. Although pentitols are present in all living organisms, knowledge concerning their metabolism is limited. (PMID: 15234337, Mol Genet Metab. 2004 Jul;82(3):231-7.)D-Threo-PentuloseD-XyluloseXyluloseC5H10O5150.1299150.05282343(3S,4R)-1,3,4,5-tetrahydroxypentan-2-oneD-xylulose551-84-8[H][C@@](O)(CO)[C@]([H])(O)C(=O)COInChI=1S/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h3,5-8,10H,1-2H2/t3-,5+/m1/s1ZAQJHHRNXZUBTE-WUJLRWPWSA-NLiquidCytosollogp-2.16logs0.65solubility6.78e+02 g/lmelting_point15 oClogp-2.6pka_strongest_acidic10.57pka_strongest_basic-3iupac(3S,4R)-1,3,4,5-tetrahydroxypentan-2-oneaverage_mass150.1299mono_mass150.05282343smiles[H][C@@](O)(CO)[C@]([H])(O)C(=O)COformulaC5H10O5inchiInChI=1S/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h3,5-8,10H,1-2H2/t3-,5+/m1/s1inchikeyZAQJHHRNXZUBTE-WUJLRWPWSA-Npolar_surface_area97.99refractivity31.6polarizability13.53rotatable_bond_count4acceptor_count5donor_count4physiological_charge0formal_charge0Fructose and mannose metabolismec00051Pentose and glucuronate interconversionsec00040Metabolic pathwayseco01100xylose degradation IXYLCAT-PWYSpecdb::CMs766Specdb::CMs2440Specdb::CMs38135Specdb::NmrOneD1740Specdb::MsMs1666Specdb::MsMs1667Specdb::MsMs1668Specdb::MsMs178149Specdb::MsMs178150Specdb::MsMs178151Specdb::MsMs180465Specdb::MsMs180466Specdb::MsMs180467Specdb::NmrTwoD1085Specdb::NmrTwoD1680HMDB016446194451524C0031017140D-XYLULOSEXULXyluloseKeseler, 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 80:2939-2948.18331064Huck, J. H., Roos, B., Jakobs, C., van der Knaap, M. S., Verhoeven, N. M. (2004). "Evaluation of pentitol metabolism in mammalian tissues provides new insight into disorders of human sugar metabolism." Mol Genet Metab 82:231-237.15234337Takeuchi, Sonoko; Tonouchi, Naoto; Yokozeki, Kenzo. Production of xylitol or D-xylulose by fermentation of glucose with Gluconobacter, Acetobacter, and Frateuria. Eur. Pat. Appl. (2000), 10 pp. http://hmdb.ca/system/metabolites/msds/000/001/424/original/HMDB01644.pdf?1358463016Xylose isomeraseP00944XYLA_ECOLIxylAhttp://ecmdb.ca/proteins/P00944.xmlRibulokinaseP08204ARAB_ECOLIaraBhttp://ecmdb.ca/proteins/P08204.xmlXylulose kinaseP09099XYLB_ECOLIxylBhttp://ecmdb.ca/proteins/P09099.xmlSugar efflux transporter CP31436SETC_ECOLIsetChttp://ecmdb.ca/proteins/P31436.xmlAdenosine triphosphate + D-Xylulose <> ADP + Hydrogen ion + Xylulose 5-phosphateR01639XYLULOKIN-RXND-Xylose <> D-XyluloseR01432Adenosine triphosphate + D-Xylulose <> ADP + Xylulose 5-phosphateR01639D-xylose <> D-XyluloseXYLISOM-RXND-Xylulose + Adenosine triphosphate > Hydrogen ion + Xylulose 5-phosphate + ADPXYLULOKIN-RXND-Xylose > D-XyluloseAdenosine triphosphate + D-Xylulose > ADP + Xylulose 5-phosphate