2.0 2012-05-31 10:28:15 -0600 2015-09-13 12:56:08 -0600 ECMDB00654 M2MDB000165 D-Xylulose D-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-Pentulose D-Xylulose Xylulose C5H10O5 150.1299 150.05282343 (3S,4R)-1,3,4,5-tetrahydroxypentan-2-one D-xylulose 551-84-8 [H][C@@](O)(CO)[C@]([H])(O)C(=O)CO InChI=1S/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h3,5-8,10H,1-2H2/t3-,5+/m1/s1 ZAQJHHRNXZUBTE-WUJLRWPWSA-N Liquid Cytosol logp -2.16 ALOGPS logs 0.65 ALOGPS solubility 6.78e+02 g/l ALOGPS melting_point 15 oC logp -2.6 ChemAxon pka_strongest_acidic 10.57 ChemAxon pka_strongest_basic -3 ChemAxon iupac (3S,4R)-1,3,4,5-tetrahydroxypentan-2-one ChemAxon average_mass 150.1299 ChemAxon mono_mass 150.05282343 ChemAxon smiles [H][C@@](O)(CO)[C@]([H])(O)C(=O)CO ChemAxon formula C5H10O5 ChemAxon inchi InChI=1S/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h3,5-8,10H,1-2H2/t3-,5+/m1/s1 ChemAxon inchikey ZAQJHHRNXZUBTE-WUJLRWPWSA-N ChemAxon polar_surface_area 97.99 ChemAxon refractivity 31.6 ChemAxon polarizability 13.53 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Fructose and mannose metabolism ec00051 Pentose and glucuronate interconversions ec00040 Metabolic pathways eco01100 xylose degradation I XYLCAT-PWY Specdb::CMs 766 Specdb::CMs 2440 Specdb::CMs 38135 Specdb::NmrOneD 1740 Specdb::MsMs 1666 Specdb::MsMs 1667 Specdb::MsMs 1668 Specdb::MsMs 178149 Specdb::MsMs 178150 Specdb::MsMs 178151 Specdb::MsMs 180465 Specdb::MsMs 180466 Specdb::MsMs 180467 Specdb::NmrTwoD 1085 Specdb::NmrTwoD 1680 HMDB01644 619 4451524 C00310 17140 D-XYLULOSE XUL Xylulose 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 van 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. 17765195 Winder, 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. 18331064 Huck, 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. 15234337 Takeuchi, 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?1358463016 Xylose isomerase P00944 XYLA_ECOLI xylA http://ecmdb.ca/proteins/P00944.xml Ribulokinase P08204 ARAB_ECOLI araB http://ecmdb.ca/proteins/P08204.xml Xylulose kinase P09099 XYLB_ECOLI xylB http://ecmdb.ca/proteins/P09099.xml Sugar efflux transporter C P31436 SETC_ECOLI setC http://ecmdb.ca/proteins/P31436.xml Adenosine triphosphate + D-Xylulose <> ADP + Hydrogen ion + Xylulose 5-phosphate R01639 XYLULOKIN-RXN D-Xylose <> D-Xylulose R01432 Adenosine triphosphate + D-Xylulose <> ADP + Xylulose 5-phosphate R01639 D-xylose <> D-Xylulose XYLISOM-RXN D-Xylulose + Adenosine triphosphate > Hydrogen ion + Xylulose 5-phosphate + ADP XYLULOKIN-RXN D-Xylose > D-Xylulose Adenosine triphosphate + D-Xylulose > ADP + Xylulose 5-phosphate