2.0 2012-05-31 13:49:11 -0600 2015-09-13 15:15:22 -0600 ECMDB01292 M2MDB000325 1-Deoxy-D-xylulose 1-deoxy-D-xylulose 5-phosphate serves as a precursor for the biosynthesis of the vitamins thiamine and pyridoxal and for the formation of isopentenyl pyrophosphate and dimethylallyl pyrophosphate via the nonmevalonate pathway of terpenoid biosynthesis. Escherichia coli incorporates unphosphorylated 1-deoxy-D-xylulose into the terpenoid side chain of ubiquinones with high efficacy. D-xylulokinase (EC 2.7.1.17) catalyzes the phosphorylation of 1-deoxy-D-xylulose 1-Deoxy-2-pentulose 1-Deoxy-D-threo-2-pentulose 1-Deoxy-D-threo-2-Pentulose (9CI) 1-Deoxy-D-threo-pentulose 1-Deoxy-D-xylulose 1-Deoxy-xylulose D-1-Deoxyxylulose Deoxyxylulose DXylulose C5H10O4 134.1305 134.057908808 (2S,3S,4R)-2-(hydroxymethyl)oxolane-3,4-diol 1-deoxy-xylulose 60299-43-6 OC[C@@H]1OC[C@@H](O)[C@@H]1O InChI=1S/C5H10O4/c6-1-4-5(8)3(7)2-9-4/h3-8H,1-2H2/t3-,4+,5+/m1/s1 KZVAAIRBJJYZOW-WISUUJSJSA-N Solid Cytosol logp -1.98 ALOGPS logs 0.89 ALOGPS solubility 1.05e+03 g/l ALOGPS logp -1.9 ChemAxon pka_strongest_acidic 12.88 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2S,3S,4R)-2-(hydroxymethyl)oxolane-3,4-diol ChemAxon average_mass 134.1305 ChemAxon mono_mass 134.057908808 ChemAxon smiles OC[C@@H]1OC[C@@H](O)[C@@H]1O ChemAxon formula C5H10O4 ChemAxon inchi InChI=1S/C5H10O4/c6-1-4-5(8)3(7)2-9-4/h3-8H,1-2H2/t3-,4+,5+/m1/s1 ChemAxon inchikey KZVAAIRBJJYZOW-WISUUJSJSA-N ChemAxon polar_surface_area 69.92 ChemAxon refractivity 28.93 ChemAxon polarizability 12.64 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 21577 Specdb::CMs 38010 Specdb::CMs 156176 Specdb::NmrOneD 147190 Specdb::NmrOneD 147191 Specdb::NmrOneD 147192 Specdb::NmrOneD 147193 Specdb::NmrOneD 147194 Specdb::NmrOneD 147195 Specdb::NmrOneD 147196 Specdb::NmrOneD 147197 Specdb::NmrOneD 147198 Specdb::NmrOneD 147199 Specdb::NmrOneD 147200 Specdb::NmrOneD 147201 Specdb::NmrOneD 147202 Specdb::NmrOneD 147203 Specdb::NmrOneD 147204 Specdb::NmrOneD 147205 Specdb::NmrOneD 147206 Specdb::NmrOneD 147207 Specdb::NmrOneD 147208 Specdb::NmrOneD 147209 Specdb::MsMs 27722 Specdb::MsMs 27723 Specdb::MsMs 27724 Specdb::MsMs 34280 Specdb::MsMs 34281 Specdb::MsMs 34282 Specdb::MsMs 2699890 Specdb::MsMs 2699891 Specdb::MsMs 2699892 Specdb::MsMs 3006249 Specdb::MsMs 3006250 Specdb::MsMs 3006251 HMDB01292 17216098 C06257 16493 CPD-1093 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 Backstrom, Allyson D.; Austin, R.; McMordie Austin S.; Begley, Tadhg P. A new synthesis of 1-deoxy-D-threo-2-pentulose, a biosynthetic precursor to the thiazole moiety of thiamin. Journal of Carbohydrate Chemistry (1995), 14(1), 171-5. Xylulose kinase P09099 XYLB_ECOLI xylB http://ecmdb.ca/proteins/P09099.xml Adenosine triphosphate + 1-Deoxy-D-xylulose > ADP + 1-Deoxy-D-xylulose 5-phosphate + Hydrogen ion RXN0-382