2.0 2012-05-31 14:06:39 -0600 2015-06-04 15:58:34 -0600 ECMDB04149 M2MDB000639 L-Ribulose Ribulose is a ketopentose- a monosaccharide containing five carbon atoms, and including a ketone functional group. It has chemical formula C5H10O5. Two diastereomers are possible, D-ribulose (D-erythro-pentulose) and L-ribulose (L-erythro-pentulose). D-ribulose is an intermediate in the fungal pathway for D-arabitol production. Ribulose C5H10O5 150.1299 150.05282343 (3S,4R)-2-(hydroxymethyl)oxolane-2,3,4-triol (3S,4R)-2-(hydroxymethyl)oxolane-2,3,4-triol 2042-27-5 OCC1(O)OC[C@@H](O)[C@@H]1O InChI=1S/C5H10O5/c6-2-5(9)4(8)3(7)1-10-5/h3-4,6-9H,1-2H2/t3-,4+,5?/m1/s1 LQXVFWRQNMEDEE-OVEKKEMJSA-N Solid Cytosol logp -2.20 ALOGPS logs 0.94 ALOGPS solubility 1.31e+03 g/l ALOGPS logp -2.1 ChemAxon pka_strongest_acidic 10.29 ChemAxon pka_strongest_basic -3.5 ChemAxon iupac (3S,4R)-2-(hydroxymethyl)oxolane-2,3,4-triol ChemAxon average_mass 150.1299 ChemAxon mono_mass 150.05282343 ChemAxon smiles OCC1(O)OC[C@@H](O)[C@@H]1O ChemAxon formula C5H10O5 ChemAxon inchi InChI=1S/C5H10O5/c6-2-5(9)4(8)3(7)1-10-5/h3-4,6-9H,1-2H2/t3-,4+,5?/m1/s1 ChemAxon inchikey LQXVFWRQNMEDEE-OVEKKEMJSA-N ChemAxon polar_surface_area 90.15 ChemAxon refractivity 30.4 ChemAxon polarizability 13.46 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Pentose and glucuronate interconversions ec00040 Metabolic pathways eco01100 L-arabinose Degradation I Because L-arabinose enters E. coli either by a low-affinity proton-driven transporter (AraE) or a high-affinity ATP-driven system (AraFGH), its first intracellular form is unphosphorylated. Then an isomerase and a kinase convert it to L-ribulose-5-phosphate. An epimerase converts L-ribulose-5-phosphate to D-xylulose-5-phosphate, an intermediate of the pentose phosphate pathway, which thereby flows through the pathways of central metabolism to satisfy the cell's need for precursor metabolites, reducing power, and metabolic energy. (EcoCyc) PW002103 Metabolic L-arabinose degradation I ARABCAT-PWY Specdb::CMs 1344 Specdb::CMs 1356 Specdb::CMs 21424 Specdb::CMs 30160 Specdb::CMs 30184 Specdb::CMs 30284 Specdb::CMs 30285 Specdb::CMs 30786 Specdb::CMs 31458 Specdb::CMs 31459 Specdb::CMs 38586 Specdb::MsMs 26285 Specdb::MsMs 26286 Specdb::MsMs 26287 Specdb::MsMs 32843 Specdb::MsMs 32844 Specdb::MsMs 32845 HMDB03371 619 388344 C00508 16880 L-RIBULOSE L-Ribulose 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 Yasuda, Mari; Kawaguchi, Tomoko. Production method for L-ribulose from ribitol. Jpn. Kokai Tokkyo Koho (1999), 6 pp. L-arabinose isomerase P08202 ARAA_ECOLI araA http://ecmdb.ca/proteins/P08202.xml Ribulokinase P08204 ARAB_ECOLI araB http://ecmdb.ca/proteins/P08204.xml Sugar efflux transporter C P31436 SETC_ECOLI setC http://ecmdb.ca/proteins/P31436.xml L-Arabinose <> L-Ribulose R01761 Adenosine triphosphate + L-Ribulose > ADP + Hydrogen ion + L-Ribulose 5-phosphate R02439 RXN0-5116 Adenosine triphosphate + L-Ribulose <> ADP + L-Ribulose 5-phosphate R02439 RXN0-5116 L-arabinose <> L-Ribulose ARABISOM-RXN L-Arabinose > L-Ribulose Adenosine triphosphate + L-Ribulose + D-Ribulose <> ADP + L-Ribulose 5-phosphate + D-Ribulose 5-phosphate R01526 R02439 L-Ribulose + Adenosine triphosphate > L-ribulose 5-phosphate + ADP + Hydrogen ion PW_R006133