2.0 2012-05-31 10:28:12 -0600 2015-10-23 17:32:16 -0600 ECMDB00646 M2MDB000164 L-Arabinose L-Arabinose is a pentose with a sweet taste. In E coli, it is involved in the catabolism of arabinose, a process directed by the L-arabinose operon. This process is activated in the presence of arabinose and the absence of glucose. (Wikipedia) α-L-arabinose a-L-Arabinopyranose a-L-Arabinose Alpha-L-Arabinopyranose Alpha-L-Arabinose Arabinose L-(+)-Arabinose L-Arabinopyranose α-L-Arabinopyranose α-L-Arabinose C5H10O5 150.1299 150.05282343 (3R,4S,5S)-oxane-2,3,4,5-tetrol L-arabinopyranose 5328-37-0 O[C@H]1COC(O)[C@H](O)[C@H]1O InChI=1S/C5H10O5/c6-2-1-10-5(9)4(8)3(2)7/h2-9H,1H2/t2-,3-,4+,5?/m0/s1 SRBFZHDQGSBBOR-HWQSCIPKSA-N Solid Cytosol Extra-organism Periplasm logp -2.57 ALOGPS logs 0.91 ALOGPS solubility 1.22e+03 g/l ALOGPS melting_point 158-160 oC logp -2.3 ChemAxon pka_strongest_acidic 11.31 ChemAxon pka_strongest_basic -3.5 ChemAxon iupac (3R,4S,5S)-oxane-2,3,4,5-tetrol ChemAxon average_mass 150.1299 ChemAxon mono_mass 150.05282343 ChemAxon smiles O[C@H]1COC(O)[C@H](O)[C@H]1O ChemAxon formula C5H10O5 ChemAxon inchi InChI=1S/C5H10O5/c6-2-1-10-5(9)4(8)3(2)7/h2-9H,1H2/t2-,3-,4+,5?/m0/s1 ChemAxon inchikey SRBFZHDQGSBBOR-HWQSCIPKSA-N ChemAxon polar_surface_area 90.15 ChemAxon refractivity 29.96 ChemAxon polarizability 13.38 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Ascorbate and aldarate metabolism ec00053 Amino sugar and nucleotide sugar metabolism ec00520 Pentose and glucuronate interconversions ec00040 ABC transporters ec02010 Metabolic pathways eco01100 Specdb::CMs 2966 Specdb::CMs 37671 Specdb::NmrOneD 1454 Specdb::MsMs 179196 Specdb::MsMs 179197 Specdb::MsMs 179198 Specdb::MsMs 181521 Specdb::MsMs 181522 Specdb::MsMs 181523 Specdb::NmrTwoD 1399 HMDB00646 439195 388335 C00259 17535 ARABINOSE LAI Arabinose 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 Vijayendran, C., Barsch, A., Friehs, K., Niehaus, K., Becker, A., Flaschel, E. (2008). "Perceiving molecular evolution processes in Escherichia coli by comprehensive metabolite and gene expression profiling." Genome Biol 9:R72. 18402659 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 Osaki, S., Kimura, T., Sugimoto, T., Hizukuri, S., Iritani, N. (2001). "L-arabinose feeding prevents increases due to dietary sucrose in lipogenic enzymes and triacylglycerol levels in rats." J Nutr 131:796-799. 11238761 Whistler, Roy L.; Schweiger, Richard. Preparation of D-arabinose from D-glucose with hypochlorite. Journal of the American Chemical Society (1959), 81 5190-2. http://hmdb.ca/system/metabolites/msds/000/000/565/original/HMDB00646.pdf?1358894657 L-arabinose isomerase P08202 ARAA_ECOLI araA http://ecmdb.ca/proteins/P08202.xml Arabinose import ATP-binding protein AraG P0AAF3 ARAG_ECOLI araG http://ecmdb.ca/proteins/P0AAF3.xml L-arabinose transport system permease protein AraH P0AE26 ARAH_ECOLI araH http://ecmdb.ca/proteins/P0AE26.xml L-arabinose-binding periplasmic protein P02924 ARAF_ECOLI araF http://ecmdb.ca/proteins/P02924.xml Arabinose import ATP-binding protein AraG P0AAF3 ARAG_ECOLI araG http://ecmdb.ca/proteins/P0AAF3.xml Sugar efflux transporter C P31436 SETC_ECOLI setC http://ecmdb.ca/proteins/P31436.xml Arabinose-proton symporter P0AE24 ARAE_ECOLI araE http://ecmdb.ca/proteins/P0AE24.xml L-arabinose transport system permease protein AraH P0AE26 ARAH_ECOLI araH http://ecmdb.ca/proteins/P0AE26.xml Sugar efflux transporter P31122 SOTB_ECOLI sotB http://ecmdb.ca/proteins/P31122.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml L-arabinose-binding periplasmic protein P02924 ARAF_ECOLI araF http://ecmdb.ca/proteins/P02924.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml Adenosine triphosphate + Water + L-Arabinose > ADP + L-Arabinose + Hydrogen ion + Phosphate ABC-2-RXN Adenosine triphosphate + Water + L-Arabinose > ADP + L-Arabinose + Hydrogen ion + Phosphate ABC-2-RXN L-Arabinose <> L-Ribulose R01761 Water + L-Arabinose + Adenosine triphosphate > L-Arabinose + Phosphate + ADP + Hydrogen ion ABC-2-RXN Water + L-Arabinose + Adenosine triphosphate > L-Arabinose + Phosphate + ADP + Hydrogen ion ABC-2-RXN L-Arabinose > L-Ribulose