2.0 2012-05-31 13:57:58 -0600 2015-06-03 15:54:20 -0600 ECMDB03174 M2MDB000480 2-Deoxyglucose 2-Deoxyglucose is a glucose molecule that has the 2-hydroxyl group replaced by hydrogen, so that it cannot undergo further glycolysis. It can be used as a glycolysis inhibitor. 2-deoxyglucose is taken up by E. coli and is phosphorylated to 2-deoxyglucose-6P. Glucosamine, mannose and 2-deoxyglucose enter Escherichia coli by the component of the phosphotransferase system coded for by the gene ptsM. 2-Deoxyglucose is an unnatural glucose analog and is not considered a natural E. coli substrate or metabolite. 2-Deoxyglucose is a relatively rare yet natural monosaccharide that can be made from D-glucose, D-aminoglucose and a variety of amino-polysaccharides. 2-Deoxy-D-arabino-hexopyranose 2-Deoxy-D-arabino-hexose 2-Deoxy-D-arabinohexose 2-Deoxy-D-glucose 2-Deoxy-D-mannose 2-deoxyglucose 2-Deoxyhexose 2-Desoxy-D-glucose D-2-Deoxyglucose D-2dGlc D-Arabino-2-Deoxyhexose D-Arabino-Hexose, 2-deoxy- ( ) Deoxyglucose C6H12O5 164.1565 164.068473494 (3R,4S,5R)-3,4,5,6-tetrahydroxyhexanal deoxyglucose 154-17-6 [H]C([H])(C=O)[C@@]([H])(O)[C@]([H])(O)[C@]([H])(O)CO InChI=1S/C6H12O5/c7-2-1-4(9)6(11)5(10)3-8/h2,4-6,8-11H,1,3H2/t4-,5-,6+/m1/s1 VRYALKFFQXWPIH-PBXRRBTRSA-N Solid Cytoplasm Periplasm logp -1.95 ALOGPS logs 0.36 ALOGPS solubility 3.79e+02 g/l ALOGPS melting_point 146.5 oC logp -2.9 ChemAxon pka_strongest_acidic 12.84 ChemAxon pka_strongest_basic -3 ChemAxon iupac (3R,4S,5R)-3,4,5,6-tetrahydroxyhexanal ChemAxon average_mass 164.1565 ChemAxon mono_mass 164.068473494 ChemAxon smiles [H]C([H])(C=O)[C@@]([H])(O)[C@]([H])(O)[C@]([H])(O)CO ChemAxon formula C6H12O5 ChemAxon inchi InChI=1S/C6H12O5/c7-2-1-4(9)6(11)5(10)3-8/h2,4-6,8-11H,1,3H2/t4-,5-,6+/m1/s1 ChemAxon inchikey VRYALKFFQXWPIH-PBXRRBTRSA-N ChemAxon polar_surface_area 97.99 ChemAxon refractivity 36.01 ChemAxon polarizability 15.47 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon inner membrane transport list of inner membrane transport complexes, transporting compounds from the periplasmic space to the cytosol This pathway should be updated regularly with the new inner membrae transports added PW000786 Metabolic Specdb::CMs 1447 Specdb::CMs 1449 Specdb::CMs 2990 Specdb::CMs 32049 Specdb::CMs 32050 Specdb::CMs 48930 Specdb::CMs 130631 Specdb::CMs 138365 Specdb::NmrOneD 67012 Specdb::NmrOneD 67013 Specdb::NmrOneD 67014 Specdb::NmrOneD 67015 Specdb::NmrOneD 67016 Specdb::NmrOneD 67017 Specdb::NmrOneD 67018 Specdb::NmrOneD 67019 Specdb::NmrOneD 67020 Specdb::NmrOneD 67021 Specdb::NmrOneD 67022 Specdb::NmrOneD 67023 Specdb::NmrOneD 67024 Specdb::NmrOneD 67025 Specdb::NmrOneD 67026 Specdb::NmrOneD 67027 Specdb::NmrOneD 67028 Specdb::NmrOneD 67029 Specdb::NmrOneD 67030 Specdb::NmrOneD 67031 Specdb::MsMs 25790 Specdb::MsMs 25791 Specdb::MsMs 25792 Specdb::MsMs 32348 Specdb::MsMs 32349 Specdb::MsMs 32350 Specdb::MsMs 2296364 Specdb::MsMs 2296365 Specdb::MsMs 2296366 Specdb::MsMs 2641948 Specdb::MsMs 2641949 Specdb::MsMs 2641950 97292 C00586 2-DEOXY-D-GLUCOSE 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 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 PTS system mannose-specific EIIAB component P69797 PTNAB_ECOLI manX http://ecmdb.ca/proteins/P69797.xml Mannose permease IIC component P69801 PTNC_ECOLI manY http://ecmdb.ca/proteins/P69801.xml Mannose permease IID component P69805 PTND_ECOLI manZ http://ecmdb.ca/proteins/P69805.xml 2-deoxyglucose-6-P phosphatase P77247 yniC http://ecmdb.ca/proteins/P77247.xml Mannose permease IIC component P69801 PTNC_ECOLI manY http://ecmdb.ca/proteins/P69801.xml Mannose permease IID component P69805 PTND_ECOLI manZ http://ecmdb.ca/proteins/P69805.xml Water + 2-Deoxy-D-glucose 6-phosphate > Phosphate + 2-Deoxyglucose 3.1.3.68-RXN 2-Deoxy-D-glucose 6-phosphate + Water > 2-Deoxyglucose + Inorganic phosphate 2-Deoxyglucose + HPr - phosphorylated > 2-Deoxy-D-glucose 6-phosphate + HPr PW_RCT000178