2.0 2012-05-31 13:51:45 -0600 2015-06-03 15:54:05 -0600 ECMDB01400 M2MDB000371 Sorbitol-6-phosphate Sorbitol 6-phosphate (Sor6P) is an intermediate in sorbitol biosynthesis. It is a competitive inhibitor for both cytosolic and chloroplastic PGIs with a K(i) of 61 and 40muM, respectively. PMID: 18242768 1-O-Phosphono-D-glucitol 1-O-Phosphono-D-mannitol Alditol 6-phosphate Alditol 6-phosphoric acid D-Glucitol-6-phosphate D-Glucitol-6-phosphoric acid D-Mannitol 1-(dihydrogen phosphate) D-Mannitol 1-(dihydrogen phosphoric acid) D-Mannitol 1-phosphate D-Mannitol 1-phosphoric acid D-Mannitol, 1-(dihydrogenphosphate) D-Mannitol, 1-(dihydrogenphosphoric acid) D-Mannitol-6-phosphate D-Mannitol-6-phosphoric acid D-Sorbitol 6-phosphate D-Sorbitol 6-phosphoric acid Glucitol-6-phosphate Glucitol-6-phosphoric acid Sorbitol 6-phosphate Sorbitol 6-phosphoric acid Sorbitol-6-phosphate Sorbitol-6-phosphoric acid C6H15O9P 262.1517 262.04536859 [(2,3,4,5,6-pentahydroxyhexyl)oxy]phosphonic acid (2,3,4,5,6-pentahydroxyhexyl)oxyphosphonic acid 20479-58-7 OCC(O)C(O)C(O)C(O)COP(O)(O)=O InChI=1S/C6H15O9P/c7-1-3(8)5(10)6(11)4(9)2-15-16(12,13)14/h3-11H,1-2H2,(H2,12,13,14) GACTWZZMVMUKNG-UHFFFAOYSA-N Solid Cytosol logp -2.32 ALOGPS logs -0.99 ALOGPS solubility 2.66e+01 g/l ALOGPS logp -3.9 ChemAxon pka_strongest_acidic 1.49 ChemAxon pka_strongest_basic -3 ChemAxon iupac [(2,3,4,5,6-pentahydroxyhexyl)oxy]phosphonic acid ChemAxon average_mass 262.1517 ChemAxon mono_mass 262.04536859 ChemAxon smiles OCC(O)C(O)C(O)C(O)COP(O)(O)=O ChemAxon formula C6H15O9P ChemAxon inchi InChI=1S/C6H15O9P/c7-1-3(8)5(10)6(11)4(9)2-15-16(12,13)14/h3-11H,1-2H2,(H2,12,13,14) ChemAxon inchikey GACTWZZMVMUKNG-UHFFFAOYSA-N ChemAxon polar_surface_area 167.91 ChemAxon refractivity 49.28 ChemAxon polarizability 21.73 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 8 ChemAxon donor_count 7 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Fructose and mannose metabolism ec00051 Phosphotransferase system (PTS) ec02060 D-sorbitol degradation II Of the six existing hexitols only three (D-mannitol, D-sorbitol [glucitol], and galactitol [owing to symmetry, D- and L-galactitol are identical]) occur naturally and each of these can be utilized by E. coli K-12 as a total source of carbon and energy. Each enters the cell via a specific phosphotransferase system so the first intracellular species is the 6-phospho derivative. D-sorbitol-6-phosphate is converted by a single dehydrogenase reaction to the glycolytic intermediate, D-fructose-6-phosphate and hence flows through the pathways of central metabolism to satisfy the cell's need for precursor metabolites, reducing power, and metabolic energy. PW002022 Metabolic sorbitol degradation II SORBDEG-PWY Specdb::CMs 12537 Specdb::CMs 38908 Specdb::CMs 160100 Specdb::NmrOneD 61172 Specdb::NmrOneD 61173 Specdb::NmrOneD 61174 Specdb::NmrOneD 61175 Specdb::NmrOneD 61176 Specdb::NmrOneD 61177 Specdb::NmrOneD 61178 Specdb::NmrOneD 61179 Specdb::NmrOneD 61180 Specdb::NmrOneD 61181 Specdb::NmrOneD 61182 Specdb::NmrOneD 61183 Specdb::NmrOneD 61184 Specdb::NmrOneD 61185 Specdb::NmrOneD 61186 Specdb::NmrOneD 61187 Specdb::NmrOneD 61188 Specdb::NmrOneD 61189 Specdb::NmrOneD 61190 Specdb::NmrOneD 61191 Specdb::MsMs 28568 Specdb::MsMs 28569 Specdb::MsMs 28570 Specdb::MsMs 35126 Specdb::MsMs 35127 Specdb::MsMs 35128 Specdb::MsMs 2360204 Specdb::MsMs 2360205 Specdb::MsMs 2360206 Specdb::MsMs 2604941 Specdb::MsMs 2604942 Specdb::MsMs 2604943 HMDB05831 618 598 C02810 17044 D-SORBITOL-6-P 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 Zhou, R., Cheng, L. (2008). "Competitive inhibition of phosphoglucose isomerase of apple leaves by sorbitol 6-phosphate." J Plant Physiol 165:903-910. 18242768 PTS system mannitol-specific EIICBA component P00550 PTM3C_ECOLI mtlA http://ecmdb.ca/proteins/P00550.xml Glucitol/sorbitol-specific phosphotransferase enzyme IIA component P05706 PTHA_ECOLI srlB http://ecmdb.ca/proteins/P05706.xml Sorbitol-6-phosphate 2-dehydrogenase P05707 SRLD_ECOLI srlD http://ecmdb.ca/proteins/P05707.xml Phosphoenolpyruvate-protein phosphotransferase P08839 PT1_ECOLI ptsI http://ecmdb.ca/proteins/P08839.xml Mannitol-1-phosphate 5-dehydrogenase P09424 MTLD_ECOLI mtlD http://ecmdb.ca/proteins/P09424.xml Glucitol/sorbitol-specific phosphotransferase enzyme IIB component P56580 PTHB_ECOLI srlE http://ecmdb.ca/proteins/P56580.xml PTS system mannose-specific EIIAB component P69797 PTNAB_ECOLI manX http://ecmdb.ca/proteins/P69797.xml Mannitol-specific cryptic phosphotransferase enzyme IIA component P69824 PTMA_ECOLI cmtB http://ecmdb.ca/proteins/P69824.xml PTS system mannitol-specific cryptic EIICB component P69826 PTMCB_ECOLI cmtA http://ecmdb.ca/proteins/P69826.xml Glucitol/sorbitol permease IIC component P56579 PTHC_ECOLI srlA http://ecmdb.ca/proteins/P56579.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 Phosphocarrier protein HPr P0AA04 PTHP_ECOLI ptsH http://ecmdb.ca/proteins/P0AA04.xml PTS system mannitol-specific EIICBA component P00550 PTM3C_ECOLI mtlA http://ecmdb.ca/proteins/P00550.xml PTS system mannitol-specific cryptic EIICB component P69826 PTMCB_ECOLI cmtA http://ecmdb.ca/proteins/P69826.xml Glucitol/sorbitol permease IIC component P56579 PTHC_ECOLI srlA http://ecmdb.ca/proteins/P56579.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 Phosphoenolpyruvic acid + Sorbitol > Pyruvic acid + Sorbitol-6-phosphate TRANS-RXN-169 Phosphoenolpyruvic acid + Mannitol > Sorbitol-6-phosphate + Pyruvic acid TRANS-RXN-156 NAD + Sorbitol-6-phosphate <> Fructose 6-phosphate + Hydrogen ion + NADH MANNPDEHYDROG-RXN Sorbitol-6-phosphate + NAD <> beta-D-Fructose 6-phosphate + NADH + Hydrogen ion R05607 Protein N(pi)-phospho-L-histidine + Mannitol <> Protein histidine + Sorbitol-6-phosphate R02704 Protein N(pi)-phospho-L-histidine + Sorbitol <> Protein histidine + Sorbitol-6-phosphate R05820 Phosphoenolpyruvic acid + Mannitol > Sorbitol-6-phosphate + Pyruvic acid TRANS-RXN-156 Phosphoenolpyruvic acid + Sorbitol > Sorbitol-6-phosphate + Pyruvic acid TRANS-RXN-169 Sorbitol-6-phosphate + NAD > Fructose 6-phosphate + NADH Sorbitol-6-phosphate + HPr - phosphorylated > HPr PW_RCT000179 Sorbitol-6-phosphate + NAD <> beta-D-Fructose 6-phosphate + NADH + Hydrogen ion