2.02012-05-31 13:51:45 -06002015-06-03 15:54:05 -0600ECMDB01400M2MDB000371Sorbitol-6-phosphateSorbitol 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: 182427681-O-Phosphono-D-glucitol1-O-Phosphono-D-mannitolAlditol 6-phosphateAlditol 6-phosphoric acidD-Glucitol-6-phosphateD-Glucitol-6-phosphoric acidD-Mannitol 1-(dihydrogen phosphate)D-Mannitol 1-(dihydrogen phosphoric acid)D-Mannitol 1-phosphateD-Mannitol 1-phosphoric acidD-Mannitol, 1-(dihydrogenphosphate)D-Mannitol, 1-(dihydrogenphosphoric acid)D-Mannitol-6-phosphateD-Mannitol-6-phosphoric acidD-Sorbitol 6-phosphateD-Sorbitol 6-phosphoric acidGlucitol-6-phosphateGlucitol-6-phosphoric acidSorbitol 6-phosphateSorbitol 6-phosphoric acidSorbitol-6-phosphateSorbitol-6-phosphoric acidC6H15O9P262.1517262.04536859[(2,3,4,5,6-pentahydroxyhexyl)oxy]phosphonic acid(2,3,4,5,6-pentahydroxyhexyl)oxyphosphonic acid20479-58-7OCC(O)C(O)C(O)C(O)COP(O)(O)=OInChI=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-NSolidCytosollogp-2.32logs-0.99solubility2.66e+01 g/llogp-3.9pka_strongest_acidic1.49pka_strongest_basic-3iupac[(2,3,4,5,6-pentahydroxyhexyl)oxy]phosphonic acidaverage_mass262.1517mono_mass262.04536859smilesOCC(O)C(O)C(O)C(O)COP(O)(O)=OformulaC6H15O9PinchiInChI=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)inchikeyGACTWZZMVMUKNG-UHFFFAOYSA-Npolar_surface_area167.91refractivity49.28polarizability21.73rotatable_bond_count7acceptor_count8donor_count7physiological_charge-2formal_charge0Fructose and mannose metabolismec00051Phosphotransferase system (PTS)ec02060D-sorbitol degradation IIOf 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.PW002022Metabolicsorbitol degradation IISORBDEG-PWYSpecdb::CMs12537Specdb::CMs38908Specdb::CMs160100Specdb::NmrOneD61172Specdb::NmrOneD61173Specdb::NmrOneD61174Specdb::NmrOneD61175Specdb::NmrOneD61176Specdb::NmrOneD61177Specdb::NmrOneD61178Specdb::NmrOneD61179Specdb::NmrOneD61180Specdb::NmrOneD61181Specdb::NmrOneD61182Specdb::NmrOneD61183Specdb::NmrOneD61184Specdb::NmrOneD61185Specdb::NmrOneD61186Specdb::NmrOneD61187Specdb::NmrOneD61188Specdb::NmrOneD61189Specdb::NmrOneD61190Specdb::NmrOneD61191Specdb::MsMs28568Specdb::MsMs28569Specdb::MsMs28570Specdb::MsMs35126Specdb::MsMs35127Specdb::MsMs35128Specdb::MsMs2360204Specdb::MsMs2360205Specdb::MsMs2360206Specdb::MsMs2604941Specdb::MsMs2604942Specdb::MsMs2604943HMDB05831618598C0281017044D-SORBITOL-6-PKeseler, 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-D590.21097882Kanehisa, 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-D114.22080510van 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 370:17-25.17765195Zhou, R., Cheng, L. (2008). "Competitive inhibition of phosphoglucose isomerase of apple leaves by sorbitol 6-phosphate." J Plant Physiol 165:903-910.18242768PTS system mannitol-specific EIICBA componentP00550PTM3C_ECOLImtlAhttp://ecmdb.ca/proteins/P00550.xmlGlucitol/sorbitol-specific phosphotransferase enzyme IIA componentP05706PTHA_ECOLIsrlBhttp://ecmdb.ca/proteins/P05706.xmlSorbitol-6-phosphate 2-dehydrogenaseP05707SRLD_ECOLIsrlDhttp://ecmdb.ca/proteins/P05707.xmlPhosphoenolpyruvate-protein phosphotransferaseP08839PT1_ECOLIptsIhttp://ecmdb.ca/proteins/P08839.xmlMannitol-1-phosphate 5-dehydrogenaseP09424MTLD_ECOLImtlDhttp://ecmdb.ca/proteins/P09424.xmlGlucitol/sorbitol-specific phosphotransferase enzyme IIB componentP56580PTHB_ECOLIsrlEhttp://ecmdb.ca/proteins/P56580.xmlPTS system mannose-specific EIIAB componentP69797PTNAB_ECOLImanXhttp://ecmdb.ca/proteins/P69797.xmlMannitol-specific cryptic phosphotransferase enzyme IIA componentP69824PTMA_ECOLIcmtBhttp://ecmdb.ca/proteins/P69824.xmlPTS system mannitol-specific cryptic EIICB componentP69826PTMCB_ECOLIcmtAhttp://ecmdb.ca/proteins/P69826.xmlGlucitol/sorbitol permease IIC componentP56579PTHC_ECOLIsrlAhttp://ecmdb.ca/proteins/P56579.xmlMannose permease IIC componentP69801PTNC_ECOLImanYhttp://ecmdb.ca/proteins/P69801.xmlMannose permease IID componentP69805PTND_ECOLImanZhttp://ecmdb.ca/proteins/P69805.xmlPhosphocarrier protein HPrP0AA04PTHP_ECOLIptsHhttp://ecmdb.ca/proteins/P0AA04.xmlPTS system mannitol-specific EIICBA componentP00550PTM3C_ECOLImtlAhttp://ecmdb.ca/proteins/P00550.xmlPTS system mannitol-specific cryptic EIICB componentP69826PTMCB_ECOLIcmtAhttp://ecmdb.ca/proteins/P69826.xmlGlucitol/sorbitol permease IIC componentP56579PTHC_ECOLIsrlAhttp://ecmdb.ca/proteins/P56579.xmlMannose permease IIC componentP69801PTNC_ECOLImanYhttp://ecmdb.ca/proteins/P69801.xmlMannose permease IID componentP69805PTND_ECOLImanZhttp://ecmdb.ca/proteins/P69805.xmlPhosphoenolpyruvic acid + Sorbitol > Pyruvic acid + Sorbitol-6-phosphateTRANS-RXN-169Phosphoenolpyruvic acid + Mannitol > Sorbitol-6-phosphate + Pyruvic acidTRANS-RXN-156NAD + Sorbitol-6-phosphate <> Fructose 6-phosphate + Hydrogen ion + NADHMANNPDEHYDROG-RXNSorbitol-6-phosphate + NAD <> beta-D-Fructose 6-phosphate + NADH + Hydrogen ionR05607Protein N(pi)-phospho-L-histidine + Mannitol <> Protein histidine + Sorbitol-6-phosphateR02704Protein N(pi)-phospho-L-histidine + Sorbitol <> Protein histidine + Sorbitol-6-phosphateR05820Phosphoenolpyruvic acid + Mannitol > Sorbitol-6-phosphate + Pyruvic acidTRANS-RXN-156Phosphoenolpyruvic acid + Sorbitol > Sorbitol-6-phosphate + Pyruvic acidTRANS-RXN-169Sorbitol-6-phosphate + NAD > Fructose 6-phosphate + NADHSorbitol-6-phosphate + HPr - phosphorylated > HPrPW_RCT000179Sorbitol-6-phosphate + NAD <> beta-D-Fructose 6-phosphate + NADH + Hydrogen ion