2.0 2012-05-31 10:24:52 -0600 2015-09-13 12:56:07 -0600 ECMDB00247 M2MDB000105 Sorbitol Sorbitol, also known as glucitol, is a sugar alcohol. It is obtained by reduction of glucose changing the aldehyde group to an additional hydroxyl group. Sorbitol is a polyhydric alcohol with about half the sweetness of sucrose. It occurs naturally and is also produced synthetically from glucose. (-)-Sorbitol Cystosol D-Glucitol D-Sorbitol D-Sorbol Diakarmon Esasorb Foodol D 70 Glucarine Glucitol Iso-sorbide Karion Karion instant Kyowa Powder 50M L-Gulitol Meglumine Multitol Neosorb Neosorb 20/60DC Neosorb 70/02 Neosorb 70/70 Neosorb P 20/60 Neosorb P 60 Neosorb P 60W Nivitin Resulax Sionit Sionit K Sionite Sionon Siosan Sorbex M Sorbex R Sorbex Rp Sorbex S Sorbex X Sorbilande Sorbilax Sorbit Sorbit D 70 Sorbit D-Powder Sorbit DP Sorbit DP 50 Sorbit Kyowa Powder 50M Sorbit L 70 Sorbit S Sorbit T 70 Sorbit W 70 Sorbit W-Powder Sorbit W-Powder 50 Sorbit WP Sorbite Sorbitol Sorbitol F Sorbitol FK Sorbitol FP Sorbitol S Sorbitol syrup C Sorbitur Sorbo Sorbogem 712 Sorbol Sorbostyl C6H14O6 182.1718 182.07903818 (2R,3R,4R,5S)-hexane-1,2,3,4,5,6-hexol D-sorbitol 50-70-4 OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO InChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4+,5-,6-/m1/s1 FBPFZTCFMRRESA-JGWLITMVSA-N Liquid Extra-organism Periplasm logp -2.68 ALOGPS logs 0.10 ALOGPS solubility 2.29e+02 g/l ALOGPS melting_point 11 oC logp -3.7 ChemAxon pka_strongest_acidic 12.59 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2R,3R,4R,5S)-hexane-1,2,3,4,5,6-hexol ChemAxon average_mass 182.1718 ChemAxon mono_mass 182.07903818 ChemAxon smiles OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO ChemAxon formula C6H14O6 ChemAxon inchi InChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4+,5-,6-/m1/s1 ChemAxon inchikey FBPFZTCFMRRESA-JGWLITMVSA-N ChemAxon polar_surface_area 121.38 ChemAxon refractivity 38.4 ChemAxon polarizability 17.12 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 6 ChemAxon donor_count 6 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Fructose and mannose metabolism ec00051 Galactose metabolism Galactose can be synthesized through two pathways: melibiose degradation involving an alpha galactosidase and lactose degradation involving a beta galactosidase. Melibiose is first transported inside the cell through the melibiose:Li+/Na+/H+ symporter. Once inside the cell, melibiose is degraded through alpha galactosidase into an alpha-D-galactose and a beta-D-glucose. The beta-D-glucose is phosphorylated by a glucokinase to produce a beta-D-glucose-6-phosphate which can spontaneously be turned into a alpha D glucose 6 phosphate. This alpha D-glucose-6-phosphate is metabolized into a glucose -1-phosphate through a phosphoglucomutase-1. The glucose -1-phosphate is transformed into a uridine diphosphate glucose through UTP--glucose-1-phosphate uridylyltransferase. The product, uridine diphosphate glucose, can undergo a reversible reaction in which it can be turned into uridine diphosphategalactose through an UDP-glucose 4-epimerase. Galactose can also be produced by lactose degradation involving a lactose permease to uptake lactose from the environment and a beta-galactosidase to turn lactose into Beta-D-galactose. Beta-D-galactose can also be uptaken from the environment through a galactose proton symporter. Galactose is degraded through the following process: Beta-D-galactose is introduced into the cytoplasm through a galactose proton symporter, or it can be synthesized from an alpha lactose that is introduced into the cytoplasm through a lactose permease. Alpha lactose interacts with water through a beta-galactosidase resulting in a beta-D-glucose and beta-D-galactose. Beta-D-galactose is isomerized into D-galactose. D-Galactose undergoes phosphorylation through a galactokinase, hence producing galactose 1 phosphate. On the other side of the pathway, a gluose-1-phosphate (product of the interaction of alpha-D-glucose 6-phosphate with a phosphoglucomutase resulting in a alpha-D-glucose-1-phosphate, an isomer of Glucose 1-phosphate, or an isomer of Beta-D-glucose 1-phosphate) interacts with UTP and a hydrogen ion in order to produce a uridine diphosphate glucose. This is followed by the interaction of galactose-1-phosphate with an established amount of uridine diphosphate glucose through a galactose-1-phosphate uridylyltransferase, which in turn output a glucose-1-phosphate and a uridine diphosphate galactose. The glucose -1-phosphate is transformed into a uridine diphosphate glucose through UTP--glucose-1-phosphate uridylyltransferase. The product, uridine diphosphate glucose, can undergo a reversible reaction in which it can be turned into uridine diphosphategalactose through an UDP-glucose 4-epimerase, and so the cycle can keep going as long as more lactose or galactose is imported into the cell PW000821 ec00052 Metabolic Phosphotransferase system (PTS) ec02060 ABC transporters ec02010 Specdb::CMs 486 Specdb::CMs 1651 Specdb::CMs 2338 Specdb::CMs 30531 Specdb::CMs 31102 Specdb::CMs 32318 Specdb::CMs 37385 Specdb::CMs 167112 Specdb::CMs 1055333 Specdb::CMs 1055334 Specdb::CMs 1055336 Specdb::CMs 1055338 Specdb::CMs 1055340 Specdb::CMs 1055342 Specdb::CMs 1055344 Specdb::CMs 1055346 Specdb::CMs 1055347 Specdb::CMs 1055349 Specdb::CMs 1055351 Specdb::CMs 1055353 Specdb::CMs 1055354 Specdb::CMs 1055356 Specdb::CMs 1055358 Specdb::CMs 1055360 Specdb::CMs 1055362 Specdb::NmrOneD 1216 Specdb::NmrOneD 1273 Specdb::NmrOneD 4929 Specdb::NmrOneD 6252 Specdb::NmrOneD 6253 Specdb::NmrOneD 6254 Specdb::NmrOneD 6255 Specdb::NmrOneD 6256 Specdb::NmrOneD 6257 Specdb::NmrOneD 6258 Specdb::NmrOneD 6259 Specdb::NmrOneD 6260 Specdb::NmrOneD 6261 Specdb::NmrOneD 6262 Specdb::NmrOneD 6263 Specdb::NmrOneD 6264 Specdb::NmrOneD 6265 Specdb::NmrOneD 6266 Specdb::NmrOneD 6267 Specdb::NmrOneD 6268 Specdb::NmrOneD 6269 Specdb::NmrOneD 6270 Specdb::NmrOneD 6271 Specdb::NmrOneD 166528 Specdb::MsMs 421 Specdb::MsMs 422 Specdb::MsMs 423 Specdb::MsMs 177957 Specdb::MsMs 177958 Specdb::MsMs 177959 Specdb::MsMs 180270 Specdb::MsMs 180271 Specdb::MsMs 180272 Specdb::MsMs 439783 Specdb::MsMs 439784 Specdb::MsMs 447483 Specdb::MsMs 449938 Specdb::MsMs 449939 Specdb::MsMs 449940 Specdb::MsMs 449941 Specdb::MsMs 449942 Specdb::MsMs 449943 Specdb::MsMs 449944 Specdb::MsMs 449945 Specdb::MsMs 2236749 Specdb::MsMs 2239864 Specdb::MsMs 2241833 Specdb::MsMs 2777195 Specdb::MsMs 2777196 Specdb::NmrTwoD 1236 HMDB00247 5780 5576 C00794 SORBITOL SOR Sorbitol Keseler, I. 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Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 8pp. http://hmdb.ca/system/metabolites/msds/000/000/181/original/HMDB00247.pdf?1358895848 Glucitol/sorbitol-specific phosphotransferase enzyme IIA component P05706 PTHA_ECOLI srlB http://ecmdb.ca/proteins/P05706.xml Alpha-galactosidase P06720 AGAL_ECOLI melA http://ecmdb.ca/proteins/P06720.xml Phosphoenolpyruvate-protein phosphotransferase P08839 PT1_ECOLI ptsI http://ecmdb.ca/proteins/P08839.xml Glucitol/sorbitol-specific phosphotransferase enzyme IIB component P56580 PTHB_ECOLI srlE http://ecmdb.ca/proteins/P56580.xml Glucitol/sorbitol permease IIC component P56579 PTHC_ECOLI srlA http://ecmdb.ca/proteins/P56579.xml Phosphocarrier protein HPr P0AA04 PTHP_ECOLI ptsH http://ecmdb.ca/proteins/P0AA04.xml Glucitol/sorbitol permease IIC component P56579 PTHC_ECOLI srlA http://ecmdb.ca/proteins/P56579.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 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 Phosphoenolpyruvic acid + Sorbitol > Pyruvic acid + Sorbitol-6-phosphate TRANS-RXN-169 Melibiitol + Water <> Sorbitol + D-Galactose R02926 Protein N(pi)-phospho-L-histidine + Sorbitol <> Protein histidine + Sorbitol-6-phosphate R05820 Phosphoenolpyruvic acid + Sorbitol > Sorbitol-6-phosphate + Pyruvic acid TRANS-RXN-169