2.0 2012-05-31 14:30:03 -0600 2015-06-03 17:19:24 -0600 ECMDB20149 M2MDB000996 Galactitol 1-phosphate Galactitol 1-phosphate is a member of the chemical class known as Hexoses. These are monosaccharides in which the sugar unit is a hexose. 1-O-Phosphono-D-galactitol D-Galactitol 1-(dihydrogen phosphate) D-Galactitol 1-(dihydrogen phosphoric acid) D-Galactitol 1-phosphate D-Galactitol 1-phosphoric acid Galactitol 1-phosphoric acid Galactitol-1-phosphate Galactitol-1-phosphoric acid Galactitol1P L-Galactitol 6-phosphate L-Galactitol 6-phosphoric acid C6H15O9P 262.1517 262.04536859 {[(2S,3R,4S,5R)-2,3,4,5,6-pentahydroxyhexyl]oxy}phosphonic acid galactitol 1-phosphate 15664-55-8 [H][C@@](O)(CO)[C@]([H])(O)[C@]([H])(O)[C@@]([H])(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)/t3-,4+,5+,6-/m1/s1 GACTWZZMVMUKNG-DPYQTVNSSA-N 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 {[(2S,3R,4S,5R)-2,3,4,5,6-pentahydroxyhexyl]oxy}phosphonic acid ChemAxon average_mass 262.1517 ChemAxon mono_mass 262.04536859 ChemAxon smiles [H][C@@](O)(CO)[C@]([H])(O)[C@]([H])(O)[C@@]([H])(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)/t3-,4+,5+,6-/m1/s1 ChemAxon inchikey GACTWZZMVMUKNG-DPYQTVNSSA-N ChemAxon polar_surface_area 167.91 ChemAxon refractivity 49.28 ChemAxon polarizability 21.61 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 8 ChemAxon donor_count 7 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon 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 Metabolic pathways eco01100 galactitol degradation GALACTITOLCAT-PWY Specdb::CMs 1083329 Specdb::NmrOneD 314601 Specdb::NmrOneD 314602 Specdb::NmrOneD 314603 Specdb::NmrOneD 314604 Specdb::NmrOneD 314605 Specdb::NmrOneD 314606 Specdb::NmrOneD 314607 Specdb::NmrOneD 314608 Specdb::NmrOneD 314609 Specdb::NmrOneD 314610 Specdb::NmrOneD 314611 Specdb::NmrOneD 314612 Specdb::NmrOneD 314613 Specdb::NmrOneD 314614 Specdb::NmrOneD 314615 Specdb::NmrOneD 314616 Specdb::NmrOneD 314617 Specdb::NmrOneD 314618 Specdb::NmrOneD 314619 Specdb::NmrOneD 314620 Specdb::MsMs 23024 Specdb::MsMs 23025 Specdb::MsMs 23026 Specdb::MsMs 29822 Specdb::MsMs 29823 Specdb::MsMs 29824 440969 389796 C06311 28663 GALACTITOL-1-PHOSPHATE 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 Phosphoenolpyruvate-protein phosphotransferase P08839 PT1_ECOLI ptsI http://ecmdb.ca/proteins/P08839.xml Galactitol-1-phosphate 5-dehydrogenase P0A9S3 GATD_ECOLI gatD http://ecmdb.ca/proteins/P0A9S3.xml Galactitol-specific phosphotransferase enzyme IIB component P37188 PTKB_ECOLI gatB http://ecmdb.ca/proteins/P37188.xml Putative phosphotransferase IIA component sgcA P39363 SGCA_ECOLI sgcA http://ecmdb.ca/proteins/P39363.xml Putative phosphotransferase enzyme IIB component sgcB P58035 SGCB_ECOLI sgcB http://ecmdb.ca/proteins/P58035.xml Galactitol-specific phosphotransferase enzyme IIA component P69828 PTKA_ECOLI gatA http://ecmdb.ca/proteins/P69828.xml Putative permease IIC component P39365 SGCC_ECOLI sgcC http://ecmdb.ca/proteins/P39365.xml Galactitol permease IIC component P69831 PTKC_ECOLI gatC http://ecmdb.ca/proteins/P69831.xml Phosphocarrier protein HPr P0AA04 PTHP_ECOLI ptsH http://ecmdb.ca/proteins/P0AA04.xml Galactitol permease IIC component P69831 PTKC_ECOLI gatC http://ecmdb.ca/proteins/P69831.xml Phosphoenolpyruvic acid + Galactitol > Galactitol 1-phosphate + Pyruvic acid TRANS-RXN-161 Galactitol 1-phosphate + NAD <> Hydrogen ion + NADH + D-Tagatose 6-phosphate R05571 GALACTITOLPDEHYD-RXN Galactitol + Protein N(pi)-phospho-L-histidine <> Galactitol 1-phosphate + Protein histidine R05570 Phosphoenolpyruvic acid + Galactitol > Galactitol 1-phosphate + Pyruvic acid TRANS-RXN-161 Galactitol 1-phosphate + NAD > L-Tagatose-6-phosphate + NADH NAD + Galactitol 1-phosphate <> L-Tagatose-6-phosphate + NADH + Hydrogen ion R05147 Galactitol + Protein N(pi)-phospho-L-histidine <> Galactitol 1-phosphate + Protein histidine Galactitol + Protein N(pi)-phospho-L-histidine <> Galactitol 1-phosphate + Protein histidine