2.0 2012-05-31 14:31:29 -0600 2015-06-03 17:19:27 -0600 ECMDB20175 M2MDB001022 N-Acetyl-D-galactosamine 6-phosphate N-acetyl-D-galactosamine 6-phosphate is a member of the chemical class known as Hexoses. These are monosaccharides in which the sugar unit is a hexose. 2-Acetamido-2-deoxy-6-O-phosphono-D-galactose N-Acetyl-D-galactosamine 6-phosphoric acid C8H16NO9P 301.1877 301.056267627 N-[(3R,4R,5R,6R)-2,4,5-trihydroxy-6-[(phosphonooxy)methyl]oxan-3-yl]ethanimidic acid N-[(3R,4R,5R,6R)-2,4,5-trihydroxy-6-[(phosphonooxy)methyl]oxan-3-yl]ethanimidic acid [H]C1(O)O[C@]([H])(COP(O)(O)=O)[C@]([H])(O)[C@]([H])(O)[C@@]1([H])N=C(C)O InChI=1S/C8H16NO9P/c1-3(10)9-5-7(12)6(11)4(18-8(5)13)2-17-19(14,15)16/h4-8,11-13H,2H2,1H3,(H,9,10)(H2,14,15,16)/t4-,5-,6+,7-,8?/m1/s1 BRGMHAYQAZFZDJ-KEWYIRBNSA-N Cytoplasm Periplasm logp -2.29 ALOGPS logs -1.12 ALOGPS solubility 2.28e+01 g/l ALOGPS logp -3.2 ChemAxon pka_strongest_acidic 1 ChemAxon pka_strongest_basic 1.61 ChemAxon iupac N-[(3R,4R,5R,6R)-2,4,5-trihydroxy-6-[(phosphonooxy)methyl]oxan-3-yl]ethanimidic acid ChemAxon average_mass 301.1877 ChemAxon mono_mass 301.056267627 ChemAxon smiles [H]C1(O)O[C@]([H])(COP(O)(O)=O)[C@]([H])(O)[C@]([H])(O)[C@@]1([H])N=C(C)O ChemAxon formula C8H16NO9P ChemAxon inchi InChI=1S/C8H16NO9P/c1-3(10)9-5-7(12)6(11)4(18-8(5)13)2-17-19(14,15)16/h4-8,11-13H,2H2,1H3,(H,9,10)(H2,14,15,16)/t4-,5-,6+,7-,8?/m1/s1 ChemAxon inchikey BRGMHAYQAZFZDJ-KEWYIRBNSA-N ChemAxon polar_surface_area 169.27 ChemAxon refractivity 58.42 ChemAxon polarizability 25.43 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 9 ChemAxon donor_count 6 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 Specdb::CMs 1083792 Specdb::EiMs 2376 Specdb::NmrOneD 340908 Specdb::NmrOneD 340909 Specdb::NmrOneD 340910 Specdb::NmrOneD 340911 Specdb::NmrOneD 340912 Specdb::NmrOneD 340913 Specdb::NmrOneD 340914 Specdb::NmrOneD 340915 Specdb::NmrOneD 340916 Specdb::NmrOneD 340917 Specdb::NmrOneD 340918 Specdb::NmrOneD 340919 Specdb::NmrOneD 340920 Specdb::NmrOneD 340921 Specdb::NmrOneD 340922 Specdb::NmrOneD 340923 Specdb::NmrOneD 340924 Specdb::NmrOneD 340925 Specdb::NmrOneD 340926 Specdb::NmrOneD 340927 Specdb::MsMs 29642 Specdb::MsMs 29643 Specdb::MsMs 29644 Specdb::MsMs 36200 Specdb::MsMs 36201 Specdb::MsMs 36202 16019956 13148707 C06376 18207 N-ACETYL-D-GALACTOSAMINE-6-PHOSPHATE 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 N-acetylgalactosamine-specific phosphotransferase enzyme IIB component 2 P42904 PTPB2_ECOLI agaV http://ecmdb.ca/proteins/P42904.xml Putative N-acetylgalactosamine-6-phosphate deacetylase P42906 AGAA_ECOLI agaA http://ecmdb.ca/proteins/P42906.xml N-Acetyl-b-D-galactosamine + Protein N(pi)-phospho-L-histidine <> N-Acetyl-D-galactosamine 6-phosphate + Protein histidine R08366 N-Acetyl-D-galactosamine 6-phosphate + Water > D-Galactosamine 6-phosphate + Acetic acid