2.0 2015-06-08 15:25:34 -0600 2015-08-05 16:22:05 -0600 ECMDB23867 M2MDB005502 Sugar phosphate Any monosaccharide containing an alcoholic hydroxy group esterified with phosphoric acid 2-(4-Hydroxy-3,5-dimethoxycinnamoyloxy)-N,N,N-trimethylethanaminium 2-[[3-(4-Hydroxy-3,5-dimethoxyphenyl)-1-oxo-2-propenyl]oxy]-N,N,N- trimethylethanaminium, 9ci 4-Hydroxy-3,5-dimethoxycinnamate choline 4-Hydroxy-3,5-dimethoxycinnamic acid choline Choline 4-hydroxy-3,5-dimethoxycinnamate, 8ci Choline 4-hydroxy-3,5-dimethoxycinnamic acid, 8ci O-Sinapoylcholine Sinapine bisulfate Sinapine bisulfuric acid Sinapine bisulphate Sinapine bisulphuric acid Sinapoylcholine Sugar phosphoric acid C16H24NO5 310.3655 310.165447883 (2-{[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy}ethyl)trimethylazanium sinapine COC1=CC(\C=C/C(=O)OCC[N+](C)(C)C)=CC(OC)=C1O InChI=1S/C16H23NO5/c1-17(2,3)8-9-22-15(18)7-6-12-10-13(20-4)16(19)14(11-12)21-5/h6-7,10-11H,8-9H2,1-5H3/p+1 HUJXHFRXWWGYQH-UHFFFAOYSA-O logp -0.93 ALOGPS logs -4.39 ALOGPS solubility 1.41e-02 g/l ALOGPS logp -2.2 ChemAxon pka_strongest_acidic 9.29 ChemAxon pka_strongest_basic -4.6 ChemAxon iupac (2-{[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy}ethyl)trimethylazanium ChemAxon average_mass 310.3655 ChemAxon mono_mass 310.165447883 ChemAxon smiles COC1=CC(\C=C/C(=O)OCC[N+](C)(C)C)=CC(OC)=C1O ChemAxon formula C16H24NO5 ChemAxon inchi InChI=1S/C16H23NO5/c1-17(2,3)8-9-22-15(18)7-6-12-10-13(20-4)16(19)14(11-12)21-5/h6-7,10-11H,8-9H2,1-5H3/p+1 ChemAxon inchikey HUJXHFRXWWGYQH-UHFFFAOYSA-O ChemAxon polar_surface_area 64.99 ChemAxon refractivity 96.67 ChemAxon polarizability 34.33 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 4 ChemAxon donor_count 1 ChemAxon physiological_charge 1 ChemAxon formal_charge 1 ChemAxon Pentose phosphate pathway ec00030 Starch and sucrose metabolism The metabolism of starch and sucrose begins with D-fructose interacting with a D-glucose in a reversible reaction through a maltodextrin glucosidase resulting in a water molecule and a sucrose. D-fructose is phosphorylated through an ATP driven fructokinase resulting in the release of an ADP, a hydrogen ion and a Beta-D-fructofuranose 6-phosphate. This compound can also be introduced into the cytoplasm through either a mannose PTS permease or a hexose-6-phosphate:phosphate antiporter. The Beta-D-fructofuranose 6-phosphate is isomerized through a phosphoglucose isomerase resulting in a Beta-D-glucose 6-phosphate. This compound can also be incorporated by glucose PTS permease or a hexose-6-phosphate:phosphate antiporter. The beta-D-glucose 6 phosphate can also be produced by a D-glucose being phosphorylated by an ATP-driven glucokinase resulting in a ADP, a hydrogen ion and a Beta-D-glucose 6 phosphate. The beta-D-glucose can produce alpha-D-glucose-1-phosphate by two methods: 1.-Beta-D-glucose is isomerized into an alpha-D-Glucose 6-phosphate and then interacts in a reversible reaction through a phosphoglucomutase-1 resulting in a alpha-D-glucose-1-phosphate. 2.-Beta-D-glucose interacts with a putative beta-phosphoglucomutase resulting in a Beta-D-glucose 1-phosphate. Beta-D-glucose 1-phosphate can be incorporated into the cytoplasm through a glucose PTS permease. This compound is then isomerized into a Alpha-D-glucose-1-phosphate The beta-D-glucose can cycle back into a D-fructose by first interacting with D-fructose in a reversible reaction through a Polypeptide: predicted glucosyltransferase resulting in the release of a phosphate and a sucrose. The sucrose then interacts in a reversible reaction with a water molecule through a maltodextrin glucosidase resulting in a D-glucose and a D-fructose. Alpha-D-glucose-1-phosphate can produce glycogen in by two different sets of reactions: 1.-Alpha-D-glucose-1-phosphate interacts with a hydrogen ion and an ATP through a glucose-1-phosphate adenylyltransferase resulting in a pyrophosphate and an ADP-glucose. The ADP-glucose then interacts with an amylose through a glycogen synthase resulting in the release of an ADP and an Amylose. The amylose then interacts with 1,4-α-glucan branching enzyme resulting in glycogen 2.- Alpha-D-glucose-1-phosphate interacts with amylose through a maltodextrin phosphorylase resulting in a phosphate and a glycogen. Alpha-D-glucose-1-phosphate can also interacts with UDP-galactose through a galactose-1-phosphate uridylyltransferase resulting in a galactose 1-phosphate and a Uridine diphosphate glucose. The UDP-glucose then interacts with an alpha-D-glucose 6-phosphate through a trehalose-6-phosphate synthase resulting in a uridine 5'-diphosphate, a hydrogen ion and a Trehalose 6- phosphate. The latter compound can also be incorporated into the cytoplasm through a trehalose PTS permease. Trehalose interacts with a water molecule through a trehalose-6-phosphate phosphatase resulting in the release of a phosphate and an alpha,alpha-trehalose.The alpha,alpha-trehalose can also be obtained from glycogen being metabolized through a glycogen debranching enzyme resulting in a the alpha, alpha-trehalose. This compound ca then be hydrated through a cytoplasmic trehalase resulting in the release of an alpha-D-glucose and a beta-d-glucose. Glycogen is then metabolized by reacting with a phosphate through a glycogen phosphorylase resulting in a alpha-D-glucose-1-phosphate and a dextrin. The dextrin is then hydrated through a glycogen phosphorylase-limit dextrin α-1,6-glucohydrolase resulting in the release of a debranched limit dextrin and a maltotetraose. This compound can also be incorporated into the cytoplasm through a maltose ABC transporter. The maltotetraose interacts with a phosphate through a maltodextrin phosphorylase releasing a alpha-D-glucose-1-phosphate and a maltotriose. The maltotriose can also be incorporated through a maltose ABC transporter. The maltotriose can then interact with water through a maltodextrin glucosidase resulting in a D-glucose and a D-maltose. D-maltose can also be incorporated through a maltose ABC transporter The D-maltose can then interact with a maltotriose through a amylomaltase resulting in a maltotetraose and a D-glucose. The D-glucose is then phosphorylated through an ATP driven glucokinase resulting in a hydrogen ion, an ADP and a Beta-D-glucose 6-phosphate PW000941 ec00500 Metabolic Glycolysis / Gluconeogenesis ec00010 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 Ascorbate and aldarate metabolism ec00053 Amino sugar and nucleotide sugar metabolism ec00520 Microbial metabolism in diverse environments ec01120 Phosphotransferase system (PTS) ec02060 Metabolic pathways eco01100 Specdb::CMs 5678 Specdb::CMs 41311 Specdb::CMs 165787 Specdb::NmrOneD 157870 Specdb::NmrOneD 157871 Specdb::NmrOneD 157872 Specdb::NmrOneD 157873 Specdb::NmrOneD 157874 Specdb::NmrOneD 157875 Specdb::NmrOneD 157876 Specdb::NmrOneD 157877 Specdb::NmrOneD 157878 Specdb::NmrOneD 157879 Specdb::NmrOneD 157880 Specdb::NmrOneD 157881 Specdb::NmrOneD 157882 Specdb::NmrOneD 157883 Specdb::NmrOneD 157884 Specdb::NmrOneD 157885 Specdb::NmrOneD 157886 Specdb::NmrOneD 157887 Specdb::NmrOneD 157888 Specdb::NmrOneD 157889 Specdb::MsMs 445199 Specdb::MsMs 445200 Specdb::MsMs 445201 Specdb::MsMs 445447 Specdb::MsMs 445448 Specdb::MsMs 445449 Specdb::MsMs 445450 Specdb::MsMs 445451 Specdb::MsMs 447396 Specdb::MsMs 447397 Specdb::MsMs 447398 Specdb::MsMs 447399 C00934 Sugar phosphatase supH P75792 SUPH_ECOLI supH http://ecmdb.ca/proteins/P75792.xml Protein N(pi)-phospho-L-histidine + Sugar <> Protein histidine + Sugar phosphate R03076 Sugar phosphate + Water + Sugar phosphate <> Sugar + Phosphate + Sugar R00804