2.0 2012-05-31 13:59:29 -0600 2015-06-03 15:54:24 -0600 ECMDB03514 M2MDB000508 alpha-D-Glucose 1,6-bisphosphate Alpha-D-glucose 1,6-bisphosphate is considered to be a major regulator of carbohydrate metabolism. Glucose 1,6-diphosphate (G 1,6-P2) have been recognized as a regulatory signal implicated in the control of metabolism, oxygen affinity of red cells and other cellular functions. G 1,6-P2 is a potent allosteric activator of phosphofructokinase. &alpha;-D-glucopyranose, 1,6-bis(dihydrogen phosphate) &alpha;-D-glucopyranose, 1,6-bis(dihydrogen phosphoric acid) &alpha;-D-glucose-1,6-P2 &alpha;-D-glucose-1,6-P<SUB>2</SUB> a-D-1,6-Bis(dihydrogen phosphate) glucopyranose a-D-1,6-Bis(dihydrogen phosphoric acid) glucopyranose a-D-Glucopyranose, 1,6-bis(dihydrogen phosphate) a-D-Glucopyranose, 1,6-bis(dihydrogen phosphoric acid) A-D-Glucose 1,6-bis(dihydrogen phosphate) a-D-Glucose 1,6-bis(dihydrogen phosphoric acid) A-D-Glucose 1,6-bisphosphate a-D-Glucose 1,6-bisphosphoric acid A-D-Glucose 1,6-diphosphate a-D-Glucose 1,6-diphosphoric acid a-D-Glucose-1,6-P2 a-delta-1,6-Bis(dihydrogen phosphate) glucopyranose a-delta-1,6-Bis(dihydrogen phosphoric acid) glucopyranose a-delta-Glucose 1,6-bis(dihydrogen phosphate) a-delta-Glucose 1,6-bis(dihydrogen phosphoric acid) a-delta-Glucose 1,6-bisphosphate a-delta-Glucose 1,6-bisphosphoric acid a-delta-Glucose 1,6-diphosphate a-delta-Glucose 1,6-diphosphoric acid a-δ-1,6-Bis(dihydrogen phosphate) glucopyranose a-δ-1,6-Bis(dihydrogen phosphoric acid) glucopyranose a-δ-Glucose 1,6-bis(dihydrogen phosphate) a-δ-Glucose 1,6-bis(dihydrogen phosphoric acid) a-δ-Glucose 1,6-bisphosphate a-δ-Glucose 1,6-bisphosphoric acid a-δ-Glucose 1,6-diphosphate a-δ-Glucose 1,6-diphosphoric acid Alpha-D-1,6-Bis(dihydrogen phosphate) Glucopyranose alpha-D-1,6-Bis(dihydrogen phosphoric acid) glucopyranose Alpha-D-Glucopyranose, 1,6-bis(dihydrogen phosphate) alpha-D-Glucopyranose, 1,6-bis(dihydrogen phosphoric acid) Alpha-D-Glucose 1,6-bis(dihydrogen phosphate) alpha-D-Glucose 1,6-bis(dihydrogen phosphoric acid) Alpha-D-Glucose 1,6-bisphosphate alpha-D-Glucose 1,6-bisphosphoric acid Alpha-D-Glucose 1,6-diphosphate alpha-D-Glucose 1,6-diphosphoric acid Alpha-D-Glucose-1,6-P2 Alpha-delta-1,6-Bis(dihydrogen phosphate) Glucopyranose alpha-delta-1,6-Bis(dihydrogen phosphoric acid) glucopyranose Alpha-delta-Glucose 1,6-bis(dihydrogen phosphate) alpha-delta-Glucose 1,6-bis(dihydrogen phosphoric acid) Alpha-delta-Glucose 1,6-bisphosphate alpha-delta-Glucose 1,6-bisphosphoric acid Alpha-delta-Glucose 1,6-diphosphate alpha-delta-Glucose 1,6-diphosphoric acid D-Glucose 1,6-biphosphate D-Glucose 1,6-biphosphoric acid D-Glucose 1,6-bisphosphate D-Glucose 1,6-bisphosphoric acid D-Glucose 1,6-diphosphate D-Glucose 1,6-diphosphoric acid Delta-Glucose 1,6-diphosphate delta-Glucose 1,6-diphosphoric acid Glucose 1,6-bisphosphate Glucose 1,6-bisphosphoric acid Glucose 1,6-diphosphate Glucose 1,6-diphosphoric acid Glucose-1,6-bisphosphate Glucose-1,6-bisphosphoric acid Glucose-1,6-diphosphate Glucose-1,6-diphosphoric acid α-D-1,6-Bis(dihydrogen phosphate) glucopyranose α-D-1,6-Bis(dihydrogen phosphoric acid) glucopyranose α-D-Glucopyranose, 1,6-bis(dihydrogen phosphate) α-D-Glucopyranose, 1,6-bis(dihydrogen phosphoric acid) α-D-Glucose 1,6-bis(dihydrogen phosphate) α-D-Glucose 1,6-bis(dihydrogen phosphoric acid) α-D-Glucose 1,6-bisphosphate α-D-Glucose 1,6-bisphosphoric acid α-D-Glucose 1,6-diphosphate α-D-Glucose 1,6-diphosphoric acid α-D-Glucose-1,6-P2 α-δ-1,6-Bis(dihydrogen phosphate) glucopyranose α-δ-1,6-Bis(dihydrogen phosphoric acid) glucopyranose α-δ-Glucose 1,6-bis(dihydrogen phosphate) α-δ-Glucose 1,6-bis(dihydrogen phosphoric acid) α-δ-Glucose 1,6-bisphosphate α-δ-Glucose 1,6-bisphosphoric acid α-δ-Glucose 1,6-diphosphate α-δ-Glucose 1,6-diphosphoric acid δ-Glucose 1,6-diphosphate δ-Glucose 1,6-diphosphoric acid C6H14O12P2 340.1157 339.996048936 {[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[(phosphonooxy)methyl]oxan-2-yl]oxy}phosphonic acid [(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[(phosphonooxy)methyl]oxan-2-yl]oxyphosphonic acid 10139-18-1 O[C@H]1[C@H](O)[C@@H](COP(O)(O)=O)O[C@H](OP(O)(O)=O)[C@@H]1O InChI=1S/C6H14O12P2/c7-3-2(1-16-19(10,11)12)17-6(5(9)4(3)8)18-20(13,14)15/h2-9H,1H2,(H2,10,11,12)(H2,13,14,15)/t2-,3-,4+,5-,6-/m1/s1 RWHOZGRAXYWRNX-VFUOTHLCSA-N Solid Cytoplasm Periplasm logp -1.65 ALOGPS logs -1.33 ALOGPS solubility 1.60e+01 g/l ALOGPS logp -3.2 ChemAxon pka_strongest_acidic 0.89 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac {[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[(phosphonooxy)methyl]oxan-2-yl]oxy}phosphonic acid ChemAxon average_mass 340.1157 ChemAxon mono_mass 339.996048936 ChemAxon smiles O[C@H]1[C@H](O)[C@@H](COP(O)(O)=O)O[C@H](OP(O)(O)=O)[C@@H]1O ChemAxon formula C6H14O12P2 ChemAxon inchi InChI=1S/C6H14O12P2/c7-3-2(1-16-19(10,11)12)17-6(5(9)4(3)8)18-20(13,14)15/h2-9H,1H2,(H2,10,11,12)(H2,13,14,15)/t2-,3-,4+,5-,6-/m1/s1 ChemAxon inchikey RWHOZGRAXYWRNX-VFUOTHLCSA-N ChemAxon polar_surface_area 203.44 ChemAxon refractivity 57.67 ChemAxon polarizability 24.96 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 10 ChemAxon donor_count 7 ChemAxon physiological_charge -4 ChemAxon formal_charge 0 ChemAxon 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 Specdb::CMs 2933 Specdb::CMs 38617 Specdb::CMs 134252 Specdb::CMs 141986 Specdb::NmrOneD 5151 Specdb::NmrOneD 5152 Specdb::NmrOneD 28082 Specdb::NmrOneD 28083 Specdb::NmrOneD 28084 Specdb::NmrOneD 28085 Specdb::NmrOneD 28086 Specdb::NmrOneD 28087 Specdb::NmrOneD 28088 Specdb::NmrOneD 28089 Specdb::NmrOneD 28090 Specdb::NmrOneD 28091 Specdb::NmrOneD 28092 Specdb::NmrOneD 28093 Specdb::NmrOneD 28094 Specdb::NmrOneD 28095 Specdb::NmrOneD 28096 Specdb::NmrOneD 28097 Specdb::NmrOneD 28098 Specdb::NmrOneD 28099 Specdb::NmrOneD 28100 Specdb::NmrOneD 28101 Specdb::MsMs 29021 Specdb::MsMs 29022 Specdb::MsMs 29023 Specdb::MsMs 35579 Specdb::MsMs 35580 Specdb::MsMs 35581 Specdb::MsMs 439125 Specdb::MsMs 1473419 Specdb::MsMs 1473420 Specdb::MsMs 1475442 Specdb::MsMs 1475443 Specdb::MsMs 1475444 Specdb::MsMs 1475445 Specdb::MsMs 1475446 Specdb::MsMs 1475447 Specdb::MsMs 1475448 Specdb::MsMs 1475449 Specdb::MsMs 1475450 Specdb::MsMs 1475451 Specdb::MsMs 1475452 Specdb::MsMs 1475453 Specdb::MsMs 1475454 Specdb::MsMs 1475455 Specdb::MsMs 1475456 Specdb::MsMs 1475457 HMDB03514 82400 74362 C01231 18148 ALPHA-GLUCOSE-16-BISPHOSPHATE G16 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 Yamada Y, Kono N, Nakajima H, Shimizu T, Kiyokawa H, Kawachi M, Ono A, Nishimura T, Kuwajima M, Tarui S: Low glucose-1, 6-bisphosphate and high fructose-2, 6-bisphosphate concentrations in muscles of patients with glycogenosis types VII and V. Biochem Biophys Res Commun. 1991 Apr 15;176(1):7-10. 2018547 Cadefau JA, Andres V, Carreras J, Vernet M, Grau JM, Urbano-Marquez A, Cusso R: Glucose 1,6-bisphosphate and fructose 2,6-bisphosphate in muscle from healthy humans and chronic alcoholic patients. Alcohol Alcohol. 1992 May;27(3):253-6. 1449560 Katz A, Sahlin K, Broberg S: Regulation of glucose utilization in human skeletal muscle during moderate dynamic exercise. Am J Physiol. 1991 Mar;260(3 Pt 1):E411-5. 2003594 Katz A: G-1,6-P2, glycolysis, and energy metabolism during circulatory occlusion in human skeletal muscle. Am J Physiol. 1988 Aug;255(2 Pt 1):C140-4. 3407759 Glucose-1-phosphate adenylyltransferase P0A6V1 GLGC_ECOLI glgC http://ecmdb.ca/proteins/P0A6V1.xml Phosphoglucosamine mutase P31120 GLMM_ECOLI glmM http://ecmdb.ca/proteins/P31120.xml