2.0 2012-05-31 14:05:56 -0600 2015-06-03 15:54:46 -0600 ECMDB04129 M2MDB000626 2-Phospho-D-glyceric acid 2-Phospho-D-glycerate or 2PG is an intermediate in gluconeogenesis. It is a glyceric acid which serves as the substrate in the ninth step of glycolysis. 2PG is converted by enolase into phosphoenolpyruvate (PEP), the penultimate step in the conversion of glucose to pyruvate. More specifically, 2PG can be generated from Glycerate-3-phosphate via phosphoglycerate mutase or from phosphoenolpyrvate via alpha enolase. (2R)-3-hydroxy-2-(phosphonooxy)propanoate (2R)-3-hydroxy-2-(phosphonooxy)propanoic acid 2-P-D-Glycerate 2-P-D-Glyceric acid 2-PG 2-Phospho-(D)-glycerate 2-Phospho-(D)-glyceric acid 2-Phospho-(R)-glycerate 2-Phospho-(R)-glyceric acid 2-Phospho-D-glycerate 2-Phospho-D-glyceric acid 3-D-Hydroxy-2-phosphonooxy-propanoate 3-D-Hydroxy-2-phosphonooxy-propanoic acid D-2-Phosphoglycerate D-2-Phosphoglyceric acid D-Glycerate 2-phosphate D-Glyceric acid 2-phosphate D-Glyceric acid 2-phosphoric acid C3H7O7P 186.0572 185.99293909 (2R)-3-hydroxy-2-(phosphonooxy)propanoic acid (+-)-2-phosphoglycerate OC[C@@H](OP(O)(O)=O)C(O)=O InChI=1S/C3H7O7P/c4-1-2(3(5)6)10-11(7,8)9/h2,4H,1H2,(H,5,6)(H2,7,8,9)/t2-/m1/s1 GXIURPTVHJPJLF-UWTATZPHSA-N Solid Cytosol logp -2.24 ALOGPS logs -0.96 ALOGPS solubility 2.03e+01 g/l ALOGPS logp -1.6 ChemAxon pka_strongest_acidic 0.81 ChemAxon pka_strongest_basic -3.1 ChemAxon iupac (2R)-3-hydroxy-2-(phosphonooxy)propanoic acid ChemAxon average_mass 186.0572 ChemAxon mono_mass 185.99293909 ChemAxon smiles OC[C@@H](OP(O)(O)=O)C(O)=O ChemAxon formula C3H7O7P ChemAxon inchi InChI=1S/C3H7O7P/c4-1-2(3(5)6)10-11(7,8)9/h2,4H,1H2,(H,5,6)(H2,7,8,9)/t2-/m1/s1 ChemAxon inchikey GXIURPTVHJPJLF-UWTATZPHSA-N ChemAxon polar_surface_area 124.29 ChemAxon refractivity 31.26 ChemAxon polarizability 13.36 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 6 ChemAxon donor_count 4 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon Pentose phosphate pathway ec00030 Glycine, serine and threonine metabolism ec00260 Glycolysis / Gluconeogenesis ec00010 Methane metabolism ec00680 Microbial metabolism in diverse environments ec01120 Metabolic pathways eco01100 fructose metabolism Fructose metabolism begins with the transport of Beta-D-fructofuranose through a fructose PTS permease, resulting in a Beta-D-fructofuranose 1-phosphate. This compound is phosphorylated by an ATP driven 1-phosphofructokinase resulting in a fructose 1,6-biphosphate. This compound can either react with a fructose bisphosphate aldolase class 1 resulting in D-glyceraldehyde 3-phosphate and a dihydroxyacetone phosphate or through a fructose biphosphate aldolase class 2 resulting in a D-glyceraldehyde 3-phosphate. This compound can then either react in a reversible triosephosphate isomerase resulting in a dihydroxyacetone phosphate or react with a phosphate through a NAD dependent Glyceraldehyde 3-phosphate dehydrogenase resulting in a glyceric acid 1,3-biphosphate. This compound is desphosphorylated by a phosphoglycerate kinase resulting in a 3-phosphoglyceric acid.This compound in turn can either react with a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase or a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase resulting in a 2-phospho-D-glyceric acid. This compound interacts with an enolase resulting in a phosphoenolpyruvic acid and water. Phosphoenolpyruvic acid can react either through a AMP driven phosphoenoylpyruvate synthase or a ADP driven pyruvate kinase protein complex resulting in a pyruvic acid. Pyruvic acid reacts with CoA through a NAD driven pyruvate dehydrogenase complex resulting in a carbon dioxide and a Acetyl-CoA which gets incorporated into the TCA cycle pathway. PW000913 Metabolic glycerol metabolism Glycerol metabolism starts with glycerol is introduced into the cytoplasm through a glycerol channel GlpF Glycerol is then phosphorylated through an ATP mediated glycerol kinase resulting in a Glycerol 3-phosphate. This compound can also be obtained through a glycerophosphodiester reacting with water through a glycerophosphoryl diester phosphodiesterase or it can also be introduced into the cytoplasm through a glycerol-3-phosphate:phosphate antiporter. Glycerol 3-phosphate is then metabolized into a dihydroxyacetone phosphate in both aerobic or anaerobic conditions. In anaerobic conditions the metabolism is done through the reaction of glycerol 3-phosphate with a menaquinone mediated by a glycerol-3-phosphate dehydrogenase protein complex. In aerobic conditions, the metabolism is done through the reaction of glycerol 3-phosphate with ubiquinone mediated by a glycerol-3-phosphate dehydrogenase [NAD(P]+]. Dihydroxyacetone phosphate is then introduced into the fructose metabolism by turning a dihydroxyacetone into an isomer through a triosephosphate isomerase resulting in a D-glyceraldehyde 3-phosphate which in turn reacts with a phosphate through a NAD dependent Glyceraldehyde 3-phosphate dehydrogenase resulting in a glyceric acid 1,3-biphosphate. This compound is desphosphorylated by a phosphoglycerate kinase resulting in a 3-phosphoglyceric acid.This compound in turn can either react with a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase or a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase resulting in a 2-phospho-D-glyceric acid. This compound interacts with an enolase resulting in a phosphoenolpyruvic acid and water. Phosphoenolpyruvic acid can react either through a AMP driven phosphoenoylpyruvate synthase or a ADP driven pyruvate kinase protein complex resulting in a pyruvic acid. Pyruvic acid reacts with CoA through a NAD driven pyruvate dehydrogenase complex resulting in a carbon dioxide and a Acetyl-CoA which gets incorporated into the TCA cycle pathway. PW000914 Metabolic glycerol metabolism II Glycerol metabolism starts with glycerol is introduced into the cytoplasm through a glycerol channel GlpF Glycerol is then phosphorylated through an ATP mediated glycerol kinase resulting in a Glycerol 3-phosphate. This compound can also be obtained through sn-glycero-3-phosphocholine reacting with water through a glycerophosphoryl diester phosphodiesterase producing a benzyl alcohol, a hydrogen ion and a glycerol 3-phosphate or the campound can be introduced into the cytoplasm through a glycerol-3-phosphate:phosphate antiporter. Glycerol 3-phosphate is then metabolized into a dihydroxyacetone phosphate in both aerobic or anaerobic conditions. In anaerobic conditions the metabolism is done through the reaction of glycerol 3-phosphate with a menaquinone mediated by a glycerol-3-phosphate dehydrogenase protein complex. In aerobic conditions, the metabolism is done through the reaction of glycerol 3-phosphate with ubiquinone mediated by a glycerol-3-phosphate dehydrogenase [NAD(P]+]. Dihydroxyacetone phosphate is then introduced into the fructose metabolism by turning a dihydroxyacetone into an isomer through a triosephosphate isomerase resulting in a D-glyceraldehyde 3-phosphate which in turn reacts with a phosphate through a NAD dependent Glyceraldehyde 3-phosphate dehydrogenase resulting in a glyceric acid 1,3-biphosphate. This compound is desphosphorylated by a phosphoglycerate kinase resulting in a 3-phosphoglyceric acid.This compound in turn can either react with a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase or a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase resulting in a 2-phospho-D-glyceric acid. This compound interacts with an enolase resulting in a phosphoenolpyruvic acid and water. Phosphoenolpyruvic acid can react either through a AMP driven phosphoenoylpyruvate synthase or a ADP driven pyruvate kinase protein complex resulting in a pyruvic acid. Pyruvic acid reacts with CoA through a NAD driven pyruvate dehydrogenase complex resulting in a carbon dioxide and a Acetyl-CoA which gets incorporated into the TCA cycle pathway. PW000915 Metabolic glycerol metabolism III (sn-glycero-3-phosphoethanolamine) Glycerol metabolism starts with glycerol is introduced into the cytoplasm through a glycerol channel GlpF Glycerol is then phosphorylated through an ATP mediated glycerol kinase resulting in a Glycerol 3-phosphate. This compound can also be obtained through sn-glycero-3-phosphethanolamine reacting with water through a glycerophosphoryl diester phosphodiesterase producing a benzyl alcohol, a hydrogen ion and a glycerol 3-phosphate or the campound can be introduced into the cytoplasm through a glycerol-3-phosphate:phosphate antiporter. Glycerol 3-phosphate is then metabolized into a dihydroxyacetone phosphate in both aerobic or anaerobic conditions. In anaerobic conditions the metabolism is done through the reaction of glycerol 3-phosphate with a menaquinone mediated by a glycerol-3-phosphate dehydrogenase protein complex. In aerobic conditions, the metabolism is done through the reaction of glycerol 3-phosphate with ubiquinone mediated by a glycerol-3-phosphate dehydrogenase [NAD(P]+]. Dihydroxyacetone phosphate is then introduced into the fructose metabolism by turning a dihydroxyacetone into an isomer through a triosephosphate isomerase resulting in a D-glyceraldehyde 3-phosphate which in turn reacts with a phosphate through a NAD dependent Glyceraldehyde 3-phosphate dehydrogenase resulting in a glyceric acid 1,3-biphosphate. This compound is desphosphorylated by a phosphoglycerate kinase resulting in a 3-phosphoglyceric acid.This compound in turn can either react with a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase or a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase resulting in a 2-phospho-D-glyceric acid. This compound interacts with an enolase resulting in a phosphoenolpyruvic acid and water. Phosphoenolpyruvic acid can react either through a AMP driven phosphoenoylpyruvate synthase or a ADP driven pyruvate kinase protein complex resulting in a pyruvic acid. Pyruvic acid reacts with CoA through a NAD driven pyruvate dehydrogenase complex resulting in a carbon dioxide and a Acetyl-CoA which gets incorporated into the TCA cycle pathway. PW000916 Metabolic glycerol metabolism IV (glycerophosphoglycerol) Glycerol metabolism starts with glycerol is introduced into the cytoplasm through a glycerol channel GlpF Glycerol is then phosphorylated through an ATP mediated glycerol kinase resulting in a Glycerol 3-phosphate. This compound can also be obtained through glycerophosphoglycerol reacting with water through a glycerophosphoryl diester phosphodiesterase producing a benzyl alcohol, a hydrogen ion and a glycerol 3-phosphate or the campound can be introduced into the cytoplasm through a glycerol-3-phosphate:phosphate antiporter. Glycerol 3-phosphate is then metabolized into a dihydroxyacetone phosphate in both aerobic or anaerobic conditions. In anaerobic conditions the metabolism is done through the reaction of glycerol 3-phosphate with a menaquinone mediated by a glycerol-3-phosphate dehydrogenase protein complex. In aerobic conditions, the metabolism is done through the reaction of glycerol 3-phosphate with ubiquinone mediated by a glycerol-3-phosphate dehydrogenase [NAD(P]+]. Dihydroxyacetone phosphate is then introduced into the fructose metabolism by turning a dihydroxyacetone into an isomer through a triosephosphate isomerase resulting in a D-glyceraldehyde 3-phosphate which in turn reacts with a phosphate through a NAD dependent Glyceraldehyde 3-phosphate dehydrogenase resulting in a glyceric acid 1,3-biphosphate. This compound is desphosphorylated by a phosphoglycerate kinase resulting in a 3-phosphoglyceric acid.This compound in turn can either react with a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase or a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase resulting in a 2-phospho-D-glyceric acid. This compound interacts with an enolase resulting in a phosphoenolpyruvic acid and water. Phosphoenolpyruvic acid can react either through a AMP driven phosphoenoylpyruvate synthase or a ADP driven pyruvate kinase protein complex resulting in a pyruvic acid. Pyruvic acid reacts with CoA through a NAD driven pyruvate dehydrogenase complex resulting in a carbon dioxide and a Acetyl-CoA which gets incorporated into the TCA cycle pathway. PW000917 Metabolic glycerol metabolism V (glycerophosphoserine) Glycerol metabolism starts with glycerol is introduced into the cytoplasm through a glycerol channel GlpF Glycerol is then phosphorylated through an ATP mediated glycerol kinase resulting in a Glycerol 3-phosphate. This compound can also be obtained through glycerophosphoserine reacting with water through a glycerophosphoryl diester phosphodiesterase producing a benzyl alcohol, a hydrogen ion and a glycerol 3-phosphate or the campound can be introduced into the cytoplasm through a glycerol-3-phosphate:phosphate antiporter. Glycerol 3-phosphate is then metabolized into a dihydroxyacetone phosphate in both aerobic or anaerobic conditions. In anaerobic conditions the metabolism is done through the reaction of glycerol 3-phosphate with a menaquinone mediated by a glycerol-3-phosphate dehydrogenase protein complex. In aerobic conditions, the metabolism is done through the reaction of glycerol 3-phosphate with ubiquinone mediated by a glycerol-3-phosphate dehydrogenase [NAD(P]+]. Dihydroxyacetone phosphate is then introduced into the fructose metabolism by turning a dihydroxyacetone into an isomer through a triosephosphate isomerase resulting in a D-glyceraldehyde 3-phosphate which in turn reacts with a phosphate through a NAD dependent Glyceraldehyde 3-phosphate dehydrogenase resulting in a glyceric acid 1,3-biphosphate. This compound is desphosphorylated by a phosphoglycerate kinase resulting in a 3-phosphoglyceric acid.This compound in turn can either react with a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase or a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase resulting in a 2-phospho-D-glyceric acid. This compound interacts with an enolase resulting in a phosphoenolpyruvic acid and water. Phosphoenolpyruvic acid can react either through a AMP driven phosphoenoylpyruvate synthase or a ADP driven pyruvate kinase protein complex resulting in a pyruvic acid. Pyruvic acid reacts with CoA through a NAD driven pyruvate dehydrogenase complex resulting in a carbon dioxide and a Acetyl-CoA which gets incorporated into the TCA cycle pathway. PW000918 Metabolic glycolysis and pyruvate dehydrogenase Fructose metabolism begins with the transport of Beta-D-glucose 6-phosphate through a glucose PTS permease, resulting in a Beta-D-glucose 6-phosphate. This compound is isomerized by a glucose-6-phosphate isomerase resulting in a fructose 6-phosphate. This compound can be phosphorylated by two different enzymes, a pyridoxal phosphatase/fructose 1,6-bisphosphatase or a ATP driven-6-phosphofructokinase-1 resulting in a fructose 1,6-biphosphate. This compound can either react with a fructose bisphosphate aldolase class 1 resulting in D-glyceraldehyde 3-phosphate and a dihydroxyacetone phosphate or through a fructose biphosphate aldolase class 2 resulting in a D-glyceraldehyde 3-phosphate. This compound can then either react in a reversible triosephosphate isomerase resulting in a dihydroxyacetone phosphate or react with a phosphate through a NAD dependent Glyceraldehyde 3-phosphate dehydrogenase resulting in a glyceric acid 1,3-biphosphate. This compound is desphosphorylated by a phosphoglycerate kinase resulting in a 3-phosphoglyceric acid.This compound in turn can either react with a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase or a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase resulting in a 2-phospho-D-glyceric acid. This compound interacts with an enolase resulting in a phosphoenolpyruvic acid and water. Phosphoenolpyruvic acid can react either through a AMP driven phosphoenoylpyruvate synthase or a ADP driven pyruvate kinase protein complex resulting in a pyruvic acid. Pyruvic acid reacts with CoA through a NAD driven pyruvate dehydrogenase complex resulting in a carbon dioxide and a Acetyl-CoA which gets incorporated into the TCA cycle pathway. PW000785 Metabolic 2-O-alpha-mannosyl-D-glycerate degradation 2-O-α-Mannosyl-D-glycerate (MG) is an osmolyte utilized by hyperthermophilic archaea and bacteria. E. coli is able to utilize MG as a carbon source but not as protection against osmotic stress. MG utilization is controlled by the divergently transcribed mngR gene and mngAB operon. MngR acts as a repressor of the expression both mngR and mngAB. MngA is the EII of a PEP-dependent sugar phosphotransferase system responsible for the uptake and phosphorylation of MG to 2-O-(6-phospho-α-mannosyl)-D-glycerate, which is subsequently converted to mannose-6-phosphate and glycerate by the α-mannosidase MngB. Glycerate can be converted to 2-phosphoglycerate by glycerate kinase I encoded by the garK gene which is also induced when cells are grown in MG. (EcoCyc) PW002096 Metabolic gluconeogenesis I GLUCONEO-PWY glycolysis I GLYCOLYSIS respiration (anaerobic) ANARESP1-PWY D-galactarate degradation I GALACTARDEG-PWY <i>D</i>-glucarate degradation I GLUCARDEG-PWY 2-<I>O</I>-&alpha;-mannosyl-D-glycerate degradation PWY0-1300 Specdb::CMs 1458 Specdb::CMs 2401 Specdb::CMs 31460 Specdb::CMs 38589 Specdb::CMs 162311 Specdb::NmrOneD 21582 Specdb::NmrOneD 21583 Specdb::NmrOneD 21584 Specdb::NmrOneD 21585 Specdb::NmrOneD 21586 Specdb::NmrOneD 21587 Specdb::NmrOneD 21588 Specdb::NmrOneD 21589 Specdb::NmrOneD 21590 Specdb::NmrOneD 21591 Specdb::NmrOneD 21592 Specdb::NmrOneD 21593 Specdb::NmrOneD 21594 Specdb::NmrOneD 21595 Specdb::NmrOneD 21596 Specdb::NmrOneD 21597 Specdb::NmrOneD 21598 Specdb::NmrOneD 21599 Specdb::NmrOneD 21600 Specdb::NmrOneD 21601 Specdb::MsMs 29195 Specdb::MsMs 29196 Specdb::MsMs 29197 Specdb::MsMs 35753 Specdb::MsMs 35754 Specdb::MsMs 35755 Specdb::MsMs 438254 Specdb::MsMs 438255 Specdb::MsMs 438256 Specdb::MsMs 438257 Specdb::MsMs 438258 Specdb::MsMs 446709 Specdb::MsMs 446710 Specdb::MsMs 446711 Specdb::MsMs 446712 Specdb::MsMs 446713 Specdb::MsMs 2682372 Specdb::MsMs 2682373 Specdb::MsMs 2682374 Specdb::MsMs 3027180 Specdb::MsMs 3027181 Specdb::MsMs 3027182 HMDB03391 439278 388411 C00631 17835 2-PG PAG 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 Enolase P0A6P9 ENO_ECOLI eno http://ecmdb.ca/proteins/P0A6P9.xml Probable phosphoglycerate mutase gpmB P0A7A2 GPMB_ECOLI gpmB http://ecmdb.ca/proteins/P0A7A2.xml Glycerate kinase 2 P23524 GLXK2_ECOLI garK http://ecmdb.ca/proteins/P23524.xml 2,3-bisphosphoglycerate-independent phosphoglycerate mutase P37689 GPMI_ECOLI gpmI http://ecmdb.ca/proteins/P37689.xml 2,3-bisphosphoglycerate-dependent phosphoglycerate mutase P62707 GPMA_ECOLI gpmA http://ecmdb.ca/proteins/P62707.xml 2-Phospho-D-glyceric acid <> 3-Phosphoglycerate 3PGAREARR-RXN 2-Phospho-D-glyceric acid <> Water + Phosphoenolpyruvic acid R00658 2PGADEHYDRAT-RXN Adenosine triphosphate + Glyceric acid > 2-Phospho-D-glyceric acid + ADP + Hydrogen ion GKI-RXN 2-Phospho-D-glyceric acid <> 3-Phospho-D-glycerate R01518 3-Phosphoglycerate <> 2-Phospho-D-glyceric acid 3PGAREARR-RXN 2-Phospho-D-glyceric acid > Phosphoenolpyruvic acid + Water Adenosine triphosphate + Glyceric acid > ADP + 2-Phospho-D-glyceric acid 2-Phospho-D-glyceric acid > 3-Phospho-D-glycerate R01518 2-Phospho-D-glyceric acid + 2,3-Diphosphoglyceric acid <> 3-Phospho-D-glycerate R01518 3-Phosphoglyceric acid + 3-Phosphoglycerate > 2-Phospho-D-glyceric acid PW_R002637 2 2-Phospho-D-glyceric acid <> Water + Phosphoenolpyruvic acid