2.0 2012-08-09 09:16:11 -0600 2015-09-13 15:15:32 -0600 ECMDB21419 M2MDB001814 2-Phosphoglyceric acid 2-Phosphoglyceric acid (2PGA) is a glyceric acid which serves as the substrate in the ninth step of glycolysis. It is catalyzed by enolase into phosphoenolpyruvate (PEP), the penultimate step in the conversion of glucose to pyruvate. Enolase catalyzes the beta-elimination reaction in a stepwise manner wherein OH- is eliminated from C3 of a discrete carbanion (enolate) intermediate. This intermediate is created by removal of the proton from C2 of 2PGA by a base in the active site. (PMID: 8994873, Wikipedia) 2-(dihydrogen phosphate)Glycerate 2-(dihydrogen phosphate)Glyceric acid 2-(Dihydrogen phosphoric acid)glyceric acid 2-P-D-Glycerate 2-P-D-glyceric acid 2-P-glycerate 2-P-glyceric acid 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 2-phospho-DL-Glycerate 2-Phospho-DL-glyceric acid 2-Phosphoglycerate 3-Hydroxy-2-phosphonooxypropanoate 3-Hydroxy-2-phosphonooxypropanoic acid D-2-Phosphoglycerate D-2-Phosphoglyceric acid D-Glycerate 2-phosphate D-Glyceric acid 2-phosphoric acid DL-2-Phosphoglycerate DL-2-Phosphoglyceric acid Glycerate 2-phosphate Glyceric acid 2-phosphate Glyceric acid 2-phosphoric acid Phosphoglycerate Phosphoglyceric acid C3H7O7P 186.0572 185.99293909 3-hydroxy-2-(phosphonooxy)propanoic acid 2-phosphoglyceric acid 2553-59-5 OCC(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) GXIURPTVHJPJLF-UHFFFAOYSA-N Solid Cytoplasm 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 3-hydroxy-2-(phosphonooxy)propanoic acid ChemAxon average_mass 186.0572 ChemAxon mono_mass 185.99293909 ChemAxon smiles OCC(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) ChemAxon inchikey GXIURPTVHJPJLF-UHFFFAOYSA-N ChemAxon polar_surface_area 124.29 ChemAxon refractivity 31.26 ChemAxon polarizability 13.37 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 6 ChemAxon donor_count 4 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon Gluconeogenesis from L-malic acid Gluconeogenesis from L-malic acid starts from the introduction of L-malic acid into cytoplasm either through a C4 dicarboxylate / orotate:H+ symporter or a dicarboxylate transporter (succinic acid antiporter). L-malic acid is then metabolized through 3 possible ways: NAD driven malate dehydrogenase resulting in oxalacetic acid, NADP driven malate dehydrogenase B resulting pyruvic acid or malate dehydrogenase, NAD-requiring resulting in pyruvic acid. Oxalacetic acid is processed by phosphoenolpyruvate carboxykinase (ATP driven) while pyruvic acid is processed by phosphoenolpyruvate synthetase resulting in phosphoenolpyruvic acid. This compound is dehydrated by enolase resulting in an 2-phosphoglyceric acid. This compound is then isomerized by 2,3-bisphosphoglycerate-independent phosphoglycerate mutase resulting in a 3-phosphoglyceric acid which is phosphorylated by an ATP driven phosphoglycerate kinase resulting in an glyceric acid 1,3-biphosphate. This compound undergoes an NADH driven glyceraldehyde 3-phosphate dehydrogenase reaction resulting in a D-Glyceraldehyde 3-phosphate which is first isomerized into dihydroxyacetone phosphate through an triosephosphate isomerase. D-glyceraldehyde 3-phosphate and Dihydroxyacetone phosphate react through a fructose biphosphate aldolase protein complex resulting in a fructose 1,6-biphosphate. This compound is metabolized by a fructose-1,6-bisphosphatase resulting in a Beta-D-fructofuranose 6-phosphate which is then isomerized into a Beta-D-glucose 6-phosphate through a glucose-6-phosphate isomerase. PW000819 Metabolic superpathway of D-glucarate and D-galactarate degradation Galactarate is a naturally occurring dicarboxylic acid analog of D-galactose. E. coli can use both diacid sugars galactarate and D-glucarate as the sole source of carbon for growth. The initial step in the degradation of galactarate is its dehydration to 5-dehydro-4-deoxy-D-glucarate(2--) by galactarate dehydratase. Glucaric acid can also be dehydrated by a glucarate dehydratase resulting in water and 5-dehydro-4-deoxy-D-glucarate(2--). The 5-dehydro-4-deoxy-D-glucarate(2--) is then metabolized by a alpha-dehydro-beta-deoxy-D-glucarate aldolase resulting in pyruvic acid and a tartonate semialdehyde. Pyruvic acid interacts with coenzyme A through a NAD driven Pyruvate dehydrogenase complex resulting in a carbon dioxide, an NADH and an acetyl-CoA. The tartronate semialdehyde interacts with a hydrogen ion through a NADPH driven tartronate semialdehyde reductase resulting in a NADP and a glyceric acid. The glyceric acid is phosphorylated by an ATP-driven glycerate kinase 2 resulting in an ADP, a hydrogen ion and a 2-phosphoglyceric acid. The latter compound is dehydrated by an enolase resulting in the release of water and a phosphoenolpyruvic acid. The phosphoenolpyruvic acid interacts with a hydrogen ion through an ADP driven pyruvate kinase resulting in an ATP and a pyruvic acid. The pyruvic acid then interacts with water and an ATP through a phosphoenolpyruvate synthetase resulting in the release of a hydrogen ion, a phosphate, an AMP and a Phosphoenolpyruvic acid. PW000795 Metabolic Specdb::CMs 16065 Specdb::CMs 37465 Specdb::CMs 132761 Specdb::CMs 140495 Specdb::CMs 1059474 Specdb::CMs 1059476 Specdb::CMs 1059478 Specdb::CMs 1059480 Specdb::CMs 1059481 Specdb::CMs 1059483 Specdb::CMs 1059485 Specdb::CMs 1059486 Specdb::CMs 1059488 Specdb::CMs 1059490 Specdb::CMs 1059492 Specdb::CMs 1059494 Specdb::CMs 1059495 Specdb::NmrOneD 143670 Specdb::NmrOneD 143671 Specdb::NmrOneD 143672 Specdb::NmrOneD 143673 Specdb::NmrOneD 143674 Specdb::NmrOneD 143675 Specdb::NmrOneD 143676 Specdb::NmrOneD 143677 Specdb::NmrOneD 143678 Specdb::NmrOneD 143679 Specdb::NmrOneD 143680 Specdb::NmrOneD 143681 Specdb::NmrOneD 143682 Specdb::NmrOneD 143683 Specdb::NmrOneD 143684 Specdb::NmrOneD 143685 Specdb::NmrOneD 143686 Specdb::NmrOneD 143687 Specdb::NmrOneD 143688 Specdb::NmrOneD 143689 Specdb::MsMs 10028 Specdb::MsMs 10029 Specdb::MsMs 10030 Specdb::MsMs 16700 Specdb::MsMs 16701 Specdb::MsMs 16702 Specdb::MsMs 2228781 Specdb::MsMs 2230647 Specdb::MsMs 2231109 Specdb::MsMs 2233115 Specdb::MsMs 2233498 Specdb::MsMs 2235419 Specdb::MsMs 2289168 Specdb::MsMs 2289169 Specdb::MsMs 2289170 Specdb::MsMs 2650052 Specdb::MsMs 2650053 Specdb::MsMs 2650054 HMDB00362 59 58 24344 2-Phosphoglycerate 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 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 Reed, G. H., Poyner, R. R., Larsen, T. M., Wedekind, J. E., Rayment, I. (1996). "Structural and mechanistic studies of enolase." Curr Opin Struct Biol 6:736-743. 8994873 Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. 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Muscle Nerve. 1995;3:S50-3. 7603528 Mulquiney PJ, Bubb WA, Kuchel PW: Model of 2,3-bisphosphoglycerate metabolism in the human erythrocyte based on detailed enzyme kinetic equations: in vivo kinetic characterization of 2,3-bisphosphoglycerate synthase/phosphatase using 13C and 31P NMR. Biochem J. 1999 Sep 15;342 Pt 3:567-80. 10477268 Reher M, Bott M, Schonheit P: Characterization of glycerate kinase (2-phosphoglycerate forming), a key enzyme of the nonphosphorylative Entner-Doudoroff pathway, from the thermoacidophilic euryarchaeon Picrophilus torridus. FEMS Microbiol Lett. 2006 Jun;259(1):113-9. 16684110 Wold, Finn. L-Glyceric acid monophosphates. Journal of Organic Chemistry (1961), 26 197-9. Enolase P0A6P9 ENO_ECOLI eno http://ecmdb.ca/proteins/P0A6P9.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-Phosphoglyceric acid + 2-Phosphoglyceric acid > 3-Phosphoglyceric acid + 3-Phosphoglycerate PW_R002933 Phosphoenolpyruvic acid > Water + 2-Phosphoglyceric acid + 2-Phosphoglyceric acid PW_R002932 2-Phosphoglyceric acid + 2-Phosphoglyceric acid <> Water + Phosphoenolpyruvic acid PW_R003674 Glyceric acid + Adenosine triphosphate > Hydrogen ion + Adenosine diphosphate + 2-Phosphoglyceric acid + ADP + 2-Phosphoglyceric acid PW_R002728