2.0 2012-05-31 14:10:18 -0600 2015-06-03 15:54:57 -0600 ECMDB06938 M2MDB000707 Tartronate semialdehyde Tartronate semialdehyde is an intermediate in ascorbate and aldarate as well as glyoxylate and dicarboxylate metabolism. It is generated from 2-dehydro-3-deoxy-D-glucarate and 5-dehydro-4-deoxy-D-glucarate via the enzyme 2-dehydro-3-deoxyglucarate aldolase [EC:4.1.2.20]. 2-Hydroxy-3-oxopropanoate 2-Hydroxy-3-oxopropanoic acid Hydroxymalonaldehydate Hydroxymalonaldehydic acid Tartronate-S-ald Tartronic acid semialdehyde Tartronic acid-S-ald Tartronic semialdehyde C3H4O4 104.0615 104.010958616 2-hydroxy-3-oxopropanoic acid tartronate semialdehyde OC(C=O)C(O)=O InChI=1S/C3H4O4/c4-1-2(5)3(6)7/h1-2,5H,(H,6,7) QWBAFPFNGRFSFB-UHFFFAOYSA-N Solid Cytosol logp -0.92 ALOGPS logs 0.50 ALOGPS solubility 3.27e+02 g/l ALOGPS logp -1.2 ChemAxon pka_strongest_acidic 3.04 ChemAxon pka_strongest_basic -4.5 ChemAxon iupac 2-hydroxy-3-oxopropanoic acid ChemAxon average_mass 104.0615 ChemAxon mono_mass 104.010958616 ChemAxon smiles OC(C=O)C(O)=O ChemAxon formula C3H4O4 ChemAxon inchi InChI=1S/C3H4O4/c4-1-2(5)3(6)7/h1-2,5H,(H,6,7) ChemAxon inchikey QWBAFPFNGRFSFB-UHFFFAOYSA-N ChemAxon polar_surface_area 74.6 ChemAxon refractivity 19.4 ChemAxon polarizability 8.1 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Ascorbate and aldarate metabolism ec00053 Glyoxylate and dicarboxylate metabolism ec00630 Metabolic pathways eco01100 glycolate and glyoxylate degradation Glycolic acid is introduced into the cytoplasm through either a glycolate / lactate:H+ symporter or a acetate / glycolate transporter. Once inside, glycolic acid reacts with an oxidized electron-transfer flavoprotein through a glycolate oxidase resulting in a reduced acceptor and glyoxylic acid. Glyoxylic acid can also be obtained from the introduction of glyoxylic acid. It can also be obtained from the metabolism of (S)-allantoin. S-allantoin is introduced into the cytoplasm through a purine and pyrimidine transporter(allantoin specific). Once inside, the compound reacts with water through a allantoinase resulting in hydrogen ion and allantoic acid. Allantoic acid then reacts with water and hydrogen ion through a allantoate amidohydrolase resulting in a carbon dioxide, ammonium and S-ureidoglycine. The latter compound reacts with water through a S-ureidoglycine aminohydrolase resulting in ammonium and S-ureidoglycolic acid which in turn reacts with a Ureidoglycolate lyase resulting in urea and glyoxylic acid. Glyoxylic acid can either be metabolized into L-malic acid by a reaction with acetyl-CoA and Water through a malate synthase G which also releases hydrogen ion and Coenzyme A. L-malic acid is then incorporated into the TCA cycle. Glyoxylic acid can also be metabolized by glyoxylate carboligase, releasing a carbon dioxide and tartronate semialdehyde. The latter compound is then reduced by an NADH driven tartronate semialdehyde reductase 2 resulting in glyceric acid. Glyceric acid is phosphorylated by a glycerate kinase 2 resulting in a 3-phosphoglyceric acid. This compound is then integrated into various other pathways: cysteine biosynthesis, serine biosynthesis and glycolysis and pyruvate dehydrogenase. PW000827 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 glycolate and glyoxylate degradation II Oxaloglycolate (2-Hydroxy-3-oxosuccinate) interacts with a tartrate dehydrogenase resulting in a L-tartrate. L-tartrate then interacts with tartrate dehydrogenase resulting in a Oxaloacetate. Oxaloacetate and acetyl-coa interact to result in a citrate which is processed by a aconitate hydratase resulting in a cis-Aconitate and further more into a isocitrate which will eventually be procressed into a glyoxylic acid. Glyoxylic acid can either be metabolized into L-malic acid by a reaction with acetyl-CoA and Water through a malate synthase G which also releases hydrogen ion and Coenzyme A. L-malic acid is then incorporated into the TCA cycle. Glyoxylic acid can also be metabolized by glyoxylate carboligase, releasing a carbon dioxide and tartronate semialdehyde. The latter compound is then reduced by an NADH driven tartronate semialdehyde reductase 2 resulting in glyceric acid. Glyceric acid is phosphorylated by a glycerate kinase 2 resulting in a 3-phosphoglyceric acid. This compound is then integrated into various other pathways: cysteine biosynthesis, serine biosynthesis and glycolysis and pyruvate dehydrogenase. PW002021 Metabolic glycolate and glyoxylate degradation I GLYCOLATEMET-PWY D-galactarate degradation I GALACTARDEG-PWY <i>D</i>-glucarate degradation I GLUCARDEG-PWY Specdb::CMs 22083 Specdb::CMs 39143 Specdb::CMs 135673 Specdb::CMs 143407 Specdb::NmrOneD 150580 Specdb::NmrOneD 150581 Specdb::NmrOneD 150582 Specdb::NmrOneD 150583 Specdb::NmrOneD 150584 Specdb::NmrOneD 150585 Specdb::NmrOneD 150586 Specdb::NmrOneD 150587 Specdb::NmrOneD 150588 Specdb::NmrOneD 150589 Specdb::NmrOneD 150590 Specdb::NmrOneD 150591 Specdb::NmrOneD 150592 Specdb::NmrOneD 150593 Specdb::NmrOneD 150594 Specdb::NmrOneD 150595 Specdb::NmrOneD 150596 Specdb::NmrOneD 150597 Specdb::NmrOneD 150598 Specdb::NmrOneD 150599 Specdb::MsMs 25811 Specdb::MsMs 25812 Specdb::MsMs 25813 Specdb::MsMs 32369 Specdb::MsMs 32370 Specdb::MsMs 32371 Specdb::MsMs 3040459 Specdb::MsMs 3040460 Specdb::MsMs 3040461 Specdb::MsMs 3103055 Specdb::MsMs 3103056 Specdb::MsMs 3103057 HMDB06938 1090 C01146 16992 TARTRONATE-S-ALD 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 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 2-hydroxy-3-oxopropionate reductase P0ABQ2 GARR_ECOLI garR http://ecmdb.ca/proteins/P0ABQ2.xml Glyoxylate carboligase P0AEP7 GCL_ECOLI gcl http://ecmdb.ca/proteins/P0AEP7.xml 5-keto-4-deoxy-D-glucarate aldolase P23522 GARL_ECOLI garL http://ecmdb.ca/proteins/P23522.xml Hydroxypyruvate isomerase P30147 HYI_ECOLI hyi http://ecmdb.ca/proteins/P30147.xml 2-hydroxy-3-oxopropionate reductase_ P77161 GLXR_ECOLI glxR http://ecmdb.ca/proteins/P77161.xml Tartronate semialdehyde + Hydrogen ion + NADH <> Glyceric acid + NAD R01745 RXN0-5289 2 Glyoxylic acid + Hydrogen ion <> Tartronate semialdehyde + Carbon dioxide R00013 GLYOCARBOLIG-RXN Hydroxypyruvic acid <> Tartronate semialdehyde R01394 RXN0-305 5-Dehydro-4-deoxy-D-glucarate > Tartronate semialdehyde + Pyruvic acid R02754 KDGALDOL-RXN 2 Glyoxylic acid <> Tartronate semialdehyde + Carbon dioxide R00013 Glyceric acid + NAD <> Tartronate semialdehyde + NADH + Hydrogen ion R01745 RXN0-5289 Glyceric acid + NADP <> Tartronate semialdehyde + NADPH + Hydrogen ion R01747 5-Dehydro-4-deoxy-D-glucarate <> Pyruvic acid + Tartronate semialdehyde R02754 Tartronate semialdehyde + Pyruvic acid <> 2-Dehydro-3-deoxy-D-glucarate R03277 Hydrogen ion + Glyoxylic acid > Carbon dioxide + Tartronate semialdehyde GLYOCARBOLIG-RXN NAD(P)⁺ + Glyceric acid < NAD(P)H + Tartronate semialdehyde + Hydrogen ion TSA-REDUCT-RXN 2-Dehydro-3-deoxy-D-glucarate > Pyruvic acid + Tartronate semialdehyde Glyceric acid + NAD(P)(+) > Tartronate semialdehyde + NAD(P)H 2 Glyoxylic acid > Tartronate semialdehyde + Carbon dioxide Hydroxypyruvic acid > Tartronate semialdehyde Glyceric acid + NAD + NADP <> Tartronate semialdehyde + NADH + NADPH + Hydrogen ion R01745 R01747 5-dehydro-4-deoxy-D-glucarate(2−) > Pyruvic acid + Tartronate semialdehyde PW_R002725 Tartronate semialdehyde + Hydrogen ion + NADPH + NADPH > NADP + Glyceric acid PW_R002727 2 Glyoxylic acid + Hydrogen ion > Carbon dioxide + Tartronate semialdehyde PW_R002982 Tartronate semialdehyde + NADH + Hydrogen ion > NAD + Glyceric acid PW_R002983 Tartronate semialdehyde + Hydrogen ion + NADH <> Glyceric acid + NAD Hydroxypyruvic acid <> Tartronate semialdehyde 2 Glyoxylic acid + Hydrogen ion <> Tartronate semialdehyde + Carbon dioxide Hydroxypyruvic acid <> Tartronate semialdehyde