2.0 2012-05-31 09:57:38 -0600 2015-09-13 12:56:06 -0600 ECMDB00119 M2MDB000043 Glyoxylic acid Glyoxylic acid or oxoacetic acid is an organic compound that is both an aldehyde and a carboxylic acid. It is an intermediate of the glyoxylate cycle, which enables certain organisms to convert fatty acids into carbohydrates.The conjugate base of gloxylic acid is known as glyoxylate. This compound is an intermediate of the glyoxylate cycle, which enables organisms, such as bacteria, fungi and plants to convert fatty acids into carbohydrates. Glyoxylate is the byproduct of the amidation process in biosynthesis of several amidated peptides. The glyoxylate cycle is a metabolic pathway occurring in plants, and several microorganisms, such as E. coli and yeast. (PMID: 16396466) A-Ketoacetate A-Ketoacetic acid Alpha-Ketoacetate Alpha-Ketoacetic acid Formylformate Formylformic acid Glyox Glyoxalate Glyoxalic acid Glyoxylate Glyoxylic acid Oxalaldehydate Oxalaldehydic acid Oxoacetate Oxoacetic acid Oxoethanoate Oxoethanoic acid α-Ketoacetate α-Ketoacetic acid C2H2O3 74.0355 74.00039393 2-oxoacetic acid glyoxylic acid 298-12-4 OC(=O)C=O InChI=1S/C2H2O3/c3-1-2(4)5/h1H,(H,4,5) HHLFWLYXYJOTON-UHFFFAOYSA-N Liquid Cytosol logp -0.59 ALOGPS logs 0.48 ALOGPS solubility 2.24e+02 g/l ALOGPS melting_point -93 oC logp -0.13 ChemAxon pka_strongest_acidic 2.61 ChemAxon pka_strongest_basic -9.2 ChemAxon iupac 2-oxoacetic acid ChemAxon average_mass 74.0355 ChemAxon mono_mass 74.00039393 ChemAxon smiles OC(=O)C=O ChemAxon formula C2H2O3 ChemAxon inchi InChI=1S/C2H2O3/c3-1-2(4)5/h1H,(H,4,5) ChemAxon inchikey HHLFWLYXYJOTON-UHFFFAOYSA-N ChemAxon polar_surface_area 54.37 ChemAxon refractivity 13.5 ChemAxon polarizability 5.35 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Pentose phosphate pathway ec00030 Arginine and proline metabolism ec00330 Purine metabolism ec00230 Glycine, serine and threonine metabolism ec00260 Pyruvate metabolism ec00620 Methane metabolism ec00680 C5-Branched dibasic acid metabolism ec00660 Glyoxylate and dicarboxylate metabolism ec00630 Microbial metabolism in diverse environments ec01120 Chloroalkane and chloroalkene degradation ec00625 Metabolic pathways eco01100 Secondary Metabolites: Glyoxylate cycle The glyoxylate cycle starts with the interaction of Acetyl-Coa with a water molecule and Oxalacetic acid interact through a Citrate synthase resulting in a release of a coenzyme a and citric acid. The citric acid gets dehydrated through a citrate hydro-lyase resulting in the release of a water molecule and cis-Aconitic acid. The cis-Aconitic acid is then hydrated in an reversible reaction through an aconitate hydratase resulting in an Isocitric acid. The isocitric acid then interacts in a reversible reaction through isocitrate lyase resulting in the release of a succinic acid and a glyoxylic acid. The glyoxylic acid then reacts in a reversible reaction with an acetyl-coa, and a water molecule in a reversible reaction, resulting in a release of a coenzyme A, a hydrogen ion and an L-malic acid. The L-malic acid interacts in a reversible reaction through a NAD driven malate dehydrogenase resulting in the release of NADH, a hydrogen ion and an Oxalacetic acid. PW000967 Metabolic 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 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 glyoxylate cycle GLYOXYLATE-BYPASS glycolate and glyoxylate degradation I GLYCOLATEMET-PWY superpathway of glycol metabolism and degradation GLYOXDEG-PWY allantoin degradation to glyoxylate III PWY-5705 Specdb::CMs 893 Specdb::CMs 2958 Specdb::CMs 31004 Specdb::CMs 37302 Specdb::CMs 162291 Specdb::CMs 1050359 Specdb::EiMs 1251 Specdb::NmrOneD 1091 Specdb::NmrOneD 4736 Specdb::NmrOneD 4737 Specdb::NmrOneD 142290 Specdb::NmrOneD 142291 Specdb::NmrOneD 142292 Specdb::NmrOneD 142293 Specdb::NmrOneD 142294 Specdb::NmrOneD 142295 Specdb::NmrOneD 142296 Specdb::NmrOneD 142297 Specdb::NmrOneD 142298 Specdb::NmrOneD 142299 Specdb::NmrOneD 142300 Specdb::NmrOneD 142301 Specdb::NmrOneD 142302 Specdb::NmrOneD 142303 Specdb::NmrOneD 142304 Specdb::NmrOneD 142305 Specdb::NmrOneD 142306 Specdb::NmrOneD 142307 Specdb::NmrOneD 142308 Specdb::NmrOneD 142309 Specdb::MsMs 171 Specdb::MsMs 172 Specdb::MsMs 173 Specdb::MsMs 2909 Specdb::MsMs 2910 Specdb::MsMs 2911 Specdb::MsMs 11255 Specdb::MsMs 11256 Specdb::MsMs 11257 Specdb::MsMs 17927 Specdb::MsMs 17928 Specdb::MsMs 17929 Specdb::MsMs 437683 Specdb::MsMs 437684 Specdb::MsMs 437685 Specdb::MsMs 2775380 Specdb::MsMs 2775381 Specdb::MsMs 2775382 Specdb::MsMs 2907258 Specdb::MsMs 2907259 Specdb::MsMs 2907260 Specdb::NmrTwoD 1149 HMDB00119 760 740 C00048 16891 GLYOX GLV Glyoxylic acid 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 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 Popov, V. N., Moskalev, E. A., Shevchenko, M. I. u., Eprintsev, A. T. (2005). "[Comparative analysis of the glyoxylate cycle clue enzyme isocitrate lyases from organisms of different systemic groups]." Zh Evol Biokhim Fiziol 41:507-513. 16396466 Lee SH, Kim SO, Chung BC: Gas chromatographic-mass spectrometric determination of urinary oxoacids using O-(2,3,4,5,6-pentafluorobenzyl)oxime-trimethylsilyl ester derivatization and cation-exchange chromatography. J Chromatogr B Biomed Sci Appl. 1998 Nov 20;719(1-2):1-7. 9869358 Booth ED, Dofferhoff O, Boogaard PJ, Watson WP: Comparison of the metabolism of ethylene glycol and glycolic acid in vitro by precision-cut tissue slices from female rat, rabbit and human liver. Xenobiotica. 2004 Jan;34(1):31-48. 14742135 Naghizadeh F, Barlow D, King J: The reduction of oxo-acids by human tissue extracts. Clin Biochem. 1976 Apr;9(2):65-6. 1261003 Borondy PE, Michniewicz BM: Metabolic disposition of isoxicam in man, monkey, dog, and rat. Drug Metab Dispos. 1984 Jul-Aug;12(4):444-51. 6148211 Arvesen A, Maehlen J, Rosen L, Aas P: Myointimal hyperplasia and sympathetic reinnervation following local cold injury and rapid rewarming in the rabbit central ear artery. Vasa. 2001 Jul;30(3):176-83. 11582947 Motomiya Y, Oyama N, Iwamoto H, Uchimura T, Maruyama I: N epsilon-(carboxymethyl)lysine in blood from maintenance hemodialysis patients may contribute to dialysis-related amyloidosis. Kidney Int. 1998 Oct;54(4):1357-66. 9767556 Holmes E, Foxall PJ, Spraul M, Farrant RD, Nicholson JK, Lindon JC: 750 MHz 1H NMR spectroscopy characterisation of the complex metabolic pattern of urine from patients with inborn errors of metabolism: 2-hydroxyglutaric aciduria and maple syrup urine disease. J Pharm Biomed Anal. 1997 Jul;15(11):1647-59. 9260660 Mentasti E, Savigliano M, Marangella M, Petrarulo M, Linari F: High-performance liquid chromatographic determination of glyoxylic acid and other carbonyl compounds in urine. J Chromatogr. 1987 Jul 3;417(2):253-60. 3654878 Bruzzese FJ, Dix JA, Rava RP, Cerny LC: Resonance Raman spectroscopy of chemically modified hemoglobins. Biomater Artif Cells Artif Organs. 1990;18(2):143-56. 2369642 Schmitt A, Gasic-Milenkovic J, Schmitt J: Characterization of advanced glycation end products: mass changes in correlation to side chain modifications. Anal Biochem. 2005 Nov 1;346(1):101-6. Epub 2005 Aug 15. 16168380 Tainio H, Vaalasti A, Rechardt L: The distribution of sympathetic adrenergic, tyrosine hydroxylase- and neuropeptide Y-immunoreactive nerves in human axillary sweat glands. Histochemistry. 1986;85(2):117-20. 2875046 Davis WL, Goodman DB: Evidence for the glyoxylate cycle in human liver. Anat Rec. 1992 Dec;234(4):461-8. 1456449 Arvesen A, Maehlen J, Rosen L, Aas P: Early and late functional and histopathological perturbations in the rabbit ear-artery following local cold injury. Vasa. 1999 May;28(2):85-94. 10409918 Jie, Yuanping; Song, Zhen. Method for preparing glyoxylic acid. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 5pp. http://hmdb.ca/system/metabolites/msds/000/000/081/original/HMDB00119.pdf?1358463323 Malate synthase A P08997 MASY_ECOLI aceB http://ecmdb.ca/proteins/P08997.xml KHG/KDPG aldolase P0A955 ALKH_ECOLI eda http://ecmdb.ca/proteins/P0A955.xml Isocitrate lyase P0A9G6 ACEA_ECOLI aceA http://ecmdb.ca/proteins/P0A9G6.xml Glyoxylate carboligase P0AEP7 GCL_ECOLI gcl http://ecmdb.ca/proteins/P0AEP7.xml Glycolate oxidase subunit glcD P0AEP9 GLCD_ECOLI glcD http://ecmdb.ca/proteins/P0AEP9.xml Malate synthase G P37330 MASZ_ECOLI glcB http://ecmdb.ca/proteins/P37330.xml Glyoxylate/hydroxypyruvate reductase B P37666 GHRB_ECOLI ghrB http://ecmdb.ca/proteins/P37666.xml Glycolate oxidase iron-sulfur subunit P52074 GLCF_ECOLI glcF http://ecmdb.ca/proteins/P52074.xml Glyoxylate/hydroxypyruvate reductase A P75913 GHRA_ECOLI ghrA http://ecmdb.ca/proteins/P75913.xml Ureidoglycolate hydrolase P77731 ALLA_ECOLI allA http://ecmdb.ca/proteins/P77731.xml Alkanesulfonate monooxygenase P80645 SSUD_ECOLI ssuD http://ecmdb.ca/proteins/P80645.xml Glycolate oxidase subunit glcE P52073 GLCE_ECOLI glcE http://ecmdb.ca/proteins/P52073.xml Short-chain fatty acids transporter P76460 ATOE_ECOLI atoE http://ecmdb.ca/proteins/P76460.xml Glyoxylic acid + Hydrogen ion + NADPH + Glycolate <> Glycolic acid + NADP R00465 GLYOXYLATE-REDUCTASE-NADP+-RXN Glycolic acid + Ubiquinone-8 > Glyoxylic acid + Ubiquinol-8 Glycolic acid + Menaquinone 8 > Glyoxylic acid + Menaquinol 8 2-Demethylmenaquinone 8 + Glycolic acid > 2-Demethylmenaquinol 8 + Glyoxylic acid Glyoxylic acid + Hydrogen ion + NADH > Glycolic acid + NAD Acetyl-CoA + Glyoxylic acid + Water <> Coenzyme A + Hydrogen ion + L-Malic acid R00472 MALSYN-RXN 2 Hydrogen ion + Water + (S)-Ureidoglycolic acid > Carbon dioxide + Glyoxylic acid +2 Ammonium 2 Glyoxylic acid + Hydrogen ion <> Tartronate semialdehyde + Carbon dioxide R00013 GLYOCARBOLIG-RXN FMNH + Oxygen + Sulfoacetate > Flavin Mononucleotide + Glyoxylic acid + Hydrogen ion + Water + Sulfite Isocitric acid <> Glyoxylic acid + Succinic acid R00479 ISOCIT-CLEAV-RXN 2 Glyoxylic acid <> Tartronate semialdehyde + Carbon dioxide R00013 Glycolic acid + NADP <> Glyoxylic acid + NADPH + Hydrogen ion R00465 GLYOXYLATE-REDUCTASE-NADP+-RXN (S)-Ureidoglycolic acid + Water <> Glyoxylic acid +2 Ammonia + Carbon dioxide R00469 4-Hydroxy-2-oxoglutaric acid <> Pyruvic acid + Glyoxylic acid R00470 4OH2OXOGLUTARALDOL-RXN D-4-Hydroxy-2-oxoglutarate <> Pyruvic acid + Glyoxylic acid R00471 L-Malic acid + Coenzyme A <> Acetyl-CoA + Water + Glyoxylic acid R00472 Glycolic acid + Oxygen <> Glyoxylic acid + Hydrogen peroxide R00475 Dehydroglycine + Water > Glyoxylic acid + Ammonia RXN-13329 4-Hydroxy-2-oxoglutaric acid Glyoxylic acid + Pyruvic acid 4OH2OXOGLUTARALDOL-RXN an oxidized electron acceptor + Glycolic acid > a reduced electron acceptor + Glyoxylic acid GLYCOLATEDEHYDRO-RXN Hydrogen ion + Glyoxylic acid > Carbon dioxide + Tartronate semialdehyde GLYOCARBOLIG-RXN Glycolic acid + NADP < Hydrogen ion + NADPH + Glyoxylic acid GLYOXYLATE-REDUCTASE-NADP+-RXN Propionyl-CoA + Water + Glyoxylic acid <> 2-hydroxyglutarate + Hydrogen ion + Coenzyme A HYDGLUTSYN-RXN Acetyl-CoA + Water + Glyoxylic acid > Hydrogen ion + L-Malic acid + Coenzyme A MALSYN-RXN (S)-Ureidoglycolic acid > Urea + Glyoxylic acid UREIDOGLYCOLATE-LYASE-RXN Isocitric acid > Succinic acid + Glyoxylic acid 4-Hydroxy-2-oxoglutaric acid > Pyruvic acid + Glyoxylic acid (S)-Ureidoglycolic acid + Water > Glyoxylic acid +2 Ammonia + Carbon dioxide 2 Glyoxylic acid > Tartronate semialdehyde + Carbon dioxide Glycolic acid + NADP > Glyoxylic acid + NADPH Acetyl-CoA + Water + Glyoxylic acid > L-Malic acid + CoA (S)-Ureidoglycolic acid <> Glyoxylic acid + Urea R00776 L-Alanine + Glyoxylic acid + L-Alanine <> Glycine + Pyruvic acid PW_R002587 Glycolic acid + an oxidized electron-transfer flavoprotein  > Reduced acceptor + Glyoxylic acid PW_R002979 2 Glycolic acid + 2 an oxidized electron-transfer flavoprotein  >2 Reduced acceptor +2 Glyoxylic acid PW_R002981 Glyoxylic acid + Water + Acetyl-CoA > Coenzyme A + Hydrogen ion + L-Malic acid + L-Malic acid PW_R002980 2 Glyoxylic acid + Hydrogen ion > Carbon dioxide + Tartronate semialdehyde PW_R002982 Isocitric acid + Isocitric acid <> Succinic acid + Glyoxylic acid PW_R003710 Acetyl-CoA + Glyoxylic acid + Water <> Coenzyme A + Hydrogen ion + L-Malic acid 2 Glyoxylic acid + Hydrogen ion <> Tartronate semialdehyde + Carbon dioxide (S)-Ureidoglycolic acid + Water <> Glyoxylic acid +2 Ammonia + Carbon dioxide Glyoxylic acid + Hydrogen ion + NADPH + Glycolate <> Glycolic acid + NADP Isocitric acid <> Glyoxylic acid + Succinic acid Glycolic acid + Oxygen <> Glyoxylic acid + Hydrogen peroxide (S)-Ureidoglycolic acid + Water <> Glyoxylic acid +2 Ammonia + Carbon dioxide Glyoxylic acid + Hydrogen ion + NADPH + Glycolate <> Glycolic acid + NADP Isocitric acid <> Glyoxylic acid + Succinic acid Glycolic acid + Oxygen <> Glyoxylic acid + Hydrogen peroxide Glycolic acid + Oxygen <> Glyoxylic acid + Hydrogen peroxide