2.0 2012-05-31 13:57:34 -0600 2015-06-03 15:54:19 -0600 ECMDB03015 M2MDB000474 Malonic semialdehyde Malonic semialdehyde is formed in the alternative pathway of propionate metabolism and in the catabolism of beta-alanine. 3-Oxopropanoate 3-Oxopropanoic acid 3-Oxopropionate 3-Oxopropionic acid Formyl acetate Formyl acetic acid Formylacetate Formylacetic acid Malonaldehydate Malonaldehydic acid Malonate semialdehyde Malonate-S-ald Malonic acid semialdehyde Malonic acid-S-ald Malonic semialdehyde C3H4O3 88.0621 88.016043994 3-oxopropanoic acid 3-oxopropanoic acid 926-61-4 OC(=O)CC=O InChI=1S/C3H4O3/c4-2-1-3(5)6/h2H,1H2,(H,5,6) OAKURXIZZOAYBC-UHFFFAOYSA-N Solid Cytosol logp -0.69 ALOGPS logs 0.46 ALOGPS solubility 2.51e+02 g/l ALOGPS logp -0.49 ChemAxon pka_strongest_acidic 3.76 ChemAxon pka_strongest_basic -7.2 ChemAxon iupac 3-oxopropanoic acid ChemAxon average_mass 88.0621 ChemAxon mono_mass 88.016043994 ChemAxon smiles OC(=O)CC=O ChemAxon formula C3H4O3 ChemAxon inchi InChI=1S/C3H4O3/c4-2-1-3(5)6/h2H,1H2,(H,5,6) ChemAxon inchikey OAKURXIZZOAYBC-UHFFFAOYSA-N ChemAxon polar_surface_area 54.37 ChemAxon refractivity 18.06 ChemAxon polarizability 7.27 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Pyrimidine metabolism The metabolism of pyrimidines begins with L-glutamine interacting with water molecule and a hydrogen carbonate through an ATP driven carbamoyl phosphate synthetase resulting in a hydrogen ion, an ADP, a phosphate, an L-glutamic acid and a carbamoyl phosphate. The latter compound interacts with an L-aspartic acid through a aspartate transcarbamylase resulting in a phosphate, a hydrogen ion and a N-carbamoyl-L-aspartate. The latter compound interacts with a hydrogen ion through a dihydroorotase resulting in the release of a water molecule and a 4,5-dihydroorotic acid. This compound interacts with an ubiquinone-1 through a dihydroorotate dehydrogenase, type 2 resulting in a release of an ubiquinol-1 and an orotic acid. The orotic acid then interacts with a phosphoribosyl pyrophosphate through a orotate phosphoribosyltransferase resulting in a pyrophosphate and an orotidylic acid. The latter compound then interacts with a hydrogen ion through an orotidine-5 '-phosphate decarboxylase, resulting in an release of carbon dioxide and an Uridine 5' monophosphate. The Uridine 5' monophosphate process to get phosphorylated by an ATP driven UMP kinase resulting in the release of an ADP and an Uridine 5--diphosphate. Uridine 5-diphosphate can be metabolized in multiple ways in order to produce a Deoxyuridine triphosphate. 1.-Uridine 5-diphosphate interacts with a reduced thioredoxin through a ribonucleoside diphosphate reductase 1 resulting in the release of a water molecule and an oxidized thioredoxin and an dUDP. The dUDP is then phosphorylated by an ATP through a nucleoside diphosphate kinase resulting in the release of an ADP and a DeoxyUridine triphosphate. 2.-Uridine 5-diphosphate interacts with a reduced NrdH glutaredoxin-like protein through a Ribonucleoside-diphosphate reductase 1 resulting in a release of a water molecule, an oxidized NrdH glutaredoxin-like protein and a dUDP. The dUDP is then phosphorylated by an ATP through a nucleoside diphosphate kinase resulting in the release of an ADP and a DeoxyUridine triphosphate. 3.-Uridine 5-diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and an Uridinetriphosphate. The latter compound interacts with a reduced flavodoxin through ribonucleoside-triphosphate reductase resulting in the release of an oxidized flavodoxin, a water molecule and a Deoxyuridine triphosphate 4.-Uridine 5-diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and an Uridinetriphosphate The uridine triphosphate interacts with a L-glutamine and a water molecule through an ATP driven CTP synthase resulting in an ADP, a phosphate, a hydrogen ion, an L-glutamic acid and a cytidine triphosphate. The cytidine triphosphate interacts with a reduced flavodoxin through a ribonucleoside-triphosphate reductase resulting in the release of a water molecule, an oxidized flavodoxin and a dCTP. The dCTP interacts with a water molecule and a hydrogen ion through a dCTP deaminase resulting in a release of an ammonium molecule and a Deoxyuridine triphosphate. 5.-Uridine 5-diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and an Uridinetriphosphate The uridine triphosphate interacts with a L-glutamine and a water molecule through an ATP driven CTP synthase resulting in an ADP, a phosphate, a hydrogen ion, an L-glutamic acid and a cytidine triphosphate. The cytidine triphosphate then interacts spontaneously with a water molecule resulting in the release of a phosphate, a hydrogen ion and a CDP. The CDP then interacts with a reduced NrdH glutaredoxin-like protein through a ribonucleoside-diphosphate reductase 2 resulting in the release of a water molecule, an oxidized NrdH glutaredoxin-like protein and a dCDP. The dCDP is then phosphorylated through an ATP driven nucleoside diphosphate kinase resulting in an ADP and a dCTP. The dCTP interacts with a water molecule and a hydrogen ion through a dCTP deaminase resulting in a release of an ammonium molecule and a Deoxyuridine triphosphate. 6.-Uridine 5-diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and an Uridinetriphosphate The uridine triphosphate interacts with a L-glutamine and a water molecule through an ATP driven CTP synthase resulting in an ADP, a phosphate, a hydrogen ion, an L-glutamic acid and a cytidine triphosphate. The cytidine triphosphate then interacts spontaneously with a water molecule resulting in the release of a phosphate, a hydrogen ion and a CDP. The CDP interacts with a reduced thioredoxin through a ribonucleoside diphosphate reductase 1 resulting in a release of a water molecule, an oxidized thioredoxin and a dCDP. The dCDP is then phosphorylated through an ATP driven nucleoside diphosphate kinase resulting in an ADP and a dCTP. The dCTP interacts with a water molecule and a hydrogen ion through a dCTP deaminase resulting in a release of an ammonium molecule and a Deoxyuridine triphosphate. The deoxyuridine triphosphate then interacts with a water molecule through a nucleoside triphosphate pyrophosphohydrolase resulting in a release of a hydrogen ion, a phosphate and a dUMP. The dUMP then interacts with a methenyltetrahydrofolate through a thymidylate synthase resulting in a dihydrofolic acid and a 5-thymidylic acid. Then 5-thymidylic acid is then phosphorylated through a nucleoside diphosphate kinase resulting in the release of an ADP and thymidine 5'-triphosphate. PW000942 ec00240 Metabolic Inositol phosphate metabolism ec00562 beta-Alanine metabolism The Beta-Alanine Metabolism starts with a product of Aspartate metabolism. Aspartate is decarboxylated by aspartate 1-decarboxylase, releasing carbon dioxide and Beta-alanine. Beta alanine is then metabolized through a pantothenate synthetase resulting in Pantothenic acid undergoes phosphorylation through a ATP driven pantothenate kinase, resulting in D-4-phosphopantothenate. Pantothenate (vitamin B5) is the universal precursor for the synthesis of the 4'-phosphopantetheine moiety of coenzyme A and acyl carrier protein. Only plants and microorganismscan synthesize pantothenate de novo - animals require a dietary supplement. The enzymes of this pathway are therefore considered to be antimicrobial drug targets. PW000896 ec00410 Metabolic Propanoate metabolism Starting from L-threonine, this compound is deaminated through a threonine deaminase resulting in a hydrogen ion, a water molecule and a (2z)-2-aminobut-2-enoate. The latter compound then isomerizes to a 2-iminobutanoate, This compound then reacts spontaneously with hydrogen ion and a water molecule resulting in a ammonium and a 2-Ketobutyric acid. The latter compound interacts with CoA through a pyruvate formate-lyase / 2-ketobutyrate formate-lyase resulting in a formic acid and a propionyl-CoA. Propionyl-CoA can then be processed either into a 2-methylcitric acid or into a propanoyl phosphate. Propionyl-CoA interacts with oxalacetic acid and a water molecule through a 2-methylcitrate synthase resulting in a hydrogen ion, a CoA and a 2-Methylcitric acid.The latter compound is dehydrated through a 2-methylcitrate dehydratase resulting in a water molecule and cis-2-methylaconitate. The latter compound is then dehydrated by a bifunctional aconitate hydratase 2 and 2-methylisocitrate dehydratase resulting in a water molecule and methylisocitric acid. The latter compound is then processed by 2-methylisocitrate lyase resulting in a release of succinic acid and pyruvic acid. Succinic acid can then interact with a propionyl-CoA through a propionyl-CoA:succinate CoA transferase resulting in a propionic acid and a succinyl CoA. Succinyl-CoA is then isomerized through a methylmalonyl-CoA mutase resulting in a methylmalonyl-CoA. This compound is then decarboxylated through a methylmalonyl-CoA decarboxylase resulting in a release of Carbon dioxide and Propionyl-CoA. ropionyl-CoA interacts with a phosphate through a phosphate acetyltransferase / phosphate propionyltransferase resulting in a CoA and a propanoyl phosphate. Propionyl-CoA can react with a phosphate through a phosphate acetyltransferase / phosphate propionyltransferase resulting in a CoA and a propanoyl phosphate. The latter compound is then dephosphorylated through a ADP driven acetate kinase/propionate kinase protein complex resulting in an ATP and Propionic acid. Propionic acid can be processed by a reaction with CoA through a ATP-driven propionyl-CoA synthetase resulting in a pyrophosphate, an AMP and a propionyl-CoA. PW000940 ec00640 Metabolic Microbial metabolism in diverse environments ec01120 Chloroalkane and chloroalkene degradation ec00625 Uracil degradation III PW002026 Metabolic uracil degradation III PWY0-1471 Specdb::CMs 17389 Specdb::CMs 39548 Specdb::CMs 154640 Specdb::NmrOneD 92692 Specdb::NmrOneD 92693 Specdb::NmrOneD 92694 Specdb::NmrOneD 92695 Specdb::NmrOneD 92696 Specdb::NmrOneD 92697 Specdb::NmrOneD 92698 Specdb::NmrOneD 92699 Specdb::NmrOneD 92700 Specdb::NmrOneD 92701 Specdb::NmrOneD 92702 Specdb::NmrOneD 92703 Specdb::NmrOneD 92704 Specdb::NmrOneD 92705 Specdb::NmrOneD 92706 Specdb::NmrOneD 92707 Specdb::NmrOneD 92708 Specdb::NmrOneD 92709 Specdb::NmrOneD 92710 Specdb::NmrOneD 92711 Specdb::MsMs 20618 Specdb::MsMs 20619 Specdb::MsMs 20620 Specdb::MsMs 22169 Specdb::MsMs 22170 Specdb::MsMs 22171 Specdb::MsMs 2392750 Specdb::MsMs 2392751 Specdb::MsMs 2392752 Specdb::MsMs 2570249 Specdb::MsMs 2570250 Specdb::MsMs 2570251 HMDB11111 868 845 C00222 17960 MALONATE-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 Scholem RD, Brown GK: Metabolism of malonic semialdehyde in man. Biochem J. 1983 Oct 15;216(1):81-5. 6418146 4-aminobutyrate aminotransferase P22256 GABT_ECOLI gabT http://ecmdb.ca/proteins/P22256.xml 4-aminobutyrate aminotransferase_ P50457 PUUE_ECOLI puuE http://ecmdb.ca/proteins/P50457.xml Putative NADH dehydrogenase/NAD(P)H nitroreductase rutE P75894 RUTE_ECOLI rutE http://ecmdb.ca/proteins/P75894.xml NADP-dependent L-serine/L-allo-threonine dehydrogenase ydfG P39831 YDFG_ECOLI ydfG http://ecmdb.ca/proteins/P39831.xml Protein rutD P75895 RUTD_ECOLI rutD http://ecmdb.ca/proteins/P75895.xml Hydrogen ion + Malonic semialdehyde + NADPH > 3-Hydroxypropanoate + NADP R09289 RXN-8974 3-Aminoacrylate + Hydrogen ion + Water > Malonic semialdehyde + Ammonium beta-Alanine + alpha-Ketoglutarate <> Malonic semialdehyde + L-Glutamate R00908 3-Hydroxypropanoate + NADP <> Malonic semialdehyde + NADPH + Hydrogen ion R09289 3-Aminoacrylate + Water <> Malonic semialdehyde + Ammonia R09983 RXN0-6452 3-Aminoacrylate + Water > Malonic semialdehyde + Ammonia RXN0-6452 3-Hydroxypropanoate + NADP < Malonic semialdehyde + NADPH + Hydrogen ion RXN-8974 3-Hydroxypropanoate + NADP > Malonic semialdehyde + NADPH 2-Aminoacrylic acid + Water + Hydrogen ion > Malonic semialdehyde + Ammonium PW_R005909 beta-Alanine + alpha-Ketoglutarate <> Malonic semialdehyde + L-Glutamate Hydrogen ion + Malonic semialdehyde + NADPH >3 3-Hydroxypropanoate + NADP Hydrogen ion + Malonic semialdehyde + NADPH >3 3-Hydroxypropanoate + NADP