2.02012-05-31 13:57:34 -06002015-06-03 15:54:19 -0600ECMDB03015M2MDB000474Malonic semialdehydeMalonic semialdehyde is formed in the alternative pathway of propionate metabolism and in the catabolism of beta-alanine. 3-Oxopropanoate3-Oxopropanoic acid3-Oxopropionate3-Oxopropionic acidFormyl acetateFormyl acetic acidFormylacetateFormylacetic acidMalonaldehydateMalonaldehydic acidMalonate semialdehydeMalonate-S-aldMalonic acid semialdehydeMalonic acid-S-aldMalonic semialdehydeC3H4O388.062188.0160439943-oxopropanoic acid3-oxopropanoic acid926-61-4OC(=O)CC=OInChI=1S/C3H4O3/c4-2-1-3(5)6/h2H,1H2,(H,5,6)OAKURXIZZOAYBC-UHFFFAOYSA-NSolidCytosollogp-0.69logs0.46solubility2.51e+02 g/llogp-0.49pka_strongest_acidic3.76pka_strongest_basic-7.2iupac3-oxopropanoic acidaverage_mass88.0621mono_mass88.016043994smilesOC(=O)CC=OformulaC3H4O3inchiInChI=1S/C3H4O3/c4-2-1-3(5)6/h2H,1H2,(H,5,6)inchikeyOAKURXIZZOAYBC-UHFFFAOYSA-Npolar_surface_area54.37refractivity18.06polarizability7.27rotatable_bond_count2acceptor_count3donor_count1physiological_charge-1formal_charge0Pyrimidine metabolismThe 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.PW000942ec00240MetabolicInositol phosphate metabolismec00562beta-Alanine metabolismThe 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.PW000896ec00410MetabolicPropanoate 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.PW000940ec00640MetabolicMicrobial metabolism in diverse environmentsec01120Chloroalkane and chloroalkene degradationec00625Uracil degradation IIIPW002026Metabolicuracil degradation IIIPWY0-1471Specdb::CMs17389Specdb::CMs39548Specdb::CMs154640Specdb::NmrOneD92692Specdb::NmrOneD92693Specdb::NmrOneD92694Specdb::NmrOneD92695Specdb::NmrOneD92696Specdb::NmrOneD92697Specdb::NmrOneD92698Specdb::NmrOneD92699Specdb::NmrOneD92700Specdb::NmrOneD92701Specdb::NmrOneD92702Specdb::NmrOneD92703Specdb::NmrOneD92704Specdb::NmrOneD92705Specdb::NmrOneD92706Specdb::NmrOneD92707Specdb::NmrOneD92708Specdb::NmrOneD92709Specdb::NmrOneD92710Specdb::NmrOneD92711Specdb::MsMs20618Specdb::MsMs20619Specdb::MsMs20620Specdb::MsMs22169Specdb::MsMs22170Specdb::MsMs22171Specdb::MsMs2392750Specdb::MsMs2392751Specdb::MsMs2392752Specdb::MsMs2570249Specdb::MsMs2570250Specdb::MsMs2570251HMDB11111868845C0022217960MALONATE-S-ALDKeseler, 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-D590.21097882Kanehisa, 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-D114.22080510Scholem RD, Brown GK: Metabolism of malonic semialdehyde in man. Biochem J. 1983 Oct 15;216(1):81-5.64181464-aminobutyrate aminotransferaseP22256GABT_ECOLIgabThttp://ecmdb.ca/proteins/P22256.xml4-aminobutyrate aminotransferase_P50457PUUE_ECOLIpuuEhttp://ecmdb.ca/proteins/P50457.xmlPutative NADH dehydrogenase/NAD(P)H nitroreductase rutEP75894RUTE_ECOLIrutEhttp://ecmdb.ca/proteins/P75894.xmlNADP-dependent L-serine/L-allo-threonine dehydrogenase ydfGP39831YDFG_ECOLIydfGhttp://ecmdb.ca/proteins/P39831.xmlProtein rutDP75895RUTD_ECOLIrutDhttp://ecmdb.ca/proteins/P75895.xmlHydrogen ion + Malonic semialdehyde + NADPH > 3-Hydroxypropanoate + NADPR09289RXN-89743-Aminoacrylate + Hydrogen ion + Water > Malonic semialdehyde + Ammoniumbeta-Alanine + alpha-Ketoglutarate <> Malonic semialdehyde + L-GlutamateR009083-Hydroxypropanoate + NADP <> Malonic semialdehyde + NADPH + Hydrogen ionR092893-Aminoacrylate + Water <> Malonic semialdehyde + AmmoniaR09983RXN0-64523-Aminoacrylate + Water > Malonic semialdehyde + AmmoniaRXN0-64523-Hydroxypropanoate + NADP < Malonic semialdehyde + NADPH + Hydrogen ionRXN-89743-Hydroxypropanoate + NADP > Malonic semialdehyde + NADPH2-Aminoacrylic acid + Water + Hydrogen ion > Malonic semialdehyde + AmmoniumPW_R005909beta-Alanine + alpha-Ketoglutarate <> Malonic semialdehyde + L-GlutamateHydrogen ion + Malonic semialdehyde + NADPH >3 3-Hydroxypropanoate + NADPHydrogen ion + Malonic semialdehyde + NADPH >3 3-Hydroxypropanoate + NADP