2.0 2012-05-31 13:44:48 -0600 2015-06-04 15:14:16 -0600 ECMDB01080 M2MDB000246 4-Aminobutyraldehyde 4-Aminobutyraldehyde is a metabolite of putrescine. In both arginine and proline metabolism, and beta-alanine metabolism, it is a substrate of aminobutyraldehyde dehydrogenase [EC:1.2.1.19]. It is converted to 4-aminobutanoate. (KEGG) &gamma;-aminobutyraldehyde 4-Amino-butanal 4-Amino-butyraldehyde 4-Aminobutanal 4-Aminobutyraldehyde ABAL g-Aminobutyraldehyde Gamma-Aminobutyraldehyde γ-Aminobutyraldehyde C4H9NO 87.1204 87.068413915 4-aminobutanal ω-aminoaldehyde 4390-05-0 NCCCC=O InChI=1S/C4H9NO/c5-3-1-2-4-6/h4H,1-3,5H2 DZQLQEYLEYWJIB-UHFFFAOYSA-N Solid Cytosol logp -0.73 ALOGPS logs 0.47 ALOGPS solubility 2.59e+02 g/l ALOGPS logp -0.78 ChemAxon pka_strongest_acidic 14.83 ChemAxon pka_strongest_basic 9.79 ChemAxon iupac 4-aminobutanal ChemAxon average_mass 87.1204 ChemAxon mono_mass 87.068413915 ChemAxon smiles NCCCC=O ChemAxon formula C4H9NO ChemAxon inchi InChI=1S/C4H9NO/c5-3-1-2-4-6/h4H,1-3,5H2 ChemAxon inchikey DZQLQEYLEYWJIB-UHFFFAOYSA-N ChemAxon polar_surface_area 43.09 ChemAxon refractivity 24.53 ChemAxon polarizability 9.72 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon Arginine and proline metabolism ec00330 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 arginine metabolism The metabolism of L-arginine starts with the acetylation of L-glutamic acid resulting in a N-acetylglutamic acid while releasing a coenzyme A and a hydrogen ion. N-acetylglutamic acid is then phosphorylated via an ATP driven acetylglutamate kinase which yields a N-acetyl-L-glutamyl 5-phosphate. This compound undergoes a NDPH dependent reduction resulting in N-acetyl-L-glutamate 5-semialdehyde. This compound reacts with L-glutamic acid through a acetylornithine aminotransferase / N-succinyldiaminopimelate aminotransferase to produce a N-acetylornithine which is then deacetylated through a acetylornithine deacetylase which yield an ornithine. L-glutamine is used to synthesize carbamoyl phosphate through the interaction of L-glutamine, water, ATP, and hydrogen carbonate. This reaction yields ADP, L-glutamic acid, phosphate, and hydrogen ion. Carbamoyl phosphate and ornithine are used to catalyze the production of citrulline through an ornithine carbamoyltransferase. Citrulline reacts with L-aspartic acid through an ATP dependent enzyme, argininosuccinate synthase to produce pyrophosphate, AMP and argininosuccinic acid. Argininosussinic acid is then lyase to produce L-arginine and fumaric acid. L-arginine can be metabolized into succinic acid by two different sets of reactions: 1. Arginine reacts with succinyl-CoA through a arginine N-succinyltransferase resulting in N2-succinyl-L-arginine while releasing CoA and Hydrogen Ion. N2-succinyl-L-arginine is then dihydrolase to produce a N2-succinyl-L-ornithine through a N-succinylarginine dihydrolase. This compound in turn reacts with oxoglutaric acid through succinylornithine transaminase resulting in L-glutamic acid and N2-succinyl-L-glutamic acid 5-semialdehyde. This compoud in turn reacts with a NAD dependent dehydrogenase resulting in N2-succinylglutamate while releasing NADH and hydrogen ion. N2-succinylglutamate reacts with water through a succinylglutamate desuccinylase resulting in L-glutamic acid and a succinic acid. The succinic acid is then incorporated in the TCA cycle 2.Argine reacts with carbon dioxide and a hydrogen ion through a biodegradative arginine decarboxylase, resulting in Agmatine. This compound is then transformed into putrescine by reacting with water and an agmatinase, and releasing urea. Putrescine can be metabolized by reaction with either l-glutamic acid or oxoglutaric acid. If putrescine reacts with L-glutamic acid, it reacts through an ATP mediated gamma-glutamylputrescine producing a hydrogen ion, ADP, phosphate and gamma-glutamyl-L-putrescine. This compound is reduced by interacting with oxygen, water and a gamma-glutamylputrescine oxidoreductase resulting in ammonium, hydrogen peroxide and 4-gamma-glutamylamino butanal. This compound is dehydrogenated through a NADP mediated reaction lead by gamma-glutamyl-gamma-aminobutaryaldehyde dehydrogenase resulting in hydrogen ion, NADPH and 4-glutamylamino butanoate. In turn, the latter compound reacts with water through a gamma-glutamyl-gamma-aminobutyrate hydrolase resulting in L-glutamic acid and Gamma aminobutyric acid. On the other hand, if putrescine reacts with oxoglutaric acid through a putrescine aminotransferase, it results in L-glutamic acid, and a 4-aminobutyraldehyde. This compound reacts with water through a NAD dependent gamma aminobutyraldehyde dehydrogenase resulting in hydrogen ion, NADH and gamma-aminobutyric acid. Gamma Aaminobutyric acid reacts with oxoglutaric acid through 4-aminobutyrate aminotransferase resulting in L-glutamic acid and succinic acid semialdehyde. This compound in turn can react with with either NADP or NAD to result in the production of succinic acid through succinate-semialdehyde dehydrogenase or aldehyde dehydrogenase-like protein yneI respectively. Succinic acid can then be integrated in the TCA cycle. L-arginine is eventua lly metabolized into succinic acid which then goes to the TCA cycle PW000790 Metabolic ornithine metabolism In the ornithine biosynthesis pathway of E. coli, L-glutamate is acetylated to N-acetylglutamate by the enzyme N-acetylglutamate synthase, encoded by the argA gene. The acetyl donor for this reaction is acetyl-CoA. N-acetylglutamic acid is then phosphorylated via an ATP driven acetylglutamate kinase which yields a N-acetyl-L-glutamyl 5-phosphate. This compound undergoes a NADPH dependent reduction resulting in N-acetyl-L-glutamate 5-semialdehyde. This compound reacts with L-glutamic acid through a acetylornithine aminotransferase / N-succinyldiaminopimelate aminotransferase to produce a N-acetylornithine which is then deacetylated through a acetylornithine deacetylase which yield an ornithine. Ornithine interacts with hydrogen ion through a Ornithine decarboxylase resulting in a carbon dioxide release and a putrescine Putrescine can be metabolized by reaction with either l-glutamic acid or oxoglutaric acid. If putrescine reacts with L-glutamic acid, it reacts through an ATP mediated gamma-glutamylputrescine producing a hydrogen ion, ADP, phosphate and gamma-glutamyl-L-putrescine. This compound is reduced by interacting with oxygen, water and a gamma-glutamylputrescine oxidoreductase resulting in ammonium, hydrogen peroxide and 4-gamma-glutamylamino butanal. This compound is dehydrogenated through a NADP mediated reaction lead by gamma-glutamyl-gamma-aminobutaryaldehyde dehydrogenase resulting in hydrogen ion, NADPH and 4-glutamylamino butanoate. In turn, the latter compound reacts with water through a gamma-glutamyl-gamma-aminobutyrate hydrolase resulting in L-glutamic acid and Gamma aminobutyric acid. On the other hand, if putrescine reacts with oxoglutaric acid through a putrescine aminotransferase, it results in L-glutamic acid, and a 4-aminobutyraldehyde. This compound reacts with water through a NAD dependent gamma aminobutyraldehyde dehydrogenase resulting in hydrogen ion, NADH and gamma-aminobutyric acid. Gamma Aaminobutyric acid reacts with oxoglutaric acid through 4-aminobutyrate aminotransferase resulting in L-glutamic acid and succinic acid semialdehyde. This compound in turn can react with with either NADP or NAD to result in the production of succinic acid through succinate-semialdehyde dehydrogenase or aldehyde dehydrogenase-like protein yneI respectively. Succinic acid can then be integrated in the TCA cycle. PW000791 Metabolic putrescine degradation I PUTDEG-PWY Specdb::CMs 3453 Specdb::CMs 169790 Specdb::NmrOneD 8542 Specdb::NmrOneD 8543 Specdb::NmrOneD 8544 Specdb::NmrOneD 8545 Specdb::NmrOneD 8546 Specdb::NmrOneD 8547 Specdb::NmrOneD 8548 Specdb::NmrOneD 8549 Specdb::NmrOneD 8550 Specdb::NmrOneD 8551 Specdb::NmrOneD 8552 Specdb::NmrOneD 8553 Specdb::NmrOneD 8554 Specdb::NmrOneD 8555 Specdb::NmrOneD 8556 Specdb::NmrOneD 8557 Specdb::NmrOneD 8558 Specdb::NmrOneD 8559 Specdb::NmrOneD 8560 Specdb::NmrOneD 8561 Specdb::MsMs 25961 Specdb::MsMs 25962 Specdb::MsMs 25963 Specdb::MsMs 32519 Specdb::MsMs 32520 Specdb::MsMs 32521 Specdb::MsMs 3046498 Specdb::MsMs 3046499 Specdb::MsMs 3046500 Specdb::MsMs 3094489 Specdb::MsMs 3094490 Specdb::MsMs 3094491 HMDB01080 118 115 C00555 17769 4-AMINO-BUTYRALDEHYDE Keseler, I. 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Biochem J. 1996 May 15;316 ( Pt 1):317-24. 8645224 Kurys G, Shah PC, Kikonygo A, Reed D, Ambroziak W, Pietruszko R: Human aldehyde dehydrogenase. cDNA cloning and primary structure of the enzyme that catalyzes dehydrogenation of 4-aminobutyraldehyde. Eur J Biochem. 1993 Dec 1;218(2):311-20. 8269919 McPherson JD, Wasmuth JJ, Kurys G, Pietruszko R: Human aldehyde dehydrogenase: chromosomal assignment of the gene for the isozyme that metabolizes gamma-aminobutyraldehyde. Hum Genet. 1994 Feb;93(2):211-2. 8112751 Ambroziak W, Kurys G, Pietruszko R: Aldehyde dehydrogenase (EC 1.2.1.3): comparison of subcellular localization of the third isozyme that dehydrogenates gamma-aminobutyraldehyde in rat, guinea pig and human liver. Comp Biochem Physiol B. 1991;100(2):321-7. 1799975 Ambroziak W, Pietruszko R: Human aldehyde dehydrogenase: metabolism of putrescine and histamine. Alcohol Clin Exp Res. 1987 Dec;11(6):528-32. 3324802 Asakura, Tadashi; Takada, Koji; Ikeda, Yoshitaka; Matsuda, Makoto. Preparation of 4-aminobutyraldehyde and its properties on ion exchange chromatography. Jikeikai Medical Journal (1988), 35(1), 23-31. Putrescine aminotransferase P42588 PAT_ECOLI patA http://ecmdb.ca/proteins/P42588.xml Gamma-aminobutyraldehyde dehydrogenase P77674 ABDH_ECOLI ydcW http://ecmdb.ca/proteins/P77674.xml 4-Aminobutyraldehyde + Water + NAD <> gamma-Aminobutyric acid +2 Hydrogen ion + NADH R02549 AMINOBUTDEHYDROG-RXN alpha-Ketoglutarate + Putrescine > 4-Aminobutyraldehyde + L-Glutamate R01155 Putrescine + alpha-Ketoglutarate <> 4-Aminobutyraldehyde + L-Glutamate R01155 4-Aminobutyraldehyde + NAD + Water <> gamma-Aminobutyric acid + NADH + Hydrogen ion R02549 4-Aminobutyraldehyde > 1-Pyrroline + Water RXN-6423 4-Aminobutyraldehyde + NAD + Water > gamma-Aminobutyric acid + NADH + Hydrogen ion AMINOBUTDEHYDROG-RXN Putrescine + Oxoglutaric acid <> 4-Aminobutyraldehyde + L-Glutamate PUTTRANSAM-RXN 4-Aminobutyraldehyde + NAD + Water > gamma-Aminobutyric acid + NADH Ethylenediamine + alpha-Ketoglutarate + 4-Aminobutyraldehyde <> 1-Pyrroline + L-Glutamate + Water R10064 Putrescine + Oxoglutaric acid > L-Glutamic acid + 4-Aminobutyraldehyde + L-Glutamate PW_R002689