2.0 2012-05-31 13:55:18 -0600 2015-09-13 12:56:12 -0600 ECMDB02064 M2MDB000434 N-Acetylputrescine N-Acetylputrescine is the N-acetylated form of the naturally occurring polyamine called putrescine. The N-acetylation is mediated by the enzyme diamine N-acetyltransferase. Putrescine is related to cadaverine (another polyamine). Both are produced by the breakdown of amino acids in living and dead organisms and both are toxic in large doses. Putrescine and cadaverine are largely responsible for the foul odor of putrefying flesh. Putrescine attacks s-adenosyl methionine and converts it to spermidine. Spermidine in turn attacks another s-adenosyl methionine and converts it to spermine. Putrescine is synthesized in small quantities by healthy living cells by the action of ornithine decarboxylase. Acetylputrescine Monoacetylputrescine N-(4-Aminobutyl)acetamide C6H14N2O 130.1882 130.11061308 N-(4-aminobutyl)acetamide acetylputrescine 18233-70-0 CC(=O)NCCCCN InChI=1S/C6H14N2O/c1-6(9)8-5-3-2-4-7/h2-5,7H2,1H3,(H,8,9) KLZGKIDSEJWEDW-UHFFFAOYSA-N Solid Cytoplasm Periplasm logp -0.84 ALOGPS logs 0.04 ALOGPS solubility 1.41e+02 g/l ALOGPS logp -1 ChemAxon pka_strongest_acidic 16.48 ChemAxon pka_strongest_basic 9.9 ChemAxon iupac N-(4-aminobutyl)acetamide ChemAxon average_mass 130.1882 ChemAxon mono_mass 130.11061308 ChemAxon smiles CC(=O)NCCCCN ChemAxon formula C6H14N2O ChemAxon inchi InChI=1S/C6H14N2O/c1-6(9)8-5-3-2-4-7/h2-5,7H2,1H3,(H,8,9) ChemAxon inchikey KLZGKIDSEJWEDW-UHFFFAOYSA-N ChemAxon polar_surface_area 55.12 ChemAxon refractivity 36.82 ChemAxon polarizability 15.28 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 2 ChemAxon donor_count 2 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon Arginine and proline metabolism ec00330 Specdb::CMs 804 Specdb::CMs 805 Specdb::CMs 806 Specdb::CMs 1376 Specdb::CMs 1409 Specdb::CMs 2521 Specdb::CMs 30390 Specdb::CMs 30922 Specdb::CMs 30923 Specdb::CMs 31387 Specdb::CMs 31388 Specdb::CMs 31691 Specdb::CMs 31692 Specdb::CMs 136305 Specdb::CMs 144039 Specdb::NmrOneD 1844 Specdb::MsMs 1975 Specdb::MsMs 1976 Specdb::MsMs 1977 Specdb::MsMs 5694 Specdb::MsMs 5695 Specdb::MsMs 5696 Specdb::MsMs 5697 Specdb::MsMs 5698 Specdb::MsMs 5702 Specdb::MsMs 178338 Specdb::MsMs 178339 Specdb::MsMs 178340 Specdb::MsMs 180654 Specdb::MsMs 180655 Specdb::MsMs 180656 Specdb::MsMs 445591 Specdb::MsMs 445592 Specdb::MsMs 445593 Specdb::MsMs 445594 Specdb::MsMs 445595 Specdb::MsMs 448116 Specdb::MsMs 451940 Specdb::MsMs 2231076 Specdb::MsMs 2233107 Specdb::MsMs 2239726 Specdb::NmrTwoD 1784 HMDB02064 122356 109095 C02714 17768 CPD-569 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 Loser C, Folsch UR, Paprotny C, Creutzfeldt W: Polyamines in colorectal cancer. Evaluation of polyamine concentrations in the colon tissue, serum, and urine of 50 patients with colorectal cancer. Cancer. 1990 Feb 15;65(4):958-66. 2297664 Lee SH, Suh JW, Chung BC, Kim SO: Polyamine profiles in the urine of patients with leukemia. Cancer Lett. 1998 Jan 9;122(1-2):1-8. 9464484 Abdel-Monem MM, Ohno K: Polyamine metabolism I: Synthesis of dansyl derivatives of N-(monoaminoalkyl)- and N-(polyaminoalkyl)acetamides and elucidation in urine of a cancer patient. J Pharm Sci. 1977 Aug;66(8):1089-94. 197226 Hiramatsu K, Sugimoto M, Kamei S, Hoshino M, Kinoshita K, Iwasaki K, Kawakita M: Determination of amounts of polyamines excreted in urine: demonstration of N1,N8-diacetylspermidine and N1,N12-diacetylspermine as components commonly occurring in normal human urine. J Biochem (Tokyo). 1995 Jan;117(1):107-12. 7775374 Hiramatsu K, Kamei S, Sugimoto M, Kinoshita K, Iwasaki K, Kawakita M: An improved method of determining free and acetylated polyamines by HPLC involving an enzyme reactor and an electrochemical detector. J Biochem (Tokyo). 1994 Mar;115(3):584-9. 8056776 http://hmdb.ca/system/metabolites/msds/000/001/647/original/HMDB02064.pdf?1358461912 Spermidine N(1)-acetyltransferase P0A951 ATDA_ECOLI speG http://ecmdb.ca/proteins/P0A951.xml Acetyl-CoA + Putrescine <> Coenzyme A + N-Acetylputrescine R01154