2.0 2012-07-30 14:55:07 -0600 2015-09-13 15:15:31 -0600 ECMDB21254 M2MDB001662 N8-Acetylspermidine N8-Acetylspermidine is a polyamine. The polyamines, found in virtually all living organisms, are a ubiquitous group of compounds that appear to play a vital role in many cellular processes involving nucleic acids including cell growth and differentiation. The polyamines, found in virtually all living organisms, are a ubiquitous group of compounds that appear to play a vital role in many cellular processes involving nucleic acids including cell growth and differentiation. Acetylation on the terminal nitrogen adjacent to the 4-carbon chain produces N8-acetylspermidine. This reaction is catalyzed by spermidine N8-acetyltransferase and does not result in the conversion of spermidine to putrescine but, instead, the product undergoes deacetylation. N-[4-(3-Aminopropylamino)butyl]acetamide N-[4-[(3-Aminopropyl)amino]butyl]-Acetamide N-{4-[(3-Aminopropyl)amino]butyl}acetamide N8-Acetylspermidine N8-monoacetylspermidine C9H21N3O 187.2825 187.168462309 N-{4-[(3-aminopropyl)amino]butyl}acetamide N8-acetylspermidine 13431-24-8 CC(=O)NCCCCNCCCN InChI=1S/C9H21N3O/c1-9(13)12-8-3-2-6-11-7-4-5-10/h11H,2-8,10H2,1H3,(H,12,13) FONIWJIDLJEJTL-UHFFFAOYSA-N Solid Cytosol logp -0.48 ALOGPS logs -1.63 ALOGPS solubility 4.40e+00 g/l ALOGPS melting_point 202-203 oC logp -1.3 ChemAxon pka_strongest_acidic 16.53 ChemAxon pka_strongest_basic 10.29 ChemAxon iupac N-{4-[(3-aminopropyl)amino]butyl}acetamide ChemAxon average_mass 187.2825 ChemAxon mono_mass 187.168462309 ChemAxon smiles CC(=O)NCCCCNCCCN ChemAxon formula C9H21N3O ChemAxon inchi InChI=1S/C9H21N3O/c1-9(13)12-8-3-2-6-11-7-4-5-10/h11H,2-8,10H2,1H3,(H,12,13) ChemAxon inchikey FONIWJIDLJEJTL-UHFFFAOYSA-N ChemAxon polar_surface_area 67.15 ChemAxon refractivity 54.41 ChemAxon polarizability 23.1 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 3 ChemAxon donor_count 3 ChemAxon physiological_charge 2 ChemAxon formal_charge 0 ChemAxon S-adenosyl-L-methionine biosynthesis S-adenosyl-L-methionine biosynthesis(SAM) is synthesized in the cytosol of the cell from L-methionine and ATP. This reaction is catalyzed by methionine adenosyltransferase. L methione is taken up from the environment through a complex reaction coupled transport and then proceeds too synthesize the s adenosylmethionine through a adenosylmethionine synthase. The S-adenosylmethionine then interacts with a hydrogen ion through a adenosylmethionine decarboxylase resulting in a carbon dioxide and a S-adenosyl 3-methioninamine.This compound interacts with a putrescine through a spermidine synthase resulting in a spermidine, a hydrogen ion and a S-methyl-5'-thioadenosine. The latter compound is degraded by interacting with a water molecule through a 5' methylthioadenosine nucleosidase resulting in a adenine and a S-methylthioribose which is then release into the environment PW000837 Metabolic Specdb::CMs 2800 Specdb::CMs 157667 Specdb::NmrOneD 328232 Specdb::NmrOneD 328233 Specdb::NmrOneD 328234 Specdb::NmrOneD 328235 Specdb::NmrOneD 328236 Specdb::NmrOneD 328237 Specdb::NmrOneD 328238 Specdb::NmrOneD 328239 Specdb::NmrOneD 328240 Specdb::NmrOneD 328241 Specdb::NmrOneD 328242 Specdb::NmrOneD 328243 Specdb::NmrOneD 328244 Specdb::NmrOneD 328245 Specdb::NmrOneD 328246 Specdb::NmrOneD 328247 Specdb::NmrOneD 328248 Specdb::NmrOneD 328249 Specdb::NmrOneD 328250 Specdb::NmrOneD 328251 Specdb::MsMs 445676 Specdb::MsMs 445677 Specdb::MsMs 445678 Specdb::MsMs 445679 Specdb::MsMs 445680 Specdb::MsMs 2236905 Specdb::MsMs 31904 Specdb::MsMs 31905 Specdb::MsMs 31906 Specdb::MsMs 2364922 Specdb::MsMs 2364923 Specdb::MsMs 2364924 Specdb::MsMs 25346 Specdb::MsMs 25347 Specdb::MsMs 25348 Specdb::MsMs 2597737 Specdb::MsMs 2597738 Specdb::MsMs 2597739 HMDB02189 123689 110264 C01029 27911 CPD-3462 Q9C Hrushesky WJ, Merdink J, Abdel-Monem MM: Circadian rhythmicity of polyamine urinary excretion. Cancer Res. 1983 Aug;43(8):3944-7. 6861156 Seiler N, Graham A, Bartholeyns J: Enhanced urinary excretion of N1-acetylspermidine and the presence of tumors. Cancer Res. 1981 Apr;41(4):1572-3. 6897929 Abdel-Monem MM, Merdink JL, Theologides A: Urinary excretion of monoacetyl polyamines in patients with non-Hodgkin's lymphoma. Cancer Res. 1982 May;42(5):2097-8. 7066912 Inoue H, Fukunaga K, Munemura S, Tsuruta Y: Simultaneous determination of free and N-acetylated polyamines in urine by semimicro high-performance liquid chromatography using 4-(5,6-dimethoxy-2-phthalimidinyl)-2-methoxyphenylsulfonyl chloride as a fluorescent labeling reagent. Anal Biochem. 2005 Apr 15;339(2):191-7. 15797558 Mudumba S, Menezes A, Fries D, Blankenship J: Differentiation of PC12 cells induced by N8-acetylspermidine and by N8-acetylspermidine deacetylase inhibition. Biochem Pharmacol. 2002 Jun 1;63(11):2011-8. 12093478 Tabor, Herbert; Tabor, Celia W.; De Meis, Leopold. Chemical synthesis of N-acetyl-1,4-diaminobutane, N1-acetylspermidine, and N8-acetylspermidine. Methods Enzymol. (1971), 17(Pt. B), 829-33. Spermidine N(1)-acetyltransferase P0A951 ATDA_ECOLI speG http://ecmdb.ca/proteins/P0A951.xml Acetyl-CoA + Spermidine > Coenzyme A + Hydrogen ion + N8-Acetylspermidine