2.0 2012-08-09 09:16:15 -0600 2015-09-13 15:15:33 -0600 ECMDB21441 M2MDB001836 N-Acetylserine N-acetylserine is an acetylated amino acid. Acetylation of the N-terminal amino acid (-NH2 acetylation) is a common protein modification in eukaryotes but is rarely encountered in prokaryotes. N-acetylserine an activator for cysteine synthesis in E. coli (via cysB). (2S)-2-Acetamido-3-hydroxypropanoate (2S)-2-Acetamido-3-hydroxypropanoic acid Acetylserine N-acetyl-L-Serine N-Aceyl-L-serine C5H9NO4 147.1293 147.053157781 (2S)-2-acetamido-3-hydroxypropanoic acid acetylserine 16354-58-8 CC(=O)N[C@@H](CO)C(O)=O InChI=1S/C5H9NO4/c1-3(8)6-4(2-7)5(9)10/h4,7H,2H2,1H3,(H,6,8)(H,9,10)/t4-/m0/s1 JJIHLJJYMXLCOY-BYPYZUCNSA-N Solid Cytoplasm logp -1.36 ALOGPS logs -0.24 ALOGPS solubility 8.46e+01 g/l ALOGPS melting_point 207.6 oC logp -1.8 ChemAxon pka_strongest_acidic 3.61 ChemAxon pka_strongest_basic -2 ChemAxon iupac (2S)-2-acetamido-3-hydroxypropanoic acid ChemAxon average_mass 147.1293 ChemAxon mono_mass 147.053157781 ChemAxon smiles CC(=O)N[C@@H](CO)C(O)=O ChemAxon formula C5H9NO4 ChemAxon inchi InChI=1S/C5H9NO4/c1-3(8)6-4(2-7)5(9)10/h4,7H,2H2,1H3,(H,6,8)(H,9,10)/t4-/m0/s1 ChemAxon inchikey JJIHLJJYMXLCOY-BYPYZUCNSA-N ChemAxon polar_surface_area 86.63 ChemAxon refractivity 31.48 ChemAxon polarizability 13.43 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 1191 Specdb::CMs 13411 Specdb::CMs 31434 Specdb::CMs 38501 Specdb::CMs 161559 Specdb::NmrOneD 1917 Specdb::NmrOneD 129118 Specdb::NmrOneD 129119 Specdb::NmrOneD 129120 Specdb::NmrOneD 129121 Specdb::NmrOneD 129122 Specdb::NmrOneD 129123 Specdb::NmrOneD 129124 Specdb::NmrOneD 129125 Specdb::NmrOneD 129126 Specdb::NmrOneD 129127 Specdb::NmrOneD 129128 Specdb::NmrOneD 129129 Specdb::NmrOneD 129130 Specdb::NmrOneD 129131 Specdb::NmrOneD 129132 Specdb::NmrOneD 129133 Specdb::NmrOneD 129134 Specdb::NmrOneD 129135 Specdb::NmrOneD 129136 Specdb::NmrOneD 129137 Specdb::MsMs 29741 Specdb::MsMs 29742 Specdb::MsMs 29743 Specdb::MsMs 36299 Specdb::MsMs 36300 Specdb::MsMs 36301 Specdb::MsMs 2239946 Specdb::MsMs 2241747 Specdb::MsMs 2242064 Specdb::MsMs 2243823 Specdb::MsMs 2309241 Specdb::MsMs 2309242 Specdb::MsMs 2309243 Specdb::MsMs 2656381 Specdb::MsMs 2656382 Specdb::MsMs 2656383 Specdb::NmrTwoD 1852 HMDB02931 65249 58744 SAC Acetylserine Vijayendran, C., Barsch, A., Friehs, K., Niehaus, K., Becker, A., Flaschel, E. (2008). "Perceiving molecular evolution processes in Escherichia coli by comprehensive metabolite and gene expression profiling." Genome Biol 9:R72. 18402659 Sugahara K, Zhang J, Kodama H: Liquid chromatographic-mass spectrometric analysis of N-acetylamino acids in human urine. J Chromatogr B Biomed Appl. 1994 Jul 1;657(1):15-21. 7952062 Van Coster RN, Gerlo EA, Giardina TG, Engelke UF, Smet JE, De Praeter CM, Meersschaut VA, De Meirleir LJ, Seneca SH, Devreese B, Leroy JG, Herga S, Perrier JP, Wevers RA, Lissens W: Aminoacylase I deficiency: a novel inborn error of metabolism. Biochem Biophys Res Commun. 2005 Dec 23;338(3):1322-6. Epub 2005 Nov 2. 16274666 Sass JO, Mohr V, Olbrich H, Engelke U, Horvath J, Fliegauf M, Loges NT, Schweitzer-Krantz S, Moebus R, Weiler P, Kispert A, Superti-Furga A, Wevers RA, Omran H: Mutations in ACY1, the gene encoding aminoacylase 1, cause a novel inborn error of metabolism. Am J Hum Genet. 2006 Mar;78(3):401-9. Epub 2006 Jan 18. 16465618 Boesgaard S, Aldershvile J, Poulsen HE, Christensen S, Dige-Petersen H, Giese J: N-acetylcysteine inhibits angiotensin converting enzyme in vivo. J Pharmacol Exp Ther. 1993 Jun;265(3):1239-44. 8389858 Lynch AS, Tyrrell R, Smerdon SJ, Briggs GS, Wilkinson AJ: Characterization of the CysB protein of Klebsiella aerogenes: direct evidence that N-acetylserine rather than O-acetylserine serves as the inducer of the cysteine regulon. Biochem J. 1994 Apr 1;299 ( Pt 1):129-36. 8166630 Gerlo E, Van Coster R, Lissens W, Winckelmans G, De Meirleir L, Wevers R: Gas chromatographic-mass spectrometric analysis of N-acetylated amino acids: the first case of aminoacylase I deficiency. Anal Chim Acta. 2006 Jul 7;571(2):191-9. Epub 2006 May 5. 17723438 Tsurumi, Kohti; Yamada, Sakae. L-Serine from D-glucosamine. Tohoku Journal of Experimental Medicine (1955), 62 329-31.