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Record Information
Version	2.0
Creation Date	2012-08-09 09:16:15 -0600
Update Date	2015-09-13 15:15:33 -0600
Secondary Accession Numbers	ECMDB21441
Identification
Name:	N-Acetylserine
Description	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).
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa4153ae8> Close
Synonyms:	(2S)-2-Acetamido-3-hydroxypropanoate (2S)-2-Acetamido-3-hydroxypropanoic acid Acetylserine N-acetyl-L-Serine N-Aceyl-L-serine
Chemical Formula:	C5H9NO4
Weight:	Average: 147.1293 Monoisotopic: 147.053157781
InChI Key:	JJIHLJJYMXLCOY-BYPYZUCNSA-N
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
CAS number:	16354-58-8
IUPAC Name:	(2S)-2-acetamido-3-hydroxypropanoic acid
Traditional IUPAC Name:	acetylserine
SMILES:	CC(=O)N[C@@H](CO)C(O)=O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom.
Kingdom	Organic compounds
Super Class	Organic acids and derivatives
Class	Carboxylic acids and derivatives
Sub Class	Amino acids, peptides, and analogues
Direct Parent	N-acyl-L-alpha-amino acids
Alternative Parents	Serine and derivatives Beta hydroxy acids and derivatives Acetamides Secondary carboxylic acid amides Monocarboxylic acids and derivatives Carboxylic acids Primary alcohols Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
Substituents	N-acyl-l-alpha-amino acid Serine or derivatives Beta-hydroxy acid Hydroxy acid Acetamide Carboxamide group Secondary carboxylic acid amide Carboxylic acid Monocarboxylic acid or derivatives Primary alcohol Organooxygen compound Organonitrogen compound Organopnictogen compound Alcohol Organic oxygen compound Carbonyl group Organic nitrogen compound Organic oxide Hydrocarbon derivative Aliphatic acyclic compound
Molecular Framework	Aliphatic acyclic compounds
External Descriptors	N-acetyl-L-amino acid (CHEBI:45441 ) acetyl-L-serine (CHEBI:45441 )
Physical Properties
State:	Solid
Charge:	-1
Melting point:	207.6 °C
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 84.6 g/L ALOGPS logP -1.4 ALOGPS logP -1.8 ChemAxon logS -0.24 ALOGPS pKa (Strongest Acidic) 3.61 ChemAxon pKa (Strongest Basic) -2 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 86.63 Ų ChemAxon Rotatable Bond Count 3 ChemAxon Refractivity 31.48 m³·mol⁻¹ ChemAxon Polarizability 13.43 ų ChemAxon Number of Rings 0 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:
SMPDB Pathways:	Not Available
KEGG Pathways:	Not Available
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key GC-MS GC-MS Spectrum - GC-MS (2 TMS) splash10-0v4r-1910000000-55bfa57992b993e5736a View in MoNA GC-MS GC-MS Spectrum - GC-MS (Non-derivatized) splash10-0v4r-1910000000-55bfa57992b993e5736a View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-0006-9300000000-6b0aa9c8cd5d65af598e View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive splash10-00dl-9640000000-e19818dfd1f671358afc View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer LC-MS/MS LC-MS/MS Spectrum - 20V, Negative splash10-00ec-9000000000-ea3c1cb050105f5513c0 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 10V, Negative splash10-00ea-9300000000-ecc32dc021c318a085a1 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 30V, Negative splash10-006x-9000000000-ec47f807a87862b61560 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 40V, Negative splash10-0006-9000000000-6b0d326c6e06fd4000da View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-001j-2900000000-cbbd7e861694a1b35ef0 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0il9-9500000000-450a2fd0cc806534a001 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-001c-9000000000-92b250da801d4279b0ce View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0f6t-2900000000-4a518dea349294701f1d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0ugs-9800000000-1fd980296f0d35c624aa View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0a4l-9100000000-b2ff3e9d761c45d69c15 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0bt9-7900000000-2b2025d17af2e7713b6d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-03dr-9200000000-168efcb7664c27577d54 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-03dl-9000000000-5f40a5d675fc08643864 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-00di-9300000000-9296333e726065a0a297 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-05fr-9100000000-04b2db5af6f8b258f271 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0006-9000000000-e1a13303be43e1757dfa View in MoNA 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 2D NMR [1H,13C] 2D NMR Spectrum Not Available View in JSpectraViewer
References
References:	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. Pubmed: 8389858 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. Pubmed: 17723438 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. Pubmed: 8166630 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. Pubmed: 16465618 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. Pubmed: 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. Pubmed: 16274666 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. Pubmed: 18402659
Synthesis Reference:	Tsurumi, Kohti; Yamada, Sakae. L-Serine from D-glucosamine. Tohoku Journal of Experimental Medicine (1955), 62 329-31.
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 45441 HMDB ID HMDB02931 Pubchem Compound ID 65249 Kegg ID Not Available ChemSpider ID 58744 Wikipedia Acetylserine BioCyc ID Not Available Ligand Expo SAC