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Record Information
Version	2.0
Creation Date	2012-05-31 13:46:14 -0600
Update Date	2015-06-03 15:53:46 -0600
Secondary Accession Numbers	ECMDB01138
Identification
Name:	N-Acetyl-L-alanine
Description	N-Acetyl-L-alanine is a product that can be formed spontaneously by the reaction of pyruvate with ammonia. The enzyme phenylalanine N-acetyltransferase (EC 2.3.1.53) can also generate this molecule from Acetyl-CoA and Alanine.
Structure	MOLSDF3D-SDFPDBSMILESInChI View 3D Structure × Structure for #<Compound:0xa791ac38> Close
Synonyms:	(S)-(-)-N-Acetylalanine (S)-N-Acetylalanine Acetyl-L-alanine Acetylalanine L-N-Acetylalanine N-Acetyl-(S)-alanine N-Acetyl-L-alanine N-Acetylalanine
Chemical Formula:	C5H9NO3
Weight:	Average: 131.1299 Monoisotopic: 131.058243159
InChI Key:	KTHDTJVBEPMMGL-VKHMYHEASA-N
InChI:	InChI=1S/C5H9NO3/c1-3(5(8)9)6-4(2)7/h3H,1-2H3,(H,6,7)(H,8,9)/t3-/m0/s1
CAS number:	97-69-8
IUPAC Name:	(2S)-2-acetamidopropanoic acid
Traditional IUPAC Name:	N-acetylalanine
SMILES:	C[C@H](NC(C)=O)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	Alanine and derivatives Acetamides Secondary carboxylic acid amides Monocarboxylic acids and derivatives Carboxylic acids Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
Substituents	N-acyl-l-alpha-amino acid Alanine or derivatives Acetamide Carboxamide group Secondary carboxylic acid amide Carboxylic acid Monocarboxylic acid or derivatives Organopnictogen compound Organic oxygen compound Organooxygen compound Organonitrogen compound Carbonyl group Organic nitrogen compound Organic oxide Hydrocarbon derivative Aliphatic acyclic compound
Molecular Framework	Aliphatic acyclic compounds
External Descriptors	L-alanine derivative (CHEBI:40992 ) N-acetyl-L-amino acid (CHEBI:40992 )
Physical Properties
State:	Solid
Charge:	-1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 43.6 g/L ALOGPS logP -0.53 ALOGPS logP -0.76 ChemAxon logS -0.48 ALOGPS pKa (Strongest Acidic) 3.89 ChemAxon pKa (Strongest Basic) -2 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 3 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 66.4 Ų ChemAxon Rotatable Bond Count 2 ChemAxon Refractivity 29.94 m³·mol⁻¹ ChemAxon Polarizability 12.5 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:	Acetyl-CoA + L-Glutamate <> N-Acetyl-L-alanine + Coenzyme A + Hydrogen ion + N-Acetylglutamic acid N-Acetyl-L-alanine + Adenosine triphosphate + N-Acetylglutamic acid <> N-Acetyl-L-glutamyl 5-phosphate + ADP Acetyl-CoA + L-Glutamate <> Coenzyme A + N-Acetyl-L-alanine Adenosine triphosphate + N-Acetyl-L-alanine <> ADP + N-Acetyl-L-glutamyl 5-phosphate Acetyl-CoA + L-Glutamic acid + L-Glutamate <> N-Acetyl-L-alanine + Coenzyme A + Hydrogen ion + N-Acetylglutamic acid + N-Acetyl-L-alanine + N-Acetylglutamic acid Acetyl-CoA + L-Glutamate <> N-Acetyl-L-alanine + Coenzyme A + Hydrogen ion + N-Acetylglutamic acid N-Acetyl-L-alanine + Adenosine triphosphate + N-Acetylglutamic acid <> N-Acetyl-L-glutamyl 5-phosphate + ADP
SMPDB Pathways:	L-glutamate metabolism II PW001886
KEGG Pathways:	Arginine and proline metabolism ec00330
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key GC-MS GC-MS Spectrum - GC-MS (1 TMS) splash10-05n0-2900000000-c0a5e66723f41ac78751 View in MoNA GC-MS GC-MS Spectrum - GC-MS (Non-derivatized) splash10-05n0-2900000000-c0a5e66723f41ac78751 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-0006-9000000000-82510327b6f9313f2dec View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive splash10-00di-9200000000-5c8085960ac907268dee View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive Not Available View in JSpectraViewer LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) splash10-0006-9000000000-4cea4517104b7a324deb View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) splash10-0006-9000000000-4497242e6b422cf3f913 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) splash10-0006-9000000000-22d764f7b773b82c6515 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-IT , negative splash10-000i-9000000000-e6becb5f8b8bbb53304a View in MoNA LC-MS/MS LC-MS/MS Spectrum - 10V, Negative splash10-000i-9000000000-0aae7c100ca236c5d9ff View in MoNA LC-MS/MS LC-MS/MS Spectrum - 35V, Negative splash10-000i-9000000000-a834937166d1b13573af View in MoNA LC-MS/MS LC-MS/MS Spectrum - 20V, Negative splash10-000i-9000000000-64d13cbfedb6b9468f0f View in MoNA LC-MS/MS LC-MS/MS Spectrum - 40V, Negative splash10-0079-9500000000-47ed2f6ecfc2c07a7238 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 10V, Positive splash10-0006-9000000000-381b773ca35cc4fcd019 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 20V, Positive splash10-0006-9000000000-5f8b9c01b2c31f02a57c View in MoNA LC-MS/MS LC-MS/MS Spectrum - 40V, Positive splash10-0006-9000000000-bb702a57406742ce92fd View in MoNA LC-MS/MS LC-MS/MS Spectrum - 35V, Positive splash10-0006-9000000000-bcbc1b15a23596134e9b View in MoNA LC-MS/MS LC-MS/MS Spectrum - 20V, Positive splash10-0006-9000000000-dcbe526c53d0cc355023 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 10V, Positive splash10-0006-9000000000-9c03cb4f6a9e3f4d7d8d View in MoNA LC-MS/MS LC-MS/MS Spectrum - 40V, Positive splash10-0006-9000000000-7ab7ce4fbeeaa4906786 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 35V, Negative splash10-000i-9000000000-f747c686b81495308cfc View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0019-9600000000-98787fdcdf179af3efc6 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-000f-9000000000-c9b855453cf3c68830bf View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0006-9000000000-4178e09fa261bbb5e7e9 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-001i-4900000000-2739a6e8536aca9442cc View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-000i-9200000000-2df5117d1f0498fa4d47 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0076-9000000000-74175a91d6530fa275df View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-000l-9100000000-5c3ebb626b607f2771cb View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-006x-9000000000-3526994d54c9aef41949 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0006-9000000000-527b4afd5857c451f463 View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 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 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 2D NMR [1H,1H] 2D NMR Spectrum Not Available View in JSpectraViewer 2D NMR [1H,13C] 2D NMR Spectrum Not Available View in JSpectraViewer
References
References:	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. Pubmed: 22080510
Synthesis Reference:	Vanzura, Jiri; Kasafirek, Evzen; Hrabalek, Alexandr; Vinsova, Jarmila; Krepelka, Jiri. Process for preparing highly pure N-acetyl-L- or -D-alanine. Czech. (1989), 4 pp.
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 17533 HMDB ID HMDB00766 Pubchem Compound ID 7345 Kegg ID Not Available ChemSpider ID 79449 Wikipedia ID Not Available BioCyc ID Not Available Ligand Expo AYA

Enzymes