N-Acetyl-L-alanine (ECMDB01138) (M2MDB000272)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (4)
Record Information
Version2.0
Creation Date2012-05-31 13:46:14 -0600
Update Date2015-06-03 15:53:46 -0600
Secondary Accession Numbers
  • ECMDB01138
Identification
Name:N-Acetyl-L-alanine
DescriptionN-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
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-L-alpha-amino acids
Alternative Parents
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 FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility43.6 g/LALOGPS
logP-0.53ALOGPS
logP-0.76ChemAxon
logS-0.48ALOGPS
pKa (Strongest Acidic)3.89ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity29.94 m³·mol⁻¹ChemAxon
Polarizability12.5 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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 IIPW001886 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Arginine and proline metabolism ec00330
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-05n0-2900000000-c0a5e66723f41ac78751View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-05n0-2900000000-c0a5e66723f41ac78751View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-82510327b6f9313f2decView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9200000000-5c8085960ac907268deeView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0006-9000000000-4cea4517104b7a324debView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-4497242e6b422cf3f913View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-22d764f7b773b82c6515View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-000i-9000000000-e6becb5f8b8bbb53304aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-0aae7c100ca236c5d9ffView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-000i-9000000000-a834937166d1b13573afView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-64d13cbfedb6b9468f0fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0079-9500000000-47ed2f6ecfc2c07a7238View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-381b773ca35cc4fcd019View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-5f8b9c01b2c31f02a57cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-bb702a57406742ce92fdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0006-9000000000-bcbc1b15a23596134e9bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-dcbe526c53d0cc355023View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-9c03cb4f6a9e3f4d7d8dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-7ab7ce4fbeeaa4906786View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-000i-9000000000-f747c686b81495308cfcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0019-9600000000-98787fdcdf179af3efc6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000f-9000000000-c9b855453cf3c68830bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-4178e09fa261bbb5e7e9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-4900000000-2739a6e8536aca9442ccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9200000000-2df5117d1f0498fa4d47View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0076-9000000000-74175a91d6530fa275dfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000l-9100000000-5c3ebb626b607f2771cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-9000000000-3526994d54c9aef41949View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-527b4afd5857c451f463View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView 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
External Links:
ResourceLink
CHEBI ID17533
HMDB IDHMDB00766
Pubchem Compound ID7345
Kegg IDNot Available
ChemSpider ID79449
Wikipedia IDNot Available
BioCyc IDNot Available
Ligand ExpoAYA

Enzymes

Protein Details
1. Amino-acid acetyltransferase
General function:
Involved in cellular amino acid biosynthetic process
Specific function:
Acetyl-CoA + L-glutamate = CoA + N-acetyl-L- glutamate
Gene Name:
argA
Uniprot ID:
P0A6C5
Molecular weight:
49195
Reactions
Acetyl-CoA + L-glutamate = CoA + N-acetyl-L-glutamate.
Protein Details
2. Acetylglutamate kinase
General function:
Involved in acetylglutamate kinase activity
Specific function:
ATP + N-acetyl-L-glutamate = ADP + N-acetyl-L- glutamate 5-phosphate
Gene Name:
argB
Uniprot ID:
P0A6C8
Molecular weight:
27159
Reactions
ATP + N-acetyl-L-glutamate = ADP + N-acetyl-L-glutamate 5-phosphate.