N-Acetyl-L-glutamate 5-semialdehyde (ECMDB06488) (M2MDB000675)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (4)XML
Proteins (827)
Record Information
Version2.0
Creation Date2012-05-31 14:08:37 -0600
Update Date2015-06-03 15:54:52 -0600
Secondary Accession Numbers
  • ECMDB06488
Identification
Name:N-Acetyl-L-glutamate 5-semialdehyde
DescriptionN-Acetyl-L-glutamate 5-semialdehyde is an intermediate in Urea cycle and metabolism of amino groups. N-Acetyl-L-glutamate 5-semialdehyde is the
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 2-Acetamido-5-oxopentanoate
  • 2-Acetamido-5-oxopentanoic acid
  • N-acetyl-L-glutamate semialdehyde
  • N-acetyl-L-glutamate-5-semialdehyde
  • N-acetylglutamate γ-semialdehyde
  • N-acetylglutamate semialdehyde
  • N-Acetyl-L-glutamate semialdehyde
  • N-Acetyl-L-glutamate-5-semialdehyde
  • N-Acetyl-L-glutamic acid 5-semialdehyde
  • N-Acetyl-L-glutamic acid semialdehyde
  • n-Acetyl-L-glutamic acid-5-semialdehyde
  • N-Acetyl-L-glutamic acid-5-semialdehyde
  • n-Acetylglutamate γ-semialdehyde
  • N-Acetylglutamate g-semialdehyde
  • N-Acetylglutamate gamma-semialdehyde
  • N-Acetylglutamate semialdehyde
  • N-Acetylglutamate γ-semialdehyde
  • n-Acetylglutamic acid γ-semialdehyde
  • N-Acetylglutamic acid g-semialdehyde
  • N-Acetylglutamic acid gamma-semialdehyde
  • N-Acetylglutamic acid semialdehyde
  • N-Acetylglutamic acid γ-semialdehyde
  • N-AcGlu-semialdehyde
Chemical Formula:C7H11NO4
Weight:Average: 173.1665
Monoisotopic: 173.068807845
InChI Key:BCPSFKBPHHBDAI-LURJTMIESA-N
InChI:InChI=1S/C7H11NO4/c1-5(10)8-6(7(11)12)3-2-4-9/h4,6H,2-3H2,1H3,(H,8,10)(H,11,12)/t6-/m0/s1
CAS number:13074-21-0
IUPAC Name:(2S)-2-acetamido-5-oxopentanoic acid
Traditional IUPAC Name:N-acetyl-5-oxo-L-norvaline
SMILES:CC(=O)N[C@@H](CCC=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
  • Fatty acid
  • Alpha-hydrogen aldehyde
  • Acetamide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Aldehyde
  • 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 Solubility18.6 g/LALOGPS
logP-0.43ALOGPS
logP-1.3ChemAxon
logS-0.97ALOGPS
pKa (Strongest Acidic)3.72ChemAxon
pKa (Strongest Basic)-1.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.47 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity39.81 m³·mol⁻¹ChemAxon
Polarizability16.46 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
N-Acetylornithine + alpha-Ketoglutarate <> N-Acetyl-L-glutamate 5-semialdehyde + L-Glutamate
N-Acetyl-L-glutamate 5-semialdehyde + Water > Acetic acid + L-Glutamic-gamma-semialdehyde
N-Acetyl-L-glutamate 5-semialdehyde + NADP + Phosphate <> N-Acetyl-L-glutamyl 5-phosphate + Hydrogen ion + NADPH
N-Acetylornithine + Oxoglutaric acid < N-Acetyl-L-glutamate 5-semialdehyde + L-Glutamate
N-Acetyl-L-glutamate 5-semialdehyde + NADP + Inorganic phosphate > N-Acetyl-L-glutamyl 5-phosphate + NADPH
N-Acetylornithine + Oxoglutaric acid > N-Acetyl-L-glutamate 5-semialdehyde + L-Glutamate
N-Acetyl-L-glutamate 5-semialdehyde + L-Glutamic acid + L-Glutamate > Oxoglutaric acid + N-Acetylornithine
N-Acetyl-L-glutamate 5-semialdehyde + NADP + Phosphate <> N-Acetyl-L-glutamyl 5-phosphate + Hydrogen ion + NADPH
N-Acetylornithine + alpha-Ketoglutarate <> N-Acetyl-L-glutamate 5-semialdehyde + L-Glutamate
SMPDB Pathways:
Lysine biosynthesisPW000771 ThumbThumb?image type=greyscaleThumb?image type=simple
arginine metabolismPW000790 ThumbThumb?image type=greyscaleThumb?image type=simple
ornithine metabolismPW000791 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-054o-9500000000-209b524fd8ef1d9e627fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006x-9420000000-8d264158e366f88d5d3eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fr-1900000000-cfaeff3cecd86134fd58View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-055r-6900000000-bb54f50a29e9a351858cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02a6-9100000000-fe9c1618b7f81c2f9d5bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-f6338ed4d753ef0b744eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0m89-3900000000-b5fbc1c314380afa8cc1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9100000000-a529029ad524b613c990View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0900000000-1f0440fa922d5815c5d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-5900000000-b295f71616c68600654dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-0d07a69d508963a4c246View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2900000000-d1bb675eb0f08dff7304View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01q9-3900000000-a872856bc77482a41b25View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-76a9b5ce42ea1d2112d2View in MoNA
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
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
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID16319
HMDB IDHMDB06488
Pubchem Compound ID192878
Kegg IDC01250
ChemSpider ID167387
Wikipedia IDNot Available
BioCyc IDCPD-469
EcoCyc IDCPD-469

Enzymes

Protein Details
1. N-acetyl-gamma-glutamyl-phosphate reductase
General function:
Involved in N-acetyl-gamma-glutamyl-phosphate reductase activity
Specific function:
N-acetyl-L-glutamate 5-semialdehyde + NADP(+) + phosphate = N-acetyl-5-glutamyl phosphate + NADPH
Gene Name:
argC
Uniprot ID:
P11446
Molecular weight:
35952
Reactions
N-acetyl-L-glutamate 5-semialdehyde + NADP(+) + phosphate = N-acetyl-5-glutamyl phosphate + NADPH.
Protein Details
2. Acetylornithine/succinyldiaminopimelate aminotransferase
General function:
Involved in transaminase activity
Specific function:
Involved in both the arginine and lysine biosynthetic pathways
Gene Name:
argD
Uniprot ID:
P18335
Molecular weight:
43767
Reactions
N(2)-acetyl-L-ornithine + 2-oxoglutarate = N-acetyl-L-glutamate 5-semialdehyde + L-glutamate.
N-succinyl-L-2,6-diaminoheptanedioate + 2-oxoglutarate = N-succinyl-2-L-amino-6-oxoheptanedioate + L-glutamate.
Protein Details
3. Acetylornithine deacetylase
General function:
Involved in zinc ion binding
Specific function:
Displays a broad specificity and can also deacylate substrates such as acetylarginine, acetylhistidine or acetylglutamate semialdehyde
Gene Name:
argE
Uniprot ID:
P23908
Molecular weight:
42347
Reactions
N(2)-acetyl-L-ornithine + H(2)O = acetate + L-ornithine.
Protein Details
4. Succinylornithine transaminase
General function:
Involved in transaminase activity
Specific function:
Catalyzes the transamination of N(2)-succinylornithine and alpha-ketoglutarate into N(2)-succinylglutamate semialdehyde and glutamate. Can also act as an acetylornithine aminotransferase
Gene Name:
astC
Uniprot ID:
P77581
Molecular weight:
43665
Reactions
N(2)-succinyl-L-ornithine + 2-oxoglutarate = N-succinyl-L-glutamate 5-semialdehyde + L-glutamate.