2-Acetamido-5-oxopentanoic acid (YMDB00536)

Identification
YMDB IDYMDB00536
Name2-Acetamido-5-oxopentanoic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description2-Acetamido-5-oxopentanoic acid is an intermediate in urea cycle and metabolism of amino groups. N-Acetyl-L-glutamate 5-semialdehyde is the second to last step in the synthesis of L-ornithine and is converted from N-acetyl-L-glutamate 5-phosphate via the enzyme N-acetyl-gamma-glutamyl-phosphate reductase [EC: 1.2.1.38]. It is then converted to N-acetylornithine via the enzyme acetylornithine aminotransferase [EC: 2.6.1.11].
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 2-acetamido-5-oxopentanoate
  • 2-acetamido-5-oxovalerate
  • N-Acetyl-L-glutamate 5-semialdehyde
  • 2-Acetamido-5-oxovaleric acid
  • N-Acetyl-5-oxo-L-norvaline
  • 2-Acetamido-5-oxopentanoic acid
  • N-Acetyl-L-glutamic acid 5-semialdehyde
  • N-Acetyl-L-glutamic acid gamma-semialdehyde
CAS numberNot Available
WeightAverage: 173.1665
Monoisotopic: 173.068807845
InChI KeyBCPSFKBPHHBDAI-LURJTMIESA-N
InChIInChI=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
IUPAC Name(2S)-2-acetamido-5-oxopentanoic acid
Traditional IUPAC NameN-acetyl-5-oxo-L-norvaline
Chemical FormulaC7H11NO4
SMILESCC(=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
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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
  • mitochondrion
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG Pathways
Arginine and proline metabolismec00330 Map00330
SMPDB ReactionsNot Available
KEGG Reactions
2-Acetamido-5-oxopentanoic acid + L-Glutamic acid → Oxoglutaric acid + N-Acetylornithine
N-Acetyl-L-glutamyl 5-phosphate + NADPH + hydron → NADP + phosphate + 2-Acetamido-5-oxopentanoic acid
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-054o-9500000000-209b524fd8ef1d9e627fJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006x-9420000000-8d264158e366f88d5d3eJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fr-1900000000-cfaeff3cecd86134fd58JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-055r-6900000000-bb54f50a29e9a351858cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02a6-9100000000-fe9c1618b7f81c2f9d5bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-f6338ed4d753ef0b744eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0m89-3900000000-b5fbc1c314380afa8cc1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9100000000-a529029ad524b613c990JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0900000000-1f0440fa922d5815c5d9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-5900000000-b295f71616c68600654dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-0d07a69d508963a4c246JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2900000000-d1bb675eb0f08dff7304JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01q9-3900000000-a872856bc77482a41b25JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-76a9b5ce42ea1d2112d2JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID29123
HMDB IDHMDB0006488
Pubchem Compound ID905
Kegg IDC01250
ChemSpider ID167387
FOODB IDFDB023938
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Acetylornithine aminotransferase, mitochondrial
General function:
Involved in transaminase activity
Specific function:
N(2)-acetyl-L-ornithine + 2-oxoglutarate = N- acetyl-L-glutamate 5-semialdehyde + L-glutamate
Gene Name:
ARG8
Uniprot ID:
P18544
Molecular weight:
46681.10156
Reactions
N(2)-acetyl-L-ornithine + 2-oxoglutarate → N-acetyl-L-glutamate 5-semialdehyde + L-glutamate.
Protein Details
2. Protein ARG5,6, mitochondrial
General function:
Involved in acetylglutamate kinase activity
Specific function:
N-acetyl-L-glutamate 5-semialdehyde + NADP(+) + phosphate = N-acetyl-5-glutamyl phosphate + NADPH
Gene Name:
ARG5
Uniprot ID:
Q01217
Molecular weight:
94868.39844
Reactions
N-acetyl-L-glutamate 5-semialdehyde + NADP(+) + phosphate → N-acetyl-5-glutamyl phosphate + NADPH.
ATP + N-acetyl-L-glutamate → ADP + N-acetyl-L-glutamate 5-phosphate.