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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
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 acidOxoglutaric acid + N-Acetylornithine
N-Acetyl-L-glutamyl 5-phosphate + NADPH + hydronNADP + phosphate + 2-Acetamido-5-oxopentanoic acid
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
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

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.
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.