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N-Acetylornithine (YMDB00028)

Identification
YMDB IDYMDB00028
NameN-Acetylornithine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionN2-Acetylornithine 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. N2-Acetylornithine exists in all living species, ranging from bacteria to plants to humans. Based on a literature review a significant number of articles have been published on N2-Acetylornithine.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (2S)-2-acetamido-5-aminopentanoate
  • (2S)-2-acetamido-5-aminopentanoic acid
  • Acetyl-ornithine
  • AOR
  • delta-N-Acetylornithine
  • N(2)-acetyl-L-ornithine
  • N(delta)-Acetylornithine
  • N(delta)-Acetylornithine, (DL)-isomer
  • N2-Acetyl-L-ornithine
  • N-Acetylornithine
  • (2S)-5-Amino-2-acetamidopentanoic acid
  • N(alpha)-Acetyl-L-ornithine
  • N(alpha)-Acetylornithine
  • N(α)-Acetyl-L-ornithine
  • N(α)-Acetylornithine
  • N-Acetyl-L-ornithine
  • Nalpha-Acetyl-L-ornithine
  • Nalpha-Acetylornithine
  • Nα-Acetyl-L-ornithine
  • Nα-Acetylornithine
  • N2-Acetylornithine
  • N-alpha-Acetylornithine
  • N-α-Acetylornithine
CAS number6205-08-9
WeightAverage: 174.1977
Monoisotopic: 174.100442324
InChI KeyJRLGPAXAGHMNOL-LURJTMIESA-N
InChIInChI=1S/C7H14N2O3/c1-5(10)9-6(7(11)12)3-2-4-8/h6H,2-4,8H2,1H3,(H,9,10)(H,11,12)/t6-/m0/s1
IUPAC Name(2S)-5-amino-2-acetamidopentanoic acid
Traditional IUPAC NameN(2)-acetyl-L-ornithine
Chemical FormulaC7H14N2O3
SMILES[H]OC(=O)[C@@]([H])(N([H])C(=O)C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])N([H])[H]
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
  • Acetamide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Amino acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogP-0.896PhysProp
Predicted Properties
PropertyValueSource
Water Solubility37.8 g/LALOGPS
logP-2.7ALOGPS
logP-3.6ChemAxon
logS-0.66ALOGPS
pKa (Strongest Acidic)3.82ChemAxon
pKa (Strongest Basic)9.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area92.42 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity42.65 m³·mol⁻¹ChemAxon
Polarizability17.94 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
L-Glutamic acid + N-Acetylornithine → N-acetyl-L-glutamic acid + Ornithine
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0fk9-1930000000-28d5f476677a51e2f8ecJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-00di-2900000000-092b404eaa0526439b15JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fk9-0930000000-6914c12040164b5148b0JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-0910000000-25d42f7fce94b1cb4b5cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fk9-1920000000-e1b66d25c11eafd0e0a9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-1900000000-0f0883367079e716da18JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0fk9-1930000000-28d5f476677a51e2f8ecJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-2900000000-092b404eaa0526439b15JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001l-9100000000-429f70cb44411bb90989JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fkc-9410000000-cee666cdbec55f97a0a0JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0900000000-52f0d0fb8a9a849e95d6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0900000000-d83ff24b1fd0244f8e2eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-2900000000-e708e107e9183bfe0f76JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-053r-9400000000-afb6a5b65f59f01dc761JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4l-9000000000-4763dc8edae338a7f336JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0900000000-d157410f17955c8e0256JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-0900000000-52b9626c047fdc01fe7bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-1900000000-c92081162e58f54cd2ecJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-9200000000-476b94e0eacd5c51da0dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-9000000000-e57c224e36a05f66f1b9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-9000000000-44d1c5e14f69e175989aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-03fr-0900000000-5fe61be67a41d8d0faccJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-01b9-4900000000-624c1afbfd5d3b3b76cbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-01b9-4900000000-624c1afbfd5d3b3b76cbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-310a7f3b3d4c1bf3af0bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-00di-9000000000-d0f88533afec85ff5c62JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-05r0-0900000000-f280065b578a1aa65149JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-01b9-8900000000-cf2ff97fd954fbc2ad67JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a59-9000000000-ff059f4dd36bc1002fbfJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-1900000000-28d5e48c6fc3a56a4937JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06tr-4900000000-8aa79d29a3d89249bf78JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01vx-9200000000-2f866830ef23136853fcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-9b37a30ee623b4f18e80JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0c30-4900000000-019d18f26e04ab2b397aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9100000000-b133fb2ce9e1a5eef782JSpectraViewer
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
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • 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
  • Liu, Y., Van Heeswijck, R., Hoj, P., Hoogenraad, N. (1995). "Purification and characterization of ornithine acetyltransferase from Saccharomyces cerevisiae." Eur J Biochem 228:291-296.7705341
  • Crabeel, M., Abadjieva, A., Hilven, P., Desimpelaere, J., Soetens, O. (1997). "Characterization of the Saccharomyces cerevisiae ARG7 gene encoding ornithine acetyltransferase, an enzyme also endowed with acetylglutamate synthase activity." Eur J Biochem 250:232-241.9428669
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID16543
HMDB IDHMDB03357
Pubchem Compound ID439232
Kegg IDC00437
ChemSpider ID388369
FOODB IDFDB023152
Wikipedia IDNot Available
BioCyc IDN-ALPHA-ACETYLORNITHINE

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. Arginine biosynthesis bifunctional protein ArgJ, mitochondrial
General function:
Involved in glutamate N-acetyltransferase activity
Specific function:
Catalyzes two activities which are involved in the cyclic version of arginine biosynthesis:the synthesis of acetylglutamate from glutamate and acetyl-CoA, and of ornithine by transacetylation between acetylornithine and glutamate
Gene Name:
ARG7
Uniprot ID:
Q04728
Molecular weight:
47848.30078
Reactions
N(2)-acetyl-L-ornithine + L-glutamate → L-ornithine + N-acetyl-L-glutamate.
Acetyl-CoA + L-glutamate → CoA + N-acetyl-L-glutamate.