Record Information
Version2.0
Creation Date2012-05-31 13:45:58 -0600
Update Date2015-06-03 15:53:46 -0600
Secondary Accession Numbers
  • ECMDB01131
Identification
Name:Iminoaspartic acid
DescriptionIminoaspartic acid (alpha-iminosuccinate) is an intermediate in NAD biosynthesis from aspartate pathwyay. As a general rule, most prokaryotes utilize the aspartate de novo pathway, in which the nicotinate moiety of NAD is synthesized from aspartate, while in eukaryotes, the de novo pathway starts with tryptophan.
Structure
Thumb
Synonyms:
  • a-Iminosuccinate
  • a-Iminosuccinic acid
  • Alpha-Iminosuccinate
  • Alpha-Iminosuccinic acid
  • Imino-Butanedioate
  • Imino-Butanedioic acid
  • Iminoaspartate
  • Iminoaspartic acid
  • Iminosuccinate
  • Iminosuccinic acid
  • α-Iminosuccinate
  • α-Iminosuccinic acid
Chemical Formula:C4H5NO4
Weight:Average: 131.0868
Monoisotopic: 131.021857653
InChI Key:NMUOATVLLQEYHI-UHFFFAOYSA-N
InChI:InChI=1S/C4H5NO4/c5-2(4(8)9)1-3(6)7/h5H,1H2,(H,6,7)(H,8,9)
CAS number:79067-61-1
IUPAC Name:2-iminobutanedioic acid
Traditional IUPAC Name:iminosuccinic acid
SMILES:OC(=O)CC(=N)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassDicarboxylic acids and derivatives
Direct ParentDicarboxylic acids and derivatives
Alternative Parents
Substituents
  • Fatty acid
  • Dicarboxylic acid or derivatives
  • Ketimine
  • Carboxylic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility4.26 g/LALOGPS
logP-0.83ALOGPS
logP-0.51ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)3.28ChemAxon
pKa (Strongest Basic)2.48ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area98.45 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity36.81 m³·mol⁻¹ChemAxon
Polarizability10.55 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Dihydroxyacetone phosphate + Iminoaspartic acid <>2 Water + Phosphate + Quinolinic acid
L-Aspartic acid + Fumaric acid > Hydrogen ion + Iminoaspartic acid + Succinic acid
L-Aspartic acid + Oxygen <> Hydrogen ion + Hydrogen peroxide + Iminoaspartic acid
L-Aspartic acid + Ubiquinone-8 > Hydrogen ion + Iminoaspartic acid + Ubiquinol-8
L-Aspartic acid + Menaquinone 8 > Hydrogen ion + Iminoaspartic acid + Menaquinol 8
L-Aspartic acid + Oxygen <> Iminoaspartic acid + Hydrogen peroxide
Quinolinic acid + 2 Water + Phosphate <> Iminoaspartic acid + Dihydroxyacetone phosphate
Oxygen + L-Aspartic acid > Hydrogen ion + Hydrogen peroxide + Iminoaspartic acid
Iminoaspartic acid + Dihydroxyacetone phosphate > Quinolinic acid + Water + Phosphate
Dihydroxyacetone phosphate + Iminoaspartic acid > Quinolinic acid +2 Water + Inorganic phosphate
L-Aspartic acid + Oxygen > Iminoaspartic acid + Hydrogen peroxide
L-Aspartic acid + Oxygen + L-Aspartic acid > Hydrogen peroxide + Hydrogen ion + Iminoaspartic acid
Iminoaspartic acid + Dihydroxyacetone phosphate > Phosphate +2 Water + Quinolinic acid
L-Aspartic acid + Oxygen <> Hydrogen ion + Hydrogen peroxide + Iminoaspartic acid
Dihydroxyacetone phosphate + Iminoaspartic acid <>2 Water + Phosphate + Quinolinic acid
Quinolinic acid + 2 Water + Phosphate <> Iminoaspartic acid + Dihydroxyacetone phosphate
L-Aspartic acid + Oxygen <> Hydrogen ion + Hydrogen peroxide + Iminoaspartic acid
Dihydroxyacetone phosphate + Iminoaspartic acid <>2 Water + Phosphate + Quinolinic acid
SMPDB Pathways:
NAD biosynthesisPW000829 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Alanine, aspartate and glutamate metabolism ec00250
  • Metabolic pathways eco01100
  • Nicotinate and nicotinamide metabolism ec00760
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000l-9100000000-bf5c48c685bd4d8bc19cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00dl-9330000000-0a7a3a014d87506d9d5cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03y0-7900000000-1e7dec8cec535849b8ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00y0-9000000000-ee01d5b059cd84acc52aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9000000000-f7639f26eeb1737eca80View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001r-4900000000-48f2522721d80612277bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01q0-9600000000-13c57e1870999d070c90View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066u-9000000000-142f158a200b457f476fView in MoNA
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
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID50616
HMDB IDHMDB01131
Pubchem Compound ID796
Kegg IDC05840
ChemSpider ID13628208
Wikipedia IDIminosuccinic acid
BioCyc IDIMINOASPARTATE
EcoCyc IDIMINOASPARTATE

Enzymes

General function:
Involved in electron carrier activity
Specific function:
Catalyzes the oxidation of L-aspartate to iminoaspartate
Gene Name:
nadB
Uniprot ID:
P10902
Molecular weight:
60337
Reactions
L-aspartate + O(2) = iminosuccinate + H(2)O(2).
General function:
Involved in quinolinate synthetase A activity
Specific function:
Catalyzes the condensation of iminoaspartate with dihydroxyacetone phosphate to form quinolinate
Gene Name:
nadA
Uniprot ID:
P11458
Molecular weight:
38240
Reactions
Glycerone phosphate + iminosuccinate = pyridine-2,3-dicarboxylate + 2 H(2)O + phosphate.