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Oxalosuccinic acid (M2MDB000548)

Record Information
Version2.0
Creation Date2012-05-31 14:01:37 -0600
Update Date2015-07-14 14:32:03 -0600
Secondary Accession Numbers
  • ECMDB03974
Identification
Name:Oxalosuccinic acid
DescriptionOxalosuccinate is a substrate for cytoplasmic Isocitrate dehydrogenase and mitochondiral Isocitrate dehydrogenase (mitochondrial).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • Oxalo-succ
  • Oxalosuccinate
  • Oxalosuccinic acid
Chemical Formula:C6H6O7
Weight:Average: 190.1076
Monoisotopic: 190.011352546
InChI Key:UFSCUAXLTRFIDC-UHFFFAOYSA-N
InChI:InChI=1S/C6H6O7/c7-3(8)1-2(5(10)11)4(9)6(12)13/h2H,1H2,(H,7,8)(H,10,11)(H,12,13)
CAS number:1948-82-9
IUPAC Name:1-oxopropane-1,2,3-tricarboxylic acid
Traditional IUPAC Name:oxalosuccinate
SMILES:OC(=O)CC(C(O)=O)C(=O)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassTricarboxylic acids and derivatives
Direct ParentTricarboxylic acids and derivatives
Alternative Parents
Substituents
  • Tricarboxylic acid or derivatives
  • Gamma-keto acid
  • Beta-keto acid
  • Alpha-keto acid
  • Beta-hydroxy ketone
  • Keto acid
  • 1,3-dicarbonyl compound
  • Alpha-hydroxy ketone
  • Ketone
  • Carboxylic acid
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility7.47 g/LALOGPS
logP-0.55ALOGPS
logP-0.37ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)2.38ChemAxon
pKa (Strongest Basic)-10ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area128.97 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity35.17 m³·mol⁻¹ChemAxon
Polarizability14.95 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Oxalosuccinic acid <> alpha-Ketoglutarate + Carbon dioxide
Isocitric acid + NADP <> Oxalosuccinic acid + NADPH + Hydrogen ion
Oxalosuccinic acid + Hydrogen ion > Oxoglutaric acid + Carbon dioxide
Isocitric acid + NADP > Oxalosuccinic acid + NADPH + Hydrogen ion
Isocitric acid + NADP + Oxalosuccinic acid <> alpha-Ketoglutarate + Carbon dioxide + NADPH + Hydrogen ion
SMPDB Pathways:
Glutathione metabolismPW000833 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0005-6900000000-05e6953cf97abc6dd674View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00rf-9137000000-9567484c80debff89c0eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dj-1900000000-ed9f625da4af156fd85aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006t-8900000000-b245ec6d4dca3949083dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006t-9300000000-00b8a65afa1e83c61b5aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000b-0900000000-a6734cca6590d164a554View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-3900000000-c30d22d22f12460fcc5cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dj-9300000000-a3b40df9f3852aa0e3c8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fi0-0900000000-de098f1139c0f6fbd19dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0092-9800000000-03bc5902024a449a2d18View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9000000000-ef352a8e83bf22a4b124View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6t-3900000000-654a5517d3a1a65425e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f6t-7900000000-7b0190686602c20ebac6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fk9-9500000000-e5f05497c77c1ef44cf0View in MoNA
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
1D NMR1H 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
Synthesis Reference:Takeda, Isao; Iguchi, Takashi. Fermentative production of oxalosuccinic acid from hydrocarbons. Jpn. Tokkyo Koho (1972), 3 pp.
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID7815
HMDB IDHMDB03974
Pubchem Compound ID972
Kegg IDC05379
ChemSpider ID947
WikipediaOxalosuccinic_acid
BioCyc IDOXALO-SUCCINATE
EcoCyc IDOXALO-SUCCINATE

Enzymes

Protein Details
1. Isocitrate dehydrogenase [NADP]
General function:
Involved in magnesium ion binding
Specific function:
Isocitrate + NADP(+) = 2-oxoglutarate + CO(2) + NADPH
Gene Name:
icd
Uniprot ID:
P08200
Molecular weight:
45756
Reactions
Isocitrate + NADP(+) = 2-oxoglutarate + CO(2) + NADPH.