Oxalosuccinic acid (YMDB00210)

Identification
YMDB IDYMDB00210
NameOxalosuccinic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionOxalosuccinic acid, also known as oxalosuccinate or oxalbernsteinsaeure, belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. Oxalosuccinic acid exists in all living species, ranging from bacteria to plants to humans. Based on a literature review very few articles have been published on Oxalosuccinic acid.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • Oxalosuccinate
  • Oxalosuccinic acid
  • 1-Oxopropane-1,2,3-tricarboxylate
  • Oxalbernsteinsaeure
  • 1-Oxopropane-1,2,3-tricarboxylic acid
CAS number1948-82-9
WeightAverage: 190.1076
Monoisotopic: 190.011352546
InChI KeyUFSCUAXLTRFIDC-UHFFFAOYSA-N
InChIInChI=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)
IUPAC Name1-oxopropane-1,2,3-tricarboxylic acid
Traditional IUPAC Nameoxalosuccinate
Chemical FormulaC6H6O7
SMILES[H]OC(=O)C(=O)C([H])(C(=O)O[H])C([H])([H])C(=O)O[H]
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
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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
  • Mitochondrion
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG Pathways
Citrate cycle (TCA cycle)ec00020 Map00020
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0005-6900000000-05e6953cf97abc6dd674JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00rf-9137000000-9567484c80debff89c0eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dj-1900000000-ed9f625da4af156fd85aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006t-8900000000-b245ec6d4dca3949083dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006t-9300000000-00b8a65afa1e83c61b5aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000b-0900000000-a6734cca6590d164a554JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-3900000000-c30d22d22f12460fcc5cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dj-9300000000-a3b40df9f3852aa0e3c8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fi0-0900000000-de098f1139c0f6fbd19dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0092-9800000000-03bc5902024a449a2d18JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9000000000-ef352a8e83bf22a4b124JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6t-3900000000-654a5517d3a1a65425e3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f6t-7900000000-7b0190686602c20ebac6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fk9-9500000000-e5f05497c77c1ef44cf0JSpectraViewer
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
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Synthesis Reference:Takeda, Isao; Iguchi, Takashi. Fermentative production of oxalosuccinic acid from hydrocarbons. Jpn. Tokkyo Koho (1972), 3 pp.
External Links:
ResourceLink
CHEBI ID7815
HMDB IDHMDB03974
Pubchem Compound ID972
Kegg IDC05379
ChemSpider ID947
FOODB IDFDB031076
WikipediaOxalosuccinic_acid
BioCyc IDOXALO-SUCCINATE

Enzymes

Protein Details
1. Isocitrate dehydrogenase [NADP]
General function:
Involved in magnesium ion binding
Specific function:
May function in the production of NADPH for fatty acid and sterol synthesis
Gene Name:
IDP3
Uniprot ID:
P53982
Molecular weight:
47856.0
Reactions
Isocitrate + NADP(+) → 2-oxoglutarate + CO(2) + NADPH.
Oxalosuccinate + NADP(+) → 2-oxoglutarate + CO(2) + NADPH.
Protein Details
2. Isocitrate dehydrogenase [NADP], mitochondrial
General function:
Involved in magnesium ion binding
Specific function:
Mitochondrial IDP1 may regulate flux through the tricarboxylic acid cycle and respiration. Its probably critical function is the production of NADPH
Gene Name:
IDP1
Uniprot ID:
P21954
Molecular weight:
48189.89844
Reactions
Isocitrate + NADP(+) → 2-oxoglutarate + CO(2) + NADPH.
Oxalosuccinate + NADP(+) → 2-oxoglutarate + CO(2) + NADPH.
Protein Details
3. Isocitrate dehydrogenase [NADP] cytoplasmic
General function:
Involved in magnesium ion binding
Specific function:
May function in the production of NADPH for fatty acid and sterol synthesis
Gene Name:
IDP2
Uniprot ID:
P41939
Molecular weight:
46561.89844
Reactions
Isocitrate + NADP(+) → 2-oxoglutarate + CO(2) + NADPH.
Oxalosuccinate + NADP(+) → 2-oxoglutarate + CO(2) + NADPH.