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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-13 08:19:32 UTC
Update Date2021-09-14 15:46:13 UTC
HMDB IDHMDB0003974
Secondary Accession Numbers
  • HMDB03974
Metabolite Identification
Common NameOxalosuccinic acid
Description(S)-oxalosuccinic acid, also known as 2-oxalosuccinate, belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups (S)-oxalosuccinic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1600136726
Synonyms
ValueSource
2-OXALOSUCCINIC ACIDChEBI
2-OXALOSUCCINateGenerator
(S)-OxalosuccinateGenerator
1-Oxo-1,2,3-propanetricarboxylic acidHMDB
OxalosuccinateHMDB
Oxalosuccinic acidHMDB
Chemical FormulaC6H6O7
Average Molecular Weight190.1076
Monoisotopic Molecular Weight190.011352546
IUPAC Name(2S)-1-oxopropane-1,2,3-tricarboxylic acid
Traditional Name(S)-oxalosuccinic acid
CAS Registry Number1948-82-9
SMILES
OC(=O)C[C@H](C(O)=O)C(=O)C(O)=O
InChI Identifier
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)/t2-/m0/s1
InChI KeyUFSCUAXLTRFIDC-REOHCLBHSA-N
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
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular 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
Polarizability14.94 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
Oxalosuccinic acid,1TMS,#11615.9429https://arxiv.org/abs/1905.12712
Oxalosuccinic acid,1TMS,#21582.0457https://arxiv.org/abs/1905.12712
Oxalosuccinic acid,1TMS,#31586.9865https://arxiv.org/abs/1905.12712
Oxalosuccinic acid,1TMS,#41698.9327https://arxiv.org/abs/1905.12712
Oxalosuccinic acid,2TMS,#11701.2528https://arxiv.org/abs/1905.12712
Oxalosuccinic acid,2TMS,#21670.4838https://arxiv.org/abs/1905.12712
Oxalosuccinic acid,2TMS,#31791.7886https://arxiv.org/abs/1905.12712
Oxalosuccinic acid,2TMS,#41656.9149https://arxiv.org/abs/1905.12712
Oxalosuccinic acid,2TMS,#51735.8955https://arxiv.org/abs/1905.12712
Oxalosuccinic acid,2TMS,#61738.0403https://arxiv.org/abs/1905.12712
Oxalosuccinic acid,3TMS,#11793.5787https://arxiv.org/abs/1905.12712
Oxalosuccinic acid,3TMS,#21833.9193https://arxiv.org/abs/1905.12712
Oxalosuccinic acid,3TMS,#31816.1895https://arxiv.org/abs/1905.12712
Oxalosuccinic acid,3TMS,#41804.7124https://arxiv.org/abs/1905.12712
Oxalosuccinic acid,1TBDMS,#11887.2771https://arxiv.org/abs/1905.12712
Oxalosuccinic acid,1TBDMS,#21844.8893https://arxiv.org/abs/1905.12712
Oxalosuccinic acid,1TBDMS,#31853.7958https://arxiv.org/abs/1905.12712
Oxalosuccinic acid,1TBDMS,#41966.2915https://arxiv.org/abs/1905.12712
Oxalosuccinic acid,2TBDMS,#12182.0571https://arxiv.org/abs/1905.12712
Oxalosuccinic acid,2TBDMS,#22141.0344https://arxiv.org/abs/1905.12712
Oxalosuccinic acid,2TBDMS,#32265.2217https://arxiv.org/abs/1905.12712
Oxalosuccinic acid,2TBDMS,#42126.7783https://arxiv.org/abs/1905.12712
Oxalosuccinic acid,2TBDMS,#52198.3926https://arxiv.org/abs/1905.12712
Oxalosuccinic acid,2TBDMS,#62209.9382https://arxiv.org/abs/1905.12712
Oxalosuccinic acid,3TBDMS,#12440.526https://arxiv.org/abs/1905.12712
Oxalosuccinic acid,3TBDMS,#22473.3225https://arxiv.org/abs/1905.12712
Oxalosuccinic acid,3TBDMS,#32477.869https://arxiv.org/abs/1905.12712
Oxalosuccinic acid,3TBDMS,#42443.7512https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0005-6900000000-05e6953cf97abc6dd6742017-08-28View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0095-0900000000-7e59d1df8b3c23391b742017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0092-6900000000-5f5d2cd185d08e13c9502017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006t-9400000000-8f63cf7f954d853724e42017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000b-0900000000-ae22625fc1627bd711be2017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-4900000000-a80b78caa72c122aab742017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dj-9200000000-21b5b2295a5061ba60b32017-07-26View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02190
Phenol Explorer Compound IDNot Available
FooDB IDFDB031076
KNApSAcK IDNot Available
Chemspider ID4593408
KEGG Compound IDC05379
BioCyc IDOXALO-SUCCINATE
BiGG IDNot Available
Wikipedia LinkOxalosuccinic_acid
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID44712
Food Biomarker OntologyNot Available
VMH IDHC01434
MarkerDB IDNot Available
References
Synthesis ReferenceTakeda, Isao; Iguchi, Takashi. Fermentative production of oxalosuccinic acid from hydrocarbons. Jpn. Tokkyo Koho (1972), 3 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. HUELSMANN WC: SYNTHESIS OF MALONYL-COENZYME A FROM ACETYL-COENZYME A AND OXALOSUCCINATE IN MITOCHONDRIA. Biochim Biophys Acta. 1963 Nov 8;77:502-3. [PubMed:14089428 ]
  2. OCHOA S: Biosynthesis of tricarboxylic acids by carbon dioxide fixation; the preparation and properties of oxalosuccinic acid. J Biol Chem. 1948 May;174(1):115-22. [PubMed:18914069 ]

Enzymes

General function:
Involved in magnesium ion binding
Specific function:
Plays a role in intermediary metabolism and energy production. It may tightly associate or interact with the pyruvate dehydrogenase complex.
Gene Name:
IDH2
Uniprot ID:
P48735
Molecular weight:
50908.915
Reactions
Oxalosuccinic acid → Oxoglutaric acid + Carbon dioxidedetails
Isocitric acid + NADP → Oxalosuccinic acid + NADPH + Hydrogen Iondetails
General function:
Involved in magnesium ion binding
Specific function:
Not Available
Gene Name:
IDH1
Uniprot ID:
O75874
Molecular weight:
46659.005
Reactions
Oxalosuccinic acid → Oxoglutaric acid + Carbon dioxidedetails
Isocitric acid + NADP → Oxalosuccinic acid + NADPH + Hydrogen Iondetails