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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:04:33 UTC
HMDB IDHMDB01405
Secondary Accession NumbersNone
Metabolite Identification
Common Name3-Sulfinylpyruvic acid
DescriptionThis compound is found in the mammalian cysteine metobolic pathway. It is the deaminated form of Cysteine sulfinic acid (PMID: 3925121 ), which subsequently spontaneously reacts to form pyruvate while releasing sulfur dioxide. It is the byproduct of oxidoreductases (EC 1.4.1.-), and aspartate transaminase (EC 2.6.1.1). It is also often associated with hepatic disease, and the presence of aspartate transaminase is used in diagnostic biochemical assays of such ailments. (PMID: 17310554 ).
Structure
Thumb
Synonyms
ValueSource
3-SulfinopyruvateHMDB
3-Sulfinyl-pyruvateHMDB
3-SulfinylpyruvateHMDB
3-Sulphinyl-pyruvateHMDB
beta-SulfinylpyruvateHMDB
Chemical FormulaC3H3O5S
Average Molecular Weight151.118
Monoisotopic Molecular Weight150.970118896
IUPAC Name2-carboxy-2-oxoethane-1-sulfinate
Traditional Name2-carboxy-2-oxoethanesulfinate
CAS Registry NumberNot Available
SMILES
OC(=O)C(=O)CS([O-])=O
InChI Identifier
InChI=1S/C3H4O5S/c4-2(3(5)6)1-9(7)8/h1H2,(H,5,6)(H,7,8)/p-1
InChI KeyInChIKey=JXYLQEMXCAAMOL-UHFFFAOYSA-M
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alpha-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassAlpha-keto acids and derivatives
Direct ParentAlpha-keto acids and derivatives
Alternative Parents
Substituents
  • Alpha-keto acid
  • Alpha-hydroxy ketone
  • Alkanesulfinic acid
  • Alkanesulfinic acid or derivatives
  • Sulfinic acid derivative
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Carbonyl group
  • Organic anion
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility19.5 mg/mLALOGPS
logP-0.46ALOGPS
logP-0.34ChemAxon
logS-0.94ALOGPS
pKa (Strongest Acidic)-1ChemAxon
pKa (Strongest Basic)-9.9ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area94.5 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity25.77 m3·mol-1ChemAxon
Polarizability11.35 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-3f36febe04999bc99129View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-3900000000-db39126e856a94a9f5baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0230-9100000000-6530a70aaf1ffd96d527View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-2900000000-5dc0d79c5085e66b6be2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-8900000000-51c27247dd3089973bc6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-9200000000-037900bbf3c791ecef65View in MoNA
Biological Properties
Cellular Locations
  • Mitochondria
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Beta-mercaptolactate-cysteine disulfiduriaSMP00499Not Available
Cysteine MetabolismSMP00013map00270
Cystinosis, ocular nonnephropathicSMP00722Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022603
KNApSAcK IDNot Available
Chemspider ID4911362
KEGG Compound IDC05527
BioCyc ID3-SULFINYL-PYRUVATE
BiGG ID45969
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01405
Metagene LinkHMDB01405
METLIN ID6222
PubChem Compound6398963
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Kunert J: Metabolism of sulfur-containing amino acids in the dermatophyte Microsporum gypseum. II. Acidic amino acid derivatives. J Basic Microbiol. 1985;25(2):111-8. [3925121 ]
  2. Oparinde DP, Oghagbon EK, Okesina AB, Olatunji PO, Ojuawo AO: Role of hepatic enzymes in the biochemical assessment of the severity of sickle cell anemia. Trop Gastroenterol. 2006 Jul-Sep;27(3):118-21. [17310554 ]

Enzymes

General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Plays a key role in amino acid metabolism (By similarity).
Gene Name:
GOT1
Uniprot ID:
P17174
Molecular weight:
46247.14
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Plays a key role in amino acid metabolism. Important for metabolite exchange between mitochondria and cytosol. Facilitates cellular uptake of long-chain free fatty acids.
Gene Name:
GOT2
Uniprot ID:
P00505
Molecular weight:
47517.285