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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2018-05-17 15:52:16 UTC
HMDB IDHMDB0001405
Secondary Accession Numbers
  • HMDB01405
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-SulfinopyruvateChEBI
3-SulfinylpyruvateChEBI
3-Sulfinopyruvic acidGenerator
3-SulphinopyruvateGenerator
3-Sulphinopyruvic acidGenerator
b-Sulfinyl pyruvic acidGenerator
b-Sulphinyl pyruvateGenerator
b-Sulphinyl pyruvic acidGenerator
3-Sulfinylpyruvic acidGenerator
3-SulphinylpyruvateGenerator
3-Sulphinylpyruvic acidGenerator
beta-Sulfinyl pyruvateHMDB
beta-Sulfinyl pyruvic acidHMDB
beta-Sulfinyl- pyruvateHMDB
Chemical FormulaC3H4O5S
Average Molecular Weight152.126
Monoisotopic Molecular Weight151.977943928
IUPAC Name2-oxo-3-sulfinopropanoic acid
Traditional Name3-sulfinylpyruvate
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)
InChI KeyJXYLQEMXCAAMOL-UHFFFAOYSA-N
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
  • Sulfinic acid
  • Ketone
  • Alkanesulfinic acid
  • Alkanesulfinic acid or derivatives
  • Sulfinic acid derivative
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Organosulfur compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

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 g/LALOGPS
logP-0.2ALOGPS
logP-0.34ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)1.71ChemAxon
pKa (Strongest Basic)-9.9ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.67 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity26.89 m³·mol⁻¹ChemAxon
Polarizability11.63 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0bvl-9300000000-b9d5aeadd8b7738b7353View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0ab9-9600000000-56bba3bcd18999fead91View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0900000000-871c9b0796f2447470edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00li-9600000000-da362e24b25de10e7c3eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-47872b5d21e6463c1ffcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1900000000-d91ad6a6d2809d9a6714View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fb9-9400000000-f213ed656a1bcd5e1554View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0w93-9400000000-7973a19a971bd544bf7eView in MoNA
Biological Properties
Cellular Locations
  • Mitochondria
Biospecimen LocationsNot Available
Tissue LocationNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022965
KNApSAcK IDNot Available
Chemspider ID108
KEGG Compound IDC05527
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6627
PubChem Compound110
PDB IDNot Available
ChEBI ID1665
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. [PubMed: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. [PubMed: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