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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:23:19 UTC
HMDB IDHMDB0001405
Secondary Accession Numbers
  • HMDB0002332
  • HMDB01405
  • HMDB02332
Metabolite Identification
Common Name3-Sulfinylpyruvic acid
Description3-Sulfinylpyruvic acid is a compound found in the mammalian cysteine metabolic pathway. It is the deaminated form of cysteine sulfinic acid which subsequently spontaneously reacts to form pyruvate and release sulfur dioxide (PMID: 3925121 , 6822523 ). 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
Data?1582752198
Synonyms
ValueSource
3-SulfinopyruvateChEBI
3-SulfinylpyruvateChEBI
3-Sulfinopyruvic acidGenerator
3-SulphinopyruvateGenerator
3-Sulphinopyruvic acidGenerator
3-SulphinylpyruvateGenerator
3-Sulphinylpyruvic acidGenerator
beta-Sulfinyl pyruvateHMDB
beta-Sulfinyl pyruvic acidHMDB
2-oxo-3-Sulfinopropanoic acidHMDB
beta-Sulfinyl-pyruvateHMDB
beta-Sulfinyl-pyruvic acidHMDB
Β-sulfinyl pyruvateHMDB
Β-sulfinyl pyruvic acidHMDB
Β-sulfinyl-pyruvateHMDB
Β-sulfinyl-pyruvic acidHMDB
3-Sulfinylpyruvic acidGenerator
Chemical FormulaC3H4O5S
Average Molecular Weight152.126
Monoisotopic Molecular Weight151.977943928
IUPAC Name2-oxo-3-sulfinopropanoic acid
Traditional Name3-sulfinylpyruvate
CAS Registry Number88947-38-0
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
Description 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
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+132.02831661259
DarkChem[M+H]+132.02831661259
DarkChem[M+H]+132.02831661259
DarkChem[M+H]+132.02831661259
DarkChem[M-H]-124.44531661259
DarkChem[M-H]-124.44531661259
DarkChem[M-H]-124.44531661259
DarkChem[M-H]-124.44531661259
AllCCS[M+H]+132.66132859911
AllCCS[M-H]-124.89732859911
DeepCCS[M+H]+124.83530932474
DeepCCS[M-H]-121.29130932474
DeepCCS[M-2H]-158.21730932474
DeepCCS[M+Na]+133.42530932474
AllCCS[M+H]+132.732859911
AllCCS[M+H-H2O]+128.732859911
AllCCS[M+NH4]+136.432859911
AllCCS[M+Na]+137.532859911
AllCCS[M-H]-124.932859911
AllCCS[M+Na-2H]-127.532859911
AllCCS[M+HCOO]-130.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Sulfinylpyruvic acidOC(=O)C(=O)CS(O)=O2669.3Standard polar33892256
3-Sulfinylpyruvic acidOC(=O)C(=O)CS(O)=O1019.8Standard non polar33892256
3-Sulfinylpyruvic acidOC(=O)C(=O)CS(O)=O1343.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Sulfinylpyruvic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)C(=O)CS(=O)O1438.4Semi standard non polar33892256
3-Sulfinylpyruvic acid,1TMS,isomer #2C[Si](C)(C)OS(=O)CC(=O)C(=O)O1466.7Semi standard non polar33892256
3-Sulfinylpyruvic acid,1TMS,isomer #3C[Si](C)(C)OC(=CS(=O)O)C(=O)O1543.6Semi standard non polar33892256
3-Sulfinylpyruvic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C(=O)CS(=O)O[Si](C)(C)C1552.4Semi standard non polar33892256
3-Sulfinylpyruvic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C(=O)CS(=O)O[Si](C)(C)C1591.8Standard non polar33892256
3-Sulfinylpyruvic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C(=O)CS(=O)O[Si](C)(C)C1752.0Standard polar33892256
3-Sulfinylpyruvic acid,2TMS,isomer #2C[Si](C)(C)OC(=O)C(=CS(=O)O)O[Si](C)(C)C1606.1Semi standard non polar33892256
3-Sulfinylpyruvic acid,2TMS,isomer #2C[Si](C)(C)OC(=O)C(=CS(=O)O)O[Si](C)(C)C1713.1Standard non polar33892256
3-Sulfinylpyruvic acid,2TMS,isomer #2C[Si](C)(C)OC(=O)C(=CS(=O)O)O[Si](C)(C)C2060.7Standard polar33892256
3-Sulfinylpyruvic acid,2TMS,isomer #3C[Si](C)(C)OC(=CS(=O)O[Si](C)(C)C)C(=O)O1639.9Semi standard non polar33892256
3-Sulfinylpyruvic acid,2TMS,isomer #3C[Si](C)(C)OC(=CS(=O)O[Si](C)(C)C)C(=O)O1848.9Standard non polar33892256
3-Sulfinylpyruvic acid,2TMS,isomer #3C[Si](C)(C)OC(=CS(=O)O[Si](C)(C)C)C(=O)O1931.2Standard polar33892256
3-Sulfinylpyruvic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C(=CS(=O)O[Si](C)(C)C)O[Si](C)(C)C1655.2Semi standard non polar33892256
3-Sulfinylpyruvic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C(=CS(=O)O[Si](C)(C)C)O[Si](C)(C)C1867.1Standard non polar33892256
3-Sulfinylpyruvic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C(=CS(=O)O[Si](C)(C)C)O[Si](C)(C)C1658.8Standard polar33892256
3-Sulfinylpyruvic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(=O)CS(=O)O1715.0Semi standard non polar33892256
3-Sulfinylpyruvic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OS(=O)CC(=O)C(=O)O1717.7Semi standard non polar33892256
3-Sulfinylpyruvic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=CS(=O)O)C(=O)O1801.5Semi standard non polar33892256
3-Sulfinylpyruvic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(=O)CS(=O)O[Si](C)(C)C(C)(C)C2006.7Semi standard non polar33892256
3-Sulfinylpyruvic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(=O)CS(=O)O[Si](C)(C)C(C)(C)C2113.7Standard non polar33892256
3-Sulfinylpyruvic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(=O)CS(=O)O[Si](C)(C)C(C)(C)C2000.5Standard polar33892256
3-Sulfinylpyruvic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(=CS(=O)O)O[Si](C)(C)C(C)(C)C2087.7Semi standard non polar33892256
3-Sulfinylpyruvic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(=CS(=O)O)O[Si](C)(C)C(C)(C)C2223.3Standard non polar33892256
3-Sulfinylpyruvic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(=CS(=O)O)O[Si](C)(C)C(C)(C)C2184.6Standard polar33892256
3-Sulfinylpyruvic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=CS(=O)O[Si](C)(C)C(C)(C)C)C(=O)O2130.8Semi standard non polar33892256
3-Sulfinylpyruvic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=CS(=O)O[Si](C)(C)C(C)(C)C)C(=O)O2291.7Standard non polar33892256
3-Sulfinylpyruvic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=CS(=O)O[Si](C)(C)C(C)(C)C)C(=O)O2116.8Standard polar33892256
3-Sulfinylpyruvic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(=CS(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2324.8Semi standard non polar33892256
3-Sulfinylpyruvic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(=CS(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2547.4Standard non polar33892256
3-Sulfinylpyruvic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(=CS(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2081.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Sulfinylpyruvic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0bvl-9300000000-b9d5aeadd8b7738b73532017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Sulfinylpyruvic acid GC-MS (1 TMS) - 70eV, Positivesplash10-0ab9-9600000000-56bba3bcd18999fead912017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Sulfinylpyruvic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Sulfinylpyruvic acid 10V, Positive-QTOFsplash10-0f89-0900000000-871c9b0796f2447470ed2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Sulfinylpyruvic acid 20V, Positive-QTOFsplash10-00li-9600000000-da362e24b25de10e7c3e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Sulfinylpyruvic acid 40V, Positive-QTOFsplash10-0006-9100000000-47872b5d21e6463c1ffc2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Sulfinylpyruvic acid 10V, Negative-QTOFsplash10-0udi-1900000000-d91ad6a6d2809d9a67142017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Sulfinylpyruvic acid 20V, Negative-QTOFsplash10-0fb9-9400000000-f213ed656a1bcd5e15542017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Sulfinylpyruvic acid 40V, Negative-QTOFsplash10-0w93-9400000000-7973a19a971bd544bf7e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Sulfinylpyruvic acid 10V, Positive-QTOFsplash10-0ulc-9600000000-23622faf57828eab4fed2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Sulfinylpyruvic acid 20V, Positive-QTOFsplash10-03dl-9000000000-4fae7c347514ef087b682021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Sulfinylpyruvic acid 40V, Positive-QTOFsplash10-01ox-9000000000-5f2edaa9051f5ab324ba2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Sulfinylpyruvic acid 10V, Negative-QTOFsplash10-000i-9000000000-9216d677abe9869648262021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Sulfinylpyruvic acid 20V, Negative-QTOFsplash10-03di-9000000000-64a44662186d1bb88d152021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Sulfinylpyruvic acid 40V, Negative-QTOFsplash10-0006-9000000000-16b11026ba456f1a6f3c2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Mitochondria
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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH ID3SNPYR
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceChatagner, Fernande; Bergeret, Bernadette; Fromageot, Claude. Transaminations taking part in the metabolism of cysteinesulfinic acid in mammals. Ann. Acad. Sci. Fennicae (1955), II;No.60(Ser. A), 393-400.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Griffith OW: Cysteinesulfinate metabolism. altered partitioning between transamination and decarboxylation following administration of beta-methyleneaspartate. J Biol Chem. 1983 Feb 10;258(3):1591-8. [PubMed:6822523 ]
  2. 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 ]
  3. 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
Reactions
3-Sulfinoalanine + Oxoglutaric acid → 3-Sulfinylpyruvic acid + L-Glutamic aciddetails
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
Reactions
3-Sulfinoalanine + Oxoglutaric acid → 3-Sulfinylpyruvic acid + L-Glutamic aciddetails