Record Information
Version2.0
Creation Date2012-05-31 14:54:00 -0600
Update Date2015-06-03 17:20:24 -0600
Secondary Accession Numbers
  • ECMDB21002
Identification
Name:3-Sulfopyruvic acid
Description3-Sulfopyruvic acid is the product of the transamination of cysteinesulfonate in a reaction catalyzed by aspartate aminotransferase. 3-sulfopyruvic acid is stable and is reduced by malate dehydrogenase to beta-sulfolactate. Cysteinesulfonate, 3-sulfopyruvic acid, and beta-sulfolactate are reversibly interconverted in vivo. (PMID: 3346220)
Structure
Thumb
Synonyms:
  • 2-Carboxy-2-oxoethanesulfonate
  • 2-Carboxy-2-oxoethanesulfonic acid
  • 2-Carboxy-2-oxoethanesulphonate
  • 2-Carboxy-2-oxoethanesulphonic acid
  • 2-Oxo-3-sulfo-Propanoate
  • 2-Oxo-3-sulfo-Propanoic acid
  • 2-Oxo-3-sulfopropanoate
  • 2-Oxo-3-sulfopropanoic acid
  • 2-Oxo-3-sulpho-Propanoate
  • 2-Oxo-3-sulpho-Propanoic acid
  • 2-Oxo-3-sulphopropanoate
  • 2-Oxo-3-sulphopropanoic acid
  • 3-Sulfopyruvate
  • 3-Sulfopyruvic acid
  • 3-Sulphopyruvate
  • 3-Sulphopyruvic acid
  • b-Sulfopyruvate
  • b-Sulfopyruvic acid
  • b-Sulphopyruvate
  • b-Sulphopyruvic acid
  • Beta-Sulfopyruvate
  • Beta-Sulfopyruvic acid
  • Beta-Sulphopyruvate
  • Beta-Sulphopyruvic acid
  • Sulfopyruvate
  • Sulfopyruvic acid
  • Sulphopyruvate
  • Sulphopyruvic acid
  • β-Sulfopyruvate
  • β-Sulfopyruvic acid
  • β-Sulphopyruvate
  • β-Sulphopyruvic acid
Chemical Formula:C3H4O6S
Weight:Average: 168.125
Monoisotopic: 167.97285855
InChI Key:BUTHMSUEBYPMKJ-UHFFFAOYSA-N
InChI:InChI=1S/C3H4O6S/c4-2(3(5)6)1-10(7,8)9/h1H2,(H,5,6)(H,7,8,9)
CAS number:98022-26-5
IUPAC Name:2-oxo-3-sulfopropanoic acid
Traditional IUPAC Name:sulfopyruvate
SMILES:OC(=O)C(=O)CS(O)(=O)=O
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
  • Alkanesulfonic acid
  • Sulfonyl
  • Organosulfonic acid
  • Organosulfonic acid or derivatives
  • Organic sulfonic acid or derivatives
  • Ketone
  • 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
Physical Properties
State:Solid
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
LogP:-1.701PhysProp
Predicted Properties
PropertyValueSource
Water Solubility12.9 g/LALOGPS
logP-1.5ALOGPS
logP-0.74ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)-1.8ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area108.74 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity28.33 m³·mol⁻¹ChemAxon
Polarizability12.46 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Collection of Reactions without pathwaysPW001891 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Cysteine and methionine metabolism ec00270
  • Methane metabolism ec00680
  • Microbial metabolism in diverse environments ec01120
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9300000000-8fb65d208d027ce47187View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9310000000-852dd197381758581de3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-094511841526eb040890View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0g4i-2900000000-77b615b663328d3fe524View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9500000000-bf672301532b1817de74View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-4e67b7b2992779903679View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-3900000000-9801b0e1faeb0f73a93bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-7900000000-7a1af7df664000361846View in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 Mar 3. doi: 10.1038/nbt.2488. Pubmed: 23455439
  • Weinstein, C. L., Griffith, O. W. (1988). "Cysteinesulfonate and beta-sulfopyruvate metabolism. Partitioning between decarboxylation, transamination, and reduction pathways." J Biol Chem 263:3735-3743. Pubmed: 3346220
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID16894
HMDB IDHMDB04045
Pubchem Compound ID440717
Kegg IDC05528
ChemSpider ID389590
Wikipedia IDNot Available
BioCyc IDNot Available
Ligand ExpoSPV

Enzymes

General function:
Involved in transferase activity
Specific function:
L-aspartate + 2-oxoglutarate = oxaloacetate + L-glutamate
Gene Name:
aspC
Uniprot ID:
P00509
Molecular weight:
43573
Reactions
L-aspartate + 2-oxoglutarate = oxaloacetate + L-glutamate.
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Catalyzes the reversible oxidation of malate to oxaloacetate
Gene Name:
mdh
Uniprot ID:
P61889
Molecular weight:
32337
Reactions
(S)-malate + NAD(+) = oxaloacetate + NADH.
General function:
Involved in transporter activity
Specific function:
Part of a binding-protein-dependent transport system for aliphatic sulfonates. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
ssuC
Uniprot ID:
P75851
Molecular weight:
28925

Transporters

General function:
Involved in transporter activity
Specific function:
Part of a binding-protein-dependent transport system for aliphatic sulfonates. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
ssuC
Uniprot ID:
P75851
Molecular weight:
28925