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Record Information
Version3.6
Creation Date2006-08-13 09:37:36 UTC
Update Date2016-02-11 01:06:32 UTC
HMDB IDHMDB04045
Secondary Accession Numbers
  • HMDB60174
Metabolite Identification
Common Name3-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, which is excreted in the urine. Cysteinesulfonate, 3-sulfopyruvic acid, and beta-sulfolactate are reversibly interconverted in vivo. (PMID: 3346220 ).
Structure
Thumb
Synonyms
ValueSource
2-Carboxy-2-oxoethanesulfonic acidHMDB
2-oxo-3-SulfO-propanoateHMDB
2-oxo-3-SulfO-propanoic acidHMDB
2-oxo-3-SulfopropanoateHMDB
2-oxo-3-Sulfopropanoic acidHMDB
3-SulfonatopyruvateHMDB
3-SulfopyruvateHMDB
beta-Sulfopyruvic acidHMDB
SulfopyruvateHMDB
Chemical FormulaC3H4O6S
Average Molecular Weight168.125
Monoisotopic Molecular Weight167.97285855
IUPAC Name2-oxo-3-sulfopropanoic acid
Traditional Namesulfopyruvate
CAS Registry Number98022-26-5
SMILES
OC(=O)C(=O)CS(O)(=O)=O
InChI Identifier
InChI=1S/C3H4O6S/c4-2(3(5)6)1-10(7,8)9/h1H2,(H,5,6)(H,7,8,9)
InChI KeyInChIKey=BUTHMSUEBYPMKJ-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
  • Alkanesulfonic acid
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonic acid
  • Alpha-hydroxy ketone
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-1.701Not Available
Predicted Properties
PropertyValueSource
Water Solubility12.9 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity28.33 m3·mol-1ChemAxon
Polarizability12.46 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, Positivesplash10-014i-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
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot 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 IDFDB023289
KNApSAcK IDNot Available
Chemspider ID389590
KEGG Compound IDC05528
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB04045
Metagene LinkHMDB04045
METLIN IDNot Available
PubChem Compound440717
PDB IDSPV
ChEBI ID16894
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [23455439 ]
  2. Weinstein CL, Griffith OW: Cysteinesulfonate and beta-sulfopyruvate metabolism. Partitioning between decarboxylation, transamination, and reduction pathways. J Biol Chem. 1988 Mar 15;263(8):3735-43. [3346220 ]

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
Cysteic acid + Oxoglutaric acid → 3-Sulfopyruvic 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
Cysteic acid + Oxoglutaric acid → 3-Sulfopyruvic acid + L-Glutamic aciddetails