Record Information
Version2.0
Creation Date2012-05-31 13:51:01 -0600
Update Date2015-09-13 12:56:11 -0600
Secondary Accession Numbers
  • ECMDB01368
Identification
Name:3-Mercaptopyruvic acid
Description3-Mercaptopyruvic acid is an intermediate in the metabolism of Cysteine and the production of hydrogen sulfide. It is a substrate for3-mercaptopyruvate sulfurtransferase which catalyzes the following reaction: H+ + 3-Mercaptopyruvic acid <=> Pyruvic acid + Hydrogen sulfide.
Structure
Thumb
Synonyms:
  • β-mercaptopyruvate
  • β-mercaptopyruvic acid
  • β-thiopyruvate
  • β-thiopyruvic acid
  • 3-Mercapto-pyruvate
  • 3-Mercapto-pyruvic acid
  • 3-Mercaptopyruvate
  • 3-Mercaptopyruvic acid
  • b-3-mercapto-2-oxo-Propanoate
  • b-3-mercapto-2-oxo-Propanoic acid
  • b-Mercaptopyruvate
  • b-Mercaptopyruvic acid
  • b-Thiopyruvate
  • b-Thiopyruvic acid
  • Beta-3-Mercapto-2-oxo-propanoate
  • Beta-3-Mercapto-2-oxo-propanoic acid
  • Beta-Mercaptopyruvate
  • Beta-Mercaptopyruvic acid
  • Beta-Thiopyruvate
  • Beta-Thiopyruvic acid
  • Mercaptopyruvate
  • Mercaptopyruvic acid
  • MercPyr
  • Thiopyruvate
  • Thiopyruvic acid
  • β-3-mercapto-2-oxo-Propanoate
  • β-3-mercapto-2-oxo-Propanoic acid
  • β-Mercaptopyruvate
  • β-Mercaptopyruvic acid
  • β-Thiopyruvate
  • β-Thiopyruvic acid
Chemical Formula:C3H4O3S
Weight:Average: 120.127
Monoisotopic: 119.988114684
InChI Key:OJOLFAIGOXZBCI-UHFFFAOYSA-N
InChI:InChI=1S/C3H4O3S/c4-2(1-7)3(5)6/h7H,1H2,(H,5,6)
CAS number:2464-23-5
IUPAC Name:2-oxo-3-sulfanylpropanoic acid
Traditional IUPAC Name:β-mercaptopyruvic acid
SMILES:OC(=O)C(=O)CS
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
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Alkylthiol
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility9.09 g/LALOGPS
logP0.15ALOGPS
logP0.29ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)2.91ChemAxon
pKa (Strongest Basic)-9.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity25.82 m³·mol⁻¹ChemAxon
Polarizability10.15 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Hydrogen Sulfide Biosynthesis IPW002066 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-9000000000-b81f8808977132c3a8acView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9300000000-5100fd5cbb3bf9df1e75View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-003r-9200000000-f1e0c53958ad51dc0068View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-001j-9000000000-60f6deb41f42078dd60cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-001i-9000000000-5dc69d3b59bd15290aefView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-2900000000-0da521157f8235fe7758View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fk9-7900000000-8c127be0565b54938cd2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-9000000000-d4a8d07d451ba309b2e2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-1900000000-849e74ceb9308736ba6dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gb9-2900000000-5a713232367a68a966a0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fk9-9300000000-564344466a63b943c6daView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
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
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID16208
HMDB IDHMDB01368
Pubchem Compound ID98
Kegg IDC00957
ChemSpider ID96
Wikipedia ID3-Mercaptopyruvic_acid
BioCyc ID3-MERCAPTO-PYRUVATE
EcoCyc ID3-MERCAPTO-PYRUVATE

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 thiosulfate sulfurtransferase activity
Specific function:
Transfers a sulfur ion to cyanide or to other thiol compounds. Also has weak rhodanese activity (130-fold lower). Its participation in detoxification of cyanide may be small. May be involved in the enhancement of serine sensitivity
Gene Name:
sseA
Uniprot ID:
P31142
Molecular weight:
30812
Reactions
3-mercaptopyruvate + cyanide = pyruvate + thiocyanate.
General function:
Involved in thiosulfate sulfurtransferase activity
Specific function:
Thiosulfate + cyanide = sulfite + thiocyanate
Gene Name:
ynjE
Uniprot ID:
P78067
Molecular weight:
48228
Reactions
Thiosulfate + cyanide = sulfite + thiocyanate.