3-Mercapto-2-oxopropanoic acid (CHEM034771)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:12:25 UTC
Update Date2016-11-09 01:21:11 UTC
Accession NumberCHEM034771
Identification
Common Name3-Mercapto-2-oxopropanoic acid
ClassSmall Molecule
Description3-3-3-mercaptopyruvic acid, also known as 3-mercaptopyruvic acid or 3-3-mercaptopyruvic acid, 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. 3-3-3-mercaptopyruvic acid is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 3-3-3-mercaptopyruvic acid exists in all living organisms, ranging from bacteria to humans. 3-3-3-mercaptopyruvic acid participates in a number of enzymatic reactions, within cattle. In particular, 3-3-3-mercaptopyruvic acid and cyanide can be converted into pyruvic acid and thiocyanate through its interaction with the enzyme 3-3-mercaptopyruvic acid sulfurtransferase. In addition, 3-3-3-mercaptopyruvic acid can be biosynthesized from 3-mercaptolactic acid; which is catalyzed by the enzyme L-lactate dehydrogenase. In cattle, 3-3-mercaptopyruvic acid is involved in the metabolic pathway called the cysteine metabolism pathway.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
3-Mercapto-2-oxopropanoic acidChEBI
3-MercaptopyruvateChEBI
MercaptopyruvateChEBI
3-Mercapto-2-oxopropanoateGenerator
Mercaptopyruvic acidGenerator
3-Mercapto-pyruvateHMDB
3-Mercapto-pyruvic acidHMDB
beta-3-Mercapto-2-oxo-propanoateHMDB
beta-3-Mercapto-2-oxo-propanoic acidHMDB
beta-MercaptopyruvateHMDB
beta-Mercaptopyruvic acidHMDB
beta-ThiopyruvateHMDB
beta-Thiopyruvic acidHMDB
ThiopyruvateHMDB
3-Mercaptopyruvate monosodium saltHMDB
Chemical FormulaC3H4O3S
Average Molecular Mass120.127 g/mol
Monoisotopic Mass119.988 g/mol
CAS Registry Number2464-23-5
IUPAC Name2-oxo-3-sulfanylpropanoic acid
Traditional Nameβ-mercaptopyruvic acid
SMILESOC(=O)C(=O)CS
InChI IdentifierInChI=1S/C3H4O3S/c4-2(1-7)3(5)6/h7H,1H2,(H,5,6)
InChI KeyOJOLFAIGOXZBCI-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
  • 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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-9000000000-b81f8808977132c3a8acSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9300000000-5100fd5cbb3bf9df1e75Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-003r-9200000000-f1e0c53958ad51dc0068Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-001j-9000000000-60f6deb41f42078dd60cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-001i-9000000000-5dc69d3b59bd15290aefSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-02t9-9000000000-e1511333b005fa911312Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-00kf-9000000000-65854057c742d34c8dbbSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-006w-9000000000-66939f30bca1061b4b83Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-2900000000-0da521157f8235fe7758Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fk9-7900000000-8c127be0565b54938cd2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-9000000000-d4a8d07d451ba309b2e2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-1900000000-849e74ceb9308736ba6dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gb9-2900000000-5a713232367a68a966a0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fk9-9300000000-564344466a63b943c6daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-006x-9200000000-95772f7f626a811df489Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9000000000-32551e3b5faf0b1e7000Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9000000000-572c315b879edca344faSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-9400000000-8738d67598547a4b3429Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-4ba1ab7a6a1dc95bba23Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9000000000-6a9a04efc4b7bb2af1ebSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0001368
FooDB IDFDB030434
Phenol Explorer IDNot Available
KNApSAcK IDC00007464
BiGG ID36476
BioCyc ID3-MERCAPTO-PYRUVATE
METLIN ID6195
PDB IDNot Available
Wikipedia Link3-Mercaptopyruvic_acid
Chemspider ID96
ChEBI ID16208
PubChem Compound ID98
Kegg Compound IDC00957
YMDB IDNot Available
ECMDB IDECMDB01368
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=7054184