Record Information
Version1.0
Creation date2011-06-15 17:54:18 UTC
Update date2020-04-21 18:02:15 UTC
Primary IDFDB021862
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3-Mercapto-2-oxopropanoic acid
Description3-Mercaptopyruvic acid, also known as beta-thiopyruvate or 3-mercapto-2-oxopropanoate, 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-Mercaptopyruvic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 3-Mercaptopyruvic acid exists in all living organisms, ranging from bacteria to humans. 3-Mercaptopyruvic acid has been detected, but not quantified in, several different foods, such as half-highbush blueberries, bitter gourds, new zealand spinachs, horseradish tree, and red huckleberries. This could make 3-mercaptopyruvic acid a potential biomarker for the consumption of these foods.
CAS Number2464-23-5
Structure
Thumb
Synonyms
SynonymSource
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
3-Mercaptopyruvic acidChEBI
b-Mercaptopyruvic aciddb_source
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC3H4O3S
IUPAC name2-oxo-3-sulfanylpropanoic acid
InChI IdentifierInChI=1S/C3H4O3S/c4-2(1-7)3(5)6/h7H,1H2,(H,5,6)
InChI KeyOJOLFAIGOXZBCI-UHFFFAOYSA-N
Isomeric SMILESOC(=O)C(=O)CS
Average Molecular Weight120.127
Monoisotopic Molecular Weight119.988114684
Classification
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
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionCryst. (Me2CO/petrol)CCD
Mass CompositionC 30.00%; H 3.36%; O 39.96%; S 26.69%CCD
Melting PointMp 140-141°CCD
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS3-Mercapto-2-oxopropanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-9000000000-b81f8808977132c3a8acSpectrum
Predicted GC-MS3-Mercapto-2-oxopropanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-9300000000-5100fd5cbb3bf9df1e75Spectrum
Predicted GC-MS3-Mercapto-2-oxopropanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Mercapto-2-oxopropanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-003r-9200000000-f1e0c53958ad51dc00682012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-001j-9000000000-60f6deb41f42078dd60c2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-001i-9000000000-5dc69d3b59bd15290aef2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-02t9-9000000000-e1511333b005fa9113122021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-00kf-9000000000-65854057c742d34c8dbb2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-006w-9000000000-66939f30bca1061b4b832021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-2900000000-0da521157f8235fe77582017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fk9-7900000000-8c127be0565b54938cd22017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-9000000000-d4a8d07d451ba309b2e22017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-1900000000-849e74ceb9308736ba6d2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gb9-2900000000-5a713232367a68a966a02017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fk9-9300000000-564344466a63b943c6da2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-006x-9200000000-95772f7f626a811df4892021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9000000000-32551e3b5faf0b1e70002021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9000000000-572c315b879edca344fa2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-9400000000-8738d67598547a4b34292021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-4ba1ab7a6a1dc95bba232021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9000000000-6a9a04efc4b7bb2af1eb2021-09-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID96
ChEMBL IDNot Available
KEGG Compound IDC00957
Pubchem Compound ID98
Pubchem Substance IDNot Available
ChEBI ID16208
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01368
CRC / DFC (Dictionary of Food Compounds) IDNRC89-Q:NRC89-Q
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID36476
KNApSAcK IDC00007464
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia ID3-Mercaptopyruvic_acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Aspartate aminotransferase, cytoplasmicGOT1P17174
Aspartate aminotransferase, mitochondrialGOT2P00505
3-mercaptopyruvate sulfurtransferaseMPSTP25325
Cystathionine gamma-lyaseCTHP32929
Pathways
NameSMPDB LinkKEGG Link
Cysteine MetabolismSMP00013 map00270
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference