Showing metabocard for 3-Mercaptopyruvic acid (BMDB0001368)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:44:49 UTC
Update Date2020-05-21 16:28:31 UTC
BMDB IDBMDB0001368
Secondary Accession Numbers
  • BMDB01368
Metabolite Identification
Common Name3-Mercaptopyruvic acid
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.
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 Weight120.127
Monoisotopic Molecular Weight119.988114684
IUPAC Name2-oxo-3-sulfanylpropanoic acid
Traditional Nameβ-mercaptopyruvic acid
CAS Registry Number2464-23-5
SMILES
OC(=O)C(=O)CS
InChI Identifier
InChI=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
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
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
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-02t9-9000000000-e1511333b005fa911312View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-00kf-9000000000-65854057c742d34c8dbbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-006w-9000000000-66939f30bca1061b4b83View 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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-006x-9200000000-95772f7f626a811df489View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9000000000-32551e3b5faf0b1e7000View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9000000000-572c315b879edca344faView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-9400000000-8738d67598547a4b3429View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-4ba1ab7a6a1dc95bba23View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9000000000-6a9a04efc4b7bb2af1ebView in MoNA
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0001368
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB030434
KNApSAcK IDC00007464
Chemspider ID96
KEGG Compound IDC00957
BioCyc ID3-MERCAPTO-PYRUVATE
BiGG ID36476
Wikipedia Link3-Mercaptopyruvic_acid
METLIN ID6195
PubChem Compound98
PDB IDNot Available
ChEBI ID16208
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Thiosulfate sulfurtransferase
General function:
Inorganic ion transport and metabolism
Specific function:
Together with MRPL18, acts as a mitochondrial import factor for the cytosolic 5S rRNA. Only the nascent unfolded cytoplasmic form is able to bind to the 5S rRNA (By similarity). Formation of iron-sulfur complexes and cyanide detoxification. Binds molecular oxygen and sulfur.
Gene Name:
TST
Uniprot ID:
P00586
Molecular weight:
33296.0
Reactions
3-Mercaptopyruvic acid + Cyanide → Pyruvic acid + Thiocyanatedetails
Enzyme Details
2. Aspartate aminotransferase, cytoplasmic
General function:
Amino acid transport and metabolism
Specific function:
Biosynthesis of L-glutamate from L-aspartate or L-cysteine. Important regulator of levels of glutamate, the major excitatory neurotransmitter of the vertebrate central nervous system. Acts as a scavenger of glutamate in brain neuroprotection. The aspartate aminotransferase activity is involved in hepatic glucose synthesis during development and in adipocyte glyceroneogenesis. Using L-cysteine as substrate, regulates levels of mercaptopyruvate, an important source of hydrogen sulfide. Mercaptopyruvate is converted into H(2)S via the action of 3-mercaptopyruvate sulfurtransferase (3MST). Hydrogen sulfide is an important synaptic modulator and neuroprotectant in the brain (By similarity).
Gene Name:
GOT1
Uniprot ID:
P33097
Molecular weight:
46399.0
Reactions
L-Cysteine + Oxoglutaric acid → 3-Mercaptopyruvic acid + L-Glutamic aciddetails