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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-07 16:45:29 UTC
HMDB IDHMDB0001368
Secondary Accession Numbers
  • HMDB01368
Metabolite Identification
Common Name3-Mercaptopyruvic acid
Description3-Mercaptopyruvic acid, also known as 3-mercapto-2-oxopropanoate or beta-thiopyruvate, 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 intermediate in cysteine metabolism. 3-Mercaptopyruvic acid exists in all living organisms, ranging from bacteria to humans. Within humans, 3-mercaptopyruvic acid participates in a number of enzymatic reactions. In particular, 3-mercaptopyruvic acid and cyanide can be converted into pyruvic acid and thiocyanate; which is mediated by the enzyme 3-mercaptopyruvate sulfurtransferase. In addition, 3-mercaptopyruvic acid can be biosynthesized from 3-mercaptolactic acid; which is mediated by the enzyme L-lactate dehydrogenase. It has been studied as a potential treatment for cyanide poisoning, but its half-life is too short for it to be clinically effective. In humans, 3-mercaptopyruvic acid is involved in cystinosis, ocular nonnephropathic. Outside of the human body, 3-mercaptopyruvic acid has been detected, but not quantified in several different foods, such as lima beans, spinachs, shallots, mexican groundcherries, and white lupines. This could make 3-mercaptopyruvic acid a potential biomarker for the consumption of these foods.
Structure
Data?1582752196
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
Physiological effect

Adverse health effect

Disposition

Biological location

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+123.67831661259
DarkChem[M-H]-116.78231661259
AllCCS[M+H]+128.5932859911
AllCCS[M-H]-126.92132859911
DeepCCS[M+H]+123.60230932474
DeepCCS[M-H]-121.70230932474
DeepCCS[M-2H]-157.29730932474
DeepCCS[M+Na]+131.84330932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Mercaptopyruvic acidOC(=O)C(=O)CS2243.4Standard polar33892256
3-Mercaptopyruvic acidOC(=O)C(=O)CS1526.8Standard non polar33892256
3-Mercaptopyruvic acidOC(=O)C(=O)CS1091.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Mercaptopyruvic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)C(=O)CS1154.9Semi standard non polar33892256
3-Mercaptopyruvic acid,1TMS,isomer #2C[Si](C)(C)SCC(=O)C(=O)O1329.6Semi standard non polar33892256
3-Mercaptopyruvic acid,1TMS,isomer #3C[Si](C)(C)OC(=CS)C(=O)O1304.1Semi standard non polar33892256
3-Mercaptopyruvic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C(=O)CS[Si](C)(C)C1433.2Semi standard non polar33892256
3-Mercaptopyruvic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C(=O)CS[Si](C)(C)C1379.7Standard non polar33892256
3-Mercaptopyruvic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C(=O)CS[Si](C)(C)C1509.4Standard polar33892256
3-Mercaptopyruvic acid,2TMS,isomer #2C[Si](C)(C)OC(=O)C(=CS)O[Si](C)(C)C1467.7Semi standard non polar33892256
3-Mercaptopyruvic acid,2TMS,isomer #2C[Si](C)(C)OC(=O)C(=CS)O[Si](C)(C)C1462.3Standard non polar33892256
3-Mercaptopyruvic acid,2TMS,isomer #2C[Si](C)(C)OC(=O)C(=CS)O[Si](C)(C)C1478.6Standard polar33892256
3-Mercaptopyruvic acid,2TMS,isomer #3C[Si](C)(C)OC(=CS[Si](C)(C)C)C(=O)O1530.1Semi standard non polar33892256
3-Mercaptopyruvic acid,2TMS,isomer #3C[Si](C)(C)OC(=CS[Si](C)(C)C)C(=O)O1527.9Standard non polar33892256
3-Mercaptopyruvic acid,2TMS,isomer #3C[Si](C)(C)OC(=CS[Si](C)(C)C)C(=O)O1696.9Standard polar33892256
3-Mercaptopyruvic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C(=CS[Si](C)(C)C)O[Si](C)(C)C1565.2Semi standard non polar33892256
3-Mercaptopyruvic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C(=CS[Si](C)(C)C)O[Si](C)(C)C1471.0Standard non polar33892256
3-Mercaptopyruvic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C(=CS[Si](C)(C)C)O[Si](C)(C)C1516.9Standard polar33892256
3-Mercaptopyruvic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(=O)CS1417.6Semi standard non polar33892256
3-Mercaptopyruvic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)SCC(=O)C(=O)O1585.6Semi standard non polar33892256
3-Mercaptopyruvic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=CS)C(=O)O1542.2Semi standard non polar33892256
3-Mercaptopyruvic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(=O)CS[Si](C)(C)C(C)(C)C1883.1Semi standard non polar33892256
3-Mercaptopyruvic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(=O)CS[Si](C)(C)C(C)(C)C1825.3Standard non polar33892256
3-Mercaptopyruvic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(=O)CS[Si](C)(C)C(C)(C)C1793.1Standard polar33892256
3-Mercaptopyruvic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(=CS)O[Si](C)(C)C(C)(C)C1883.6Semi standard non polar33892256
3-Mercaptopyruvic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(=CS)O[Si](C)(C)C(C)(C)C1890.7Standard non polar33892256
3-Mercaptopyruvic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(=CS)O[Si](C)(C)C(C)(C)C1756.8Standard polar33892256
3-Mercaptopyruvic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=CS[Si](C)(C)C(C)(C)C)C(=O)O1961.7Semi standard non polar33892256
3-Mercaptopyruvic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=CS[Si](C)(C)C(C)(C)C)C(=O)O1949.3Standard non polar33892256
3-Mercaptopyruvic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=CS[Si](C)(C)C(C)(C)C)C(=O)O1904.8Standard polar33892256
3-Mercaptopyruvic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(=CS[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2188.3Semi standard non polar33892256
3-Mercaptopyruvic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(=CS[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2057.9Standard non polar33892256
3-Mercaptopyruvic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(=CS[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1929.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Mercaptopyruvic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-9000000000-b81f8808977132c3a8ac2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Mercaptopyruvic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9300000000-5100fd5cbb3bf9df1e752017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Mercaptopyruvic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Mercaptopyruvic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Mercaptopyruvic acid Quattro_QQQ 10V, Negative-QTOF (Annotated)splash10-003r-9200000000-f1e0c53958ad51dc00682012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Mercaptopyruvic acid Quattro_QQQ 25V, Negative-QTOF (Annotated)splash10-001j-9000000000-60f6deb41f42078dd60c2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Mercaptopyruvic acid Quattro_QQQ 40V, Negative-QTOF (Annotated)splash10-001i-9000000000-5dc69d3b59bd15290aef2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Mercaptopyruvic acid 40V, Negative-QTOFsplash10-02t9-9000000000-e1511333b005fa9113122021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Mercaptopyruvic acid 20V, Negative-QTOFsplash10-00kf-9000000000-65854057c742d34c8dbb2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Mercaptopyruvic acid 10V, Negative-QTOFsplash10-006w-9000000000-66939f30bca1061b4b832021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Mercaptopyruvic acid 10V, Positive-QTOFsplash10-0fk9-2900000000-0da521157f8235fe77582017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Mercaptopyruvic acid 20V, Positive-QTOFsplash10-0fk9-7900000000-8c127be0565b54938cd22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Mercaptopyruvic acid 40V, Positive-QTOFsplash10-0ab9-9000000000-d4a8d07d451ba309b2e22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Mercaptopyruvic acid 10V, Negative-QTOFsplash10-014i-1900000000-849e74ceb9308736ba6d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Mercaptopyruvic acid 20V, Negative-QTOFsplash10-0gb9-2900000000-5a713232367a68a966a02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Mercaptopyruvic acid 40V, Negative-QTOFsplash10-0fk9-9300000000-564344466a63b943c6da2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Mercaptopyruvic acid 10V, Negative-QTOFsplash10-006x-9200000000-95772f7f626a811df4892021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Mercaptopyruvic acid 20V, Negative-QTOFsplash10-001i-9000000000-32551e3b5faf0b1e70002021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Mercaptopyruvic acid 40V, Negative-QTOFsplash10-001i-9000000000-572c315b879edca344fa2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Mercaptopyruvic acid 10V, Positive-QTOFsplash10-00di-9400000000-8738d67598547a4b34292021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Mercaptopyruvic acid 20V, Positive-QTOFsplash10-00di-9000000000-4ba1ab7a6a1dc95bba232021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Mercaptopyruvic acid 40V, Positive-QTOFsplash10-0002-9000000000-6a9a04efc4b7bb2af1eb2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Mitochondria
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.0400-0.310 umol/mmol creatinineNot SpecifiedBothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.72 umol/mmol creatinineAdult (>18 years old)FemaleBeta-mercaptolactate-cysteine Disulfiduria details
Associated Disorders and Diseases
Disease References
Beta-mercaptolactate-cysteine Disulfiduria
  1. Hannestad U, Martensson J, Sjodahl R, Sorbo B: 3-mercaptolactate cysteine disulfiduria: biochemical studies on affected and unaffected members of a family. Biochem Med. 1981 Aug;26(1):106-14. [PubMed:6945862 ]
Associated OMIM IDs
  • 249650 (Beta-mercaptolactate-cysteine Disulfiduria)
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
Food Biomarker OntologyNot Available
VMH IDMERCPPYR
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

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
L-Cysteine + Oxoglutaric acid → 3-Mercaptopyruvic acid + DL-Glutamatedetails
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
L-Cysteine + Oxoglutaric acid → 3-Mercaptopyruvic acid + DL-Glutamatedetails
General function:
Involved in pyridoxal phosphate binding
Specific function:
Catalyzes the last step in the trans-sulfuration pathway from methionine to cysteine. Has broad substrate specificity. Converts cystathionine to cysteine, ammonia and 2-oxobutanoate. Converts two cysteine molecules to lanthionine and hydrogen sulfide. Can also accept homocysteine as substrate. Specificity depends on the levels of the endogenous substrates. Generates the endogenous signaling molecule hydrogen sulfide (H2S), and so contributes to the regulation of blood pressure. Acts as a cysteine-protein sulfhydrase by mediating sulfhydration of target proteins: sulfhydration consists of converting -SH groups into -SSH on specific cysteine residues of target proteins such as GAPDH, PTPN1 and NF-kappa-B subunit RELA, thereby regulating their function.
Gene Name:
CTH
Uniprot ID:
P32929
Molecular weight:
41259.91
General function:
Involved in thiosulfate sulfurtransferase activity
Specific function:
Transfer of a sulfur ion to cyanide or to other thiol compounds. Also has weak rhodanese activity. May have a role in cyanide degradation or in thiosulfate biosynthesis.
Gene Name:
MPST
Uniprot ID:
P25325
Molecular weight:
33178.15
Reactions
3-Mercaptopyruvic acid + Hydrogen cyanide → Pyruvic acid + Thiocyanatedetails
3-Mercaptopyruvic acid + Sulfite → Thiosulfate + Pyruvic aciddetails
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Displays an lactate dehydrogenase activity. Significantly increases the transcriptional activity of JUN, when overexpressed.
Gene Name:
LDHAL6A
Uniprot ID:
Q6ZMR3
Molecular weight:
36507.015
Reactions
3-Mercaptolactic acid + NAD → 3-Mercaptopyruvic acid + NADH + Hydrogen Iondetails
General function:
Involved in thiosulfate sulfurtransferase activity
Specific function:
Formation of iron-sulfur complexes, cyanide detoxification or modification of sulfur-containing enzymes. Other thiol compounds, besides cyanide, can act as sulfur ion acceptors. Also has weak mercaptopyruvate sulfurtransferase (MST) activity (By similarity). 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.
Gene Name:
TST
Uniprot ID:
Q16762
Molecular weight:
33428.69
Reactions
3-Mercaptopyruvic acid + Sulfite → Thiosulfate + Pyruvic aciddetails
Hydrogen cyanide + 3-Mercaptopyruvic acid → Thiocyanate + Pyruvic aciddetails
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Not Available
Gene Name:
LDHB
Uniprot ID:
P07195
Molecular weight:
36638.225
Reactions
3-Mercaptolactic acid + NAD → 3-Mercaptopyruvic acid + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Possible role in sperm motility.
Gene Name:
LDHC
Uniprot ID:
P07864
Molecular weight:
36310.965
Reactions
3-Mercaptolactic acid + NAD → 3-Mercaptopyruvic acid + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Not Available
Gene Name:
LDHA
Uniprot ID:
P00338
Molecular weight:
30204.975
Reactions
3-Mercaptolactic acid + NAD → 3-Mercaptopyruvic acid + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Not Available
Gene Name:
LDHAL6B
Uniprot ID:
Q9BYZ2
Molecular weight:
41942.53
Reactions
3-Mercaptolactic acid + NAD → 3-Mercaptopyruvic acid + NADH + Hydrogen Iondetails