Human Metabolome Database Version 3.5

Showing metabocard for 3-Mercaptopyruvic acid (HMDB01368)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:10:25 -0700
HMDB ID HMDB01368
Secondary Accession Numbers None
Metabolite Identification
Common Name 3-Mercaptopyruvic acid
Description 3-Mercaptopyruvic acid is an intermediate in the metabolism of Cysteine. It is a substrate for L-lactate dehydrogenase A chain, 3-mercaptopyruvate sulfurtransferase, Aspartate aminotransferase (mitochondrial), L-lactate dehydrogenase C chain, L-lactate dehydrogenase A-like 6A, Aspartate aminotransferase (cytoplasmic), L-lactate dehydrogenase B chain and L-lactate dehydrogenase A-like 6B.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 3-Mercapto-pyruvate
  2. 3-Mercapto-pyruvic acid
  3. 3-Mercaptopyruvate
  4. 3-Mercaptopyruvic acid
  5. beta-3-Mercapto-2-oxo-propanoate
  6. beta-3-Mercapto-2-oxo-propanoic acid
  7. beta-Mercaptopyruvate
  8. beta-Mercaptopyruvic acid
  9. beta-Thiopyruvate
  10. beta-Thiopyruvic acid
  11. Mercaptopyruvate
  12. Mercaptopyruvic acid
  13. Thiopyruvate
Chemical Formula C3H4O3S
Average Molecular Weight 120.127
Monoisotopic Molecular Weight 119.988114684
IUPAC Name 2-oxo-3-sulfanylpropanoic acid
Traditional IUPAC Name 3-mercaptopyruvic acid
CAS Registry Number 2464-23-5
SMILES OC(=O)C(=O)CS
InChI Identifier InChI=1S/C3H4O3S/c4-2(1-7)3(5)6/h7H,1H2,(H,5,6)
InChI Key OJOLFAIGOXZBCI-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Organic Acids and Derivatives
Class Keto-Acids and Derivatives
Sub Class Alpha Keto-Acids and Derivatives
Other Descriptors
  • 2-oxo monocarboxylic acid(ChEBI)
  • Aliphatic Acyclic Compounds
Substituents
  • Alkylthiol
  • Carboxylic Acid
  • Ketone
  • Thiol (Sulfanyl Compound)
Direct Parent Alpha Keto-Acids and Derivatives
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Component of Cysteine metabolism
Application Not Available
Cellular locations
  • Mitochondria
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 9.09 g/L ALOGPS
LogP 0.15 ALOGPS
LogP 0.29 ChemAxon
LogS -1.12 ALOGPS
pKa (strongest acidic) 2.91 ChemAxon
pKa (strongest basic) -9.8 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 54.37 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 25.82 ChemAxon
Polarizability 10.15 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Mitochondria
Biofluid Locations Not Available
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Cysteine Metabolism SMP00013 map00270 Link_out
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB021862
KNApSAcK ID C00007464 Link_out
Chemspider ID 96 Link_out
KEGG Compound ID C00957 Link_out
BioCyc ID 3-MERCAPTO-PYRUVATE Link_out
BiGG ID 36476 Link_out
Wikipedia Link Not Available
NuGOwiki Link HMDB01368 Link_out
Metagene Link HMDB01368 Link_out
METLIN ID 6195 Link_out
PubChem Compound 98 Link_out
PDB ID Not Available
ChEBI ID 16208 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
General References Not Available

Enzymes
Name: Aspartate aminotransferase, cytoplasmic
Reactions:
L-Cysteine + Oxoglutaric acid unknown 3-Mercaptopyruvic acid + DL-Glutamate details
Gene Name: GOT1
Uniprot ID: P17174 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aspartate aminotransferase, mitochondrial
Reactions:
L-Cysteine + Oxoglutaric acid unknown 3-Mercaptopyruvic acid + DL-Glutamate details
Gene Name: GOT2
Uniprot ID: P00505 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cystathionine gamma-lyase
Reactions: Not Available
Gene Name: CTH
Uniprot ID: P32929 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 3-mercaptopyruvate sulfurtransferase
Reactions:
3-Mercaptopyruvic acid + Hydrogen cyanide unknown Pyruvic acid + Thiocyanate details
3-Mercaptopyruvic acid + Sulfurous acid unknown Thiosulfate + Pyruvic acid details
Gene Name: MPST
Uniprot ID: P25325 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: L-lactate dehydrogenase A-like 6A
Reactions:
3-Mercaptolactic acid + NAD unknown 3-Mercaptopyruvic acid + NADH + Hydrogen Ion details
Gene Name: LDHAL6A
Uniprot ID: Q6ZMR3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Thiosulfate sulfurtransferase
Reactions:
3-Mercaptopyruvic acid + Sulfurous acid unknown Thiosulfate + Pyruvic acid details
Hydrogen cyanide + 3-Mercaptopyruvic acid unknown Thiocyanate + Pyruvic acid details
Gene Name: TST
Uniprot ID: Q16762 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: L-lactate dehydrogenase B chain
Reactions:
3-Mercaptolactic acid + NAD unknown 3-Mercaptopyruvic acid + NADH + Hydrogen Ion details
Gene Name: LDHB
Uniprot ID: P07195 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: L-lactate dehydrogenase C chain
Reactions:
3-Mercaptolactic acid + NAD unknown 3-Mercaptopyruvic acid + NADH + Hydrogen Ion details
Gene Name: LDHC
Uniprot ID: P07864 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: L-lactate dehydrogenase A chain
Reactions:
3-Mercaptolactic acid + NAD unknown 3-Mercaptopyruvic acid + NADH + Hydrogen Ion details
Gene Name: LDHA
Uniprot ID: P00338 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: L-lactate dehydrogenase A-like 6B
Reactions:
3-Mercaptolactic acid + NAD unknown 3-Mercaptopyruvic acid + NADH + Hydrogen Ion details
Gene Name: LDHAL6B
Uniprot ID: Q9BYZ2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA