Mercaptopyruvate (BioCAD00000013869)

urine

Metabolite Card

Formula: C3H4O3S (119.9881)
SMILES: OC(=O)C(=O)CS

Synonyms [en]

Mercaptopyruvate; 3-Mercaptopyruvate; 3-Mercaptopyruvic acid; 2-oxo-3-sulfanylpropanoic acid; 3-mercapto-2-oxopropanoic acid; 3-MERCAPTO-PYRUVATE

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Mercaptopyruvate. 数据之源,洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000013869). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

3-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.

Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 10255-67-1
  • CAS Registry Number: 2464-23-5
  • PubChem: 98
  • ChEBI: ChEBI:16208
  • HMDB: HMDB0001368
  • KEGG: C00957
  • BioCyc: 3-MERCAPTO-PYRUVATE
  • NCBI MeSH: 3-mercaptopyruvic acid
  • Wikipedia: 3-Mercaptopyruvic_acid
  • RefMet: RM0118177
  • MoNA: HMDB0001368_ms_ms_1534
  • MoNA: HMDB0001368_ms_ms_1535
  • MoNA: HMDB0001368_ms_ms_1536
  • MoNA: MoNA034600
  • MoNA: MoNA034601
  • MoNA: MoNA034603
  • MoNA: MoNA038070
  • Metlin: METLIN_4200

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R00895 2.6.1.1 L-cysteine:2-oxoglutarate aminotransferase
KEGG:R00896 2.6.1.1 L-cysteine:2-oxoglutarate aminotransferase
KEGG:R03104 1.1.1.27 3-mercaptolactate:NAD+ oxidoreductase
KEGG:R03105 2.8.1.2 3-mercaptopyruvate:sulfide sulfurtransferase
KEGG:R12689 2.8.1.2 C00957 + C02743<=>C00022 + C21440
BioCyc:CYSTEINE-AMINOTRANSFERASE-RXN 2.6.1.3 2-KETOGLUTARATE + CYS<=>GLT + 3-MERCAPTO-PYRUVATE
BioCyc:MERCAPYSTRANS-RXN 2.8.1.2 3-MERCAPTO-PYRUVATE + Red-Thioredoxin --> PYRUVATE + HS + Ox-Thioredoxin
BioCyc:RXN-18702 3-MERCAPTO-PYRUVATE + TUM1-L-cysteine --> TUM1-S-sulfanylcysteine + PYRUVATE
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Organism Source

Taxonomy Source

Pathway Synthetic

pathway id name
PathBank:SMP0002078 Hydrogen Sulfide Biosynthesis I
Plant Reactome:R-OAU-2744345 Metabolism and regulation
Plant Reactome:R-OAU-2744343 Amino acid metabolism
Plant Reactome:R-MES-2744345 Metabolism and regulation
Plant Reactome:R-MES-2744343 Amino acid metabolism
Plant Reactome:R-MES-5655124 Amino acid catabolism
Plant Reactome:R-TDI-2744345 Metabolism and regulation
Plant Reactome:R-TDI-2744343 Amino acid metabolism
Plant Reactome:R-DRO-2744345 Metabolism and regulation
Plant Reactome:R-DRO-1119612 Cysteine degradation
Plant Reactome:R-PTI-2744345 Metabolism and regulation
Plant Reactome:R-PTI-2744343 Amino acid metabolism
Plant Reactome:R-PTI-5655124 Amino acid catabolism
Plant Reactome:R-GMA-2744345 Metabolism and regulation
Plant Reactome:R-GMA-2744343 Amino acid metabolism
Plant Reactome:R-PVU-2744345 Metabolism and regulation
Plant Reactome:R-PVU-2744343 Amino acid metabolism
Plant Reactome:R-BRA-1119612 Cysteine degradation
Plant Reactome:R-EGR-5655124 Amino acid catabolism
Plant Reactome:R-LPE-1119612 Cysteine degradation
View All Pathways