Mercaptopyruvate (BioCAD00000013869)
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
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.
DBLinks
- CAS Registry Number: 2464-23-5
- PubChem CID: 98
- ChEBI: 16208
- HMDB: HMDB0001368
- LipidMaps:
- KEGG: C00957
- BioCyc: 3-MERCAPTO-PYRUVATE
- NCBI MeSH: 3-mercaptopyruvic acid
- Wikipedia: 3-Mercaptopyruvic_acid
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
- WishartLab ClassyFire: [Alpha-keto acids and derivatives] Alpha-keto acids and derivatives
- RefMet: [Alpha-keto acids] Alpha-keto acids
- ChEBI: [CHEBI:16208] 3-mercaptopyruvic acid
| 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 |