(2S)-2-Isopropyl-3-oxosuccinate (BioCAD00000000462)
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Metabolite Card
Formula: C7H10O5 (174.0528)
SMILES: CC(C)[C@H](C(O)=O)C(=O)C(O)=O
Synonyms [en]
(2S)-2-Isopropyl-3-oxosuccinate; 3-Carboxy-4-methyl-2-oxopentanoate; (2S)-2-isopropyl-3-oxosuccinic acid; 2-Oxo-4-methyl-3-carboxypentanoate; (2S)-2-(1-methylethyl)-3-oxobutanedioic acid; 3-Carboxy-4-methyl-2-oxopentanoic acid
Last reviewed on 2024-06-28.
Cite this Page
(2S)-2-Isopropyl-3-oxosuccinate. 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: BioCAD00000000462). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Note
2-Isopropyl-3-oxosuccinate belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain that contains less than 6 carbon atoms. 2-Isopropyl-3-oxosuccinate is an extremely weak basic (essentially neutral) compound (based on its pKa). 2-Isopropyl-3-oxosuccinate exists in all living species, ranging from bacteria to humans. 2-Isopropyl-3-oxosuccinate has been detected, but not quantified in, several different foods, such as garden onion (var.), German camomiles, limes, cloud ear fungus, and citrus. This could make 2-isopropyl-3-oxosuccinate a potential biomarker for the consumption of these foods. 2-Isopropyl-3-oxosuccinate is an intermediate in leucine biosynthesis and can be generated from (2R,3S)-3-isopropylmalate. It is the third step in leucine biosynthesis after the fork from valine synthesis. It is an oxidative decarboxylation. Leucine biosynthesis involves a five-step conversion process starting with the valine precursor 2-keto-isovalerate. The final step in this pathway is catalyzed by two transaminases of broad specificity: branched-chain amino acid transferase (IlvE) and tyrosine aminotransferase (TyrB). In this pathway, 2-isopropyl-3-oxosuccinate is converted into 4-methyl-2-oxopentanoate via a spontaneous reaction (BioCyc).
DBLinks
- CAS Registry Number: 1245945-28-1
- PubChem CID: 5462259
- ChEBI: 1467
- HMDB: HMDB0012149
- LipidMaps:
- KEGG: C04236
- BioCyc:
- NCBI MeSH:
- Wikipedia:
Other DBLinks
- CAS Registry Number: 1245945-28-1
- PubChem: 5462259
- ChEBI: ChEBI:1467
- HMDB: HMDB0012149
- KEGG: C04236
- RefMet: RM0136364
- Metlin: METLIN_3301
- Coconut NaturalProduct: CNP0409700.1
Class / Ontology
- WishartLab ClassyFire: [Short-chain keto acids and derivatives] Short-chain keto acids and derivatives
- RefMet: [Beta-keto acids] Beta-keto acids
- ChEBI: [CHEBI:1467] (2S)-2-isopropyl-3-oxosuccinic acid
- Coconut NaturalProduct: [Dicarboxylic acids] Dicarboxylic acids
| ID | EC Number | Name |
|---|---|---|
| KEGG:R01652 | 1.1.1.85 | C00233 + C00011<=>C04236 |
| KEGG:R04426 | 1.1.1.85 | (2R,3S)-3-isopropylmalate:NAD+ oxidoreductase |
Taxonomy Source
Pathway Synthetic
| pathway id | name |
|---|---|
| PathBank:SMP0000831 | Leucine Biosynthesis |
| PathBank:SMP0000994 | Secondary Metabolites: Valine and L-Leucine Biosynthesis from Pyruvate |
| PathBank:SMP0000996 | Secondary Metabolites: Leucine Biosynthesis |
| PathBank:SMP0121332 | Secondary Metabolites: Leucine Biosynthesis |
| PathBank:SMP0121287 | Leucine Biosynthesis |
| PathBank:SMP0121331 | Secondary Metabolites: Valine and L-Leucine Biosynthesis from Pyruvate |
| PathBank:SMP0002432 | Leucine Biosynthesis |
| PathBank:SMP0002374 | Leucine Biosynthesis |