(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

Reviewed

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).

Entity Information

DBLinks

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

Metabolic Network
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
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Organism Source

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
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