MiMeDB: Showing metabocard for 3-Carboxy-4-methyl-2-oxopentanoate (MMDBc0049885)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-04-29 22:45:32 UTC

Update Date

2025-01-15 22:46:44 UTC

Metabolite ID

MMDBc0049885

Metabolite Identification

Common Name

3-Carboxy-4-methyl-2-oxopentanoate

Description

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).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Molecular Formula

C₇H₁₀O₅

Average Mass

174.1513

Monoisotopic Mass

174.05282343

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

InChI Identifier

InChI=1S/C7H10O5/c1-3(2)4(6(9)10)5(8)7(11)12/h3-4H,1-2H3,(H,9,10)(H,11,12)/t4-/m0/s1

InChI Key

HIIZAGQWABAMRR-BYPYZUCNSA-N

Chemical Taxonomy

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0007074	3-Carboxy-2-hydroxy-4-methylpentanoate	3-Carboxy-4-methyl-2-oxopentanoate	Not Available		VMH	30371894
MMDBr0008123	3-Carboxy-4-methyl-2-oxopentanoate	Ketoleucine	Not Available		VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Firmicutes	288	Human feces; Human pleural fluid plaque; Pig ; Human ; Human supragingival plaque; Human saliva; Human stool; Human subgingival plaque	Metabolic reconstruction
Bacteria/Eubacteria	Proteobacteria	168	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal	Metabolic reconstruction
Bacteria	Actinobacteria	14	Human feces; Human pleural fluid plaque; Human dental plaque; Human sputum; Human ; Human supragingival plaque; Human mucosa; Human subgingival plaque	Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	103	Human feces; Human pleural fluid plaque; Human dental plaque; Human sputum; Human ; Human supragingival plaque; Human mucosa; Human subgingival plaque	Metabolic reconstruction
Bacteria/Eubacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Bacteroidetes	92	Human feces; Human appendix biopsy; Human ; Human stool; Human urine; Human gastric fluid; Human saliva	Metabolic reconstruction
Bacteria/Eubacteria	Synergistetes	3	Human feces	Metabolic reconstruction
Bacteria	Proteobacteria	7	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal	Metabolic reconstruction
Bacteria/Eubacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Firmicutes	25	Human feces; Human pleural fluid plaque; Pig ; Human ; Human supragingival plaque; Human saliva; Human stool; Human subgingival plaque	Metabolic reconstruction
Bacteria/Eubacteria	Fusobacteria	14	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	4		Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1		Metabolic reconstruction
Bacteria/Eubacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Bacteria	Synergistetes	1	Human feces	Metabolic reconstruction

Exposure Sources

Source Type	Activity	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

Not Available

References

Synthesis Reference

Not Available

General References

Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]

Showing metabocard for 3-Carboxy-4-methyl-2-oxopentanoate (MMDBc0049885)

MOL for #<Metabolite:0x00007f3e0d83ab60>

3D MOL for #<Metabolite:0x00007f3e0d83ab60>

3D SDF for #<Metabolite:0x00007f3e0d83ab60>

3D-SDF for #<Metabolite:0x00007f3e0d83ab60>

PDB for #<Metabolite:0x00007f3e0d83ab60>

3D PDB for #<Metabolite:0x00007f3e0d83ab60>

SMILES for #<Metabolite:0x00007f3e0d83ab60>

INCHI for #<Metabolite:0x00007f3e0d83ab60>

Structure for #<Metabolite:0x00007f3e0d83ab60>

3D Structure for #<Metabolite:0x00007f3e0d83ab60>