MiMeDB: Showing metabocard for 3-Methyl-2-oxovaleric acid (MMDBc0029497)

Microbial

Plant

Xenobiotic

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:24:41 UTC

Update Date

2024-10-09 18:50:30 UTC

Metabolite ID

MMDBc0029497

Metabolite Identification

Common Name

3-Methyl-2-oxovaleric acid

Description

3-Methyl-2-oxovaleric acid is a metabolite of isoleucine in man, animals and bacteria. It is the alpha-keto acid analogue of isoleucine. 3-Methyl-2-oxovaleric acid is produced from isoleucine by cytosolic branched chain aminotransferase 1 (EC:2.6.1.42), whereupon it is further degraded by branched chain keto acid dehydrogenase E1 to 2-Methyl-1-hydroxybutyl-ThPP.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Molecular Formula

C₆H₁₀O₃

Average Mass

130.1418

Monoisotopic Mass

130.062994186

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

1460-34-0

SMILES

Not Available

InChI Identifier

InChI=1S/C6H10O3/c1-3-4(2)5(7)6(8)9/h4H,3H2,1-2H3,(H,8,9)

InChI Key

JVQYSWDUAOAHFM-UHFFFAOYSA-N

Chemical Taxonomy

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Not Available

Spectra

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-23	276.4
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	36.5
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	364.5
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	518.5
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	454.4
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-23	415.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	1588.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	118.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	590.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	388.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	331.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	259.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	132.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	86.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	465.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	103.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	341.8
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	1191.0
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	907.7

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	3-Methyl-2-oxovaleric acid_TMS_1	CCC(C)C(=O)C(=O)O[Si](C)(C)C	standard non polar	2025-10-23	2119.67
Gas Chromatography	3-Methyl-2-oxovaleric acid_TMS_2	CCC(C)=C(O[Si](C)(C)C)C(=O)O	standard non polar	2025-10-23	2372.3
Gas Chromatography	3-Methyl-2-oxovaleric acid_TMS_3	CCC(C)=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-23	2383.45
Gas Chromatography	3-Methyl-2-oxovaleric acid_TMS_1	CCC(C)C(=O)C(=O)O[Si](C)(C)C	standard polar	2025-10-23	2097.91
Gas Chromatography	3-Methyl-2-oxovaleric acid_TMS_2	CCC(C)=C(O[Si](C)(C)C)C(=O)O	standard polar	2025-10-23	2046.11
Gas Chromatography	3-Methyl-2-oxovaleric acid_TMS_3	CCC(C)=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard polar	2025-10-23	2136.71

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

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0018262	3-Methyl-2-oxovaleric acid	2-Isopropylmalic acid	2-isopropylmalate synthase	Synthesis	PathBank	31602464
MMDBr0018305	(R) 2,3-Dihydroxy-3-methylvalerate	3-Methyl-2-oxovaleric acid	Dihydroxy-acid dehydratase	Hydration/dehydration of C-O bond	PathBank	31602464
MMDBr0018306	L-Glutamic acid	L-Isoleucine	Branched-chain-amino-acid aminotransferase	Amine group addition	PathBank	31602464
MMDBr0018673	L-Glutamic acid	Oxoglutaric acid	Branched-chain-amino-acid aminotransferase	Amine group addition	PathBank	31602464
MMDBr0019817	3-Methyl-2-oxovaleric acid	2-Isopropylmalic acid	Unknown Protein		PathBank	31602464
MMDBr0019825	(R) 2,3-Dihydroxy-3-methylvalerate	3-Methyl-2-oxovaleric acid	Dihydroxy-acid dehydratase, mitochondrial	Hydration/dehydration of C-O bond	PathBank	31602464
MMDBr0019826	L-Glutamic acid	L-Isoleucine	Unknown Protein		PathBank	31602464
MMDBr0026147	3-Methyl-2-oxovaleric acid	L-Isoleucine	Ornithine aminotransferase	Amine group addition	RHEA	34755880

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	Proteobacteria	1	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	Unknown; Metabolic reconstruction
Bacteria/Eubacteria	Firmicutes	377	Human feces; Human pleural fluid plaque; Pig ; Human ; Human stool; Human subgingival plaque; Cattle	Metabolic reconstruction
Bacteria/Eubacteria	Proteobacteria	177	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	Unknown; Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	119	Human feces; Human pleural fluid plaque; Human dental plaque; Human sputum; Human ; Human nasopharyngeal swab; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria/Eubacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Bacteroidetes	116	Human feces; Human appendix biopsy; Human ; Human gastric fluid; Human saliva; Human subgingival plaque; Human supragingival plaque; Human stool; Human urine	Metabolic reconstruction
Bacteria/Eubacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria/Eubacteria	Fusobacteria	11	Human feces; Human	Metabolic reconstruction
Bacteria/Eubacteria	Synergistetes	2	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	5		Metabolic reconstruction
Bacteria/Eubacteria	Tenericutes	4	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Bacteria	Synergistetes	1	Human feces	Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	4

Exposure Sources

Other Exposures

Source Type	Data Source	Reference
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox

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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Hutson SM, Hall TR: Identification of the mitochondrial branched chain aminotransferase as a branched chain alpha-keto acid transport protein. J Biol Chem. 1993 Feb 15;268(5):3084-91. [PubMed:8428987 ]
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 ]
Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]

Showing metabocard for 3-Methyl-2-oxovaleric acid (MMDBc0029497)

MOL for #<Metabolite:0x00007fae02045c10>

3D MOL for #<Metabolite:0x00007fae02045c10>

3D SDF for #<Metabolite:0x00007fae02045c10>

3D-SDF for #<Metabolite:0x00007fae02045c10>

PDB for #<Metabolite:0x00007fae02045c10>

3D PDB for #<Metabolite:0x00007fae02045c10>

SMILES for #<Metabolite:0x00007fae02045c10>

INCHI for #<Metabolite:0x00007fae02045c10>

Structure for #<Metabolite:0x00007fae02045c10>

3D Structure for #<Metabolite:0x00007fae02045c10>