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

Record Information

Version

1.0

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

Value	Source
2-oxo-3-Methyl-N-valeric acid	ChEBI
2-oxo-3-Methylpentanoic acid	ChEBI
2-oxo-3-Methylvalerate	ChEBI
2-oxo-3-Methylvaleric acid	ChEBI
2-Oxoisoleucine	ChEBI
2-Oxokolavenic acid	ChEBI
3-Ethyl-3-methylpyruvic acid	ChEBI
3-Methyl-2-oxopentanoic acid	ChEBI
alpha-Keto-beta-methyl-N-valeric acid	ChEBI
alpha-Keto-beta-methylvaleric acid	ChEBI
alpha-oxo-beta-Methyl-N-valeric acid	ChEBI
alpha-oxo-beta-Methylvaleric acid	ChEBI
Ketoisoleucine	ChEBI
2-oxo-3-Methyl-N-valerate	Generator
2-oxo-3-Methylpentanoate	Generator
2-Oxokolavenate	Generator
3-Ethyl-3-methylpyruvate	Generator
3-Methyl-2-oxopentanoate	Generator
a-Keto-b-methyl-N-valerate	Generator
a-Keto-b-methyl-N-valeric acid	Generator
alpha-Keto-beta-methyl-N-valerate	Generator
Α-keto-β-methyl-N-valerate	Generator
Α-keto-β-methyl-N-valeric acid	Generator
a-Keto-b-methylvalerate	Generator
a-Keto-b-methylvaleric acid	Generator
alpha-Keto-beta-methylvalerate	Generator
Α-keto-β-methylvalerate	Generator
Α-keto-β-methylvaleric acid	Generator
a-oxo-b-Methyl-N-valerate	Generator
a-oxo-b-Methyl-N-valeric acid	Generator
alpha-oxo-beta-Methyl-N-valerate	Generator
Α-oxo-β-methyl-N-valerate	Generator
Α-oxo-β-methyl-N-valeric acid	Generator
a-oxo-b-Methylvalerate	Generator
a-oxo-b-Methylvaleric acid	Generator
alpha-oxo-beta-Methylvalerate	Generator
Α-oxo-β-methylvalerate	Generator
Α-oxo-β-methylvaleric acid	Generator
3-Methyl-2-oxovalerate	Generator
(3R)-3-Methyl-2-oxopentanoate	HMDB
(3R)-3-Methyl-2-oxopentanoic acid	HMDB
(R)-3-Methyl-2-oxopentanoate	HMDB
(R)-3-Methyl-2-oxopentanoic acid	HMDB
(S)-3-Methyl-2-oxopentanoate	HMDB
(S)-3-Methyl-2-oxopentanoic acid	HMDB
2-Keto-3-methylvalerate	HMDB
2-Keto-3-methylvaleric acid	HMDB
3-Methyl-2-oxo-pentanoate	HMDB
3-Methyl-2-oxo-pentanoic acid	HMDB
3-Methyl-2-oxo-valerate	HMDB
3-Methyl-2-oxo-valeric acid	HMDB
3-Methyl-2-oxovaleric	HMDB
2-Keto methylvalerate	HMDB
KMVA	HMDB
alpha-Keto-beta-methylvaleric acid, calcium salt, (S)-isomer	HMDB
alpha-Keto-beta-methylvaleric acid, monosodium salt, (S)-isomer	HMDB
alpha-Keto-beta-methylvaleric acid, (S)-isomer	HMDB
alpha-Keto-beta-methylvaleric acid, calcium salt	HMDB
alpha-Keto-beta-methylvaleric acid, sodium salt, (+-)-isomer	HMDB
alpha-Keto-beta-methylvaleric acid, (+-)-isomer	HMDB
alpha-Keto-beta-methylvaleric acid, sodium salt	HMDB

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

Description

Belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Short-chain keto acids and derivatives

Direct Parent

Short-chain keto acids and derivatives

Alternative Parents

Substituents

Branched fatty acid
Methyl-branched fatty acid
Short-chain keto acid
Alpha-keto acid
Fatty acyl
Alpha-hydroxy ketone
Ketone
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2-oxo monocarboxylic acid (CHEBI:35932 )

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	Data Source	Reference
MMDBr0001504	Oxoglutaric acid	3-Methyl-2-oxovaleric acid	branched chain amino-acid transaminase 2, mitochondrial	VMH; KEGG	30371894
MMDBr0001825	3-Methyl-2-oxovaleric acid	2-Methylbutyryl-CoA	branched chain keto acid dehydrogenase E1, alpha polypeptide	VMH	1429740 2914958
MMDBr0002658	3-Methyl-2-oxovaleric acid	S-(2-Methylbutanoyl)-dihydrolipoamide	branched chain keto acid dehydrogenase E1, alpha polypeptide	VMH	11839747 12387880 15576032
MMDBr0006959	3-Methyl-2-oxovaleric acid	2-Methylbutyryl-CoA	Not Available	VMH	30371894
MMDBr0007468	Oxoglutaric acid	3-Methyl-2-oxovaleric acid	Not Available	VMH; KEGG	30371894
MMDBr0007748	(R)-2,3-Dihydroxy-3-methylpentanoate	3-Methyl-2-oxovaleric acid	Not Available	VMH	30371894
MMDBr0008228	3-Methyl-2-oxovaleric acid	Ethylmethylacetic acid	Not Available	VMH	30371894
MMDBr0008352	3-Methyl-2-oxovaleric acid	2-Methyl-1-hydroxybutyl-ThPP	Not Available	VMH	30371894
MMDBr0008400	L-Isoleucine	3-Methyl-2-oxovaleric acid	Not Available	VMH	30371894
MMDBr0008573	3-Methyl-2-oxovaleric acid	2-Hydroxy-3-methylpentanoic acid	lactate dehydrogenase A	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	Proteobacteria	178	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	Firmicutes	377	Human feces; Human pleural fluid plaque; Pig ; Human ; Human stool; Human subgingival plaque; Cattle	Metabolic reconstruction
Bacteria	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	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	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	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Fusobacteria	11	Human feces; Human	Metabolic reconstruction
Bacteria	Synergistetes	3	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	5		Metabolic reconstruction
Bacteria	Tenericutes	4	Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	4

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Plant		Theobroma cacao	FooDB	31437929

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

HMDB0000491

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021447

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

C03465

BioCyc ID

Not Available

BiGG ID

35662

Wikipedia Link

Not Available

METLIN ID

5478

PubChem Compound

PDB ID

Not Available

ChEBI ID

35932

Food Biomarker Ontology

Not Available

References

Synthesis Reference

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:0x0000559d0532c100>

3D MOL for #<Metabolite:0x0000559d0532c100>

3D SDF for #<Metabolite:0x0000559d0532c100>

3D-SDF for #<Metabolite:0x0000559d0532c100>

PDB for #<Metabolite:0x0000559d0532c100>

3D PDB for #<Metabolite:0x0000559d0532c100>

SMILES for #<Metabolite:0x0000559d0532c100>

INCHI for #<Metabolite:0x0000559d0532c100>

Structure for #<Metabolite:0x0000559d0532c100>

3D Structure for #<Metabolite:0x0000559d0532c100>