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

2022-08-31 10:32:46 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

3-methyl-2-oxopentanoic acid

Traditional Name

3-methyl-2-oxopentanoic acid

CAS Registry Number

1460-34-0

SMILES

CCC(C)C(=O)C(O)=O

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

Property	Value	Source
Water Solubility	9.86 g/L	ALOGPS
logP	1	ALOGPS
logP	1.75	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	3.52	ChemAxon
pKa (Strongest Basic)	-9.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	31.79 m³·mol⁻¹	ChemAxon
Polarizability	13.09 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-000i-9610000000-d2ffd4c2796688c555ee	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-000i-9720000000-9cbc934e100bedd87f17	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-000i-9720000000-5acbdc73aee24c023763	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-000i-6930000000-8c2cf1d8df538010611b	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-6930000000-7bef6751c4c607393e5e	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0hg9-4950000000-3e1c700a6f553bf63afb	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000i-9610000000-d2ffd4c2796688c555ee	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000i-9720000000-9cbc934e100bedd87f17	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000i-9720000000-5acbdc73aee24c023763	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000i-6930000000-8c2cf1d8df538010611b	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-056r-9000000000-d08073312b337cdae9e6	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-05bo-9400000000-9937bff65302162dc3b9	2017-10-06	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000w-9300000000-0a6ff60455403c38be39	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0002-9000000000-7ee6d2fb63c6ea4cccfa	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-002b-9000000000-47d18dff23b741029581	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-004i-0900000000-ae9da2a9acfa56fc6091	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-004r-5900000000-a3f740a5c859439255be	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-06sr-7900000000-4920c1aefcca814ec1f6	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4r-9100000000-16995fa8eb603d828a2f	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-a6ccc899039a438533ae	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004r-5900000000-50107933abbe9c175553	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ri-9700000000-23998218af9ee2898594	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-a30461e2df45eeb8f795	2017-09-01	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

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

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0000075	3-Methyl-2-oxovaleric acid	3-Methyl-2-oxovaleric acid	Not Available	3-Methyl-2-Oxopentanoate Mitochondrial Transport via Proton Symport	VMH	8428987
MMDBr0001504	Oxoglutaric acid	3-Methyl-2-oxovaleric acid	Branched chain amino-acid transaminase 2, mitochondrial	Isoleucine Transaminase, Mitochondrial	VMH	30371894
MMDBr0001825	3-Methyl-2-oxovaleric acid	2-Methylbutyryl-CoA	Branched chain keto acid dehydrogenase e1, alpha polypeptide	2-Oxoisovalerate Dehydrogenase (Acylating	VMH	1429740 2914958
MMDBr0002658	3-Methyl-2-oxovaleric acid	Carbon dioxide	Branched chain keto acid dehydrogenase e1, alpha polypeptide	(S)-3-Methyl-2-Oxopentanoate:[Dihydrolipoyllysine-Residue (2-Methylpropanoyl)Transferase] Lipoyllysine 2-Oxidoreductase (Decarboxylating, Acceptor-2-Methylpropanoylating)	VMH	11839747 12387880 15576032
MMDBr0005532	3-Methyl-2-oxovaleric acid	3-Methyl-2-oxovaleric acid	Not Available	Transport of 3-Methyl-2-Oxopentanoate	VMH	30371894
MMDBr0006959	3-Methyl-2-oxovaleric acid	2-Methylbutyryl-CoA	Not Available	2-oxoisovalerate dehydrogenase (acylating; 3-methyl-2-oxopentanoate)	VMH	30371894
MMDBr0007468	Oxoglutaric acid	3-Methyl-2-oxovaleric acid	Not Available	Isoleucine Transaminase	VMH	30371894
MMDBr0007748	(R)-2,3-Dihydroxy-3-methylpentanoate	3-Methyl-2-oxovaleric acid	Not Available	Dihydroxy-acid dehydratase (2,3-dihydroxy-3-methylpentanoate)	VMH	30371894
MMDBr0008228	3-Methyl-2-oxovaleric acid	Ethylmethylacetic acid	Not Available	L-isoleucine Stickland reaction, second step	VMH	30371894
MMDBr0008352	3-Methyl-2-oxovaleric acid	2-Methyl-1-hydroxybutyl-ThPP	Not Available	3 methyl 2 oxopentanoate decarboxylase	VMH	30371894
MMDBr0008400	Water	3-Methyl-2-oxovaleric acid	Not Available	Ile-L[c]:nad[c]+ oxidoreductase(deaminating)	VMH	30371894
MMDBr0008439	3-Methyl-2-oxovaleric acid	3-Methyl-2-oxovaleric acid	Not Available	3-Methyl-2-oxopentanoate transport via proton symport reversible	VMH	30371894
MMDBr0008573	3-Methyl-2-oxovaleric acid	2-Hydroxy-3-methylpentanoic acid	Lactate dehydrogenase a	Formation of 2-Hydroxy-3-Methyl-Valerate	VMH	30371894
MMDBr0018262	3-Methyl-2-oxovaleric acid	Hydrogen Ion	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	Hydrogen Ion	Not Available		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	Not Available		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	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:0x00007f5a943af638>

3D MOL for #<Metabolite:0x00007f5a943af638>

3D SDF for #<Metabolite:0x00007f5a943af638>

3D-SDF for #<Metabolite:0x00007f5a943af638>

PDB for #<Metabolite:0x00007f5a943af638>

3D PDB for #<Metabolite:0x00007f5a943af638>

SMILES for #<Metabolite:0x00007f5a943af638>

INCHI for #<Metabolite:0x00007f5a943af638>

Structure for #<Metabolite:0x00007f5a943af638>

3D Structure for #<Metabolite:0x00007f5a943af638>