ECMDB: 2-Keto-3-methyl-valerate (ECMDB04091) (M2MDB000605)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (2)XML

Proteins (1425)

Record Information

Version

2.0

Creation Date

2012-05-31 14:04:44 -0600

Update Date

2015-06-03 15:54:43 -0600

Secondary Accession Numbers

ECMDB04091

Identification

Name:

2-Keto-3-methyl-valerate

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:

α-keto-β-methyl-valerate
α-keto-β-methyl-valeric acid
α-keto-methylvalerate
α-keto-methylvaleric acid
(3S)-3-Methyl-2-oxopentanoate
(3R)-3-Methyl-2-oxopentanoate
(3R)-3-Methyl-2-oxopentanoic acid
(3S)-3-methyl-2-oxopentanoate
(3S)-3-methyl-2-oxopentanoic acid
(S)-2-oxo-3-methylpentanoate
(S)-3-methyl-2-oxopentanoate
(R)-3-methyl-2-oxopentanoate
(R)-3-methyl-2-oxopentanoic acid
(S)-2-oxo-3-methylpentanoate
(S)-2-oxo-3-methylpentanoic acid
(S)-3-methyl-2-oxopentanoate
(S)-3-methyl-2-oxopentanoic acid
(S)-3-methyl-2-oxovalerate
(S)-3-methyl-2-oxovaleric acid
2-keto-3-methyl-valerate
2-Keto-3-methyl-valeric acid
2-keto-3-methylvalerate
2-keto-3-methylvaleric acid
2-Oxo-3-methyl-N-valerate
2-Oxo-3-methyl-N-valeric acid
2-Oxo-3-methylpentanoate
2-Oxo-3-methylpentanoic acid
2-Oxo-3-methylvalerate
2-Oxo-3-methylvaleric acid
2-Oxoisoleucine
2-Oxokolavenate
2-Oxokolavenic acid
3-Methyl-2-oxo-pentanoate
3-Methyl-2-oxo-pentanoic acid
3-Methyl-2-oxo-Valerate
3-Methyl-2-oxo-Valeric acid
3-Methyl-2-oxopentanoate
3-Methyl-2-oxopentanoic acid
3-Methyl-2-oxovalerate
3-Methyl-2-oxovaleric
3-Methyl-2-oxovaleric acid
A-Keto-b-methyl-N-valerate
A-Keto-b-methyl-N-valeric acid
a-keto-b-Methyl-valerate
a-keto-b-Methyl-valeric acid
A-Keto-b-methylvalerate
A-Keto-b-methylvaleric acid
a-keto-Methylvalerate
a-keto-Methylvaleric acid
A-Oxo-b-methyl-N-valerate
A-Oxo-b-methyl-N-valeric acid
A-Oxo-b-methylvalerate
A-Oxo-b-methylvaleric acid
Alpha-Keto-beta-methyl-N-valerate
Alpha-Keto-beta-methyl-N-valeric acid
Alpha-Keto-beta-methyl-valerate
Alpha-Keto-beta-methyl-valeric acid
Alpha-Keto-beta-methylvalerate
Alpha-Keto-beta-methylvaleric acid
Alpha-Keto-methylvalerate
Alpha-Keto-methylvaleric acid
Alpha-Oxo-beta-methyl-N-valerate
Alpha-Oxo-beta-methyl-N-valeric acid
Alpha-Oxo-beta-methylvalerate
Alpha-Oxo-beta-methylvaleric acid
α-keto-Methylvalerate
α-keto-Methylvaleric acid
α-keto-β-Methyl-N-valerate
α-keto-β-Methyl-N-valeric acid
α-keto-β-Methyl-valerate
α-keto-β-Methyl-valeric acid
α-keto-β-Methylvalerate
α-keto-β-Methylvaleric acid
α-oxo-β-Methyl-N-valerate
α-oxo-β-Methyl-N-valeric acid
α-oxo-β-Methylvalerate
α-oxo-β-Methylvaleric acid

Chemical Formula:

C₆H₉O₃

Weight:

Average: 129.1339
Monoisotopic: 129.055169154

InChI Key:

JVQYSWDUAOAHFM-BYPYZUCNSA-M

InChI:

InChI=1S/C6H10O3/c1-3-4(2)5(7)6(8)9/h4H,3H2,1-2H3,(H,8,9)/p-1/t4-/m0/s1

CAS number:

1460-34-0

IUPAC Name:

(3S)-3-methyl-2-oxopentanoate

Traditional IUPAC Name:

(S)-3-methyl-2-oxopentanoate

SMILES:

CC[C@H](C)C(=O)C([O-])=O

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

3-methyl-2-oxovalerate (CHEBI:35146 )

Physical Properties

State:

Solid

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	12.5 g/L	ALOGPS
logP	0.9	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	0	ChemAxon
Polar Surface Area	57.2 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	42.63 m³·mol⁻¹	ChemAxon
Polarizability	12.57 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

SMPDB Pathways:

isoleucine biosynthesis

PW000818

KEGG Pathways:

Valine, leucine and isoleucine biosynthesis ec00290
Valine, leucine and isoleucine degradation ec00280

EcoCyc Pathways:

isoleucine biosynthesis I (from threonine) ILEUSYN-PWY

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004r-5900000000-b6e4bf6b61d36f9fd8f2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002r-9400000000-6c5640ec288bdaaf640c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-6712db6d9ef51bd9e424	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-3900000000-5620b4eae30516174873	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9200000000-d9053af6ae24b52d5826	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-db79bf299009a6887756	View in MoNA
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	35146
HMDB ID	HMDB00491
Pubchem Compound ID	6857401
Kegg ID	C00671
ChemSpider ID	19951083
Wikipedia ID	Not Available
BioCyc ID	2-KETO-3-METHYL-VALERATE
EcoCyc ID	2-KETO-3-METHYL-VALERATE

Enzymes

Protein Details

1. Dihydroxy-acid dehydratase

General function:: Involved in metabolic process
Specific function:: 2,3-dihydroxy-3-methylbutanoate = 3-methyl-2- oxobutanoate + H(2)O
Gene Name:: ilvD
Uniprot ID:: P05791
Molecular weight:: 65531

Reactions

2,3-dihydroxy-3-methylbutanoate = 3-methyl-2-oxobutanoate + H(2)O.

Protein Details

2. Branched-chain-amino-acid aminotransferase

General function:: Involved in catalytic activity
Specific function:: Acts on leucine, isoleucine and valine
Gene Name:: ilvE
Uniprot ID:: P0AB80
Molecular weight:: 34093

Reactions

L-leucine + 2-oxoglutarate = 4-methyl-2-oxopentanoate + L-glutamate.
L-isoleucine + 2-oxoglutarate = (S)-3-methyl-2-oxopentanoate + L-glutamate.
L-valine + 2-oxoglutarate = 3-methyl-2-oxobutanoate + L-glutamate.

2-Keto-3-methyl-valerate (ECMDB04091) (M2MDB000605)

Structure for #<Compound:0x598f058>

Enzymes

Reactions

Reactions