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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	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xab5fa66c> Close
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	Methyl-branched fatty acids Alpha-keto acids and derivatives Ketones Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Organic anions
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 Ų ChemAxon Rotatable Bond Count 3 ChemAxon Refractivity 42.63 m³·mol⁻¹ ChemAxon Polarizability 12.57 ų 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, 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 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 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