Record Information |
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Version | 2.0 |
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Creation Date | 2012-05-31 10:26:56 -0600 |
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Update Date | 2015-09-13 12:56:08 -0600 |
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Secondary Accession Numbers | |
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Identification |
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Name: | 3-Methyl-2-oxovaleric acid |
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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. |
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Structure | |
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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
- 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
- 2K3MVA
- 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
- 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
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Chemical Formula: | C6H10O3 |
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Weight: | Average: 130.1418 Monoisotopic: 130.062994186 |
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InChI Key: | JVQYSWDUAOAHFM-UHFFFAOYSA-N |
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InChI: | InChI=1S/C6H10O3/c1-3-4(2)5(7)6(8)9/h4H,3H2,1-2H3,(H,8,9) |
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CAS number: | 1460-34-0 |
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IUPAC Name: | 3-methyl-2-oxopentanoic acid |
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Traditional IUPAC Name: | 3-methyl-2-oxopentanoic acid |
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SMILES: | CCC(C)C(=O)C(O)=O |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Keto acids and derivatives |
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Sub Class | Short-chain keto acids and derivatives |
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Direct Parent | Short-chain keto acids and derivatives |
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Alternative Parents | |
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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
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Physical Properties |
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State: | Solid |
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Charge: | -1 |
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Melting point: | Not Available |
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Experimental Properties: | Property | Value | Source |
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Water Solubility: | 915.5 mg/mL [sodium salt, HMP experimental] | PhysProp |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations: | Cytoplasm |
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Reactions: | |
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SMPDB Pathways: | Leucine Biosynthesis | PW000811 | | Secondary Metabolite: Leucine biosynthesis | PW000980 | | Secondary Metabolites: Valine and I-leucine biosynthesis from pyruvate | PW000978 | | isoleucine biosynthesis | PW000818 | |
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KEGG Pathways: | - Valine, leucine and isoleucine biosynthesis ec00290
- Valine, leucine and isoleucine degradation ec00280
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EcoCyc Pathways: | |
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Concentrations |
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| Not Available |
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Spectra |
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Spectra: | Spectrum Type | Description | Splash Key | |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS) | splash10-000i-9610000000-d2ffd4c2796688c555ee | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS) | splash10-000i-9720000000-9cbc934e100bedd87f17 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-000i-9720000000-5acbdc73aee24c023763 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-000i-6930000000-8c2cf1d8df538010611b | View in MoNA |
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GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-000i-6930000000-7bef6751c4c607393e5e | View in MoNA |
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GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0hg9-4950000000-3e1c700a6f553bf63afb | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-000i-9610000000-d2ffd4c2796688c555ee | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-000i-9720000000-9cbc934e100bedd87f17 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-000i-9720000000-5acbdc73aee24c023763 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-000i-6930000000-8c2cf1d8df538010611b | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-056r-9000000000-d08073312b337cdae9e6 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-05bo-9400000000-9937bff65302162dc3b9 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-000w-9300000000-0a6ff60455403c38be39 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0002-9000000000-7ee6d2fb63c6ea4cccfa | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-002b-9000000000-47d18dff23b741029581 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-004i-0900000000-ae9da2a9acfa56fc6091 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-IT , negative | splash10-004r-5900000000-a3f740a5c859439255be | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-06sr-7900000000-4920c1aefcca814ec1f6 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4r-9100000000-16995fa8eb603d828a2f | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-9000000000-a6ccc899039a438533ae | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004r-5900000000-50107933abbe9c175553 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-01ri-9700000000-23998218af9ee2898594 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-9000000000-a30461e2df45eeb8f795 | View in MoNA |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | View in JSpectraViewer |
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References |
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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
- Przyrembel H, Bremer HJ, Duran M, Bruinvis L, Ketting D, Wadman SK, Baumgartner R, Irle U, Bachmann C: Propionyl-CoA carboxylase deficiency with overflow of metabolites of isoleucine catabolism at all levels. Eur J Pediatr. 1979 Jan 18;130(1):1-14. Pubmed: 759179
- Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
- Wendel U, Even G, Langenbeck U, Schadewaldt P, Hummel W: Determination of (S)- and (R)-2-oxo-3-methylvaleric acid in plasma of patients with maple syrup urine disease. Clin Chim Acta. 1992 Jun 15;208(1-2):85-91. Pubmed: 1638756
- Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A
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Synthesis Reference: | Kondo, Shigeo; Sudo, Tetsuji; Ogiwara, Mitsuo; Takeuchi, Hiroshi. a-Oxo-b-methyl-n-valeric acid and its salts. Jpn. Kokai Tokkyo Koho (1979), 3 pp. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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Links |
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External Links: | |
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