| Record Information |
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| Version | 2.0 |
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| Creation Date | 2012-05-31 09:55:11 -0600 |
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| Update Date | 2015-06-03 15:00:41 -0600 |
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| Secondary Accession Numbers | |
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| Identification |
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| Name: | 2-Ketobutyric acid |
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| Description | 2-Ketobutyric acid (alpha ketobutyric acid) is involved in the metabolism of many amino acids (glycine, cysteine, methionine, valine, leucine, serine, threonine, isoleucine). It also plays a role in propanoate metabolism and C-5 branched dibasic acid metabolism. More specifically, alpha-ketobutyric acid can be produced through the lysis of cystathionine (via cystathionine gamma lyase) leading to the production of cysteine and alpha-ketobutyric acid. It is also one of the degradation products of threonine. It can be converted to propionyl-CoA (and subsequently methylmalonyl CoA, which can be converted to succinyl CoA, a citric acid cycle intermediate), and thus enter the citric acid cycle. |
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| Structure | |
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| Synonyms: | - α-ketobutyrate
- α-ketobutyric acid
- α-oxobutyrate
- α-oxobutyric acid
- 2-Keto-butyrate
- 2-Keto-butyric acid
- 2-Ketobutanoate
- 2-Ketobutanoic acid
- 2-Ketobutyrate
- 2-Ketobutyric acid
- 2-OBA
- 2-Oxo-Butanoate
- 2-Oxo-Butanoic acid
- 2-Oxo-Butyrate
- 2-Oxo-Butyric acid
- 2-Oxo-N-butyrate
- 2-Oxo-N-butyric acid
- 2-Oxobutanoate
- 2-Oxobutanoic acid
- 2-Oxobutyrate
- 2-Oxobutyric acid
- 3-Methylpyruvate
- 3-Methylpyruvic acid
- A-Keto-N-Butyrate
- A-Keto-N-Butyric acid
- a-Ketobutrate
- a-Ketobutric acid
- A-Ketobutyrate
- A-Ketobutyric acid
- A-Oxo-N-butyrate
- A-Oxo-N-butyric acid
- A-Oxobutyrate
- A-Oxobutyric acid
- Alpha-Keto-N-butyrate
- Alpha-Keto-N-butyric acid
- Alpha-Ketobutrate
- Alpha-Ketobutric acid
- Alpha-Ketobutyrate
- Alpha-Ketobutyric acid
- Alpha-Oxo-N-butyrate
- Alpha-Oxo-N-butyric acid
- Alpha-Oxobutyrate
- Alpha-Oxobutyric acid
- Methyl-Pyruvate
- Methyl-Pyruvic acid
- Propionyl-formate
- Propionyl-formic acid
- α-keto-N-Butyrate
- α-keto-N-Butyric acid
- α-Ketobutrate
- α-Ketobutric acid
- α-Ketobutyrate
- α-Ketobutyric acid
- α-oxo-N-Butyrate
- α-oxo-N-Butyric acid
- α-Oxobutyrate
- α-Oxobutyric acid
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| Chemical Formula: | C4H6O3 |
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| Weight: | Average: 102.0886
Monoisotopic: 102.031694058 |
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| InChI Key: | TYEYBOSBBBHJIV-UHFFFAOYSA-N |
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| InChI: | InChI=1S/C4H6O3/c1-2-3(5)4(6)7/h2H2,1H3,(H,6,7) |
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| CAS number: | 600-18-0 |
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| IUPAC Name: | (1S,2R,3R,7S,7aR)-3-(hydroxymethyl)-hexahydro-1H-pyrrolizine-1,2,7-triol |
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| Traditional IUPAC Name: | (1S,2R,3R,7S,7aR)-3-(hydroxymethyl)-hexahydro-1H-pyrrolizine-1,2,7-triol |
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| SMILES: | CCC(=O)C(O)=O |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as pyrrolizidines. Pyrrolizidines are compounds containing a pyrrolizidine, which is a bicyclic ring system made up of two fused pyrrolidine ring sharing a nitrogen atom. |
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| Kingdom | Organic compounds |
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| Super Class | Organoheterocyclic compounds |
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| Class | Pyrrolizidines |
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| Sub Class | Not Available |
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| Direct Parent | Pyrrolizidines |
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| Alternative Parents | |
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| Substituents | - Pyrrolizidine
- N-alkylpyrrolidine
- Pyrrolidine
- Secondary alcohol
- Tertiary amine
- Tertiary aliphatic amine
- 1,2-aminoalcohol
- Polyol
- Azacycle
- Alcohol
- Organic oxygen compound
- Organic nitrogen compound
- Organopnictogen compound
- Primary alcohol
- Organooxygen compound
- Organonitrogen compound
- Amine
- Hydrocarbon derivative
- Aliphatic heteropolycyclic compound
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| Molecular Framework | Aliphatic heteropolycyclic compounds |
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| External Descriptors | Not Available |
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| Physical Properties |
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| State: | Solid |
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| Charge: | 1 |
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| Melting point: | 33°C [Suante, H.; Oxidation Communications 2004, V27(2), P344-348] |
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| Experimental Properties: | | Property | Value | Source |
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| Water Solubility: | 119 mg/mL [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: | |
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| KEGG Pathways: | - C5-Branched dibasic acid metabolism ec00660
- Cysteine and methionine metabolism ec00270
- Glycine, serine and threonine metabolism ec00260
- Metabolic pathways eco01100
- Propanoate metabolism ec00640
- Valine, leucine and isoleucine biosynthesis ec00290
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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: | |
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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
- Sprague CL, Elfarra AA: Detection of carboxylic acids and inhibition of hippuric acid formation in rats treated with 3-butene-1,2-diol, a major metabolite of 1,3-butadiene. Drug Metab Dispos. 2003 Aug;31(8):986-92. Pubmed: 12867486
- 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
- Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
- Yaegaki K, Sanada K: Biochemical and clinical factors influencing oral malodor in periodontal patients. J Periodontol. 1992 Sep;63(9):783-9. Pubmed: 1474480
- Yaegaki K, Sanada K: Effects of a two-phase oil-water mouthwash on halitosis. Clin Prev Dent. 1992 Jan-Feb;14(1):5-9. Pubmed: 1499240
- Yang W, Roth KS: Defect in alpha-ketobutyrate metabolism: a new inborn error. Clin Chim Acta. 1985 Jan 30;145(2):173-82. Pubmed: 3918815
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| Synthesis Reference: | Figge, Rainer; Lux, Fabien; Raynaud, Celine; Soucaille, Philippe. Production of a-ketobutyrate by engineered Escherichia coli.PCT Int. Appl. (2006), 31pp. |
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| Material Safety Data Sheet (MSDS) | Not Available |
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| Links |
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| External Links: | |
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