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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2020-10-09 20:57:01 UTC |
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HMDB ID | HMDB0000019 |
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Secondary Accession Numbers | - HMDB00019
- HMDB0004260
- HMDB04260
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Metabolite Identification |
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Common Name | alpha-Ketoisovaleric acid |
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Description | alpha-Ketoisovaleric acid is an abnormal metabolite that arises from the incomplete breakdown of branched-chain amino acids. alpha-Ketoisovaleric acid is a neurotoxin, an acidogen, and a metabotoxin. A neurotoxin causes damage to nerve cells and nerve tissues. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of alpha-ketoisovaleric acid are associated with maple syrup urine disease. MSUD is a metabolic disorder caused by a deficiency of the branched-chain alpha-keto acid dehydrogenase complex (BCKDC), leading to a buildup of the branched-chain amino acids (leucine, isoleucine, and valine) and their toxic by-products (ketoacids) in the blood and urine. The symptoms of MSUD often show in infancy and lead to severe brain damage if untreated. MSUD may also present later depending on the severity of the disease. If left untreated in older individuals, during times of metabolic crisis, symptoms of the condition include uncharacteristically inappropriate, extreme, or erratic behaviour and moods, hallucinations, anorexia, weight loss, anemia, diarrhea, vomiting, dehydration, lethargy, oscillating hypertonia and hypotonia, ataxia, seizures, hypoglycemia, ketoacidosis, opisthotonus, pancreatitis, rapid neurological decline, and coma. In maple syrup urine disease, the brain concentration of branched-chain ketoacids can increase 10- to 20-fold. This leads to a depletion of glutamate and a consequent reduction in the concentration of brain glutamine, aspartate, alanine, and other amino acids. The result is a compromise of energy metabolism because of a failure of the malate-aspartate shuttle and a diminished rate of protein synthesis (PMID: 15930465 ). alpha-Ketoisovaleric acid is a keto-acid, which is a subclass of organic acids. Abnormally high levels of organic acids in the blood (organic acidemia), urine (organic aciduria), the brain, and other tissues lead to general metabolic acidosis. Acidosis typically occurs when arterial pH falls below 7.35. In infants with acidosis, the initial symptoms include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy). These can progress to heart, liver, and kidney abnormalities, seizures, coma, and possibly death. These are also the characteristic symptoms of untreated MSUD. Many affected children with organic acidemias experience intellectual disability or delayed development. |
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Structure | |
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Synonyms | Value | Source |
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2-Keto-3-methylbutyric acid | ChEBI | 2-Ketoisovaleric acid | ChEBI | 2-Ketovaline | ChEBI | 2-oxo-3-Methylbutanoic acid | ChEBI | 2-oxo-3-Methylbutyric acid | ChEBI | 2-Oxoisovaleric acid | ChEBI | 3-Methyl-2-oxobutanoate | ChEBI | 3-Methyl-2-oxobutyric acid | ChEBI | alpha-Keto-isovaleric acid | ChEBI | alpha-Ketovaline | ChEBI | alpha-oxo-beta-Methylbutyricacid | ChEBI | alpha-Oxoisovaleric acid | ChEBI | Dimethylpyruvic acid | ChEBI | Isopropylglyoxylic acid | ChEBI | 2-oxo-3-Methylbutanoate | Kegg | 2-Oxoisovalerate | Kegg | 2-Oxoisopentanoate | Kegg | 2-Keto-3-methylbutyrate | Generator | 2-Ketoisovalerate | Generator | 2-oxo-3-Methylbutyrate | Generator | 3-Methyl-2-oxobutanoic acid | Generator | 3-Methyl-2-oxobutyrate | Generator | a-Keto-isovalerate | Generator | a-Keto-isovaleric acid | Generator | alpha-Keto-isovalerate | Generator | Α-keto-isovalerate | Generator | Α-keto-isovaleric acid | Generator | a-Ketovaline | Generator | Α-ketovaline | Generator | a-oxo-b-Methylbutyricacid | Generator | Α-oxo-β-methylbutyricacid | Generator | a-Oxoisovalerate | Generator | a-Oxoisovaleric acid | Generator | alpha-Oxoisovalerate | Generator | Α-oxoisovalerate | Generator | Α-oxoisovaleric acid | Generator | Dimethylpyruvate | Generator | Isopropylglyoxylate | Generator | 2-Oxoisopentanoic acid | Generator | a-Ketoisovalerate | Generator | a-Ketoisovaleric acid | Generator | alpha-Ketoisovalerate | Generator | Α-ketoisovalerate | Generator | Α-ketoisovaleric acid | Generator | 2-Ketoisvaleric acid | HMDB | 2-oxo-3-Methyl-butyrate | HMDB | 3-Methyl-2-oxo-butanoate | HMDB | 3-Methyl-2-oxo-butanoic acid | HMDB | 3-Methyl-2-oxo-butyrate | HMDB | 3-Methyl-2-oxo-butyric acid | HMDB | 3-Methyl-2-oxobutinoate | HMDB | 3-Methyl-2-oxobutinoic acid | HMDB | a-Keto-b-methylbutyrate | HMDB | a-Keto-b-methylbutyric acid | HMDB | a-oxo-b-Methylbutyrate | HMDB | a-oxo-b-Methylbutyric acid | HMDB | alpha-Keto-beta-methylbutyrate | HMDB | alpha-Keto-beta-methylbutyric acid | HMDB | alpha-oxo-beta-Methylbutyrate | HMDB | alpha-oxo-beta-Methylbutyric acid | HMDB | Ketovaline | HMDB | alpha-Ketoisopentanoic acid | HMDB | alpha-Ketoisovaleric acid | Generator, MeSH |
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Chemical Formula | C5H8O3 |
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Average Molecular Weight | 116.1152 |
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Monoisotopic Molecular Weight | 116.047344122 |
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IUPAC Name | 3-methyl-2-oxobutanoic acid |
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Traditional Name | α-ketoisovalerate |
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CAS Registry Number | 759-05-7 |
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SMILES | CC(C)C(=O)C(O)=O |
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InChI Identifier | InChI=1S/C5H8O3/c1-3(2)4(6)5(7)8/h3H,1-2H3,(H,7,8) |
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InChI Key | QHKABHOOEWYVLI-UHFFFAOYSA-N |
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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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Ontology |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Indirect biological role: Biological role: Industrial application: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 31.5 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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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-9500000000-ff936b879a69b5d118f8 | Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-000i-8920000000-e37b37d64d43dcf763f0 | Spectrum | GC-MS | GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS) | splash10-000i-9400000000-e3995acc4818a98d0f48 | Spectrum | GC-MS | GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS) | splash10-0f79-9720000000-5d89487273e44ea61a68 | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-000i-9700000000-209c737dcac7df2b198c | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0f79-5920000000-759a2f01b4f52767ade2 | Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-000i-9500000000-ff936b879a69b5d118f8 | Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-000i-8920000000-e37b37d64d43dcf763f0 | Spectrum | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-000i-9400000000-e3995acc4818a98d0f48 | Spectrum | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0f79-9720000000-5d89487273e44ea61a68 | Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-000i-7900000000-7e325567183fb56996d5 | Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0ufr-0930000000-be90b06add7135b4a539 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-00dl-9000000000-52f9d8fc8386e4c512fe | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-006x-9600000000-52aefdc997dac92c8459 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-000i-9000000000-10ab58a33e9ca7dbace0 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-000i-9000000000-ad51ff01c94b6046ad64 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-014i-0900000000-9993174a7b1801b90ddb | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-00xr-9500000000-293818b81e0879b6feb2 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-00di-9000000000-75058f27a2178b9cf121 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-0006-9000000000-4c20af39e8ee009d5278 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-014i-0900000000-9993174a7b1801b90ddb | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-00xr-9500000000-1a58c6a6b4f5477dabdd | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-00di-9000000000-75058f27a2178b9cf121 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0006-9000000000-cc4465a47e663be66df5 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-IT , negative | splash10-00di-9100000000-19511890852fce513a02 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00r2-9400000000-21f8c3fae79161c82099 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00dl-9000000000-5f25e41413738bb6b5d7 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-801af00dea93fcfd637d | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-01b9-8900000000-5185c7dfc72c25069904 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00xs-9200000000-7e2a275a65197f96f5d7 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0600-9000000000-0013e0ff06f9896a1337 | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,1H] 2D NMR Spectrum | Not Available | Spectrum |
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Biological Properties |
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Cellular Locations | - Cytoplasm
- Extracellular
- Membrane
- Mitochondria
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Biospecimen Locations | - Blood
- Cerebrospinal Fluid (CSF)
- Feces
- Saliva
- Urine
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 14.0 (0.0-28.0) uM | Children (1-13 years old) | Both | Normal | | details | Blood | Detected and Quantified | 11.0 +/- 1.7 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Female | Normal | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 6 +/- 3 uM | Adult (>18 years old) | Both | Normal | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 8.2 +/- 6.8 uM | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Saliva | Detected and Quantified | 0.679 +/- 0.369 uM | Adult (>18 years old) | Female | Normal | | details | Saliva | Detected and Quantified | 0.752 +/- 0.287 uM | Adult (>18 years old) | Not Specified | Normal | | details | Saliva | Detected and Quantified | 1.06 +/- 0.436 uM | Adult (>18 years old) | Not Specified | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected and Quantified | 0.345 +/- 0.858 uM | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected and Quantified | 0.434 +/- 0.382 uM | Adult (>18 years old) | Female | Normal | | details | Saliva | Detected and Quantified | 0.656 +/- 0.399 uM | Adult (>18 years old) | Female | Normal | | details | Urine | Detected and Quantified | 0.78-1.2 umol/mmol creatinine | Adult (>18 years old) | Female | Normal | | details | Urine | Detected and Quantified | 0.16 +/- 0.48 umol/mmol creatinine | Infant (0-1 year old) | Both | Normal | | details | Urine | Detected and Quantified | 0.5 (0.2-1.1) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.13 (0.00-0.54) umol/mmol creatinine | Adult (>18 years old) | Male | Normal | | details | Urine | Detected and Quantified | 0.07 (0.01-0.45) umol/mmol creatinine | Adult (>18 years old) | Female | Normal | | details | Urine | Detected and Quantified | 0.79-1.1 umol/mmol creatinine | Adult (>18 years old) | Male | Normal | | details | Urine | Detected and Quantified | 0.07 (0.01-0.45) umol/mmol creatinine | Adult (>18 years old) | Female | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected and Quantified | 10.7 +/- 5.5 uM | Adult (>18 years old) | Both | Heart Transplant | | details | Blood | Detected and Quantified | 237 uM | Children (1-13 years old) | Female | Maple syrup urine disease | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 189 uM | Children (1-13 years old) | Female | Maple syrup urine disease | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal Cancer | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Bladder cancer | | details | Urine | Detected and Quantified | 550.00 (300.00-800.00) umol/mmol creatinine | Adult (>18 years old) | Both | Maple syrup urine disease (MSUD). When treated, the concentrations are 1-2 uM/mM. | | details | Urine | Detected and Quantified | 550.00 (300.00-800.00) umol/mmol creatinine | Children (1-13 years old) | Both | Maple syrup urine disease (MSUD). When treated, the concentrations are 1-2 uM/mM. | | details |
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Associated Disorders and Diseases |
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Disease References | Colorectal cancer |
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- Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
| Maple syrup urine disease |
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- G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium.
- Wendel, U., Becker, K., Przyrembel, H. et al. (1980). Peritoneal dialysis in maple-syrup-urine disease: Studies on branched-chain amino and keto acids. Eur J Pediatr (1980) 134: 57. https://doi.org/10.1007/BF00442404. Eur J Pediatr.
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Associated OMIM IDs | - 114500 (Colorectal cancer)
- 248600 (Maple syrup urine disease)
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External Links |
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DrugBank ID | DB04074 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB012250 |
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KNApSAcK ID | C00007623 |
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Chemspider ID | 48 |
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KEGG Compound ID | C00141 |
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BioCyc ID | 2-KETO-ISOVALERATE |
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BiGG ID | 34011 |
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Wikipedia Link | Alpha-Ketoisovaleric acid |
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METLIN ID | 5091 |
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PubChem Compound | 49 |
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PDB ID | Not Available |
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ChEBI ID | 16530 |
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Food Biomarker Ontology | Not Available |
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VMH ID | 3MOB |
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MarkerDB ID | MDB00000009 |
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References |
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Synthesis Reference | Pirrung, Michael C.; Ha, Hyun Joon; Holmes, Christopher P. Purification and inhibition of spinach a,b-dihydroxyacid dehydratase . Journal of Organic Chemistry (1989), 54(7), 1543-8. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Schaefer K, von Herrath D, Erley CM, Asmus G: Calcium ketovaline as new therapy for uremic hyperphosphatemia. Miner Electrolyte Metab. 1990;16(6):362-4. [PubMed:2089249 ]
- Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. [PubMed:2026685 ]
- Livesey G, Lund P: Binding of branched-chain 2-oxo acids to bovine serum albumin. Biochem J. 1982 Apr 15;204(1):265-72. [PubMed:7115325 ]
- Shigematsu Y, Kikuchi K, Momoi T, Sudo M, Kikawa Y, Nosaka K, Kuriyama M, Haruki S, Sanada K, Hamano N, et al.: Organic acids and branched-chain amino acids in body fluids before and after multiple exchange transfusions in maple syrup urine disease. J Inherit Metab Dis. 1983;6(4):183-9. [PubMed:6422161 ]
- Chuang DT, Niu WL, Cox RP: Activities of branched-chain 2-oxo acid dehydrogenase and its components in skin fibroblasts from normal and classical-maple-syrup-urine-disease subjects. Biochem J. 1981 Oct 15;200(1):59-67. [PubMed:6895847 ]
- Lee SH, Kim SO, Chung BC: Gas chromatographic-mass spectrometric determination of urinary oxoacids using O-(2,3,4,5,6-pentafluorobenzyl)oxime-trimethylsilyl ester derivatization and cation-exchange chromatography. J Chromatogr B Biomed Sci Appl. 1998 Nov 20;719(1-2):1-7. [PubMed:9869358 ]
- Gallina DL, Dominguez JM, Hoschoian JC, Barrio JR: Maintenance of nitrogen balance in a young woman by substitution of -ketoisovaleric acid for valine. J Nutr. 1971 Sep;101(9):1165-7. [PubMed:5096137 ]
- Schauder P, Schroder K, Langenbeck U: Serum branched-chain amino and keto acid response to a protein-rich meal in man. Ann Nutr Metab. 1984;28(6):350-6. [PubMed:6393856 ]
- Tsuchiya H, Hashizume I, Tokunaga T, Tatsumi M, Takagi N, Hayashi T: High-performance liquid chromatography of alpha-keto acids in human saliva. Arch Oral Biol. 1983;28(11):989-92. [PubMed:6581765 ]
- Yudkoff M, Daikhin Y, Nissim I, Horyn O, Luhovyy B, Lazarow A, Nissim I: Brain amino acid requirements and toxicity: the example of leucine. J Nutr. 2005 Jun;135(6 Suppl):1531S-8S. [PubMed:15930465 ]
- Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
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