| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 22:18:31 UTC |
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| Update Date | 2020-06-04 20:27:53 UTC |
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| BMDB ID | BMDB0000019 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Alpha-ketoisovaleric acid |
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| Description | alpha-Ketoisovaleric acid, also known as a-keto-isovalerate or 3-methyl-2-oxobutanoate, 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. alpha-Ketoisovaleric acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. alpha-Ketoisovaleric acid exists in all living species, ranging from bacteria to humans. alpha-Ketoisovaleric acid is a potentially toxic compound. alpha-Ketoisovaleric acid, with regard to humans, has been found to be associated with the diseases such as colorectal cancer; alpha-ketoisovaleric acid has also been linked to the inborn metabolic disorder maple syrup urine disease. |
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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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| Status | Detected and Quantified |
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| Origin | |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | - Cell membrane
- Cytoplasm
- Membrane
- Mitochondria
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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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| Spectra | |
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| Biological Properties |
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| Cellular Locations | - Cell membrane
- Cytoplasm
- Membrane
- Mitochondria
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| Biospecimen Locations | - Blood
- Mammary Gland
- Muscle
- Placenta
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| Pathways | |
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| Normal Concentrations |
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| Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 380 +/- 20 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 450 +/- 30 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 260 +/- 20 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 290 +/- 20 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Placenta | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details |
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| Abnormal Concentrations |
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| Not Available |
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| External Links |
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| HMDB ID | HMDB0000019 |
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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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| 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) | Not Available |
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| General References | Not Available |
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