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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 | Not Available |
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Traditional Name | Not Available |
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CAS Registry Number | 759-05-7 |
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SMILES | Not Available |
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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 | Not Available |
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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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