| Record Information |
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| Version | 1.0 |
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| Creation date | 2015-10-09 22:29:17 UTC |
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| Update date | 2017-01-19 02:36:17 UTC |
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| FoodComEx ID | PC000220 |
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| FoodDB Record | FDB022024 |
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| Chemical Information |
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| Name | 2-Methyl-3-ketovaleric acid |
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| Description | 2-Methyl-3-ketovaleric acid is a metabolite of beta-leucine in the beta-keto pathway of leucine metabolism. 2-Methyl-3-ketovaleric acid is a known pathological metabolite and associated with propionic acidemia, especially during periods of ketoacidosis; a severe deficiency of propionyl-CoA carboxylase in cultured fibroblasts has been detected in some neonatal cases. (PMID 7389125, 6820422, 7119896, 7430116, 3356699)
2-Methyl-3-ketovaleric acid induces a strong activity of inosine-5'-monophosphate dehydrogenase (IMPDH; the rate-limiting enzyme in GTP synthesis), mimicking glucose. (PMID: 11145582) [HMDB] |
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| CAS Number | 14925-93-0 |
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| Structure | |
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| Synonyms | | Synonym | Source |
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| 2-Methyl-3-ketovalerate | hmdb | | 2-Methyl-3-oxo-pentanoate | hmdb | | 2-Methyl-3-oxo-pentanoic acid | hmdb | | 2-Methyl-3-oxovalerate | hmdb | | 2-Methyl-3-oxovaleric acid | hmdb | | beta-Ketoisocaproate | hmdb | | beta-Ketoisocaproic acid | hmdb |
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| Chemical Formula | C6H10O3 |
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| IUPAC name | 2-methyl-3-oxopentanoic acid |
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| InChI Identifier | InChI=1S/C6H10O3/c1-3-5(7)4(2)6(8)9/h4H,3H2,1-2H3,(H,8,9) |
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| InChI Key | QTLYPQZWYOHATR-UHFFFAOYSA-N |
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| Isomeric SMILES | CCC(=O)C(C)C(O)=O |
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| Average Molecular Weight | 130.1418 |
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| Monoisotopic Molecular Weight | 130.062994186 |
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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 | - Beta-keto acid
- Branched fatty acid
- Methyl-branched fatty acid
- Short-chain keto acid
- Beta-hydroxy ketone
- Fatty acyl
- 1,3-dicarbonyl compound
- 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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| Physico-Chemical Properties - Experimental |
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| Property | Value | Reference |
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| Experimental logP | Not Available | |
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| Experimental Water Solubility | Not Available | |
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| Melting Point | Not Available | |
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| Foods of Origin |
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| Food | Content Range | Average | Reference |
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| Food | | | Reference |
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| Production Data |
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| Production Method | commercial |
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| Production Method Reference | Not Available |
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| Production Method Reference File | Not Available |
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| Quantity Available | Production upon request, up to 500 mg |
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| Delivery Time | Not Available |
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| Storage Form | solid |
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| Storage Conditions | -80°C |
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| Stability | Not Available |
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| Purity | Not Available |
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| Spectra |
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| Spectral Data Upon Request | Not Available |
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| Provider Information |
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| Commercial Vendors |
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| Not Available |
