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Record Information |
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Version | 1.0 |
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Creation Date | 2016-09-30 22:19:07 UTC |
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Update Date | 2020-06-04 20:14:40 UTC |
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BMDB ID | BMDB0000060 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Acetoacetic acid |
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Description | Acetoacetic acid, also known as 3-oxobutyrate or 3-oxobutanoic acid, 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. Acetoacetic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Acetoacetic acid exists in all living species, ranging from bacteria to humans. Acetoacetic acid is a potentially toxic compound. Acetoacetic acid has been found to be associated with several diseases known as ketoacidosis, irritable bowel syndrome, anoxia, and diabetes mellitus type 2; also acetoacetic acid has been linked to the inborn metabolic disorders including glucose transporter type 1 deficiency syndrome. |
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Structure | |
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Synonyms | Value | Source |
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3-Ketobutanoic acid | ChEBI | 3-Ketobutyric acid | ChEBI | 3-Oxobutanoic acid | ChEBI | 3-Oxobutyric acid | ChEBI | beta-Ketobutyric acid | ChEBI | 3-Ketobutanoate | Generator | 3-Ketobutyrate | Generator | 3-Oxobutanoate | Generator | 3-Oxobutyrate | Generator | b-Ketobutyrate | Generator | b-Ketobutyric acid | Generator | beta-Ketobutyrate | Generator | Β-ketobutyrate | Generator | Β-ketobutyric acid | Generator | Acetoacetate | Generator | Acetoacetic acid, calcium salt | MeSH | Acetoacetic acid, lithium salt | MeSH | Acetoacetic acid, sodium salt | MeSH | Oxobutyrate | MeSH | Sodium acetoacetate | MeSH | 3-oxo-Butanoate | HMDB | 3-oxo-Butanoic acid | HMDB | Diacetate | HMDB | Diacetic acid | HMDB |
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Chemical Formula | C4H6O3 |
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Average Molecular Weight | 102.0886 |
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Monoisotopic Molecular Weight | 102.031694058 |
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IUPAC Name | Not Available |
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Traditional Name | Not Available |
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CAS Registry Number | 541-50-4 |
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SMILES | Not Available |
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InChI Identifier | InChI=1S/C4H6O3/c1-3(5)2-4(6)7/h2H2,1H3,(H,6,7) |
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InChI Key | WDJHALXBUFZDSR-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 | - Short-chain keto acid
- Beta-keto acid
- 1,3-dicarbonyl compound
- Beta-hydroxy ketone
- Ketone
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- 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 | - Cytoplasm
- Mitochondria
- Peroxisome
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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 | 36.5 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 1000 mg/mL at 20 °C | 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 | - Cytoplasm
- Mitochondria
- Peroxisome
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Biospecimen Locations | - Blood
- Fibroblasts
- Leukocyte
- Liver
- Milk
- Neuron
- Ruminal Fluid
- Spleen
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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 | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Fibroblasts | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Leukocyte | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Liver | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 4 - 14 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 40 +/- 2 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Neuron | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Spleen | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Treated with growth-promoting hormones | | details |
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External Links |
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HMDB ID | HMDB0000060 |
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DrugBank ID | DB01762 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB112157 |
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KNApSAcK ID | C00007458 |
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Chemspider ID | 94 |
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KEGG Compound ID | C00164 |
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BioCyc ID | 3-KETOBUTYRATE |
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BiGG ID | Not Available |
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Wikipedia Link | Acetoacetic_acid |
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METLIN ID | Not Available |
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PubChem Compound | 96 |
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PDB ID | Not Available |
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ChEBI ID | 15344 |
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References |
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Synthesis Reference | Lopez-Soriano, F. J.; Argiles, J. M. A simple method for the preparation of acetoacetate. Analytical Letters (1985), 18(B5), 589-92. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Enjalbert F, Nicot MC, Bayourthe C, Moncoulon R: Ketone bodies in milk and blood of dairy cows: relationship between concentrations and utilization for detection of subclinical ketosis. J Dairy Sci. 2001 Mar;84(3):583-9. doi: 10.3168/jds.S0022-0302(01)74511-0. [PubMed:11286410 ]
- Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9. [PubMed:22098372 ]
- Lu J, Antunes Fernandes E, Paez Cano AE, Vinitwatanakhun J, Boeren S, van Hooijdonk T, van Knegsel A, Vervoort J, Hettinga KA: Changes in milk proteome and metabolome associated with dry period length, energy balance, and lactation stage in postparturient dairy cows. J Proteome Res. 2013 Jul 5;12(7):3288-96. doi: 10.1021/pr4001306. Epub 2013 Jun 5. [PubMed:23738862 ]
- Antunes-Fernandes EC, van Gastelen S, Dijkstra J, Hettinga KA, Vervoort J: Milk metabolome relates enteric methane emission to milk synthesis and energy metabolism pathways. J Dairy Sci. 2016 Aug;99(8):6251-6262. doi: 10.3168/jds.2015-10248. Epub 2016 May 26. [PubMed:27236769 ]
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