| 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 | 3-oxobutanoic acid |
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| Traditional Name | acetoacetic acid |
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| CAS Registry Number | 541-50-4 |
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| SMILES | CC(=O)CC(O)=O |
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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 | |
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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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