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| Acetone (2-propanone or dimethyl ketone) is an organic compound with the formula (CH3)2CO. It is the simplest and smallest ketone (R−C(=O)−R'). It is a colorless, highly volatile, and flammable liquid with a characteristic pungent odor.
Acetone is miscible with water and serves as an important organic solvent in industry, home, and laboratory. About 6.7 million tonnes were produced worldwide in 2010, mainly for use as a solvent and for production of methyl methacrylate and bisphenol A, which are precursors to widely used plastics. It is a common building block in organic chemistry. It serves as a solvent in household products such as nail polish remover and paint thinner. It has volatile organic compound (VOC)-exempt status in the United States.
Acetone is produced and disposed of in the human body through normal metabolic processes. Small quantities of it are present naturally in blood and urine. People with diabetic ketoacidosis produce it in larger amounts. Ketogenic diets that increase ketone bodies (acetone, β-hydroxybutyric acid and acetoacetic acid) in the blood are used to counter epileptic attacks in children who suffer from refractory epilepsy. |
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Read full article at Wikipedia
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| InChI=1S/C3H6O/c1-3(2)4/h1-2H3 |
| CSCPPACGZOOCGX-UHFFFAOYSA-N |
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Homo sapiens
(NCBI:txid9606)
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See:
DOI
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polar aprotic solvent
A solvent with a comparatively high relative permittivity (or dielectric constant), greater than ca. 15, and a sizable permanent dipole moment, that cannot donate suitably labile hydrogen atoms to form strong hydrogen bonds.
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EC 3.5.1.4 (amidase) inhibitor
An EC 3.5.1.* (non-peptide linear amide C-N hydrolase) inhibitor that interferes with the action of amidase (EC 3.5.1.4).
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via ketone body )
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polar aprotic solvent
A solvent with a comparatively high relative permittivity (or dielectric constant), greater than ca. 15, and a sizable permanent dipole moment, that cannot donate suitably labile hydrogen atoms to form strong hydrogen bonds.
neuroprotective agent
Any compound that can be used for the treatment of neurodegenerative disorders.
(via ketone body )
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View more via ChEBI Ontology
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2-Propanone
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KEGG COMPOUND
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Aceton
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ChemIDplus
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Acetone
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KEGG COMPOUND
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ACETONE
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PDBeChem
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acetone
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UniProt
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acétone
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ChEBI
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Azeton
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ChEBI
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beta-Ketopropane
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HMDB
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Dimethyl ketone
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KEGG COMPOUND
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diméthylcétone
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ChEBI
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Dimethylketon
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ChEBI
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dimethylketone
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MetaCyc
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methyl ketone
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ChemIDplus
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Propanon
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ChEBI
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propanone
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ChemIDplus
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Pyroacetic ether
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HMDB
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Acetone
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Wikipedia
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ACETONE
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MetaCyc
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ACN
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PDBeChem
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C00207
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KEGG COMPOUND
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c0556
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UM-BBD
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D02311
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KEGG DRUG
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HMDB0001659
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HMDB
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LMFA12000057
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LIPID MAPS
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| View more database links |
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1466
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Gmelin Registry Number
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Gmelin
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635680
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Reaxys Registry Number
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Reaxys
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67-64-1
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CAS Registry Number
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NIST Chemistry WebBook
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67-64-1
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CAS Registry Number
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ChemIDplus
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Makhongela HS, Glowacka AE, Agarkar VB, Sewell BT, Weber B, Cameron RA, Cowan DA, Burton SG (2007)
A novel thermostable nitrilase superfamily amidase from Geobacillus pallidus showing acyl transfer activity.
Applied microbiology and biotechnology 75, 801-811 [PubMed:17347819]
[show Abstract]
An amidase (EC 3.5.1.4) in branch 2 of the nitrilase superfamily, from the thermophilic strain Geobacillus pallidus RAPc8, was produced at high expression levels (20 U/mg) in small-scale fermentations of Escherichia coli. The enzyme was purified to 90% homogeneity with specific activity of 1,800 U/mg in just two steps, namely, heat-treatment and gel permeation chromatography. Sodium dodecyl sulfate-polyacrylamide gel electrophoresis (SDS-PAGE) and electron microscopic (EM) analysis of the homogenous enzyme showed the native enzyme to be a homohexamer of 38 kDa subunits. Analysis of the biochemical properties of the amidase showed that the optimal temperature and pH for activity were 50 and 7.0 degrees C, respectively. The amidase exhibited high thermal stability at 50 and 60 degrees C, with half-lives greater than 5 h at both temperatures. At 70 and 80 degrees C, the half-life values were 43 and 10 min, respectively. The amidase catalyzed the hydrolysis of low molecular weight aliphatic amides, with D: -selectivity towards lactamide. Inhibition studies showed activation/inhibition data consistent with the presence of a catalytically active thiol group. Acyl transfer reactions were demonstrated with acetamide, propionamide, isobutyramide, and acrylamide as substrates and hydroxylamine as the acyl acceptor; the highest reaction rate being with isobutyramide. Immobilization by entrapment in polyacrylamide gels, covalent binding on Eupergit C beads at 4 degrees C and on Amberlite-XAD57 resulted in low protein binding and low activity, but immobilization on Eupergit C beads at 25 degrees C with cross-linking resulted in high protein binding yield and high immobilized specific activity (80% of non-immobilized activity). Characterization of Eupergit C-immobilized preparations showed that the optimum reaction temperature was unchanged, the pH range was somewhat broadened, and stability was enhanced giving half-lives of 52 min at 70 degrees C and 30 min at 80 degrees C. The amidase has potential for application under high temperature conditions as a biocatalyst for D: -selective amide hydrolysis producing enantiomerically pure carboxylic acids and for production of novel amides by acyl transfer. | Salek RM, Maguire ML, Bentley E, Rubtsov DV, Hough T, Cheeseman M, Nunez D, Sweatman BC, Haselden JN, Cox RD, Connor SC, Griffin JL (2007)
A metabolomic comparison of urinary changes in type 2 diabetes in mouse, rat, and human.
Physiological genomics 29, 99-108 [PubMed:17190852]
[show Abstract]
Type 2 diabetes mellitus is the result of a combination of impaired insulin secretion with reduced insulin sensitivity of target tissues. There are an estimated 150 million affected individuals worldwide, of whom a large proportion remains undiagnosed because of a lack of specific symptoms early in this disorder and inadequate diagnostics. In this study, NMR-based metabolomic analysis in conjunction with multivariate statistics was applied to examine the urinary metabolic changes in two rodent models of type 2 diabetes mellitus as well as unmedicated human sufferers. The db/db mouse and obese Zucker (fa/fa) rat have autosomal recessive defects in the leptin receptor gene, causing type 2 diabetes. 1H-NMR spectra of urine were used in conjunction with uni- and multivariate statistics to identify disease-related metabolic changes in these two animal models and human sufferers. This study demonstrates metabolic similarities between the three species examined, including metabolic responses associated with general systemic stress, changes in the TCA cycle, and perturbations in nucleotide metabolism and in methylamine metabolism. All three species demonstrated profound changes in nucleotide metabolism, including that of N-methylnicotinamide and N-methyl-2-pyridone-5-carboxamide, which may provide unique biomarkers for following type 2 diabetes mellitus progression. |
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