acetone (CHEBI:15347)

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CHEBI:15347 - acetone

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ChEBI Name	acetone

ChEBI ID	CHEBI:15347

Definition	A methyl ketone that consists of propane bearing an oxo group at C2.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:40571, CHEBI:2398, CHEBI:13708, CHEBI:22182

Supplier Information	eMolecules:474422, ZINC000000895111

Download	Molfile XML SDF

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10 9 0 0 0 0 999 V2000

-0.4723 1.0743 0.4935 C 0 0 0 0 0 0 0 0 0 1 0 0

-0.4723 -0.2846 -0.0011 C 0 0 0 0 0 0 0 0 0 2 0 0

0.7436 -0.8937 -0.4930 C 0 0 0 0 0 0 0 0 0 3 0 0

-1.5146 -0.9273 -0.0036 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.4603 1.3943 0.8295 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.1472 1.7560 -0.2947 H 0 0 0 0 0 0 0 0 0 0 0 0

0.2152 1.1621 1.3368 H 0 0 0 0 0 0 0 0 0 0 0 0

0.5870 -1.9195 -0.8316 H 0 0 0 0 0 0 0 0 0 0 0 0

1.1336 -0.3170 -1.3337 H 0 0 0 0 0 0 0 0 0 0 0 0

1.4960 -0.9109 0.2978 H 0 0 0 0 0 0 0 0 0 0 0 0

2 1 1 0 0 0 0

3 2 1 0 0 0 0

4 2 2 0 0 0 0

1 5 1 0 0 0 0

1 6 1 0 0 0 0

1 7 1 0 0 0 0

3 8 1 0 0 0 0

3 9 1 0 0 0 0

3 10 1 0 0 0 0

M END): 18 ms

reading 10 atoms

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Wikipedia	License
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. It is normally present 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.
Read full article at Wikipedia

Formula

C3H6O

Net Charge

Average Mass

58.07914

Monoisotopic Mass

58.04186

InChI

InChI=1S/C3H6O/c1-3(2)4/h1-2H3

InChIKey

CSCPPACGZOOCGX-UHFFFAOYSA-N

SMILES

CC(C)=O

Metabolite of Species	Details
Homo sapiens (NCBI:txid9606)	See: DOI

Roles Classification
Chemical Role(s):	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.

Biological Role(s):	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 )

Application(s):	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 )

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	acetone (CHEBI:15347) has role EC 3.5.1.4 (amidase) inhibitor (CHEBI:77941) acetone (CHEBI:15347) has role human metabolite (CHEBI:77746) acetone (CHEBI:15347) has role polar aprotic solvent (CHEBI:48358) acetone (CHEBI:15347) is a ketone body (CHEBI:73693) acetone (CHEBI:15347) is a methyl ketone (CHEBI:51867) acetone (CHEBI:15347) is a propanones (CHEBI:26292) acetone (CHEBI:15347) is a volatile organic compound (CHEBI:134179)

Incoming	1-hydroxy-3-methoxyacetone (CHEBI:37551) has functional parent acetone (CHEBI:15347) aminoacetone (CHEBI:17906) has functional parent acetone (CHEBI:15347) bromoacetone (CHEBI:51845) has functional parent acetone (CHEBI:15347) chloroacetone (CHEBI:47220) has functional parent acetone (CHEBI:15347) hydroxyacetone (CHEBI:27957) has functional parent acetone (CHEBI:15347) 2-oxopropylidene group (CHEBI:48057) is substituent group from acetone (CHEBI:15347) 2-oxopropylidyne group (CHEBI:48059) is substituent group from acetone (CHEBI:15347) acetonyl group (CHEBI:48056) is substituent group from acetone (CHEBI:15347)

IUPAC Name

propan-2-one

Synonyms	Sources
2-Propanone	KEGG COMPOUND
Aceton	ChemIDplus
Acetone	KEGG COMPOUND
ACETONE	PDBeChem
acetone	UniProt
acétone	ChEBI
Azeton	ChEBI
beta-Ketopropane	HMDB
Dimethyl ketone	KEGG COMPOUND
diméthylcétone	ChEBI
Dimethylketon	ChEBI
dimethylketone	MetaCyc
methyl ketone	ChemIDplus
Propanon	ChEBI
propanone	ChemIDplus
Pyroacetic ether	HMDB

Manual Xrefs	Databases
Acetone	Wikipedia
ACETONE	MetaCyc
ACN	PDBeChem
C00207	KEGG COMPOUND
c0556	UM-BBD
D02311	KEGG DRUG
HMDB0001659	HMDB
LMFA12000057	LIPID MAPS
View more database links

Registry Numbers	Types	Sources
1466	Gmelin Registry Number	Gmelin
635680	Reaxys Registry Number	Reaxys
67-64-1	CAS Registry Number	NIST Chemistry WebBook
67-64-1	CAS Registry Number	ChemIDplus

Citations

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]

Last Modified

10 July 2017

CHEBI:15347 - acetone

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