Basic Info

Common NameAcetone(F03415)
2D Structure
Description

Acetone is one of the ketone bodies produced during ketoacidosis. Acetone is not regarded as a waste product of metabolism. However, its physiological role in biochemical machinery is not clear. A model for the role of acetone metabolism is presented that orders the events occurring in acetonemia in sequence: in diabetic ketosis or starvation, ketone body production (b-hydroxy-butyrate, acetoacetate) provides fuel for vital organs (heart, brain .) raising the chance of survival of the metabolic catastrophe. However, when ketone body production exceeds the degrading capacity, the accumulating acetoacetic acid presents a new challenge to the pH regulatory system. Acetone production and its further degradation to C3 fragments fulfill two purposes: the maintenance of pH buffering capacity and provision of fuel for peripheral tissues. Since ketosis develops under serious metabolic circumstances, all the mechanisms that balance or moderate the effects of ketosis enhance the chance for survival. From this point of view, the theory that transportable C3 fragments can serve as additional nutrients is a novel view of acetone metabolism which introduces a new approach to the study of acetone degradation, especially in understanding its physiological function and the interrelationship between liver and peripheral tissues. (A7724). Acetone is typically derived from acetoacetate through the action of microbial acetoacetate decarboxylases found in gut microflora. In chemistry, acetone is the simplest representative of the ketones. Acetone is a colorless, mobile, flammable liquid readily soluble in water, ethanol, ether, etc., and itself serves as an important solvent. Acetone is an irritant and inhalation may lead to hepatotoxic effects (causing liver damage).

FRCD IDF03415
CAS Number67-64-1
PubChem CID180
FormulaC3H6O
IUPAC Name

propan-2-one

InChI Key

CSCPPACGZOOCGX-UHFFFAOYSA-N

InChI

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

Canonical SMILES

CC(=O)C

Isomeric SMILES

CC(=O)C

WikipediaAcetone
Synonyms
        
            propanone
        
            Dimethylformaldehyde
        
            acetone
        
            2-propanone
        
            67-64-1
        
            Dimethyl ketone
        
            Methyl ketone
        
            Pyroacetic ether
        
            propan-2-one
        
            beta-Ketopropane
        
Classifies
                

                  
                    Predicted: Plant Toxin
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds
SubclassCarbonyl compounds
Intermediate Tree NodesNot available
Direct ParentKetones
Alternative Parents
Molecular FrameworkAliphatic acyclic compounds
SubstituentsKetone - Organic oxide - Hydrocarbon derivative - Aliphatic acyclic compound
DescriptionThis compound belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.

Properties

Property NameProperty Value
Molecular Weight58.08
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count1
Rotatable Bond Count0
Complexity26.3
Monoisotopic Mass58.042
Exact Mass58.042
XLogP-0.1
Formal Charge0
Heavy Atom Count4
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9818
Human Intestinal AbsorptionHIA+0.9959
Caco-2 PermeabilityCaco2+0.7526
P-glycoprotein SubstrateNon-substrate0.8012
P-glycoprotein InhibitorNon-inhibitor0.9272
Non-inhibitor0.9680
Renal Organic Cation TransporterNon-inhibitor0.9194
Distribution
Subcellular localizationMitochondria0.6207
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8279
CYP450 2D6 SubstrateNon-substrate0.9116
CYP450 3A4 SubstrateNon-substrate0.7043
CYP450 1A2 InhibitorNon-inhibitor0.8238
CYP450 2C9 InhibitorNon-inhibitor0.9596
CYP450 2D6 InhibitorNon-inhibitor0.9614
CYP450 2C19 InhibitorNon-inhibitor0.9477
CYP450 3A4 InhibitorNon-inhibitor0.9847
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9238
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9655
Non-inhibitor0.9569
AMES ToxicityNon AMES toxic0.9133
CarcinogensCarcinogens 0.7115
Fish ToxicityLow FHMT0.6453
Tetrahymena Pyriformis ToxicityLow TPT0.7916
Honey Bee ToxicityHigh HBT0.8176
BiodegradationReady biodegradable0.8501
Acute Oral ToxicityIII0.6238
Carcinogenicity (Three-class)Non-required0.7274

Model Value Unit
Absorption
Aqueous solubility0.1920LogS
Caco-2 Permeability1.5329LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.5293LD50, mol/kg
Fish Toxicity3.2181pLC50, mg/L
Tetrahymena Pyriformis Toxicity-1.2451pIGC50, ug/L

References

TitleJournalDatePubmed ID
Determination of total avilamycin residues as dichloroisoeverninic acid inporcine muscle, fat, and liver by LC-MS/MS.Food Chem2018 May 3029407936
Behavior of 11 Foodborne Bacteria on Whole and Cut Mangoes var. Ataulfo and Kent and Antibacterial Activities of Hibiscus sabdariffa Extracts and Chemical Sanitizers Directly onto Mangoes Contaminated with Foodborne Bacteria.J Food Prot2018 May29620488
Oolong tea and LR-White resin: a new method of plant sample preparation for transmission electron microscopy.J Microsc2018 May29334400
Identification and characterization of a novel alkalistable and salt-tolerantesterase from the deep-sea hydrothermal vent of the East Pacific Rise.Microbiologyopen2018 Mar 529504251
South African medicinal plant extracts active against influenza A virus.BMC Complement Altern Med2018 Mar 2729587734
Simultaneous Extraction and Determination of Preservatives and Antioxidants inJuice Samples by an Optimized Microextraction Method Using Central CompositeDesign and Validated with Accuracy Profile.J AOAC Int2018 Jun 2829954481
Solvent effect on endosulfan adsorption onto polymeric arginine-methacrylatecryogels.Environ Sci Pollut Res Int2018 Jun 2729951763
Toxicological effect of underutilized plant, Cleistanthus collinus leaf extracts against two major stored grain pests, the rice weevil, Sitophilus oryzae and red flour beetle, Tribolium castaneum.Ecotoxicol Environ Saf2018 Jun 1529454991
Antibacterial activity and in situ efficacy of Bidens pilosa Linn and Dichrostachys cinerea Wight et Arn extracts against common diarrhoea-causing waterborne bacteria.BMC Complement Altern Med2018 Jun 129859076
Evaluation of Antioxidant Properties, Phenolic Compounds, Anthelmintic, andCytotoxic Activities of Various Extracts Isolated from Nepeta cadmea: An Endemic Plant for Turkey.J Food Sci2018 Jun29746001
Phytochemical, Free Radical Scavenging and Antifungal Profile of Cuscutacampestris Yunck. Seeds.Chem Biodivers2018 Jul 19:e180017429874415
Analysis of the Active Constituents and Evaluation of the Biological Effects ofQuercus acuta Thunb. (Fagaceae) Extracts.Molecules2018 Jul 1930029475
Catalytic characteristics and application of l-asparaginase immobilized onaluminum oxide pellets.Int J Biol Macromol2018 Jul 1529572146
Development of magnetic dispersive solid phase extraction using toner powder asan efficient and economic sorbent in combination with dispersive liquid-liquidmicroextraction for extraction of some widely used pesticides in fruit juices.J Chromatogr A2018 Jan 1229174132
Effects of Highland Barley Bran Extract Rich in Phenolic Acids on the Formationof Nε-Carboxymethyllysine in a Biscuit Model.J Agric Food Chem2018 Feb 2829414239
Antibacterial Activities of Hibiscus sabdariffa Extracts and Chemical Sanitizers Directly on Green Leaves Contaminated with Foodborne Pathogens.J Food Prot2018 Feb29320233
Metalloproteomics Approach to Analyze Mercury in Breast Milk and Hair Samples of Lactating Women in Communities of the Amazon Basin, Brazil.Biol Trace Elem Res2018 Feb28547667
Anti-quorum sensing activity, toxicity in zebrafish (Danio rerio) embryos and phytochemical characterization of Trapa natans leaf extracts.J Ethnopharmacol2018 Aug 1029733941
A simple, rapid and novel method based on salting-out assisted liquid-liquid extraction for ochratoxin A determination in beer samples prior to ultra-high-performance liquid chromatography coupled to tandem mass spectrometry.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2018 Aug29877757
Organic Solvent as Internal Standards for Quantitative and High-Throughput LiquidInterfacial SERS Analysis in Complex Media.Anal Chem2018 Apr 1729584402

Targets

General Function:
Temperature-gated cation channel activity
Specific Function:
Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
Gene Name:
TRPA1
Uniprot ID:
O75762
Molecular Weight:
127499.88 Da
References
  1. Nilius B, Prenen J, Owsianik G: Irritating channels: the case of TRPA1. J Physiol. 2011 Apr 1;589(Pt 7):1543-9. doi: 10.1113/jphysiol.2010.200717. Epub 2010 Nov 15. [21078588 ]