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Butanone (T3D4589)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (1)XML
Targets (1)
Record Information
Version2.0
Creation Date2014-09-05 17:11:35 UTC
Update Date2014-12-24 20:26:53 UTC
Accession NumberT3D4589
Identification
Common NameButanone
ClassSmall Molecule
DescriptionButanone occurs as a natural product. It is made by some trees and found in some fruits and vegetables in small amounts. It is also released to the air from car and truck exhausts. The known health effects to people from exposure to butanone are irritation of the nose, throat, skin, and eyes. (wikipedia).
Compound Type
  • Food Toxin
  • Household Toxin
  • Lachrymator
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Plant Toxin
  • Pollutant
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Synonym
2-Butanone
Butan-2-one
Ethyl methyl ketone
MEK
Methyl ethyl ketone
Chemical FormulaC4H8O
Average Molecular Mass72.106 g/mol
Monoisotopic Mass72.058 g/mol
CAS Registry Number78-93-3
IUPAC Namebutan-2-one
Traditional Namemethyl(ethyl) ketone
SMILESCCC(C)=O
InChI IdentifierInChI=1S/C4H8O/c1-3-4(2)5/h3H2,1-2H3
InChI KeyInChIKey=ZWEHNKRNPOVVGH-UHFFFAOYSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentKetones
Alternative Parents
Substituents
  • Ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue Locations
  • Pancreas
  • Stratum Corneum
PathwaysNot Available
Applications
Biological Roles
Chemical Roles
Physical Properties
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point-86.6 °C
Boiling PointNot Available
Solubility223.0 mg/mL
LogP0.29
Predicted Properties
PropertyValueSource
Water Solubility93 g/LALOGPS
logP0.41ALOGPS
logP0.81ChemAxon
logS0.11ALOGPS
pKa (Strongest Acidic)19.68ChemAxon
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity20.82 m³·mol⁻¹ChemAxon
Polarizability8.28 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-6d2b5f585a1d1bc5a8fb2017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-9d38ccb9b91100a7ec9a2017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-c956d364a703ad576f742017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-6d2b5f585a1d1bc5a8fb2018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-9d38ccb9b91100a7ec9a2018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-c956d364a703ad576f742018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-4e6c1888a6b9f92a7e0c2017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-05fr-9000000000-ce6384a82cdbc3c321312012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-05fr-9000000000-d2220466d540748715a62012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00di-9000000000-5c396f6150d62df63bf82012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0006-9000000000-342b15824555f25c17ae2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0006-9000000000-9d38ccb9b91100a7ec9a2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0006-9000000000-c956d364a703ad576f742012-08-31View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fr-9000000000-df1c4f4393ad8e083cee2015-05-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-9000000000-5db9dc68e554d23fe4ca2015-05-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-e76aaa16e1218b6b92e02015-05-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fr-9000000000-df1c4f4393ad8e083cee2015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-9000000000-5db9dc68e554d23fe4ca2015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-e76aaa16e1218b6b92e02015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-75ee4bf0cca979df2fee2015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-a0882d603db69a60cd2b2015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-9000000000-2b71687b4480da0a40a82015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-75ee4bf0cca979df2fee2015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-a0882d603db69a60cd2b2015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-9000000000-2b71687b4480da0a40a82015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000000-1924391f943e092b44862021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-b1f7b08e06d7bb20906d2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052o-9000000000-d0609c2afd15f75e6cbb2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-77e5dcf17bd83eca2c672021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dl-9000000000-91a2cd469019aa3b0b9c2021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-fa8f185babb9571dbb912021-09-23View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-389580382a5be690811f2014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Not Available2012-12-04View Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Not Available2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental)Not Available2014-09-23View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not Available2012-12-05View Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesIt is made by some trees and found in some fruits and vegetables in small amounts.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB00474
PubChem Compound ID6569
ChEMBL IDCHEMBL15849
ChemSpider ID6321
KEGG IDC02845
UniProt IDNot Available
OMIM ID
ChEBI ID28398
BioCyc IDDIHYDROXY-BUTANONE-P
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkButanone
References
Synthesis ReferenceVergnaud, Paul. The manufacture of butanediol and butanone. (1950),
MSDSLink
General References
  1. Weddle DL, Tithoff P, Williams M, Schuller HM: Beta-adrenergic growth regulation of human cancer cell lines derived from pancreatic ductal carcinomas. Carcinogenesis. 2001 Mar;22(3):473-9. [11238189 ]
  2. Goldsmith LB, Friberg SE, Wahlberg JE: The effect of solvent extraction on the lipids of the stratum corneum in relation to observed immediate whitening of the skin. Contact Dermatitis. 1988 Nov;19(5):348-50. [3233954 ]
  3. Carmella SG, Akerkar S, Hecht SS: Metabolites of the tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in smokers' urine. Cancer Res. 1993 Feb 15;53(4):721-4. [8428352 ]
  4. Stich HF, Parida BB, Brunnemann KD: Localized formation of micronuclei in the oral mucosa and tobacco-specific nitrosamines in the saliva of "reverse" smokers, Khaini-tobacco chewers and gudakhu users. Int J Cancer. 1992 Jan 21;50(2):172-6. [1730509 ]
  5. Nair J, Ohshima H, Friesen M, Croisy A, Bhide SV, Bartsch H: Tobacco-specific and betel nut-specific N-nitroso compounds: occurrence in saliva and urine of betel quid chewers and formation in vitro by nitrosation of betel quid. Carcinogenesis. 1985 Feb;6(2):295-303. [3971493 ]
  6. Prokopczyk B, Cox JE, Hoffmann D, Waggoner SE: Identification of tobacco-specific carcinogen in the cervical mucus of smokers and nonsmokers. J Natl Cancer Inst. 1997 Jun 18;89(12):868-73. [9196253 ]
  7. Hecht SS, Carmella SG, Ye M, Le KA, Jensen JA, Zimmerman CL, Hatsukami DK: Quantitation of metabolites of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone after cessation of smokeless tobacco use. Cancer Res. 2002 Jan 1;62(1):129-34. [11782369 ]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Transient receptor potential cation channel subfamily A member 1
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 ]