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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:02:43 UTC
HMDB IDHMDB00474
Secondary Accession NumbersNone
Metabolite Identification
Common NameButanone
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).
Structure
Thumb
Synonyms
ValueSource
2-ButanonChEBI
2-ButanoneChEBI
3-ButanoneChEBI
AethylmethylketonChEBI
ButanoneChEBI
Butanone 2ChEBI
C2H5COCH3ChEBI
Ethyl methyl cetoneChEBI
Ethyl methyl ketoneChEBI
Ethyl(methyl) ketoneChEBI
Ethylmethyl ketoneChEBI
EthylmethylketonChEBI
MeetcoChEBI
MEKChEBI
Methyl acetoneChEBI
Methyl ethyl cetoneChEBI
Methyl ethyl ketoneChEBI
Methyl(ethyl) ketoneChEBI
MethylacetoneChEBI
Methylethyl ketoneChEBI
MethylethylketonChEBI
OxobutaneChEBI
Chemical FormulaC4H8O
Average Molecular Weight72.1057
Monoisotopic Molecular Weight72.057514878
IUPAC Namebutan-2-one
Traditional Namemethyl(ethyl) ketone
CAS Registry Number78-93-3
SMILES
CCC(C)=O
InChI Identifier
InChI=1S/C4H8O/c1-3-4(2)5/h3H2,1-2H3
InChI KeyInChIKey=ZWEHNKRNPOVVGH-UHFFFAOYSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbonyl compounds
Sub ClassKetones
Direct ParentKetones
Alternative Parents
Substituents
  • Ketone
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-86.6 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility223.0 mg/mLNot Available
LogP0.29HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility93.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity20.82 m3·mol-1ChemAxon
Polarizability8.28 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-05fr-9000000000-ce6384a82cdbc3c32131View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-05fr-9000000000-d2220466d540748715a6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00di-9000000000-5c396f6150d62df63bf8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0006-9000000000-342b15824555f25c17aeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0006-9000000000-9d38ccb9b91100a7ec9aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0006-9000000000-c956d364a703ad576f74View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fr-9000000000-df1c4f4393ad8e083ceeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-9000000000-5db9dc68e554d23fe4caView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-e76aaa16e1218b6b92e0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fr-9000000000-df1c4f4393ad8e083ceeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-9000000000-5db9dc68e554d23fe4caView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-e76aaa16e1218b6b92e0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-75ee4bf0cca979df2feeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-a0882d603db69a60cd2bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-9000000000-2b71687b4480da0a40a8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-75ee4bf0cca979df2feeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-a0882d603db69a60cd2bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-9000000000-2b71687b4480da0a40a8View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-389580382a5be690811fView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Location
  • Pancreas
  • Stratum Corneum
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableNewborn (0-30 days old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified2.23 - 42.09 ppmChildren (1-13 years old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
SalivaDetected but not QuantifiedNot ApplicableChildren (1-13 years old)BothNormal details
UrineDetected and Quantified5.5 (0.0-11.0) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified0.07 (0.0-0.26) umol/mmol creatinineInfant (0-1 year old)BothNormal
    • Geigy Scientific ...
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified682.0 (69.0-1998.0) uMAdult (>18 years old)BothAlcohol intoxication details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Clostridium difficile infection
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Ulcerative Colitis
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected and Quantified0 - 136.19 ppmChildren (1-13 years old)Not Specified
Treated celiac disease
details
SalivaDetected but not QuantifiedNot ApplicableChildren (1-13 years old)BothCeliac disease details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothBreast cancer details
Associated Disorders and Diseases
Disease References
Alcoholism
  1. Jones AW, Lund M, Andersson E: Drinking drivers in Sweden who consume denatured alcohol preparations: an analytical-toxicological study. J Anal Toxicol. 1989 Jul-Aug;13(4):199-203. [2779169 ]
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB003383
KNApSAcK IDNot Available
Chemspider ID6321
KEGG Compound IDC02845
BioCyc IDDIHYDROXY-BUTANONE-P
BiGG IDNot Available
Wikipedia LinkButanone
NuGOwiki LinkHMDB00474
Metagene LinkHMDB00474
METLIN ID5461
PubChem Compound6569
PDB IDNot Available
ChEBI ID28398
References
Synthesis ReferenceVergnaud, Paul. The manufacture of butanediol and butanone. (1950),
Material Safety Data Sheet (MSDS)Download (PDF)
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 ]