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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:57 UTC
HMDB IDHMDB01184
Secondary Accession NumbersNone
Metabolite Identification
Common NameMethyl propenyl ketone
DescriptionMethyl propenyl ketone is a volatile organic compound. Methyl propenyl ketone is occasionally found as a volatile component of normal human biofluids. It is found as a volatile in the hawthorn fruit upon ripening, and also is part of the scent components of the urine of some animals. (PMID: 5556886 , 16770722 , 15739361 , 914932 ).
Structure
Thumb
Synonyms
ValueSource
(3E)-3-Penten-2-oneHMDB
(3E)-Pent-3-en-2-oneHMDB
2-oxo-3-PenteneHMDB
3-Penten-2-oneHMDB
3-Penten-2-one (methyl vinyl ketone)HMDB
Ethylidene acetoneHMDB
FEMA no. 3417HMDB
Methyl 1-propenyl ketoneHMDB
Pent-3-en-2-oneHMDB
Chemical FormulaC5H8O
Average Molecular Weight84.1164
Monoisotopic Molecular Weight84.057514878
IUPAC Name(3E)-pent-3-en-2-one
Traditional Name(E)-3-penten-2-one
CAS Registry Number625-33-2
SMILES
C\C=C\C(C)=O
InChI Identifier
InChI=1S/C5H8O/c1-3-4-5(2)6/h3-4H,1-2H3/b4-3+
InChI KeyInChIKey=LABTWGUMFABVFG-ONEGZZNKSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as enones. These are compounds containing the enone functional group, with the structure RC(=O)CR'.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbonyl compounds
Sub ClassAlpha,beta-unsaturated carbonyl compounds
Direct ParentEnones
Alternative Parents
Substituents
  • Enone
  • Acryloyl-group
  • Ketone
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point122.5 °CNot Available
Water SolubilityNot AvailableNot Available
LogP0.52HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility32.2 mg/mLALOGPS
logP1.48ALOGPS
logP1.25ChemAxon
logS-0.42ALOGPS
pKa (Strongest Acidic)19.86ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity26.52 m3·mol-1ChemAxon
Polarizability9.65 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)splash10-0159-9000000000-bc23095f98a3d62d8eddView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-39b3225b4599f0b9feceView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-ad93b895a094f9746ea9View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Feces
  • Saliva
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableChildren (1-13 years old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableChildren (1-13 years old)Not Specified
Treated celiac disease
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Campylobacter jejuni infection
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
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB008241
KNApSAcK IDNot Available
Chemspider ID553493
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01184
Metagene LinkHMDB01184
METLIN IDNot Available
PubChem Compound637920
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Zlatkis A, Liebich HM: Profile of volatile metabolites in human urine. Clin Chem. 1971 Jul;17(7):592-4. [5556886 ]
  2. Liebich HM, Woll J: Volatile substances in blood serum: profile analysis and quantitative determination. J Chromatogr. 1977 Nov 11;142:505-16. [914932 ]
  3. Chen L, Xie B, Yu T: [Identification of volatile compounds of hawthorn by gas chromatography/mass spectrometry (GC/MS)]. Se Pu. 1997 May;15(3):219-21. [15739361 ]
  4. Rock F, Mueller S, Weimar U, Rammensee HG, Overath P: Comparative analysis of volatile constituents from mice and their urine. J Chem Ecol. 2006 Jun;32(6):1333-46. Epub 2006 May 31. [16770722 ]