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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:02:02 UTC
Update Date2019-07-23 06:15:32 UTC
HMDB IDHMDB0034230
Secondary Accession Numbers
  • HMDB34230
Metabolite Identification
Common NameMesifurane
DescriptionMesifurane, also known as fema 3664 or O-methylfuraneol, belongs to the class of organic compounds known as furanones. Furanones are compounds containing a furan ring bearing a ketone group. Mesifurane is an extremely weak basic (essentially neutral) compound (based on its pKa). Mesifurane is a mildew, sweet, and caramel tasting compound. Outside of the human body, mesifurane has been detected, but not quantified in, fruits. This could make mesifurane a potential biomarker for the consumption of these foods.
Structure
Data?1563862532
Synonyms
ValueSource
2,5-Dimethyl 4-methoxy furan-3-oneHMDB
2,5-Dimethyl-4-methoxy-2,3-dihydro-3-furanoneHMDB
2,5-Dimethyl-4-methoxy-3(2H)-furanoneHMDB
3(2H)-Furanone, 2,5-dimethyl-4-methoxyHMDB
4-Methoxy-2,5-dimethyl-2,3-dihydrofuran-3-oneHMDB
4-Methoxy-2,5-dimethyl-3(2H)-furanoneHMDB
4-Methoxy-2,5-dimethylfuran-3(2H)-oneHMDB
FEMA 3664HMDB
MesifuranHMDB
O-MethylfuraneolHMDB
DMMF CPDHMDB
Chemical FormulaC7H10O3
Average Molecular Weight142.1525
Monoisotopic Molecular Weight142.062994186
IUPAC Name4-methoxy-2,5-dimethyl-2,3-dihydrofuran-3-one
Traditional Name4-methoxy-2,5-dimethyl-2H-furan-3-one
CAS Registry Number4077-47-8
SMILES
COC1=C(C)OC(C)C1=O
InChI Identifier
InChI=1S/C7H10O3/c1-4-6(8)7(9-3)5(2)10-4/h4H,1-3H3
InChI KeySIMKGHMLPVDSJE-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as furanones. Furanones are compounds containing a furan ring bearing a ketone group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDihydrofurans
Sub ClassFuranones
Direct ParentFuranones
Alternative Parents
Substituents
  • 3-furanone
  • Vinylogous ester
  • Cyclic ketone
  • Ketone
  • Oxacycle
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility152 g/LALOGPS
logP0.43ALOGPS
logP0.32ChemAxon
logS0.03ALOGPS
pKa (Strongest Acidic)8.18ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area35.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity38.04 m³·mol⁻¹ChemAxon
Polarizability14.38 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00xs-9100000000-70c7d96673888cf7153eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-96041d3e7b9e509669d3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-3900000000-f393b47f20abc98d8752Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05xv-9100000000-1530efdfde178d0c52aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1900000000-63bd61312fa748005768Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-597d2aedc6ce435c8b4bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gb9-9100000000-e762db83470b78aba435Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012541
KNApSAcK IDNot Available
Chemspider ID55261
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound61325
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .