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Record Information
Version3.6
Creation Date2012-09-11 17:54:14 UTC
Update Date2016-02-11 02:11:22 UTC
HMDB IDHMDB33182
Secondary Accession NumbersNone
Metabolite Identification
Common Name2,5-Dimethylfuran
Description2,5-Dimethylfuran is a maillard product 2,5-Dimethylfuran has been identified as one of the components of cigar smoke with low cilatoxicity (ability to adversely affect the cilia in the respiratory tract that are responsible for removing foreign particles). Its blood concentration can be used as a biomarker for smoking. 2,5-Dimethylfuran, together with 2,5-hexanedione and 4,5-dihydroxy-2-hexanone, is one of the main metabolites of hexane in humans, which play a role in the mechanism for the neurotoxicity of hexane. A derivative of furan, 2,5-dimethylfuran is a heterocyclic compound of the formula C6H8O. While it may be abbreviated DMF, it should not be confused with dimethylformamide. Recent advances have increased its attractiveness as a biofuel.
Structure
Thumb
Synonyms
ValueSource
2,5-Dimethyl-furanHMDB
2,5-DimethylfuraneHMDB
Chemical FormulaC6H8O
Average Molecular Weight96.1271
Monoisotopic Molecular Weight96.057514878
IUPAC Name2,5-dimethylfuran
Traditional Name2,5-dimethylfuran
CAS Registry Number625-86-5
SMILES
CC1=CC=C(C)O1
InChI Identifier
InChI=1S/C6H8O/c1-5-3-4-6(2)7-5/h3-4H,1-2H3
InChI KeyInChIKey=GSNUFIFRDBKVIE-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as heteroaromatic compounds. These are compounds containing an aromatic ring where a carbon atom is linked to an hetero atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassHeteroaromatic compounds
Sub ClassNot Available
Direct ParentHeteroaromatic compounds
Alternative Parents
Substituents
  • Heteroaromatic compound
  • Furan
  • Oxacycle
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Food
Biofunction
  • Nutrient
Application
  • Nutrient
Cellular locations
  • Cytoplasm
  • Extracellular
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point-63 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP2.24Not Available
Predicted Properties
PropertyValueSource
Water Solubility7.55 mg/mLALOGPS
logP2.17ALOGPS
logP1.51ChemAxon
logS-1.1ALOGPS
pKa (Strongest Basic)-2.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area13.14 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity28.87 m3·mol-1ChemAxon
Polarizability11.09 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-c1f5eca2bb55a34c6543View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-5506ccbd7d54899cdf5bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9000000000-e12a4cdc311091858f8cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-03aafe04d643341b91c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9000000000-6c128c2cf7b062b9ad93View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ftb-9000000000-efa612ea3a77b76d3d8dView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0002-9000000000-654fd33daad26ad7f6deView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000166 uMAdult (>18 years old)Not SpecifiedNormal
    • National Health a...
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Campylobacter jejuni infection
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)FemaleBreast cancer 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 IDFDB011193
KNApSAcK IDNot Available
Chemspider ID11763
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2,5-Dimethylfuran
NuGOwiki LinkHMDB33182
Metagene LinkHMDB33182
METLIN IDNot Available
PubChem Compound12266
PDB IDNot Available
ChEBI 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.