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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-11 17:54:14 UTC
Update Date2022-03-07 02:53:37 UTC
HMDB IDHMDB0033182
Secondary Accession Numbers
  • HMDB33182
Metabolite Identification
Common Name2,5-Dimethylfuran
Description2,5-Dimethylfuran is a derivative of furan. It is a heterocyclic compound of the formula C6H8O. While it may be abbreviated DMF, it should not be confused with dimethylformamide. 2,5-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.Recent advances have increased its attractiveness as a biofuel.
Structure
Data?1563862364
Synonyms
ValueSource
2,5-Dimethyl-furanChEBI
2,5-DimethylfuraneChEBI
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 KeyGSNUFIFRDBKVIE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as heteroaromatic compounds. Heteroaromatic compounds 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
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-63 °CNot Available
Boiling Point92.00 to 94.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1466 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.24Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility7.55 g/LALOGPS
logP2.17ALOGPS
logP1.51ChemAxon
logS-1.1ALOGPS
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area13.14 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity28.87 m³·mol⁻¹ChemAxon
Polarizability11.09 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+117.72131661259
DarkChem[M-H]-113.97931661259
DeepCCS[M+H]+127.9230932474
DeepCCS[M-H]-125.91130932474
DeepCCS[M-2H]-161.52830932474
DeepCCS[M+Na]+136.18330932474
AllCCS[M+H]+115.332859911
AllCCS[M+H-H2O]+110.132859911
AllCCS[M+NH4]+120.232859911
AllCCS[M+Na]+121.632859911
AllCCS[M-H]-117.132859911
AllCCS[M+Na-2H]-120.132859911
AllCCS[M+HCOO]-123.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2,5-DimethylfuranCC1=CC=C(C)O1927.5Standard polar33892256
2,5-DimethylfuranCC1=CC=C(C)O1714.2Standard non polar33892256
2,5-DimethylfuranCC1=CC=C(C)O1700.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 2,5-Dimethylfuran EI-B (Non-derivatized)splash10-0f6w-9000000000-c4a1e868867e02296ecb2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,5-Dimethylfuran EI-B (Non-derivatized)splash10-0f6w-9000000000-c4a1e868867e02296ecb2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,5-Dimethylfuran GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9000000000-5541d1a8919494d09a972016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,5-Dimethylfuran GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0002-9000000000-654fd33daad26ad7f6de2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,5-Dimethylfuran 10V, Positive-QTOFsplash10-0002-9000000000-c1f5eca2bb55a34c65432015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,5-Dimethylfuran 20V, Positive-QTOFsplash10-0002-9000000000-5506ccbd7d54899cdf5b2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,5-Dimethylfuran 40V, Positive-QTOFsplash10-0udi-9000000000-e12a4cdc311091858f8c2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,5-Dimethylfuran 10V, Negative-QTOFsplash10-0002-9000000000-03aafe04d643341b91c12015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,5-Dimethylfuran 20V, Negative-QTOFsplash10-0002-9000000000-6c128c2cf7b062b9ad932015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,5-Dimethylfuran 40V, Negative-QTOFsplash10-0ftb-9000000000-efa612ea3a77b76d3d8d2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,5-Dimethylfuran 10V, Positive-QTOFsplash10-0fba-9000000000-c1e51a5940fb212770022021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,5-Dimethylfuran 20V, Positive-QTOFsplash10-0fba-9000000000-b4e0bd7ed39f1cbf2e1c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,5-Dimethylfuran 40V, Positive-QTOFsplash10-0ufr-9000000000-df50467e5f4359dae1872021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,5-Dimethylfuran 10V, Negative-QTOFsplash10-004i-9000000000-b50ddc91987bceb8c2b32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,5-Dimethylfuran 20V, Negative-QTOFsplash10-004i-9000000000-3baf92a782df3868fc982021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,5-Dimethylfuran 40V, Negative-QTOFsplash10-0ufv-9000000000-5f4efb78df2931d80f262021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000166 uMAdult (>18 years old)Not SpecifiedNormal
    • National Health a...
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative colitis
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Crohn's disease
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)FemaleBreast cancer details
Associated Disorders and Diseases
Disease References
Ulcerative colitis
  1. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
Crohn's disease
  1. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
Perillyl alcohol administration for cancer treatment
  1. Silva CL, Passos M, Camara JS: Solid phase microextraction, mass spectrometry and metabolomic approaches for detection of potential urinary cancer biomarkers--a powerful strategy for breast cancer diagnosis. Talanta. 2012 Jan 30;89:360-8. doi: 10.1016/j.talanta.2011.12.041. Epub 2011 Dec 22. [PubMed:22284503 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB011193
KNApSAcK IDNot Available
Chemspider ID11763
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2,5-Dimethylfuran
METLIN IDNot Available
PubChem Compound12266
PDB IDNot Available
ChEBI ID89052
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00029794
Good Scents IDrw1040081
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.. .