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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-05-18 14:35:56 UTC
Update Date2018-05-20 20:23:47 UTC
HMDB IDHMDB0013785
Secondary Accession Numbers
  • HMDB13785
Metabolite Identification
Common NameFuran
DescriptionFuran is a colorless, flammable, highly volatile liquid with a boiling point close to room temperature. It is soluble in common organic solvents, including alcohol, ether and acetone, but is insoluble in water. It is toxic and may be carcinogenic. Furan is used as a starting point to other specialty chemicals. Furan is a heterocyclic organic compound, consisting of a five-membered aromatic ring with four carbon atoms and one oxygen. The class of compounds containing such rings are also referred to as furans. Furan is aromatic because one of the lone pairs of electrons on the oxygen atom is delocalized into the ring, creating a 4n+2 aromatic system (see Huckel's rule) similar to benzene. Because of the aromaticity, the molecule is flat and lacks discrete double bonds. The other lone pair of electrons of the oxygen atom extends in the plane of the flat ring system. The sp2 hybridization is to allow one of the lone pairs of oxygen to reside in a p orbital and thus allow it to interact within the pi-system. The Feist-Benary synthesis is a classic way to synthesize furans, although many syntheses have been developed. One of the simplest synthesis methods for furans is the reaction of 1,4-diketones with phosphorus pentoxide (P2O5) in the Paal-Knorr Synthesis. The thiophene formation reaction of 1,4-diketones with Lawesson's reagent also forms furans as side products. 2,4-Disubstituted furans can be synthesized by sulfone-mediated cyclization of 1,3-diketones
Structure
Thumb
Synonyms
ValueSource
1,4-Epoxy-1,3-butadieneChEBI
Divinylene oxideChEBI
FuraneChEBI
OxacyclopentadieneChEBI
OxoleChEBI
TetroleChEBI
1-alpha-D-Glucopyranosyl-2-beta-D-fructofuranosideHMDB
FurfuranHMDB
FurfuraneHMDB
NitrofurantoinHMDB
Chemical FormulaC4H4O
Average Molecular Weight68.074
Monoisotopic Molecular Weight68.02621475
IUPAC Namefuran
Traditional Namefuran
CAS Registry Number110-00-9
SMILES
O1C=CC=C1
InChI Identifier
InChI=1S/C4H4O/c1-2-4-5-3-1/h1-4H
InChI KeyYLQBMQCUIZJEEH-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
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Source:

Role

Indirect biological role:

Environmental role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-85.6 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility10 mg/mL at 25 °CNot Available
LogP1.34Not Available
Predicted Properties
PropertyValueSource
Water Solubility15.9 g/LALOGPS
logP1.24ALOGPS
logP1.11ChemAxon
logS-0.63ALOGPS
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area13.14 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity18.57 m³·mol⁻¹ChemAxon
Polarizability6.68 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kr-9000000000-4c50652f33a401ab3caeView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kr-9000000000-d007e0256578ac930b22View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kr-9000000000-4c50652f33a401ab3caeView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kr-9000000000-d007e0256578ac930b22View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-9000000000-511af11e910184693aa1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9000000000-fd05695071ee559e9be4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9000000000-208e5dd03db999e390ffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-9000000000-351aa9d338efe69d31efView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-9000000000-acebecda0e70274875b1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9000000000-1df91dbb0164452d0fd1View in MoNA
MSMass Spectrum (Electron Ionization)splash10-00kr-9000000000-3bddc12b5a8dd3ca188dView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)BothNormal details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    UrineDetected but not Quantified Adult (>18 years old)BothNormal details
    Abnormal Concentrations
    BiospecimenStatusValueAgeSexConditionReferenceDetails
    FecesDetected but not Quantified Adult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) non progressor details
    FecesDetected but not Quantified Adult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) progressor details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Ulcerative colitis
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Crohn's disease
    details
    UrineDetected but not Quantified Adult (>18 years old)BothBreast cancer details
    Associated Disorders and Diseases
    Disease References
    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 ]
    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 ]
    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 ]
    Associated OMIM IDs
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FoodDB IDNot Available
    KNApSAcK IDNot Available
    Chemspider ID5768
    KEGG Compound IDC14275
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkFuran
    METLIN IDNot Available
    PubChem Compound5988
    PDB IDSUC
    ChEBI ID35559
    References
    Synthesis ReferenceNot Available
    Material Safety Data Sheet (MSDS)Download (PDF)
    General ReferencesNot Available