Showing metabocard for Tetrahydrofuran (BMDB0000246)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:27:20 UTC
Update Date2020-04-22 15:02:35 UTC
BMDB IDBMDB0000246
Secondary Accession Numbers
  • BMDB00246
Metabolite Identification
Common NameTetrahydrofuran
DescriptionTetrahydrofuran, also known as 1,4-epoxybutane or butylene oxide, belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen. Tetrahydrofuran exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
1,4-EpoxybutaneChEBI
Butane alpha,delta-oxideChEBI
Butylene oxideChEBI
FuranidineChEBI
Tetramethylene oxideChEBI
THFChEBI
Butane a,delta-oxideGenerator
Butane α,δ-oxideGenerator
Butane a,δ-oxideHMDB
1,4-Epoxy-butaneHMDB
Butane a,D-oxideHMDB
CyclotetramethyleneHMDB
Cyclotetramethylene oxideHMDB
Diethylene oxideHMDB
HydrofuranHMDB
OxacyclopentaneHMDB
OxolaneHMDB
PolytetrahydrofuranHMDB
TetrahydrofuraanHMDB
TetrahydrofuraneHMDB
TetrahydrofuranneHMDB
TetraidrofuranoHMDB
TetrahydrofuranChEBI
Chemical FormulaC4H8O
Average Molecular Weight72.1057
Monoisotopic Molecular Weight72.057514878
IUPAC Nameoxolane
Traditional Nametetrahydrofuran
CAS Registry Number109-99-9
SMILES
C1CCOC1
InChI Identifier
InChI=1S/C4H8O/c1-2-4-5-3-1/h1-4H2
InChI KeyWYURNTSHIVDZCO-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTetrahydrofurans
Sub ClassNot Available
Direct ParentTetrahydrofurans
Alternative Parents
Substituents
  • Tetrahydrofuran
  • Oxacycle
  • Ether
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-108.3 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000.0 mg/mLNot Available
LogP0.46HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP0.35ALOGPS
logP0.53ChemAxon
logS-0.01ALOGPS
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area9.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity20.55 m³·mol⁻¹ChemAxon
Polarizability8.14 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-15e25f01aff47ab7faccView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-5fecd52ae1047ea6ca80View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-a72cdfa78bc1624af6eeView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-15e25f01aff47ab7faccView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-5fecd52ae1047ea6ca80View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-a72cdfa78bc1624af6eeView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-9000000000-3a492c8c5b590a04fe86View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0ab9-9000000000-66253634d3f27573c6e6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0abc-9000000000-49362212e0db0e39a608View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00dl-9000000000-f307a5446840a5333e4fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0006-9000000000-15e25f01aff47ab7faccView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-0006-9000000000-5fecd52ae1047ea6ca80View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-0006-9000000000-a72cdfa78bc1624af6eeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-9000000000-57b4553c011e61c13302View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-633756c4cb26edc87875View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9000000000-f7f21b58e32e3bbdc8e8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-3191fdff289240be2d93View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-53ae58b025cd88229a02View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000f-9000000000-e2c11950e59178898ca9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-6f602d2adfd99a361876View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052f-9000000000-db869489a53547fd0e9aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-9000000000-e32b752db8542e7e4c7eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-9000000000-41ba71baeb0e935332bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-9000000000-4ffb3617277fb64e8592View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-4e009d20cbcc725a95e3View in MoNA
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000246
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021917
KNApSAcK IDC00010358
Chemspider ID7737
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTHF
METLIN IDNot Available
PubChem Compound8028
PDB IDNot Available
ChEBI ID26911
References
Synthesis ReferenceLi, Haixia; Yin, Hengbo; Jiang, Tingshun; Hu, Tongjie; Wu, Jing; Wada, Yuji. Cyclodehydration of 1,4-butanediol to tetrahydrofuran catalyzed by supported silicotungstic acid. Catalysis Communications (2006), 7(10), 778-782.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Antunes-Fernandes EC, van Gastelen S, Dijkstra J, Hettinga KA, Vervoort J: Milk metabolome relates enteric methane emission to milk synthesis and energy metabolism pathways. J Dairy Sci. 2016 Aug;99(8):6251-6262. doi: 10.3168/jds.2015-10248. Epub 2016 May 26. [PubMed:27236769 ]