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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:38:05 UTC
Update Date2022-03-07 02:52:38 UTC
HMDB IDHMDB0030635
Secondary Accession Numbers
  • HMDB30635
Metabolite Identification
Common Namealpha-Pyrufuran
Descriptionalpha-Pyrufuran, also known as α-pyrufuran, belongs to the class of organic compounds known as dibenzofurans. Dibenzofurans are compounds containing a dibenzofuran moiety, which consists of two benzene rings fused to a central furan ring. alpha-Pyrufuran has been detected, but not quantified in, pears (Pyrus communis) and pomes. This could make alpha-pyrufuran a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on alpha-Pyrufuran.
Structure
Data?1563862015
Synonyms
ValueSource
1,3,4-Trimethoxy-2-dibenzofuranolKegg
a-PyrufuranGenerator
Α-pyrufuranGenerator
1,3,4-Trimethoxy-2-dibenzofuranol, 9ciHMDB
1,3,4-Trimethoxydibenzofuran-2-olHMDB
Chemical FormulaC15H14O5
Average Molecular Weight274.2687
Monoisotopic Molecular Weight274.084123558
IUPAC Name3,5,6-trimethoxy-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(13),2,4,6,9,11-hexaen-4-ol
Traditional Nameα-pyrufuran
CAS Registry Number88256-05-7
SMILES
COC1=C2OC3=CC=CC=C3C2=C(OC)C(O)=C1OC
InChI Identifier
InChI=1S/C15H14O5/c1-17-12-10-8-6-4-5-7-9(8)20-13(10)15(19-3)14(18-2)11(12)16/h4-7,16H,1-3H3
InChI KeyLZNMTWGKSPOPIR-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dibenzofurans. Dibenzofurans are compounds containing a dibenzofuran moiety, which consists of two benzene rings fused to a central furan ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzofurans
Sub ClassDibenzofurans
Direct ParentDibenzofurans
Alternative Parents
Substituents
  • Dibenzofuran
  • Anisole
  • Alkyl aryl ether
  • Benzenoid
  • Heteroaromatic compound
  • Furan
  • Oxacycle
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP2.53ALOGPS
logP2.37ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)7.65ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area61.06 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity72.6 m³·mol⁻¹ChemAxon
Polarizability28.18 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+164.05331661259
DarkChem[M-H]-162.98531661259
DeepCCS[M+H]+161.97930932474
DeepCCS[M-H]-159.62130932474
DeepCCS[M-2H]-192.50730932474
DeepCCS[M+Na]+168.07230932474
AllCCS[M+H]+161.232859911
AllCCS[M+H-H2O]+157.532859911
AllCCS[M+NH4]+164.732859911
AllCCS[M+Na]+165.732859911
AllCCS[M-H]-165.432859911
AllCCS[M+Na-2H]-164.932859911
AllCCS[M+HCOO]-164.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
alpha-PyrufuranCOC1=C2OC3=CC=CC=C3C2=C(OC)C(O)=C1OC3708.0Standard polar33892256
alpha-PyrufuranCOC1=C2OC3=CC=CC=C3C2=C(OC)C(O)=C1OC2305.3Standard non polar33892256
alpha-PyrufuranCOC1=C2OC3=CC=CC=C3C2=C(OC)C(O)=C1OC2284.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
alpha-Pyrufuran,1TMS,isomer #1COC1=C(O[Si](C)(C)C)C(OC)=C2C(=C1OC)OC1=CC=CC=C122481.3Semi standard non polar33892256
alpha-Pyrufuran,1TBDMS,isomer #1COC1=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2C(=C1OC)OC1=CC=CC=C122689.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Pyrufuran GC-MS (Non-derivatized) - 70eV, Positivesplash10-0597-0090000000-44e1fb82ab9f1f669ac32017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Pyrufuran GC-MS (1 TMS) - 70eV, Positivesplash10-0ff0-3049000000-4e7d62db511e58e64c4b2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Pyrufuran GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Pyrufuran 10V, Positive-QTOFsplash10-004i-0090000000-0cb243d4765f56614cdb2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Pyrufuran 20V, Positive-QTOFsplash10-004i-0090000000-e1a382772a5d721312be2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Pyrufuran 40V, Positive-QTOFsplash10-056r-0390000000-23f43d34e2704dbb2b012016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Pyrufuran 10V, Negative-QTOFsplash10-00di-0090000000-e8e75c32b802d19a56a32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Pyrufuran 20V, Negative-QTOFsplash10-00di-0090000000-2f91a40165831372563f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Pyrufuran 40V, Negative-QTOFsplash10-0a70-1970000000-89096d17164806fc7c252016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Pyrufuran 10V, Positive-QTOFsplash10-004i-0090000000-369e429e4458b56edc5e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Pyrufuran 20V, Positive-QTOFsplash10-004i-0090000000-369e429e4458b56edc5e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Pyrufuran 40V, Positive-QTOFsplash10-0hg9-1940000000-51597c4995ce96941c0d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Pyrufuran 10V, Negative-QTOFsplash10-00di-0090000000-7dbb1e549f6404042b702021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Pyrufuran 20V, Negative-QTOFsplash10-00di-0090000000-9e077557cc523d7ec79d2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Pyrufuran 40V, Negative-QTOFsplash10-000i-3960000000-ed7ad808e66099faf7a22021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
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
FooDB IDFDB002539
KNApSAcK IDC00004037
Chemspider ID140054
KEGG Compound IDC08929
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10255010
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents 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.. .