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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:42:51 UTC
Update Date2022-03-07 02:53:54 UTC
HMDB IDHMDB0033940
Secondary Accession Numbers
  • HMDB33940
Metabolite Identification
Common NameVignafuran
DescriptionVignafuran belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. Thus, vignafuran is considered to be a flavonoid. Vignafuran has been detected, but not quantified in, a few different foods, such as cowpeas (Vigna unguiculata), hyacinth beans (Lablab purpureus), and pulses. This could make vignafuran a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Vignafuran.
Structure
Data?1563862484
Synonyms
ValueSource
2-(4-Hydroxy-2-methoxyphenyl)-6-methoxybenzofuranHMDB
Chemical FormulaC16H14O4
Average Molecular Weight270.28
Monoisotopic Molecular Weight270.089208936
IUPAC Name3-methoxy-4-(6-methoxy-1-benzofuran-2-yl)phenol
Traditional Namevignafuran
CAS Registry Number57800-41-6
SMILES
COC1=CC2=C(C=C(O2)C2=C(OC)C=C(O)C=C2)C=C1
InChI Identifier
InChI=1S/C16H14O4/c1-18-12-5-3-10-7-16(20-14(10)9-12)13-6-4-11(17)8-15(13)19-2/h3-9,17H,1-2H3
InChI KeyYCDZKMJZSGRQML-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
Class2-arylbenzofuran flavonoids
Sub ClassNot Available
Direct Parent2-arylbenzofuran flavonoids
Alternative Parents
Substituents
  • 2-arylbenzofuran flavonoid
  • 2-phenylbenzofuran
  • Phenylbenzofuran
  • Methoxyphenol
  • Benzofuran
  • Phenoxy compound
  • Anisole
  • Phenol ether
  • Methoxybenzene
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Heteroaromatic compound
  • Furan
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility27.39 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.05 g/LALOGPS
logP3.75ALOGPS
logP3.08ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)9.02ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area51.83 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity74.82 m³·mol⁻¹ChemAxon
Polarizability28.93 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]+163.35731661259
DarkChem[M-H]-167.15631661259
DeepCCS[M+H]+168.6230932474
DeepCCS[M-H]-166.26230932474
DeepCCS[M-2H]-199.14830932474
DeepCCS[M+Na]+174.71430932474
AllCCS[M+H]+162.232859911
AllCCS[M+H-H2O]+158.332859911
AllCCS[M+NH4]+165.932859911
AllCCS[M+Na]+166.932859911
AllCCS[M-H]-165.432859911
AllCCS[M+Na-2H]-164.832859911
AllCCS[M+HCOO]-164.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
VignafuranCOC1=CC2=C(C=C(O2)C2=C(OC)C=C(O)C=C2)C=C13919.0Standard polar33892256
VignafuranCOC1=CC2=C(C=C(O2)C2=C(OC)C=C(O)C=C2)C=C12439.5Standard non polar33892256
VignafuranCOC1=CC2=C(C=C(O2)C2=C(OC)C=C(O)C=C2)C=C12632.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Vignafuran,1TMS,isomer #1COC1=CC=C2C=C(C3=CC=C(O[Si](C)(C)C)C=C3OC)OC2=C12648.1Semi standard non polar33892256
Vignafuran,1TBDMS,isomer #1COC1=CC=C2C=C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3OC)OC2=C12889.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Vignafuran GC-MS (Non-derivatized) - 70eV, Positivesplash10-05du-0290000000-678fa416099de46093ce2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vignafuran GC-MS (1 TMS) - 70eV, Positivesplash10-00b9-4389000000-5d90f43e105e7f56d4172017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vignafuran 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 - Vignafuran 10V, Positive-QTOFsplash10-00di-0090000000-71534b7080646d7d8e9d2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vignafuran 20V, Positive-QTOFsplash10-00di-0090000000-8185285362e1affaba282015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vignafuran 40V, Positive-QTOFsplash10-07ko-2390000000-980b6e9eeee3c2e9215a2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vignafuran 10V, Negative-QTOFsplash10-014i-0090000000-1acc694e6728a2a1b3862015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vignafuran 20V, Negative-QTOFsplash10-014i-0090000000-8ade677fac31f22d914b2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vignafuran 40V, Negative-QTOFsplash10-014r-3970000000-735d4798d1e49e43da9e2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vignafuran 10V, Positive-QTOFsplash10-00di-0090000000-cfedaa36beb9531942222021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vignafuran 20V, Positive-QTOFsplash10-00di-0190000000-b164076d107beec6645d2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vignafuran 40V, Positive-QTOFsplash10-000i-0960000000-c1f5d997a58e56fc15a52021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vignafuran 10V, Negative-QTOFsplash10-014i-0090000000-6871b36f9793cdefd0192021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vignafuran 20V, Negative-QTOFsplash10-014i-0090000000-fba2c953c1b5684b0df02021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vignafuran 40V, Negative-QTOFsplash10-00fs-1890000000-181613c5abe83e7a62282021-09-25Wishart 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 IDFDB012147
KNApSAcK IDC00002414
Chemspider ID390527
KEGG Compound IDC08993
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound441958
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1839391
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.. .