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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:00:44 UTC
Update Date2022-03-07 02:55:52 UTC
HMDB IDHMDB0038677
Secondary Accession Numbers
  • HMDB38677
Metabolite Identification
Common NameAlfafuran
DescriptionAlfafuran belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. Alfafuran has been detected, but not quantified in, pulses. This could make alfafuran a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Alfafuran.
Structure
Data?1563863238
Synonyms
ValueSource
2-(3,5-Dihydroxyphenyl)-5,6-benzofurandiol, 9ciHMDB
Chemical FormulaC14H10O5
Average Molecular Weight258.2262
Monoisotopic Molecular Weight258.05282343
IUPAC Name2-(3,5-dihydroxyphenyl)-1-benzofuran-5,6-diol
Traditional Name2-(3,5-dihydroxyphenyl)-1-benzofuran-5,6-diol
CAS Registry Number156098-99-6
SMILES
OC1=CC(=CC(O)=C1)C1=CC2=C(O1)C=C(O)C(O)=C2
InChI Identifier
InChI=1S/C14H10O5/c15-9-1-7(2-10(16)5-9)13-4-8-3-11(17)12(18)6-14(8)19-13/h1-6,15-18H
InChI KeyFDARKUSEVNCTHK-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
  • Benzofuran
  • Resorcinol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Heteroaromatic compound
  • Furan
  • Oxacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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 Solubility748.1 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.69 g/LALOGPS
logP2.18ALOGPS
logP2.49ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)8.23ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area94.06 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity67.84 m³·mol⁻¹ChemAxon
Polarizability26.09 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]+160.87331661259
DarkChem[M-H]-160.2431661259
DeepCCS[M+H]+160.78830932474
DeepCCS[M-H]-158.4330932474
DeepCCS[M-2H]-191.31630932474
DeepCCS[M+Na]+166.88230932474
AllCCS[M+H]+157.532859911
AllCCS[M+H-H2O]+153.532859911
AllCCS[M+NH4]+161.232859911
AllCCS[M+Na]+162.332859911
AllCCS[M-H]-156.232859911
AllCCS[M+Na-2H]-155.432859911
AllCCS[M+HCOO]-154.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AlfafuranOC1=CC(=CC(O)=C1)C1=CC2=C(O1)C=C(O)C(O)=C25506.6Standard polar33892256
AlfafuranOC1=CC(=CC(O)=C1)C1=CC2=C(O1)C=C(O)C(O)=C22823.5Standard non polar33892256
AlfafuranOC1=CC(=CC(O)=C1)C1=CC2=C(O1)C=C(O)C(O)=C22932.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Alfafuran,1TMS,isomer #1C[Si](C)(C)OC1=CC(O)=CC(C2=CC3=CC(O)=C(O)C=C3O2)=C13030.4Semi standard non polar33892256
Alfafuran,1TMS,isomer #2C[Si](C)(C)OC1=CC2=C(C=C(C3=CC(O)=CC(O)=C3)O2)C=C1O2983.5Semi standard non polar33892256
Alfafuran,1TMS,isomer #3C[Si](C)(C)OC1=CC2=C(C=C1O)OC(C1=CC(O)=CC(O)=C1)=C22954.6Semi standard non polar33892256
Alfafuran,2TMS,isomer #1C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=CC(C2=CC3=CC(O)=C(O)C=C3O2)=C12984.0Semi standard non polar33892256
Alfafuran,2TMS,isomer #2C[Si](C)(C)OC1=CC(O)=CC(C2=CC3=CC(O[Si](C)(C)C)=C(O)C=C3O2)=C12911.5Semi standard non polar33892256
Alfafuran,2TMS,isomer #3C[Si](C)(C)OC1=CC(O)=CC(C2=CC3=CC(O)=C(O[Si](C)(C)C)C=C3O2)=C12944.9Semi standard non polar33892256
Alfafuran,2TMS,isomer #4C[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C)OC(C1=CC(O)=CC(O)=C1)=C22925.7Semi standard non polar33892256
Alfafuran,3TMS,isomer #1C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=CC(C2=CC3=CC(O[Si](C)(C)C)=C(O)C=C3O2)=C12907.9Semi standard non polar33892256
Alfafuran,3TMS,isomer #2C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=CC(C2=CC3=CC(O)=C(O[Si](C)(C)C)C=C3O2)=C12938.8Semi standard non polar33892256
Alfafuran,3TMS,isomer #3C[Si](C)(C)OC1=CC(O)=CC(C2=CC3=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C3O2)=C12807.7Semi standard non polar33892256
Alfafuran,4TMS,isomer #1C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=CC(C2=CC3=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C3O2)=C12894.9Semi standard non polar33892256
Alfafuran,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC(O)=CC(C2=CC3=CC(O)=C(O)C=C3O2)=C13312.6Semi standard non polar33892256
Alfafuran,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C(C3=CC(O)=CC(O)=C3)O2)C=C1O3294.7Semi standard non polar33892256
Alfafuran,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)OC(C1=CC(O)=CC(O)=C1)=C23268.3Semi standard non polar33892256
Alfafuran,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=CC(C2=CC3=CC(O)=C(O)C=C3O2)=C13568.6Semi standard non polar33892256
Alfafuran,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(O)=CC(C2=CC3=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C3O2)=C13540.5Semi standard non polar33892256
Alfafuran,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC(O)=CC(C2=CC3=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C3O2)=C13555.2Semi standard non polar33892256
Alfafuran,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)OC(C1=CC(O)=CC(O)=C1)=C23513.7Semi standard non polar33892256
Alfafuran,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=CC(C2=CC3=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C3O2)=C13667.2Semi standard non polar33892256
Alfafuran,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=CC(C2=CC3=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C3O2)=C13691.2Semi standard non polar33892256
Alfafuran,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC(O)=CC(C2=CC3=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C3O2)=C13648.9Semi standard non polar33892256
Alfafuran,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=CC(C2=CC3=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C3O2)=C13810.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Alfafuran GC-MS (Non-derivatized) - 70eV, Positivesplash10-05i0-0490000000-f6b4a2ad7747e4585d8e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Alfafuran GC-MS (4 TMS) - 70eV, Positivesplash10-00e9-3100930000-3e2986a9459248498e472017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Alfafuran 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 - Alfafuran 10V, Positive-QTOFsplash10-0a4i-0090000000-f47fbbdcb8abdccdc9012015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alfafuran 20V, Positive-QTOFsplash10-0a4i-0190000000-0e2839b5569ead598c0d2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alfafuran 40V, Positive-QTOFsplash10-0002-1940000000-d5aa461b36cd86abd3682015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alfafuran 10V, Negative-QTOFsplash10-0a4i-0090000000-5c422d91fb34b8101fb72015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alfafuran 20V, Negative-QTOFsplash10-0a4i-0090000000-5f5bfecda576b292b1232015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alfafuran 40V, Negative-QTOFsplash10-0ap1-1970000000-afce6e94408f5244ca882015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alfafuran 10V, Negative-QTOFsplash10-0a4i-0090000000-5c99e00473c8f7c5ab032021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alfafuran 20V, Negative-QTOFsplash10-0a4i-0090000000-a897e1b005c459453c942021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alfafuran 40V, Negative-QTOFsplash10-05g0-3950000000-d12014cc6dd1cc13dcf12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alfafuran 10V, Positive-QTOFsplash10-0a4i-0090000000-adb7dbccff647a6174612021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alfafuran 20V, Positive-QTOFsplash10-0a4i-0090000000-5a92fc864ed9849303b72021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alfafuran 40V, Positive-QTOFsplash10-0fki-0940000000-ea910d45d428d6a619972021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB018081
KNApSAcK IDC00055335
Chemspider ID30777285
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound90703276
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1870471
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.. .

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Alfafuran → 6-{[2-(3,5-dihydroxyphenyl)-6-hydroxy-1-benzofuran-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Alfafuran → 6-[3-(5,6-dihydroxy-1-benzofuran-2-yl)-5-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Alfafuran → 6-{[2-(3,5-dihydroxyphenyl)-5-hydroxy-1-benzofuran-6-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails