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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:38:55 UTC
Update Date2019-07-23 06:07:15 UTC
HMDB IDHMDB0030768
Secondary Accession Numbers
  • HMDB30768
Metabolite Identification
Common Name2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran
Description2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran, also known as 2-benzofuranyl-3-methoxy-4,5-methylenedioxyphenol or 6-(2-benzofuranyl)-7-methoxy-1,3-benzodioxol-5-ol, 9CI, belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. 2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran has been detected, but not quantified in, cereals and cereal products. This could make 2-(6-hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran a potential biomarker for the consumption of these foods.
Structure
Data?1563862035
Synonyms
ValueSource
2-Benzofuranyl-3-methoxy-4,5-methylenedioxyphenolHMDB
6-(2-Benzofuranyl)-7-methoxy-1,3-benzodioxol-5-ol, 9ciHMDB
Chemical FormulaC16H12O5
Average Molecular Weight284.2635
Monoisotopic Molecular Weight284.068473494
IUPAC Name6-(1-benzofuran-2-yl)-7-methoxy-2H-1,3-benzodioxol-5-ol
Traditional Name6-(1-benzofuran-2-yl)-7-methoxy-2H-1,3-benzodioxol-5-ol
CAS Registry Number90996-89-7
SMILES
COC1=C(C2=CC3=CC=CC=C3O2)C(O)=CC2=C1OCO2
InChI Identifier
InChI=1S/C16H12O5/c1-18-16-14(10(17)7-13-15(16)20-8-19-13)12-6-9-4-2-3-5-11(9)21-12/h2-7,17H,8H2,1H3
InChI KeyACHFSGOIKJNVJV-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
  • Benzodioxole
  • Benzofuran
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Heteroaromatic compound
  • Furan
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point118 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.15 g/LALOGPS
logP3.04ALOGPS
logP2.86ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)8.92ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area61.06 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity74.12 m³·mol⁻¹ChemAxon
Polarizability29.03 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kai-1190000000-d3f912309ccfef752743Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-007o-7239000000-615e6fee44a136ebaa58Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-8a163de7f38e28e475d0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-0a95fe455860f0b5d375Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-2190000000-bf45eec5c0811130f146Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-800c6b79a1f5bd990a90Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0090000000-e074dfdae01df08fe202Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ffc-1290000000-491ad6a93b8233683c00Spectrum
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 IDFDB002703
KNApSAcK IDNot Available
Chemspider ID9066636
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10891372
PDB IDNot Available
ChEBI ID103729
Food Biomarker OntologyNot Available
VMH 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.. .

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
2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran → 6-{[6-(1-benzofuran-2-yl)-7-methoxy-2H-1,3-benzodioxol-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails