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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:38:55 UTC
Update Date2022-03-07 02:52:41 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. Based on a literature review very few articles have been published on 2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran.
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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point118 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+163.87331661259
DarkChem[M-H]-164.231661259
DeepCCS[M+H]+170.19530932474
DeepCCS[M-H]-167.83830932474
DeepCCS[M-2H]-200.72430932474
DeepCCS[M+Na]+176.28930932474
AllCCS[M+H]+164.232859911
AllCCS[M+H-H2O]+160.332859911
AllCCS[M+NH4]+167.832859911
AllCCS[M+Na]+168.832859911
AllCCS[M-H]-167.132859911
AllCCS[M+Na-2H]-166.132859911
AllCCS[M+HCOO]-165.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuranCOC1=C(C2=CC3=CC=CC=C3O2)C(O)=CC2=C1OCO23646.7Standard polar33892256
2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuranCOC1=C(C2=CC3=CC=CC=C3O2)C(O)=CC2=C1OCO22267.7Standard non polar33892256
2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuranCOC1=C(C2=CC3=CC=CC=C3O2)C(O)=CC2=C1OCO22542.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran,1TMS,isomer #1COC1=C2OCOC2=CC(O[Si](C)(C)C)=C1C1=CC2=CC=CC=C2O12631.8Semi standard non polar33892256
2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran,1TBDMS,isomer #1COC1=C2OCOC2=CC(O[Si](C)(C)C(C)(C)C)=C1C1=CC2=CC=CC=C2O12885.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kai-1190000000-d3f912309ccfef7527432016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran GC-MS (1 TMS) - 70eV, Positivesplash10-007o-7239000000-615e6fee44a136ebaa582017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran 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 - 2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran 10V, Positive-QTOFsplash10-000i-0090000000-8a163de7f38e28e475d02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran 20V, Positive-QTOFsplash10-000i-0090000000-0a95fe455860f0b5d3752016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran 40V, Positive-QTOFsplash10-0a4r-2190000000-bf45eec5c0811130f1462016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran 10V, Negative-QTOFsplash10-001i-0090000000-800c6b79a1f5bd990a902016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran 20V, Negative-QTOFsplash10-001i-0090000000-e074dfdae01df08fe2022016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran 40V, Negative-QTOFsplash10-0ffc-1290000000-491ad6a93b8233683c002016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran 10V, Positive-QTOFsplash10-000i-0090000000-edc9ea273e98ea6aa00a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran 20V, Positive-QTOFsplash10-000i-0090000000-005cd0acf791ae456fca2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran 40V, Positive-QTOFsplash10-05mo-2490000000-e11c768c8bf884ab37dc2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran 10V, Negative-QTOFsplash10-001i-0090000000-549f6b30f75977e8ff352021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran 20V, Negative-QTOFsplash10-001i-0390000000-5f15091431e0544a183e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran 40V, Negative-QTOFsplash10-0ul0-1290000000-2d37552d63c389935bd82021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-17Wishart 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 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
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.. .

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