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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:56:52 UTC
Update Date2022-03-07 02:56:57 UTC
HMDB IDHMDB0041276
Secondary Accession Numbers
  • HMDB41276
Metabolite Identification
Common Name(7'x,8'x)-4,7'-Epoxy-3,8'-bilign-7-ene-3,5'-dimethoxy-4',9,9'-triol
Description(7'x,8'x)-4,7'-Epoxy-3,8'-bilign-7-ene-3,5'-dimethoxy-4',9,9'-triol belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety (7'x,8'x)-4,7'-Epoxy-3,8'-bilign-7-ene-3,5'-dimethoxy-4',9,9'-triol has been detected, but not quantified in, several different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, green vegetables, and robusta coffees (Coffea canephora). This could make (7'X,8'X)-4,7'-epoxy-3,8'-bilign-7-ene-3,5'-dimethoxy-4',9,9'-triol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (7'x,8'x)-4,7'-Epoxy-3,8'-bilign-7-ene-3,5'-dimethoxy-4',9,9'-triol.
Structure
Data?1563863645
SynonymsNot Available
Chemical FormulaC20H22O6
Average Molecular Weight358.3851
Monoisotopic Molecular Weight358.141638436
IUPAC Name4-[3-(hydroxymethyl)-5-[(1Z)-3-hydroxyprop-1-en-1-yl]-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenol
Traditional Name4-[3-(hydroxymethyl)-5-[(1Z)-3-hydroxyprop-1-en-1-yl]-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenol
CAS Registry NumberNot Available
SMILES
COC1=CC(\C=C/CO)=CC2=C1OC(C2CO)C1=CC(OC)=C(O)C=C1
InChI Identifier
InChI=1S/C20H22O6/c1-24-17-10-13(5-6-16(17)23)19-15(11-22)14-8-12(4-3-7-21)9-18(25-2)20(14)26-19/h3-6,8-10,15,19,21-23H,7,11H2,1-2H3/b4-3-
InChI KeyKUSXBOZNRPQEON-ARJAWSKDSA-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
  • Neolignan skeleton
  • Methoxyphenol
  • Coumaran
  • Benzofuran
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Styrene
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • 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 SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.044 g/LALOGPS
logP2.28ALOGPS
logP1.83ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)9.91ChemAxon
pKa (Strongest Basic)-2.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area88.38 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity98.46 m³·mol⁻¹ChemAxon
Polarizability37.97 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+184.92131661259
DarkChem[M-H]-181.87331661259
DeepCCS[M+H]+184.38530932474
DeepCCS[M-H]-182.02830932474
DeepCCS[M-2H]-216.26930932474
DeepCCS[M+Na]+191.49730932474
AllCCS[M+H]+187.132859911
AllCCS[M+H-H2O]+184.032859911
AllCCS[M+NH4]+190.032859911
AllCCS[M+Na]+190.832859911
AllCCS[M-H]-188.632859911
AllCCS[M+Na-2H]-188.832859911
AllCCS[M+HCOO]-189.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(7'x,8'x)-4,7'-Epoxy-3,8'-bilign-7-ene-3,5'-dimethoxy-4',9,9'-triolCOC1=CC(\C=C/CO)=CC2=C1OC(C2CO)C1=CC(OC)=C(O)C=C14346.6Standard polar33892256
(7'x,8'x)-4,7'-Epoxy-3,8'-bilign-7-ene-3,5'-dimethoxy-4',9,9'-triolCOC1=CC(\C=C/CO)=CC2=C1OC(C2CO)C1=CC(OC)=C(O)C=C13147.8Standard non polar33892256
(7'x,8'x)-4,7'-Epoxy-3,8'-bilign-7-ene-3,5'-dimethoxy-4',9,9'-triolCOC1=CC(\C=C/CO)=CC2=C1OC(C2CO)C1=CC(OC)=C(O)C=C13305.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(7'x,8'x)-4,7'-Epoxy-3,8'-bilign-7-ene-3,5'-dimethoxy-4',9,9'-triol,1TMS,isomer #1COC1=CC(C2OC3=C(OC)C=C(/C=C\CO[Si](C)(C)C)C=C3C2CO)=CC=C1O3236.3Semi standard non polar33892256
(7'x,8'x)-4,7'-Epoxy-3,8'-bilign-7-ene-3,5'-dimethoxy-4',9,9'-triol,1TMS,isomer #2COC1=CC(C2OC3=C(OC)C=C(/C=C\CO)C=C3C2CO[Si](C)(C)C)=CC=C1O3212.4Semi standard non polar33892256
(7'x,8'x)-4,7'-Epoxy-3,8'-bilign-7-ene-3,5'-dimethoxy-4',9,9'-triol,1TMS,isomer #3COC1=CC(C2OC3=C(OC)C=C(/C=C\CO)C=C3C2CO)=CC=C1O[Si](C)(C)C3222.3Semi standard non polar33892256
(7'x,8'x)-4,7'-Epoxy-3,8'-bilign-7-ene-3,5'-dimethoxy-4',9,9'-triol,2TMS,isomer #1COC1=CC(C2OC3=C(OC)C=C(/C=C\CO[Si](C)(C)C)C=C3C2CO[Si](C)(C)C)=CC=C1O3162.9Semi standard non polar33892256
(7'x,8'x)-4,7'-Epoxy-3,8'-bilign-7-ene-3,5'-dimethoxy-4',9,9'-triol,2TMS,isomer #2COC1=CC(C2OC3=C(OC)C=C(/C=C\CO[Si](C)(C)C)C=C3C2CO)=CC=C1O[Si](C)(C)C3204.1Semi standard non polar33892256
(7'x,8'x)-4,7'-Epoxy-3,8'-bilign-7-ene-3,5'-dimethoxy-4',9,9'-triol,2TMS,isomer #3COC1=CC(C2OC3=C(OC)C=C(/C=C\CO)C=C3C2CO[Si](C)(C)C)=CC=C1O[Si](C)(C)C3175.8Semi standard non polar33892256
(7'x,8'x)-4,7'-Epoxy-3,8'-bilign-7-ene-3,5'-dimethoxy-4',9,9'-triol,3TMS,isomer #1COC1=CC(C2OC3=C(OC)C=C(/C=C\CO[Si](C)(C)C)C=C3C2CO[Si](C)(C)C)=CC=C1O[Si](C)(C)C3133.6Semi standard non polar33892256
(7'x,8'x)-4,7'-Epoxy-3,8'-bilign-7-ene-3,5'-dimethoxy-4',9,9'-triol,1TBDMS,isomer #1COC1=CC(C2OC3=C(OC)C=C(/C=C\CO[Si](C)(C)C(C)(C)C)C=C3C2CO)=CC=C1O3475.4Semi standard non polar33892256
(7'x,8'x)-4,7'-Epoxy-3,8'-bilign-7-ene-3,5'-dimethoxy-4',9,9'-triol,1TBDMS,isomer #2COC1=CC(C2OC3=C(OC)C=C(/C=C\CO)C=C3C2CO[Si](C)(C)C(C)(C)C)=CC=C1O3466.7Semi standard non polar33892256
(7'x,8'x)-4,7'-Epoxy-3,8'-bilign-7-ene-3,5'-dimethoxy-4',9,9'-triol,1TBDMS,isomer #3COC1=CC(C2OC3=C(OC)C=C(/C=C\CO)C=C3C2CO)=CC=C1O[Si](C)(C)C(C)(C)C3473.9Semi standard non polar33892256
(7'x,8'x)-4,7'-Epoxy-3,8'-bilign-7-ene-3,5'-dimethoxy-4',9,9'-triol,2TBDMS,isomer #1COC1=CC(C2OC3=C(OC)C=C(/C=C\CO[Si](C)(C)C(C)(C)C)C=C3C2CO[Si](C)(C)C(C)(C)C)=CC=C1O3651.4Semi standard non polar33892256
(7'x,8'x)-4,7'-Epoxy-3,8'-bilign-7-ene-3,5'-dimethoxy-4',9,9'-triol,2TBDMS,isomer #2COC1=CC(C2OC3=C(OC)C=C(/C=C\CO[Si](C)(C)C(C)(C)C)C=C3C2CO)=CC=C1O[Si](C)(C)C(C)(C)C3672.4Semi standard non polar33892256
(7'x,8'x)-4,7'-Epoxy-3,8'-bilign-7-ene-3,5'-dimethoxy-4',9,9'-triol,2TBDMS,isomer #3COC1=CC(C2OC3=C(OC)C=C(/C=C\CO)C=C3C2CO[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C3656.2Semi standard non polar33892256
(7'x,8'x)-4,7'-Epoxy-3,8'-bilign-7-ene-3,5'-dimethoxy-4',9,9'-triol,3TBDMS,isomer #1COC1=CC(C2OC3=C(OC)C=C(/C=C\CO[Si](C)(C)C(C)(C)C)C=C3C2CO[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C3836.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (7'x,8'x)-4,7'-Epoxy-3,8'-bilign-7-ene-3,5'-dimethoxy-4',9,9'-triol GC-MS (Non-derivatized) - 70eV, Positivesplash10-004l-0109000000-2bbcb76286e826ebd3af2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (7'x,8'x)-4,7'-Epoxy-3,8'-bilign-7-ene-3,5'-dimethoxy-4',9,9'-triol GC-MS (3 TMS) - 70eV, Positivesplash10-0bt9-3000290000-47b7b1d0d5394beb22282017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (7'x,8'x)-4,7'-Epoxy-3,8'-bilign-7-ene-3,5'-dimethoxy-4',9,9'-triol 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 - (7'x,8'x)-4,7'-Epoxy-3,8'-bilign-7-ene-3,5'-dimethoxy-4',9,9'-triol 10V, Positive-QTOFsplash10-052f-0009000000-122b0b8c17fca809102d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (7'x,8'x)-4,7'-Epoxy-3,8'-bilign-7-ene-3,5'-dimethoxy-4',9,9'-triol 20V, Positive-QTOFsplash10-006x-1219000000-6df6b94e734c3919956d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (7'x,8'x)-4,7'-Epoxy-3,8'-bilign-7-ene-3,5'-dimethoxy-4',9,9'-triol 40V, Positive-QTOFsplash10-0pi9-0910000000-0946685269d4b142ae2a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (7'x,8'x)-4,7'-Epoxy-3,8'-bilign-7-ene-3,5'-dimethoxy-4',9,9'-triol 10V, Negative-QTOFsplash10-0a4i-0009000000-e10df63170e4461926f52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (7'x,8'x)-4,7'-Epoxy-3,8'-bilign-7-ene-3,5'-dimethoxy-4',9,9'-triol 20V, Negative-QTOFsplash10-08i0-0019000000-86fd845cf9467a9bdaed2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (7'x,8'x)-4,7'-Epoxy-3,8'-bilign-7-ene-3,5'-dimethoxy-4',9,9'-triol 40V, Negative-QTOFsplash10-03di-0597000000-99f2c894904d2a629ced2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (7'x,8'x)-4,7'-Epoxy-3,8'-bilign-7-ene-3,5'-dimethoxy-4',9,9'-triol 10V, Negative-QTOFsplash10-0a4i-0009000000-ed8c7ebe000c2d7a9ea12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (7'x,8'x)-4,7'-Epoxy-3,8'-bilign-7-ene-3,5'-dimethoxy-4',9,9'-triol 20V, Negative-QTOFsplash10-08fr-0029000000-73e976f9a052e7a1c6392021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (7'x,8'x)-4,7'-Epoxy-3,8'-bilign-7-ene-3,5'-dimethoxy-4',9,9'-triol 40V, Negative-QTOFsplash10-0aor-0379000000-8a6c2cca652c3b6a7f0f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (7'x,8'x)-4,7'-Epoxy-3,8'-bilign-7-ene-3,5'-dimethoxy-4',9,9'-triol 10V, Positive-QTOFsplash10-0a4l-0009000000-0463a29e7460445a45ef2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (7'x,8'x)-4,7'-Epoxy-3,8'-bilign-7-ene-3,5'-dimethoxy-4',9,9'-triol 20V, Positive-QTOFsplash10-08fu-0019000000-ca44df6a478b69990e0c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (7'x,8'x)-4,7'-Epoxy-3,8'-bilign-7-ene-3,5'-dimethoxy-4',9,9'-triol 40V, Positive-QTOFsplash10-03di-0259000000-d5d1d2cfd2d3249ef0432021-09-24Wishart 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 IDFDB021188
KNApSAcK IDNot Available
Chemspider ID35015142
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131753094
PDB IDNot Available
ChEBI ID175608
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.. .