Record Information
Version1.0
Creation date2010-04-08 22:04:58 UTC
Update date2019-11-26 02:56:28 UTC
Primary IDFDB001447
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameMedioresinol
DescriptionMedioresinol is a member of the class of compounds known as furanoid lignans. Furanoid lignans are lignans with a structure that contains either a tetrahydrofuran ring, a furan ring, or a furofuan ring system, that arises from the joining of the two phenylpropanoid units. Medioresinol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Medioresinol can be found in a number of food items such as garden tomato (variety), common buckwheat, radish (variety), and black elderberry, which makes medioresinol a potential biomarker for the consumption of these food products.
CAS Number40957-99-1
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.04 g/LALOGPS
logP2.26ALOGPS
logP2.12ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)9.21ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area86.61 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity101.56 m³·mol⁻¹ChemAxon
Polarizability39.43 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC21H24O7
IUPAC name4-[(1S,3aR,4S,6aR)-4-(4-hydroxy-3-methoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2,6-dimethoxyphenol
InChI IdentifierInChI=1S/C21H24O7/c1-24-16-6-11(4-5-15(16)22)20-13-9-28-21(14(13)10-27-20)12-7-17(25-2)19(23)18(8-12)26-3/h4-8,13-14,20-23H,9-10H2,1-3H3/t13-,14-,20+,21+/m0/s1
InChI KeyVJOBNGRIBLNUKN-BMHXQBNDSA-N
Isomeric SMILESCOC1=CC(=CC=C1O)[C@H]1OC[C@H]2[C@@H]1CO[C@@H]2C1=CC(OC)=C(O)C(OC)=C1
Average Molecular Weight388.4111
Monoisotopic Molecular Weight388.152203122
Classification
Description Belongs to the class of organic compounds known as furanoid lignans. These are lignans with a structure that contains either a tetrahydrofuran ring, a furan ring, or a furofuan ring system, that arises from the joining of the two phenylpropanoid units.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassFuranoid lignans
Sub ClassNot Available
Direct ParentFuranoid lignans
Alternative Parents
Substituents
  • Furanoid lignan
  • Furofuran lignan skeleton
  • Methoxyphenol
  • Dimethoxybenzene
  • M-dimethoxybenzene
  • Anisole
  • Phenoxy compound
  • Furofuran
  • Phenol ether
  • Methoxybenzene
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Tetrahydrofuran
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Dialkyl ether
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0119000000-5778011e2734e2f214bc2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-0079000000-a260e666eedb528efdb22016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-5900000000-33a5491b01091aac94012016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0109000000-67ceb767da2a1ff209052016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-0129000000-b9836e0621fc1b3473392016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zi3-1925000000-1097df9a963d6b03b5be2016-08-04View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID181681
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID602
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00000659
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.