Record Information
Version1.0
Creation date2010-04-08 22:05:24 UTC
Update date2020-02-24 19:10:31 UTC
Primary IDFDB002492
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(-)-Wikstromol
Description(-)-Wikstromol belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety (-)-Wikstromol is found, on average, in the highest concentration within sesames (Sesamum orientale) (-)-Wikstromol has also been detected, but not quantified in, fruits. This could make (-)-wikstromol a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on (-)-Wikstromol.
CAS Number34444-37-6
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.028 g/LALOGPS
logP1.88ALOGPS
logP2.43ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)9.64ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area105.45 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity97.09 m³·mol⁻¹ChemAxon
Polarizability38.04 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC20H22O7
IUPAC name3-hydroxy-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one
InChI IdentifierInChI=1S/C20H22O7/c1-25-17-8-12(3-5-15(17)21)7-14-11-27-19(23)20(14,24)10-13-4-6-16(22)18(9-13)26-2/h3-6,8-9,14,21-22,24H,7,10-11H2,1-2H3
InChI KeyZITBJWXLODLDRH-UHFFFAOYSA-N
Isomeric SMILESCOC1=C(O)C=CC(CC2COC(=O)C2(O)CC2=CC(OC)=C(O)C=C2)=C1
Average Molecular Weight374.3845
Monoisotopic Molecular Weight374.136553058
Classification
Description Belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassFuranoid lignans
Sub ClassTetrahydrofuran lignans
Direct ParentDibenzylbutyrolactone lignans
Alternative Parents
Substituents
  • Dibenzylbutyrolactone
  • Lignan lactone
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Gamma butyrolactone
  • Benzenoid
  • Tetrahydrofuran
  • Tertiary alcohol
  • Carboxylic acid ester
  • Lactone
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(-)-Wikstromol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-0901000000-78e3c7cf8158232e1495Spectrum
Predicted GC-MS(-)-Wikstromol, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-003r-2031090000-c8fb8418fd6953dad145Spectrum
Predicted GC-MS(-)-Wikstromol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-000i-0930000000-fe78dc9c087a79e0d7982017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-00di-0119000000-2905fe9482c8ec5017ef2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-0930000000-fe78dc9c087a79e0d7982017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-0911000000-ec4863cd8d55422e9f762017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0319000000-dd9ef3e03c550e5f0ef22015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0946000000-6564c7dba5c7dc863e642015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p9-1900000000-f69fe05a373b7d4b49cf2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0319000000-dd9ef3e03c550e5f0ef22015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0946000000-6564c7dba5c7dc863e642015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p9-1900000000-f69fe05a373b7d4b49cf2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00dr-0079000000-9d1e94ab28622937cec52015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-0469000000-5e6c162ac7baf304061d2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ads-0954000000-b7b2e200baf1fb72d5532015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00dr-0079000000-9d1e94ab28622937cec52015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-0469000000-5e6c162ac7baf304061d2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ads-0954000000-b7b2e200baf1fb72d5532015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0409000000-eb78288de8a68839bc4f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-0921000000-357782c3854c3e65ee642021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1920000000-1a2efb46507e034975e72021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0019000000-419b539150dca3678a6a2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0229000000-0f88eecb98483341b7f92021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-1669000000-e5efde8fb414170b73372021-09-22View Spectrum
NMRNot Available
ChemSpider ID90295
ChEMBL IDNot Available
KEGG Compound IDC10725
Pubchem Compound ID99938
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID622
DrugBank IDNot Available
HMDB IDHMDB30598
CRC / DFC (Dictionary of Food Compounds) IDHHW00-Z:CMC32-U
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00000599
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.