Record Information
Version1.0
Creation date2010-04-08 22:04:31 UTC
Update date2019-11-26 02:54:38 UTC
Primary IDFDB000325
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name7-Hydroxymatairesinol
Description7-hydroxymatairesinol is a member of the class of compounds known as dibenzylbutyrolactone lignans. Dibenzylbutyrolactone lignans are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety. 7-hydroxymatairesinol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 7-hydroxymatairesinol can be found in sesame, which makes 7-hydroxymatairesinol a potential biomarker for the consumption of this food product. Hydroxymatairesinol (HMR) is a lignan found in Norway spruce (Picea abies). It is an enterolactone precursor with anticancer activities. In rats, HMR decreased the volume of induced tumours and stabilised established tumours, as well as preventing the development of new tumours. It has also shown anti-oxidant properties in vitro .
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
(-)-7-Hydroxymatairesinolbiospider
Predicted Properties
PropertyValueSource
Water Solubility0.037 g/LALOGPS
logP2ALOGPS
logP2.22ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)9.63ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area105.45 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity97 m³·mol⁻¹ChemAxon
Polarizability38.32 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC20H22O7
IUPAC name(4R)-3-[(S)-hydroxy(4-hydroxy-3-methoxyphenyl)methyl]-4-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one
InChI IdentifierInChI=1S/C20H22O7/c1-25-16-8-11(3-5-14(16)21)7-13-10-27-20(24)18(13)19(23)12-4-6-15(22)17(9-12)26-2/h3-6,8-9,13,18-19,21-23H,7,10H2,1-2H3/t13-,18?,19+/m0/s1
InChI KeyZZSOKNNVDKKSDE-LPHKOSDUSA-N
Isomeric SMILESCOC1=CC(C[C@H]2COC(=O)C2[C@H](O)C2=CC=C(O)C(OC)=C2)=CC=C1O
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
  • Benzenoid
  • Gamma butyrolactone
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Lactone
  • Secondary alcohol
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Aromatic alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pdi-0319000000-2aa39a15834561e84a07Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0936000000-18196c525b66c5f784f4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0w29-1901000000-070fa63d30be923e3bf3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0029000000-01c9185eb76cc13701f0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05i0-0769000000-a71c0986d0d546e4d187Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fkl-1921000000-7932636a3c70c4735cc3Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID614
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 IDC00038321
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 ID614
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
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.