Record Information
Version1.0
Creation date2010-04-08 22:04:31 UTC
Update date2019-11-26 02:54:38 UTC
Primary IDFDB000326
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameIsohydroxymatairesinol
DescriptionIsohydroxymatairesinol is a member of the class of compounds known as lignan lactones. Lignan lactones are lignans that contain a lactone moiety. They include 1-aryltetralin lactones, dibenzylbutyrolactone lignans, and podophyllotoxins, among others. Isohydroxymatairesinol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Isohydroxymatairesinol can be found in sesame, which makes isohydroxymatairesinol a potential biomarker for the consumption of this food product.
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
(+)-Isohydroxymatairesinolbiospider
Predicted Properties
PropertyValueSource
Water Solubility0.032 g/LALOGPS
logP2.06ALOGPS
logP2.1ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)9.63ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area105.45 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity97.05 m³·mol⁻¹ChemAxon
Polarizability38.6 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC20H22O7
IUPAC name(3R,4R,5S)-5-(4-hydroxy-3-methoxyphenyl)-3-[(4-hydroxy-3-methoxyphenyl)methyl]-4-(hydroxymethyl)oxolan-2-one
InChI IdentifierInChI=1S/C20H22O7/c1-25-17-8-11(3-5-15(17)22)7-13-14(10-21)19(27-20(13)24)12-4-6-16(23)18(9-12)26-2/h3-6,8-9,13-14,19,21-23H,7,10H2,1-2H3/t13-,14+,19-/m1/s1
InChI KeyBTXZSJTULWTSJG-BIENJYKASA-N
Isomeric SMILES[H][C@@]1(CO)[C@H](OC(=O)[C@]1([H])CC1=CC(OC)=C(O)C=C1)C1=CC=C(O)C(OC)=C1
Average Molecular Weight374.3845
Monoisotopic Molecular Weight374.136553058
Classification
Description Belongs to the class of organic compounds known as lignan lactones. These are lignans that contain a lactone moiety. They include 1-aryltetralin lactones, dibenzylbutyrolactone lignans, and podophyllotoxins, among others.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassLignan lactones
Sub ClassNot Available
Direct ParentLignan lactones
Alternative Parents
Substituents
  • Lignan lactone
  • Tetrahydrofuran lignan
  • 7,9p-epoxylignan
  • Furanoid lignan
  • Methoxyphenol
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Methoxybenzene
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Gamma butyrolactone
  • Tetrahydrofuran
  • Lactone
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Ether
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Alcohol
  • Organooxygen compound
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organic oxygen compound
  • 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, Positivesplash10-056r-0109000000-8fdfb46434446663d777Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a70-0529000000-07e85b0ee937c81bf775Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002r-1910000000-16e82689c89c68f01645Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0009000000-9ea3506ca4ea84320faeSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05dl-0119000000-6c45a8fef6105a447bdcSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0201-1937000000-33f341855be397dd1580Spectrum
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 ID615
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 IDC00043617
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
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 Reference
  1. Eklund PC, Willfor SM, Smeds AI, Sundell FJ, Sjoholm RE, Holmbom BR: A new lariciresinol-type butyrolactone lignan derived from hydroxymatairesinol and its identification in spruce wood. J Nat Prod. 2004 Jun;67(6):927-31. Pubmed [Structure]
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.