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Showing metabocard for Matairesinol (HMDB0035698)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-09-11 20:42:38 UTC
Update Date2020-11-09 23:20:34 UTC
HMDB IDHMDB0035698
Secondary Accession Numbers
  • HMDB0035789
  • HMDB35698
  • HMDB35789
Metabolite Identification
Common NameMatairesinol
DescriptionMatairesinol belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety. Matairesinol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, matairesinol is found, on average, in the highest concentration in a few different foods such as sesame, burdocks, and flaxseeds, and in a lower concentration in oats, asparagus, and poppies. Matairesinol has also been detected, but not quantified in, several different foods, such as silver lindens, tamarinds, cherry tomato, skunk currants, and fireweeds. This could make matairesinol a potential biomarker for the consumption of these foods. Matairesinol is composed of gamma-butyrolactone in which the 3 and 4 positions are substituted by 4-hydroxy-3-methoxybenzyl groups (the 3R,4R-diastereomer).
Structure
Data?1601223509
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3R,4R-Bis((4-hydroxy-3-methoxyphenyl)methyl)dihydro-2(3H)-furanoneChEBI
Artigenin congenerChEBI
MatairesinolChEBI
(3R,4R)-3,4-Bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-oneKegg
(8R,8'r)-(-)-MatairesinolHMDB
Dihydro-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-(3R,4R)-2(3H)-furanoneHMDB
Dihydro-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-(3R-trans)-2(3H)-furanoneHMDB
Matai-resinolHMDB
(-)-MatairesinolKEGG
(3R,4R)-Dihydro-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-2(3H)-furanoneHMDB
(8R,8’R)-(-)-MatairesinolHMDB
Dihydro-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-2(3H)-furanoneHMDB
Dihydro-3,4-divanillyl-2(3H)-furanonePhytoBank
Chemical FormulaC20H22O6
Average Molecular Weight358.3851
Monoisotopic Molecular Weight358.141638436
IUPAC Name(3R,4R)-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one
Traditional Namematairesinol
CAS Registry Number580-72-3
SMILES
COC1=C(O)C=CC(C[C@H]2COC(=O)[C@@H]2CC2=CC(OC)=C(O)C=C2)=C1
InChI Identifier
InChI=1S/C20H22O6/c1-24-18-9-12(3-5-16(18)21)7-14-11-26-20(23)15(14)8-13-4-6-17(22)19(10-13)25-2/h3-6,9-10,14-15,21-22H,7-8,11H2,1-2H3/t14-,15+/m0/s1
InChI KeyMATGKVZWFZHCLI-LSDHHAIUSA-N
Chemical Taxonomy
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
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point119 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.012 g/LALOGPS
logP2.79ALOGPS
logP3.29ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)9.64ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area85.22 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity95.63 m³·mol⁻¹ChemAxon
Polarizability36.86 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-0912000000-7b4af0e03073d528f059Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-052o-1050900000-0801cdc5bc6f2e25f382Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0229000000-da790a5b3ff80ab843dcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06ri-0978000000-407d81dd6dfadba216c4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ims-1910000000-060bdfec7823f760bd09Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-25c656431001e8e5785fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bt9-0129000000-eefe04935cde889de64cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ot-0986000000-2b1737e1ecb9a7ee39f9Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 595 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 595 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 595 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 595 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.00467 +/- 0.00933 umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified0.00400 +/- 0.00333 umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified0.0653 +/- 0.00867 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04200
Phenol Explorer Compound ID595
FooDB IDFDB014417
KNApSAcK IDC00000606
Chemspider ID106491
KEGG Compound IDC10682
BioCyc IDCPD-8912
BiGG IDNot Available
Wikipedia LinkMatairesinol
METLIN IDNot Available
PubChem Compound119205
PDB IDNot Available
ChEBI ID6698
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Muller U, Mrestani Y, Neubert R, Drager B: Chiral separation of the plant lignan matairesinol by capillary electrophoresis. Electrophoresis. 2008 Sep;29(17):3582-7. doi: 10.1002/elps.200700800. [PubMed:18803219 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .