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Showing Compound (-)-Matairesinol (FDB014417)

Record Information
Version1.0
Creation date2010-04-08 22:11:15 UTC
Update date2019-11-26 03:10:00 UTC
Primary IDFDB014417
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(-)-Matairesinol
Description(-)-Matairesinol belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring (-)-Matairesinol is an extremely weak basic (essentially neutral) compound (based on its pKa) (-)-Matairesinol is found, on average, in the highest concentration within a few different foods, such as sesames, burdocks, and flaxseeds and in a lower concentration in radish (var.), grape wines, and miso (-)-Matairesinol has also been detected, but not quantified in, several different foods, such as cardamoms, canada blueberries, beans, arctic blackberries, and kelps. This could make (-)-matairesinol a potential biomarker for the consumption of these foods.
CAS Number580-72-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(-)-Matairesinolbiospider
(8R,8'R)-(-)-Matairesinolmanual
2(3H)-Furanone, dihydro-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-, (3R-trans)-manual
2(3H)-Furanone, dihydro-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-, (3R,4R)-manual
3R,4R-Bis((4-hydroxy-3-methoxyphenyl)methyl)dihydro-2(3H)-furanoneChEBI
Artigenin congenerChEBI
dihydro-3,4-Bis[(4-hydroxy-3-methoxyphenyl)methyl]-(3R-trans)-2(3H)-furanoneHMDB
dihydro-3,4-Bis[(4-hydroxy-3-methoxyphenyl)methyl]-(3R,4R)-2(3H)-furanoneHMDB
MatairesinolChEBI
Predicted Properties
PropertyValueSource
Water Solubility0.09 g/LALOGPS
logP2.08ALOGPS
logP1.51ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)13.9ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area85.22 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity96.42 m³·mol⁻¹ChemAxon
Polarizability41.22 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC20H34O6
IUPAC name3,4-bis[(4-hydroxy-3-methoxycyclohexyl)methyl]oxolan-2-one
InChI IdentifierInChI=1S/C20H34O6/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/h12-19,21-22H,3-11H2,1-2H3
InChI KeyARQURIMKGVUGBH-UHFFFAOYSA-N
Isomeric SMILESCOC1CC(CC2COC(=O)C2CC2CCC(O)C(C2)OC)CCC1O
Average Molecular Weight370.486
Monoisotopic Molecular Weight370.235538815
Classification
Description Belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentCyclohexanols
Alternative Parents
Substituents
  • Cyclohexanol
  • Gamma butyrolactone
  • Cyclic alcohol
  • Tetrahydrofuran
  • Lactone
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Oxacycle
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 67.03%; H 6.19%; O 26.79%DFC
Melting PointMp 119° (anhyd.)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -40 (c, 0.1 in EtOH)DFC
Spectroscopic UV Data280 () (EtOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0119000000-ae72af1af4f3cfa6528c2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uxu-0596000000-99bed884feb6e3715ddc2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fr7-6960000000-5b62d3b5ac51ccd551fd2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-8304813b564f8cb08e8a2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fvi-0119000000-229bd20dbf53c370dde92015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aba-1936000000-bf6ea59c6a4c08f732d42015-05-27View Spectrum
NMRNot Available
ChemSpider ID106491
ChEMBL IDCHEMBL425148
KEGG Compound IDC10682
Pubchem Compound ID119205
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID595
DrugBank IDDB04200
HMDB IDHMDB35698
CRC / DFC (Dictionary of Food Compounds) IDJRV93-M:JQK13-E
EAFUS IDNot Available
Dr. Duke IDMATAIRESINOL|MATIRESINOL
BIGG IDNot Available
KNApSAcK IDC00000606
HET IDMAX
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDMatairesinol
Phenol-Explorer Metabolite ID595
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
Anti leukemic35610 An agent that targets and inhibits the growth of leukemia cells, playing a crucial role in cancer treatment. Therapeutically, it is used to induce remission, manage symptoms, and improve survival rates in patients with leukemia. Key medical uses include treating acute and chronic leukemia, lymphoma, and other hematological malignancies.DUKE
cAMP-phosphodiesterase inhibitor23924 An agent that blocks the breakdown of cyclic adenosine monophosphate (cAMP), increasing its levels and enhancing cellular signaling. Therapeutically, it is used to treat respiratory diseases such as asthma and chronic obstructive pulmonary disease (COPD), as well as certain cardiovascular conditions.DUKE
Fungicide24127 An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage.DUKE
Insecticide24852 An agent that kills or repels insects, used to control pests and prevent disease transmission. Therapeutically, insecticides have applications in public health and veterinary medicine, key medical uses include controlling insect-borne diseases such as malaria, typhus, and Lyme disease.DUKE
Anti-angiogenic48422 An agent that inhibits the formation of new blood vessels, playing a crucial role in cancer treatment by starving tumors of oxygen and nutrients. Therapeutically, it is used to manage cancer, age-related macular degeneration, and other diseases characterized by excessive angiogenesis, reducing tumor growth and slowing disease progression.CHEBI
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General Reference
  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. 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.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.