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Identification
NameMatairesinol
Accession NumberDB04200  (EXPT02118)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
Synonyms
(-)-Matairesinol
(alphaR,betaR)-alpha,beta-Bis(4-hydroxy-3-methoxybenzyl)butyrolactone
3R,4R-Bis((4-hydroxy-3-methoxyphenyl)methyl)dihydro-2(3H)-furanone
Artigenin congener
Dibenzylbutyrolactone lignanolide
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
UNIINot Available
CAS number580-72-3
WeightAverage: 358.3851
Monoisotopic: 358.141638436
Chemical FormulaC20H22O6
InChI KeyInChIKey=MATGKVZWFZHCLI-LSDHHAIUSA-N
InChI
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
IUPAC Name
(3R,4R)-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one
SMILES
[H][C@]1(CC2=CC=C(O)C(OC)=C2)COC(=O)[C@]1([H])CC1=CC=C(O)C(OC)=C1
Taxonomy
DescriptionThis compound 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
  • Methoxybenzene
  • Phenol ether
  • Anisole
  • Phenol
  • Alkyl aryl ether
  • Benzenoid
  • Gamma butyrolactone
  • Monocyclic benzene moiety
  • Oxolane
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9103
Blood Brain Barrier+0.6061
Caco-2 permeable+0.6774
P-glycoprotein substrateSubstrate0.5261
P-glycoprotein inhibitor INon-inhibitor0.7624
P-glycoprotein inhibitor IIInhibitor0.8132
Renal organic cation transporterNon-inhibitor0.7484
CYP450 2C9 substrateNon-substrate0.7603
CYP450 2D6 substrateNon-substrate0.8589
CYP450 3A4 substrateNon-substrate0.545
CYP450 1A2 substrateInhibitor0.8403
CYP450 2C9 inhibitorInhibitor0.879
CYP450 2D6 inhibitorNon-inhibitor0.8387
CYP450 2C19 inhibitorInhibitor0.8861
CYP450 3A4 inhibitorInhibitor0.7138
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8727
Ames testNon AMES toxic0.7809
CarcinogenicityNon-carcinogens0.9318
BiodegradationNot ready biodegradable0.7997
Rat acute toxicity2.4961 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9594
hERG inhibition (predictor II)Non-inhibitor0.7501
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0121 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity95.63 m3·mol-1ChemAxon
Polarizability36.86 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
References
Synthesis Reference

Rainer Sjoholm, Patrik Eklund, Jyri Mikkola, Reko Lehtila, Marja Sodervale, Arja Kalapudas, “Method for the preparation of matairesinol.” U.S. Patent US20050080299, issued April 14, 2005.

US20050080299
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Oxidoreductase activity
Specific Function:
Probable oxidoreductase.
Gene Name:
DHRS4L2
Uniprot ID:
Q6PKH6
Molecular Weight:
24585.335 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:23