Welcome to DrugBank 4.0! If you prefer, you can still go back to version 3.0.
Identification
NameMatairesinol
Accession NumberDB04200  (EXPT02118)
Typesmall molecule
Groupsexperimental
DescriptionNot Available
Structure
Thumb
Synonyms
SynonymLanguageCode
(-)-MatairesinolNot AvailableNot Available
(alphaR,betaR)-alpha,beta-Bis(4-hydroxy-3-methoxybenzyl)butyrolactoneNot AvailableNot Available
3R,4R-Bis((4-hydroxy-3-methoxyphenyl)methyl)dihydro-2(3H)-furanoneNot AvailableNot Available
Artigenin congenerNot AvailableNot Available
Dibenzylbutyrolactone lignanolideNot AvailableNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot 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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassLignans and Norlignans
ClassLignan Lactones
SubclassNot Available
Direct parentLignan Lactones
Alternative parentsFuran Lignans; Methoxyphenols and Derivatives; Anisoles; Alkyl Aryl Ethers; Tetrahydrofurans; Oxolanes; Polyols; Carboxylic Acid Esters; Lactones; Polyamines; Enols
Substituentsmethoxyphenol; phenol ether; anisole; alkyl aryl ether; phenol derivative; gamma butyrolactone; benzene; tetrahydrofuran; oxolane; lactone; polyol; carboxylic acid ester; enol; carboxylic acid derivative; ether; polyamine
Classification descriptionThis compound belongs to the lignan lactones. These are compounds containing a lactone glycosidically linked to a lignan moiety.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
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
Property Value Probability
Human Intestinal Absorption + 0.9103
Blood Brain Barrier + 0.6061
Caco-2 permeable + 0.6774
P-glycoprotein substrate Substrate 0.5261
P-glycoprotein inhibitor I Non-inhibitor 0.7624
P-glycoprotein inhibitor II Inhibitor 0.8132
Renal organic cation transporter Non-inhibitor 0.7484
CYP450 2C9 substrate Non-substrate 0.7603
CYP450 2D6 substrate Non-substrate 0.8589
CYP450 3A4 substrate Non-substrate 0.545
CYP450 1A2 substrate Inhibitor 0.8403
CYP450 2C9 substrate Inhibitor 0.879
CYP450 2D6 substrate Non-inhibitor 0.8387
CYP450 2C19 substrate Inhibitor 0.8861
CYP450 3A4 substrate Inhibitor 0.7138
CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.8727
Ames test Non AMES toxic 0.7809
Carcinogenicity Non-carcinogens 0.9318
Biodegradation Not ready biodegradable 0.7997
Rat acute toxicity 2.4961 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9594
hERG inhibition (predictor II) Non-inhibitor 0.7501
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
water solubility1.21e-02 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 area85.22ChemAxon
rotatable bond count6ChemAxon
refractivity95.63ChemAxon
polarizability36.86ChemAxon
number of rings3ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleYesChemAxon
Spectra
SpectraNot 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 ReferenceNot Available
External Links
ResourceLink
KEGG CompoundC10682
PubChem Compound119205
PubChem Substance46507098
ChemSpider106491
HETMAX
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

1. Dehydrogenase/reductase SDR family member 4-like 2

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Dehydrogenase/reductase SDR family member 4-like 2 Q6PKH6 Details

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

Comments
Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:23