Matairesinol

Identification

Name
Matairesinol
Accession Number
DB04200  (EXPT02118)
Type
Small Molecule
Groups
Experimental
Description
Not 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
Categories
UNII
Not Available
CAS number
580-72-3
Weight
Average: 358.3851
Monoisotopic: 358.141638436
Chemical Formula
C20H22O6
InChI Key
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][[email protected]]1(CC2=CC=C(O)C(OC)=C2)COC(=O)[[email protected]]1([H])CC1=CC=C(O)C(OC)=C1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UDehydrogenase/reductase SDR family member 4-like 2Not AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not 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 References
Not Available
External Links
Human Metabolome Database
HMDB35698
KEGG Compound
C10682
PubChem Compound
119205
PubChem Substance
46507098
ChemSpider
106491
BindingDB
50240921
ChEBI
6698
ChEMBL
CHEMBL425148
HET
MAX
PDB Entries
2bgm

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not 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 RuleNoChemAxon
MDDR-like RuleYesChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety.
Kingdom
Organic compounds
Super Class
Lignans, neolignans and related compounds
Class
Furanoid lignans
Sub Class
Tetrahydrofuran lignans
Direct Parent
Dibenzylbutyrolactone lignans
Alternative Parents
Lignan lactones / Methoxyphenols / Phenoxy compounds / Methoxybenzenes / Anisoles / Alkyl aryl ethers / 1-hydroxy-2-unsubstituted benzenoids / Gamma butyrolactones / Tetrahydrofurans / Carboxylic acid esters
show 5 more
Substituents
Dibenzylbutyrolactone / Lignan lactone / Methoxyphenol / Phenoxy compound / Anisole / Methoxybenzene / Phenol ether / 1-hydroxy-2-unsubstituted benzenoid / Alkyl aryl ether / Phenol
show 17 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
polyphenol, gamma-lactone, lignan (CHEBI:6698) / Lignans (C10682)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Oxidoreductase activity
Specific Function
Probable oxidoreductase.
Gene Name
DHRS4L2
Uniprot ID
Q6PKH6
Uniprot Name
Dehydrogenase/reductase SDR family member 4-like 2
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]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:38