(-)-MATAIRESINOL
General Information
| Synonyms: | (8R,8'R)-(-)-Matairesinol, 2(3H)-Furanone, dihydro-3,4-divanillyl-, 2(3H)-Furanone, dihydro-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-,(3R-trans)-, Matairesinol |
| Chemical Names: | (3R,4R)-3,4-bis(4-hydroxy-3-methoxybenzyl)dihydrofuran-2(3H)-one |
| CAS number: | 580-72-3 |
| JECFA number: | 2210 |
| FEMA number: | 4762 |
| INS: | 164 |
| Functional Class: |
Flavouring Agent FLAVOURING_AGENT |
From apps.who.int
Evaluations
| Evaluation year: | 2014 |
| ADI: | No safety concern at current levels of intake when used as a flavouring agent |
| Meeting: | 79 |
| Specs Code: | N |
| Report: | TRS 990-JECFA 79/80 |
| Specification: | FAO JECFA Monographs 16/73 |
From apps.who.int
Computed Descriptors
Download SDF| 2D Structure | |
| CID | 119205 |
| IUPAC Name | (3R,4R)-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one |
| 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 |
| InChI Key | MATGKVZWFZHCLI-LSDHHAIUSA-N |
| Canonical SMILES | COC1=C(C=CC(=C1)CC2COC(=O)C2CC3=CC(=C(C=C3)O)OC)O |
| Molecular Formula | C20H22O6 |
| Wikipedia | Matairesinol |
From Pubchem
Computed Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 358.39 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 6 |
| Complexity | 469.0 |
| CACTVS Substructure Key Fingerprint | A A A D c e B 4 O A A A A A A A A A A A A A A A A A A A A S A A A A A w Y A A A A A A A A A A B Q A A A G g A A C A A A D Q S g m A I y D o A A B g C I A i D S C A A C C A A g I A A I i A E G i I g N J j K G M R q C c C M k w B E L u A e K y P C O o A A B A A A A Q A B A A A I A A A C A A A A A A A A A A A = = |
| Topological Polar Surface Area | 85.2 |
| Monoisotopic Mass | 358.142 |
| Exact Mass | 358.142 |
| XLogP3 | None |
| XLogP3-AA | 3.3 |
| Compound Is Canonicalized | True |
| Formal Charge | 0 |
| Heavy Atom Count | 26 |
| Defined Atom Stereocenter Count | 2 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
From Pubchem
Food Additives Biosynthesis/Degradation
ADMET Predicted Profile --- Classification
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.6061 |
| Human Intestinal Absorption | HIA+ | 0.9103 |
| Caco-2 Permeability | Caco2+ | 0.6774 |
| P-glycoprotein Substrate | Substrate | 0.5261 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.7624 |
| Inhibitor | 0.8132 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.7484 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.9227 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7603 |
| CYP450 2D6 Substrate | Non-substrate | 0.8589 |
| CYP450 3A4 Substrate | Non-substrate | 0.5450 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.8403 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.8790 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8387 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.8861 |
| CYP450 3A4 Inhibitor | Inhibitor | 0.7138 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.8727 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9594 |
| Non-inhibitor | 0.7501 | |
| AMES Toxicity | Non AMES toxic | 0.7809 |
| Carcinogens | Non-carcinogens | 0.9318 |
| Fish Toxicity | High FHMT | 0.9851 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9828 |
| Honey Bee Toxicity | High HBT | 0.6797 |
| Biodegradation | Not ready biodegradable | 0.7997 |
| Acute Oral Toxicity | III | 0.6811 |
| Carcinogenicity (Three-class) | Non-required | 0.6420 |
From admetSAR
ADMET Predicted Profile --- Regression
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.8932 | LogS |
| Caco-2 Permeability | 0.7164 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.4961 | LD50, mol/kg |
| Fish Toxicity | 0.5517 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.6214 | pIGC50, ug/L |
From admetSAR
Taxonomic Classification
| Kingdom | Organic compounds |
|---|---|
| Superclass | Lignans, neolignans and related compounds |
| Class | Furanoid lignans |
| Subclass | Tetrahydrofuran lignans |
| Intermediate Tree Nodes | 9,9'-epoxylignans |
| Direct Parent | Dibenzylbutyrolactone lignans |
| Alternative Parents |
|
| Molecular Framework | Aromatic heteromonocyclic compounds |
| 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 |
| 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. |
From ClassyFire
Targets
- General Function:
- Oxidoreductase activity
- Specific Function:
- Probable oxidoreductase.
- Gene Name:
- DHRS4L2
- Uniprot ID:
- Q6PKH6
- Molecular Weight:
- 24585.335 Da
From T3DB