(4R)-3-[(S)-hydroxy-(4-hydroxy-3-methoxyphenyl)methyl]-4-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one
PubChem CID: 101392635
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| Topological Polar Surface Area | 105.0 |
|---|---|
| Hydrogen Bond Donor Count | 3.0 |
| Heavy Atom Count | 27.0 |
| Description | 7-hydroxymatairesinol is a member of the class of compounds known as dibenzylbutyrolactone lignans. Dibenzylbutyrolactone lignans are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety. 7-hydroxymatairesinol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 7-hydroxymatairesinol can be found in sesame, which makes 7-hydroxymatairesinol a potential biomarker for the consumption of this food product. Hydroxymatairesinol (HMR) is a lignan found in Norway spruce (Picea abies). It is an enterolactone precursor with anticancer activities. In rats, HMR decreased the volume of induced tumours and stabilised established tumours, as well as preventing the development of new tumours. It has also shown anti-oxidant properties in vitro . |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 499.0 |
| Database Name | cmaup_ingredients;fooddb_chem_all;hmdb_chem_all;pubchem |
| Defined Atom Stereocenter Count | 2.0 |
| Iupac Name | (4R)-3-[(S)-hydroxy-(4-hydroxy-3-methoxyphenyl)methyl]-4-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one |
| Prediction Hob | 1.0 |
| Class | Furanoid lignans |
| Xlogp | 2.7 |
| Superclass | Lignans, neolignans and related compounds |
| Subclass | Tetrahydrofuran lignans |
| Molecular Formula | C20H22O7 |
| Prediction Swissadme | 1.0 |
| Inchi Key | ZZSOKNNVDKKSDE-LPHKOSDUSA-N |
| Fcsp3 | 0.35 |
| Rotatable Bond Count | 6.0 |
| Synonyms | (-)-7-Hydroxymatairesinol |
| Compound Name | (4R)-3-[(S)-hydroxy-(4-hydroxy-3-methoxyphenyl)methyl]-4-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one |
| Kingdom | Organic compounds |
| Prediction Hob Swissadme | 1.0 |
| Exact Mass | 374.137 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 374.137 |
| Hydrogen Bond Acceptor Count | 7.0 |
| Molecular Weight | 374.4 |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 3.0 |
| Total Bond Stereocenter Count | 0.0 |
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Esol | -3.7951006888888896 |
| Inchi | InChI=1S/C20H22O7/c1-25-16-8-11(3-5-14(16)21)7-13-10-27-20(24)18(13)19(23)12-4-6-15(22)17(9-12)26-2/h3-6,8-9,13,18-19,21-23H,7,10H2,1-2H3/t13-,18?,19+/m0/s1 |
| Smiles | COC1=C(C=CC(=C1)C[C@H]2COC(=O)C2[C@@H](C3=CC(=C(C=C3)O)OC)O)O |
| Defined Bond Stereocenter Count | 0.0 |
| Taxonomy Direct Parent | Dibenzylbutyrolactone lignans |
- 1. Outgoing r'ship
FOUND_INto/from Sesamum Indicum (Plant) Rel Props:Source_db:cmaup_ingredients