(3R,4R)-3,4-bis[(3-hydroxyphenyl)methyl]oxolan-2-one
PubChem CID: 10685477
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| Compound Synonyms | Enterolactone, 78473-71-9, Enterolakton, (3R,4R)-3,4-bis[(3-hydroxyphenyl)methyl]oxolan-2-one, (+/-)-enterolactone, DTXSID0048183, (-)-Enterolactone, (3R,4R)-3,4-bis(3-hydroxybenzyl)dihydrofuran-2(3H)-one, 2(3H)-Furanone, dihydro-3,4-bis((3-hydroxyphenyl)methyl)-, trans-, HPMF, 77756-20-8, (+/-)- Enterolactone, SCHEMBL121287, (3R,4R)-3,4-bis[(3-hydroxyphenyl)methyl]tetrahydrofuran-2-one, CHEMBL471475, DTXCID6028157, Tox21_303555, EX-A10195, AKOS040758557, FR27510, FS-6841, NCGC00257338-01, DA-73128, CAS-78473-71-9, HY-108692, CS-0029984, NS00076969, Q3055376, trans-3,4-Bis(3-hydroxybenzyl)dihydrofuran-2(3H)-one, 2(3H)-Furanone, dihydro-3,4-bis[(3-hydroxyphenyl)methyl]-,(3R,4R)-rel-, (3R,4R)-rel-dihydro-3,4-bis[(3-hydroxyphenyl)methyl]-2(3H)-furanone, trans-Dihydro-3,4-bis[(3-hydroxyphenyl)methyl]-2(3H)-furanon |
|---|---|
| Topological Polar Surface Area | 66.8 |
| Hydrogen Bond Donor Count | 2.0 |
| Heavy Atom Count | 22.0 |
| Description | Production of intestinal flora acting on lignans present in cereal Enterolactone is a mammalian lignan that have a similar biphenolic structure to lignans from plants. Lignans are compounds with estrogenic properties and are probably the most important source of phytoestrogens in western diets. Mammalian lignans are formed from precursors that are contained mainly in vegetables, whole grain products and berries, via action of intestinal microflora. Enterolactone is produced in the colon by the action of bacteria on secoisolariciresinol, matairesinol and its glycosides. Secoisolariciresinol is converted to enterodiol which is subsequently converted to enterolactone as it passes through the colon. Matairesinol is converted directly to enterolactone. Enterolactone have been shown to possess weakly estrogenic and antiestrogenic activities, and it has been suggested that the high production of this antiestrogenic mammalian lignans in the gut may serve to protect against breast cancer in women and prostate cancer in men, however epidemiological evidence to date is conflicting. (PMID: 16168401, 12270221, 11216511, 12107024). Enterolactone is a biomarker for the consumption of soy beans and other soy products. Enterolactone is found in cereals and cereal products. |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 383.0 |
| Database Name | cmaup_ingredients;fooddb_chem_all;npass_chem_all;pubchem |
| Defined Atom Stereocenter Count | 2.0 |
| Uniprot Id | P02766, P10275 |
| Iupac Name | (3R,4R)-3,4-bis[(3-hydroxyphenyl)methyl]oxolan-2-one |
| Prediction Hob | 1.0 |
| Class | Furanoid lignans |
| Xlogp | 3.3 |
| Superclass | Lignans, neolignans and related compounds |
| Subclass | Tetrahydrofuran lignans |
| Molecular Formula | C18H18O4 |
| Prediction Swissadme | 1.0 |
| Inchi Key | HVDGDHBAMCBBLR-WMLDXEAASA-N |
| Fcsp3 | 0.2777777777777778 |
| Logs | -3.075 |
| Rotatable Bond Count | 4.0 |
| State | Solid |
| Logd | 2.972 |
| Synonyms | 2,3-Bhbb, 2,3-Bis(3-hydroxybenzyl)butyrolactone, 2,3-bis(3'-hydroxybenzyl)butyrolactone, 2(3H)-Furanone, dihydro-3,4-bis((3-hydroxyphenyl)methyl)-, 3,4-Bis((3-hydroxyphenyl)methyl)dihydro-2-(3H)-furanone, BHMDF, dihydro-3,4-Bis((3-hydroxyphenyl)methyl)-2(3H)-furanone, Dihydro-3,4-bis(3-hydroxyphenyl)methyl-2(3H)-furanone, 9CI, HPMF, trans-2,3-Bis(3-hydroxybenzyl)-gamma-butyrolactone |
| Substituent Name | Dibenzylbutyrolactone, Lignan lactone, Phenol, Benzenoid, Gamma butyrolactone, Monocyclic benzene moiety, Oxolane, Lactone, Carboxylic acid ester, Oxacycle, Organoheterocyclic compound, Monocarboxylic acid or derivatives, Ether, Carboxylic acid derivative, Hydrocarbon derivative, Organooxygen compound, Carbonyl group, Aromatic heteromonocyclic compound |
| Compound Name | (3R,4R)-3,4-bis[(3-hydroxyphenyl)methyl]oxolan-2-one |
| Kingdom | Organic compounds |
| Prediction Hob Swissadme | 1.0 |
| Exact Mass | 298.121 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 298.121 |
| Hydrogen Bond Acceptor Count | 4.0 |
| Molecular Weight | 298.3 |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 2.0 |
| Total Bond Stereocenter Count | 0.0 |
| Esol | -3.9209319636363635 |
| Inchi | InChI=1S/C18H18O4/c19-15-5-1-3-12(8-15)7-14-11-22-18(21)17(14)10-13-4-2-6-16(20)9-13/h1-6,8-9,14,17,19-20H,7,10-11H2/t14-,17+/m0/s1 |
| Smiles | C1[C@@H]([C@H](C(=O)O1)CC2=CC(=CC=C2)O)CC3=CC(=CC=C3)O |
| Nring | 3.0 |
| Defined Bond Stereocenter Count | 0.0 |
- 1. Outgoing r'ship
FOUND_INto/from Linum Usitatissimum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all