Compound: Sophoraflavanone B
SMILES: O=C1c2c(O[C@@H](C1)c3ccc(O)cc3)c(c(O)cc2O)CC=C(C)C
InChIKey: LPEPZZAVFJPLNZ-SFHVURJKSA-N
Synonyms: Sophoraflavanone B, (-)-(2S)-8-dimethylallylnaringenin, CHEBI:50207, (-)-(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)chroman-4-one, (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-2,3-dihydro-4H-chromen-4-one, RefChem:1098889, 5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one, 8-Prenylnaringenin, 53846-50-7, Flavaprenin, (-)-8-Prenylnaringenin, (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one, (S)-8-dimethylallylnaringenin, 8-?Prenylnaringenin, 8-prenyl-naringenin, (S)-5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)-8-(3-METHYLBUT-2-EN-1-YL)CHROMAN-4-ONE, 5L872SZR8X, CHEMBL376915, YS04, (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-4-one, 8-renylnaringenin, (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)chroman-4-one, (s)-8-prenylnaringenin, sorphoraflavanone B, (-)-8-Prenylnaringenin; 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methyl-2-buten-1-yl)-, (2S)-; 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methyl-2-butenyl)-, (2S)- (9CI); 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihyd, HOPEIN, 8-dimethylallylnaringenin, Phloroglucinol Impurity Y, UNII-5L872SZR8X, 8-prenylnaringenin (8-PN), BIDD:ER0149, cid_509245, orb1297527, orb3139281, SCHEMBL1171435, SCHEMBL29396586, BDBM19460, DTXSID60333083, LPEPZZAVFJPLNZ-SFHVURJKSA-N, AIDS095901, GLXC-09019, HY-N2787, EBC-13162, AKOS032948436, 8-Prenylnaringenin, analytical standard, AT10700, FP64928, 8-Prenylnaringenin (Sophoraflavanone B), AC-35053, AS-82967, PD017477, DB-253663, CS-0023305, NS00067003, C18023, EN300-19006927, Q4644281, 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-8-(3-methyl-but-2-enyl)-1-benzopyran-4-one, (2S)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-2,3-dihydro-4H-1-benzopyran-4-one, 4H-1-BENZOPYRAN-4-ONE, 2,3-DIHYDRO-5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)-8-(3-METHYL-2-BUTEN-1-YL)-, (2S)-
Theoretical properties:
molecular_formula: C20H20O5
molecular_weight: 340.4 g/mol
exact_mass: 340.13107373 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 3
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 3
heavy_atom_count: 25
topological_polar_surface_area: 87 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Sophoraflavanone B is a trihydroxyflavanone that is (S)-naringenin having a prenyl group at position 8. It has a role as a platelet aggregation inhibitor and a plant metabolite. It is a member of 4'-hydroxyflavanones, a (2S)-flavan-4-one and a trihydroxyflavanone. It is functionally related to a (S)-naringenin. It is a conjugate acid of a sophoraflavanone B(1-).
chebi: A trihydroxyflavanone that is (<i>S</i>)-naringenin having a prenyl group at position 8.
chembl: Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: 8-Prenylnaringenin (8-PN; also known as flavaprenin, (S)-8-dimethylallylnaringenin, hopein, or sophoraflavanone B) is a prenylflavonoid phytoestrogen. It is reported to be the most estrogenic phytoestrogen known. The compound is equipotent at the two forms of estrogen receptors, ERα and ERβ, and it acts as a full agonist of ERα. Its effects are similar to those of estradiol, but it is considerably less potent in comparison.
8-PN is found in hops (Humulus lupulus) and in beer, and is responsible for the estrogenic effects of the former. It can be produced from isoxanthohumol in fungal cells cultures, and by flora in the human intestine.