sophoraflavanone B

Also known as (S)-8-dimethylallylnaringenin, (-)-(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)chroman-4-one, (-)-(2S)-8-dimethylallylnaringenin, 8-prenylnaringenin, Flavaprenin, 8-PN, 8-Prenylnaringenin

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.

Chemical data

Formula: C20H20O5
Molecular weight: 340.4 g/mol
IUPAC name: (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
SMILES: CC(=CCC1=C2C(=C(C=C1O)O)C(=O)C[C@H](O2)C3=CC=C(C=C3)O)C
InChIKey: LPEPZZAVFJPLNZ-SFHVURJKSA-N
XLogP: 4.3
Polar surface area: 87 Å²
H-bond donors: 3
H-bond acceptors: 5
Formal charge: 0

via PubChem

Drug data · ChEMBL

Molecule type: Small molecule

via ChEMBL · EBI

Wikidata facts

Mass: 340.131074

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found in taxon: Wyethia mollis
canonical SMILES: CC(=CCC1=C(C=C(C2=C1OC(CC2=O)C3=CC=C(C=C3)O)O)O)C
chemical formula: C₂₀H₂₀O₅
isomeric SMILES: CC(=CCC1=C(C=C(C2=C1O[C@@H](CC2=O)C3=CC=C(C=C3)O)O)O)C

Sources (2)

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Encyclopedic overview

7 sections

Contents

Properties
Estrogenic
Other
Chemistry
Etymology
See also
References

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.

Excerpted from Wikipedia’s “sophoraflavanone B” article, available under the CC BY-SA 4.0 licence.

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