8-prenylnaringenin

Synonyms: "sophoraflavanone B", "(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-2,3-dihydro-4H-chromen-4-one", "flavaprenin"

Source: 8-prenylnaringenin is a prenylflavonoid and a potent plant-derived phytoestrogen.

Identifiers:

IUPAC Name: (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
CAS Number: 53846-50-7
PubChem ID: 480764
InChiKey: LPEPZZAVFJPLNZ-SFHVURJKSA-N
Canonical SMILES: CC(=CCC1=C(C=C(C2=C1OC(CC2=O)C3=CC=C(C=C3)O)O)O)C

Structural Properties:

Molecular Formula: C₂₀H₂₀O₅
Molecular Weight: 340.370

Pharmacophore Features:

Number of bond donors: 3
Number of bond acceptors: 5
Number of atoms different from hydrogen: 25

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2D structure (.sdf)
3D structure (.sdf)
3D structure (.mol2)
3D structure (.pdb)
3D structure (.pdbqt)

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Evidence Supporting This Chemical as an Endocrine Disruptor
TEDX List of Potential Endocrine Disruptors

Coldham NG, Sauer MJ. 2001. Identification, quantitation and biological activity of phytoestrogens in a dietary supplement for breast enhancement. Food & Chemical Toxicology 39(12):1211-1224.

Izzo G, Soder O, Svechnikov K. 2011. The prenylflavonoid phytoestrogens 8-prenylnaringenin and isoxanthohumol diferentially suppress steroidogenesis in rat Leydig cells in ontogenesis. J Appl Toxicol 31(6):589-594.

Milligan S, Kalita J, Pocock V, Heyerick A, De Cooman L, Rong H, De Keukeleire D. 2002. Oestrogenic activity of the hop phyto-oestrogen, 8-prenylnaringenin. Reproduction 123(2):235-242.