isoxanthohumol

Synonyms: "7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one", "7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methyl-2-butenyl)-2,3-dihydro-4H-chromen-4-one"

Source: isoxanthohumol is the most abundant and an important prenylated flavonoid present in hopped beers.

Identifiers:

IUPAC Name: 7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
CAS Number: 70872-29-6
PubChem ID: 513197
InChiKey: YKGCBLWILMDSAV-UHFFFAOYSA-N
Canonical SMILES: CC(=CCC1=C(C=C(C2=C1OC(CC2=O)C3=CC=C(C=C3)O)OC)O)C

Structural Properties:

Molecular Formula: C₂₁H₂₂O₅
Molecular Weight: 354.396

Pharmacophore Features:

Number of bond donors: 2
Number of bond acceptors: 5
Number of atoms different from hydrogen: 26

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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.