apigenin

Synonyms: "chamomile", "spigenin", "versulin", "apigenol", "4',5,7-trihydroxyflavone", "apigenine", "5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one"

Source: apigenin is a flavonoid that is found in several fruits and vegetables.

Identifiers:

IUPAC Name: 5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
CAS Number: 520-36-5
PubChem ID: 5280443
InChiKey: KZNIFHPLKGYRTM-UHFFFAOYSA-N
Canonical SMILES: C1=CC(=CC=C1C2=CC(=O)C3=C(C=C(C=C3O2)O)O)O

Structural Properties:

Molecular Formula: C₁₅H₁₀O₅
Molecular Weight: 270.237

Pharmacophore Features:

Number of bond donors: 3
Number of bond acceptors: 5
Number of atoms different from hydrogen: 20

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

Nishihara T, Nishikawa J, Kanayama T, Dakeyama F, Saito K, Imagawa M, Takatori S, Kitagawa Y, Hori S, Utsumi H. 2000. Estrogenic activities of 517 chemicals by yeast two-hybrid assay. Journal of Health Science 46(4):282-298.

Oberdorster E, Clay MA, Cottam DM, Wilmot FA, McLachlan JA, Milner MJ. 2001. Common phytochemicals are ecdysteroid agonists and antagonists: a possible evolutionary link between vertebrate and invertebrate steroid hormones. J Steroid Biochem Mol Biol 77(4-5):229-238, DOI: 10.1016/S0960-0760(01)00067-X.

Rosenberg RS, Grass L, Jenkins DJ, Kendall CWC, Diamandis EP. 1998. Modulation of androgen and progesterone receptors by phytochemicals in breast cancer cell lines. Biochemical & Biophysical Research Communications 248(3):935-939.

Scippo ML, Argiris C, Van De Weerdt C, Muller M, Willemsen P, Martial J, Maghuin-Rogister G. 2004. Recombinant human estrogen, androgen and progesterone receptors for detection of potential endocrine disruptors. Analytical & Bioanalytical Chemistry 378(3)