bisphenol A   Click here for help

GtoPdb Ligand ID: 7865

Synonyms: BPA
PDB Ligand
Compound class: Synthetic organic
Comment: Bisphenol A acts as an estrogen mimic [3-4] and may also have anti-androgenic activity [1].
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 0
Hydrogen bond donors 2
Rotatable bonds 2
Topological polar surface area 40.46
Molecular weight 228.12
XLogP 4.52
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES CC(c1ccc(cc1)O)(c1ccc(cc1)O)C
Isomeric SMILES CC(c1ccc(cc1)O)(c1ccc(cc1)O)C
InChI InChI=1S/C15H16O2/c1-15(2,11-3-7-13(16)8-4-11)12-5-9-14(17)10-6-12/h3-10,16-17H,1-2H3
1. Lee HJ, Chattopadhyay S, Gong EY, Ahn RS, Lee K. (2003)
Antiandrogenic effects of bisphenol A and nonylphenol on the function of androgen receptor.
Toxicol Sci, 75 (1): 40-6. [PMID:12805653]
2. Maruyama K, Nakamura M, Tomoshige S, Sugita K, Makishima M, Hashimoto Y, Ishikawa M. (2013)
Structure-activity relationships of bisphenol A analogs at estrogen receptors (ERs): discovery of an ERα-selective antagonist.
Bioorg Med Chem Lett, 23 (14): 4031-6. [PMID:23768907]
3. Yiu KW, Lee CK, Kwok KC, Cheung NH. (2014)
Measuring the kinetics of the binding of xenoestrogens and estrogen receptor alpha by fluorescence polarization.
Environ Sci Technol, 48 (19): 11591-9. [PMID:25180905]
4. Zhuang S, Zhang C, Liu W. (2014)
Atomic Insights into Distinct Hormonal Activities of Bisphenol A Analogues toward PPARγ and ERα Receptors.
Chem Res Toxicol, 27 (10): 1769-79. [PMID:25233466]