Bisphenol A
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Identification
- Generic Name
- Bisphenol A
- DrugBank Accession Number
- DB06973
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 228.2863
Monoisotopic: 228.115029756 - Chemical Formula
- C15H16O2
- Synonyms
- 4,4'-Bisphenol A
- 4,4'-Isopropylidenediphenol
- Bisphenol-A
- BPA
- Dianin's compound
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism AAndrogen receptor antagonistHumans AEstrogen receptor beta agonistHumans UEstrogen-related receptor gamma Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as bisphenols. These are methylenediphenols, HOC6H4CH2C6H4OH, commonly p,p-methylenediphenol, and their substitution products (generally derived from condensation of two equivalent amounts of a phenol with an aldehyde or ketone).
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Diphenylmethanes
- Direct Parent
- Bisphenols
- Alternative Parents
- Phenylpropanes / 1-hydroxy-2-unsubstituted benzenoids / Organooxygen compounds / Hydrocarbon derivatives
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / Aromatic homomonocyclic compound / Bisphenol / Hydrocarbon derivative / Organic oxygen compound / Organooxygen compound / Phenol / Phenylpropane
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- bisphenol (CHEBI:33216) / Bisphenols (C13624)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- MLT3645I99
- CAS number
- 80-05-7
- InChI Key
- IISBACLAFKSPIT-UHFFFAOYSA-N
- 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
- IUPAC Name
- 4-[2-(4-hydroxyphenyl)propan-2-yl]phenol
- SMILES
- CC(C)(C1=CC=C(O)C=C1)C1=CC=C(O)C=C1
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0032133
- KEGG Compound
- C13624
- PubChem Compound
- 6623
- PubChem Substance
- 99443444
- ChemSpider
- 6371
- BindingDB
- 29608
- 1433347
- ChEBI
- 33216
- ChEMBL
- CHEMBL418971
- ZINC
- ZINC000000056434
- PDBe Ligand
- 2OH
- Wikipedia
- Bisphenol_A
- PDB Entries
- 2e2r / 2p7g / 3uu7 / 5it1 / 6i63 / 6lit / 9f7w
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0865 mg/mL ALOGPS logP 3.81 ALOGPS logP 4.04 Chemaxon logS -3.4 ALOGPS pKa (Strongest Acidic) 9.78 Chemaxon pKa (Strongest Basic) -5.5 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 40.46 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 79.28 m3·mol-1 Chemaxon Polarizability 25.41 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9957 Blood Brain Barrier + 0.6925 Caco-2 permeable + 0.8784 P-glycoprotein substrate Non-substrate 0.5494 P-glycoprotein inhibitor I Non-inhibitor 0.9048 P-glycoprotein inhibitor II Non-inhibitor 0.949 Renal organic cation transporter Non-inhibitor 0.8643 CYP450 2C9 substrate Non-substrate 0.7553 CYP450 2D6 substrate Non-substrate 0.8379 CYP450 3A4 substrate Substrate 0.5162 CYP450 1A2 substrate Inhibitor 0.5276 CYP450 2C9 inhibitor Inhibitor 0.7061 CYP450 2D6 inhibitor Non-inhibitor 0.9305 CYP450 2C19 inhibitor Non-inhibitor 0.5944 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5417 Ames test Non AMES toxic 0.9729 Carcinogenicity Non-carcinogens 0.6607 Biodegradation Not ready biodegradable 0.9717 Rat acute toxicity 1.8158 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9619 hERG inhibition (predictor II) Non-inhibitor 0.8543
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 163.3028864 predictedDarkChem Lite v0.1.0 [M-H]- 163.5584864 predictedDarkChem Lite v0.1.0 [M-H]- 163.9315864 predictedDarkChem Lite v0.1.0 [M-H]- 158.35127 predictedDeepCCS 1.0 (2019) [M+H]+ 163.5219864 predictedDarkChem Lite v0.1.0 [M+H]+ 164.9955864 predictedDarkChem Lite v0.1.0 [M+H]+ 164.7655864 predictedDarkChem Lite v0.1.0 [M+H]+ 160.70927 predictedDeepCCS 1.0 (2019) [M+Na]+ 163.1637864 predictedDarkChem Lite v0.1.0 [M+Na]+ 163.9606864 predictedDarkChem Lite v0.1.0 [M+Na]+ 164.8345864 predictedDarkChem Lite v0.1.0 [M+Na]+ 166.80243 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsAndrogen receptor
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues (PubMed:19022849). Transcription factor activity is modulated by bound coactivator and corepressor proteins like ZBTB7A that recruits NCOR1 and NCOR2 to the androgen response elements/ARE on target genes, negatively regulating androgen receptor signaling and androgen-induced cell proliferation (PubMed:20812024). Transcription activation is also down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3
- Specific Function
- androgen binding
- Gene Name
- AR
- Uniprot ID
- P10275
- Uniprot Name
- Androgen receptor
- Molecular Weight
- 99187.115 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
2. DetailsEstrogen receptor beta
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1/ER-alpha, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner (PubMed:20074560)
- Specific Function
- DNA binding
- Gene Name
- ESR2
- Uniprot ID
- Q92731
- Uniprot Name
- Estrogen receptor beta
- Molecular Weight
- 59215.765 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
3. DetailsEstrogen-related receptor gamma
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Orphan receptor that acts as a transcription activator in the absence of bound ligand. Binds specifically to an estrogen response element and activates reporter genes controlled by estrogen response elements (By similarity). Induces the expression of PERM1 in the skeletal muscle
- Specific Function
- AF-2 domain binding
- Gene Name
- ESRRG
- Uniprot ID
- P62508
- Uniprot Name
- Estrogen-related receptor gamma
- Molecular Weight
- 51305.485 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Drug created at September 15, 2010 21:18 / Updated at August 26, 2024 19:21