Bisphenol A

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
TargetActionsOrganism
UEstrogen-related receptor gammaNot AvailableHumans
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
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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
Human Metabolome Database
HMDB0032133
KEGG Compound
C13624
PubChem Compound
6623
PubChem Substance
99443444
ChemSpider
6371
BindingDB
29608
RxNav
1433347
ChEBI
33216
ChEMBL
CHEMBL418971
ZINC
ZINC000000056434
PDBe Ligand
2OH
Wikipedia
Bisphenol_A
PDB Entries
2e2r / 2p7g / 3uu7 / 5it1 / 6i63 / 6lit

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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
PropertyValueSource
Water Solubility0.0865 mg/mLALOGPS
logP3.81ALOGPS
logP4.04Chemaxon
logS-3.4ALOGPS
pKa (Strongest Acidic)9.78Chemaxon
pKa (Strongest Basic)-5.5Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area40.46 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity79.28 m3·mol-1Chemaxon
Polarizability25.41 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9957
Blood Brain Barrier+0.6925
Caco-2 permeable+0.8784
P-glycoprotein substrateNon-substrate0.5494
P-glycoprotein inhibitor INon-inhibitor0.9048
P-glycoprotein inhibitor IINon-inhibitor0.949
Renal organic cation transporterNon-inhibitor0.8643
CYP450 2C9 substrateNon-substrate0.7553
CYP450 2D6 substrateNon-substrate0.8379
CYP450 3A4 substrateSubstrate0.5162
CYP450 1A2 substrateInhibitor0.5276
CYP450 2C9 inhibitorInhibitor0.7061
CYP450 2D6 inhibitorNon-inhibitor0.9305
CYP450 2C19 inhibitorNon-inhibitor0.5944
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5417
Ames testNon AMES toxic0.9729
CarcinogenicityNon-carcinogens0.6607
BiodegradationNot ready biodegradable0.9717
Rat acute toxicity1.8158 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9619
hERG inhibition (predictor II)Non-inhibitor0.8543
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-03g0-1790000000-7521406d051aed77fe2f
GC-MS Spectrum - EI-BGC-MSsplash10-03di-2290000000-5a53b16778a578ff5d0d
Mass Spectrum (Electron Ionization)MSsplash10-03di-3590000000-0cd99fd08fc2fad698f3
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0zfs-4960000000-b4ebb7f1ff08fbb41adb
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-1090000000-80a2709d727e93053cd1
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0090000000-c33246c7d9d8b300c90c
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0090000000-e5f7d4cb43ef56a85056
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0532-9340000000-c3298310f84ad87b1310
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000t-9000000000-75784b9156574d6f1762
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4j-1900000000-1316f0a328865698ba14
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-2910000000-695a79d28710d1361ba0
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-3090000000-ba3d286d5aa01e4d482e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-067s-4900000000-e6fb9cb17f334ba86fda
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0032-0930000000-2e20ef93b6cfcdd2e10a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00uj-2900000000-a469c96fe9db691a5f83
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00lu-2900000000-7d414e07c65b31566175
1H NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-163.3028864
predicted
DarkChem Lite v0.1.0
[M-H]-163.5584864
predicted
DarkChem Lite v0.1.0
[M-H]-163.9315864
predicted
DarkChem Lite v0.1.0
[M-H]-158.35127
predicted
DeepCCS 1.0 (2019)
[M+H]+163.5219864
predicted
DarkChem Lite v0.1.0
[M+H]+164.9955864
predicted
DarkChem Lite v0.1.0
[M+H]+164.7655864
predicted
DarkChem Lite v0.1.0
[M+H]+160.70927
predicted
DeepCCS 1.0 (2019)
[M+Na]+163.1637864
predicted
DarkChem Lite v0.1.0
[M+Na]+163.9606864
predicted
DarkChem Lite v0.1.0
[M+Na]+164.8345864
predicted
DarkChem Lite v0.1.0
[M+Na]+166.80243
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Orphan receptor that acts as transcription activator in the absence of bound ligand. Binds specifically to an estrogen response element and activates reporter genes controlled by estrogen response ...
Gene Name
ESRRG
Uniprot ID
P62508
Uniprot Name
Estrogen-related receptor gamma
Molecular Weight
51305.485 Da
References
  1. 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 June 12, 2020 16:52