Bisphenol A

Details

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Internal ID 45e8b8de-891d-4827-8d94-246869c2c7d0
Taxonomy Benzenoids > Benzene and substituted derivatives > Diphenylmethanes > Bisphenols
IUPAC Name 4-[2-(4-hydroxyphenyl)propan-2-yl]phenol
SMILES (Canonical) CC(C)(C1=CC=C(C=C1)O)C2=CC=C(C=C2)O
SMILES (Isomeric) CC(C)(C1=CC=C(C=C1)O)C2=CC=C(C=C2)O
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
InChI Key IISBACLAFKSPIT-UHFFFAOYSA-N
Popularity 20,701 references in papers

Physical and Chemical Properties

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Molecular Formula C15H16O2
Molecular Weight 228.29 g/mol
Exact Mass 228.115029749 g/mol
Topological Polar Surface Area (TPSA) 40.50 Ų
XlogP 3.30
Atomic LogP (AlogP) 3.42
H-Bond Acceptor 2
H-Bond Donor 2
Rotatable Bonds 2

Synonyms

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80-05-7
2,2-Bis(4-hydroxyphenyl)propane
4,4'-Isopropylidenediphenol
Diphenylolpropane
4,4'-Bisphenol A
Bisphenol
Diano
Bisphenol-A
4,4'-(propane-2,2-diyl)diphenol
Biphenol A
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of Bisphenol A

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9959 99.59%
Caco-2 + 0.7639 76.39%
Blood Brain Barrier + 0.5750 57.50%
Human oral bioavailability - 0.6000 60.00%
Subcellular localzation Mitochondria 0.8727 87.27%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8753 87.53%
OATP1B3 inhibitior + 0.9331 93.31%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.8750 87.50%
BSEP inhibitior - 0.5342 53.42%
P-glycoprotein inhibitior - 0.9383 93.83%
P-glycoprotein substrate - 0.9316 93.16%
CYP3A4 substrate - 0.6995 69.95%
CYP2C9 substrate - 0.7461 74.61%
CYP2D6 substrate - 0.6869 68.69%
CYP3A4 inhibition - 0.8309 83.09%
CYP2C9 inhibition + 0.7061 70.61%
CYP2C19 inhibition - 0.5944 59.44%
CYP2D6 inhibition - 0.9305 93.05%
CYP1A2 inhibition + 0.5276 52.76%
CYP2C8 inhibition - 0.8138 81.38%
CYP inhibitory promiscuity - 0.5417 54.17%
UGT catelyzed + 0.9000 90.00%
Carcinogenicity (binary) - 0.6055 60.55%
Carcinogenicity (trinary) Non-required 0.6960 69.60%
Eye corrosion - 0.9197 91.97%
Eye irritation + 1.0000 100.00%
Skin irritation - 0.8721 87.21%
Skin corrosion - 0.9639 96.39%
Ames mutagenesis - 1.0000 100.00%
Human Ether-a-go-go-Related Gene inhibition - 0.7654 76.54%
Micronuclear - 0.7100 71.00%
Hepatotoxicity - 0.5205 52.05%
skin sensitisation + 0.7810 78.10%
Respiratory toxicity - 0.8000 80.00%
Reproductive toxicity + 0.7111 71.11%
Mitochondrial toxicity - 0.8750 87.50%
Nephrotoxicity + 0.6424 64.24%
Acute Oral Toxicity (c) III 0.8640 86.40%
Estrogen receptor binding + 0.9699 96.99%
Androgen receptor binding + 0.8748 87.48%
Thyroid receptor binding + 0.6636 66.36%
Glucocorticoid receptor binding + 0.9047 90.47%
Aromatase binding + 0.8704 87.04%
PPAR gamma + 0.8708 87.08%
Honey bee toxicity - 0.9840 98.40%
Biodegradation - 0.9750 97.50%
Crustacea aquatic toxicity + 0.6900 69.00%
Fish aquatic toxicity + 0.9384 93.84%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
CHEMBL1293255 P15428 15-hydroxyprostaglandin dehydrogenase [NAD+] 11220.2 nM
Potency
via CMAUP
CHEMBL1871 P10275 Androgen Receptor 5900 nM
IC50
PMID: 23768907
CHEMBL340 P08684 Cytochrome P450 3A4 25118.9 nM
6309.6 nM
25118.9 nM
6309.6 nM
Potency
Potency
Potency
Potency
via CMAUP
via CMAUP
via CMAUP
via CMAUP
CHEMBL238 Q01959 Dopamine transporter 19015 nM
IC50
via CMAUP
CHEMBL4159 Q99714 Endoplasmic reticulum-associated amyloid beta-peptide-binding protein 31622.8 nM
Potency
via CMAUP
CHEMBL206 P03372 Estrogen receptor alpha 2271 nM
290 nM
IC50
EC50
via CMAUP
via Super-PRED
CHEMBL242 Q92731 Estrogen receptor beta 1100 nM
757 nM
EC50
EC50
PMID: 23768907
via Super-PRED
CHEMBL222 P23975 Norepinephrine transporter 16620 nM
IC50
via CMAUP
CHEMBL3371 P50406 Serotonin 6 (5-HT6) receptor 5420 nM
IC50
via CMAUP
CHEMBL228 P31645 Serotonin transporter 20325 nM
IC50
via CMAUP
CHEMBL1963 P16473 Thyroid stimulating hormone receptor 39810.7 nM
Potency
via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL2581 P07339 Cathepsin D 87.48% 98.95%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 87.40% 91.11%
CHEMBL5966 P55899 IgG receptor FcRn large subunit p51 86.85% 90.93%
CHEMBL2039 P27338 Monoamine oxidase B 85.11% 92.51%
CHEMBL5409 Q8TDU6 G-protein coupled bile acid receptor 1 83.86% 93.65%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 83.51% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 82.18% 95.56%
CHEMBL1293249 Q13887 Kruppel-like factor 5 81.59% 86.33%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Panax ginseng

Cross-Links

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PubChem 6623
NPASS NPC92730
ChEMBL CHEMBL418971