Bisphenol A

Details

• 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

• 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

• 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
• Parabis A
• 2,2-Bis(p-hydroxyphenyl)propane
• DIAN
• p,p'-Isopropylidenebisphenol
• Rikabanol
• p,p'-Bisphenol A
• Bisferol A
• 2,2-Di(4-phenylol)propane
• Ipognox 88
• Pluracol 245
• p,p'-Dihydroxydiphenylpropane
• Phenol, 4,4'-(1-methylethylidene)bis-
• 4,4'-Dihydroxydiphenylpropane
• Ucar bisphenol A
• 4-[2-(4-hydroxyphenyl)propan-2-yl]phenol
• Dimethylmethylene-p,p'-diphenol
• p,p'-Isopropylidenediphenol
• BPA
• Bis(4-hydroxyphenyl)propane
• Ucar bisphenol HP
• 4,4'-(1-Methylethylidene)bisphenol
• 2,2-Di(4-hydroxyphenyl)propane
• 4,4'-Isopropylidene diphenol
• 2,2-Bis(hydroxyphenyl)propane
• p,p'-Dihydroxydiphenyldimethylmethane
• 4,4'-Isopropylidenebisphenol
• Bis(4-hydroxyphenyl)dimethylmethane
• Isopropylidenebis(4-hydroxybenzene)
• Bis(4-hydroxyphenyl) dimethylmethane
• 4,4'-Dihydroxydiphenyldimethylmethane
• 2,2-Bis-4'-hydroxyfenylpropan
• 4,4'-Dihydroxy-2,2-diphenylpropane
• Phenol, 4,4'-isopropylidenedi-
• 2,2-(4,4'-Dihydroxydiphenyl)propane
• 4,4'-propane-2,2-diyldiphenol
• Phenol, (1-methylethylidene)bis-
• 4,4' Isopropylidinediphenol
• NCI-C50635
• Dimethylbis(p-hydroxyphenyl)methane
• 2,2-Bis(4'-hydroxyphenyl)propane
• beta-di-p-hydroxyphenylpropane
• Dimethyl bis(p-hydroxyphenyl)methane
• Bisphenol A.
• 4,4'-Dihydroxydiphenyl-2,2-propane
• 4-[1-(4-hydroxyphenyl)-1-methylethyl]phenol
• Bis(p-hydroxyphenyl)propane
• CCRIS 95
• Bisferol A [Czech]
• Phenol, 4,4'-dimethylmethylenedi-
• 2,2-Bis (4-hydroxyphenol) propane
• Propane, 2,2-bis(p-hydroxyphenyl)-
• 4,4'-Dimethylmethylenediphenol
• HSDB 513
• beta,beta'-Bis(p-hydroxyphenyl)propane
• DTXSID7020182
• 4,4-ISOPROPYLIDENEDIPHENOL
• NSC 1767
• EINECS 201-245-8
• 4,4[-Isopropylidenediphenol
• 4,4'-Dihydroxdiphenylpropane
• UNII-MLT3645I99
• BRN 1107700
• 4,4'-Isopropylidenebis[phenol]
• Bisphenol A (BPA)
• CHEBI:33216
• 4,4'-(1-Methylethane-1,1-diyl)diphenol
• AI3-04009
• 2,2-bis[4-Hydroxyphenyl]propane
• MLT3645I99
• 2, 2-Bis(4-hydroxyphenyl)propane
• 2,2-bis(4-hydroxyphenyl) propane
• NSC-1767
• MFCD00002366
• 2,2-(4,4-Dihydroxydiphenyl)propane
• beta,beta-di-(p-hydroxyphenyl)propane
• 2,2-Bis-4'-hydroxyfenylpropan [Czech]
• DTXCID30182
• 25766-59-0
• bisphenol A, disodium salt
• BPA 157
• EC 201-245-8
• di-2,2-(4-Hydroxyphenyl)propane
• 2,2'-Bis(4-hydroxyphenyl)propane
• 4,4'-ISOPROPYLIDENEDIPHENOL (BISPHENOL A)
• 4-06-00-06717 (Beilstein Handbook Reference)
• 4,2-propane
• 2,2-di-(4'-Hydroxyphenyl)-propane
• 4,2-diphenylpropane
• 2,2-Bis(4,4'-hydroxyphenyl)propane
• bis(4-hyd roxyphenyl) dimethylmethane
• NCGC00090952-07
• BISPHENOL-A-2,2',6,6'-D4
• .beta.,.beta.'-Bis(p-hydroxyphenyl)propane
• BISPHENOL-A-3,3',5,5'-D4
• Phenol,4'-isopropylidenedi-
• 27100-33-0
• Bisphenol-A-2,2',3,3',5,5',6,6'-D8
• BISPHENOL A (USP-RS)
• BISPHENOL A [USP-RS]
• Phenol,4'-dimethylmethylenedi-
• 2,4'-Dihydroxydiphenyl)propane
• WLN: QR DX1&1&R DQ
• Propane,2-bis(p-hydroxyphenyl)-
• .beta.-Di-(p-hydroxyphenyl)propane
• Phenol,4'-(1-methylethylidene)bis-
• 4,4'-ISOPROPYLIDENEBIS(PHENOL)
• CAS-80-05-7
• 347841-41-2
• 102438-62-0
• bisphenol A, sodium salt
• bis-phenol-a
• bis-phenol A
• Bis Phenol A
• Millad HBPA
• 2OH
• 4,4'-ISOPROPYLIDENE-DIPHENOL
• 4,4'-bisphenol-A
• Bisphenol A, 97%
• 2e2r
• 2p7g
• BPA (CHRIS Code)
• 4, 4'-Bisphenol A
• Bisphenol A (4,4)
• BISPHENOL A [MI]
• Bisphenol A, >=99%
• D02RQP
• 4,4'-isopropylidendiphenol
• BISPHENOL A [HSDB]
• Bisphenol a(ring 13c12)
• HIDORIN F 285
• BIDD:PXR0120
• Oprea1_215541
• p, p'-Isopropylidenediphenol
• SCHEMBL15062
• bis(4-hydroxyphenyl)-propane
• MLS001055461
• BIDD:ER0208
• 4,4'-Isopropylidenedi-Phenol
• p, p'-Dihydroxydiphenylpropane
• (1-methylethylidene)bis-Phenol
• 2, 2-Di(4-phenylol)propane
• 4,4'-Isopropylidenediphenol B
• 4,4'-methylethylidenebisphenol
• 4, 4'- isopropylidenediphenol
• CHEMBL418971
• GTPL7865
• 4, 4'-Dihydroxydiphenylpropane
• 2, 2-Bis(hydroxyphenyl)propane
• .beta.-di-p-hydroxyphenylpropane
• 2,2-bis(4-hydroxyphenyl)propan
• 4,4'-Dimethylmethylenedi-Phenol
• 4,4'-Isopropylidendiphenol dust
• BDBM29608
• beta-Di-(p-hydroxyphenyl)propane
• BP_01 (BPA)
• BPA 154
• NSC1767
• 2,2-bis(p-hydroxyphenyl)-propane
• HMS2866B07
• HMS3749E11
• KUC105370N
• 2,2-di(p-hydroxy-phenyl-)propane
• 4,4'-Isopropylidenediphenol, 8CI
• 2,2-bis-(p-hydroxyphenyl)-propane
• CS-B1737
• NSC17959
• 2,2-bis-(4-hydroxy phenyl)propane
• 2,2-bis-(4-hydroxyphenyl) propane
• 2,2-bis-(4-hydroxyphenyl)-propane
• Tox21_202992
• Tox21_400088
• (C15-H16-O2)x-
• 4,4?-(1-Methylethylidene)bisphenol
• BBL010647
• dimethyl bis(p-hydroxyphenyl)methane
• KSC-7-199
• NSC-17959
• s6007
• STK801675
• 2,2-bis-(4- hydroxyphenyl)-propane
• p, p'-Dihydroxydiphenyldimethylmethane
• 4,4'-(1-methylethylidene)bis-phenol
• 4,4'-dihydroxy diphenyl-2,2-propane
• AKOS000119022
• 4, 4'-Dihydroxydiphenyl-2,2-propane
• 4, 4'-Dihydroxydiphenyldimethylmethane
• CCG-214370
• DB06973
• LS-1788
• beta, beta'-Bis(p-hydroxyphenyl)propane
• Fenol, 4,4'-(1-metiletiliden) bis-
• UPCMLD0ENAT5883875:001
• NCGC00090952-01
• NCGC00090952-02
• NCGC00090952-03
• NCGC00090952-04
• NCGC00090952-05
• NCGC00090952-06
• NCGC00090952-08
• NCGC00090952-09
• NCGC00260537-01
• Phenol, 4,4 -(1-methylethylidene)bis-
• HY-18260
• SMR000315090
• VS-02603
• 4,4'-(1-Methylethylidene)bisphenol, 9CI
• 4,4'-ISOPROPYLIDENEDIPHENOL [INCI]
• Bisphenol A 100 microg/mL in Acetonitrile
• 1,1'-(1-Methylethylidene)bisphenylol, 9CI
• B0494
• FT-0609178
• FT-0663365
• FT-0663366
• FT-0663367
• EN300-19430
• Bisphenol A 2,2-Bis(4-hydroxyphenyl) propane
• D77313
• 4,4'-Isopropylidenediphenol, analytical standard
• 4,4'-ISOPROPYLIDENEDIPHENOL; BISPHENOL A
• Bisphenol A-d14 100 Amicrog/mL in Acetonitrile
• A839823
• AE-848/01247026
• Q271980
• SR-01000596928
• SR-01000596928-1
• BRD-K41494493-001-04-7
• Bisphenol A, certified reference material, TraceCERT(R)
• F1284-0895
• Z104473824
• Bisphenol A, United States Pharmacopeia (USP) Reference Standard
• InChI=1/C15H16O2/c1-15(2,11-3-7-13(16)8-4-11)12-5-9-14(17)10-6-12/h3-10,16-17H,1-2H

2D Structure

ADMET Properties (via admetSAR 2)

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

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

• Panax ginseng

Cross-Links

• PubChem: 6623
• NPASS: NPC92730
• ChEMBL: CHEMBL418971