4,4'-Methylenediphenol

Details

• Internal ID: 00a54c7b-986f-429b-8e37-b5d764710396
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Diphenylmethanes
• IUPAC Name: 4-[(4-hydroxyphenyl)methyl]phenol
• SMILES (Canonical): C1=CC(=CC=C1CC2=CC=C(C=C2)O)O
• SMILES (Isomeric): C1=CC(=CC=C1CC2=CC=C(C=C2)O)O
• InChI: InChI=1S/C13H12O2/c14-12-5-1-10(2-6-12)9-11-3-7-13(15)8-4-11/h1-8,14-15H,9H2
• InChI Key: PXKLMJQFEQBVLD-UHFFFAOYSA-N
• Popularity: 794 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₂O₂
• Molecular Weight: 200.23 g/mol
• Exact Mass: 200.083729621 g/mol
• Topological Polar Surface Area (TPSA): 40.50 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 2.69
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• 620-92-8
• 4,4'-Dihydroxydiphenylmethane
• Bisphenol F
• Bis(4-hydroxyphenyl)methane
• Phenol, 4,4'-methylenebis-
• p-(p-Hydroxybenzyl)phenol
• 4-[(4-hydroxyphenyl)methyl]phenol
• Phenol, 4,4'-methylenedi-
• 4,4'-Methylenebisphenol
• BIS(P-HYDROXYPHENYL)METHANE
• p,p'-Bis(hydroxyphenyl)methane
• 4,4'-Methylene diphenol
• 4,4'-bisphenol F
• Bis-(4-hydroxyphenyl)methane
• 4-(4-hydroxybenzyl)phenol
• 4,4'-Methylenebis(phenol)
• 4,4-Dihydroxydiphenylmethane
• NSC 401136
• p,p'-BPF
• PP-BIP-F
• EINECS 210-658-2
• 4,4'-methylenebis-phenol
• HDM
• BRN 2049425
• 4,4'-Methylenebis[Phenol]
• UNII-QD2C19044Z
• CCRIS 9461
• DTXSID9022445
• CHEBI:34575
• HSDB 8091
• KUC106448N
• QD2C19044Z
• MFCD00002385
• KSC-19-052
• NSC-401136
• BPF
• 4-06-00-06664 (Beilstein Handbook Reference)
• 4,4-bisphenol F
• 4,4-Methylenediphenol
• p,p'-Methylenediphenol
• methyl2-methoxypropionate
• Phenol,4'-methylenebis-
• WLN: QR D1R DQ
• phenol, 4,4'-methylenebis
• bis-(p-hydroxyphenyl)methane
• 4,4'-methanediyl-di-phenol
• SCHEMBL36454
• bis(para-hydroxyphenyl)methane
• cid_12111
• BIDD:ER0181
• bis-(p-hydroxyphenyl)-methane
• CHEMBL138061
• DTXCID202445
• para-(para-hydroxybenzyl)phenol
• 4,4''-Dihydroxydiphenylmethane
• C(c1ccc(O)cc1)c2ccc(O)cc2
• 4,4'-Bis(hydroxyphenyl)methane
• BDBM76093
• BP_04 (BPF)
• Bisphenol??F, analytical standard
• Bis(4-hydroxyphenyl)methane, 98%
• PHENOL, P,P'-METHYLENEDI-
• Tox21_201163
• NSC401136
• AKOS015909171
• CS-W015617
• HY-W014901
• Bisphenol F 100 microg/mL in Methanol
• 4,4'-BIS-(HYDROXYPHENYL)METHANE
• NCGC00248941-01
• NCGC00258715-01
• AS-17296
• CAS-620-92-8
• PD196956
• SY048317
• Bisphenol F 100 microg/mL in Acetonitrile
• LS-104842
• B0819
• FT-0617058
• F16585
• 4,4 inverted exclamation mark -Methylenediphenol
• A833580
• AE-562/40896944
• Q9658061
• W-109582
• InChI=1/C13H12O2/c14-12-5-1-10(2-6-12)9-11-3-7-13(15)8-4-11/h1-8,14-15H,9H
• T0U

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9946	99.46%
Caco-2	+	0.7215	72.15%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.8489	84.89%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8366	83.66%
OATP1B3 inhibitior	-	0.2704	27.04%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.6207	62.07%
P-glycoprotein inhibitior	-	0.9571	95.71%
P-glycoprotein substrate	-	0.9713	97.13%
CYP3A4 substrate	-	0.7830	78.30%
CYP2C9 substrate	-	0.8036	80.36%
CYP2D6 substrate	+	0.4561	45.61%
CYP3A4 inhibition	-	0.7841	78.41%
CYP2C9 inhibition	+	0.5834	58.34%
CYP2C19 inhibition	+	0.8773	87.73%
CYP2D6 inhibition	-	0.9310	93.10%
CYP1A2 inhibition	+	0.7667	76.67%
CYP2C8 inhibition	-	0.7147	71.47%
CYP inhibitory promiscuity	+	0.7343	73.43%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.5184	51.84%
Carcinogenicity (trinary)	Non-required	0.5536	55.36%
Eye corrosion	-	0.9084	90.84%
Eye irritation	+	0.9970	99.70%
Skin irritation	+	0.5426	54.26%
Skin corrosion	-	0.9509	95.09%
Ames mutagenesis	-	0.9700	97.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8155	81.55%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	+	0.9455	94.55%
Respiratory toxicity	-	0.7889	78.89%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	-	0.8500	85.00%
Nephrotoxicity	-	0.5997	59.97%
Acute Oral Toxicity (c)	III	0.8125	81.25%
Estrogen receptor binding	+	0.9036	90.36%
Androgen receptor binding	+	0.6778	67.78%
Thyroid receptor binding	+	0.5649	56.49%
Glucocorticoid receptor binding	+	0.8143	81.43%
Aromatase binding	+	0.8686	86.86%
PPAR gamma	+	0.8268	82.68%
Honey bee toxicity	-	0.9051	90.51%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.8927	89.27%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL206	P03372	Estrogen receptor alpha	910 nM; 909 nM	EC50; EC50	PMID: 23768907; via Super-PRED
CHEMBL242	Q92731	Estrogen receptor beta	1900 nM	EC50	PMID: 23768907

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	87.18%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.34%	96.09%
CHEMBL242	Q92731	Estrogen receptor beta	83.49%	98.35%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	82.85%	91.11%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	80.41%	85.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.29%	95.50%

Plants that contains it

• Dracocephalum ruyschiana
• Galeola faberi
• Gastrodia elata
• Xanthium strumarium

Cross-Links

• PubChem: 12111
• NPASS: NPC45040
• ChEMBL: CHEMBL138061
• LOTUS: LTS0060768
• wikiData: Q9658061