4,4'-Dihydroxy-3,5-dimethoxydihydrostilbene

Details

• Internal ID: 12f7c2f3-bf72-4032-8a49-e6ef91efd4e1
• Taxonomy: Phenylpropanoids and polyketides > Stilbenes
• IUPAC Name: 4-[2-(4-hydroxyphenyl)ethyl]-2,6-dimethoxyphenol
• SMILES (Canonical): COC1=CC(=CC(=C1O)OC)CCC2=CC=C(C=C2)O
• SMILES (Isomeric): COC1=CC(=CC(=C1O)OC)CCC2=CC=C(C=C2)O
• InChI: InChI=1S/C16H18O4/c1-19-14-9-12(10-15(20-2)16(14)18)4-3-11-5-7-13(17)8-6-11/h5-10,17-18H,3-4H2,1-2H3
• InChI Key: DLRAWGGINAZULN-UHFFFAOYSA-N
• Popularity: 8 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₈O₄
• Molecular Weight: 274.31 g/mol
• Exact Mass: 274.12050905 g/mol
• Topological Polar Surface Area (TPSA): 58.90 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 2.90
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

• 39499-96-2
• 4-[2-(4-hydroxyphenyl)ethyl]-2,6-dimethoxyphenol
• 4,4'-dihydroxy-3,5-dimethoxybibenzyl
• CHEBI:28571
• DTXSID90331916
• LMPK13090036
• Q27103778

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9659	96.59%
Caco-2	+	0.7799	77.99%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.8926	89.26%
OATP2B1 inhibitior	-	0.8410	84.10%
OATP1B1 inhibitior	+	0.8130	81.30%
OATP1B3 inhibitior	+	0.9413	94.13%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7318	73.18%
P-glycoprotein inhibitior	-	0.8074	80.74%
P-glycoprotein substrate	-	0.5112	51.12%
CYP3A4 substrate	-	0.5459	54.59%
CYP2C9 substrate	-	0.6120	61.20%
CYP2D6 substrate	+	0.5079	50.79%
CYP3A4 inhibition	-	0.8571	85.71%
CYP2C9 inhibition	+	0.5306	53.06%
CYP2C19 inhibition	+	0.8282	82.82%
CYP2D6 inhibition	-	0.7970	79.70%
CYP1A2 inhibition	+	0.8098	80.98%
CYP2C8 inhibition	+	0.9280	92.80%
CYP inhibitory promiscuity	+	0.7064	70.64%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7343	73.43%
Carcinogenicity (trinary)	Non-required	0.6672	66.72%
Eye corrosion	-	0.9386	93.86%
Eye irritation	+	0.8001	80.01%
Skin irritation	-	0.7361	73.61%
Skin corrosion	-	0.8856	88.56%
Ames mutagenesis	-	0.8800	88.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5743	57.43%
Micronuclear	-	0.6341	63.41%
Hepatotoxicity	-	0.7591	75.91%
skin sensitisation	-	0.7796	77.96%
Respiratory toxicity	-	0.7333	73.33%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	-	0.7875	78.75%
Nephrotoxicity	-	0.8250	82.50%
Acute Oral Toxicity (c)	III	0.7658	76.58%
Estrogen receptor binding	+	0.7105	71.05%
Androgen receptor binding	+	0.7420	74.20%
Thyroid receptor binding	+	0.8745	87.45%
Glucocorticoid receptor binding	+	0.6639	66.39%
Aromatase binding	-	0.5550	55.50%
PPAR gamma	+	0.6600	66.00%
Honey bee toxicity	-	0.8774	87.74%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.6951	69.51%
Fish aquatic toxicity	+	0.9082	90.82%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.91%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.80%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.32%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.72%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.06%	99.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.97%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.88%	94.45%
CHEMBL2535	P11166	Glucose transporter	85.34%	98.75%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.31%	94.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.80%	95.89%
CHEMBL1255126	O15151	Protein Mdm4	84.75%	90.20%
CHEMBL4208	P20618	Proteasome component C5	84.34%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.16%	95.89%

Plants that contains it

• Combretum psidioides
• Dendrobium moniliforme

Cross-Links

• PubChem: 442701
• LOTUS: LTS0147627
• wikiData: Q27103778