(E)-3,3',4,5'-Tetramethoxystilbene

Details

• Internal ID: a955c2a9-49ad-4ebd-960e-56f93a9a427a
• Taxonomy: Phenylpropanoids and polyketides > Stilbenes
• IUPAC Name: 1-[(E)-2-(3,4-dimethoxyphenyl)ethenyl]-3,5-dimethoxybenzene
• SMILES (Canonical): COC1=C(C=C(C=C1)C=CC2=CC(=CC(=C2)OC)OC)OC
• SMILES (Isomeric): COC1=C(C=C(C=C1)/C=C/C2=CC(=CC(=C2)OC)OC)OC
• InChI: InChI=1S/C18H20O4/c1-19-15-9-14(10-16(12-15)20-2)6-5-13-7-8-17(21-3)18(11-13)22-4/h5-12H,1-4H3/b6-5+
• InChI Key: PTVAOGIYBMTHSN-AATRIKPKSA-N
• Popularity: 18 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₀O₄
• Molecular Weight: 300.30 g/mol
• Exact Mass: 300.13615911 g/mol
• Topological Polar Surface Area (TPSA): 36.90 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 3.89
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 6

Synonyms

• (E)-3,4,3',5'-TETRAMETHOXYSTILBENE
• 1-((E)-2-(3,4-dimethoxyphenyl)ethenyl)-3,5-dimethoxybenzene
• RefChem:906369
• 83088-26-0
• (E)-3,3',4,5'-TETRAMETHOXYSTILBENE
• 4-(3,5-Dimethoxystyryl)-1,2-dimethoxybenzene
• 3,3',4,5'-Tetramethoxypiceatannol
• (E)-4-(3,5-Dimethoxystyryl)-1,2-dimethoxybenzene
• MFCD09033675
• NSC622473
• CHEMBL44509
• (E)-3,5,30,40-Tetramethoxystilbene
• 1-[(E)-2-(3,4-dimethoxyphenyl)vinyl]-3,5-dimethoxy-benzene
• 1-[(1E)-2-(3,4-dimethoxyphenyl)ethenyl]-3,5-dimethoxybenzene
• 20767-18-4
• SCHEMBL1394568
• DTXSID101185371
• BDBM50085526
• (E)3,3',4,5'-Tetramethoxystilbene
• AKOS015915177
• NSC-622473
• trans-3,3',4,5'-Tetramethoxystilbene
• trans-3,5,3',4'-tetramethoxystilbene
• 3,3',4,5'-Tetramethoxy-trans-stilbene
• AC-24231
• AS-66223
• SY056282
• CS-0150476
• T2842
• T72978
• 4-(2-(3,5-Dimethoxyphenyl)vinyl)-1,2-dimethoxybenzene
• 4-[(E)-2-(3,5-dimethoxyphenyl)vinyl]-1,2-dimethoxybenzene
• 4-[(1E)-2-(3,5-Dimethoxyphenyl)ethenyl]-1,2-dimethoxybenzene
• 4-[2-(3,5-dimethoxyphenyl)-(E)-1-ethenyl]-1,2-dimethoxybenzene
• 3,3 inverted exclamation mark ,4,5 inverted exclamation mark -Tetramethoxypiceatannol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9948	99.48%
Caco-2	+	0.9253	92.53%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.8429	84.29%
Subcellular localzation	Mitochondria	0.7145	71.45%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9544	95.44%
OATP1B3 inhibitior	+	0.9837	98.37%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.6500	65.00%
P-glycoprotein inhibitior	-	0.5973	59.73%
P-glycoprotein substrate	-	0.9432	94.32%
CYP3A4 substrate	-	0.6443	64.43%
CYP2C9 substrate	-	0.5886	58.86%
CYP2D6 substrate	+	0.3530	35.30%
CYP3A4 inhibition	+	0.6347	63.47%
CYP2C9 inhibition	-	0.9532	95.32%
CYP2C19 inhibition	+	0.5410	54.10%
CYP2D6 inhibition	-	0.9199	91.99%
CYP1A2 inhibition	+	0.8813	88.13%
CYP2C8 inhibition	-	0.5843	58.43%
CYP inhibitory promiscuity	+	0.8763	87.63%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7621	76.21%
Carcinogenicity (trinary)	Non-required	0.5189	51.89%
Eye corrosion	-	0.9586	95.86%
Eye irritation	+	0.9107	91.07%
Skin irritation	-	0.8376	83.76%
Skin corrosion	-	0.9825	98.25%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7462	74.62%
Micronuclear	-	0.5667	56.67%
Hepatotoxicity	+	0.5641	56.41%
skin sensitisation	-	0.8033	80.33%
Respiratory toxicity	-	0.8778	87.78%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	-	0.8500	85.00%
Nephrotoxicity	-	0.6126	61.26%
Acute Oral Toxicity (c)	III	0.5925	59.25%
Estrogen receptor binding	+	0.8287	82.87%
Androgen receptor binding	+	0.6171	61.71%
Thyroid receptor binding	+	0.6716	67.16%
Glucocorticoid receptor binding	+	0.5742	57.42%
Aromatase binding	+	0.7042	70.42%
PPAR gamma	-	0.6786	67.86%
Honey bee toxicity	-	0.8999	89.99%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.7900	79.00%
Fish aquatic toxicity	+	0.9853	98.53%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2231	P04798	Cytochrome P450 1A1	750 nM	IC50	PMID: 15217276
CHEMBL4878	Q16678	Cytochrome P450 1B1	3000 nM	IC50	PMID: 20050684
CHEMBL3959	P16083	Quinone reductase 2	37100 nM	IC50	PMID: 11754615

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	97.22%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.31%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.24%	86.33%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	90.82%	92.68%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.81%	96.09%
CHEMBL2487	P05067	Beta amyloid A4 protein	85.63%	96.74%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	84.53%	92.38%
CHEMBL1907599	P05556	Integrin alpha-4/beta-1	83.99%	92.86%
CHEMBL4208	P20618	Proteasome component C5	83.21%	90.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.17%	89.62%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	81.41%	91.11%
CHEMBL2535	P11166	Glucose transporter	80.98%	98.75%
CHEMBL3194	P02766	Transthyretin	80.46%	90.71%
CHEMBL1929	P47989	Xanthine dehydrogenase	80.24%	96.12%

Plants that contains it

• Rheum rhabarbarum
• Schoenus nigricans

Cross-Links

• PubChem: 5387294
• NPASS: NPC123948
• ChEMBL: CHEMBL44509
• LOTUS: LTS0234261
• wikiData: Q105214900