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

Details

• Internal ID: 79d9f33c-c2c2-4ff1-aad8-d3a60fd2d6c3
• Taxonomy: Phenylpropanoids and polyketides > Stilbenes
• IUPAC Name: 1,3-dimethoxy-5-[(E)-2-(4-methoxyphenyl)ethenyl]benzene
• SMILES (Canonical): COC1=CC=C(C=C1)C=CC2=CC(=CC(=C2)OC)OC
• SMILES (Isomeric): COC1=CC=C(C=C1)/C=C/C2=CC(=CC(=C2)OC)OC
• InChI: InChI=1S/C17H18O3/c1-18-15-8-6-13(7-9-15)4-5-14-10-16(19-2)12-17(11-14)20-3/h4-12H,1-3H3/b5-4+
• InChI Key: GDHNBPHYVRHYCC-SNAWJCMRSA-N
• Popularity: 81 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₈O₃
• Molecular Weight: 270.32 g/mol
• Exact Mass: 270.125594432 g/mol
• Topological Polar Surface Area (TPSA): 27.70 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 3.88
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 5

Synonyms

• trans-Trimethoxyresveratrol
• 3,4',5-trimethoxy-trans-stilbene
• (E)-1,3-Dimethoxy-5-(4-methoxystyryl)benzene
• (E)-3,5,4'-Trimethoxystilbene
• 3,4',5-trimethoxystilbene
• 3,5,4'-trimethoxystilbene
• TRIMETHOXYSTILBENE
• E-Resveratrol trimethyl ether
• 1,3-dimethoxy-5-[(E)-2-(4-methoxyphenyl)ethenyl]benzene
• TRISMETHOXYRESVERATROL
• CHEMBL296411
• trans-3,4',5-trimethoxystilbene
• 1,3-dimethoxy-5-[(E)-2-(4-methoxyphenyl)vinyl]benzene
• (E)-3,4',5-Trimethoxystilbene
• (Z)-3,5,4'-TRIMETHOXYSTILBENE
• Tri-O-methylresveratrol
• 3,4`,5-Trimethoxy-trans-stilbene
• NSC631363
• D0O9NE
• SCHEMBL918739
• SCHEMBL918740
• trans-Stilbene Derivative, 4a
• MR-3
• 5-[2-(4-Methoxyphenyl)Ethenyl]-1,3-Dimethoxy Benzene
• 8E-3,4',5-trimethoxystilbene
• BDBM23928
• AMY5759
• trans-3,5,4'-trimethoxystilbene
• (E)-3,5,40-Trimethoxystilbene
• 1,3-Dimethoxy-5-[(1E)-2-(4-methoxyphenyl)ethenyl]benzene
• DTXSID701034889
• HY-N1408
• MFCD02093500
• s3888
• AKOS015915036
• AC-7024
• CCG-267163
• CS-5797
• NSC-631363
• AS-19232
• T1829
• A816066
• J-014611
• Z2216901131
• trans-1-(3,5-Dimethoxyphenyl)-2-(4-methoxyphenyl)ethylene
• Benzene, 1,3-dimethoxy-5-[(E)-2-(4-methoxyphenyl)ethenyl]-
• Benzene,1,3-dimethoxy-5-[(1E)-2-(4-methoxyphenyl)ethenyl]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.8833	88.33%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7925	79.25%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9570	95.70%
OATP1B3 inhibitior	+	0.9769	97.69%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.5797	57.97%
P-glycoprotein inhibitior	-	0.7372	73.72%
P-glycoprotein substrate	-	0.9839	98.39%
CYP3A4 substrate	-	0.6948	69.48%
CYP2C9 substrate	-	0.5886	58.86%
CYP2D6 substrate	+	0.3530	35.30%
CYP3A4 inhibition	-	0.5097	50.97%
CYP2C9 inhibition	-	0.9542	95.42%
CYP2C19 inhibition	+	0.5506	55.06%
CYP2D6 inhibition	-	0.9348	93.48%
CYP1A2 inhibition	+	0.8403	84.03%
CYP2C8 inhibition	-	0.8372	83.72%
CYP inhibitory promiscuity	+	0.8246	82.46%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.5979	59.79%
Carcinogenicity (trinary)	Non-required	0.5411	54.11%
Eye corrosion	-	0.9453	94.53%
Eye irritation	+	0.9415	94.15%
Skin irritation	-	0.8085	80.85%
Skin corrosion	-	0.9910	99.10%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6486	64.86%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	+	0.5033	50.33%
skin sensitisation	-	0.7165	71.65%
Respiratory toxicity	-	0.8889	88.89%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	-	0.8500	85.00%
Nephrotoxicity	+	0.4613	46.13%
Acute Oral Toxicity (c)	III	0.6106	61.06%
Estrogen receptor binding	+	0.8384	83.84%
Androgen receptor binding	+	0.7118	71.18%
Thyroid receptor binding	+	0.5909	59.09%
Glucocorticoid receptor binding	+	0.6504	65.04%
Aromatase binding	+	0.8370	83.70%
PPAR gamma	-	0.5057	50.57%
Honey bee toxicity	-	0.9338	93.38%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.8400	84.00%
Fish aquatic toxicity	+	0.9663	96.63%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	760 nM	IC50	via Super-PRED
CHEMBL2096618	P11274	Bcr/Abl fusion protein	10000 nM	IC50	PMID: 16686543
CHEMBL230	P35354	Cyclooxygenase-2	1667 nM	IC50	PMID: 26850006
CHEMBL2231	P04798	Cytochrome P450 1A1	830 nM	IC50	PMID: 11754588
CHEMBL3356	P05177	Cytochrome P450 1A2	6200 nM	IC50	PMID: 11754588
CHEMBL4878	Q16678	Cytochrome P450 1B1	790 nM	IC50	PMID: 11754588
CHEMBL206	P03372	Estrogen receptor alpha	261 nM; 261 nM; 132 nM	Ki; Ki; Ki	PMID: 15634023; via Super-PRED; via Super-PRED
CHEMBL4302	P08183	P-glycoprotein 1	8000 nM	IC50	PMID: 16686543
CHEMBL3959	P16083	Quinone reductase 2	14600 nM	IC50	PMID: 23953689

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.03%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.69%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.26%	91.11%
CHEMBL2487	P05067	Beta amyloid A4 protein	89.18%	96.74%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.66%	86.33%
CHEMBL3192	Q9BY41	Histone deacetylase 8	88.42%	93.99%
CHEMBL4208	P20618	Proteasome component C5	86.66%	90.00%
CHEMBL1929	P47989	Xanthine dehydrogenase	86.45%	96.12%
CHEMBL1907	P15144	Aminopeptidase N	85.95%	93.31%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.88%	96.09%
CHEMBL3492	P49721	Proteasome Macropain subunit	82.36%	90.24%
CHEMBL1907599	P05556	Integrin alpha-4/beta-1	82.17%	92.86%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	80.56%	100.00%

Plants that contains it

• Dalea versicolor
• Rheum rhabarbarum
• Schoenus nigricans
• Scirpoides holoschoenus
• Virola elongata

Cross-Links

• PubChem: 5388063
• NPASS: NPC82016
• ChEMBL: CHEMBL296411
• LOTUS: LTS0113783
• wikiData: Q76306144