5-[(1E)-2-(3,4-dimethoxyphenyl)ethenyl]-1,3-Benzenediol

Details

• Internal ID: 498b0ef2-37a2-484e-a8f4-e9a9d2692f05
• Taxonomy: Phenylpropanoids and polyketides > Stilbenes
• IUPAC Name: 5-[(E)-2-(3,4-dimethoxyphenyl)ethenyl]benzene-1,3-diol
• SMILES (Canonical): COC1=C(C=C(C=C1)C=CC2=CC(=CC(=C2)O)O)OC
• SMILES (Isomeric): COC1=C(C=C(C=C1)/C=C/C2=CC(=CC(=C2)O)O)OC
• InChI: InChI=1S/C16H16O4/c1-19-15-6-5-11(9-16(15)20-2)3-4-12-7-13(17)10-14(18)8-12/h3-10,17-18H,1-2H3/b4-3+
• InChI Key: WHKSEHKYYXHCTA-ONEGZZNKSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₆O₄
• Molecular Weight: 272.29 g/mol
• Exact Mass: 272.10485899 g/mol
• Topological Polar Surface Area (TPSA): 58.90 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 3.29
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• 5-[(1E)-2-(3,4-dimethoxyphenyl)ethenyl]-1,3-Benzenediol
• CHEMBL473518
• 5-((1E)-2-(3,4-Dimethoxyphenyl)ethenyl)-1,3-benzenediol
• Gnetucleistol E
• Y5XLT99N4N
• SCHEMBL10307426
• 3,4-Dimethoxystilbene-3',5'-diol
• BDBM50247221
• AKOS015915151
• AC-24230
• 5-(3,4-dimethoxystyryl)benzene-1,3-diol
• (E)-3,4-Dimethoxy-stilbene-3',5'-diol
• trans-3,5-dihydroxy-3',4'-dimethoxystilbene
• 5-[2-(3,4-Dimethoxyphenyl)ethenyl]-1,3-benzenediol
• 1,3-Benzenediol, 5-[2-(3,4-dimethoxyphenyl)ethenyl]-
• 5-(1E)-2-(3,4-Dimethoxyphenyl)ethenyl-1,3-benzenediol
• 1,3-Benzenediol, 5-[(1E)-2-(3,4-dimethoxyphenyl)ethenyl]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9664	96.64%
Caco-2	+	0.9207	92.07%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.5927	59.27%
OATP2B1 inhibitior	-	0.8592	85.92%
OATP1B1 inhibitior	+	0.9518	95.18%
OATP1B3 inhibitior	+	0.9713	97.13%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9338	93.38%
BSEP inhibitior	-	0.4714	47.14%
P-glycoprotein inhibitior	-	0.8116	81.16%
P-glycoprotein substrate	-	0.9388	93.88%
CYP3A4 substrate	-	0.6346	63.46%
CYP2C9 substrate	-	0.5963	59.63%
CYP2D6 substrate	-	0.6581	65.81%
CYP3A4 inhibition	+	0.6243	62.43%
CYP2C9 inhibition	+	0.6560	65.60%
CYP2C19 inhibition	+	0.7104	71.04%
CYP2D6 inhibition	-	0.8221	82.21%
CYP1A2 inhibition	+	0.8923	89.23%
CYP2C8 inhibition	+	0.6226	62.26%
CYP inhibitory promiscuity	+	0.8673	86.73%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8094	80.94%
Carcinogenicity (trinary)	Non-required	0.6510	65.10%
Eye corrosion	-	0.9601	96.01%
Eye irritation	+	0.9194	91.94%
Skin irritation	-	0.6832	68.32%
Skin corrosion	-	0.7190	71.90%
Ames mutagenesis	-	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3837	38.37%
Micronuclear	+	0.5900	59.00%
Hepatotoxicity	-	0.5772	57.72%
skin sensitisation	+	0.5000	50.00%
Respiratory toxicity	-	0.8111	81.11%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	-	0.7375	73.75%
Nephrotoxicity	-	0.5738	57.38%
Acute Oral Toxicity (c)	III	0.6997	69.97%
Estrogen receptor binding	+	0.8030	80.30%
Androgen receptor binding	+	0.6225	62.25%
Thyroid receptor binding	+	0.6988	69.88%
Glucocorticoid receptor binding	-	0.4652	46.52%
Aromatase binding	+	0.7918	79.18%
PPAR gamma	+	0.6341	63.41%
Honey bee toxicity	-	0.9281	92.81%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.9733	97.33%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL221	P23219	Cyclooxygenase-1	290 nM	IC50	via CMAUP
CHEMBL230	P35354	Cyclooxygenase-2	21300 nM	IC50	PMID: 23465614
CHEMBL2231	P04798	Cytochrome P450 1A1	90 nM	Ki	PMID: 8158155

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.18%	96.00%
CHEMBL3194	P02766	Transthyretin	93.95%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.04%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.33%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.01%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.54%	96.09%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	86.96%	89.62%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.35%	92.94%
CHEMBL1255126	O15151	Protein Mdm4	83.94%	90.20%
CHEMBL2535	P11166	Glucose transporter	83.77%	98.75%
CHEMBL4208	P20618	Proteasome component C5	82.32%	90.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.88%	89.00%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	80.99%	92.68%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.78%	99.17%
CHEMBL1951	P21397	Monoamine oxidase A	80.14%	91.49%

Plants that contains it

• Stuhlmannia moavi

Cross-Links

• PubChem: 44563762
• NPASS: NPC474565
• ChEMBL: CHEMBL473518