3-methoxy-5-[(E)-2-phenylethenyl]benzene-1,2-diol

Details

• Internal ID: 49e848d1-d423-4b9b-8aa7-28a75b8f985e
• Taxonomy: Phenylpropanoids and polyketides > Stilbenes
• IUPAC Name: 3-methoxy-5-[(E)-2-phenylethenyl]benzene-1,2-diol
• SMILES (Canonical): COC1=CC(=CC(=C1O)O)C=CC2=CC=CC=C2
• SMILES (Isomeric): COC1=CC(=CC(=C1O)O)/C=C/C2=CC=CC=C2
• InChI: InChI=1S/C15H14O3/c1-18-14-10-12(9-13(16)15(14)17)8-7-11-5-3-2-4-6-11/h2-10,16-17H,1H3/b8-7+
• InChI Key: WBBHYMRWGHBXLS-BQYQJAHWSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₄O₃
• Molecular Weight: 242.27 g/mol
• Exact Mass: 242.094294304 g/mol
• Topological Polar Surface Area (TPSA): 49.70 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 3.28
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• SCHEMBL3645729
• ACon1_000674
• DTXSID501341856
• NCGC00169470-01
• 3-methoxy-5-[(E)-2-phenylethenyl]benzene-1,2-diol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9895	98.95%
Caco-2	-	0.5594	55.94%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7471	74.71%
OATP2B1 inhibitior	-	0.8554	85.54%
OATP1B1 inhibitior	+	0.8955	89.55%
OATP1B3 inhibitior	+	0.9879	98.79%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.6425	64.25%
P-glycoprotein inhibitior	-	0.8112	81.12%
P-glycoprotein substrate	-	0.9593	95.93%
CYP3A4 substrate	-	0.6674	66.74%
CYP2C9 substrate	-	0.5969	59.69%
CYP2D6 substrate	-	0.6932	69.32%
CYP3A4 inhibition	-	0.8672	86.72%
CYP2C9 inhibition	-	0.5475	54.75%
CYP2C19 inhibition	+	0.5260	52.60%
CYP2D6 inhibition	-	0.9185	91.85%
CYP1A2 inhibition	+	0.8833	88.33%
CYP2C8 inhibition	+	0.7394	73.94%
CYP inhibitory promiscuity	+	0.7310	73.10%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7594	75.94%
Carcinogenicity (trinary)	Non-required	0.4615	46.15%
Eye corrosion	-	0.9405	94.05%
Eye irritation	+	0.9669	96.69%
Skin irritation	+	0.5214	52.14%
Skin corrosion	-	0.6697	66.97%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6205	62.05%
Micronuclear	+	0.6700	67.00%
Hepatotoxicity	+	0.5586	55.86%
skin sensitisation	+	0.5595	55.95%
Respiratory toxicity	-	0.7222	72.22%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	-	0.8375	83.75%
Nephrotoxicity	-	0.7743	77.43%
Acute Oral Toxicity (c)	III	0.6278	62.78%
Estrogen receptor binding	+	0.9079	90.79%
Androgen receptor binding	+	0.8111	81.11%
Thyroid receptor binding	+	0.7000	70.00%
Glucocorticoid receptor binding	+	0.7341	73.41%
Aromatase binding	+	0.8232	82.32%
PPAR gamma	+	0.8733	87.33%
Honey bee toxicity	-	0.9498	94.98%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.7000	70.00%
Fish aquatic toxicity	+	0.9716	97.16%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.78%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.05%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.82%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.02%	86.33%
CHEMBL3194	P02766	Transthyretin	92.00%	90.71%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	88.00%	94.08%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.35%	96.09%
CHEMBL3192	Q9BY41	Histone deacetylase 8	84.50%	93.99%
CHEMBL1255126	O15151	Protein Mdm4	84.09%	90.20%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.62%	89.62%
CHEMBL3401	O75469	Pregnane X receptor	83.55%	94.73%
CHEMBL2002	P12268	Inosine-5'-monophosphate dehydrogenase 2	82.04%	98.21%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	80.16%	94.62%

Plants that contains it

• Alnus alnobetula subsp. fruticosa
• Brassica napus

Cross-Links

• PubChem: 24148525
• LOTUS: LTS0177882
• wikiData: Q105300616