3-Methoxy-2-(3-methyl-2-butenyl)-5-(2-phenylethenyl)phenol

Details

• Internal ID: 3b9b7bf8-1f23-47bd-a432-32dc91ad5491
• Taxonomy: Phenylpropanoids and polyketides > Stilbenes
• IUPAC Name: 3-methoxy-2-(3-methylbut-2-enyl)-5-(2-phenylethenyl)phenol
• SMILES (Canonical): CC(=CCC1=C(C=C(C=C1OC)C=CC2=CC=CC=C2)O)C
• SMILES (Isomeric): CC(=CCC1=C(C=C(C=C1OC)C=CC2=CC=CC=C2)O)C
• InChI: InChI=1S/C20H22O2/c1-15(2)9-12-18-19(21)13-17(14-20(18)22-3)11-10-16-7-5-4-6-8-16/h4-11,13-14,21H,12H2,1-3H3
• InChI Key: MPDBOKIOROLWQP-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₂O₂
• Molecular Weight: 294.40 g/mol
• Exact Mass: 294.161979940 g/mol
• Topological Polar Surface Area (TPSA): 29.50 Ų
• XlogP: 5.70
• Atomic LogP (AlogP): 5.08
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

• 3-methoxy-2-(3-methyl-2-butenyl)-5-(2-phenylethenyl)phenol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.7512	75.12%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7760	77.60%
OATP2B1 inhibitior	-	0.8541	85.41%
OATP1B1 inhibitior	+	0.8927	89.27%
OATP1B3 inhibitior	+	0.9264	92.64%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8520	85.20%
P-glycoprotein inhibitior	+	0.6234	62.34%
P-glycoprotein substrate	-	0.8936	89.36%
CYP3A4 substrate	-	0.5821	58.21%
CYP2C9 substrate	+	0.6048	60.48%
CYP2D6 substrate	+	0.3626	36.26%
CYP3A4 inhibition	-	0.8602	86.02%
CYP2C9 inhibition	-	0.5897	58.97%
CYP2C19 inhibition	+	0.8529	85.29%
CYP2D6 inhibition	-	0.7983	79.83%
CYP1A2 inhibition	+	0.6686	66.86%
CYP2C8 inhibition	+	0.6570	65.70%
CYP inhibitory promiscuity	+	0.8812	88.12%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7126	71.26%
Carcinogenicity (trinary)	Non-required	0.6778	67.78%
Eye corrosion	-	0.9867	98.67%
Eye irritation	+	0.7361	73.61%
Skin irritation	-	0.8032	80.32%
Skin corrosion	-	0.9374	93.74%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8372	83.72%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	-	0.5500	55.00%
skin sensitisation	+	0.5936	59.36%
Respiratory toxicity	-	0.6333	63.33%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	-	0.6750	67.50%
Nephrotoxicity	-	0.7405	74.05%
Acute Oral Toxicity (c)	III	0.8301	83.01%
Estrogen receptor binding	+	0.9322	93.22%
Androgen receptor binding	+	0.8447	84.47%
Thyroid receptor binding	+	0.7406	74.06%
Glucocorticoid receptor binding	+	0.7600	76.00%
Aromatase binding	+	0.8216	82.16%
PPAR gamma	+	0.9464	94.64%
Honey bee toxicity	-	0.8860	88.60%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.9940	99.40%

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	98.50%	91.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	97.27%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.23%	86.33%
CHEMBL3192	Q9BY41	Histone deacetylase 8	93.25%	93.99%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.91%	95.56%
CHEMBL2581	P07339	Cathepsin D	90.97%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	88.74%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.75%	96.09%
CHEMBL3194	P02766	Transthyretin	86.03%	90.71%
CHEMBL221	P23219	Cyclooxygenase-1	84.58%	90.17%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	83.26%	92.68%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.86%	99.17%
CHEMBL1951	P21397	Monoamine oxidase A	80.40%	91.49%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.02%	89.62%

Plants that contains it

• Cajanus cajan

Cross-Links

• PubChem: 69713319
• LOTUS: LTS0052480
• wikiData: Q105169382