2,3-Dimethoxy-4-[3-(2-methoxyphenyl)prop-2-en-1-yl]phenol

Details

• Internal ID: ef2e8c19-dec2-4af5-9917-af1271fb64b3
• Taxonomy: Phenylpropanoids and polyketides > Linear 1,3-diarylpropanoids > Cinnamylphenols
• IUPAC Name: 2,3-dimethoxy-4-[3-(2-methoxyphenyl)prop-2-enyl]phenol
• SMILES (Canonical): COC1=CC=CC=C1C=CCC2=C(C(=C(C=C2)O)OC)OC
• SMILES (Isomeric): COC1=CC=CC=C1C=CCC2=C(C(=C(C=C2)O)OC)OC
• InChI: InChI=1S/C18H20O4/c1-20-16-10-5-4-7-13(16)8-6-9-14-11-12-15(19)18(22-3)17(14)21-2/h4-8,10-12,19H,9H2,1-3H3
• InChI Key: NARXDKNFDGSLCT-UHFFFAOYSA-N
• Popularity: 0 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): 47.90 Ų
• XlogP: 4.00
• Atomic LogP (AlogP): 3.67
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

• 2,3-Dimethoxy-4-[3-(2-methoxyphenyl)prop-2-en-1-yl]phenol
• 20362-18-9

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9869	98.69%
Caco-2	+	0.9197	91.97%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7462	74.62%
OATP2B1 inhibitior	-	0.8601	86.01%
OATP1B1 inhibitior	+	0.8587	85.87%
OATP1B3 inhibitior	+	0.9405	94.05%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.5868	58.68%
P-glycoprotein inhibitior	-	0.6191	61.91%
P-glycoprotein substrate	-	0.8976	89.76%
CYP3A4 substrate	-	0.5618	56.18%
CYP2C9 substrate	+	0.5888	58.88%
CYP2D6 substrate	+	0.4021	40.21%
CYP3A4 inhibition	-	0.6482	64.82%
CYP2C9 inhibition	-	0.9009	90.09%
CYP2C19 inhibition	+	0.6592	65.92%
CYP2D6 inhibition	-	0.8160	81.60%
CYP1A2 inhibition	+	0.5777	57.77%
CYP2C8 inhibition	+	0.5695	56.95%
CYP inhibitory promiscuity	+	0.8227	82.27%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.7721	77.21%
Carcinogenicity (trinary)	Non-required	0.5912	59.12%
Eye corrosion	-	0.9782	97.82%
Eye irritation	-	0.4830	48.30%
Skin irritation	-	0.8146	81.46%
Skin corrosion	-	0.9678	96.78%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7383	73.83%
Micronuclear	-	0.5208	52.08%
Hepatotoxicity	-	0.5073	50.73%
skin sensitisation	-	0.6988	69.88%
Respiratory toxicity	-	0.8000	80.00%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	-	0.8500	85.00%
Nephrotoxicity	-	0.6294	62.94%
Acute Oral Toxicity (c)	III	0.7153	71.53%
Estrogen receptor binding	+	0.9179	91.79%
Androgen receptor binding	+	0.5676	56.76%
Thyroid receptor binding	+	0.6939	69.39%
Glucocorticoid receptor binding	+	0.6808	68.08%
Aromatase binding	+	0.7315	73.15%
PPAR gamma	+	0.5982	59.82%
Honey bee toxicity	-	0.9004	90.04%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.6700	67.00%
Fish aquatic toxicity	+	0.9790	97.90%

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	98.57%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.31%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.96%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.30%	96.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	91.66%	89.62%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.43%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.96%	99.17%
CHEMBL1255126	O15151	Protein Mdm4	86.77%	90.20%
CHEMBL3192	Q9BY41	Histone deacetylase 8	85.28%	93.99%
CHEMBL2535	P11166	Glucose transporter	82.53%	98.75%
CHEMBL4355	O14976	Serine/threonine-protein kinase GAK	82.36%	89.32%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.88%	95.50%
CHEMBL2581	P07339	Cathepsin D	80.14%	98.95%

Plants that contains it

• Machaerium mucronulatum

Cross-Links

• PubChem: 53440675
• LOTUS: LTS0261391
• wikiData: Q82634699