3-(1,3-benzodioxol-5-yl)-N-[2-(4-methoxyphenyl)ethyl]prop-2-enamide

Details

• Internal ID: 398bb703-e5f3-471d-b86f-09fd1a9a99f4
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Cinnamic acid amides
• IUPAC Name: 3-(1,3-benzodioxol-5-yl)-N-[2-(4-methoxyphenyl)ethyl]prop-2-enamide
• SMILES (Canonical): COC1=CC=C(C=C1)CCNC(=O)C=CC2=CC3=C(C=C2)OCO3
• SMILES (Isomeric): COC1=CC=C(C=C1)CCNC(=O)C=CC2=CC3=C(C=C2)OCO3
• InChI: InChI=1S/C19H19NO4/c1-22-16-6-2-14(3-7-16)10-11-20-19(21)9-5-15-4-8-17-18(12-15)24-13-23-17/h2-9,12H,10-11,13H2,1H3,(H,20,21)
• InChI Key: ZDVBEJSAKORDPK-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₉NO₄
• Molecular Weight: 325.40 g/mol
• Exact Mass: 325.13140809 g/mol
• Topological Polar Surface Area (TPSA): 56.80 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 2.80
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9953	99.53%
Caco-2	+	0.8004	80.04%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.5685	56.85%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9204	92.04%
OATP1B3 inhibitior	+	0.9533	95.33%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.9155	91.55%
P-glycoprotein inhibitior	+	0.6114	61.14%
P-glycoprotein substrate	-	0.6002	60.02%
CYP3A4 substrate	+	0.5406	54.06%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8143	81.43%
CYP3A4 inhibition	+	0.8693	86.93%
CYP2C9 inhibition	+	0.6237	62.37%
CYP2C19 inhibition	+	0.7428	74.28%
CYP2D6 inhibition	+	0.6841	68.41%
CYP1A2 inhibition	+	0.7283	72.83%
CYP2C8 inhibition	+	0.5229	52.29%
CYP inhibitory promiscuity	+	0.9210	92.10%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.4833	48.33%
Eye corrosion	-	0.9856	98.56%
Eye irritation	-	0.8731	87.31%
Skin irritation	-	0.7367	73.67%
Skin corrosion	-	0.9356	93.56%
Ames mutagenesis	-	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8585	85.85%
Micronuclear	+	0.6100	61.00%
Hepatotoxicity	-	0.6500	65.00%
skin sensitisation	-	0.8136	81.36%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.8828	88.28%
Acute Oral Toxicity (c)	III	0.6065	60.65%
Estrogen receptor binding	+	0.5728	57.28%
Androgen receptor binding	+	0.9311	93.11%
Thyroid receptor binding	+	0.6152	61.52%
Glucocorticoid receptor binding	+	0.6589	65.89%
Aromatase binding	+	0.6764	67.64%
PPAR gamma	-	0.5095	50.95%
Honey bee toxicity	-	0.8716	87.16%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	-	0.3963	39.63%

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	99.10%	91.11%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	97.65%	96.77%
CHEMBL2039	P27338	Monoamine oxidase B	96.79%	92.51%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.43%	96.09%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	96.10%	94.80%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.93%	96.00%
CHEMBL2581	P07339	Cathepsin D	95.83%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.41%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.37%	86.33%
CHEMBL4208	P20618	Proteasome component C5	95.08%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.42%	99.17%
CHEMBL240	Q12809	HERG	93.29%	89.76%
CHEMBL5261	Q7L7X3	Serine/threonine-protein kinase TAO1	92.21%	89.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	90.82%	92.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.35%	95.56%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	89.53%	95.50%
CHEMBL5701	Q9H2K8	Serine/threonine-protein kinase TAO3	88.48%	96.67%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	87.30%	80.96%
CHEMBL3401	O75469	Pregnane X receptor	86.15%	94.73%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.23%	96.95%
CHEMBL3492	P49721	Proteasome Macropain subunit	83.59%	90.24%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	83.57%	85.30%
CHEMBL3437	Q16853	Amine oxidase, copper containing	83.41%	94.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.23%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.74%	89.00%
CHEMBL2535	P11166	Glucose transporter	82.69%	98.75%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.59%	97.09%

Plants that contains it

• Zanthoxylum armatum

Cross-Links

• PubChem: 882950
• LOTUS: LTS0207584
• wikiData: Q105372739