3-Benzo[1,3]dioxol-5-yl-1-(4-methyl-piperidin-1-yl)-propenone

Details

• Internal ID: 136ef790-56fa-4322-bf47-cc0274396a82
• Taxonomy: Organoheterocyclic compounds > Benzodioxoles
• IUPAC Name: (E)-3-(1,3-benzodioxol-5-yl)-1-(4-methylpiperidin-1-yl)prop-2-en-1-one
• SMILES (Canonical): CC1CCN(CC1)C(=O)C=CC2=CC3=C(C=C2)OCO3
• SMILES (Isomeric): CC1CCN(CC1)C(=O)/C=C/C2=CC3=C(C=C2)OCO3
• InChI: InChI=1S/C16H19NO3/c1-12-6-8-17(9-7-12)16(18)5-3-13-2-4-14-15(10-13)20-11-19-14/h2-5,10,12H,6-9,11H2,1H3/b5-3+
• InChI Key: BIXTXZXWPUQSJC-HWKANZROSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₉NO₃
• Molecular Weight: 273.33 g/mol
• Exact Mass: 273.13649347 g/mol
• Topological Polar Surface Area (TPSA): 38.80 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 2.69
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• 290835-22-2
• 3-Benzo[1,3]dioxol-5-yl-1-(4-methyl-piperidin-1-yl)-propenone
• 3-(Benzo[d][1,3]dioxol-5-yl)-1-(4-methylpiperidin-1-yl)prop-2-en-1-one
• SCHEMBL3123624
• HMS1475K13
• BDBM50401984
• STL482922
• AKOS001426575
• IDI1_019903
• SR-01000404724
• SR-01000404724-1
• BRD-K22440539-001-01-5
• Z32665399
• (2E)-3-(1,3-benzodioxol-5-yl)-1-(4-methylpiperidin-1-yl)prop-2-en-1-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9948	99.48%
Caco-2	+	0.9446	94.46%
Blood Brain Barrier	+	0.9500	95.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.4985	49.85%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9505	95.05%
OATP1B3 inhibitior	+	0.9494	94.94%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	-	0.4938	49.38%
P-glycoprotein inhibitior	-	0.8973	89.73%
P-glycoprotein substrate	-	0.8362	83.62%
CYP3A4 substrate	-	0.5578	55.78%
CYP2C9 substrate	-	0.6314	63.14%
CYP2D6 substrate	-	0.8701	87.01%
CYP3A4 inhibition	+	0.5349	53.49%
CYP2C9 inhibition	-	0.8746	87.46%
CYP2C19 inhibition	-	0.5678	56.78%
CYP2D6 inhibition	+	0.7505	75.05%
CYP1A2 inhibition	+	0.8227	82.27%
CYP2C8 inhibition	-	0.9040	90.40%
CYP inhibitory promiscuity	+	0.7043	70.43%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6015	60.15%
Eye corrosion	-	0.9845	98.45%
Eye irritation	-	0.9112	91.12%
Skin irritation	-	0.7392	73.92%
Skin corrosion	-	0.8940	89.40%
Ames mutagenesis	-	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7165	71.65%
Micronuclear	-	0.5500	55.00%
Hepatotoxicity	+	0.6125	61.25%
skin sensitisation	-	0.8194	81.94%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.7809	78.09%
Acute Oral Toxicity (c)	III	0.7783	77.83%
Estrogen receptor binding	+	0.7186	71.86%
Androgen receptor binding	+	0.8536	85.36%
Thyroid receptor binding	+	0.6016	60.16%
Glucocorticoid receptor binding	-	0.6485	64.85%
Aromatase binding	+	0.7415	74.15%
PPAR gamma	-	0.8210	82.10%
Honey bee toxicity	-	0.9467	94.67%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6352	63.52%
Fish aquatic toxicity	+	0.9557	95.57%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2039	P27338	Monoamine oxidase B	497 nM	IC50	PMID: 22014827

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4481	P35228	Nitric oxide synthase, inducible	95.66%	94.80%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.44%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.12%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.79%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.16%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	93.12%	96.77%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	92.32%	90.24%
CHEMBL2581	P07339	Cathepsin D	92.09%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.23%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.62%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.95%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.85%	100.00%
CHEMBL4208	P20618	Proteasome component C5	83.09%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.82%	95.89%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.15%	90.71%
CHEMBL5028	O14672	ADAM10	80.84%	97.50%

Plants that contains it

• Piper nigrum

Cross-Links

• PubChem: 680623
• NPASS: NPC470707
• ChEMBL: CHEMBL2203919
• LOTUS: LTS0151733
• wikiData: Q104936858