2-[4-(3,4-Methylenedioxyphenyl)butyl]-4(1H)-quinolinone

Details

• Internal ID: ddbc1bbd-e5d9-4048-9a9f-6238fca323b5
• Taxonomy: Organoheterocyclic compounds > Quinolines and derivatives > Quinolones and derivatives > Hydroquinolones
• IUPAC Name: 2-[4-(1,3-benzodioxol-5-yl)butyl]-1H-quinolin-4-one
• SMILES (Canonical): C1OC2=C(O1)C=C(C=C2)CCCCC3=CC(=O)C4=CC=CC=C4N3
• SMILES (Isomeric): C1OC2=C(O1)C=C(C=C2)CCCCC3=CC(=O)C4=CC=CC=C4N3
• InChI: InChI=1S/C20H19NO3/c22-18-12-15(21-17-8-4-3-7-16(17)18)6-2-1-5-14-9-10-19-20(11-14)24-13-23-19/h3-4,7-12H,1-2,5-6,13H2,(H,21,22)
• InChI Key: WVIITJBBQPBPEB-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₉NO₃
• Molecular Weight: 321.40 g/mol
• Exact Mass: 321.13649347 g/mol
• Topological Polar Surface Area (TPSA): 47.60 Ų
• XlogP: 4.50
• Atomic LogP (AlogP): 3.82
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

• 2-[4-(1,3-benzodioxol-5-yl)butyl]-1H-quinolin-4-one
• CHEMBL2272377
• CHEBI:169264
• DTXSID601222720
• 2-[4-(1,3-Benzodioxol-5-yl)butyl]-4(1H)-quinolinone
• 2-[4-(1,3-Benzodioxole-5-yl)butyl]-1,4-dihydroquinoline-4-one
• 2-[4-(2H-1,3-benzodioxol-5-yl)butyl]-1,4-dihydroquinolin-4-one
• 17889-77-9

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9969	99.69%
Caco-2	+	0.6667	66.67%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7343	73.43%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9009	90.09%
OATP1B3 inhibitior	+	0.9425	94.25%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.7521	75.21%
P-glycoprotein inhibitior	+	0.8036	80.36%
P-glycoprotein substrate	-	0.8177	81.77%
CYP3A4 substrate	+	0.5950	59.50%
CYP2C9 substrate	+	0.6095	60.95%
CYP2D6 substrate	-	0.8154	81.54%
CYP3A4 inhibition	+	0.8288	82.88%
CYP2C9 inhibition	-	0.5373	53.73%
CYP2C19 inhibition	+	0.6652	66.52%
CYP2D6 inhibition	+	0.6466	64.66%
CYP1A2 inhibition	+	0.9231	92.31%
CYP2C8 inhibition	-	0.7508	75.08%
CYP inhibitory promiscuity	+	0.8092	80.92%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6312	63.12%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.7118	71.18%
Skin irritation	-	0.7467	74.67%
Skin corrosion	-	0.9444	94.44%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8980	89.80%
Micronuclear	+	0.5759	57.59%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.8000	80.00%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.6435	64.35%
Acute Oral Toxicity (c)	III	0.6449	64.49%
Estrogen receptor binding	+	0.8850	88.50%
Androgen receptor binding	+	0.7854	78.54%
Thyroid receptor binding	+	0.6220	62.20%
Glucocorticoid receptor binding	+	0.7487	74.87%
Aromatase binding	+	0.7260	72.60%
PPAR gamma	+	0.7249	72.49%
Honey bee toxicity	-	0.8798	87.98%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	-	0.3625	36.25%

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	98.69%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.22%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.77%	94.45%
CHEMBL240	Q12809	HERG	97.32%	89.76%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	95.23%	96.77%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.04%	95.56%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	94.59%	94.80%
CHEMBL3192	Q9BY41	Histone deacetylase 8	93.72%	93.99%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	92.93%	91.71%
CHEMBL2535	P11166	Glucose transporter	89.02%	98.75%
CHEMBL255	P29275	Adenosine A2b receptor	88.87%	98.59%
CHEMBL5805	Q9NR97	Toll-like receptor 8	88.05%	96.25%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.73%	92.62%
CHEMBL3310	Q96DB2	Histone deacetylase 11	87.49%	88.56%
CHEMBL2717	Q9HCR9	Phosphodiesterase 11A	86.83%	85.00%
CHEMBL3401	O75469	Pregnane X receptor	86.43%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.42%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	85.75%	91.49%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	85.11%	96.37%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	84.88%	93.40%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.50%	94.00%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	82.78%	80.96%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.57%	86.33%
CHEMBL1781	P11387	DNA topoisomerase I	80.42%	97.00%

Plants that contains it

• Ruta graveolens

Cross-Links

• PubChem: 6325654
• NPASS: NPC283810
• LOTUS: LTS0066375
• wikiData: Q105313540