7-[(2R)-2-hydroxy-3-methylbut-3-enyl]-6-methoxy-9-methyl-[1,3]dioxolo[4,5-h]quinolin-8-one

Details

• Internal ID: ecabfe41-92ef-4b0b-9472-75cd7e2af5fb
• Taxonomy: Organoheterocyclic compounds > Quinolines and derivatives > Quinolones and derivatives > Hydroquinolones
• IUPAC Name: 7-[(2R)-2-hydroxy-3-methylbut-3-enyl]-6-methoxy-9-methyl-[1,3]dioxolo[4,5-h]quinolin-8-one
• InChI: InChI=1S/C17H19NO5/c1-9(2)12(19)7-11-15(21-4)10-5-6-13-16(23-8-22-13)14(10)18(3)17(11)20/h5-6,12,19H,1,7-8H2,2-4H3/t12-/m1/s1
• InChI Key: KWKLMCSZRFVKJI-GFCCVEGCSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₉NO₅
• Molecular Weight: 317.34 g/mol
• Exact Mass: 317.12632271 g/mol
• Topological Polar Surface Area (TPSA): 68.20 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 1.76
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9192	91.92%
Caco-2	+	0.8056	80.56%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.3219	32.19%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9112	91.12%
OATP1B3 inhibitior	+	0.9326	93.26%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.6036	60.36%
P-glycoprotein inhibitior	-	0.8443	84.43%
P-glycoprotein substrate	-	0.7495	74.95%
CYP3A4 substrate	+	0.5745	57.45%
CYP2C9 substrate	-	0.6099	60.99%
CYP2D6 substrate	-	0.8273	82.73%
CYP3A4 inhibition	+	0.6003	60.03%
CYP2C9 inhibition	-	0.7823	78.23%
CYP2C19 inhibition	-	0.6165	61.65%
CYP2D6 inhibition	-	0.8517	85.17%
CYP1A2 inhibition	-	0.5073	50.73%
CYP2C8 inhibition	-	0.8360	83.60%
CYP inhibitory promiscuity	-	0.5059	50.59%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.4969	49.69%
Eye corrosion	-	0.9865	98.65%
Eye irritation	-	0.7839	78.39%
Skin irritation	-	0.7940	79.40%
Skin corrosion	-	0.9358	93.58%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5376	53.76%
Micronuclear	+	0.6800	68.00%
Hepatotoxicity	+	0.5034	50.34%
skin sensitisation	-	0.8435	84.35%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.7074	70.74%
Acute Oral Toxicity (c)	III	0.6083	60.83%
Estrogen receptor binding	+	0.7452	74.52%
Androgen receptor binding	-	0.5280	52.80%
Thyroid receptor binding	+	0.6093	60.93%
Glucocorticoid receptor binding	+	0.7249	72.49%
Aromatase binding	-	0.6923	69.23%
PPAR gamma	+	0.6472	64.72%
Honey bee toxicity	-	0.8255	82.55%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.8707	87.07%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	98.91%	96.77%
CHEMBL2581	P07339	Cathepsin D	98.22%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.93%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.70%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.35%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.17%	95.56%
CHEMBL4040	P28482	MAP kinase ERK2	92.38%	83.82%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.35%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.63%	89.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.94%	91.11%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.99%	92.62%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.72%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.60%	86.33%

Plants that contains it

• Ptelea trifoliata

Cross-Links

• PubChem: 163036509
• LOTUS: LTS0217751
• wikiData: Q105146993