(5S)-5,8,9-trimethoxy-2,10-dimethyl-4,5-dihydropyrano[2,3-b]quinoline

Details

• Internal ID: 90bccc30-d3e9-4c6d-9059-ba070866d6e9
• Taxonomy: Organoheterocyclic compounds > Quinolines and derivatives > Quinolones and derivatives > Pyranoquinolines
• IUPAC Name: (5S)-5,8,9-trimethoxy-2,10-dimethyl-4,5-dihydropyrano[2,3-b]quinoline
• SMILES (Canonical): CC1=CCC2=C(O1)N(C3=C(C2OC)C=CC(=C3OC)OC)C
• SMILES (Isomeric): CC1=CCC2=C(O1)N(C3=C([C@@H]2OC)C=CC(=C3OC)OC)C
• InChI: InChI=1S/C17H21NO4/c1-10-6-7-12-15(20-4)11-8-9-13(19-3)16(21-5)14(11)18(2)17(12)22-10/h6,8-9,15H,7H2,1-5H3/t15-/m0/s1
• InChI Key: JJFMMXSBTATGFV-HNNXBMFYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₁NO₄
• Molecular Weight: 303.35 g/mol
• Exact Mass: 303.14705815 g/mol
• Topological Polar Surface Area (TPSA): 40.20 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 3.38
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9606	96.06%
Caco-2	+	0.9080	90.80%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.7000	70.00%
Subcellular localzation	Mitochondria	0.3485	34.85%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9528	95.28%
OATP1B3 inhibitior	+	0.9471	94.71%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.6241	62.41%
P-glycoprotein inhibitior	-	0.7456	74.56%
P-glycoprotein substrate	-	0.6956	69.56%
CYP3A4 substrate	+	0.5872	58.72%
CYP2C9 substrate	-	0.8074	80.74%
CYP2D6 substrate	+	0.4604	46.04%
CYP3A4 inhibition	+	0.5140	51.40%
CYP2C9 inhibition	-	0.7227	72.27%
CYP2C19 inhibition	-	0.5395	53.95%
CYP2D6 inhibition	-	0.8520	85.20%
CYP1A2 inhibition	+	0.5079	50.79%
CYP2C8 inhibition	+	0.5367	53.67%
CYP inhibitory promiscuity	+	0.6372	63.72%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.4677	46.77%
Eye corrosion	-	0.9837	98.37%
Eye irritation	-	0.8614	86.14%
Skin irritation	-	0.7791	77.91%
Skin corrosion	-	0.9370	93.70%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7892	78.92%
Micronuclear	+	0.6400	64.00%
Hepatotoxicity	+	0.5543	55.43%
skin sensitisation	-	0.8488	84.88%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.7155	71.55%
Acute Oral Toxicity (c)	III	0.6513	65.13%
Estrogen receptor binding	+	0.6773	67.73%
Androgen receptor binding	+	0.6299	62.99%
Thyroid receptor binding	+	0.8161	81.61%
Glucocorticoid receptor binding	+	0.7211	72.11%
Aromatase binding	-	0.5059	50.59%
PPAR gamma	+	0.7545	75.45%
Honey bee toxicity	-	0.8654	86.54%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.6500	65.00%
Fish aquatic toxicity	+	0.8534	85.34%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.50%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.39%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.03%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.62%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.09%	95.89%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	84.33%	89.62%
CHEMBL2581	P07339	Cathepsin D	82.53%	98.95%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	82.10%	100.00%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	81.96%	93.65%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	81.58%	100.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	81.24%	93.99%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.19%	93.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.21%	97.09%

Plants that contains it

• Vepris louisii

Cross-Links

• PubChem: 162993555
• LOTUS: LTS0263238
• wikiData: Q105129625