6-Methoxycinchonan-9-ol

Details

• Internal ID: 9f10598c-c776-4553-8ec2-5f46f3337602
• Taxonomy: Alkaloids and derivatives > Cinchona alkaloids
• IUPAC Name: (5-ethenyl-7-methoxy-1-azabicyclo[2.2.2]octan-2-yl)-quinolin-4-ylmethanol
• SMILES (Canonical): COC1CC2CC(N1CC2C=C)C(C3=CC=NC4=CC=CC=C34)O
• SMILES (Isomeric): COC1CC2CC(N1CC2C=C)C(C3=CC=NC4=CC=CC=C34)O
• InChI: InChI=1S/C20H24N2O2/c1-3-13-12-22-18(10-14(13)11-19(22)24-2)20(23)16-8-9-21-17-7-5-4-6-15(16)17/h3-9,13-14,18-20,23H,1,10-12H2,2H3
• InChI Key: NAXGSHXNYVZTNO-UHFFFAOYSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄N₂O₂
• Molecular Weight: 324.40 g/mol
• Exact Mass: 324.183778013 g/mol
• Topological Polar Surface Area (TPSA): 45.60 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 3.14
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• SCHEMBL454394
• DTXSID80972650

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9815	98.15%
Caco-2	+	0.8790	87.90%
Blood Brain Barrier	+	0.7434	74.34%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.5552	55.52%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9222	92.22%
OATP1B3 inhibitior	+	0.9458	94.58%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	+	0.5936	59.36%
BSEP inhibitior	-	0.8139	81.39%
P-glycoprotein inhibitior	+	0.5803	58.03%
P-glycoprotein substrate	+	0.6800	68.00%
CYP3A4 substrate	+	0.6862	68.62%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7378	73.78%
CYP3A4 inhibition	-	0.5828	58.28%
CYP2C9 inhibition	-	0.8467	84.67%
CYP2C19 inhibition	-	0.6856	68.56%
CYP2D6 inhibition	-	0.6778	67.78%
CYP1A2 inhibition	-	0.8461	84.61%
CYP2C8 inhibition	-	0.7112	71.12%
CYP inhibitory promiscuity	-	0.6793	67.93%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9513	95.13%
Carcinogenicity (trinary)	Non-required	0.6526	65.26%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.9763	97.63%
Skin irritation	-	0.6907	69.07%
Skin corrosion	-	0.9289	92.89%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9045	90.45%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	+	0.6928	69.28%
skin sensitisation	-	0.8737	87.37%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.7090	70.90%
Acute Oral Toxicity (c)	III	0.5349	53.49%
Estrogen receptor binding	+	0.5827	58.27%
Androgen receptor binding	+	0.7190	71.90%
Thyroid receptor binding	+	0.5671	56.71%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	-	0.5779	57.79%
PPAR gamma	-	0.7190	71.90%
Honey bee toxicity	-	0.5882	58.82%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	-	0.4401	44.01%

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	98.63%	96.09%
CHEMBL240	Q12809	HERG	97.30%	89.76%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.29%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.53%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	95.30%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.89%	89.00%
CHEMBL2581	P07339	Cathepsin D	92.06%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.05%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.08%	95.56%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	85.04%	94.08%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	83.16%	100.00%
CHEMBL1868	P17948	Vascular endothelial growth factor receptor 1	83.15%	96.47%
CHEMBL3401	O75469	Pregnane X receptor	81.96%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.72%	94.45%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	81.30%	98.33%
CHEMBL3902	P09211	Glutathione S-transferase Pi	81.09%	93.81%

Plants that contains it

• Cinchona calisaya

Cross-Links

• PubChem: 102439
• NPASS: NPC181631