[(2R,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methanol

Details

• Internal ID: 2bd51662-bf02-4222-9f21-5e1fa933db73
• Taxonomy: Alkaloids and derivatives > Cinchona alkaloids
• IUPAC Name: [(2R,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol
• SMILES (Canonical): COC1=CC2=C(C=CN=C2C=C1)C(C3CC4CCN3CC4C=C)O
• SMILES (Isomeric): COC1=CC2=C(C=CN=C2C=C1)C([C@H]3CC4CCN3C[C@@H]4C=C)O
• InChI: InChI=1S/C20H24N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3/t13-,14?,19+,20?/m0/s1
• InChI Key: LOUPRKONTZGTKE-BEFZOFJQSA-N
• Popularity: 7 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: 2.90

Synonyms

• SCHEMBL13587302
• CHEBI:95172
• HMS1791J09
• NCGC00015871-04
• NCGC00015871-05
• NCGC00015871-06
• NCGC00015871-08
• NCGC00015871-09
• NCGC00163147-04
• NCGC00163147-05
• NCGC00163147-06
• Q27166974
• [(2R,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methanol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL289	P10635	Cytochrome P450 2D6	9 nM	IC50	via Super-PRED
CHEMBL240	Q12809	HERG	323.59 nM	IC50	via Super-PRED
CHEMBL1947	P10828	Thyroid hormone receptor beta-1	63.1 nM	Potency	via Super-PRED
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	100 nM	Potency	via Super-PRED
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	31.6 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.23%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.23%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.88%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.53%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	93.26%	95.89%
CHEMBL1951	P21397	Monoamine oxidase A	92.18%	91.49%
CHEMBL2243	O00519	Anandamide amidohydrolase	91.85%	97.53%
CHEMBL241	Q14432	Phosphodiesterase 3A	89.27%	92.94%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	89.05%	91.03%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.73%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	88.50%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.82%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.63%	94.00%
CHEMBL5747	Q92793	CREB-binding protein	86.76%	95.12%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	86.43%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.49%	89.00%
CHEMBL1868	P17948	Vascular endothelial growth factor receptor 1	84.99%	96.47%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.61%	96.00%
CHEMBL5203	P33316	dUTP pyrophosphatase	83.72%	99.18%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.63%	97.09%
CHEMBL2581	P07339	Cathepsin D	83.18%	98.95%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	83.04%	98.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.82%	92.62%
CHEMBL6175	Q9H3R0	Lysine-specific demethylase 4C	82.39%	96.69%
CHEMBL264	Q9Y5N1	Histamine H3 receptor	81.71%	91.43%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.42%	95.83%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	81.28%	89.62%
CHEMBL4208	P20618	Proteasome component C5	81.25%	90.00%

Plants that contains it

• Aspidosperma excelsum
• Ciliosemina pedunculata
• Cinchona calisaya
• Cinchona officinalis
• Cinchona pubescens

Cross-Links

• PubChem: 24867865
• LOTUS: LTS0234139
• wikiData: Q27166974