Cinchonine

Details

• Internal ID: 8b64006e-dd4f-4613-bb84-2c1034503023
• Taxonomy: Alkaloids and derivatives > Cinchona alkaloids
• IUPAC Name: (S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol
• InChI: InChI=1S/C19H22N2O/c1-2-13-12-21-10-8-14(13)11-18(21)19(22)16-7-9-20-17-6-4-3-5-15(16)17/h2-7,9,13-14,18-19,22H,1,8,10-12H2/t13-,14-,18+,19-/m0/s1
• InChI Key: KMPWYEUPVWOPIM-QAMTZSDWSA-N
• Popularity: 1,460 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₂N₂O
• Molecular Weight: 294.40 g/mol
• Exact Mass: 294.173213330 g/mol
• Topological Polar Surface Area (TPSA): 36.40 Ų
• XlogP: 2.70

Synonyms

• 118-10-5
• D-Cinchonine
• Cinchonan-9-ol, (9S)-
• (9S)-Cinchonan-9-ol
• (8R,9S)-Cinchonine
• (+)-Cinconine
• DTXSID6045082
• NSC-6176
• V43X79NZCD
• CHEBI:27509
• DTXCID801474963
• 2-Quinuclidinemethanol, alpha-(5-vinyl-2-quinolyl)-
• alpha-(5-Vinyl-2-quinuclidinyl)-4-quinolinemethanol
• (S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol
• (S)-((2R,4S,5R)-5-ethenyl-1-azabicyclo(2.2.2)octan-2-yl)-quinolin-4-ylmethanol
• LA-40221
• RefChem:126196
• 204-234-6
• (+)-Cinchonine
• MFCD00064372
• (1S)-Quinolin-4-yl((2R,4S,5R)-5-vinylquinuclidin-2-yl)methanol
• (+)-cinchonin
• (S)-Quinolin-4-yl((1S,2R,4S,5S)-5-vinylquinuclidin-2-yl)methanol
• cinchonin
• 2-Quinuclidinemethanol, .alpha.-(5-vinyl-2-quinolyl)-
• NSC6176
• .alpha.-Quinidine
• (S)-4-quinolyl-[(2R,4S,5R)-5-vinylquinuclidin-2-yl]methanol
• (S)-quinolin-4-yl((1S,2R,4S,5R)-5-vinylquinuclidin-2-yl)methanol
• (S)-Quinolin-4-yl-(5-vinyl-1-aza-bicyclo[2.2.2]oct-2-yl)-methanol
• UNII-V43X79NZCD
• (9S)-Cinchonan-9-ol; Cinchonine (8CI); (+)-Cinchonine; (8R,9S)-Cinchonine; NSC 6176; d-Cinchonine
• CAS-118-10-5
• NSC 6176
• EINECS 204-234-6
• CINCHORINE
• Cinchonine (Standard)
• CINCHONINE [MI]
• AI3-09058
• Prestwick3_000608
• 2-Quinuclidinemethanol, .alpha.-4-quinolyl-5-vinyl-
• (+)-Cinchonine, 85%
• CINCHONINE [WHO-DD]
• (+)-Cinchonine; >99%
• BSPBio_000516
• MLS002153907
• SCHEMBL158394
• SCHEMBL158395
• BPBio1_000568
• CHEMBL588619
• MEGxp0_001905
• orb1311022
• SCHEMBL29364855
• ACon0_001352
• ACon1_000336
• GTPL13363
• HY-Y0152R
• HMS2096J18
• HMS2235N18
• HY-Y0152
• Tox21_110009
• (+)-Cinchonine, analytical standard
• BDBM50370411
• MSK159057
• AKOS015895982
• FC11047
• NCGC00013067-01
• NCGC00169174-01
• NCGC00169174-02
• NCGC00262542-03
• NCGC00262542-10
• DS-15267
• NCI60_005298
• SMR001233256
• Cinchonine, crystallized, >=98.0% (NT)
• AB00374715
• CS-0008420
• O10016
• WLN: T66 BNJ EYQ-DT66 A B CNTJ A1U1
• AL-466/21162039
• AM-331/20711019
• F121600
• Q2972710
• BRD-K90268819-001-03-4
• 4-Quinolyl(5-vinyl-1-azabicyclo[2.2.2]oct-2-yl)methanol;(5-Ethenyl-1-azabicyclo[2.2.2]oct-2-yl)(quinolin-4-yl)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	1800 nM	IC50	PMID: 20713660

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL240	Q12809	HERG	96.43%	89.76%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.07%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.31%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.66%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.31%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.94%	95.56%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	87.88%	98.33%
CHEMBL4302	P08183	P-glycoprotein 1	87.72%	92.98%
CHEMBL3902	P09211	Glutathione S-transferase Pi	87.58%	93.81%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	87.22%	95.83%
CHEMBL264	Q9Y5N1	Histamine H3 receptor	86.08%	91.43%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	85.94%	94.23%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	85.17%	94.08%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.70%	95.89%
CHEMBL1868	P17948	Vascular endothelial growth factor receptor 1	84.48%	96.47%
CHEMBL1951	P21397	Monoamine oxidase A	83.67%	91.49%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.27%	99.23%
CHEMBL2581	P07339	Cathepsin D	81.86%	98.95%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	81.64%	89.62%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	81.08%	100.00%
CHEMBL2492	P36544	Neuronal acetylcholine receptor protein alpha-7 subunit	80.72%	88.42%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	80.45%	94.62%

Plants that contains it

• Ciliosemina pedunculata
• Ciliosemina purdieana
• Cinchona calisaya
• Cinchona officinalis
• Cinchona pubescens
• Neolamarckia cadamba

Cross-Links

• PubChem: 90454
• NPASS: NPC150048
• ChEMBL: CHEMBL588619
• LOTUS: LTS0125043
• wikiData: Q2972710