Quinidine

Details

• Internal ID: a2f47905-b372-4379-a332-39c4ceb05886
• Taxonomy: Alkaloids and derivatives > Cinchona alkaloids
• IUPAC Name: (S)-[(2R,4S,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@@H]([C@H]3C[C@@H]4CCN3C[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-LHHVKLHASA-N
• Popularity: 17,771 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
• Atomic LogP (AlogP): 3.17
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• 56-54-2
• (+)-Quinidine
• Conquinine
• Pitayine
• Chinidin
• (8R,9S)-Quinidine
• beta-Quinine
• Kinidin
• (9S)-6'-Methoxycinchonan-9-ol
• Conchinin
• Conchinine
• Quinidex
• Cin-Quin
• beta-Quinidine
• chinidinum
• quinidina
• Cinchonan-9-ol, 6'-methoxy-, (9S)-
• Quincardine
• Chinidine
• CHEBI:28593
• alpha-(6-Methoxy-4-quinolyl)-5-vinyl-2-quinuclidinemethanol
• (S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol
• .beta.-Quinidine
• UNII-ITX08688JL
• CCRIS 672
• Quiniduran
• HSDB 225
• ITX08688JL
• DTXSID4023549
• Quinidine sulfate
• Quinidine [BAN:NF]
• EINECS 200-279-0
• Quinicardine
• Quinora
• 6-Methoxy-alpha-(5-vinyl-2-quinuclidinyl)-4-quinolinemethanol
• CHEMBL1294
• Quindine
• (1S)-(6-Methoxyquinolin-4-yl)((2R,4S,5R)-5-vinylquinuclidin-2-yl)methanol
• DTXCID70819883
• Chinidin [German]
• Auriquin
• Quinidine HCl
• NCI-C56246
• alpha-(6-Methoxy-4-quinolyl)-5-vinyl-2-quinuclidinemethanol (9S)-
• (9S)-6-Methoxy-alpha-(5-vinyl-2-quinuclidinyl)-4-quinolinemethanol
• (S)-(6-methoxyquinolin-4-yl)((2R,5R)-5-vinylquinuclidin-2-yl)methanol
• (3'.alpha., 9S)-6'-Methoxycinchonan-9-ol
• QUINIDINE (MART.)
• QUINIDINE [MART.]
• (R)-(6-methoxyquinolin-4-yl)((3S,4R,7S)-3-vinylquinuclidin-7-yl)methanol
• (S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol
• quinidin-
• TCMDC-131239
• C20H24N2O2
• MFCD00135581
• (S)-(6-methoxy-4-quinolyl)-[(2R,4S,5R)-5-vinylquinuclidin-2-yl]methanol
• (S)-(6-Methoxy-quinolin-4-yl)-((2R,5R)-5-vinyl-1-aza-bicyclo[2.2.2]oct-2-yl)-methanol
• (S)-(6-methoxyquinolin-4-yl)((1S,2R,4S,5R)-5-vinylquinuclidin-2-yl)methanol
• (S)-[(4S,5R,7R)-5-ethenyl-1-azabicyclo[2.2.2]octan-7-yl]-(6-methoxyquinolin-4-yl)methanol
• CAS-56-54-2
• (S)-((2S,4S,5R)-5-ETHENYL-1-AZABICYCLO(2.2.2)OCT-2-YL)(6-METHOXYQUINOLIN-4-YL)METHANOL
• SMR000857275
• Quinindine
• (8R,9S)-6'-Methoxycinchonan-9-ol
• (S)-(6-Methoxy-quinolin-4-yl)-((2R,5R)-5-vinyl-1-aza-bicyclo(2.2.2)oct-2-yl)-methanol
• NCGC00159499-02
• QDN
• Quinidine, anhydrous
• QUINIDINE [MI]
• QUINIDINE [HSDB]
• Prestwick3_000280
• QUINIDINE [VANDF]
• bmse000511
• Epitope ID:141803
• QUINIDINE [WHO-DD]
• SCHEMBL15943
• BSPBio_000160
• MLS001335913
• MLS001335914
• MLS002548869
• BPBio1_000176
• GTPL2342
• SCHEMBL17537608
• HMS2234L10
• HMS3259O09
• NCI-C56426
• HY-B1751
• Tox21_111720
• Tox21_201110
• 6-methoxy--(5-vinyl-2-quinuclidinyl)-4-quinolinemethanol
• BDBM50121975
• AKOS015920101
• Tox21_111720_1
• CCG-256507
• CS-7812
• DB00908
• NC00478
• SDCCGMLS-0066600.P001
• NCGC00091231-01
• NCGC00091231-02
• NCGC00091231-03
• NCGC00091231-04
• NCGC00091231-18
• NCGC00258662-01
• AS-30538
• QUININE SULFATE IMPURITY A [WHO-IP]
• AB00514657
• QUININE BISULFATE IMPURITY A [WHO-IP]
• EN300-305202
• AB01562940_01
• QUININE SULFATE IMPURITY A [EP IMPURITY]
• CINCHONAN-9-0L, 6'-METHOXY-, (95)-
• Q412496
• W-109256
• BRD-K59632282-052-01-5
• BRD-K59632282-052-02-3
• BRD-K70799801-311-02-7
• QUININE HYDROCHLORIDE IMPURITY A [EP IMPURITY]
• Quinidine, crystallized, >=98.0% (dried material, NT)
• Z1741976976
• QUININE BISULFATE HEPTAHYDRATE IMPURITY A [WHO-IP]
• 6'-METHOXY-ALPHA-(5-VINYL-2-QUINUCLIDINYL)-4-QUINOLINEMETHONOL

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9821	98.21%
Caco-2	+	0.9313	93.13%
Blood Brain Barrier	-	0.5230	52.30%
Human oral bioavailability	+	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7501	75.01%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9541	95.41%
OATP1B3 inhibitior	+	0.9529	95.29%
MATE1 inhibitior	-	0.7805	78.05%
OCT2 inhibitior	+	0.9750	97.50%
BSEP inhibitior	+	0.8817	88.17%
P-glycoprotein inhibitior	+	0.8509	85.09%
P-glycoprotein substrate	+	0.8755	87.55%
CYP3A4 substrate	+	0.6949	69.49%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.5188	51.88%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	+	0.8931	89.31%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.9882	98.82%
CYP inhibitory promiscuity	-	0.7225	72.25%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6553	65.53%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9837	98.37%
Skin irritation	+	0.6670	66.70%
Skin corrosion	-	0.9034	90.34%
Ames mutagenesis	-	1.0000	100.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8917	89.17%
Micronuclear	+	0.6200	62.00%
Hepatotoxicity	+	0.9875	98.75%
skin sensitisation	-	0.8660	86.60%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	-	0.8240	82.40%
Acute Oral Toxicity (c)	II	0.7460	74.60%
Estrogen receptor binding	-	0.5092	50.92%
Androgen receptor binding	+	0.8037	80.37%
Thyroid receptor binding	-	0.5568	55.68%
Glucocorticoid receptor binding	+	0.5838	58.38%
Aromatase binding	-	0.4938	49.38%
PPAR gamma	-	0.8546	85.46%
Honey bee toxicity	-	0.7392	73.92%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	-	0.5605	56.05%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	12589.3 nM	Potency	via CMAUP
CHEMBL1914	P06276	Butyrylcholinesterase	1230 nM	IC50	PMID: 23062825
CHEMBL3397	P11712	Cytochrome P450 2C9	32000 nM	Ki	PMID: 14761192
CHEMBL289	P10635	Cytochrome P450 2D6	14 nM; 11 nM; 19.6 nM; 10 nM; 10 nM; 18 nM; 14 nM; < 6 nM; 2 nM; 17 nM; 14 nM; 30 nM; 9 nM; 17 nM; 20 nM; 10 nM; 3.3 nM; 9 nM	IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50	PMID: 18763754; PMID: 18324762; PMID: 19117415; PMID: 21138310; PMID: 21189020; PMID: 26204510; PMID: 21384875; PMID: 25082126; PMID: 24050112; PMID: 24793360; PMID: 18672861; PMID: 26355532; PMID: 26962886; PMID: 27105029; PMID: 16570918; PMID: 15481972; PMID: 12502361; via Super-PRED
CHEMBL340	P08684	Cytochrome P450 3A4	15848.9 nM; 15848.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL240	Q12809	HERG	323.59 nM; 323.59 nM; 323.59 nM; 323.59 nM	IC50; IC50; IC50; IC50	PMID: 18448342; PMID: 15911273; PMID: 12873512; via Super-PRED
CHEMBL1743126	Q96FL8	Multidrug and toxin extrusion protein 1	11200 nM	IC50	PMID: 23241029
CHEMBL4302	P08183	P-glycoprotein 1	2200 nM; 1000 nM; 2200 nM; 5600 nM; 5600 nM; 18800 nM	IC50; IC50; IC50; IC50; IC50; IC50	PMID: 10820137; PMID: 11716514; PMID: 12699389; PMID: 12699389; PMID: 12699389; PMID: 11716514
CHEMBL1980	Q14524	Sodium channel protein type V alpha subunit	16600 nM; 6900 nM	IC50; IC50	PMID: 21300721; PMID: 17506538
CHEMBL5685	O15245	Solute carrier family 22 member 1	113800 nM; 23400 nM	IC50; IC50	PMID: 18788725; PMID: 10027858
CHEMBL1947	P10828	Thyroid hormone receptor beta-1	63.1 nM	Potency	via Super-PRED
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	25118.9 nM; 25118.9 nM; 100 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via Super-PRED
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	31.6 nM; 31.6 nM	Potency; Potency	via Super-PRED; via CMAUP
CHEMBL1940	Q13936	Voltage-gated L-type calcium channel alpha-1C subunit	19820 nM	IC50	PMID: 22761000
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	7300 nM	IC50	PMID: 17506538

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: 441074
• NPASS: NPC264166
• ChEMBL: CHEMBL1294
• LOTUS: LTS0025986
• wikiData: Q412496