Quinidine

Details

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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 17,606 references in papers

Physical and Chemical Properties

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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

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56-54-2
(+)-Quinidine
Conquinine
Pitayine
Chinidin
(8R,9S)-Quinidine
beta-Quinine
Kinidin
(9S)-6'-Methoxycinchonan-9-ol
Conchinin
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of Quinidine

3D Structure

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ADMET Properties (via admetSAR 2)

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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

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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

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Aspidosperma excelsum
Ciliosemina pedunculata
Cinchona calisaya
Cinchona officinalis
Cinchona pubescens

Cross-Links

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PubChem 441074
NPASS NPC264166
ChEMBL CHEMBL1294
LOTUS LTS0025986
wikiData Q412496