Cinchonan-9-ol, 6'-methoxy-, (8alpha,9R)-

Details

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Internal ID 9ea2244f-28f5-4610-bc21-c2ba8e5ee084
Taxonomy Alkaloids and derivatives > Cinchona alkaloids
IUPAC Name (R)-[(2S,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]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-VOMFEXJBSA-N
Popularity 6,786 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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Quinine [BAN]
Quinine (BAN)
Conchinin
Quindan
Quinidex
Quinimax
Quinine tannate
quinidin-
C20H24N2O2
Chinidin [German]
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of Cinchonan-9-ol, 6'-methoxy-, (8alpha,9R)-

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
CHEMBL289 P10635 Cytochrome P450 2D6 610 nM
9 nM
IC50
IC50
PMID: 19097894
via Super-PRED
CHEMBL240 Q12809 HERG 323.59 nM
IC50
via Super-PRED
CHEMBL1947 P10828 Thyroid hormone receptor beta-1 63.1 nM
63.1 nM
Potency
Potency
via Super-PRED
PMID: 25945867
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

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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.
Cinchona calisaya

Cross-Links

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PubChem 8549
NPASS NPC329708
ChEMBL CHEMBL387326
LOTUS LTS0102308
wikiData Q105154942