Cinchonan-9-ol, 6'-methoxy-, (8alpha,9R)-
| Internal ID | 7a9109b7-5230-437b-bed8-d613b71854b5 |
| Taxonomy | Alkaloids and derivatives > Cinchona alkaloids |
| IUPAC Name | (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(C3CC4CCN3CC4C=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 |
| InChI Key | LOUPRKONTZGTKE-UHFFFAOYSA-N |
| Popularity | 32 references in papers |
| 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 |
| 9-epi-Quinine |
| 936694-43-8 |
| (8alpha,9S)-6'-Methoxycinchonan-9-ol |
| (6-methoxy-4-quinolyl)(5-vinyl-1-azabicyclo[2.2.2]oct-2-yl)methanol |
| 572-60-1 |
| GNF-PF-5473 |
| Cinchonan-9-ol, 6'-methoxy-, (8alpha,9R)- |
| Cinchonan-9-ol, 6'-methoxy-, (8.alpha.,9R)- |
| MFCD00135581 |
| MFCD00198096 |
| There are more than 10 synonyms. If you wish to see them all click here. |
| 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% |
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% |
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.
To see more specific details click the taxa you are interested in.
| Ciliosemina pedunculata |
| Cinchona calisaya |
| Cinchona pubescens |
| PubChem | 1065 |
| LOTUS | LTS0122718 |
| wikiData | Q27166273 |