Quinine Hydrochloride
AlkaPlorer ID: AK007812
Synonym: None
IUPAC Name: (R)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol;hydrochloride
Structure
SMILES: COC1=CC2=C(C=CN=C2C=C1)[C@H]([C@@H]3C[C@@H]4CCN3C[C@@H]4C=C)O.Cl
InChI: InChI=1S/C20H24N2O2.ClH/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;1H/t13-,14-,19-,20+;/m0./s1
InChIKey: LBSFSRMTJJPTCW-DSXUQNDKSA-N
Source
| Species | Genus | Family | Order | Class | Phylum | Kingdom | Domain |
|---|
Properties Information
Molecule Weight: 360.88500000000005
TPSA？: 45.59
MolLogP？: 3.5950000000000033
Number of H-Donors: 1
Number of H-Acceptors: 4
RingCount: 5
Activities Information
| Organism | Target Name | Standard Type | Standard Value | Standard Units | doi |
|---|---|---|---|---|---|
| Electrophorus electricus | Acetylcholinesterase | Inhibition | 15.78 | % | 10.1016/j.bmc.2012.09.040 |
| Equus caballus | Cholinesterase | Inhibition | 24.7 | % | 10.1016/j.bmc.2012.09.040 |
| Homo sapiens | Glucose transporter | Inhibition | 0.77 | % | 10.6019/CHEMBL3433997 |
| Homo sapiens | Glucose transporter | Inhibition | 7.23 | % | 10.6019/CHEMBL3433997 |
| Homo sapiens | HepG2 | Inhibition | 0.0 | % | 10.1038/nature09107 |
| Homo sapiens | HepG2 | Inhibition | 13.0 | % | 10.1038/nature09107 |
| Leishmania mexicana | Glucose transporter | Inhibition | -0.01 | % | 10.6019/CHEMBL3433997 |
| Leishmania mexicana | Glucose transporter | Inhibition | 5.72 | % | 10.6019/CHEMBL3433997 |
| Plasmodium falciparum | Hexose transporter 1 | Inhibition | 2.26 | % | 10.6019/CHEMBL3433997 |
| Plasmodium falciparum | Hexose transporter 1 | Inhibition | 6.11 | % | 10.6019/CHEMBL3433997 |
| Plasmodium falciparum | Plasmodium falciparum | Activity | 40.0 | mg kg-1 | 10.1021/jm00196a019 |
| Plasmodium falciparum | Plasmodium falciparum | Activity | 80.0 | mg kg-1 | 10.1021/jm00196a019 |
| Plasmodium falciparum | Plasmodium falciparum | CD90 | 20.0 | mg kg-1 | 10.1021/jm00196a019 |
| Plasmodium falciparum | Plasmodium falciparum | CD90 | 80.0 | mg kg-1 | 10.1021/jm00196a019 |
| Plasmodium falciparum | Plasmodium falciparum | IC50 | 5.9 | nM | 10.1128/aac.01313-06 |
| Plasmodium falciparum | Plasmodium falciparum | IC50 | 6.6 | nM | 10.1128/aac.01313-06 |
| Plasmodium falciparum | Plasmodium falciparum | IC50 | 6.7 | nM | 10.1128/aac.01313-06 |
| Plasmodium falciparum | Plasmodium falciparum | IC50 | 6.9 | nM | 10.1128/aac.01313-06 |
| Plasmodium falciparum | Plasmodium falciparum | IC50 | 15.1 | nM | 10.1128/aac.01313-06 |
| Plasmodium falciparum | Plasmodium falciparum | IC50 | 22.2 | nM | 10.1128/aac.01313-06 |
| Plasmodium falciparum | Plasmodium falciparum | IC50 | 652.0 | nM | 10.1128/aac.00282-08 |
| Plasmodium falciparum | Plasmodium falciparum | IC90 | 12.4 | nM | 10.1128/aac.01313-06 |
| Plasmodium falciparum | Plasmodium falciparum | IC90 | 13.2 | nM | 10.1128/aac.01313-06 |
| Plasmodium falciparum | Plasmodium falciparum | IC90 | 42.6 | nM | 10.1128/aac.01313-06 |
| Plasmodium falciparum | Plasmodium falciparum | IC90 | 63.7 | nM | 10.1128/aac.01313-06 |
| Plasmodium falciparum | Plasmodium falciparum | IC90 | 116.0 | nM | 10.1128/aac.01313-06 |
| Plasmodium falciparum | Plasmodium falciparum | IC90 | 128.0 | nM | 10.1128/aac.01313-06 |
| Plasmodium falciparum | Plasmodium falciparum | Inhibition | 0.0 | % | 10.1038/nature09107 |
| Plasmodium falciparum | Plasmodium falciparum | Inhibition | 79.0 | % | 10.1038/nature09107 |
| Plasmodium falciparum | Plasmodium falciparum | Inhibition | 99.0 | % | 10.1038/nature09107 |
| Plasmodium falciparum | Plasmodium falciparum | Inhibition | 100.0 | % | 10.1038/nature09107 |
| Plasmodium falciparum | Plasmodium falciparum | XC50 | 95.16 | nM | 10.1038/nature09107 |
| Plasmodium falciparum | Plasmodium falciparum | XC50 | 145.09 | nM | 10.1038/nature09107 |
| Plasmodium vivax | Plasmodium vivax | CD90 | 40.0 | mg kg-1 | 10.1021/jm00196a019 |
| None | No relevant target | solubility | 2.1 | 10'-1mg/ml | 10.1016/j.bmcl.2016.02.060 |
| None | Unchecked | IFI | 0.71 | % | 10.1038/nature09107 |
| None | Unchecked | IFI | 0.73 | % | 10.1038/nature09107 |