Responsive image

Common name


Quinine

IUPAC name


(R)-[(1S,2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol

SMILES


[H][C@]1(C[C@@H]2CC[N@]1C[C@@H]2C=C)[C@H](O)C1=CC=NC2=CC=C(OC)C=C12

Compound class


Antimalarials; Antiprotozoal Agents; Analgesics, Non-Narcotic; Muscle Relaxants, Central; Musculo-Skeletal System; Antiparasitic Products, Insecticides and Repellents; Methanolquinolines; Quinine and Derivatives; Cytochrome P-450 CYP1A2 Inhibitors; Cytochrome P-450 CYP2C9 Inhibitors; Cytochrome P-450 CYP1A2 Inducers; Cytochrome P-450 CYP2C8 Inhibitors; Cytochrome P-450 CYP2C9 Inducers; Cytochrome P-450 CYP2C19 Inducers; Cytochrome P-450 CYP2C8 Inducers; CYP2D6 Inducers; CYP2D6 Inducers (strong); CYP2E1 Inhibitors; CYP2E1 Inducers; CYP2E1 Inducers (strong); CYP3A4 Inhibitors; Combined Inhibitors of CYP3A4 and P-glycoprotein;

Therapeutic area


For the treatment of malaria and leg cramps.

Common name


Quinine

IUPAC name


(R)-[(1S,2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol

SMILES


[H][C@]1(C[C@@H]2CC[N@]1C[C@@H]2C=C)[C@H](O)C1=CC=NC2=CC=C(OC)C=C12

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

FORMULA


C20H24N2O2

Responsive image

Common name


Quinine

IUPAC name


(R)-[(1S,2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol

Molecular weight


324.417

clogP


3.113

clogS


-3.551

HBond Acceptor


4

HBond Donor


1

Total Polar
Surface Area


45.59

Number of Rings


4

Rotatable Bond


4

Drug ID Common name Structure CAS SMILE Frequency
FDBF00787 4-quinolylmethanol Responsive image C(O)c1c2c(ncc1)cccc2 0.0014
FDBF00789 quinoline Responsive image n1c2c(ccc1)cccc2 0.0041
FDBF00830 quinuclidine Responsive image N12CCC(CC1)CC2 0.0024
FDBF01009 6-methoxyquinoline Responsive image O(C)c1cc2c(nccc2)cc1 0.0014
FDBF01010 [(2S)-quinuclidin-2-yl]methanol Responsive image N12C(CC(CC1)CC2)CO 0.0007
FDBF01011 (3R)-3-vinylquinuclidine Responsive image C(=C)C1C2CCN(C1)CC2 0.0010
FDBF01012 (6-methoxy-4-quinolyl)methanol Responsive image O(C)c1cc2c(nccc2CO)cc1 0.0010
FDBF01013 [(2S,4S,5R)-5-vinylquinuclidin-2-yl]methanol Responsive image C(=C)C1C2CC(N(C1)CC2)CO 0.0003
FDBF01014 (R)-4-quinolyl-[(2S)-quinuclidin-2-yl]methanol Responsive image N12C(CC(CC1)CC2)C(c3c4c(ncc3)cccc4)O 0.0007
9 , 1