IMPPAT Phytochemical information: 
Quinine
Quinine
Summary

SMILES: C=C[C@H]1CN2CC[C@H]1C[C@H]2[C@@H](c1ccnc2c1cc(OC)cc2)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
InChIKey: LOUPRKONTZGTKE-WZBLMQSHSA-N
DeepSMILES: C=C[C@H]CNCC[C@H]6C[C@H]6[C@@H]cccncc6ccOC))cc6))))))))))O
Scaffold Graph/Node/Bond level: c1ccc2c(CC3CC4CCN3CC4)ccnc2c1
Scaffold Graph/Node level: C1CCC2C(CC3CC4CCN3CC4)CCNC2C1
Scaffold Graph level: C1CCC2C(C1)CCCC2CC1CC2CCC1CC2
Functional groups: C=CC; CN(C)C; cnc; cOC; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Cinchona alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
Synonymous chemical names:
quinine, Quinine
External chemical identifiers:
CID:CID_3034034; ChEMBL:CHEMBL170; ChEBI:CHEBI:15854; ZINC:ZINC000003831404; FDASRS:A7V27PHC7A; SureChEMBL:SCHEMBL27031; MolPort-000-146-082
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Quinine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 324.42
Log P RDKit 3.17
Topological polar surface area (Å2) RDKit 45.59
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 24
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.2
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 11
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.45
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 3
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
Quinine
Drug-likeness
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.877602
Quinine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.23
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No
Quinine
Phytochemical - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_001816ENSG00000108846ABCC38714BindingDB, NPASS
TAR_EXP_000727ENSG00000178394HTR1A3350ChEMBL
TAR_EXP_000616ENSG00000111700SLCO1B328234ChEMBL, NPASS
TAR_EXP_000533ENSG00000113327GABRG22566ChEMBL
TAR_EXP_001056ENSG00000065989PDE4A5141ChEMBL
TAR_EXP_000528ENSG00000145864GABRB22561ChEMBL
TAR_EXP_000522ENSG00000151834GABRA22555ChEMBL
TAR_EXP_000521ENSG00000022355GABRA12554ChEMBL
TAR_EXP_000405ENSG00000180210F22147ChEMBL
TAR_EXP_000805ENSG00000171303KCNK33777ChEMBL, NPASS
TAR_EXP_000401ENSG00000163631ALB213BindingDB, ChEMBL, NPASS
TAR_EXP_000395ENSG00000091831ESR12099ChEMBL
TAR_EXP_000326ENSG00000151577DRD31814ChEMBL
TAR_EXP_001808ENSG00000276582ABCB118647ChEMBL, NPASS
TAR_EXP_001591ENSG00000006638TBXA2R6915ChEMBL
TAR_EXP_001542ENSG00000197375SLC22A56584ChEMBL, NPASS
TAR_EXP_001541ENSG00000197208SLC22A46583ChEMBL, NPASS
TAR_EXP_001106ENSG00000085563ABCB15243ChEMBL, NPASS
TAR_EXP_001206ENSG00000042088TDP155775NPASS
TAR_EXP_001298ENSG00000095303PTGS15742ChEMBL
TAR_EXP_001470ENSG00000144285SCN1A6323ChEMBL
TAR_EXP_001471ENSG00000136531SCN2A6326ChEMBL
TAR_EXP_001472ENSG00000153253SCN3A6328ChEMBL, NPASS
TAR_EXP_001518ENSG00000103546SLC6A26530ChEMBL
TAR_EXP_000733ENSG00000135914HTR2B3357ChEMBL
TAR_EXP_001053ENSG00000172572PDE3A5139ChEMBL
TAR_EXP_001105ENSG00000082175PGR5241ChEMBL
TAR_EXP_001047ENSG00000169427KCNK951305ChEMBL, NPASS
TAR_EXP_000881ENSG00000087085ACHE43ChEMBL
TAR_EXP_000851ENSG00000189221MAOA4128ChEMBL
TAR_EXP_000773ENSG00000169083AR367ChEMBL
TAR_EXP_000810ENSG00000128052KDR3791ChEMBL
TAR_EXP_001519ENSG00000142319SLC6A36531ChEMBL
TAR_EXP_001520ENSG00000108576SLC6A46532ChEMBL
TAR_EXP_001538ENSG00000175003SLC22A16580BindingDB, ChEMBL, NPASS
TAR_EXP_001539ENSG00000146477SLC22A36581ChEMBL
TAR_EXP_001540ENSG00000112499SLC22A26582BindingDB, ChEMBL, NPASS
TAR_EXP_001003ENSG00000112038OPRM14988ChEMBL
TAR_EXP_000798ENSG00000055118KCNH23757ChEMBL
TAR_EXP_000125ENSG00000101180HRH311255ChEMBL
TAR_EXP_000324ENSG00000184845DRD11812ChEMBL
TAR_EXP_000061ENSG00000134538SLCO1B110599ChEMBL, NPASS
TAR_EXP_000004ENSG00000094631HDAC610013ChEMBL
TAR_EXP_000214ENSG00000282608ADORA3140ChEMBL
TAR_EXP_000239ENSG00000120907ADRA1A148ChEMBL
TAR_EXP_000243ENSG00000150594ADRA2A150ChEMBL
TAR_EXP_000280ENSG00000160868CYP3A41576ChEMBL, NPASS
TAR_EXP_000276ENSG00000272532CYP2D61565ChEMBL, NPASS
TAR_EXP_000182ENSG00000023839ABCC21244ChEMBL, NPASS
TAR_EXP_000039ENSG00000125257ABCC410257BindingDB, NPASS
TAR_EXP_000130ENSG00000181072CHRM21129ChEMBL
TAR_EXP_000127ENSG00000168539CHRM11128ChEMBL
TAR_EXP_000132ENSG00000137491SLCO2B111309NPASS