IMPPAT Phytochemical information: 
Cinchonine

Cinchonine
Summary

SMILES: C=C[C@H]1CN2CC[C@H]1C[C@@H]2[C@H](c1ccnc2c1cccc2)O
InChI: InChI=1S/C19H22N2O/c1-2-13-12-21-10-8-14(13)11-18(21)19(22)16-7-9-20-17-6-4-3-5-15(16)17/h2-7,9,13-14,18-19,22H,1,8,10-12H2/t13-,14-,18+,19-/m0/s1
InChIKey: KMPWYEUPVWOPIM-QAMTZSDWSA-N
DeepSMILES: C=C[C@H]CNCC[C@H]6C[C@@H]6[C@H]cccncc6cccc6))))))))))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; 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:
cinchonin, cinchonine, Cinchonine
External chemical identifiers:
CID:CID_90454; ChEMBL:CHEMBL588619; ChEBI:CHEBI:27509; ZINC:ZINC000003881680; FDASRS:V43X79NZCD; SureChEMBL:SCHEMBL158394; MolPort-001-742-609
Chemical structure download


Cinchonine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 294.4
Log P RDKit 3.16
Topological polar surface area (Å2) RDKit 36.36
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 22
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.21
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 11
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.42
Number of rotatable bonds RDKit 3
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


Cinchonine
Drug-likeness properties
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 0.883424


Cinchonine
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 -6.19
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 Yes