IMPPAT Phytochemical information: 
Cinchonicinol

Cinchonicinol
Summary

SMILES: C=C[C@H]1CNCC[C@H]1CC[C@@H](c1ccnc2c1cccc2)O
InChI: InChI=1S/C19H24N2O/c1-2-14-13-20-11-9-15(14)7-8-19(22)17-10-12-21-18-6-4-3-5-16(17)18/h2-6,10,12,14-15,19-20,22H,1,7-9,11,13H2/t14-,15+,19-/m0/s1
InChIKey: IIBQKFKYTJHZOZ-KHYOSLBOSA-N
DeepSMILES: C=C[C@H]CNCC[C@H]6CC[C@@H]cccncc6cccc6))))))))))O
Scaffold Graph/Node/Bond level: c1ccc2c(CCCC3CCNCC3)ccnc2c1
Scaffold Graph/Node level: C(CC1CCNCC1)CC1CCNC2CCCCC12
Scaffold Graph level: C1CCC(CCCC2CCCC3CCCCC32)CC1
Functional groups: C=CC; CNC; cnc; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Quinolines and derivatives
ClassyFire Subclass: 4-quinolinemethanols
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
Synonymous chemical names:
cinchonicinol
External chemical identifiers:
CID:CID_10469865; ZINC:ZINC000014684830; SureChEMBL:SCHEMBL11289121
Chemical structure download


Cinchonicinol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 296.41
Log P RDKit 3.46
Topological polar surface area (Å2) RDKit 45.15
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 2
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 3
Stereochemical complexity RDKit 0.16
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 5
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3


Cinchonicinol
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 0.830592


Cinchonicinol
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 -6.04
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes