IMPPAT Phytochemical information: 
Scopoline

Scopoline
Summary

SMILES: CN1C2CC3CC1C(C2O)O3
InChI: InChI=1S/C8H13NO2/c1-9-5-2-4-3-6(9)8(11-4)7(5)10/h4-8,10H,2-3H2,1H3
InChIKey: MEGPURSNXMUDAE-UHFFFAOYSA-N
DeepSMILES: CNCCCCC6CC7O))O5
Scaffold Graph/Node/Bond level: C1C2CC3OC1CC3N2
Scaffold Graph/Node level: C1C2CC3OC1CC3N2
Scaffold Graph level: C1C2CC3CC1CC3C2
Functional groups: CN(C)C; COC; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Oxazepines
ClassyFire Subclass: 1,4-oxazepines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Ornithine alkaloids
NP Classifier Class: Tropane alkaloids
Synonymous chemical names:
Scopoline, oscin, scopoline
External chemical identifiers:
CID:CID_261184; ChEMBL:CHEMBL1394721; SureChEMBL:SCHEMBL12618459; MolPort-006-151-182
Chemical structure download


Scopoline
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 155.2
Log P RDKit -0.41
Topological polar surface area (Å2) RDKit 32.7
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 8
Number of heavy atoms RDKit 11
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.62
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 0
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 1
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 4
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4


Scopoline
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 3
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.52


Scopoline
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -7.39
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No