IMPPAT Phytochemical information: 
Stephasunoline

Stephasunoline
Summary

SMILES: COC1C(O)CC23C4(C1(O)OC(C4)c1c3c(OC)c(cc1)OC)N(C)CC2
InChI: InChI=1S/C20H27NO6/c1-21-8-7-18-9-12(22)17(26-4)20(23)19(18,21)10-14(27-20)11-5-6-13(24-2)16(25-3)15(11)18/h5-6,12,14,17,22-23H,7-10H2,1-4H3
InChIKey: WOGSBUNWOTVHQN-UHFFFAOYSA-N
DeepSMILES: COCCO)CCCC6O)OCC5)cc7cOC))ccc6))OC)))))))))NC)CC5
Scaffold Graph/Node/Bond level: c1ccc2c(c1)C1CC34NCCC23CCCC4O1
Scaffold Graph/Node level: C1CCC2C(C1)C1CC34NCCC23CCCC4O1
Scaffold Graph level: C1CCC2C(C1)C1CC3CCCC24CCCC34C1
Functional groups: COC; CO; COC(O)(C)C; cOC; CN(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Hasubanan alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Hasubanan alkaloids
Synonymous chemical names:
stephasunoline
External chemical identifiers:
CID:CID_618654
Chemical structure download


Stephasunoline
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 377.44
Log P RDKit 0.96
Topological polar surface area (Å2) RDKit 80.62
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.3
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 6
Number of sp3 hybridized carbon atoms RDKit 14
Shape complexity RDKit 0.7
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5


Stephasunoline
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 Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.81207


Stephasunoline
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -8.39
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 Yes