IMPPAT Phytochemical information: 
Isopiline

Isopiline
Summary

SMILES: COc1c(O)c2-c3ccccc3C[C@@H]3c2c(c1OC)CCN3
InChI: InChI=1S/C18H19NO3/c1-21-17-12-7-8-19-13-9-10-5-3-4-6-11(10)15(14(12)13)16(20)18(17)22-2/h3-6,13,19-20H,7-9H2,1-2H3/t13-/m1/s1
InChIKey: XLXSXOHBVGWKMT-CYBMUJFWSA-N
DeepSMILES: COccO)c-cccccc6C[C@@H]c%10cc%14OC)))CCN6
Scaffold Graph/Node/Bond level: c1ccc2c(c1)CC1NCCc3cccc-2c31
Scaffold Graph/Node level: C1CCC2C(C1)CC1NCCC3CCCC2C31
Scaffold Graph level: C1CCC2C(C1)CC1CCCC3CCCC2C31
Functional groups: cOC; cO; CNC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Aporphines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Aporphine alkaloids|Isoquinoline alkaloids
Synonymous chemical names:
isopiline, Isopiline
External chemical identifiers:
CID:CID_13891896; ChEMBL:CHEMBL508011; ZINC:ZINC000014775234
Chemical structure download


Isopiline
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 297.35
Log P RDKit 2.82
Topological polar surface area (Å2) RDKit 50.72
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 22
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.06
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.33
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4


Isopiline
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 0.89474


Isopiline
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 -6.26
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes