IMPPAT Phytochemical information: 
(4S)-10,11-dimethoxyspiro[5-azatricyclo[6.3.1.04,12]dodeca-1(12),8,10-triene-2,4'-cyclohexa-2,5-diene]-1'-one
(4S)-10,11-dimethoxyspiro[5-azatricyclo[6.3.1.04,12]dodeca-1(12),8,10-triene-2,4'-cyclohexa-2,5-diene]-1'-one
Summary

SMILES: COc1c(OC)cc2c3c1C1(C=CC(=O)C=C1)C[C@@H]3NCC2
InChI: InChI=1S/C18H19NO3/c1-21-14-9-11-5-8-19-13-10-18(6-3-12(20)4-7-18)16(15(11)13)17(14)22-2/h3-4,6-7,9,13,19H,5,8,10H2,1-2H3/t13-/m0/s1
InChIKey: OGJKMZVUJJYWKO-ZDUSSCGKSA-N
DeepSMILES: COccOC))cccc6CC=CC=O)C=C6)))))C[C@@H]5NCC9
Scaffold Graph/Node/Bond level: O=C1C=CC2(C=C1)CC1NCCc3cccc2c31
Scaffold Graph/Node level: OC1CCC2(CC1)CC1NCCC3CCCC2C31
Scaffold Graph level: CC1CCC2(CC1)CC1CCCC3CCCC2C31
Functional groups: cOC; O=C1C=CCC=C1; CNC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Proaporphines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Isoquinoline alkaloids
Synonymous chemical names:
Stepharine, stepharine
External chemical identifiers:
CID:CID_830726; ChEMBL:CHEMBL463957; ZINC:ZINC000026787150
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(4S)-10,11-dimethoxyspiro[5-azatricyclo[6.3.1.04,12]dodeca-1(12),8,10-triene-2,4'-cyclohexa-2,5-diene]-1'-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 297.35
Log P RDKit 2.23
Topological polar surface area (Å2) RDKit 47.56
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
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 11
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.39
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
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
(4S)-10,11-dimethoxyspiro[5-azatricyclo[6.3.1.04,12]dodeca-1(12),8,10-triene-2,4'-cyclohexa-2,5-diene]-1'-one
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 0
Ghose rule RDKit Passed
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 0.91
(4S)-10,11-dimethoxyspiro[5-azatricyclo[6.3.1.04,12]dodeca-1(12),8,10-triene-2,4'-cyclohexa-2,5-diene]-1'-one
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 -6.64
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 Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes