IMPPAT Phytochemical information: 
Koumine N-oxide

Koumine N-oxide
Summary

SMILES: C=CC12C[N+]([O-])(C)C3C4C1CC(C1=Nc5c(C21C3)cccc5)OC4
InChI: InChI=1S/C20H22N2O2/c1-3-19-11-22(2,23)16-9-20(19)13-6-4-5-7-15(13)21-18(20)17-8-14(19)12(16)10-24-17/h3-7,12,14,16-17H,1,8-11H2,2H3
InChIKey: OISZCFMVBRTVHR-UHFFFAOYSA-N
DeepSMILES: C=CCC[N+][O-])C)CCC6CCC=NccC%135C%11))cccc6))))))))OC6
Scaffold Graph/Node/Bond level: c1ccc2c(c1)N=C1C3CC4C(CO3)C3CC12C4C[NH2+]3
Scaffold Graph/Node level: C1CCC2C(C1)NC1C3CC4C(CO3)C3CC21C4CN3
Scaffold Graph level: C1CCC2C(C1)CC1C3CCC4C5CCC(C4C3)C21C5
Functional groups: C=CC; C[N+](C)([O-])C; cN=C(C)C; COC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Indoles and derivatives
ClassyFire Subclass: Indoles
Synonymous chemical names:
koumine n-oxide
External chemical identifiers:
CID:CID_5318847
Chemical structure download


Koumine N-oxide
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 322.41
Log P RDKit 2.95
Topological polar surface area (Å2) RDKit 44.65
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 24
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 2
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 9
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.55
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 6
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 7
Number of saturated carbocycles RDKit 2
Number of saturated heterocycles RDKit 3
Number of saturated rings RDKit 5
Number of Smallest Set of Smallest Rings (SSSR) RDKit 7


Koumine N-oxide
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 0.45


Koumine N-oxide
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 -6.86
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes