IMPPAT Phytochemical information: 
Nigellimine n-oxide

Nigellimine n-oxide
Summary

SMILES: COc1cc2c(cc1OC)cc[n+](c2C)[O-]
InChI: InChI=1S/C12H13NO3/c1-8-10-7-12(16-3)11(15-2)6-9(10)4-5-13(8)14/h4-7H,1-3H3
InChIKey: GVQWAJKTFATJEW-UHFFFAOYSA-N
DeepSMILES: COcccccc6OC))))cc[n+]c6C))[O-]
Scaffold Graph/Node/Bond level: c1ccc2c[nH+]ccc2c1
Scaffold Graph/Node level: C1CCC2CNCCC2C1
Scaffold Graph level: C1CCC2CCCCC2C1
Functional groups: cOC; c[n+]([O-])c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Isoquinolines and derivatives
Synonymous chemical names:
Nigellimine N-oxide
Chemical structure download


Nigellimine n-oxide
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 219.24
Log P RDKit 1.8
Topological polar surface area (Å2) RDKit 45.4
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 12
Number of heavy atoms RDKit 16
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 3
Shape complexity RDKit 0.25
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 2
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 2


Nigellimine 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 0.57


Nigellimine n-oxide
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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.61
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No