IMPPAT Phytochemical information: 
Nigellidine

Nigellidine
Summary

SMILES: Cc1cc(=O)c2-c(c1)n1CCCCn1c2c1ccc(cc1)O
InChI: InChI=1S/C18H18N2O2/c1-12-10-15-17(16(22)11-12)18(13-4-6-14(21)7-5-13)20-9-3-2-8-19(15)20/h4-7,10-11,21H,2-3,8-9H2,1H3
InChIKey: HJKNBAAMIKPHJF-UHFFFAOYSA-N
DeepSMILES: Cccc=O)c-cc6)nCCCCn6c9cccccc6))O
Scaffold Graph/Node/Bond level: O=c1cccc2n3n(c(-c4ccccc4)c1-2)CCCC3
Scaffold Graph/Node level: OC1CCCC2C1C(C1CCCCC1)N1CCCCN21
Scaffold Graph level: CC1CCCC2C3CCCCC3C(C3CCCCC3)C12
Functional groups: cn(n(c)C)C; cO; c=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Benzopyrazoles
ClassyFire Subclass: Indazoles
NP Classifier Biosynthetic pathway: Alkaloids
Synonymous chemical names:
Nigellidine, nigellidine
External chemical identifiers:
CID:CID_136828302
Chemical structure download


Nigellidine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 294.35
Log P RDKit 3.23
Topological polar surface area (Å2) RDKit 47.16
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 2
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 13
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.28
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 2
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


Nigellidine
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 0.748754


Nigellidine
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 -6.02
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 No
P-glycoprotein substrate SwissADME Yes