IMPPAT Phytochemical information: 
Nigellicine

Nigellicine
Summary

SMILES: Cc1cc(=O)c2-c(c1)n1CCCCn1c2C(=O)O
InChI: InChI=1S/C13H14N2O3/c1-8-6-9-11(10(16)7-8)12(13(17)18)15-5-3-2-4-14(9)15/h6-7H,2-5H2,1H3,(H,17,18)
InChIKey: FEJTUHSIRAJLOJ-UHFFFAOYSA-N
DeepSMILES: Cccc=O)c-cc6)nCCCCn6c9C=O)O
Scaffold Graph/Node/Bond level: O=c1cccc2n3n(cc1-2)CCCC3
Scaffold Graph/Node level: OC1CCCC2C1CN1CCCCN21
Scaffold Graph level: CC1CCCC2C1CC1CCCCC12
Functional groups: c=O; cn(n(c)C)C; cC(=O)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:
Nigellicine, nigellicine
External chemical identifiers:
CID:CID_11402337; ChEBI:CHEBI:168947; ZINC:ZINC000195853999
Chemical structure download


Nigellicine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 246.27
Log P RDKit 1.56
Topological polar surface area (Å2) RDKit 64.23
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 13
Number of heavy atoms RDKit 18
Number of heteroatoms RDKit 5
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 8
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.38
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 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 3
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 3


Nigellicine
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 0.829974


Nigellicine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.85
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 -6.82
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No