IMPPAT Phytochemical information: 
Nilgirine
Nilgirine
Summary

SMILES: C/C=C/1\CC(C)C(O)C(=O)OCC2=C3C(OC1=O)CCN3CC2
InChI: InChI=1S/C17H23NO5/c1-3-11-8-10(2)15(19)17(21)22-9-12-4-6-18-7-5-13(14(12)18)23-16(11)20/h3,10,13,15,19H,4-9H2,1-2H3/b11-3+
InChIKey: CRDPLWCMWMJVFE-QDEBKDIKSA-N
DeepSMILES: C/C=C\CCC)CO)C=O)OCC=CCOC\%12=O)))CCN5CC8
Scaffold Graph/Node/Bond level: C=C1CCCC(=O)OCC2=C3C(CCN3CC2)OC1=O
Scaffold Graph/Node level: CC1CCCC(O)OCC2CCN3CCC(OC1O)C23
Scaffold Graph level: CC1CCCC(C)C(C)CC2CCC3CCC(CC1)C32
Functional groups: C/C=C(\C)C(=O)OC; CO; COC(=O)C; CC1=C(C)N(C)CC1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic acids and derivatives
ClassyFire Class: Carboxylic acids and derivatives
ClassyFire Subclass: Dicarboxylic acids and derivatives
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Ornithine alkaloids
NP Classifier Class: Pyrrolizidine alkaloids
Synonymous chemical names:
Nilgirine
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Nilgirine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 321.37
Log P RDKit 1.15
Topological polar surface area (Å2) RDKit 76.07
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 17
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.18
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 6
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.65
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
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 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3
Nilgirine
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 Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.53
Nilgirine
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 No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.48
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 No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No