IMPPAT Phytochemical information: 
Virgiline

Virgiline
Summary

SMILES: O[C@H]1CCN2[C@@H](C1)[C@H]1C[C@@H](C2)[C@@H]2N(C1=O)CCCC2
InChI: InChI=1S/C15H24N2O2/c18-11-4-6-16-9-10-7-12(14(16)8-11)15(19)17-5-2-1-3-13(10)17/h10-14,18H,1-9H2/t10-,11-,12+,13+,14-/m0/s1
InChIKey: UGCQEPKCDSOOAO-QNSTZXKLSA-N
DeepSMILES: O[C@H]CCN[C@@H]C6)[C@H]C[C@@H]C6)[C@@H]NC6=O))CCCC6
Scaffold Graph/Node/Bond level: O=C1C2CC(CN3CCCCC23)C2CCCCN12
Scaffold Graph/Node level: OC1C2CC(CN3CCCCC23)C2CCCCN12
Scaffold Graph level: CC1C2CCCCC2C2CC3CCCCC3C1C2
Functional groups: CO; CN(C)C; CN(C)C(=O)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Lupin alkaloids
ClassyFire Subclass: Sparteine, lupanine, and related alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Lysine alkaloids
NP Classifier Class: Quinolizidine alkaloids
Synonymous chemical names:
Virgiline, virgiline
External chemical identifiers:
CID:CID_12444870; ZINC:ZINC000238755841
Chemical structure download


Virgiline
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 264.37
Log P RDKit 0.84
Topological polar surface area (Å2) RDKit 43.78
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 19
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.33
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 1
Number of sp3 hybridized carbon atoms RDKit 14
Shape complexity RDKit 0.93
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 4
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4


Virgiline
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 0.705014


Virgiline
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.39
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 Yes