IMPPAT Phytochemical information: 
gamma-Fagarine

gamma-Fagarine
Summary

SMILES: COc1cccc2c1nc1occc1c2OC
InChI: InChI=1S/C13H11NO3/c1-15-10-5-3-4-8-11(10)14-13-9(6-7-17-13)12(8)16-2/h3-7H,1-2H3
InChIKey: KFBCTNNQFGONHB-UHFFFAOYSA-N
DeepSMILES: COcccccc6ncoccc5c9OC
Scaffold Graph/Node/Bond level: c1ccc2nc3occc3cc2c1
Scaffold Graph/Node level: C1CCC2NC3OCCC3CC2C1
Scaffold Graph level: C1CCC2CC3CCCC3CC2C1
Functional groups: cnc; cOC; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Quinolines and derivatives
ClassyFire Subclass: Furanoquinolines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids|Anthranilic acid alkaloids
NP Classifier Class: Quinoline alkaloids
Synonymous chemical names:
Fagarine, gamma-, Fagarine,gamma-, fagarine, fagarin, gamma fagarine, gamma-fagarine, γ-fagarine
External chemical identifiers:
CID:CID_107936; ChEMBL:CHEMBL252925; ChEBI:CHEBI:10562; ZINC:ZINC000000199415; FDASRS:GKS8Q870TY; SureChEMBL:SCHEMBL679918; MolPort-002-112-260
Chemical structure download


gamma-Fagarine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 229.24
Log P RDKit 3
Topological polar surface area (Å2) RDKit 44.49
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 13
Number of heavy atoms RDKit 17
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 11
Number of sp3 hybridized carbon atoms RDKit 2
Shape complexity RDKit 0.15
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 2
Number of aromatic rings RDKit 3
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


gamma-Fagarine
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 0.68


gamma-Fagarine
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 -5.66
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No