IMPPAT Phytochemical information: 
Gentianine

Gentianine
Summary

SMILES: C=Cc1cncc2c1CCOC2=O
InChI: InChI=1S/C10H9NO2/c1-2-7-5-11-6-9-8(7)3-4-13-10(9)12/h2,5-6H,1,3-4H2
InChIKey: DFNZYFAJQPLJFI-UHFFFAOYSA-N
DeepSMILES: C=Cccnccc6CCOC6=O
Scaffold Graph/Node/Bond level: O=C1OCCc2ccncc21
Scaffold Graph/Node level: OC1OCCC2CCNCC21
Scaffold Graph level: CC1CCCC2CCCCC12
Functional groups: cC=C; cnc; cC(=O)OC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Pyranopyridines
NP Classifier Biosynthetic pathway: Alkaloids|Terpenoids
NP Classifier Superclass: Nicotinic acid alkaloids|Pseudoalkaloids
NP Classifier Class: Pyridine alkaloids|Terpenoid alkaloids
Synonymous chemical names:
Gentianine, gentianine
External chemical identifiers:
CID:CID_354616; ChEBI:CHEBI:28981; ZINC:ZINC000001530467; FDASRS:C2PD310UXB; SureChEMBL:SCHEMBL2216852; MolPort-002-507-225
Chemical structure download


Gentianine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 175.19
Log P RDKit 1.44
Topological polar surface area (Å2) RDKit 39.19
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 10
Number of heavy atoms RDKit 13
Number of heteroatoms RDKit 3
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 8
Number of sp3 hybridized carbon atoms RDKit 2
Shape complexity RDKit 0.2
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 1
Total number of rings RDKit 2
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 2


Gentianine
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 0.606042


Gentianine
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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.30
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 No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No