IMPPAT Phytochemical information: 
Graveolinine

Graveolinine
Summary

SMILES: COc1cc(nc2c1cccc2)c1ccc2c(c1)OCO2
InChI: InChI=1S/C17H13NO3/c1-19-16-9-14(18-13-5-3-2-4-12(13)16)11-6-7-15-17(8-11)21-10-20-15/h2-9H,10H2,1H3
InChIKey: QGCORDIPOBZNKC-UHFFFAOYSA-N
DeepSMILES: COcccncc6cccc6)))))))cccccc6)OCO5
Scaffold Graph/Node/Bond level: c1ccc2nc(-c3ccc4c(c3)OCO4)ccc2c1
Scaffold Graph/Node level: C1CCC2NC(C3CCC4OCOC4C3)CCC2C1
Scaffold Graph level: C1CCC2CC(C3CCC4CCCC4C3)CCC2C1
Functional groups: cOC; cnc; c1cOCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Quinolines and derivatives
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Anthranilic acid alkaloids
Synonymous chemical names:
Graveolinine, graveolinine
External chemical identifiers:
CID:CID_11044132; ChEMBL:CHEMBL2205100; ChEBI:CHEBI:173977; ZINC:ZINC000005386772
Chemical structure download


Graveolinine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 279.3
Log P RDKit 3.64
Topological polar surface area (Å2) RDKit 40.58
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 17
Number of heavy atoms RDKit 21
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 15
Number of sp3 hybridized carbon atoms RDKit 2
Shape complexity RDKit 0.12
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 4
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 4


Graveolinine
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 0.717792


Graveolinine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.25
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 Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes