IMPPAT Phytochemical information: 
Lobinaline

Lobinaline
Summary

SMILES: CN1CCCC2C1CC(c1ccccc1)C(C2c1ccccc1)C1=NCCCC1
InChI: InChI=1S/C27H34N2/c1-29-18-10-15-22-25(29)19-23(20-11-4-2-5-12-20)27(24-16-8-9-17-28-24)26(22)21-13-6-3-7-14-21/h2-7,11-14,22-23,25-27H,8-10,15-19H2,1H3
InChIKey: MVIXAPHJOKOOEU-UHFFFAOYSA-N
DeepSMILES: CNCCCCC6CCcccccc6))))))CC6cccccc6)))))))C=NCCCC6
Scaffold Graph/Node/Bond level: c1ccc(C2CC3NCCCC3C(c3ccccc3)C2C2=NCCCC2)cc1
Scaffold Graph/Node level: C1CCC(C2CC3NCCCC3C(C3CCCCC3)C2C2CCCCN2)CC1
Scaffold Graph level: C1CCC(C2CC3CCCCC3C(C3CCCCC3)C2C2CCCCC2)CC1
Functional groups: CN=C(C)C; CN(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Quinolines and derivatives
ClassyFire Subclass: Phenylquinolines
NP Classifier Biosynthetic pathway: Alkaloids
Synonymous chemical names:
lobinaline
External chemical identifiers:
CID:CID_419029; ChEMBL:CHEMBL2010381
Chemical structure download


Lobinaline
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 386.58
Log P RDKit 5.91
Topological polar surface area (Å2) RDKit 15.6
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 27
Number of heavy atoms RDKit 29
Number of heteroatoms RDKit 2
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.19
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 14
Shape complexity RDKit 0.52
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5


Lobinaline
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 1
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.64


Lobinaline
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 -5.24
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 Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No