IMPPAT Phytochemical information: 
Lobelanine

Lobelanine
Summary

SMILES: CN1[C@H](CCC[C@H]1CC(=O)c1ccccc1)CC(=O)c1ccccc1
InChI: InChI=1S/C22H25NO2/c1-23-19(15-21(24)17-9-4-2-5-10-17)13-8-14-20(23)16-22(25)18-11-6-3-7-12-18/h2-7,9-12,19-20H,8,13-16H2,1H3/t19-,20+
InChIKey: IDEMKXUAULKYJV-BGYRXZFFSA-N
DeepSMILES: CN[C@H]CCC[C@H]6CC=O)cccccc6))))))))))))CC=O)cccccc6
Scaffold Graph/Node/Bond level: O=C(CC1CCCC(CC(=O)c2ccccc2)N1)c1ccccc1
Scaffold Graph/Node level: OC(CC1CCCC(CC(O)C2CCCCC2)N1)C1CCCCC1
Scaffold Graph level: CC(CC1CCCC(CC(C)C2CCCCC2)C1)C1CCCCC1
Functional groups: CN(C)C; cC(C)=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Carbonyl compounds
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Lysine alkaloids
NP Classifier Class: Piperidine alkaloids
Synonymous chemical names:
lobelanine, Lobelanine
External chemical identifiers:
CID:CID_442647; ChEMBL:CHEMBL331161; ChEBI:CHEBI:6508; ZINC:ZINC000008463982; FDASRS:4XWB84090T; SureChEMBL:SCHEMBL3448367; MolPort-019-998-919
Chemical structure download


Lobelanine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 335.45
Log P RDKit 4.39
Topological polar surface area (Å2) RDKit 37.38
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.09
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 14
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.36
Number of rotatable bonds RDKit 6
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 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3


Lobelanine
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 Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.74


Lobelanine
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 -5.60
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No