IMPPAT Phytochemical information: 
Lobelanidine

Lobelanidine
Summary

SMILES: O[C@H](c1ccccc1)C[C@@H]1CCC[C@@H](N1C)C[C@H](c1ccccc1)O
InChI: InChI=1S/C22H29NO2/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/h2-7,9-12,19-22,24-25H,8,13-16H2,1H3/t19-,20+,21-,22+
InChIKey: OWGJQNXIWMMDTH-COPRSSIGSA-N
DeepSMILES: O[C@H]cccccc6))))))C[C@@H]CCC[C@@H]N6C))C[C@H]cccccc6))))))O
Scaffold Graph/Node/Bond level: c1ccc(CCC2CCCC(CCc3ccccc3)N2)cc1
Scaffold Graph/Node level: C1CCC(CCC2CCCC(CCC3CCCCC3)N2)CC1
Scaffold Graph level: C1CCC(CCC2CCCC(CCC3CCCCC3)C2)CC1
Functional groups: CO; CN(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic nitrogen compounds
ClassyFire Class: Organonitrogen compounds
ClassyFire Subclass: Amines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Lysine alkaloids
NP Classifier Class: Piperidine alkaloids
Synonymous chemical names:
Lobelanidine, lobelanidine
External chemical identifiers:
CID:CID_442646; ChEMBL:CHEMBL122676; ChEBI:CHEBI:6507; ZINC:ZINC000004098588; FDASRS:J3ZM7K5LNB; SureChEMBL:SCHEMBL893510
Chemical structure download


Lobelanidine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 339.48
Log P RDKit 4.09
Topological polar surface area (Å2) RDKit 43.7
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 2
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 4
Stereochemical complexity RDKit 0.18
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.45
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


Lobelanidine
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 0.83


Lobelanidine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately 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 -5.79
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 Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes