IMPPAT Phytochemical information: 
Lochnerinine
Lochnerinine
Summary

SMILES: COc1ccc2c(c1)NC1=C(C[C@]3([C@H]4[C@@]21CCN4CC1C3O1)CC)C(=O)OC
InChI: InChI=1S/C22H26N2O4/c1-4-21-10-13(19(25)27-3)17-22(14-6-5-12(26-2)9-15(14)23-17)7-8-24(20(21)22)11-16-18(21)28-16/h5-6,9,16,18,20,23H,4,7-8,10-11H2,1-3H3/t16?,18?,20-,21+,22-/m0/s1
InChIKey: YKTXUUJZENEUGL-MKHRZCKRSA-N
DeepSMILES: COcccccc6)NC=CC[C@][C@H][C@@]96CCN5CCC9O3)))))))))CC))))C=O)OC
Scaffold Graph/Node/Bond level: C1=C2Nc3ccccc3C23CCN2CC4OC4C(C1)C23
Scaffold Graph/Node level: C1CCC2C(C1)NC1CCC3C4OC4CN4CCC12C34
Scaffold Graph level: C1CCC2C(C1)CC1CCC3C4CC4CC4CCC12C43
Functional groups: cOC; cNC(=C(C(=O)OC)C)C; CN(C)C; CC1OC1C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Aspidospermatan-type alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Aspidosperma type
Synonymous chemical names:
Lochnerinine, lochnerinine, lochneririne
External chemical identifiers:
CID:CID_443417; ChEBI:CHEBI:6511; SureChEMBL:SCHEMBL4143036
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Lochnerinine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 382.46
Log P RDKit 2.44
Topological polar surface area (Å2) RDKit 63.33
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 28
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.23
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.59
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 3
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6
Lochnerinine
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 0.64002
Lochnerinine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME 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 -6.86
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No