IMPPAT Phytochemical information: 
Lochnerine

Lochnerine
Summary

SMILES: OC[C@H]1[C@@H]2Cc3c([C@H]4N2C/C(=C/C)/[C@@H]1C4)[nH]c1c3cc(OC)cc1
InChI: InChI=1S/C20H24N2O2/c1-3-11-9-22-18-8-15-14-6-12(24-2)4-5-17(14)21-20(15)19(22)7-13(11)16(18)10-23/h3-6,13,16,18-19,21,23H,7-10H2,1-2H3/b11-3-/t13-,16+,18-,19-/m0/s1
InChIKey: YTIVOMMYBBBYFH-BOPWJTLDSA-N
DeepSMILES: OC[C@H][C@@H]Ccc[C@H]N6C/C=C/C))/[C@@H]%10C6))))))[nH]cc5ccOC))cc6
Scaffold Graph/Node/Bond level: C=C1CN2C3Cc4c([nH]c5ccccc45)C2CC1C3
Scaffold Graph/Node level: CC1CN2C3CC1CC2C1NC2CCCCC2C1C3
Scaffold Graph level: CC1CC2C3CC1CC2C1CC2CCCCC2C1C3
Functional groups: CO; CN(C)C; C/C=C(/C)C; c[nH]c; cOC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Macroline alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Corynanthe type
Synonymous chemical names:
lochnerine
External chemical identifiers:
CID:CID_6436184; ChEMBL:CHEMBL484153
Chemical structure download


Lochnerine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 324.42
Log P RDKit 3.03
Topological polar surface area (Å2) RDKit 48.49
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 24
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.2
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 10
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.5
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
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


Lochnerine
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 Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.83


Lochnerine
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 -6.82
Number of PAINS structural alerts SwissADME 1
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 No
P-glycoprotein substrate SwissADME Yes