IMPPAT Phytochemical information: 
Neolitsine

Neolitsine
Summary

SMILES: CN1CCc2c3[C@@H]1Cc1cc4OCOc4cc1-c3c1c(c2)OCO1
InChI: InChI=1S/C19H17NO4/c1-20-3-2-10-5-16-19(24-9-23-16)18-12-7-15-14(21-8-22-15)6-11(12)4-13(20)17(10)18/h5-7,13H,2-4,8-9H2,1H3/t13-/m0/s1
InChIKey: GKEOKAJRKHTDOS-ZDUSSCGKSA-N
DeepSMILES: CNCCcc[C@@H]6CcccOCOc5cc9-c%13ccc%17)OCO5
Scaffold Graph/Node/Bond level: c1c2c(cc3c1OCO3)-c1c3c(cc4c1C(C2)NCC4)OCO3
Scaffold Graph/Node level: C1CC2CC3OCOC3C3C4CC5OCOC5CC4CC(N1)C23
Scaffold Graph level: C1CC2CC3CC4CCCC5CC6CCCC6C(C3CC2C1)C54
Functional groups: CN(C)C; c1cOCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Aporphines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Aporphine alkaloids|Isoquinoline alkaloids
Synonymous chemical names:
neolitsine
External chemical identifiers:
CID:CID_10064778; ChEMBL:CHEMBL404684; ZINC:ZINC000014613037; MolPort-044-723-349
Chemical structure download


Neolitsine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 323.35
Log P RDKit 2.9
Topological polar surface area (Å2) RDKit 40.16
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 24
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.05
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.37
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6


Neolitsine
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 0.75


Neolitsine
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 -6.06
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No