IMPPAT Phytochemical information: 
Litseferine

Litseferine
Summary

SMILES: COc1cc2C[C@@H]3NCCc4c3c(-c2cc1O)c1OCOc1c4
InChI: InChI=1S/C18H17NO4/c1-21-14-6-10-4-12-16-9(2-3-19-12)5-15-18(23-8-22-15)17(16)11(10)7-13(14)20/h5-7,12,19-20H,2-4,8H2,1H3/t12-/m0/s1
InChIKey: NWCGFAYLTGJNLQ-LBPRGKRZSA-N
DeepSMILES: COcccC[C@@H]NCCcc6c-c%10cc%14O))))cOCOc5c9
Scaffold Graph/Node/Bond level: c1ccc2c(c1)CC1NCCc3cc4c(c-2c31)OCO4
Scaffold Graph/Node level: C1CCC2C(C1)CC1NCCC3CC4OCOC4C2C31
Scaffold Graph level: C1CCC2C(C1)CC1CCCC3CC4CCCC4C2C13
Functional groups: cOC; CNC; cO; 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:
litseferine
External chemical identifiers:
CID:CID_13891936; ZINC:ZINC000013451327
Chemical structure download


Litseferine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 311.34
Log P RDKit 2.54
Topological polar surface area (Å2) RDKit 59.95
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 23
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 0.06
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.33
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 5
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 5


Litseferine
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 0.85


Litseferine
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 -6.46
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 Yes
P-glycoprotein substrate SwissADME Yes