IMPPAT Phytochemical information: 
Litcubine

Litcubine
Summary

SMILES: COc1cc2CC[N+]3(C(c2cc1O)Cc1c3cc(c(c1)OC)O)C
InChI: InChI=1S/C19H21NO4/c1-20-5-4-11-7-18(23-2)16(21)9-13(11)15(20)6-12-8-19(24-3)17(22)10-14(12)20/h7-10,15H,4-6H2,1-3H3,(H-,21,22)/p+1
InChIKey: CWKRVCVOEADAEH-UHFFFAOYSA-O
DeepSMILES: COcccCC[N+]Cc6cc%10O))))Ccc5cccc6)OC)))O)))))))C
Scaffold Graph/Node/Bond level: c1ccc2c(c1)CC[NH+]1c3ccccc3CC21
Scaffold Graph/Node level: C1CCC2C(C1)CCN1C3CCCCC3CC21
Scaffold Graph level: C1CCC2C(C1)CC1C3CCCCC3CCC21
Functional groups: cOC; c[N+](C)(C)C; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Tetrahydroisoquinolines
Synonymous chemical names:
litcubine
External chemical identifiers:
CID:CID_85243417; ChEBI:CHEBI:169824
Chemical structure download


Litcubine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 328.39
Log P RDKit 2.91
Topological polar surface area (Å2) RDKit 58.92
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 2
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 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 4
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 4


Litcubine
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


Litcubine
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 -6.41
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes