IMPPAT Phytochemical information: 
10-Demethylcephaeline
10-Demethylcephaeline
Summary

SMILES: CC[C@H]1CN2CCc3c([C@@H]2C[C@@H]1C[C@H]1NCCc2c1cc(OC)c(c2)O)cc(c(c3)OC)O
InChI: InChI=1S/C27H36N2O4/c1-4-16-15-29-8-6-18-12-26(32-2)25(31)13-21(18)23(29)10-19(16)9-22-20-14-27(33-3)24(30)11-17(20)5-7-28-22/h11-14,16,19,22-23,28,30-31H,4-10,15H2,1-3H3/t16-,19-,22+,23-/m0/s1
InChIKey: QBNRQKFLWJOWBD-IKPGRFEGSA-N
DeepSMILES: CC[C@H]CNCCcc[C@@H]6C[C@@H]%10C[C@H]NCCcc6ccOC))cc6)O))))))))))))))cccc6)OC)))O
Scaffold Graph/Node/Bond level: c1ccc2c(c1)CCNC2CC1CCN2CCc3ccccc3C2C1
Scaffold Graph/Node level: C1CCC2C(C1)CCNC2CC1CCN2CCC3CCCCC3C2C1
Scaffold Graph level: C1CCC2C(C1)CCCC2CC1CCC2CCC3CCCCC3C2C1
Functional groups: cO; CN(C)C; CNC; cOC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Emetine alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Isoquinoline alkaloids
Synonymous chemical names:
10-o-emethylcephaeline, 10-demethylcephaeline
External chemical identifiers:
CID:CID_185699; ZINC:ZINC000031502618
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
10-Demethylcephaeline
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 452.6
Log P RDKit 4.34
Topological polar surface area (Å2) RDKit 74.19
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 27
Number of heavy atoms RDKit 33
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.15
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 15
Shape complexity RDKit 0.56
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
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 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
10-Demethylcephaeline
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 Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.62688
10-Demethylcephaeline
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.16
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes