IMPPAT Phytochemical information: 
N-Desmethoxyrankinidine

N-Desmethoxyrankinidine
Summary

SMILES: C/C=C/1\CNC2C3C1CC(OC3)C1(C2)C(=O)Nc2c1cccc2
InChI: InChI=1S/C19H22N2O2/c1-2-11-9-20-16-8-19(17-7-12(11)13(16)10-23-17)14-5-3-4-6-15(14)21-18(19)22/h2-6,12-13,16-17,20H,7-10H2,1H3,(H,21,22)/b11-2+
InChIKey: YIOBXNAEUXWNQS-BIIKFXOESA-N
DeepSMILES: C/C=C\CNCCC\6CCOC6))CC7)C=O)Ncc5cccc6
Scaffold Graph/Node/Bond level: C=C1CNC2CC3(C(=O)Nc4ccccc43)C3CC1C2CO3
Scaffold Graph/Node level: CC1CNC2CC3(C(O)NC4CCCCC43)C3CC1C2CO3
Scaffold Graph level: CC1CCC2CC3(C(C)CC4CCCCC43)C3CCC2C1C3
Functional groups: C/C=C(\C)C; CNC; COC; cNC(=O)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Gelsemium alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Corynanthe type
Synonymous chemical names:
n-desmethoxyrankinidine
External chemical identifiers:
CID:CID_5316594
Chemical structure download


N-Desmethoxyrankinidine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 310.4
Log P RDKit 2.22
Topological polar surface area (Å2) RDKit 50.36
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.26
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.53
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 3
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6


N-Desmethoxyrankinidine
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 Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.722536


N-Desmethoxyrankinidine
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 -7.46
Number of PAINS structural alerts SwissADME 0
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