IMPPAT Phytochemical information: 
11-Hydroxyrankinidine

11-Hydroxyrankinidine
Summary

SMILES: CON1c2cc(O)ccc2C2(C1=O)CC1NC/C(=C\C)/C3CC2OCC13
InChI: InChI=1S/C20H24N2O4/c1-3-11-9-21-16-8-20(18-7-13(11)14(16)10-26-18)15-5-4-12(23)6-17(15)22(25-2)19(20)24/h3-6,13-14,16,18,21,23H,7-10H2,1-2H3/b11-3+
InChIKey: FALAMCOLIJTCTR-QDEBKDIKSA-N
DeepSMILES: CONcccO)ccc6CC9=O))CCNC/C=C\C))/CCC9OCC%106
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: cN(OC)C(=O)C; cO; CNC; C/C=C(\C)C; COC
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:
11-hydroxyrankinidine
External chemical identifiers:
CID:CID_5318332
Chemical structure download


11-Hydroxyrankinidine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 356.42
Log P RDKit 1.88
Topological polar surface area (Å2) RDKit 71.03
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.25
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.55
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


11-Hydroxyrankinidine
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 0.752111


11-Hydroxyrankinidine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.84
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