IMPPAT Phytochemical information: 
Venalstonidine

Venalstonidine
Summary

SMILES: COC(=O)[C@@H]1C[C@]23CC[C@]41Nc1c(C54[C@H]3N(CC5)C[C@H]3[C@@H]2O3)cccc1
InChI: InChI=1S/C21H24N2O3/c1-25-17(24)13-10-19-6-7-21(13)20(12-4-2-3-5-14(12)22-21)8-9-23(18(19)20)11-15-16(19)26-15/h2-5,13,15-16,18,22H,6-11H2,1H3/t13-,15-,16-,18-,19+,20?,21+/m0/s1
InChIKey: PKVIZXKEMISSGB-JDGDXTPDSA-N
DeepSMILES: COC=O)[C@@H]C[C@@]CC[C@@]6NccC5[C@H]9NCC5))C[C@H][C@@H]%13O3)))))))cccc6
Scaffold Graph/Node/Bond level: c1ccc2c(c1)NC13CCC4(CC1)C1OC1CN1CCC23C14
Scaffold Graph/Node level: C1CCC2C(C1)NC13CCC4(CC1)C1OC1CN1CCC23C14
Scaffold Graph level: C1CCC2C(C1)CC13CCC4(CC1)C1CC1CC1CCC23C14
Functional groups: COC(C)=O; cNC; CN(C)C; C[C@@H]1O[C@@H]1C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Aspidofractine alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Aspidosperma type
Synonymous chemical names:
Venalstonidine
External chemical identifiers:
CID:CID_176438
Chemical structure download


Venalstonidine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 352.43
Log P RDKit 1.92
Topological polar surface area (Å2) RDKit 54.1
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 7
Stereochemical complexity RDKit 0.33
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 14
Shape complexity RDKit 0.67
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 7
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 8
Number of saturated carbocycles RDKit 3
Number of saturated heterocycles RDKit 3
Number of saturated rings RDKit 6
Number of Smallest Set of Smallest Rings (SSSR) RDKit 8


Venalstonidine
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 0.618164


Venalstonidine
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 -7.04
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 No