IMPPAT Phytochemical information: 
Voaluteine

Voaluteine
Summary

SMILES: CCC1CC2CN3C1C(C2)(C(=O)OC)C1(CC3)Nc2c(C1=O)cc(cc2)OC
InChI: InChI=1S/C22H28N2O4/c1-4-14-9-13-11-21(20(26)28-3)18(14)24(12-13)8-7-22(21)19(25)16-10-15(27-2)5-6-17(16)23-22/h5-6,10,13-14,18,23H,4,7-9,11-12H2,1-3H3
InChIKey: ZZJBUKQZGMCYEE-UHFFFAOYSA-N
DeepSMILES: CCCCCCNC6CC6)C=O)OC)))CCC6))NccC5=O))cccc6))OC
Scaffold Graph/Node/Bond level: O=C1c2ccccc2NC12CCN1CC3CCC1C2C3
Scaffold Graph/Node level: OC1C2CCCCC2NC12CCN1CC3CCC1C2C3
Scaffold Graph level: CC1C2CCCCC2CC12CCC1CC3CCC1C2C3
Functional groups: CN(C)C; COC(C)=O; cNC; cC(=O)C; cOC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Quinolizidines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Iboga type
Synonymous chemical names:
pseudoindoxyl voacangine
External chemical identifiers:
CID:CID_633439
Chemical structure download


Voaluteine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 384.48
Log P RDKit 2.73
Topological polar surface area (Å2) RDKit 67.87
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 28
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 0.23
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 14
Shape complexity RDKit 0.64
Number of rotatable bonds RDKit 4
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


Voaluteine
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 0.808561


Voaluteine
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 -6.59
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No