IMPPAT Phytochemical information: 
Voaphylline hydroxyindolenine
Voaphylline hydroxyindolenine
Summary

SMILES: CC[C@]12CCC3=Nc4c([C@@]3(CCN(C1)C[C@@H]1[C@H]2O1)O)cccc4
InChI: InChI=1S/C19H24N2O2/c1-2-18-8-7-16-19(22,13-5-3-4-6-14(13)20-16)9-10-21(12-18)11-15-17(18)23-15/h3-6,15,17,22H,2,7-12H2,1H3/t15-,17-,18+,19-/m1/s1
InChIKey: ZTCJOOIYHFZAQO-OQIJWPOYSA-N
DeepSMILES: CC[C@]CCC=Ncc[C@@]5CCNC%12)C[C@@H][C@H]%14O3)))))))O))cccc6
Scaffold Graph/Node/Bond level: c1ccc2c(c1)N=C1CCC3CN(CCC12)CC1OC31
Scaffold Graph/Node level: C1CCC2C(C1)NC1CCC3CN(CCC12)CC1OC31
Scaffold Graph level: C1CCC2C(C1)CC1CCC3CC(CCC12)CC1CC31
Functional groups: cN=C(C)C; CN(C)C; C[C@H]1O[C@H]1C; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Indoles and derivatives
ClassyFire Subclass: Indoles
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Aspidosperma type
Synonymous chemical names:
voaphylline-hydroxyindolenine, Voaphylline hydroxyindolenine, voaphylline hydroxyindolenine
External chemical identifiers:
CID:CID_13783711
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Voaphylline hydroxyindolenine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 312.41
Log P RDKit 2.62
Topological polar surface area (Å2) RDKit 48.36
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
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 4
Stereochemical complexity RDKit 0.21
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.63
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 3
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
Voaphylline hydroxyindolenine
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 0.811051
Voaphylline hydroxyindolenine
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 -7.06
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