IMPPAT Phytochemical information: 
Voaphylline

Voaphylline
Summary

SMILES: CC[C@]12CCc3[nH]c4c(c3CCN(C1)C[C@@H]1[C@H]2O1)cccc4
InChI: InChI=1S/C19H24N2O/c1-2-19-9-7-16-14(13-5-3-4-6-15(13)20-16)8-10-21(12-19)11-17-18(19)22-17/h3-6,17-18,20H,2,7-12H2,1H3/t17-,18-,19+/m1/s1
InChIKey: OGDFTQDRHAGLTB-QRVBRYPASA-N
DeepSMILES: CC[C@]CCc[nH]ccc5CCNC%12)C[C@@H][C@H]%14O3))))))))cccc6
Scaffold Graph/Node/Bond level: c1ccc2c3c([nH]c2c1)CCC1CN(CC3)CC2OC12
Scaffold Graph/Node level: C1CCC2C(C1)NC1CCC3CN(CCC12)CC1OC31
Scaffold Graph level: C1CCC2C(C1)CC1CCC3CC(CCC12)CC1CC31
Functional groups: c[nH]c; CN(C)C; C[C@H]1O[C@H]1C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Quebrachamine alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Iboga type
Synonymous chemical names:
voaphylline, Voaphylline
External chemical identifiers:
CID:CID_10469868; SureChEMBL:SCHEMBL6240642
Chemical structure download


Voaphylline
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 296.41
Log P RDKit 3.14
Topological polar surface area (Å2) RDKit 31.56
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 22
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.16
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.58
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5


Voaphylline
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.82


Voaphylline
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately 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 -5.75
Number of PAINS structural alerts SwissADME 1
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