IMPPAT Phytochemical information: 
Voacangine

Voacangine
Summary

SMILES: CC[C@H]1C[C@@H]2CN3[C@@H]1[C@](C2)(C(=O)OC)c1[nH]c2c(c1CC3)cc(cc2)OC
InChI: InChI=1S/C22H28N2O3/c1-4-14-9-13-11-22(21(25)27-3)19-16(7-8-24(12-13)20(14)22)17-10-15(26-2)5-6-18(17)23-19/h5-6,10,13-14,20,23H,4,7-9,11-12H2,1-3H3/t13-,14-,20-,22+/m0/s1
InChIKey: MMAYTCMMKJYIAM-RUGRQLENSA-N
DeepSMILES: CC[C@H]C[C@@H]CN[C@@H]6[C@]C6)C=O)OC)))c[nH]ccc5CC%10)))cccc6))OC
Scaffold Graph/Node/Bond level: c1ccc2c3c([nH]c2c1)C1CC2CCC1N(CC3)C2
Scaffold Graph/Node level: C1CCC2C(C1)NC1C2CCN2CC3CCC2C1C3
Scaffold Graph level: C1CCC2C(C1)CC1C2CCC2CC3CCC2C1C3
Functional groups: CN(C)C; COC(C)=O; c[nH]c; cOC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Ibogan-type alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Iboga type
Synonymous chemical names:
voacangine
External chemical identifiers:
CID:CID_73255; ChEMBL:CHEMBL182120; ChEBI:CHEBI:141966; ZINC:ZINC000100392804
Chemical structure download


Voacangine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 368.48
Log P RDKit 3.26
Topological polar surface area (Å2) RDKit 54.56
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.18
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.59
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6


Voacangine
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 0.84517


Voacangine
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


Voacangine
Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000303211ACHE818
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.