IMPPAT Phytochemical information: 
Voacamine
Voacamine
Summary

SMILES: COC(=O)C1[C@H]2C[C@H](c3cc4[nH]c5c(c4cc3OC)CCN3[C@@H]4[C@]5(C[C@H](C[C@@H]4CC)C3)C(=O)OC)c3c(C[C@H]1N(C/C/2=C/C)C)c1ccccc1[nH]3
InChI: InChI=1S/C43H52N4O5/c1-7-24-15-23-20-43(42(49)52-6)39-27(13-14-47(21-23)40(24)43)29-19-36(50-4)30(17-34(29)45-39)31-16-28-25(8-2)22-46(3)35(37(28)41(48)51-5)18-32-26-11-9-10-12-33(26)44-38(31)32/h8-12,17,19,23-24,28,31,35,37,40,44-45H,7,13-16,18,20-22H2,1-6H3/b25-8-/t23-,24-,28-,31+,35+,37?,40-,43+/m0/s1
InChIKey: VCMIRXRRQJNZJT-XRMSBCOFSA-N
DeepSMILES: COC=O)C[C@H]C[C@H]ccc[nH]ccc5cc9OC)))))CCN[C@@H][C@]7C[C@H]C[C@@H]6CC))))C6)))C=O)OC))))))))))))))ccC[C@H]8NC/C/%10=C/C))))C))))cccccc6[nH]9
Scaffold Graph/Node/Bond level: C=C1CNC2Cc3c([nH]c4ccccc34)C(c3ccc4c5c([nH]c4c3)C3CC4CCC3N(CC5)C4)CC1C2
Scaffold Graph/Node level: CC1CNC2CC1CC(C1CCC3C(C1)NC1C3CCN3CC4CCC3C1C4)C1NC3CCCCC3C1C2
Scaffold Graph level: CC1CCC2CC1CC(C1CCC3C(C1)CC1C3CCC3CC4CCC3C1C4)C1CC3CCCCC3C1C2
Functional groups: COC(C)=O; CN(C)C; C/C=C(/C)C; 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:
Voacamine, voacamine
External chemical identifiers:
CID:CID_11953931
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Voacamine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 704.91
Log P RDKit 6.49
Topological polar surface area (Å2) RDKit 99.89
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 43
Number of heavy atoms RDKit 52
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 4
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 8
Stereochemical complexity RDKit 0.19
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 20
Number of sp3 hybridized carbon atoms RDKit 23
Shape complexity RDKit 0.53
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 6
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 2
Number of aromatic rings RDKit 4
Total number of rings RDKit 10
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 10
Voacamine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 4
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.18
Voacamine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.45
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 No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No
Voacamine
Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000265724ABCB1815
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.