IMPPAT Phytochemical information: 
Tabernamine
Tabernamine
Summary

SMILES: CC[C@H]1C[C@@H]2CN3[C@@H]1[C@@H](C2)c1[nH]c2c(c1CC3)ccc(c2)[C@H]1C[C@H]2/C(=C\C)/CN([C@@H](C2C(=O)OC)Cc2c1[nH]c1c2cccc1)C
InChI: InChI=1S/C40H48N4O2/c1-5-23-15-22-16-32-37-28(13-14-44(20-22)39(23)32)27-12-11-25(17-34(27)42-37)30-18-29-24(6-2)21-43(3)35(36(29)40(45)46-4)19-31-26-9-7-8-10-33(26)41-38(30)31/h6-12,17,22-23,29-30,32,35-36,39,41-42H,5,13-16,18-21H2,1-4H3/b24-6-/t22-,23-,29-,30+,32-,35+,36?,39-/m0/s1
InChIKey: MTARGWPMLJBYNG-SESIEVFNSA-N
DeepSMILES: CC[C@H]C[C@@H]CN[C@@H]6[C@@H]C6)c[nH]ccc5CC%10)))cccc6)[C@H]C[C@H]/C=C\C))/CN[C@@H]C6C=O)OC))))Ccc%10[nH]cc5cccc6)))))))))))C
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[nH]c; C/C=C(/C)C
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:
tabernamine
External chemical identifiers:
CID:CID_11953930
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Tabernamine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 616.85
Log P RDKit 7.15
Topological polar surface area (Å2) RDKit 64.36
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 40
Number of heavy atoms RDKit 46
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 4
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 8
Stereochemical complexity RDKit 0.2
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 19
Number of sp3 hybridized carbon atoms RDKit 21
Shape complexity RDKit 0.53
Number of rotatable bonds RDKit 4
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
Tabernamine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 4
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.189573
Tabernamine
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