IMPPAT Phytochemical information: 
Tabersonine

Tabersonine
Summary

SMILES: COC(=O)C1=C2Nc3c([C@@]42[C@@H]2[C@@](C1)(CC)C=CCN2CC4)cccc3
InChI: InChI=1S/C21H24N2O2/c1-3-20-9-6-11-23-12-10-21(19(20)23)15-7-4-5-8-16(15)22-17(21)14(13-20)18(24)25-2/h4-9,19,22H,3,10-13H2,1-2H3/t19-,20-,21-/m0/s1
InChIKey: FNGGIPWAZSFKCN-ACRUOGEOSA-N
DeepSMILES: COC=O)C=CNcc[C@]5[C@@H][C@@]C9)CC))C=CCN6CC9)))))))))cccc6
Scaffold Graph/Node/Bond level: C1=CC2CC=C3Nc4ccccc4C34CCN(C1)C24
Scaffold Graph/Node level: C1CCC2C(C1)NC1CCC3CCCN4CCC12C34
Scaffold Graph level: C1CCC2C(C1)CC1CCC3CCCC4CCC12C34
Functional groups: cNC(=C(C(=O)OC)C)C; CC=CC; CN(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Plumeran-type alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Aspidosperma type
Synonymous chemical names:
tabersonine, Tabersonine
External chemical identifiers:
CID:CID_20485; ChEMBL:CHEMBL2011511; ChEBI:CHEBI:16776; ZINC:ZINC000056871302; SureChEMBL:SCHEMBL829379; MolPort-020-005-961
Chemical structure download


Tabersonine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 336.44
Log P RDKit 3.22
Topological polar surface area (Å2) RDKit 41.57
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.14
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 11
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.48
Number of rotatable bonds RDKit 3
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 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5


Tabersonine
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 0.67


Tabersonine
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 -5.96
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes