IMPPAT Phytochemical information: 
Tabernaemontanine
Tabernaemontanine
Summary

SMILES: CC[C@@H]1CN(C)[C@@H]2[C@H]([C@H]1CC(=O)c1c(C2)c2c([nH]1)cccc2)C(=O)OC
InChI: InChI=1S/C21H26N2O3/c1-4-12-11-23(2)17-9-15-13-7-5-6-8-16(13)22-20(15)18(24)10-14(12)19(17)21(25)26-3/h5-8,12,14,17,19,22H,4,9-11H2,1-3H3/t12-,14+,17+,19+/m1/s1
InChIKey: FFVRRQMGGGTQRH-DTPILHQWSA-N
DeepSMILES: CC[C@@H]CNC)[C@@H][C@H][C@H]6CC=O)ccC8)cc[nH]5)cccc6)))))))))))C=O)OC
Scaffold Graph/Node/Bond level: O=C1CC2CCNC(Cc3c1[nH]c1ccccc31)C2
Scaffold Graph/Node level: OC1CC2CCNC(C2)CC2C3CCCCC3NC12
Scaffold Graph level: CC1CC2CCCC(C2)CC2C1CC1CCCCC12
Functional groups: CN(C)C; cC(=O)C; c[nH]c; COC(C)=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Vobasan alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Corynanthe type
Synonymous chemical names:
Tabernaemontanine, tabernaemontanine, tabernaemontanin
External chemical identifiers:
CID:CID_12309360; ChEBI:CHEBI:142075
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Tabernaemontanine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 354.45
Log P RDKit 3.04
Topological polar surface area (Å2) RDKit 62.4
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 26
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 0.19
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 10
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.52
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 4
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 4
Tabernaemontanine
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 0.842255
Tabernaemontanine
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 -6.14
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes