IMPPAT Phytochemical information: 
Verticillatine (Rauwolfia)
Verticillatine (Rauwolfia)
Summary

SMILES: OC1OCC2C3C1C1Cc4c(C(C3)[N+]1(C2C)C)[nH]c1c4cc(O)cc1
InChI: InChI=1S/C20H24N2O3/c1-9-14-8-25-20(24)18-12(14)6-17-19-13(7-16(18)22(9,17)2)11-5-10(23)3-4-15(11)21-19/h3-5,9,12,14,16-18,20-21,24H,6-8H2,1-2H3/p+1
InChIKey: FJKICKPAGXMAIN-UHFFFAOYSA-O
DeepSMILES: OCOCCCC6CCccCC8)[N+]6C%10C))C)))[nH]cc5ccO)cc6
Scaffold Graph/Node/Bond level: c1ccc2c3c([nH]c2c1)C1CC2C4COCC2C(C3)[NH+]1C4
Scaffold Graph/Node level: C1CCC2C(C1)NC1C2CC2C3COCC4CN2C1CC43
Scaffold Graph level: C1CCC2C(C1)CC1C2CC2C3CCCC4CC2C1CC43
Functional groups: COC(C)O; C[N+](C)(C)C; cO; c[nH]c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Macroline alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Corynanthe type
Synonymous chemical names:
verticillatine
External chemical identifiers:
CID:176717
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Verticillatine (Rauwolfia)
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 0
Log P RDKit 0
Topological polar surface area (Å2) RDKit
Number of hydrogen bond acceptors RDKit
Number of hydrogen bond donors RDKit
Number of carbon atoms RDKit
Number of heavy atoms RDKit
Number of heteroatoms RDKit
Number of nitrogen atoms RDKit
Number of sulfur atoms RDKit
Number of chiral carbon atoms RDKit
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit
Number of sp2 hybridized carbon atoms RDKit
Number of sp3 hybridized carbon atoms RDKit
Shape complexity RDKit
Number of rotatable bonds RDKit
Number of aliphatic carbocycles RDKit
Number of aliphatic heterocycles RDKit
Number of aliphatic rings RDKit
Number of aromatic carbocycles RDKit
Number of aromatic heterocycles RDKit
Number of aromatic rings RDKit
Total number of rings RDKit
Number of saturated carbocycles RDKit
Number of saturated heterocycles RDKit
Number of saturated rings RDKit
Number of Smallest Set of Smallest Rings (SSSR) RDKit
Verticillatine (Rauwolfia)
Drug-likeness
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 0.6443
Verticillatine (Rauwolfia)
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.01
Number of PAINS structural alerts SwissADME 1.0
Number of Brenk structural alerts SwissADME 1.0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes
Verticillatine (Rauwolfia)
Phytochemical - Predicted human target protein associations
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000280155ADRA2A800
ENSP00000306662ADRA1B800
ENSP00000368766ADRA1D800
ENSP00000369960ADRA1A800
ENSP00000386069ADRA2C800
ENSP00000387281ADRA2B800
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.