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(O)C; C[N+](C)(C)C; c[nH]c; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Macroline alkaloids
Synonymous chemical names:
verticillatine
External chemical identifiers:
CID:CID_176717
Chemical structure download


Verticillatine (Rauwolfia)
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 341.43
Log P RDKit 2.29
Topological polar surface area (Å2) RDKit 65.48
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 7
Stereochemical complexity RDKit 0.35
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.6
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 5
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 7
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 4
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 7


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 0.644316


Verticillatine (Rauwolfia)
ADME 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
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 Yes