IMPPAT Phytochemical information: 
Vindolinine, hydrochloride

Vindolinine, hydrochloride
Summary

SMILES: COC(=O)C1CC23C=CCN4C3C3(C1Nc1c3cccc1)C(C2C)C4.Cl
InChI: InChI=1S/C21H24N2O2.ClH/c1-12-15-11-23-9-5-8-20(12)10-13(18(24)25-2)17-21(15,19(20)23)14-6-3-4-7-16(14)22-17;/h3-8,12-13,15,17,19,22H,9-11H2,1-2H3;1H
InChIKey: NLXUZHWMDFTHOU-UHFFFAOYSA-N
DeepSMILES: COC=O)CCCC=CCNC6CC%10Ncc5cccc6))))))))CC9C))C5.Cl
Scaffold Graph/Node/Bond level: C1=CC23CCC4Nc5ccccc5C45C(CN(C1)C25)C3
Scaffold Graph/Node level: C1CCC2C(C1)NC1CCC34CCCN5CC(C3)C12C54
Scaffold Graph level: C1CCC2C(C1)CC1CCC34CCCC5CC(C3)C12C54
Functional groups: COC(C)=O; CC=CC; CN(C)C; cNC; Cl
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Indoles and derivatives
ClassyFire Subclass: Carbazoles
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Aspidosperma type
Synonymous chemical names:
vindolinine hydrochloride
External chemical identifiers:
CID:CID_24190768; ChEMBL:CHEMBL1980833
Chemical structure download


Vindolinine, hydrochloride
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 372.9
Log P RDKit 2.84
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 26
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 0.33
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.57
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 2
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6


Vindolinine, hydrochloride
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 0.607685


Vindolinine, hydrochloride
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.88
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 Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes