IMPPAT Phytochemical information: 
Vindolinine
Vindolinine
Summary

SMILES: COC(=O)[C@@H]1C[C@]23[C@H]([C@]41Nc1c([C@@]54[C@H]3N(CC5)CC=C2)cccc1)C
InChI: InChI=1S/C21H24N2O2/c1-13-19-8-5-10-23-11-9-20(18(19)23)14-6-3-4-7-16(14)22-21(13,20)15(12-19)17(24)25-2/h3-8,13,15,18,22H,9-12H2,1-2H3/t13-,15+,18+,19+,20-,21-/m1/s1
InChIKey: JSLDLCGKZDUQSH-SBDPWIONSA-N
DeepSMILES: COC=O)[C@@H]C[C@@][C@H][C@@]5Ncc[C@]5[C@H]8NCC5))CC=C%12))))))cccc6))))))))C
Scaffold Graph/Node/Bond level: C1=CC23CCC4(C2)Nc2ccccc2C42CCN(C1)C32
Scaffold Graph/Node level: C1CCC2C(C1)NC13CCC4(CCCN5CCC21C54)C3
Scaffold Graph level: C1CCC2C(C1)CC13CCC4(CCCC5CCC21C54)C3
Functional groups: COC(C)=O; cNC; CN(C)C; CC=CC
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
External chemical identifiers:
CID:CID_24148538; ChEMBL:CHEMBL1165590; ChEBI:CHEBI:141964; ZINC:ZINC000003114722
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Vindolinine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 336.44
Log P RDKit 2.56
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 6
Stereochemical complexity RDKit 0.29
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
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 0.632131
Vindolinine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME 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 -6.29
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 No