IMPPAT Phytochemical information: 
Vinpocetine

Vinpocetine
Summary

SMILES: CCOC(=O)C1=C[C@]2(CC)CCCN3[C@@H]2c2n1c1ccccc1c2CC3
InChI: InChI=1S/C22H26N2O2/c1-3-22-11-7-12-23-13-10-16-15-8-5-6-9-17(15)24(19(16)20(22)23)18(14-22)21(25)26-4-2/h5-6,8-9,14,20H,3-4,7,10-13H2,1-2H3/t20-,22+/m1/s1
InChIKey: DDNCQMVWWZOMLN-IRLDBZIGSA-N
DeepSMILES: CCOC=O)C=C[C@]CC))CCCN[C@@H]6cn%10cccccc6c9CC%13
Scaffold Graph/Node/Bond level: C1=Cn2c3c(c4ccccc42)CCN2CCCC1C32
Scaffold Graph/Node level: C1CCC2C(C1)C1CCN3CCCC4CCN2C1C43
Scaffold Graph level: C1CC2CCC3C4CCCCC4C4CCC(C1)C2C34
Functional groups: cn(c)C(C(=O)OC)=CC; CN(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Eburnan-type alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Aspidosperma type
Synonymous chemical names:
vinpocetine
External chemical identifiers:
CID:CID_443955; ChEMBL:CHEMBL71752; ChEBI:CHEBI:32297; ZINC:ZINC000019796031; FDASRS:543512OBTC; SureChEMBL:SCHEMBL50081; MolPort-003-666-450
Chemical structure download


Vinpocetine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 350.46
Log P RDKit 4.15
Topological polar surface area (Å2) RDKit 34.47
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.09
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 11
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.5
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 5
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 5


Vinpocetine
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 Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.78016


Vinpocetine
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 -5.51
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No


Vinpocetine
Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000379496PDE1C888
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.