IMPPAT Phytochemical information: 
Vincarodine

Vincarodine
Summary

SMILES: COC(=O)C12OC3C(C1)(CC)C1c4n2c2cc(OC)ccc2c4CCN1CC3O
InChI: InChI=1S/C22H26N2O5/c1-4-21-11-22(20(26)28-3)24-15-9-12(27-2)5-6-13(15)14-7-8-23(18(21)17(14)24)10-16(25)19(21)29-22/h5-6,9,16,18-19,25H,4,7-8,10-11H2,1-3H3
InChIKey: DFVNOPYNGMIZGL-UHFFFAOYSA-N
DeepSMILES: COC=O)COCCC5)CC))Ccn7cccOC))ccc6c9CCN%13CC%17O
Scaffold Graph/Node/Bond level: c1ccc2c(c1)c1c3n2C2CC4C(CCN(CC1)C34)O2
Scaffold Graph/Node level: C1CCC2C(C1)C1CCN3CCC4OC5CC4C3C1N52
Scaffold Graph level: C1CCC2C(C1)C1CCC3CCC4CC5CC4C3C1C52
Functional groups: COC(C)=O; COC; cn(c)C; cOC; CN(C)C; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Indolonaphthyridine alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Iboga type
Synonymous chemical names:
Vincarodine, vincarodine
External chemical identifiers:
CID:CID_298042
Chemical structure download


Vincarodine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 398.46
Log P RDKit 1.95
Topological polar surface area (Å2) RDKit 73.16
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 29
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.23
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.59
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6


Vincarodine
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 0.797117


Vincarodine
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 No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.40
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
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