IMPPAT Phytochemical information: 
Vinburnine

Vinburnine
Summary

SMILES: CC[C@]12CCCN3[C@@H]2c2n(C(=O)C1)c1c(c2CC3)cccc1
InChI: InChI=1S/C19H22N2O/c1-2-19-9-5-10-20-11-8-14-13-6-3-4-7-15(13)21(16(22)12-19)17(14)18(19)20/h3-4,6-7,18H,2,5,8-12H2,1H3/t18-,19+/m1/s1
InChIKey: WYJAPUKIYAZSEM-MOPGFXCFSA-N
DeepSMILES: CC[C@@]CCCN[C@@H]6cnC=O)C%10))ccc5CC9)))cccc6
Scaffold Graph/Node/Bond level: O=C1CC2CCCN3CCc4c(n1c1ccccc41)C23
Scaffold Graph/Node level: OC1CC2CCCN3CCC4C5CCCCC5N1C4C23
Scaffold Graph level: CC1CC2CCCC3CCC4C5CCCCC5C1C4C32
Functional groups: cn(c)C(=O)C; 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:
eburnamonine, vinburnine
External chemical identifiers:
CID:CID_71203; ChEMBL:CHEMBL1892145; ChEBI:CHEBI:4740; ZINC:ZINC000019796061; FDASRS:64UB2942IE; SureChEMBL:SCHEMBL456385; MolPort-001-742-589
Chemical structure download


Vinburnine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 294.4
Log P RDKit 3.77
Topological polar surface area (Å2) RDKit 25.24
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 22
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.11
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.53
Number of rotatable bonds RDKit 1
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


Vinburnine
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 0.799584


Vinburnine
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 -5.94
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 No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes