IMPPAT Phytochemical information: 
Vincamajoreine
Vincamajoreine
Summary

SMILES: C/C=C\1/CN2[C@@H]3C4[C@H]1C[C@H]2[C@H]1[C@@]([C@@H]4O)(C3)c2c(N1C)ccc(c2)OC
InChI: InChI=1S/C21H26N2O2/c1-4-11-10-23-16-8-13(11)18-17(23)9-21(20(18)24)14-7-12(25-3)5-6-15(14)22(2)19(16)21/h4-7,13,16-20,24H,8-10H2,1-3H3/b11-4-/t13-,16-,17-,18?,19-,20+,21+/m0/s1
InChIKey: QFJCZEAKZSDBCK-FODOJFLHSA-N
DeepSMILES: C/C=C/CN[C@@H]C[C@H]/6C[C@H]6[C@H][C@@][C@@H]7O))C8)ccN5C))cccc6)OC
Scaffold Graph/Node/Bond level: C=C1CN2C3CC45CC3C1CC2C4Nc1ccccc15
Scaffold Graph/Node level: CC1CN2C3CC45CC3C1CC2C4NC1CCCCC15
Scaffold Graph level: CC1CC2C3CC45CC3C1CC2C4CC1CCCCC15
Functional groups: C/C=C(/C)C; CN(C)C; CO; cN(C)C; cOC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Ajmaline-sarpagine alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Corynanthe type
Synonymous chemical names:
vincamajoreine
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Vincamajoreine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 338.45
Log P RDKit 2.16
Topological polar surface area (Å2) RDKit 35.94
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 7
Stereochemical complexity RDKit 0.33
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.62
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 5
Number of aliphatic rings RDKit 6
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 7
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 4
Number of saturated rings RDKit 5
Number of Smallest Set of Smallest Rings (SSSR) RDKit 7
Vincamajoreine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.8
Vincamajoreine
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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.88
Number of PAINS structural alerts SwissADME 1
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