IMPPAT Phytochemical information: 
Villalstonine

Villalstonine
Summary

SMILES: COC(=O)C1C2CC3C45N1c1ccccc1C5(CCN3C/C/2=C\C)CC1C(O4)(C)OCC2C1CC1N(C2Cc2c1n(C)c1c2cccc1)C
InChI: InChI=1S/C41H48N4O4/c1-6-23-21-44-16-15-40-20-30-26-17-34-36-27(24-11-7-9-13-31(24)43(36)4)18-33(42(34)3)28(26)22-48-39(30,2)49-41(40)35(44)19-25(23)37(38(46)47-5)45(41)32-14-10-8-12-29(32)40/h6-14,25-26,28,30,33-35,37H,15-22H2,1-5H3/b23-6+
InChIKey: XXNYZYBYNFRERU-TXNBCWFRSA-N
DeepSMILES: COC=O)CCCCCN6cccccc6C9CCN%13C/C/%17=C\C)))))))CCCO%13)C)OCCC6CCNC6Ccc6nC)cc5cccc6)))))))))))C
Scaffold Graph/Node/Bond level: C=C1CN2CCC34CC5C(OCC6C7Cc8c([nH]c9ccccc89)C(CC65)N7)OC35C2CC1CN5c1ccccc14
Scaffold Graph/Node level: CC1CN2CCC34CC5C(OCC6C7CC8C9CCCCC9NC8C(CC65)N7)OC35C2CC1CN5C1CCCCC14
Scaffold Graph level: CC1CC2CCC34CC5C(CCC6C7CC(CC65)C5CC6CCCCC6C5C7)CC35C2CC1CC5C1CCCCC14
Functional groups: COC(C)=O; CN(C)C; cn(C)c; cN(C)C(C)(C)OC(C)(C)OC; C/C=C(/C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Pleiocarpaman alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Corynanthe type
Synonymous chemical names:
villalstonine
External chemical identifiers:
CID:CID_5476353
Chemical structure download


Villalstonine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 660.86
Log P RDKit 5.54
Topological polar surface area (Å2) RDKit 59.41
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 41
Number of heavy atoms RDKit 49
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 4
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 11
Stereochemical complexity RDKit 0.27
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 17
Number of sp3 hybridized carbon atoms RDKit 24
Shape complexity RDKit 0.59
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 8
Number of aliphatic rings RDKit 8
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 11
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 6
Number of saturated rings RDKit 6
Number of Smallest Set of Smallest Rings (SSSR) RDKit 11


Villalstonine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 3
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.25


Villalstonine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.67
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 No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes