IMPPAT Phytochemical information: 
Virescenine

Virescenine
Summary

SMILES: COC[C@]12CC[C@@H]([C@@]34[C@@H]2C[C@]([C@H]3N(C1)CC)(O)[C@@]1([C@@H]2[C@H]4C[C@@H]([C@@H]2O)[C@H](C1)OC)O)O
InChI: InChI=1S/C23H37NO6/c1-4-24-10-20(11-29-2)6-5-16(25)23-13-7-12-14(30-3)8-21(27,17(13)18(12)26)22(28,19(23)24)9-15(20)23/h12-19,25-28H,4-11H2,1-3H3/t12-,13-,14+,15-,16+,17-,18+,19-,20+,21-,22-,23-/m1/s1
InChIKey: KLZURCUGZWEIAU-KJJIZPFLSA-N
DeepSMILES: COC[C@@]CC[C@@H][C@@][C@@H]6C[C@][C@H]5NC%11)CC))))O)[C@@][C@@H][C@H]7C[C@@H][C@@H]5O))[C@H]C7)OC)))))))O))))))O
Scaffold Graph/Node/Bond level: C1CC2CNC3C4CC2C3(C1)C1CC2CCC4C1C2
Scaffold Graph/Node level: C1CC2CNC3C4CC2C3(C1)C1CC2CCC4C1C2
Scaffold Graph level: C1CC2CCC3C4CC2C3(C1)C1CC2CCC4C1C2
Functional groups: COC; CN(C)C; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Diterpenoids
NP Classifier Biosynthetic pathway: Alkaloids|Terpenoids
NP Classifier Superclass: Pseudoalkaloids
NP Classifier Class: Terpenoid alkaloids
Synonymous chemical names:
virescenine
External chemical identifiers:
CID:CID_100964235; ZINC:ZINC000255222886
Chemical structure download


Virescenine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 423.55
Log P RDKit -0.01
Topological polar surface area (Å2) RDKit 102.62
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 23
Number of heavy atoms RDKit 30
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 12
Stereochemical complexity RDKit 0.52
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 0
Number of sp3 hybridized carbon atoms RDKit 23
Shape complexity RDKit 1
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 5
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 6
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 5
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 6
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6


Virescenine
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 Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.504494


Virescenine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -9.37
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 No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes