IMPPAT Phytochemical information: 
Simplexoside
Simplexoside
Summary

SMILES: OC[C@H]1O[C@@H](Oc2ccc(cc2OC)[C@H]2OC[C@H]3[C@@H]2CO[C@@H]3c2ccc3c(c2)OCO3)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C26H30O11/c1-31-18-6-12(3-5-17(18)36-26-23(30)22(29)21(28)20(8-27)37-26)24-14-9-33-25(15(14)10-32-24)13-2-4-16-19(7-13)35-11-34-16/h2-7,14-15,20-30H,8-11H2,1H3/t14-,15-,20+,21+,22-,23+,24+,25+,26+/m0/s1
InChIKey: USVLFVSHBLNSOC-WMYFGKAISA-N
DeepSMILES: OC[C@H]O[C@@H]Occcccc6OC))))[C@H]OC[C@H][C@@H]5CO[C@@H]5cccccc6)OCO5)))))))))))))))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: c1cc(C2OCC3C(c4ccc5c(c4)OCO5)OCC23)ccc1OC1CCCCO1
Scaffold Graph/Node level: C1CCC(OC2CCC(C3OCC4C3COC4C3CCC4OCOC4C3)CC2)OC1
Scaffold Graph level: C1CCC(CC2CCC(C3CCC4C(C5CCC6CCCC6C5)CCC34)CC2)CC1
Functional groups: CO; cO[C@@H](C)OC; cOC; COC; c1cOCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lignans, neolignans and related compounds
ClassyFire Class: Lignan glycosides
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Lignans
NP Classifier Class: Furofuranoid lignans
Synonymous chemical names:
Simplexoside, simplexoside
External chemical identifiers:
CID:CID_443020; ChEMBL:CHEMBL2442734; ChEBI:CHEBI:9149; ZINC:ZINC000004098930
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Simplexoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 518.52
Log P RDKit 0.68
Topological polar surface area (Å2) RDKit 145.53
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 26
Number of heavy atoms RDKit 37
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.35
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 14
Shape complexity RDKit 0.54
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 3
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6
Simplexoside
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 1
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.428252
Simplexoside
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -8.98
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 Yes