IMPPAT Phytochemical information: 
Withanoside VI
Withanoside VI
Summary

SMILES: OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](O[C@H]3C[C@H](O)[C@]4(C(=CC[C@@H]5[C@@H]4CC[C@]4([C@H]5CC[C@@H]4[C@]([C@H]4CC(=C(C(=O)O4)C)C)(O)C)C)C3)C)[C@@H]([C@H]([C@@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C40H62O15/c1-17-12-28(55-35(49)18(17)2)40(5,50)26-9-8-22-21-7-6-19-13-20(14-27(42)39(19,4)23(21)10-11-38(22,26)3)52-37-34(48)32(46)30(44)25(54-37)16-51-36-33(47)31(45)29(43)24(15-41)53-36/h6,20-34,36-37,41-48,50H,7-16H2,1-5H3/t20-,21+,22+,23+,24-,25-,26+,27+,28-,29-,30-,31+,32+,33-,34-,36-,37-,38+,39+,40-/m1/s1
InChIKey: MKCYAASFWFGIJK-BWBMWEGTSA-N
DeepSMILES: OC[C@H]O[C@@H]OC[C@H]O[C@@H]O[C@H]C[C@H]O)[C@]C=CC[C@@H][C@@H]6CC[C@][C@H]6CC[C@@H]5[C@][C@H]CC=CC=O)O6))C))C))))O)C))))))C))))))))C6))C))))))[C@@H][C@H][C@@H]6O))O))O)))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C1C=CCC(CC2CCC3C2CCC2C4CCC(OC5CCCC(COC6CCCCO6)O5)CC4=CCC23)O1
Scaffold Graph/Node level: OC1CCCC(CC2CCC3C2CCC2C4CCC(OC5CCCC(COC6CCCCO6)O5)CC4CCC32)O1
Scaffold Graph level: CC1CCCC(CC2CCC3C2CCC2C4CCC(CC5CCCC(CCC6CCCCC6)C5)CC4CCC32)C1
Functional groups: CO; CO[C@@H](C)OC; CC=C(C)C; CC1=C(C)C(=O)OCC1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Steroids and steroid derivatives
ClassyFire Subclass: Steroid lactones
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Steroids
NP Classifier Class: Ergostane steroids
Synonymous chemical names:
withanoside vi
External chemical identifiers:
CID:CID_91827019; ZINC:ZINC000255234858; FDASRS:25Q6Y8Y108; SureChEMBL:SCHEMBL16365857
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Withanoside VI
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 782.92
Log P RDKit -0.05
Topological polar surface area (Å2) RDKit 245.29
Number of hydrogen bond acceptors RDKit 15
Number of hydrogen bond donors RDKit 9
Number of carbon atoms RDKit 40
Number of heavy atoms RDKit 55
Number of heteroatoms RDKit 15
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 20
Stereochemical complexity RDKit 0.5
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 35
Shape complexity RDKit 0.88
Number of rotatable bonds RDKit 8
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 7
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 7
Number of saturated carbocycles RDKit 3
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 5
Number of Smallest Set of Smallest Rings (SSSR) RDKit 7
Withanoside VI
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 3
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.12
Withanoside VI
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -10.88
Number of PAINS structural alerts SwissADME 0
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