IMPPAT Phytochemical information: 
Glucofrugoside
Glucofrugoside
Summary

SMILES: OC[C@@H]1O[C@H](O[C@H]2[C@H](C)O[C@@H]([C@H]([C@H]2O)O)O[C@@H]2CC[C@@]3([C@@H](C2)CC[C@H]2C3CC[C@@]3([C@@]2(O)CC[C@H]3C2=CC(=O)OC2)C)CO)[C@H]([C@@H]([C@H]1O)O)O
InChI: InChI=1S/C35H54O14/c1-16-30(49-32-28(42)26(40)25(39)23(13-36)48-32)27(41)29(43)31(46-16)47-19-5-9-34(15-37)18(12-19)3-4-22-21(34)6-8-33(2)20(7-10-35(22,33)44)17-11-24(38)45-14-17/h11,16,18-23,25-32,36-37,39-44H,3-10,12-15H2,1-2H3/t16-,18+,19+,20-,21?,22-,23-,25-,26+,27+,28-,29-,30-,31+,32+,33-,34-,35+/m0/s1
InChIKey: OFSZOCPGPLMCBG-YPZPFACESA-N
DeepSMILES: OC[C@@H]O[C@H]O[C@H][C@H]C)O[C@@H][C@H][C@H]6O))O))O[C@@H]CC[C@@][C@@H]C6)CC[C@H]C6CC[C@@][C@@]6O)CC[C@H]5C=CC=O)OC5)))))))))C)))))))))CO))))))))))))[C@H][C@@H][C@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C1C=C(C2CCC3C2CCC2C4CCC(OC5CCC(OC6CCCCO6)CO5)CC4CCC23)CO1
Scaffold Graph/Node level: OC1CC(C2CCC3C2CCC2C4CCC(OC5CCC(OC6CCCCO6)CO5)CC4CCC23)CO1
Scaffold Graph level: CC1CCC(C2CCC3C2CCC2C4CCC(CC5CCC(CC6CCCCC6)CC5)CC4CCC23)C1
Functional groups: CO; CO[C@H](C)OC; CC1=CC(=O)OC1
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: Cardenolides
Synonymous chemical names:
glucofrugoside (cardenolide)
External chemical identifiers:
CID:CID_133556251
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Glucofrugoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 698.8
Log P RDKit -0.75
Topological polar surface area (Å2) RDKit 225.06
Number of hydrogen bond acceptors RDKit 14
Number of hydrogen bond donors RDKit 8
Number of carbon atoms RDKit 35
Number of heavy atoms RDKit 49
Number of heteroatoms RDKit 14
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 18
Stereochemical complexity RDKit 0.51
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 3
Number of sp3 hybridized carbon atoms RDKit 32
Shape complexity RDKit 0.91
Number of rotatable bonds RDKit 7
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 4
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 6
Number of Smallest Set of Smallest Rings (SSSR) RDKit 7
Glucofrugoside
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 4
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
Glucofrugoside
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 -11.07
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 No