IMPPAT Phytochemical information: 
Rotundioside F
Rotundioside F
Summary

SMILES: OC[C@H]1O[C@@H](O[C@H]2[C@@H](O[C@@H]([C@@H]([C@@H]2O)O)C)O[C@H]2CC[C@]3([C@H](C2(C)C)CC[C@@]2([C@@H]3C=C[C@]34[C@@]2(C)C[C@H]([C@@]2([C@H]4CC(C)(C)CC2)CO3)O)C)C)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O
InChI: InChI=1S/C48H78O16/c1-22-30(51)33(54)36(57)39(59-22)63-38-35(56)32(53)24(20-49)61-41(38)64-37-34(55)31(52)23(2)60-40(37)62-29-12-13-44(7)25(43(29,5)6)10-14-45(8)26(44)11-15-48-27-18-42(3,4)16-17-47(27,21-58-48)28(50)19-46(45,48)9/h11,15,22-41,49-57H,10,12-14,16-21H2,1-9H3/t22-,23+,24+,25-,26+,27+,28+,29-,30-,31-,32+,33+,34-,35-,36+,37+,38+,39-,40-,41-,44-,45+,46-,47+,48-/m0/s1
InChIKey: HMEMJYQIFNQSFR-DQKATWECSA-N
DeepSMILES: OC[C@H]O[C@@H]O[C@H][C@@H]O[C@@H][C@@H][C@@H]6O))O))C)))O[C@H]CC[C@][C@H]C6C)C))CC[C@@][C@@H]6C=C[C@@][C@@]6C)C[C@H][C@@][C@H]6CCC)C)CC6)))))CO7)))O))))))))C)))))C)))))))))[C@@H][C@H][C@@H]6O))O))O[C@@H]O[C@@H]C)[C@@H][C@H][C@H]6O))O))O
Scaffold Graph/Node/Bond level: C1=CC23OCC4(CCCCC42)CCC3C2CCC3CC(OC4OCCCC4OC4OCCCC4OC4CCCCO4)CCC3C12
Scaffold Graph/Node level: C1CCC(OC2CCCOC2OC2CCCOC2OC2CCC3C(CCC4C3CCC35OCC6(CCCCC63)CCC45)C2)OC1
Scaffold Graph level: C1CCC(CC2CCCCC2CC2CCCCC2CC2CCC3C(CCC4C3CCC35CCC6(CCCCC63)CCC45)C2)CC1
Functional groups: CC=CC; CO; COC; CO[C@@H](C)OC; CO[C@H](C)OC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Terpene glycosides
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Triterpenoids
NP Classifier Class: Oleanane triterpenoids
Synonymous chemical names:
rotundioside f
External chemical identifiers:
CID:101093904; ZINC:ZINC000255217989
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Rotundioside F
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 911.14
Log P RDKit 1.66
Topological polar surface area (Å2) RDKit 246.68
Number of hydrogen bond acceptors RDKit 16
Number of hydrogen bond donors RDKit 9
Number of carbon atoms RDKit 48
Number of heavy atoms RDKit 64
Number of heteroatoms RDKit 16
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 25
Stereochemical complexity RDKit 0.52
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 2
Number of sp3 hybridized carbon atoms RDKit 46
Shape complexity RDKit 0.96
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 5
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 9
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 9
Number of saturated carbocycles RDKit 4
Number of saturated heterocycles RDKit 4
Number of saturated rings RDKit 8
Number of Smallest Set of Smallest Rings (SSSR) RDKit 9
Rotundioside F
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 3
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 0.1303