IMPPAT Phytochemical information: 
Volubiloside A
Volubiloside A
Summary

SMILES: CO[C@H]1C[C@@H](O[C@@H]([C@H]1O[C@H]1C[C@H](OC)[C@@H]([C@H](O1)C)O[C@@H]1O[C@H](C)[C@H]([C@H]([C@H]1O)OC)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)C)[C@H]1CC[C@]2(C(=CC[C@@H]3[C@@H]2[C@H](O)C(O)[C@]2([C@]3(O)CC[C@@H]2[C@H](O)C)C)C1)C
InChI: InChI=1S/C48H80O19/c1-20(50)26-13-15-48(57)27-11-10-25-16-24(12-14-46(25,5)33(27)35(52)43(56)47(26,48)6)28-17-29(58-7)39(21(2)61-28)65-32-18-30(59-8)40(22(3)62-32)66-45-38(55)42(60-9)41(23(4)63-45)67-44-37(54)36(53)34(51)31(19-49)64-44/h10,20-24,26-45,49-57H,11-19H2,1-9H3/t20-,21-,22-,23-,24+,26-,27-,28-,29+,30+,31-,32+,33-,34-,35+,36+,37-,38-,39-,40-,41-,42+,43?,44+,45+,46+,47+,48+/m1/s1
InChIKey: HMUVMTSJOQNAII-UYPPRYDFSA-N
DeepSMILES: CO[C@H]C[C@@H]O[C@@H][C@H]6O[C@H]C[C@H]OC))[C@@H][C@H]O6)C))O[C@@H]O[C@H]C)[C@H][C@H][C@H]6O))OC)))O[C@@H]O[C@H]CO))[C@H][C@@H][C@H]6O))O))O)))))))))))))))))C)))[C@H]CC[C@]C=CC[C@@H][C@@H]6[C@H]O)CO)[C@][C@]6O)CC[C@@H]5[C@H]O)C))))))C))))))))C6))C
Scaffold Graph/Node/Bond level: C1=C2CC(C3CCC(OC4CCC(OC5CCC(OC6CCCCO6)CO5)CO4)CO3)CCC2C2CCC3CCCC3C2C1
Scaffold Graph/Node level: C1CCC(OC2CCC(OC3CCC(OC4CCC(C5CCC6C(CCC7C8CCCC8CCC67)C5)OC4)OC3)OC2)OC1
Scaffold Graph level: C1CCC(CC2CCC(CC3CCC(CC4CCC(C5CCC6C(CCC7C8CCCC8CCC67)C5)CC4)CC3)CC2)CC1
Functional groups: CC=C(C)C; CO; COC; CO[C@@H](C)OC; C[C@H](OC)OC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Steroids and steroid derivatives
ClassyFire Subclass: Steroidal glycosides
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Steroids
NP Classifier Class: Pregnane steroids
Synonymous chemical names:
volubiloside a [drevogenin d-3-o-beta-d-glucopyranosyl(1->4)-6-deoxy-3-o-methyl-beta-d-allopyranosyl(1->4)-beta-d-cymaropyranosyl(1->4)-beta-d-cymaropyranoside]
External chemical identifiers:
CID:101210565
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Volubiloside A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 961.15
Log P RDKit 0.04
Topological polar surface area (Å2) RDKit 274.37
Number of hydrogen bond acceptors RDKit 19
Number of hydrogen bond donors RDKit 9
Number of carbon atoms RDKit 48
Number of heavy atoms RDKit 67
Number of heteroatoms RDKit 19
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 28
Stereochemical complexity RDKit 0.58
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 12
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 8
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 8
Number of saturated carbocycles RDKit 3
Number of saturated heterocycles RDKit 4
Number of saturated rings RDKit 7
Number of Smallest Set of Smallest Rings (SSSR) RDKit 8
Volubiloside A
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 0.1169