IMPPAT Phytochemical information: 
Beesioside I
Beesioside I
Summary

SMILES: CC(=O)O[C@@H]1[C@H](OC(=O)C)[C@H]2[C@@]3([C@]1(C)[C@@H]1CC[C@@H]4[C@@]5([C@@]1(CC3)C5)CC[C@@H](C4(C)C)O[C@@H]1OC[C@H]([C@@H]([C@H]1O)O)O)CO[C@@]1(O[C@@]2(C)CC1)C(O)(C)C
InChI: InChI=1S/C39H60O12/c1-20(40)48-28-29-34(7)13-16-39(51-34,33(5,6)45)47-19-38(29)15-14-37-18-36(37)12-11-25(50-31-27(44)26(43)22(42)17-46-31)32(3,4)23(36)9-10-24(37)35(38,8)30(28)49-21(2)41/h22-31,42-45H,9-19H2,1-8H3/t22-,23+,24+,25+,26+,27-,28-,29-,30-,31+,34+,35-,36-,37+,38+,39+/m1/s1
InChIKey: UZSZTNKGIQMEOL-QGODIXMOSA-N
DeepSMILES: CC=O)O[C@@H][C@H]OC=O)C)))[C@H][C@@][C@]5C)[C@@H]CC[C@@H][C@@][C@@]6CC%10))C3))CC[C@@H]C6C)C))O[C@@H]OC[C@H][C@@H][C@H]6O))O))O)))))))))))))))CO[C@@]O[C@@]7C)CC5))))CO)C)C
Scaffold Graph/Node/Bond level: C1CCC(OC2CCC34CC35CCC36COC7CCC(O7)C3CCC6C5CCC4C2)OC1
Scaffold Graph/Node level: C1CCC(OC2CCC34CC35CCC36COC7CCC(O7)C3CCC6C5CCC4C2)OC1
Scaffold Graph level: C1CCC(CC2CCC34CC35CCC36CCC7CCC(C7)C3CCC6C5CCC4C2)CC1
Functional groups: CC(=O)OC; CO; CO[C@@](C)(C)OC; CO[C@@H](OC)C
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: Triterpenoids
NP Classifier Class: Cycloartane triterpenoids
Synonymous chemical names:
beesioside i
External chemical identifiers:
CID:CID_15908521; ChEMBL:CHEMBL4550387; ZINC:ZINC000255272515
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Beesioside I
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 720.9
Log P RDKit 3.38
Topological polar surface area (Å2) RDKit 170.44
Number of hydrogen bond acceptors RDKit 12
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 39
Number of heavy atoms RDKit 51
Number of heteroatoms RDKit 12
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 16
Stereochemical complexity RDKit 0.41
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 2
Number of sp3 hybridized carbon atoms RDKit 37
Shape complexity RDKit 0.95
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 5
Number of aliphatic heterocycles RDKit 3
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 5
Number of saturated heterocycles RDKit 3
Number of saturated rings RDKit 8
Number of Smallest Set of Smallest Rings (SSSR) RDKit 8
Beesioside I
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 3
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.241719
Beesioside I
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 -8.43
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
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