IMPPAT Phytochemical information: 
Beesioside III
Beesioside III
Summary

SMILES: CC(=O)O[C@H]1[C@H](O)[C@@H]([C@@]2([C@]1(C)[C@@H]1CC[C@@H]3[C@@]4([C@]1(C4)C[C@H]2O)CC[C@@H](C3(C)C)O[C@@H]1OC[C@H]([C@@H]([C@H]1O)O)O)C)C1(C)CCC(O1)C(O)(C)C
InChI: InChI=1S/C37H60O11/c1-18(38)46-29-27(43)28(33(6)13-11-24(48-33)32(4,5)44)35(8)22(40)15-37-17-36(37)14-12-23(47-30-26(42)25(41)19(39)16-45-30)31(2,3)20(36)9-10-21(37)34(29,35)7/h19-30,39-44H,9-17H2,1-8H3/t19-,20+,21+,22-,23+,24?,25+,26-,27-,28-,29+,30+,33?,34-,35-,36-,37+/m1/s1
InChIKey: FRLGNHGNKSPOGU-LYRNJPNDSA-N
DeepSMILES: CC=O)O[C@H][C@H]O)[C@@H][C@@][C@]5C)[C@@H]CC[C@@H][C@@][C@]6C3)C[C@H]%10O))))CC[C@@H]C6C)C))O[C@@H]OC[C@H][C@@H][C@H]6O))O))O)))))))))))))))C))CC)CCCO5)CO)C)C
Scaffold Graph/Node/Bond level: C1CCC(OC2CCC34CC35CCC3C(C6CCCO6)CCC3C5CCC4C2)OC1
Scaffold Graph/Node level: C1CCC(OC2CCC34CC35CCC3C(C6CCCO6)CCC3C5CCC4C2)OC1
Scaffold Graph level: C1CCC(CC2CCC34CC35CCC3C(C6CCCC6)CCC3C5CCC4C2)CC1
Functional groups: CC(=O)OC; CO; COC; 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 iii
External chemical identifiers:
CID:CID_21637572
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Beesioside III
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 680.88
Log P RDKit 2.44
Topological polar surface area (Å2) RDKit 175.37
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 37
Number of heavy atoms RDKit 48
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 17
Stereochemical complexity RDKit 0.46
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 1
Number of sp3 hybridized carbon atoms RDKit 36
Shape complexity RDKit 0.97
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 5
Number of aliphatic heterocycles RDKit 2
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 5
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 7
Number of Smallest Set of Smallest Rings (SSSR) RDKit 7
Beesioside III
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 0.19
Beesioside III
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 -8.71
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