IMPPAT Phytochemical information: 
Yadanzioside O
Yadanzioside O
Summary

SMILES: OC[C@H]1O[C@@H](OC2=C[C@@]3(C)[C@H]([C@@H](C2=O)C)C[C@@H]2[C@@]45[C@@H]3[C@@H](O)[C@H](O)[C@]([C@@H]5[C@H](C(=O)O2)OC(=O)/C=C(/C(OC(=O)C)(C)C)\CC)(OC4)C(=O)OC)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C37H50O18/c1-8-16(34(4,5)55-15(3)39)9-21(40)54-27-29-36-13-50-37(29,33(48)49-7)30(46)26(45)28(36)35(6)11-18(22(41)14(2)17(35)10-20(36)53-31(27)47)51-32-25(44)24(43)23(42)19(12-38)52-32/h9,11,14,17,19-20,23-30,32,38,42-46H,8,10,12-13H2,1-7H3/b16-9+/t14-,17-,19+,20+,23+,24-,25+,26+,27+,28+,29+,30-,32+,35-,36+,37-/m0/s1
InChIKey: INEPMPYUXFBNMS-HRXLEDENSA-N
DeepSMILES: OC[C@H]O[C@@H]OC=C[C@@]C)[C@H][C@@H]C6=O))C))C[C@@H][C@][C@@H]6[C@@H]O)[C@H]O)[C@][C@@H]6[C@H]C=O)O%10))OC=O)/C=C/COC=O)C)))C)C))\CC))))))))OC7))C=O)OC)))))))))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C1CC2C3CCC4C5C=C(OC6CCCCO6)C(=O)CC5CC(O1)C24CO3
Scaffold Graph/Node level: OC1CC2C3CCC4C5CC(OC6CCCCO6)C(O)CC5CC(O1)C24CO3
Scaffold Graph level: CC1CC2CC3CC(C)C(CC4CCCCC4)CC3C3CCC4CCC23C4C1
Functional groups: CO; CC=C(O[C@@H](C)OC)C(=O)C; COC(=O)C; C/C(C)=C/C(=O)OC; COC(C)=O; COC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Terpene lactones
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Triterpenoids
NP Classifier Class: Quassinoids
Synonymous chemical names:
Yadanzioside O, yadanziosides o, yadanzioside o
External chemical identifiers:
CID:CID_10417797; ZINC:ZINC000255219872
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Yadanzioside O
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 782.79
Log P RDKit -1.66
Topological polar surface area (Å2) RDKit 271.34
Number of hydrogen bond acceptors RDKit 18
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 37
Number of heavy atoms RDKit 55
Number of heteroatoms RDKit 18
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 16
Stereochemical complexity RDKit 0.43
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 28
Shape complexity RDKit 0.76
Number of rotatable bonds RDKit 12
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 6
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 2
Number of saturated heterocycles RDKit 3
Number of saturated rings RDKit 5
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6
Yadanzioside O
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 4
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 0.0868112
Yadanzioside O
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 -10.73
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