IMPPAT Phytochemical information: 
Paniculoside III
Paniculoside III
Summary

SMILES: OC[C@H]1O[C@@H](OC(=O)[C@]2(C)CCC[C@@]3([C@@H]2CC[C@]24[C@H]3[C@@H](O)C[C@H](C2)C(=C)C4=O)C)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C26H38O9/c1-12-13-9-14(28)20-24(2)6-4-7-25(3,16(24)5-8-26(20,10-13)21(12)32)23(33)35-22-19(31)18(30)17(29)15(11-27)34-22/h13-20,22,27-31H,1,4-11H2,2-3H3/t13-,14+,15-,16+,17-,18+,19-,20+,22+,24-,25-,26-/m1/s1
InChIKey: JSKLOHJUYDOADP-DQGZFUNPSA-N
DeepSMILES: OC[C@H]O[C@@H]OC=O)[C@]C)CCC[C@@][C@@H]6CC[C@][C@H]6[C@@H]O)C[C@H]C6)C=C)C7=O)))))))))))C))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: C=C1C(=O)C23CCC4C(C(=O)OC5CCCCO5)CCCC4C2CCC1C3
Scaffold Graph/Node level: CC1C2CCC3C4CCCC(C(O)OC5CCCCO5)C4CCC3(C2)C1O
Scaffold Graph level: CC(CC1CCCCC1)C1CCCC2C1CCC13CC(CCC21)C(C)C3C
Functional groups: CO; CO[C@@H](OC(C)=O)C; C=C(C)C(=O)C
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: Diterpenoids
NP Classifier Class: Kaurane and Phyllocladane diterpenoids
Synonymous chemical names:
paniculosides iii
External chemical identifiers:
CID:CID_21593625; ZINC:ZINC000255221709
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Paniculoside III
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 494.58
Log P RDKit 0.45
Topological polar surface area (Å2) RDKit 153.75
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 26
Number of heavy atoms RDKit 35
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 12
Stereochemical complexity RDKit 0.46
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 4
Number of sp3 hybridized carbon atoms RDKit 22
Shape complexity RDKit 0.85
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 4
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 5
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
Paniculoside III
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 2
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 0.28
Paniculoside III
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -8.42
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