IMPPAT Phytochemical information: 
Paederoside
Paederoside
Summary

SMILES: OC[C@H]1O[C@@H](O[C@@H]2OC=C3[C@@H]4[C@H]2C(=C[C@@H]4OC3=O)COC(=O)SC)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C18H22O11S/c1-30-18(24)26-4-6-2-8-11-7(15(23)27-8)5-25-16(10(6)11)29-17-14(22)13(21)12(20)9(3-19)28-17/h2,5,8-14,16-17,19-22H,3-4H2,1H3/t8-,9+,10+,11-,12+,13-,14+,16-,17-/m0/s1
InChIKey: OJISWUQNQQWEND-FCVLBCLDSA-N
DeepSMILES: OC[C@H]O[C@@H]O[C@@H]OC=C[C@@H][C@H]6C=C[C@@H]5OC8=O)))))COC=O)SC)))))))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C1OC2C=CC3C(OC4CCCCO4)OC=C1C23
Scaffold Graph/Node level: OC1OC2CCC3C(OC4CCCCO4)OCC1C23
Scaffold Graph level: CC1CC2CCC3C(CC4CCCCC4)CCC1C23
Functional groups: CO; CO[C@@H](O[C@H]1C[C@@H]2COC(=O)C2=CO1)C; CC(=CC)C; COC(=O)SC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Carbohydrates and carbohydrate conjugates
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Monoterpenoids
NP Classifier Class: Iridoids monoterpenoids
Synonymous chemical names:
paederoside, Paederoside
External chemical identifiers:
CID:CID_442432; ChEMBL:CHEMBL517133; ChEBI:CHEBI:7888; ZINC:ZINC000004098349; SureChEMBL:SCHEMBL422181; MolPort-001-741-059
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Paederoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 446.43
Log P RDKit -1.36
Topological polar surface area (Å2) RDKit 161.21
Number of hydrogen bond acceptors RDKit 12
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 30
Number of heteroatoms RDKit 12
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 1
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.5
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 6
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.67
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
Paederoside
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 1
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 0.290379
Paederoside
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.11
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -10.07
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 3
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