IMPPAT Phytochemical information: 
Scandoside
Scandoside
Summary

SMILES: OCC1=C[C@H]([C@H]2[C@@H]1[C@@H](OC=C2C(=O)O)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)O
InChI: InChI=1S/C16H22O11/c17-2-5-1-7(19)10-6(14(23)24)4-25-15(9(5)10)27-16-13(22)12(21)11(20)8(3-18)26-16/h1,4,7-13,15-22H,2-3H2,(H,23,24)/t7-,8-,9-,10+,11-,12+,13-,15+,16+/m1/s1
InChIKey: ZVXWFPTVHBWJOU-AWQYILTISA-N
DeepSMILES: OCC=C[C@H][C@H][C@@H]5[C@@H]OC=C6C=O)O)))))O[C@@H]O[C@H]CO))[C@H][C@@H][C@H]6O))O))O)))))))))O
Scaffold Graph/Node/Bond level: C1=CC2C(C=COC2OC2CCCCO2)C1
Scaffold Graph/Node level: C1CCC(OC2OCCC3CCCC32)OC1
Scaffold Graph level: C1CCC(CC2CCCC3CCCC32)CC1
Functional groups: CO; CC(=CC)C; CO[C@@H](O[C@H]1CCC(C(=O)O)=CO1)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: Monoterpenoids
NP Classifier Class: Iridoids monoterpenoids
Synonymous chemical names:
Scandoside, scandosides, scandoside (iridoid glycoside), scandoside
External chemical identifiers:
CID:CID_21602023; ChEMBL:CHEMBL459415; ZINC:ZINC000038321680; SureChEMBL:SCHEMBL307654; MolPort-039-338-648
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Scandoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 390.34
Log P RDKit -3.35
Topological polar surface area (Å2) RDKit 186.37
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 7
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.56
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.69
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3
Scandoside
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 1
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.23
Scandoside
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.11
Solubility class [ESOL] SwissADME Highly soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -11.36
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 No