IMPPAT Phytochemical information: 
Oleoside dimethyl ester
Oleoside dimethyl ester
Summary

SMILES: COC(=O)C[C@H]1/C(=C/C)/[C@@H](OC=C1C(=O)OC)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
InChI: InChI=1S/C18H26O11/c1-4-8-9(5-12(20)25-2)10(16(24)26-3)7-27-17(8)29-18-15(23)14(22)13(21)11(6-19)28-18/h4,7,9,11,13-15,17-19,21-23H,5-6H2,1-3H3/b8-4-/t9-,11+,13+,14-,15+,17-,18-/m0/s1
InChIKey: KYVUMEGNMQDSHO-ISEXSMSQSA-N
DeepSMILES: COC=O)C[C@H]/C=C/C))/[C@@H]OC=C6C=O)OC))))))O[C@@H]O[C@H]CO))[C@H][C@@H][C@H]6O))O))O
Scaffold Graph/Node/Bond level: C=C1CC=COC1OC1CCCCO1
Scaffold Graph/Node level: CC1CCCOC1OC1CCCCO1
Scaffold Graph level: CC1CCCCC1CC1CCCCC1
Functional groups: COC(C)=O; C/C=C1/CC(C(=O)OC)=CO[C@H]1O[C@@H](C)OC; CO
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: Secoiridoid monoterpenoids
Synonymous chemical names:
oleoside dimethylester
External chemical identifiers:
CID:CID_14038300; ChEMBL:CHEMBL1087778; ZINC:ZINC000031161343
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Oleoside dimethyl ester
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 418.4
Log P RDKit -1.66
Topological polar surface area (Å2) RDKit 161.21
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 29
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 7
Stereochemical complexity RDKit 0.39
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 8
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 2
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 2
Oleoside dimethyl ester
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 Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.29
Oleoside dimethyl ester
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 -10.05
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 No