IMPPAT Phytochemical information: 
Roseoside
Roseoside
Summary

SMILES: OC[C@H]1O[C@@H](O[C@@H](/C=C/[C@@]2(O)C(=CC(=O)CC2(C)C)C)C)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C19H30O8/c1-10-7-12(21)8-18(3,4)19(10,25)6-5-11(2)26-17-16(24)15(23)14(22)13(9-20)27-17/h5-7,11,13-17,20,22-25H,8-9H2,1-4H3/b6-5+/t11-,13-,14-,15+,16-,17-,19-/m1/s1
InChIKey: SWYRVCGNMNAFEK-MHXFFUGFSA-N
DeepSMILES: OC[C@H]O[C@@H]O[C@@H]/C=C/[C@@]O)C=CC=O)CC6C)C)))))C)))))C)))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C1C=CC(C=CCOC2CCCCO2)CC1
Scaffold Graph/Node level: OC1CCC(CCCOC2CCCCO2)CC1
Scaffold Graph level: CC1CCC(CCCCC2CCCCC2)CC1
Functional groups: CO; CO[C@@H](C)OC; C/C=C/C; CC(=O)C=C(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Fatty Acyls
ClassyFire Subclass: Fatty acyl glycosides
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Apocarotenoids
NP Classifier Class: Megastigmanes
Synonymous chemical names:
(6s,9r)-roseoside, Roseoside, roseoside
External chemical identifiers:
CID:CID_9930064; ChEMBL:CHEMBL482383; ZINC:ZINC000031154891; FDASRS:BOE4GN3B64; MolPort-035-706-262
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Roseoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 386.44
Log P RDKit -0.58
Topological polar surface area (Å2) RDKit 136.68
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 7
Stereochemical complexity RDKit 0.37
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 14
Shape complexity RDKit 0.74
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
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
Roseoside
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 1
Ghose rule RDKit Failed
Veber rule RDKit Good
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 0.4
Roseoside
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
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 -9.40
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