IMPPAT Phytochemical information: 
Bartsioside
Bartsioside
Summary

SMILES: OCC1=CC[C@@H]2[C@H]1[C@@H](OC=C2)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
InChI: InChI=1S/C15H22O8/c16-5-8-2-1-7-3-4-21-14(10(7)8)23-15-13(20)12(19)11(18)9(6-17)22-15/h2-4,7,9-20H,1,5-6H2/t7-,9+,10+,11+,12-,13+,14-,15-/m0/s1
InChIKey: FCHJZJFIDNMNBS-DNRYLMBSSA-N
DeepSMILES: OCC=CC[C@@H][C@H]5[C@@H]OC=C6)))O[C@@H]O[C@H]CO))[C@H][C@@H][C@H]6O))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=C(C)C; CO[C@@H](O[C@H]1CCC=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:
bartsioside
External chemical identifiers:
CID:CID_14081907
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Bartsioside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 330.33
Log P RDKit -1.77
Topological polar surface area (Å2) RDKit 128.84
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 8
Stereochemical complexity RDKit 0.53
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 4
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.73
Number of rotatable bonds RDKit 4
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
Bartsioside
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 1
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.383051
Bartsioside
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 -9.67
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