IMPPAT Phytochemical information: 
Glucobarbarin
Glucobarbarin
Summary

SMILES: OC[C@H]1O[C@@H](SC(=NOS(=O)(=O)O)CC(c2ccccc2)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C15H21NO10S2/c17-7-10-12(19)13(20)14(21)15(25-10)27-11(16-26-28(22,23)24)6-9(18)8-4-2-1-3-5-8/h1-5,9-10,12-15,17-21H,6-7H2,(H,22,23,24)/t9?,10-,12-,13+,14-,15+/m1/s1
InChIKey: GAPDDBFHNYHZIS-LNUNAXHXSA-N
DeepSMILES: OC[C@H]O[C@@H]SC=NOS=O)=O)O))))CCcccccc6))))))O)))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: N=C(CCc1ccccc1)SC1CCCCO1
Scaffold Graph/Node level: NC(CCC1CCCCC1)SC1CCCCO1
Scaffold Graph level: CC(CCC1CCCCC1)CC1CCCCC1
Functional groups: CO; CC(=NOS(=O)(=O)O)S[C@@H](C)OC
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: Amino acids and Peptides
NP Classifier Superclass: Amino acid glycosides
NP Classifier Class: Glucosinolates
Synonymous chemical names:
(2s)-glucobarbarin, glucobarbarin
External chemical identifiers:
CID:CID_46173883; ChEBI:CHEBI:81001
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Glucobarbarin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 439.46
Log P RDKit -1.22
Topological polar surface area (Å2) RDKit 186.34
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 28
Number of heteroatoms RDKit 13
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 2
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.4
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.53
Number of rotatable bonds RDKit 8
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
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
Glucobarbarin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 RDKit Failed
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 0.13
Glucobarbarin
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 -9.71
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 4
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