IMPPAT Phytochemical information: 
Vanillyl beta-D-glucopyranoside

Vanillyl beta-D-glucopyranoside
Summary

SMILES: OC[C@H]1O[C@@H](OCc2ccc(c(c2)OC)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C14H20O8/c1-20-9-4-7(2-3-8(9)16)6-21-14-13(19)12(18)11(17)10(5-15)22-14/h2-4,10-19H,5-6H2,1H3/t10-,11-,12+,13-,14-/m1/s1
InChIKey: XNUBWLDOGBNCKT-RKQHYHRCSA-N
DeepSMILES: OC[C@H]O[C@@H]OCcccccc6)OC)))O)))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: c1ccc(COC2CCCCO2)cc1
Scaffold Graph/Node level: C1CCC(COC2CCCCO2)CC1
Scaffold Graph level: C1CCC(CCC2CCCCC2)CC1
Functional groups: CO; CO[C@@H](C)OC; cOC; cO
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: Shikimates and Phenylpropanoids
Synonymous chemical names:
vanillyl alcohol-phenylglucoside
External chemical identifiers:
CID:CID_21627672; ChEBI:CHEBI:86958; ZINC:ZINC000095639295
Chemical structure download


Vanillyl beta-D-glucopyranoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 316.31
Log P RDKit -1.28
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 14
Number of heavy atoms RDKit 22
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.36
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 6
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.57
Number of rotatable bonds RDKit 5
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


Vanillyl beta-D-glucopyranoside
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 0.454088


Vanillyl beta-D-glucopyranoside
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 -9.00
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
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