IMPPAT Phytochemical information: 
2,3-(S)-hexahydroxydiphenoyl-D-glucose
2,3-(S)-hexahydroxydiphenoyl-D-glucose
Summary

SMILES: OCC1OC(O)C2C(C1O)OC(=O)c1cc(O)c(c(c1-c1c(C(=O)O2)cc(O)c(c1O)O)O)O
InChI: InChI=1S/C20H18O14/c21-3-8-13(26)16-17(20(31)32-8)34-19(30)5-2-7(23)12(25)15(28)10(5)9-4(18(29)33-16)1-6(22)11(24)14(9)27/h1-2,8,13,16-17,20-28,31H,3H2
InChIKey: GEAGRKQCZVLNAU-UHFFFAOYSA-N
DeepSMILES: OCCOCO)CCC6O))OC=O)cccO)ccc6-ccC=O)O%14))ccO)cc6O))O)))))))O))O
Scaffold Graph/Node/Bond level: O=C1OC2CCOCC2OC(=O)c2ccccc2-c2ccccc21
Scaffold Graph/Node level: OC1OC2CCOCC2OC(O)C2CCCCC2C2CCCCC12
Scaffold Graph level: CC1CC2CCCCC2CC(C)C2CCCCC2C2CCCCC12
Functional groups: CO; cO; COC(O)C; cC(=O)OC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Tannins
ClassyFire Subclass: Hydrolyzable tannins
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Phenolic acids (C6-C1)
NP Classifier Class: Gallotannins
Synonymous chemical names:
4,6-hexahydroxydiphenoyl glucose, 2,3(s)-hhdp-6-o-galloyl-d-glucose
External chemical identifiers:
CID:CID_492390
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
2,3-(S)-hexahydroxydiphenoyl-D-glucose
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 482.35
Log P RDKit -1.28
Topological polar surface area (Å2) RDKit 243.9
Number of hydrogen bond acceptors RDKit 14
Number of hydrogen bond donors RDKit 9
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 34
Number of heteroatoms RDKit 14
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.25
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 14
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.3
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 4
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 4
2,3-(S)-hexahydroxydiphenoyl-D-glucose
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 2
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.169815
2,3-(S)-hexahydroxydiphenoyl-D-glucose
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -9.63
Number of PAINS structural alerts SwissADME 1
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