IMPPAT Phytochemical information: 
(2S,3R,4S,5S,6R)-2-[2,4-dihydroxy-6-[(E)-2-(4-hydroxyphenyl)ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
(2S,3R,4S,5S,6R)-2-[2,4-dihydroxy-6-[(E)-2-(4-hydroxyphenyl)ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Summary

SMILES: OC[C@H]1O[C@@H](Oc2c(/C=C/c3ccc(cc3)O)cc(cc2O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C20H22O9/c21-9-15-16(25)17(26)18(27)20(28-15)29-19-11(7-13(23)8-14(19)24)4-1-10-2-5-12(22)6-3-10/h1-8,15-18,20-27H,9H2/b4-1+/t15-,16-,17+,18-,20+/m1/s1
InChIKey: JAYVHSBYKLLDJC-DSNJPTTOSA-N
DeepSMILES: OC[C@H]O[C@@H]Occ/C=C/cccccc6))O)))))))cccc6O)))O))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: C(=Cc1ccccc1OC1CCCCO1)c1ccccc1
Scaffold Graph/Node level: C1CCC(CCC2CCCCC2OC2CCCCO2)CC1
Scaffold Graph level: C1CCC(CCC2CCCCC2CC2CCCCC2)CC1
Functional groups: CO; cO[C@@H](C)OC; c/C=C/c; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Stilbenes
ClassyFire Subclass: Stilbene glycosides
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Stilbenoids
NP Classifier Class: Monomeric stilbenes
Synonymous chemical names:
2,3,5,4'-tetrahydroxystilbene-2-o-β-d-glucoside, 2-3-4'-5-tetrahydroxystilbene, 2,3,5,4'-tetrahydroxystilbene-2-o-beta-d-glucoside
External chemical identifiers:
CID:CID_5321884; ChEMBL:CHEMBL460860; ChEBI:CHEBI:140850; ZINC:ZINC000006092613; FDASRS:54QRI6OKJ5; SureChEMBL:SCHEMBL2688101; MolPort-008-155-937
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(2S,3R,4S,5S,6R)-2-[2,4-dihydroxy-6-[(E)-2-(4-hydroxyphenyl)ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 406.39
Log P RDKit 0.15
Topological polar surface area (Å2) RDKit 160.07
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 7
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 29
Number of heteroatoms RDKit 9
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 5
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
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
(2S,3R,4S,5S,6R)-2-[2,4-dihydroxy-6-[(E)-2-(4-hydroxyphenyl)ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
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 0.34302
(2S,3R,4S,5S,6R)-2-[2,4-dihydroxy-6-[(E)-2-(4-hydroxyphenyl)ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
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 -8.09
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