IMPPAT Phytochemical information: 
4-[(2R,3R)-3-(3,5-dihydroxyphenyl)-6-hydroxy-4-[(Z)-2-(4-hydroxyphenyl)vinyl]-2,3-dihydrobenzofuran-2-yl]benzene-1,2-diol
4-[(2R,3R)-3-(3,5-dihydroxyphenyl)-6-hydroxy-4-[(Z)-2-(4-hydroxyphenyl)vinyl]-2,3-dihydrobenzofuran-2-yl]benzene-1,2-diol
Summary

SMILES: Oc1cc(/C=C\c2ccc(cc2)O)c2c(c1)O[C@H]([C@@H]2c1cc(O)cc(c1)O)c1ccc(c(c1)O)O
InChI: InChI=1S/C28H22O7/c29-19-6-2-15(3-7-19)1-4-16-9-22(32)14-25-26(16)27(18-10-20(30)13-21(31)11-18)28(35-25)17-5-8-23(33)24(34)12-17/h1-14,27-34H/b4-1-/t27-,28+/m1/s1
InChIKey: VJVQHVVOEFJLIO-HQAJZZHBSA-N
DeepSMILES: Occc/C=C\cccccc6))O)))))))ccc6)O[C@H][C@@H]5cccO)ccc6)O)))))))cccccc6)O))O
Scaffold Graph/Node/Bond level: C(=Cc1cccc2c1C(c1ccccc1)C(c1ccccc1)O2)c1ccccc1
Scaffold Graph/Node level: C1CCC(CCC2CCCC3OC(C4CCCCC4)C(C4CCCCC4)C23)CC1
Scaffold Graph level: C1CCC(CCC2CCCC3CC(C4CCCCC4)C(C4CCCCC4)C23)CC1
Functional groups: cO; c/C=C\c; cOC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: 2-arylbenzofuran flavonoids
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Stilbenoids
NP Classifier Class: Oligomeric stibenes
Synonymous chemical names:
scirpusin a
External chemical identifiers:
CID:CID_5279245; ZINC:ZINC000014693073
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
4-[(2R,3R)-3-(3,5-dihydroxyphenyl)-6-hydroxy-4-[(Z)-2-(4-hydroxyphenyl)vinyl]-2,3-dihydrobenzofuran-2-yl]benzene-1,2-diol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 470.48
Log P RDKit 5.36
Topological polar surface area (Å2) RDKit 130.61
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 28
Number of heavy atoms RDKit 35
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.07
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 26
Number of sp3 hybridized carbon atoms RDKit 2
Shape complexity RDKit 0.07
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 4
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 4
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
4-[(2R,3R)-3-(3,5-dihydroxyphenyl)-6-hydroxy-4-[(Z)-2-(4-hydroxyphenyl)vinyl]-2,3-dihydrobenzofuran-2-yl]benzene-1,2-diol
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 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.17494
4-[(2R,3R)-3-(3,5-dihydroxyphenyl)-6-hydroxy-4-[(Z)-2-(4-hydroxyphenyl)vinyl]-2,3-dihydrobenzofuran-2-yl]benzene-1,2-diol
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -5.58
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 Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No