IMPPAT Phytochemical information: 
5-[(2S,3S)-4-[(E)-2-[(3S)-3-[(3S)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-yl]ethenyl]-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol
5-[(2S,3S)-4-[(E)-2-[(3S)-3-[(3S)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-yl]ethenyl]-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol
Summary

SMILES: Oc1ccc(cc1)C1Oc2c([C@@H]1c1cc(O)cc3c1[C@H](c1cc(O)cc(c1)O)C(O3)c1ccc(cc1)O)cc(cc2)/C=C/c1cc(O)cc2c1[C@H](c1cc(O)cc(c1)O)[C@H](O2)c1ccc(cc1)O
InChI: InChI=1S/C56H42O12/c57-35-10-4-29(5-11-35)54-50(33-19-38(60)23-39(61)20-33)49-32(18-42(64)26-47(49)67-54)3-1-28-2-16-46-44(17-28)52(56(66-46)31-8-14-37(59)15-9-31)45-25-43(65)27-48-53(45)51(34-21-40(62)24-41(63)22-34)55(68-48)30-6-12-36(58)13-7-30/h1-27,50-52,54-65H/b3-1+/t50-,51-,52+,54+,55?,56?/m0/s1
InChIKey: WZKKRZSJTLGPHH-GXHOOJFBSA-N
DeepSMILES: Occcccc6))COcc[C@@H]5cccO)ccc6[C@H]cccO)ccc6)O))))))CO5)cccccc6))O))))))))))))))cccc6))/C=C/cccO)ccc6[C@H]cccO)ccc6)O))))))[C@H]O5)cccccc6))O
Scaffold Graph/Node/Bond level: C(=Cc1cccc2c1C(c1ccccc1)C(c1ccccc1)O2)c1ccc2c(c1)C(c1cccc3c1C(c1ccccc1)C(c1ccccc1)O3)C(c1ccccc1)O2
Scaffold Graph/Node level: C1CCC(C2OC3CCC(CCC4CCCC5OC(C6CCCCC6)C(C6CCCCC6)C45)CC3C2C2CCCC3OC(C4CCCCC4)C(C4CCCCC4)C32)CC1
Scaffold Graph level: C1CCC(C2CC3CCC(CCC4CCCC5CC(C6CCCCC6)C(C6CCCCC6)C45)CC3C2C2CCCC3CC(C4CCCCC4)C(C4CCCCC4)C32)CC1
Functional groups: cO; cOC; c/C=C/c
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:
vitisin c
External chemical identifiers:
CID:CID_46890015; ChEMBL:CHEMBL1082603
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
5-[(2S,3S)-4-[(E)-2-[(3S)-3-[(3S)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-yl]ethenyl]-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 906.94
Log P RDKit 11
Topological polar surface area (Å2) RDKit 209.76
Number of hydrogen bond acceptors RDKit 12
Number of hydrogen bond donors RDKit 9
Number of carbon atoms RDKit 56
Number of heavy atoms RDKit 68
Number of heteroatoms RDKit 12
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.11
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 50
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.11
Number of rotatable bonds RDKit 8
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 8
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 8
Total number of rings RDKit 11
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 11
5-[(2S,3S)-4-[(E)-2-[(3S)-3-[(3S)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-yl]ethenyl]-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 4
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 4
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.065248
5-[(2S,3S)-4-[(E)-2-[(3S)-3-[(3S)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-yl]ethenyl]-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Insoluble
Solubility class [Silicos-IT] SwissADME Insoluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -4.76
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