IMPPAT Phytochemical information: 
alpha-Viniferin
alpha-Viniferin
Summary

SMILES: Oc1cc2c3c(c1)O[C@H]([C@@H]3c1cc(O)cc3c1[C@@H](c1c4[C@H]2[C@H](Oc4cc(c1)O)c1ccc(cc1)O)[C@@H](O3)c1ccc(cc1)O)c1ccc(cc1)O
InChI: InChI=1S/C42H30O9/c43-22-7-1-19(2-8-22)40-37-28-13-25(46)17-32-35(28)39(42(50-32)21-5-11-24(45)12-6-21)30-15-27(48)18-33-36(30)38(29-14-26(47)16-31(49-40)34(29)37)41(51-33)20-3-9-23(44)10-4-20/h1-18,37-48H/t37-,38-,39+,40+,41+,42-/m1/s1
InChIKey: KUTVNHOAKHJJFL-ZSIJVUTGSA-N
DeepSMILES: Occcccc6)O[C@H][C@@H]5cccO)ccc6[C@@H]cc[C@H]%16[C@H]Oc5ccc9)O)))))cccccc6))O)))))))))[C@@H]O5)cccccc6))O))))))))))))))cccccc6))O
Scaffold Graph/Node/Bond level: c1ccc(C2Oc3cccc4c3C2c2cccc3c2C(c2cccc5c2C4C(c2ccccc2)O5)C(c2ccccc2)O3)cc1
Scaffold Graph/Node level: C1CCC(C2OC3CCCC4C3C2C2CCCC3OC(C5CCCCC5)C(C5CCCC6OC(C7CCCCC7)C4C65)C32)CC1
Scaffold Graph level: C1CCC(C2CC3CCCC4C3C2C2CCCC3CC(C5CCCCC5)C(C5CCCC6CC(C7CCCCC7)C4C65)C32)CC1
Functional groups: cO; 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:
alpha-viniferin
External chemical identifiers:
CID:CID_196402; ChEMBL:CHEMBL443463; ChEBI:CHEBI:66359; ZINC:ZINC000003935371; FDASRS:53XER6FHLX; SureChEMBL:SCHEMBL2721238
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
alpha-Viniferin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 678.69
Log P RDKit 8.03
Topological polar surface area (Å2) RDKit 149.07
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 42
Number of heavy atoms RDKit 51
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.14
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 36
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.14
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 6
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 6
Total number of rings RDKit 10
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 10
alpha-Viniferin
Drug-likeness
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
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 0.109404
alpha-Viniferin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Insoluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -5.59
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 Yes
alpha-Viniferin
Phytochemical - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_001299ENSG00000073756PTGS25743ChEMBL, NPASS