IMPPAT Phytochemical information: 
(2R,3R,4S,5R)-2-[[(1S,2R,3R)-7-hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-6,8-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl]methoxy]oxane-3,4,5-triol
(2R,3R,4S,5R)-2-[[(1S,2R,3R)-7-hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-6,8-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl]methoxy]oxane-3,4,5-triol
Summary

SMILES: OC[C@@H]1Cc2cc(OC)c(c(c2[C@@H]([C@H]1CO[C@@H]1OC[C@H]([C@@H]([C@H]1O)O)O)c1cc(OC)c(c(c1)OC)O)OC)O
InChI: InChI=1S/C27H36O12/c1-34-17-7-13(8-18(35-2)23(17)31)20-15(10-38-27-25(33)22(30)16(29)11-39-27)14(9-28)5-12-6-19(36-3)24(32)26(37-4)21(12)20/h6-8,14-16,20,22,25,27-33H,5,9-11H2,1-4H3/t14-,15-,16+,20+,22-,25+,27+/m0/s1
InChIKey: GWDZRGQRNHELQM-VEKSOEEBSA-N
DeepSMILES: OC[C@@H]CcccOC))ccc6[C@@H][C@H]%10CO[C@@H]OC[C@H][C@@H][C@H]6O))O))O))))))))cccOC))ccc6)OC)))O)))))))OC)))O
Scaffold Graph/Node/Bond level: c1ccc(C2c3ccccc3CCC2COC2CCCCO2)cc1
Scaffold Graph/Node level: C1CCC(C2C(COC3CCCCO3)CCC3CCCCC32)CC1
Scaffold Graph level: C1CCC(CCC2CCC3CCCCC3C2C2CCCCC2)CC1
Functional groups: CO; cOC; cO; CO[C@@H](C)OC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lignans, neolignans and related compounds
ClassyFire Class: Lignan glycosides
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Lignans
NP Classifier Class: Arylnaphthalene and aryltetralin lignans
Synonymous chemical names:
lyoniside, Lyoniside
External chemical identifiers:
CID:CID_14521039; ChEMBL:CHEMBL583884; ZINC:ZINC000049723059; MolPort-039-052-659
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(2R,3R,4S,5R)-2-[[(1S,2R,3R)-7-hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-6,8-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl]methoxy]oxane-3,4,5-triol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 552.57
Log P RDKit 0.5
Topological polar surface area (Å2) RDKit 176.76
Number of hydrogen bond acceptors RDKit 12
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 27
Number of heavy atoms RDKit 39
Number of heteroatoms RDKit 12
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 7
Stereochemical complexity RDKit 0.26
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 15
Shape complexity RDKit 0.56
Number of rotatable bonds RDKit 9
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
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
(2R,3R,4S,5R)-2-[[(1S,2R,3R)-7-hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-6,8-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl]methoxy]oxane-3,4,5-triol
Drug-likeness properties
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 3
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 0.254355
(2R,3R,4S,5R)-2-[[(1S,2R,3R)-7-hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-6,8-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl]methoxy]oxane-3,4,5-triol
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 -9.34
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