IMPPAT Phytochemical information: 
(+)-Isolariciresinol monoglucoside
(+)-Isolariciresinol monoglucoside
Summary

SMILES: OC[C@@H]1Cc2cc(OC)c(cc2[C@@H](C1C1(OC)O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)c1ccc(c(c1)OC)O)O
InChI: InChI=1S/C26H34O11/c1-34-18-7-12(4-5-16(18)29)21-15-9-17(30)19(35-2)8-13(15)6-14(10-27)22(21)26(36-3)25(33)24(32)23(31)20(11-28)37-26/h4-5,7-9,14,20-25,27-33H,6,10-11H2,1-3H3/t14-,20+,21-,22?,23+,24-,25+,26?/m0/s1
InChIKey: VRDFUQQTQIRXIH-WTCHXSQLSA-N
DeepSMILES: OC[C@@H]CcccOC))ccc6[C@@H]C%10COC))O[C@H]CO))[C@H][C@@H][C@H]6O))O))O))))))cccccc6)OC)))O))))))))O
Scaffold Graph/Node/Bond level: c1ccc(C2c3ccccc3CCC2C2CCCCO2)cc1
Scaffold Graph/Node level: C1CCC(C2C3CCCCC3CCC2C2CCCCO2)CC1
Scaffold Graph level: C1CCC(C2CCC3CCCCC3C2C2CCCCC2)CC1
Functional groups: CO; cOC; cO; COC(C)(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:
d-isolariciresinol-mono-beta-d-glucopyranoside
External chemical identifiers:
CID:CID_180275
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(+)-Isolariciresinol monoglucoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 522.55
Log P RDKit -0.16
Topological polar surface area (Å2) RDKit 178.53
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 7
Number of carbon atoms RDKit 26
Number of heavy atoms RDKit 37
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 8
Stereochemical complexity RDKit 0.31
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 14
Shape complexity RDKit 0.54
Number of rotatable bonds RDKit 7
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
(+)-Isolariciresinol monoglucoside
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 2
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.26
(+)-Isolariciresinol monoglucoside
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 -9.30
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