IMPPAT Phytochemical information: 
Licuroside
Licuroside
Summary

SMILES: OCC1OC(Oc2ccc(cc2)/C=C/C(=O)c2ccc(cc2O)O)C(C(C1O)O)OC1OCC(C1O)(O)CO
InChI: InChI=1S/C26H30O13/c27-10-19-20(32)21(33)22(39-25-23(34)26(35,11-28)12-36-25)24(38-19)37-15-5-1-13(2-6-15)3-8-17(30)16-7-4-14(29)9-18(16)31/h1-9,19-25,27-29,31-35H,10-12H2/b8-3+
InChIKey: VMMVZVPAYFZNBM-FPYGCLRLSA-N
DeepSMILES: OCCOCOcccccc6))/C=C/C=O)cccccc6O)))O)))))))))))))CCC6O))O))OCOCCC5O))O)CO
Scaffold Graph/Node/Bond level: O=C(C=Cc1ccc(OC2OCCCC2OC2CCCO2)cc1)c1ccccc1
Scaffold Graph/Node level: OC(CCC1CCC(OC2OCCCC2OC2CCCO2)CC1)C1CCCCC1
Scaffold Graph level: CC(CCC1CCC(CC2CCCCC2CC2CCCC2)CC1)C1CCCCC1
Functional groups: CO; cOC(C)OC; c/C=C/C(c)=O; cO; COC(C)OC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Flavonoids
ClassyFire Subclass: Flavonoid glycosides
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Flavonoids
NP Classifier Class: Chalcones
Synonymous chemical names:
licuraside, licuroside
External chemical identifiers:
CID:CID_6475724
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Licuroside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 550.51
Log P RDKit -1.36
Topological polar surface area (Å2) RDKit 215.83
Number of hydrogen bond acceptors RDKit 13
Number of hydrogen bond donors RDKit 8
Number of carbon atoms RDKit 26
Number of heavy atoms RDKit 39
Number of heteroatoms RDKit 13
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 15
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.42
Number of rotatable bonds RDKit 9
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
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 2
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
Licuroside
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 3
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 0.13
Licuroside
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 -9.55
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