IMPPAT Phytochemical information: 
Thesinine-4'-O-beta-D-glucoside
Thesinine-4'-O-beta-D-glucoside
Summary

SMILES: OC[C@H]1O[C@@H](Oc2ccc(cc2)/C=C/C(=O)OC[C@@H]2CCN3[C@@H]2CCC3)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C23H31NO8/c25-12-18-20(27)21(28)22(29)23(32-18)31-16-6-3-14(4-7-16)5-8-19(26)30-13-15-9-11-24-10-1-2-17(15)24/h3-8,15,17-18,20-23,25,27-29H,1-2,9-13H2/b8-5+/t15-,17+,18+,20+,21-,22+,23+/m0/s1
InChIKey: VRWXOVDCMDXQDO-VDEBYVOPSA-N
DeepSMILES: OC[C@H]O[C@@H]Occcccc6))/C=C/C=O)OC[C@@H]CCN[C@@H]5CCC5))))))))))))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C(C=Cc1ccc(OC2CCCCO2)cc1)OCC1CCN2CCCC12
Scaffold Graph/Node level: OC(CCC1CCC(OC2CCCCO2)CC1)OCC1CCN2CCCC12
Scaffold Graph level: CC(CCC1CCC(CC2CCCCC2)CC1)CCC1CCC2CCCC21
Functional groups: CO; cO[C@@H](C)OC; c/C=C/C(=O)OC; CN(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Carbohydrates and carbohydrate conjugates
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Lysine alkaloids
NP Classifier Class: Quinolizidine alkaloids
Synonymous chemical names:
thesinine-4-o-beta-d-glucoside, thesinine-4'-o-beta-d-glucoside
External chemical identifiers:
CID:CID_90478759; FDASRS:DPG1D4BJHB
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Thesinine-4'-O-beta-D-glucoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 449.5
Log P RDKit -0.09
Topological polar surface area (Å2) RDKit 128.92
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 23
Number of heavy atoms RDKit 32
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 7
Stereochemical complexity RDKit 0.3
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 14
Shape complexity RDKit 0.61
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 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 3
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
Thesinine-4'-O-beta-D-glucoside
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.33
Thesinine-4'-O-beta-D-glucoside
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -8.32
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