IMPPAT Phytochemical information: 
trans-Zeatin glucoside

trans-Zeatin glucoside
Summary

SMILES: OC/C(=C/CNc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)/C
InChI: InChI=1S/C16H23N5O6/c1-8(4-22)2-3-17-14-10-15(19-6-18-14)21(7-20-10)16-13(26)12(25)11(24)9(5-23)27-16/h2,6-7,9,11-13,16,22-26H,3-5H2,1H3,(H,17,18,19)/b8-2+/t9-,11-,12+,13-,16-/m1/s1
InChIKey: VYRAJOITMBSQSE-HNVSNYHQSA-N
DeepSMILES: OC/C=C/CNcncncc6ncn5[C@@H]O[C@H]CO))[C@H][C@@H][C@H]6O))O))O)))))))))))))))))/C
Scaffold Graph/Node/Bond level: c1ncc2ncn(C3CCCCO3)c2n1
Scaffold Graph/Node level: C1CCC(N2CNC3CNCNC32)OC1
Scaffold Graph level: C1CCC(C2CCC3CCCCC32)CC1
Functional groups: CO; C/C=C(/C)C; cNC; cnc; cn(C)c; COC
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: Pseudoalkaloids
NP Classifier Class: Purine alkaloids
Synonymous chemical names:
trans-zeatin glucoside, glucoside of trans-zeatin
External chemical identifiers:
CID:CID_9842892; ChEBI:CHEBI:133210; ZINC:ZINC000012956064
Chemical structure download


trans-Zeatin glucoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 381.39
Log P RDKit -1.85
Topological polar surface area (Å2) RDKit 166.01
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 5
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.31
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.56
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 2
Number of aromatic rings RDKit 2
Total number of rings RDKit 3
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 3


trans-Zeatin glucoside
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 1
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.31


trans-Zeatin glucoside
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -9.16
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 No