IMPPAT Phytochemical information: 
O-beta-D-glucosyl-trans-zeatin

O-beta-D-glucosyl-trans-zeatin
Summary

SMILES: OC[C@H]1O[C@@H](OC/C(=C/CNc2ncnc3c2[nH]cn3)/C)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C16H23N5O6/c1-8(2-3-17-14-10-15(19-6-18-10)21-7-20-14)5-26-16-13(25)12(24)11(23)9(4-22)27-16/h2,6-7,9,11-13,16,22-25H,3-5H2,1H3,(H2,17,18,19,20,21)/b8-2+/t9-,11-,12+,13-,16-/m1/s1
InChIKey: UUPDCCPAOMDMPT-HNVSNYHQSA-N
DeepSMILES: OC[C@H]O[C@@H]OC/C=C/CNcncncc6[nH]cn5))))))))))))/C))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: C(=CCOC1CCCCO1)CNc1ncnc2nc[nH]c12
Scaffold Graph/Node level: C(CCOC1CCCCO1)CNC1NCNC2NCNC12
Scaffold Graph level: C(CCCC1CCCC2CCCC12)CCC1CCCCC1
Functional groups: CO; CO[C@@H](C)OC; C/C=C(/C)C; cNC; cnc; c[nH]c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Fatty Acyls
ClassyFire Subclass: Fatty acyl glycosides
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Pseudoalkaloids
NP Classifier Class: Purine alkaloids
Synonymous chemical names:
zeatin,o-beta-d-glucosyl
External chemical identifiers:
CID:CID_5461146; ChEBI:CHEBI:38266
Chemical structure download


O-beta-D-glucosyl-trans-zeatin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 381.39
Log P RDKit -1.47
Topological polar surface area (Å2) RDKit 165.87
Number of hydrogen bond acceptors RDKit 10
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 7
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


O-beta-D-glucosyl-trans-zeatin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 RDKit Passed
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


O-beta-D-glucosyl-trans-zeatin
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 -9.29
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