IMPPAT Phytochemical information: 
Isopentenyl-Adenine-9-glucoside

Isopentenyl-Adenine-9-glucoside
Summary

SMILES: OC[C@H]1O[C@H]([C@@H]([C@H]([C@@H]1O)O)O)n1cnc2c1ncnc2NCC=C(C)C
InChI: InChI=1S/C16H23N5O5/c1-8(2)3-4-17-14-10-15(19-6-18-14)21(7-20-10)16-13(25)12(24)11(23)9(5-22)26-16/h3,6-7,9,11-13,16,22-25H,4-5H2,1-2H3,(H,17,18,19)/t9-,11-,12+,13-,16-/m1/s1
InChIKey: XEHLLUQVSRLWMH-HDNYONAXSA-N
DeepSMILES: OC[C@H]O[C@H][C@@H][C@H][C@@H]6O))O))O))ncncc5ncnc6NCC=CC)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; COC; cn(C)c; cnc; cNC; CC=C(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: Pseudoalkaloids
NP Classifier Class: Purine alkaloids
Synonymous chemical names:
purine, 9-beta-d-glucopyranosyl-6-(3-methyl-2-butenylamino-
External chemical identifiers:
CID:CID_11675006; ZINC:ZINC000038224592
Chemical structure download


Isopentenyl-Adenine-9-glucoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 365.39
Log P RDKit -0.82
Topological polar surface area (Å2) RDKit 145.78
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 10
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 5
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


Isopentenyl-Adenine-9-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 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 0.43


Isopentenyl-Adenine-9-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 Low
Log Kp (Skin permeation, cm/s) SwissADME -8.17
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