Showing Compound Card for cis-Zeatin-9-N-glucoside (CDB005007)

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Record Information
Version1.0
Created at2020-04-17 18:59:45 UTC
Updated at2020-11-18 16:39:12 UTC
CannabisDB IDCDB005007
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namecis-Zeatin-9-N-glucoside
Descriptioncis-Zeatin-9-N-glucoside, also known as 9-(b-D-glucosyl)-cis-zeatin, belongs to the class of organic compounds known as glycosylamines. Glycosylamines are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether). cis-Zeatin-9-N-glucoside is a strong basic compound (based on its pKa). cis-Zeatin-9-N-glucoside is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
cis-Zeatin-9-beta-D-glucosideChEBI
cis-Zeatin-9-beta-glucosideChEBI
cis-Zeatin-9-glucosideChEBI
cis-Zeatin-9-b-D-glucosideGenerator
cis-Zeatin-9-β-D-glucosideGenerator
cis-Zeatin-9-b-glucosideGenerator
cis-Zeatin-9-β-glucosideGenerator
9-(b-D-Glucosyl)-cis-zeatinHMDB
9-(Β-D-glucosyl)-cis-zeatinHMDB
(2Z)-4-[(9-beta-D-Glucopyranosyl-9H-purin-6-yl)amino]-2-methyl-2-buten-1-olHMDB
(2Z)-4-[(9-Β-D-glucopyranosyl-9H-purin-6-yl)amino]-2-methyl-2-buten-1-olHMDB
cis-Zeatin-9-N-glucosideHMDB
Chemical FormulaC16H23N5O6
Average Molecular Weight381.39
Monoisotopic Molecular Weight381.1648
IUPAC Name(2R,3R,4S,5S,6R)-2-(6-{[(2Z)-4-hydroxy-3-methylbut-2-en-1-yl]amino}-9H-purin-9-yl)-6-(hydroxymethyl)oxane-3,4,5-triol
Traditional Name(2R,3R,4S,5S,6R)-2-(6-{[(2Z)-4-hydroxy-3-methylbut-2-en-1-yl]amino}purin-9-yl)-6-(hydroxymethyl)oxane-3,4,5-triol
CAS Registry Number169565-72-4
SMILES
C\C(CO)=C\CNC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
InChI Identifier
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
InChI KeyVYRAJOITMBSQSE-MTQUCLQASA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as glycosylamines. Glycosylamines are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether).
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentGlycosylamines
Alternative Parents
Substituents
  • Hexose monosaccharide
  • N-glycosyl compound
  • 6-alkylaminopurine
  • 6-aminopurine
  • Purine
  • Imidazopyrimidine
  • Aminopyrimidine
  • Imidolactam
  • Pyrimidine
  • Monosaccharide
  • Oxane
  • N-substituted imidazole
  • Heteroaromatic compound
  • Azole
  • Imidazole
  • Secondary alcohol
  • Polyol
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Alcohol
  • Amine
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.71ALOGPS
logP-2.3ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)12.36ChemAxon
pKa (Strongest Basic)3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area166.01 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity95.54 m³·mol⁻¹ChemAxon
Polarizability37.62 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MScis-Zeatin-9-N-glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 17V, positivesplash10-00di-0092000000-c4f839f0f604db7b65c12020-07-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-4f5b185b9fd5a67cdab72021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gza-0298000000-69f3e270ddf78653bc512021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ue9-0930000000-4bcd71df5ef44a4ddfcb2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0089-0059000000-5852ba181ffe387cc01f2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-0590000000-d69b523f8aff48770ca72021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f79-1950000000-b82ca38e6ecb6c05a8db2021-09-25View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0012202
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB028848
KNApSAcK IDC00057962
Chemspider ID32042536
KEGG Compound IDNot Available
BioCyc IDCPD-4619
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound101921807
PDB IDNot Available
ChEBI ID133208
References
General ReferencesNot Available