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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:20:55 UTC
Update Date2021-09-14 14:59:39 UTC
HMDB IDHMDB0012201
Secondary Accession Numbers
  • HMDB12201
Metabolite Identification
Common Namecis-Zeatin-7-N-glucoside
Descriptioncis-Zeatin-7-N-glucoside is an intermediate in cytokinins 7-N-glucoside biosynthesis. It is generated from cis-zeatin via the enzyme UDP glycosyltransferase. Several types of cytokinins conjugation exist which render cytokinins inactive: O-xylosylation, O-glucosylation, and N-glucosylation. When plants are subjected to high levels of cytokinin application, the major conjugate that forms is the 7-N-glucoside. Moreover, unlike O-glucosides, the glucosylation of which is reversible through the action of glucosidases, 7-N- and 9-N-glucosides are resistant to glucosidases. This, taken with N-glucosides accumulation in plants subjected to high doses of cytokinins, has led to the suggestion that N-glucosylation is involved in detoxification.
Structure
Thumb
Synonyms
Chemical FormulaC16H23N5O6
Average Molecular Weight381.389
Monoisotopic Molecular Weight381.164833481
IUPAC Name(2R,3R,4S,5S,6R)-2-(6-{[(2Z)-4-hydroxy-3-methylbut-2-en-1-yl]amino}-7H-purin-7-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-7-yl)-6-(hydroxymethyl)oxane-3,4,5-triol
CAS Registry Number823188-69-8
SMILES
C\C(CO)=C\CNC1=C2N(C=NC2=NC=N1)[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)20-7-21(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 KeyHTDHRCLVWUEXIS-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
Physiological effectNot Available
Disposition
Source
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028847
KNApSAcK IDNot Available
Chemspider ID58827659
KEGG Compound IDNot Available
BioCyc IDCPD-4618
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound101928901
PDB IDNot Available
ChEBI ID133211
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available