Hmdb loader
Show more...Show more...Show more...
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:21:06 UTC
Update Date2021-09-14 15:37:04 UTC
HMDB IDHMDB0012212
Secondary Accession Numbers
  • HMDB12212
Metabolite Identification
Common NameDihydrozeatin-9-N-glucoside-O-glucoside
DescriptionDihydrozeatin-9-N-glucoside-O-glucoside is involved in the cytokinin O-glucoside biosynthesis which occurs in the nuclei and cytosol of plant cells. Cytokinins play an important role in the regulation of numerous physiological reactions in plants. Dihydrozeatin undergoes an N-glucosylation to form dihydrozeatin-9-N-glucoside. This product is then conjugated into an O-glucoside. This latter reaction is reversible and beta-glucosidases can remove the addition at the O-position, which yields back dihydrozeatin-9-N-glucoside. The molecule can then regain its physiological activity. The process is perceived as a way to store the molecule by inactivating it temporarily.
Structure
Thumb
Synonyms
ValueSource
Dihydrozeatin-9-N-glucoside-O-glucosideHMDB
Chemical FormulaC22H35N5O11
Average Molecular Weight545.546
Monoisotopic Molecular Weight545.233306967
IUPAC Name(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(6-{[(3S)-3-methyl-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl]amino}-9H-purin-9-yl)oxane-3,4,5-triol
Traditional Name(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(6-{[(3S)-3-methyl-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl]amino}purin-9-yl)oxane-3,4,5-triol
CAS Registry Number619326-04-4
SMILES
C[C@@H](CCNC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
InChI Identifier
InChI=1S/C22H35N5O11/c1-9(6-36-22-18(35)16(33)14(31)11(5-29)38-22)2-3-23-19-12-20(25-7-24-19)27(8-26-12)21-17(34)15(32)13(30)10(4-28)37-21/h7-11,13-18,21-22,28-35H,2-6H2,1H3,(H,23,24,25)/t9-,10+,11+,13+,14+,15-,16-,17+,18+,21+,22+/m0/s1
InChI KeyKDIRTCPHKDPWMQ-ADPNGTSNSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl glycosides
Direct ParentFatty acyl glycosides of mono- and disaccharides
Alternative Parents
Substituents
  • Fatty acyl glycoside of mono- or disaccharide
  • Alkyl glycoside
  • 6-alkylaminopurine
  • O-glycosyl compound
  • N-glycosyl compound
  • Glycosyl compound
  • 6-aminopurine
  • Purine
  • Imidazopyrimidine
  • Secondary aliphatic/aromatic amine
  • Aminopyrimidine
  • Imidolactam
  • Pyrimidine
  • Oxane
  • N-substituted imidazole
  • Monosaccharide
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Polyol
  • Acetal
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Role
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 IDFDB028857
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDCPD-4621
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound156907998
PDB IDNot Available
ChEBI IDNot Available
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 References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.