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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:36:30 UTC
Update Date2019-07-23 06:06:17 UTC
HMDB IDHMDB0030388
Secondary Accession Numbers
  • HMDB30388
Metabolite Identification
Common Name9-(beta-D-Ribofuranosyl)zeatin
Description9-(beta-D-Ribofuranosyl)-(Z)-Zeatin is found in alfalfa. Zeatin is a plant hormone derived from the purine adenine. It is a member of the plant growth hormone family known as cytokinins. Zeatin was first discovered in immature corn kernels from the genus Zea. Zeatin and derivatives were discovered to be the primary active ingredient in coconut milk, which has long been known to actively induce plant growth. As in the case of kinetin, zeatin has also been reported to have several in vitro anti-aging effects on human skin fibroblasts.(Wikipedia).
Structure
Data?1563861977
Synonyms
ValueSource
9-(b-D-Ribofuranosyl)zeatinGenerator
9-(Β-D-ribofuranosyl)zeatinGenerator
9-Ribosyl-trans-zeatinHMDB
RibosylzeatinHMDB
trans-Zeatin ribosideHMDB
Zeatin ribosideHMDB
Zeatin-9-beta-D-ribofuranosideHMDB
N-(4-Hydroxy-3-methyl-2-butenyl)adenosineMeSH
Zeatin riboside, (cis-(Z))-isomerMeSH
Zeatin riboside, (e)-isomerMeSH
Chemical FormulaC15H21N5O5
Average Molecular Weight351.3577
Monoisotopic Molecular Weight351.154268807
IUPAC Name2-(6-{[(2E)-4-hydroxy-3-methylbut-2-en-1-yl]amino}-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
Traditional Name2-(6-{[(2E)-4-hydroxy-3-methylbut-2-en-1-yl]amino}purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
CAS Registry Number6025-53-2
SMILES
C\C(CO)=C/CNC1=NC=NC2=C1N=CN2C1OC(CO)C(O)C1O
InChI Identifier
InChI=1S/C15H21N5O5/c1-8(4-21)2-3-16-13-10-14(18-6-17-13)20(7-19-10)15-12(24)11(23)9(5-22)25-15/h2,6-7,9,11-12,15,21-24H,3-5H2,1H3,(H,16,17,18)/b8-2+
InChI KeyGOSWTRUMMSCNCW-KRXBUXKQSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleosides
Sub ClassNot Available
Direct ParentPurine nucleosides
Alternative Parents
Substituents
  • Purine nucleoside
  • Glycosyl compound
  • N-glycosyl compound
  • 6-alkylaminopurine
  • 6-aminopurine
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Secondary aliphatic/aromatic amine
  • Monosaccharide
  • N-substituted imidazole
  • Pyrimidine
  • Imidolactam
  • Tetrahydrofuran
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Secondary alcohol
  • Organoheterocyclic compound
  • Azacycle
  • Secondary amine
  • Oxacycle
  • Amine
  • Organic nitrogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Primary alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point180 - 182 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility5.27 g/LALOGPS
logP-0.39ALOGPS
logP-1.7ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)12.45ChemAxon
pKa (Strongest Basic)4.85ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area145.78 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity89.58 m³·mol⁻¹ChemAxon
Polarizability36.29 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-9068000000-19a5e7eaa36596e0d592Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-00fr-1121049000-7b3ecb3583a56cde991fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-1095000000-1b11ce6ccb21a8cbb210Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-2290000000-838b529c353cc495ea9cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fl9-9550000000-c2693909505810ea03f5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0uxr-0179000000-96bd88107bafaf0424cdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gb9-0390000000-09c663365f9cda6d9f98Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-1920000000-932e965938c1e863b090Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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
FoodDB IDFDB002240
KNApSAcK IDC00000095
Chemspider ID4525098
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5375662
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .