Record Information
Version1.0
Creation date2015-05-07 21:20:31 UTC
Update date2019-11-26 03:22:11 UTC
Primary IDFDB031214
Secondary Accession NumbersNot Available
Chemical Information
FooDB Nametrans-zeatin riboside
DescriptionTrans-zeatin riboside, also known as (E)-N-(4-hydroxy-3-methyl-2-butenyl)adenosine or 9-beta-D-ribofuranosyl-trans-zeatin, is a member of the class of compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety. Trans-zeatin riboside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Trans-zeatin riboside can be found in a number of food items such as winter squash, plains prickly pear, dill, and common buckwheat, which makes trans-zeatin riboside a potential biomarker for the consumption of these food products.
CAS Number6025-53-2
Structure
Thumb
Synonyms
SynonymSource
(e)-N-(4-Hydroxy-3-methyl-2-butenyl)adenosineChEBI
9-beta-D-Ribofuranosyl-trans-zeatinChEBI
9-beta-D-Ribosyl-trans-zeatinChEBI
trans-Zeatin 9-beta-D-ribofuranosideChEBI
Zeatin ribosideChEBI
9-b-D-Ribofuranosyl-trans-zeatinGenerator
9-Β-D-ribofuranosyl-trans-zeatinGenerator
9-b-D-Ribosyl-trans-zeatinGenerator
9-Β-D-ribosyl-trans-zeatinGenerator
trans-Zeatin 9-b-D-ribofuranosideGenerator
trans-Zeatin 9-β-D-ribofuranosideGenerator
RibosylzeatinMeSH
Zeatin riboside, (e)-isomerMeSH
N-(4-Hydroxy-3-methyl-2-butenyl)adenosineMeSH
Zeatin riboside, (cis-(Z))-isomerMeSH
N-[(2E)-4-Hydroxy-3-methyl-2-buten-1-yl]adenosinePhytoBank
6-(4-Hydroxy-3-methyl-trans-2-butenylamino)-9-beta-D-ribofuranosylpurinePhytoBank
6-(4-Hydroxy-3-methyl-trans-2-butenylamino)-9-β-D-ribofuranosylpurinePhytoBank
9-Ribosyl-trans-zeatinPhytoBank
9-beta-D-RibofuranosylzeatinPhytoBank
9-β-D-RibofuranosylzeatinPhytoBank
N6-(4-Hydroxy-3-methylbut-2-trans-enyl)adenosinePhytoBank
N6-(trans-4-Hydroxy-3-methylbut-2-enyl)adenosinePhytoBank
Ribosyl-trans-zeatinPhytoBank
Zeatin ribonucleosidePhytoBank
Zeatin 9-ribosidePhytoBank
Zeatin 9-beta-ribonucleosidePhytoBank
Zeatin 9-β-ribonucleosidePhytoBank
Zeatin-9-beta-D-ribofuranosidePhytoBank
Zeatin-9-β-D-ribofuranosidePhytoBank
trans-Zeatin 9-ribosidePhytoBank
trans-Zeatin ribosidePhytoBank
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)3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area145.78 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity89.58 m³·mol⁻¹ChemAxon
Polarizability36.13 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC15H21N5O5
IUPAC name(2R,3R,4S,5R)-2-(6-{[(2E)-4-hydroxy-3-methylbut-2-en-1-yl]amino}-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
InChI IdentifierInChI=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+/t9-,11-,12-,15-/m1/s1
InChI KeyGOSWTRUMMSCNCW-HNNGNKQASA-N
Isomeric SMILES[H]\C(CNC1=C2N=CN(C2=NC=N1)[C@]1([H])O[C@]([H])(CO)[C@@]([H])(O)[C@@]1([H])O)=C(\C)CO
Average Molecular Weight351.3577
Monoisotopic Molecular Weight351.154268807
Classification
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 Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MStrans-zeatin riboside, 4 TMS, GC-MS Spectrumsplash10-0udi-1960010000-d4c0888291d7c760555bSpectrum
GC-MStrans-zeatin riboside, 5 TMS, GC-MS Spectrumsplash10-0fl0-0981000000-487416c0dd63aca8c096Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-1095000000-e69a8f1cb17def92a4a2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-1290000000-b738c49b8759386cef28Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fl9-9560000000-0afd15299fe7e2b97bc3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0uxr-0069000000-52a828475d9b09a90b67Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gb9-0390000000-8892d955975636a40263Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0920000000-093f9d90276684927277Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-0069000000-b5ce3824980d905d017bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-0591000000-e7fffc9afe48c99d4c92Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f79-2970000000-a00f955f9107cd2bf526Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0019000000-b3dfb6ba4f8af83ddf51Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zg0-2492000000-e3efb65eaacbf3a0c825Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ue9-0960000000-4f16515a46c86a203379Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference