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Record Information
Version1.0
Created at2021-01-06 07:03:55 UTC
Updated at2021-07-15 17:37:19 UTC
NP-MRD IDNP0021801
Secondary Accession NumbersNone
Natural Product Identification
Common NameZeatin riboside
Provided ByNPAtlasNPAtlas Logo
DescriptionTrans-zeatin riboside, also known as ribosylzeatin, 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. Zeatin riboside is found in Rhizopogon roseolus. It was first documented in 1967 (PMID: 6036233). Based on a literature review a small amount of articles have been published on trans-zeatin riboside (PMID: 12379786) (PMID: 20488581) (PMID: 21790030) (PMID: 21867755).
Structure
Data?1624506942
Synonyms
ValueSource
(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
Zeatin riboside, (cis-(Z))-isomerMeSH
N-(4-Hydroxy-3-methyl-2-butenyl)adenosineMeSH
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
Chemical FormulaC15H21N5O5
Average Mass351.3577 Da
Monoisotopic Mass351.15427 Da
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
Traditional Nametrans-zeatin riboside
CAS Registry NumberNot Available
SMILES
C\C(CO)=C/CNC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
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+/t9-,11-,12-,15-/m1/s1
InChI KeyGOSWTRUMMSCNCW-HNNGNKQASA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Abies balsameaKNApSAcK Database
Acer pseudoplatanusKNApSAcK Database
Actinidia chinensisKNApSAcK Database
Arabidopsis thalianaKNApSAcK Database
Beta vulgarisKNApSAcK Database
Brassica campestrisKNApSAcK Database
Brassica oleraceaKNApSAcK Database
Castanea spp.KNApSAcK Database
Cichorium intybusKNApSAcK Database
Cocos nuciferaKNApSAcK Database
Datura innoxiaKNApSAcK Database
Daucus carotaKNApSAcK Database
Dolichos lablabKNApSAcK Database
Glycine maxKNApSAcK Database
Gossypium hirsutumKNApSAcK Database
Humulus lupulusKNApSAcK Database
Ipomoea batatasKNApSAcK Database
Lupinus luteusKNApSAcK Database
Mangifera indicaKNApSAcK Database
Medicago sativaKNApSAcK Database
Mercurialis annuaKNApSAcK Database
Nicotiana tabacumKNApSAcK Database
Oryza sativaKNApSAcK Database
Phaseolus mungoKNApSAcK Database
Phaseolus vulgarisKNApSAcK Database
Picea sitchensisKNApSAcK Database
Pinus radiataKNApSAcK Database
Pisum sativumKNApSAcK Database
Prunus cerasusKNApSAcK Database
Pseudotsuga menziesiiKNApSAcK Database
Pyrus communisKNApSAcK Database
Rhizopogon roseolus
Sechium eduleKNApSAcK Database
Solanum lycopersicumKNApSAcK Database
Triticum aestivumKNApSAcK Database
Vinca roseaKNApSAcK Database
Zea maysKNApSAcK Database
Species Where Detected
Species NameSourceReference
Bradyrhizobium japonicumKNApSAcK Database
Corynebacterium fasciansKNApSAcK Database
Rhizopogon ochraceorubensKNApSAcK Database
Saccharomyces cerevisiaeKNApSAcK Database
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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
External Links
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB031214
KNApSAcK IDC00000096
Chemspider ID4945213
KEGG Compound IDC16431
BioCyc IDCPD-4208
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6440982
PDB IDNot Available
ChEBI ID71693
Good Scents IDNot Available
References
General References
  1. Miller CO: Zeatin and zeatin riboside from a mycorrhizal fungus. Science. 1967 Sep 1;157(3792):1055-7. doi: 10.1126/science.157.3792.1055. [PubMed:6036233 ]
  2. Kuroha T, Kato H, Asami T, Yoshida S, Kamada H, Satoh S: A trans-zeatin riboside in root xylem sap negatively regulates adventitious root formation on cucumber hypocotyls. J Exp Bot. 2002 Nov;53(378):2193-200. doi: 10.1093/jxb/erf077. [PubMed:12379786 ]
  3. Abul Y, Menendez V, Gomez-Campo C, Revilla MA, Lafont F, Fernandez H: Occurrence of plant growth regulators in Psilotum nudum. J Plant Physiol. 2010 Sep 15;167(14):1211-3. doi: 10.1016/j.jplph.2010.03.015. Epub 2010 May 21. [PubMed:20488581 ]
  4. Sokolova MG, Akimova GP, Vaishlia OB: [Effect of phytohormones synthesized by rhizosphere bacteria on plants]. Prikl Biokhim Mikrobiol. 2011 May-Jun;47(3):302-7. [PubMed:21790030 ]
  5. Liang Y, Zhu X, Zhao M, Liu H: Sensitive quantification of isoprenoid cytokinins in plants by selective immunoaffinity purification and high performance liquid chromatography-quadrupole-time of flight mass spectrometry. Methods. 2012 Feb;56(2):174-9. doi: 10.1016/j.ymeth.2011.08.006. Epub 2011 Aug 16. [PubMed:21867755 ]