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9-(beta-D-Ribofuranosyl)zeatin

PubChem CID
5375662
Structure
9-(beta-D-Ribofuranosyl)zeatin_small.png
9-(beta-D-Ribofuranosyl)zeatin_3D_Structure.png
Molecular Formula
Synonyms
  • 9-(beta-D-Ribofuranosyl)zeatin
  • Ribosylzeatin
  • Zeatin riboside
  • 2-(hydroxymethyl)-5-[6-[[(E)-4-hydroxy-3-methylbut-2-enyl]amino]purin-9-yl]oxolane-3,4-diol
  • 9-(b-D-Ribofuranosyl)zeatin
Molecular Weight
351.36 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
  • Create:
    2005-03-27
  • Modify:
    2025-01-18
Description
9-(beta-D-Ribofuranosyl)zeatin is a purine nucleoside.
See also: Zeatin riboside (annotation moved to).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
9-(beta-D-Ribofuranosyl)zeatin.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-(hydroxymethyl)-5-[6-[[(E)-4-hydroxy-3-methylbut-2-enyl]amino]purin-9-yl]oxolane-3,4-diol
Computed by Lexichem TK 2.7.0 (PubChem release 2021.05.07)

2.1.2 InChI

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+
Computed by InChI 1.0.6 (PubChem release 2021.05.07)

2.1.3 InChIKey

GOSWTRUMMSCNCW-KRXBUXKQSA-N
Computed by InChI 1.0.6 (PubChem release 2021.05.07)

2.1.4 SMILES

C/C(=C\CNC1=C2C(=NC=N1)N(C=N2)C3C(C(C(O3)CO)O)O)/CO
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C15H21N5O5
Computed by PubChem 2.1 (PubChem release 2021.05.07)

2.3 Other Identifiers

2.3.1 CAS

6025-53-2

2.3.2 ChEBI ID

2.3.3 HMDB ID

2.3.4 KEGG ID

2.3.5 Metabolomics Workbench ID

2.3.6 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • N-(4-hydroxy-3-methyl-2-butenyl)adenosine
  • ribosylzeatin
  • zeatin riboside
  • zeatin riboside, (cis-(Z))-isomer
  • zeatin riboside, (E)-isomer

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
351.36 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3
Property Value
-0.1
Reference
Computed by XLogP3 3.0 (PubChem release 2021.05.07)
Property Name
Hydrogen Bond Donor Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Hydrogen Bond Acceptor Count
Property Value
9
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Rotatable Bond Count
Property Value
6
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Exact Mass
Property Value
351.15426879 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
351.15426879 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
146 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Heavy Atom Count
Property Value
25
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
481
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
4
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2019.01.04)

3.2 Experimental Properties

3.2.1 Physical Description

Solid

3.2.2 Melting Point

180 - 182 °C

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 GC-MS

1 of 2
Source of Spectrum
AV-38-245-13
Copyright
Copyright © 2020-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Source of Spectrum
JZ-1992-2692-0
Copyright
Copyright © 2020-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.1.2 LC-MS

1 of 3
View All
MoNA ID
MS Category
Experimental
MS Type
LC-MS
MS Level
MS1
Instrument
Agilent 1200 RRLC; Agilent 6520 QTOF
Instrument Type
LC-APCI-QTOF
Ionization Mode
negative
Retention Time
4.027
Top 5 Peaks

386.123702 100

350.1470235 22.40

Thumbnail
Thumbnail
License
CC BY-SA
2 of 3
View All
MoNA ID
MS Category
Experimental
MS Type
LC-MS
MS Level
MS1
Instrument
Agilent 1200 RRLC; Agilent 6520 QTOF
Instrument Type
LC-APCI-QTOF
Ionization Mode
positive
Retention Time
4.024
Top 5 Peaks
352.1615765 100
Thumbnail
Thumbnail
License
CC BY-SA

6 Chemical Vendors

7 Food Additives and Ingredients

7.1 Associated Foods

8 Pharmacology and Biochemistry

8.1 MeSH Pharmacological Classification

Plant Growth Regulators
Any of the hormones produced naturally in plants and active in controlling growth and other functions. There are three primary classes: auxins, cytokinins, and gibberellins. (See all compounds classified as Plant Growth Regulators.)

8.2 Human Metabolite Information

8.2.1 Cellular Locations

  • Cytoplasm
  • Extracellular

9 Literature

9.1 Consolidated References

9.2 NLM Curated PubMed Citations

9.3 Chemical Co-Occurrences in Literature

9.4 Chemical-Gene Co-Occurrences in Literature

9.5 Chemical-Disease Co-Occurrences in Literature

10 Patents

10.1 Depositor-Supplied Patent Identifiers

11 Classification

11.1 MeSH Tree

11.2 ChEBI Ontology

11.3 MolGenie Organic Chemistry Ontology

12 Information Sources

  1. ChEBI
  2. FooDB
    LICENSE
    FooDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (FooDB) and the original publication.
    https://foodb.ca/about
  3. Human Metabolome Database (HMDB)
    LICENSE
    HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.
    http://www.hmdb.ca/citing
    9-(beta-D-Ribofuranosyl)zeatin
    http://www.hmdb.ca/metabolites/HMDB0030388
  4. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  5. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  6. Metabolomics Workbench
  7. SpectraBase
    Adenosine, N-(4-hydroxy-3-methyl-2-butenyl)-, (E)-
    https://spectrabase.com/spectrum/1iVjK4N28AS
    Adenosine, N-(4-hydroxy-3-methyl-2-butenyl)-, (E)-
    https://spectrabase.com/spectrum/Kw9fsCER1yI
  8. Wikidata
    9-(beta-D-Ribofuranosyl)zeatin
    https://www.wikidata.org/wiki/Q106041543
  9. PubChem
  10. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  11. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
CONTENTS